diff --git a/code/action_executor.py b/code/action_executor.py new file mode 100644 index 0000000000000000000000000000000000000000..b830a9b241b7ced7ee5d2bb1445a2dcf7217cd8b --- /dev/null +++ b/code/action_executor.py @@ -0,0 +1,654 @@ +""" +ActionExecutor — general-purpose molecular editing via a clean JSON Action protocol. + +Design: + - Graph-level: ChangeAtom, AddAtom, RemoveAtom, ChangeBond, AddBond, RemoveBond + - Shorthand: AddGroup, RemoveGroup + - Stereo: FlipChirality, FlipEZ + - Semantic: MoveSubstituent, SwapSubstituents + - Composite: Batch + +AtomRef (how to select an atom in the input SMILES): + {"map_num": 5} atom map number (preferred) + {"smarts": "[NH2]", "match_idx": 0} SMARTS pattern (most flexible) + {"idx": 3} raw atom index (fragile) + +BondRef: + {"atom1": , "atom2": } + +Usage: + ex = ActionExecutor() + new_smiles = ex.execute("CCO", {"type": "ChangeAtom", "atom": {"idx": 2}, "element": "N"}) + # → "CCN" +""" + +import copy +import sys, os +sys.path.insert(0, os.path.dirname(__file__)) + +from rdkit import Chem +from rdkit.Chem import rdmolops +from rdkit import RDLogger +RDLogger.DisableLog("rdApp.*") + +from mol_ops import ( + BOND_TYPE_MAP, ELEM_TO_NUM, + add_functional_group, remove_functional_group, flip_ez, +) + + +# --------------------------------------------------------------------------- +# Exceptions +# --------------------------------------------------------------------------- + +class ActionError(Exception): + """Base class for all executor errors.""" + +class AtomNotFoundError(ActionError): + """Raised when an AtomRef cannot be resolved.""" + +class BondNotFoundError(ActionError): + """Raised when a BondRef cannot be resolved.""" + +class InvalidMolError(ActionError): + """Raised when an operation produces an invalid molecule.""" + +class UnknownActionError(ActionError): + """Raised for unsupported action types.""" + + +# --------------------------------------------------------------------------- +# Helpers +# --------------------------------------------------------------------------- + +BOND_STEREO_MAP = { + "E": Chem.BondStereo.STEREOE, + "Z": Chem.BondStereo.STEREOZ, + "CIS": Chem.BondStereo.STEREOZ, + "TRANS": Chem.BondStereo.STEREOE, + "NONE": Chem.BondStereo.STEREONONE, +} + + +def _sanitize(rw, context=""): + try: + Chem.SanitizeMol(rw) + except Exception as e: + raise InvalidMolError(f"Sanitization failed{' (' + context + ')' if context else ''}: {e}") + + +def _reset_atom_hs(atom): + """Clear explicit Hs and radical state so SanitizeMol recomputes implicit Hs.""" + atom.SetNumExplicitHs(0) + atom.SetNoImplicit(False) + atom.SetNumRadicalElectrons(0) + + +def _kekulize_rw(rw: Chem.RWMol) -> Chem.RWMol: + """Return a copy with aromatic bonds replaced by explicit single/double (Kekulé form).""" + rw2 = Chem.RWMol(copy.deepcopy(rw)) + Chem.Kekulize(rw2, clearAromaticFlags=True) + return rw2 + + +def _to_canonical(mol): + for a in mol.GetAtoms(): + a.SetAtomMapNum(0) + return Chem.MolToSmiles(mol) + + +def _shared_rings(mol, idx1, idx2): + """Return set of ring-atom-index sets that contain both idx1 and idx2.""" + ri = mol.GetRingInfo() + return [r for r in ri.AtomRings() if idx1 in r and idx2 in r] + + +# --------------------------------------------------------------------------- +# ActionExecutor +# --------------------------------------------------------------------------- + +class ActionExecutor: + """ + Apply a JSON Action to a SMILES string and return the modified SMILES. + + Public API: + execute(smiles, action) → str + execute_batch(smiles, actions) → str + """ + + # ── Atom / Bond resolution ─────────────────────────────────────────────── + + def _resolve_atom(self, mol, ref: dict) -> int: + """Resolve an AtomRef dict to a concrete atom index in mol.""" + if "map_num" in ref: + mn = ref["map_num"] + for a in mol.GetAtoms(): + if a.GetAtomMapNum() == mn: + return a.GetIdx() + raise AtomNotFoundError(f"No atom with map_num={mn}") + + if "smarts" in ref: + patt = Chem.MolFromSmarts(ref["smarts"]) + if patt is None: + raise AtomNotFoundError(f"Invalid SMARTS: {ref['smarts']!r}") + matches = mol.GetSubstructMatches(patt) + mi = ref.get("match_idx", 0) + if not matches or mi >= len(matches): + raise AtomNotFoundError( + f"SMARTS {ref['smarts']!r} match_idx={mi}: " + f"found {len(matches)} match(es)" + ) + return matches[mi][0] + + if "idx" in ref: + idx = ref["idx"] + if idx < 0 or idx >= mol.GetNumAtoms(): + raise AtomNotFoundError(f"idx={idx} out of range (mol has {mol.GetNumAtoms()} atoms)") + return idx + + raise AtomNotFoundError(f"AtomRef must have 'map_num', 'smarts', or 'idx': got {ref}") + + def _resolve_bond(self, mol, bond_ref: dict): + """Resolve a BondRef to (idx1, idx2, Bond).""" + i1 = self._resolve_atom(mol, bond_ref["atom1"]) + i2 = self._resolve_atom(mol, bond_ref["atom2"]) + bond = mol.GetBondBetweenAtoms(i1, i2) + if bond is None: + raise BondNotFoundError(f"No bond between atom idx {i1} and {i2}") + return i1, i2, bond + + # ── Action handlers ────────────────────────────────────────────────────── + + def _change_atom(self, rw: Chem.RWMol, action: dict): + idx = self._resolve_atom(rw, action["atom"]) + atom = rw.GetAtomWithIdx(idx) + + if "element" in action: + n = ELEM_TO_NUM.get(action["element"]) + if n is None: + raise ActionError(f"Unknown element: {action['element']!r}") + atom.SetAtomicNum(n) + atom.SetNoImplicit(False) + + if "charge" in action: + atom.SetFormalCharge(int(action["charge"])) + _reset_atom_hs(atom) + + if "isotope" in action and action["isotope"] is not None: + atom.SetIsotope(int(action["isotope"])) + + if "num_hs" in action and action["num_hs"] is not None: + atom.SetNumExplicitHs(int(action["num_hs"])) + atom.SetNoImplicit(True) + + atom.UpdatePropertyCache(strict=False) + _sanitize(rw, "ChangeAtom") + return rw + + def _add_atom(self, rw: Chem.RWMol, action: dict): + anchor_idx = self._resolve_atom(rw, action["anchor"]) + elem = action["element"] + n = ELEM_TO_NUM.get(elem) + if n is None: + raise ActionError(f"Unknown element: {elem!r}") + + order = action.get("bond_order", "SINGLE").upper() + bond_type = BOND_TYPE_MAP.get(order) + if bond_type is None: + raise ActionError(f"Unknown bond order: {order!r}") + + new_idx = rw.AddAtom(Chem.Atom(n)) + new_atom = rw.GetAtomWithIdx(new_idx) + + if "charge" in action: + new_atom.SetFormalCharge(int(action["charge"])) + if "num_hs" in action and action["num_hs"] is not None: + new_atom.SetNumExplicitHs(int(action["num_hs"])) + + _reset_atom_hs(rw.GetAtomWithIdx(anchor_idx)) + + rw.AddBond(anchor_idx, new_idx, bond_type) + _sanitize(rw, "AddAtom") + return rw + + def _remove_atom(self, rw: Chem.RWMol, action: dict): + idx = self._resolve_atom(rw, action["atom"]) + neighbors = [n.GetIdx() for n in rw.GetAtomWithIdx(idx).GetNeighbors()] + rw.RemoveAtom(idx) + for nidx in neighbors: + adj = nidx if nidx < idx else nidx - 1 + if adj < rw.GetNumAtoms(): + _reset_atom_hs(rw.GetAtomWithIdx(adj)) + _sanitize(rw, "RemoveAtom") + return rw + + def _change_bond(self, rw: Chem.RWMol, action: dict): + i1, i2, bond = self._resolve_bond(rw, action["bond"]) + order = action["order"].upper() + bond_type = BOND_TYPE_MAP.get(order) + if bond_type is None: + raise ActionError(f"Unknown bond order: {order!r}") + bond.SetBondType(bond_type) + + if "stereo" in action and action["stereo"]: + stereo = BOND_STEREO_MAP.get(action["stereo"].upper()) + if stereo is not None: + bond.SetStereo(stereo) + + for idx in (i1, i2): + _reset_atom_hs(rw.GetAtomWithIdx(idx)) + _sanitize(rw, "ChangeBond") + return rw + + def _add_bond(self, rw: Chem.RWMol, action: dict): + i1 = self._resolve_atom(rw, action["bond"]["atom1"]) + i2 = self._resolve_atom(rw, action["bond"]["atom2"]) + if rw.GetBondBetweenAtoms(i1, i2) is not None: + raise ActionError(f"Bond already exists between atoms {i1} and {i2}") + order = action.get("order", "SINGLE").upper() + bond_type = BOND_TYPE_MAP.get(order) + if bond_type is None: + raise ActionError(f"Unknown bond order: {order!r}") + rw.AddBond(i1, i2, bond_type) + for idx in (i1, i2): + _reset_atom_hs(rw.GetAtomWithIdx(idx)) + _sanitize(rw, "AddBond") + return rw + + def _remove_bond(self, rw: Chem.RWMol, action: dict): + i1, i2, _ = self._resolve_bond(rw, action["bond"]) + rw.RemoveBond(i1, i2) + for idx in (i1, i2): + _reset_atom_hs(rw.GetAtomWithIdx(idx)) + _sanitize(rw, "RemoveBond") + return rw + + def _add_group(self, rw: Chem.RWMol, action: dict): + anchor = self._resolve_atom(rw, action["anchor"]) + group = action["group"] + result = add_functional_group(rw, anchor_idx=anchor, group_name=group) + if result is None: + raise InvalidMolError(f"AddGroup failed: group={group!r} anchor={anchor}") + return Chem.RWMol(result) + + def _remove_group(self, rw: Chem.RWMol, action: dict): + anchor = self._resolve_atom(rw, action["anchor"]) + group = action["group"] + result, removed = remove_functional_group(rw, anchor_idx=anchor, group_name=group) + if result is None: + raise InvalidMolError( + f"RemoveGroup failed: group={group!r} not found at anchor={anchor}" + ) + rw2 = Chem.RWMol(result) + _reset_atom_hs(rw2.GetAtomWithIdx(anchor)) + _sanitize(rw2, "RemoveGroup") + return rw2 + + def _flip_chirality(self, rw: Chem.RWMol, action: dict): + idx = self._resolve_atom(rw, action["atom"]) + atom = rw.GetAtomWithIdx(idx) + chi = atom.GetChiralTag() + if chi == Chem.ChiralType.CHI_TETRAHEDRAL_CW: + atom.SetChiralTag(Chem.ChiralType.CHI_TETRAHEDRAL_CCW) + elif chi == Chem.ChiralType.CHI_TETRAHEDRAL_CCW: + atom.SetChiralTag(Chem.ChiralType.CHI_TETRAHEDRAL_CW) + else: + raise ActionError(f"Atom idx={idx} has no specified chirality to flip") + _sanitize(rw, "FlipChirality") + return rw + + def _flip_ez(self, smiles: str, action: dict) -> str: + """ + FlipEZ: invert E/Z at SMILES level. + If 'bond' is provided, validates it's a double bond first. + """ + mol = Chem.MolFromSmiles(smiles) + if mol is None: + raise InvalidMolError(f"Cannot parse SMILES: {smiles!r}") + + if "bond" in action: + i1, i2, bond = self._resolve_bond(mol, action["bond"]) + if bond.GetBondType() != Chem.BondType.DOUBLE: + raise ActionError( + f"FlipEZ: bond between atoms {i1} and {i2} is not a double bond" + ) + + smi = Chem.MolToSmiles(mol, isomericSmiles=True) + if "/" not in smi and "\\" not in smi: + raise ActionError("FlipEZ: SMILES has no E/Z notation to flip") + + result = flip_ez(smi) + if result is None or result == smi: + raise ActionError("FlipEZ: flip produced no change or invalid molecule") + # Strip atom map numbers and return canonical form + mol_r = Chem.MolFromSmiles(result) + if mol_r is None: + raise InvalidMolError(f"FlipEZ produced invalid SMILES: {result!r}") + return _to_canonical(mol_r) + + def _move_substituent(self, rw: Chem.RWMol, action: dict): + """ + Detach `substituent` from `from_atom` and reattach it to `to_atom`. + Works on aromatic rings by operating in Kekulé form. + """ + sub_idx = self._resolve_atom(rw, action["substituent"]) + from_idx = self._resolve_atom(rw, action["from_atom"]) + to_idx = self._resolve_atom(rw, action["to_atom"]) + + bond = rw.GetBondBetweenAtoms(from_idx, sub_idx) + if bond is None: + raise BondNotFoundError( + f"MoveSubstituent: no bond between from_atom={from_idx} and substituent={sub_idx}" + ) + bond_type = bond.GetBondType() + # Use SINGLE for substituent attachment (aromatic bond → substituent is always single) + if bond_type == Chem.BondType.AROMATIC: + bond_type = Chem.BondType.SINGLE + + if rw.GetBondBetweenAtoms(to_idx, sub_idx) is not None: + raise ActionError( + f"MoveSubstituent: bond already exists between to_atom={to_idx} and substituent={sub_idx}" + ) + + rw = _kekulize_rw(rw) + rw.RemoveBond(from_idx, sub_idx) + # Reset explicit Hs on both endpoints so valence is recomputed by sanitize + for i in (from_idx, to_idx): + _reset_atom_hs(rw.GetAtomWithIdx(i)) + rw.AddBond(to_idx, sub_idx, bond_type) + _sanitize(rw, "MoveSubstituent") + return rw + + def _swap_substituents(self, rw: Chem.RWMol, action: dict): + """ + Swap all non-ring substituents between two atoms (typically ring atoms). + Works on aromatic rings by operating in Kekulé form. + """ + idx1 = self._resolve_atom(rw, action["atom1"]) + idx2 = self._resolve_atom(rw, action["atom2"]) + + if idx1 == idx2: + raise ActionError("SwapSubstituents: atom1 and atom2 are the same atom") + + shared_ring_atoms = set() + for ring in _shared_rings(rw, idx1, idx2): + shared_ring_atoms.update(ring) + + def get_substituents(center, other_center): + subs = [] + for nb in rw.GetAtomWithIdx(center).GetNeighbors(): + nidx = nb.GetIdx() + if nidx in shared_ring_atoms and nidx != other_center: + continue + if nidx == other_center: + continue + subs.append((nidx, rw.GetBondBetweenAtoms(center, nidx).GetBondType())) + return subs + + subs1 = get_substituents(idx1, idx2) + subs2 = get_substituents(idx2, idx1) + + rw = _kekulize_rw(rw) + + for sub_idx, _ in subs1: + rw.RemoveBond(idx1, sub_idx) + for sub_idx, _ in subs2: + rw.RemoveBond(idx2, sub_idx) + + # Reset explicit Hs on swap targets so valence is recomputed + for center in (idx1, idx2): + _reset_atom_hs(rw.GetAtomWithIdx(center)) + + for sub_idx, btype in subs1: + bt = Chem.BondType.SINGLE if btype == Chem.BondType.AROMATIC else btype + rw.AddBond(idx2, sub_idx, bt) + for sub_idx, btype in subs2: + bt = Chem.BondType.SINGLE if btype == Chem.BondType.AROMATIC else btype + rw.AddBond(idx1, sub_idx, bt) + + _sanitize(rw, "SwapSubstituents") + return rw + + # ── Dispatch ───────────────────────────────────────────────────────────── + + _SMILES_LEVEL = {"FlipEZ", "Batch"} + + def _dispatch(self, smiles: str, action: dict) -> str: + atype = action.get("type") + if not atype: + raise UnknownActionError("Action dict missing 'type' key") + + # Batch: apply actions sequentially at SMILES level + if atype == "Batch": + for sub in action["actions"]: + smiles = self.execute(smiles, sub) + return smiles + + # FlipEZ: SMILES-level operation + if atype == "FlipEZ": + return self._flip_ez(smiles, action) + + # All other ops: work on RWMol + mol = Chem.MolFromSmiles(smiles) + if mol is None: + raise InvalidMolError(f"Cannot parse SMILES: {smiles!r}") + rw = Chem.RWMol(copy.deepcopy(mol)) + + handlers = { + "ChangeAtom": self._change_atom, + "AddAtom": self._add_atom, + "RemoveAtom": self._remove_atom, + "ChangeBond": self._change_bond, + "AddBond": self._add_bond, + "RemoveBond": self._remove_bond, + "AddGroup": self._add_group, + "RemoveGroup": self._remove_group, + "FlipChirality": self._flip_chirality, + "MoveSubstituent": self._move_substituent, + "SwapSubstituents": self._swap_substituents, + } + + handler = handlers.get(atype) + if handler is None: + raise UnknownActionError( + f"Unknown action type: {atype!r}. " + f"Valid types: {sorted(handlers) + ['FlipEZ', 'Batch']}" + ) + + result_rw = handler(rw, action) + return _to_canonical(result_rw) + + # ── Public API ──────────────────────────────────────────────────────────── + + def execute(self, smiles: str, action: dict) -> str: + """ + Apply a single Action to smiles. + + Args: + smiles: input SMILES string (with or without atom map numbers) + action: Action dict with 'type' key and type-specific fields + + Returns: + Canonical SMILES after applying the action. + + Raises: + AtomNotFoundError, BondNotFoundError, InvalidMolError, UnknownActionError + """ + return self._dispatch(smiles, action) + + def execute_batch(self, smiles: str, actions: list) -> str: + """ + Apply a list of Actions sequentially. + + Equivalent to: execute(smiles, {"type": "Batch", "actions": actions}) + """ + return self._dispatch(smiles, {"type": "Batch", "actions": actions}) + + +# --------------------------------------------------------------------------- +# Inline tests +# --------------------------------------------------------------------------- + +if __name__ == "__main__": + ex = ActionExecutor() + passed = failed = 0 + + def test(name, smiles, action, expected): + global passed, failed + try: + result = ex.execute(smiles, action) + exp_canon = Chem.MolToSmiles(Chem.MolFromSmiles(expected)) + if result == exp_canon: + print(f" PASS {name}") + passed += 1 + else: + print(f" FAIL {name}") + print(f" input: {smiles}") + print(f" expected: {exp_canon}") + print(f" got: {result}") + failed += 1 + except Exception as e: + print(f" ERROR {name}: {e}") + failed += 1 + + print("=" * 60) + print("ActionExecutor — inline tests") + print("=" * 60) + + # 1. ChangeAtom — element + test("ChangeAtom/element", + "CCCO", + {"type": "ChangeAtom", "atom": {"idx": 2}, "element": "N"}, + "CCNO") + + # 2. ChangeAtom — charge + test("ChangeAtom/charge", + "CC(=O)[O-]", + {"type": "ChangeAtom", "atom": {"smarts": "[O-]"}, "charge": 0}, + "CC([O])=O") # canonical RDKit form of acetic acid + + # 3. AddAtom — via idx + try: + r = ex.execute("CCO", {"type": "AddAtom", "anchor": {"idx": 1}, "element": "C"}) + assert Chem.MolFromSmiles(r) is not None + print(" PASS AddAtom") + passed += 1 + except Exception as e: + print(f" FAIL AddAtom: {e}") + failed += 1 + + # 4. RemoveAtom — via smarts + test("RemoveAtom", + "CCO", + {"type": "RemoveAtom", "atom": {"smarts": "[OH]"}}, + "CC") + + # 5. ChangeBond — DOUBLE→SINGLE (C=O → C-O in acetaldehyde) + test("ChangeBond", + "CC=O", + {"type": "ChangeBond", + "bond": {"atom1": {"idx": 1}, "atom2": {"idx": 2}}, + "order": "SINGLE"}, + "CCO") + + # 6. AddBond + test("AddBond", + "CCCC", + {"type": "AddBond", + "bond": {"atom1": {"idx": 0}, "atom2": {"idx": 3}}, + "order": "SINGLE"}, + "C1CCC1") + + # 7. RemoveBond + test("RemoveBond", + "C1CCC1", + {"type": "RemoveBond", + "bond": {"atom1": {"smarts": "[CH2]", "match_idx": 0}, + "atom2": {"smarts": "[CH2]", "match_idx": 3}}}, + "CCCC") + + # 8. AddGroup + test("AddGroup", + "c1ccccc1", + {"type": "AddGroup", "anchor": {"idx": 0}, "group": "OH"}, + "Oc1ccccc1") + + # 9. RemoveGroup + test("RemoveGroup", + "Oc1ccccc1", + {"type": "RemoveGroup", "anchor": {"smarts": "[c;r6]", "match_idx": 0}, "group": "OH"}, + "c1ccccc1") + + # 10. FlipChirality — via smarts + test("FlipChirality", + "C[C@@H](O)F", + {"type": "FlipChirality", "atom": {"smarts": "[C@@H]"}}, + "C[C@H](O)F") + + # 11. FlipEZ + test("FlipEZ", + "C/C=C/C", + {"type": "FlipEZ", + "bond": {"atom1": {"idx": 1}, "atom2": {"idx": 2}}}, + "C/C=C\\C") + + # 12. MoveSubstituent — move Cl from position 1 to position 3 on pyridine + # pyridine with Cl at C2: Clc1ccccn1 → move Cl to C4: c1cc(Cl)ccn1 + test("MoveSubstituent", + "Clc1ccccn1", + {"type": "MoveSubstituent", + "substituent": {"smarts": "[Cl]"}, + "from_atom": {"smarts": "[c;r6]", "match_idx": 0}, + "to_atom": {"smarts": "[c;r6]", "match_idx": 2}}, + "c1cc(Cl)ccn1") + + # 13. SwapSubstituents — on o-chlorotoluene, swap Cl and CH3 + # Cc1ccccc1Cl → Clc1ccccc1C (same thing, test canonical form) + try: + mol_in = Chem.MolFromSmiles("Cc1ccccc1Cl") + # assign map nums for stable ref + rw = Chem.RWMol(mol_in) + for a in rw.GetAtoms(): + a.SetAtomMapNum(a.GetIdx() + 1) + mapped = Chem.MolToSmiles(rw) + + # find the two substituted ring carbons + c_idx = next(a.GetIdx() for a in rw.GetAtoms() + if a.GetAtomicNum() == 6 and not a.GetIsAromatic() + and any(nb.GetIsAromatic() for nb in a.GetNeighbors())) + cl_nb = next(a for a in rw.GetAtoms() if a.GetAtomicNum() == 17) + cl_ring = next(nb.GetIdx() for nb in cl_nb.GetNeighbors()) + ch3_ring = next(nb.GetIdx() for nb in rw.GetAtomWithIdx(c_idx).GetNeighbors() + if nb.GetIsAromatic()) + + r = ex.execute(mapped, { + "type": "SwapSubstituents", + "atom1": {"map_num": ch3_ring + 1}, + "atom2": {"map_num": cl_ring + 1}, + }) + mol_r = Chem.MolFromSmiles(r) + assert mol_r is not None + print(f" PASS SwapSubstituents ({Chem.MolToSmiles(mol_in)} → {r})") + passed += 1 + except Exception as e: + print(f" FAIL SwapSubstituents: {e}") + failed += 1 + + # 14. Batch — two actions + test("Batch", + "CCO", + {"type": "Batch", "actions": [ + {"type": "ChangeAtom", "atom": {"idx": 2}, "element": "N"}, + {"type": "AddGroup", "anchor": {"idx": 2}, "group": "CH3"}, + ]}, + "CCN(C)") + + # 15. map_num AtomRef (with pre-mapped SMILES) + test("AtomRef/map_num", + "[CH3:1][CH2:2][OH:3]", + {"type": "ChangeAtom", "atom": {"map_num": 3}, "element": "N"}, + "CCN") + + print("=" * 60) + print(f"Results: {passed} passed, {failed} failed out of {passed+failed} tests") + print("=" * 60) diff --git a/code/benchmark_eval.py b/code/benchmark_eval.py new file mode 100644 index 0000000000000000000000000000000000000000..5d605124e67b8358722797bafedb2c0030c7c434 --- /dev/null +++ b/code/benchmark_eval.py @@ -0,0 +1,400 @@ +""" +Benchmark evaluator for MolEdit dataset. + +Sends (wrong_smiles_mapped + correct_image) to a vision LLM, asks it to predict +the correction action in ActionExecutor JSON format, then verifies execution. + +Usage: + # Dry run — prints prompt for first sample, no API call + python benchmark_eval.py --dataset ./data/pubchem_dataset --dry_run + + # Real run + python benchmark_eval.py \\ + --dataset ./data/pubchem_dataset \\ + --model gpt-4o \\ + --api_key sk-... \\ + --api_base https://api.openai.com/v1 \\ + --out ./data/pubchem_dataset/benchmark_results.json \\ + --n 20 + + # Filter to one op type + python benchmark_eval.py ... --op change_atom_element +""" + +import os, sys, json, re, time, base64, argparse, random, threading +from collections import defaultdict +from concurrent.futures import ThreadPoolExecutor, as_completed +sys.path.insert(0, os.path.dirname(__file__)) + +from rdkit import Chem, RDLogger +RDLogger.DisableLog("rdApp.*") + +from action_executor import ActionExecutor, ActionError + +# --------------------------------------------------------------------------- +# Op type name mapping: dataset format → ActionExecutor type +# --------------------------------------------------------------------------- + +OLD_TO_NEW_TYPE = { + "change_atom_element": "ChangeAtom", + "change_charge": "ChangeAtom", + "add_atom": "AddAtom", + "remove_atom": "RemoveAtom", + "change_bond_order": "ChangeBond", + "add_bond": "AddBond", + "remove_bond": "RemoveBond", + "add_functional_group": "AddGroup", + "remove_functional_group": "RemoveGroup", + "flip_chirality": "FlipChirality", + "flip_ez": "FlipEZ", + "move_substituent": "MoveSubstituent", + "swap_substituents": "SwapSubstituents", +} + +# --------------------------------------------------------------------------- +# System prompt +# --------------------------------------------------------------------------- + +SYSTEM_PROMPT = """You are a molecular structure correction assistant. + +You will be shown: + 1. An image of the CORRECT molecule + 2. A SMILES string with atom map numbers (:[n] tags) representing the WRONG molecule + +Your task: identify what is wrong and output a single JSON action that corrects the wrong SMILES to match the image. + +## Action types and schemas + + ChangeAtom: {"type": "ChangeAtom", "atom": AtomRef, "element": str, "charge": int} + AddAtom: {"type": "AddAtom", "anchor": AtomRef, "element": str, "bond_order": str} + RemoveAtom: {"type": "RemoveAtom", "atom": AtomRef} + ChangeBond: {"type": "ChangeBond", "bond": BondRef, "order": str} + AddBond: {"type": "AddBond", "bond": BondRef, "order": str} + RemoveBond: {"type": "RemoveBond", "bond": BondRef} + AddGroup: {"type": "AddGroup", "anchor": AtomRef, "group": str} + RemoveGroup: {"type": "RemoveGroup", "anchor": AtomRef, "group": str} + FlipChirality: {"type": "FlipChirality", "atom": AtomRef} + FlipEZ: {"type": "FlipEZ"} + MoveSubstituent: {"type": "MoveSubstituent", "substituent": AtomRef, "from_atom": AtomRef, "to_atom": AtomRef} + SwapSubstituents: {"type": "SwapSubstituents", "atom1": AtomRef, "atom2": AtomRef} + +## AtomRef and BondRef + + AtomRef: {"map_num": } ← the number after : in the SMILES, e.g. :5 → map_num 5 + BondRef: {"atom1": AtomRef, "atom2": AtomRef} + +## Valid values + + bond_order: "SINGLE" | "DOUBLE" | "TRIPLE" + group: "OH" | "NH2" | "F" | "Cl" | "Br" | "CH3" | "COOH" | "CHO" | "NO2" + element: standard element symbol, e.g. "C", "N", "O", "S", "F", "Cl", "Br" + +## Output format + +Output ONLY a valid JSON object with no additional text or explanation. +Example: {"type": "ChangeAtom", "atom": {"map_num": 3}, "element": "N"} +""" + +# --------------------------------------------------------------------------- +# Helpers +# --------------------------------------------------------------------------- + +def _img_to_b64(path): + with open(path, "rb") as f: + return base64.b64encode(f.read()).decode() + + +def _extract_json(raw: str): + """Parse JSON from LLM output, handling markdown fences.""" + raw = raw.strip() + # Try direct parse first + try: + return json.loads(raw) + except json.JSONDecodeError: + pass + # Strip markdown fences + m = re.search(r"```(?:json)?\s*(\{.*?\})\s*```", raw, re.DOTALL) + if m: + try: + return json.loads(m.group(1)) + except json.JSONDecodeError: + pass + # Find first {...} block + m = re.search(r"\{.*\}", raw, re.DOTALL) + if m: + try: + return json.loads(m.group(0)) + except json.JSONDecodeError: + pass + return None + + +def _canon(smiles): + if smiles is None: + return None + mol = Chem.MolFromSmiles(smiles) + return Chem.MolToSmiles(mol) if mol else None + + +# --------------------------------------------------------------------------- +# BenchmarkEvaluator +# --------------------------------------------------------------------------- + +class BenchmarkEvaluator: + def __init__(self, model, api_key, api_base, dataset_dir, delay=0.5, workers=4): + self.model = model + self.dataset_dir = dataset_dir + self.delay = delay + self.workers = workers + self.executor = ActionExecutor() + self._lock = threading.Lock() + + if api_key and model: + import openai + self.client = openai.OpenAI(api_key=api_key, base_url=api_base) + else: + self.client = None + + # ── Data loading ───────────────────────────────────────────────────────── + + def _load_dataset(self, n=None, op_filter=None, seed=0): + for fname in ("dataset.json", "roundtrip_test.json"): + p = os.path.join(self.dataset_dir, fname) + if os.path.exists(p): + with open(p) as f: + records = json.load(f) + break + else: + raise FileNotFoundError(f"No dataset JSON in {self.dataset_dir}") + + if op_filter: + records = [r for r in records if r["operation"]["type"] == op_filter] + + if n and n < len(records): + random.seed(seed) + records = random.sample(records, n) + + return records + + # ── LLM call ───────────────────────────────────────────────────────────── + + def _call_llm(self, record): + img_path = os.path.join(self.dataset_dir, record["image_path"]) + b64 = _img_to_b64(img_path) + + messages = [ + {"role": "system", "content": SYSTEM_PROMPT}, + { + "role": "user", + "content": [ + { + "type": "text", + "text": f"Wrong SMILES (with atom map numbers): {record['wrong_smiles_mapped']}\n\nThe image below shows the CORRECT molecule. Output the JSON action to fix the wrong SMILES.", + }, + { + "type": "image_url", + "image_url": {"url": f"data:image/png;base64,{b64}"}, + }, + ], + }, + ] + + resp = self.client.chat.completions.create( + model=self.model, + messages=messages, + max_tokens=4096, + temperature=0, + ) + return resp.choices[0].message.content + + # ── Evaluate one record ─────────────────────────────────────────────────── + + def _evaluate_one(self, record, raw_output): + op_type = record["operation"]["type"] + gt_ae_type = OLD_TO_NEW_TYPE.get(op_type, op_type) + result = { + "id": record.get("id"), + "op_type": op_type, + "image_path": record.get("image_path"), + "wrong_smiles_mapped": record["wrong_smiles_mapped"], + "correct_smiles": record["correct_smiles"], + "predicted_raw": raw_output, + "predicted_action": None, + "restored_smiles": None, + "exec_match": False, + "type_match": False, + "parse_error": False, + "exec_error": None, + } + + # 1. Parse + action = _extract_json(raw_output) + if action is None: + result["parse_error"] = True + return result + result["predicted_action"] = action + + # 2. Type match + result["type_match"] = (action.get("type") == gt_ae_type) + + # 3. Execute + try: + restored = self.executor.execute(record["wrong_smiles_mapped"], action) + result["restored_smiles"] = restored + except ActionError as e: + result["exec_error"] = str(e) + return result + except Exception as e: + result["exec_error"] = f"unexpected: {e}" + return result + + # 4. Compare (canonical) + result["exec_match"] = (_canon(restored) == _canon(record["correct_smiles"])) + return result + + # ── Report ──────────────────────────────────────────────────────────────── + + def _report(self, results, out_path=None): + by_op = defaultdict(list) + for r in results: + by_op[r["op_type"]].append(r) + + total = len(results) + total_exec = sum(1 for r in results if r["exec_match"]) + total_type = sum(1 for r in results if r["type_match"]) + total_parse = sum(1 for r in results if r["parse_error"]) + total_err = sum(1 for r in results if r["exec_error"]) + + w = 78 + print("=" * w) + print(f" Model: {self.model or 'dry_run'} N={total}") + print("=" * w) + print(f"{'Op Type':<32} {'N':>4} {'ExecMatch':>10} {'TypeMatch':>10} {'ParseErr':>8} {'ExecErr':>7}") + print("-" * w) + + for op in sorted(by_op): + recs = by_op[op] + n = len(recs) + em = sum(1 for r in recs if r["exec_match"]) + tm = sum(1 for r in recs if r["type_match"]) + pe = sum(1 for r in recs if r["parse_error"]) + ee = sum(1 for r in recs if r["exec_error"]) + mark = "" if em == n else " ✗" + print(f"{op:<32} {n:>4} {em:>4}/{n:<4}{em/n*100:>4.0f}% " + f"{tm:>4}/{n:<4}{tm/n*100:>4.0f}% {pe:>8} {ee:>7}{mark}") + + print("-" * w) + print(f"{'TOTAL':<32} {total:>4} {total_exec:>4}/{total:<4}{total_exec/total*100:>4.0f}% " + f"{total_type:>4}/{total:<4}{total_type/total*100:>4.0f}% " + f"{total_parse:>8} {total_err:>7}") + print("=" * w) + if out_path: + print(f"Results → {out_path}") + + # ── Main evaluate loop ──────────────────────────────────────────────────── + + def evaluate(self, n=None, op_filter=None, out_path=None, seed=0): + records = self._load_dataset(n=n, op_filter=op_filter, seed=seed) + print(f"Loaded {len(records)} records from {self.dataset_dir}") + + # Resume: load existing results + done_ids = set() + results = [] + if out_path and os.path.exists(out_path): + with open(out_path) as f: + results = json.load(f) + done_ids = {r["id"] for r in results} + print(f"Resuming: {len(done_ids)} already evaluated") + + todo = [r for r in records if r.get("id") not in done_ids] + total = len(records) + + def _process(record): + raw = self._call_llm(record) + if self.delay > 0: + time.sleep(self.delay) + return self._evaluate_one(record, raw) + + completed = len(done_ids) + with ThreadPoolExecutor(max_workers=self.workers) as pool: + futures = {pool.submit(_process, r): r for r in todo} + for fut in as_completed(futures): + result = fut.result() + status = "✓" if result["exec_match"] else ("?" if result["parse_error"] else "✗") + with self._lock: + results.append(result) + completed += 1 + print(f" [{completed}/{total}] id={result['id']} op={result['op_type']} {status}", flush=True) + if out_path: + with open(out_path, "w") as f: + json.dump(results, f, indent=2) + + self._report(results, out_path) + return results + + def dry_run(self, op_filter=None): + """Print the prompt for the first matching record, no API call.""" + records = self._load_dataset(n=None, op_filter=op_filter) + if not records: + print("No records found.") + return + r = records[0] + img_path = os.path.join(self.dataset_dir, r["image_path"]) + print("=" * 60) + print("SYSTEM PROMPT:") + print("=" * 60) + print(SYSTEM_PROMPT) + print("=" * 60) + print("USER MESSAGE:") + print("=" * 60) + print(f"Wrong SMILES (mapped): {r['wrong_smiles_mapped']}") + print(f"[image: {img_path} ({os.path.getsize(img_path)//1024} KB)]") + print() + print(f"GT operation: {r['operation']}") + print(f"GT correct: {r['correct_smiles']}") + print("=" * 60) + print("Image exists:", os.path.exists(img_path)) + + +# --------------------------------------------------------------------------- +# CLI +# --------------------------------------------------------------------------- + +def main(): + parser = argparse.ArgumentParser(description="MolEdit benchmark evaluator") + parser.add_argument("--dataset", default="./data/pubchem_dataset") + parser.add_argument("--model", default=None, help="e.g. gpt-4o") + parser.add_argument("--api_base", default="https://api.openai.com/v1") + parser.add_argument("--out", default=None, help="Output JSON path") + parser.add_argument("--n", type=int, default=None, help="Sample size") + parser.add_argument("--op", default=None, help="Filter to one op type") + parser.add_argument("--delay", type=float, default=0.5, help="Seconds between API calls") + parser.add_argument("--workers", type=int, default=4, help="Concurrent API workers") + parser.add_argument("--seed", type=int, default=0) + parser.add_argument("--dry_run", action="store_true", help="Print prompt, no API call") + args = parser.parse_args() + + api_key = os.environ.get("OPENAI_API_KEY") + + ev = BenchmarkEvaluator( + model=args.model, + api_key=api_key, + api_base=args.api_base, + dataset_dir=args.dataset, + delay=args.delay, + workers=args.workers, + ) + + if args.dry_run: + ev.dry_run(op_filter=args.op) + return + + if not args.model or not api_key: + parser.error("--model is required and OPENAI_API_KEY env var must be set (or use --dry_run)") + + out = args.out or os.path.join(args.dataset, "benchmark_results.json") + ev.evaluate(n=args.n, op_filter=args.op, out_path=out, seed=args.seed) + + +if __name__ == "__main__": + main() diff --git a/code/build_dataset_v2.py b/code/build_dataset_v2.py new file mode 100644 index 0000000000000000000000000000000000000000..5bf0df4a22608a4c94da0870eb469670acf52ed9 --- /dev/null +++ b/code/build_dataset_v2.py @@ -0,0 +1,187 @@ +""" +Build MolEdit dataset v2 — balanced, 20 samples per op type (13 types = 260 total). + +Changes from v1: + - target_per_op is a fixed CLI arg (default 20), not derived from n_samples + - Uses a much larger candidate pool to handle rare op types + - Multi-pass: exhausts full pool before giving up on any op type + - Saves to a new output directory (default: ./data/pubchem_dataset_v2) + +Usage: + python build_dataset_v2.py \ + --input /home/dataset-assist-0/usr/lh/mzm/data/pubchem/CID-SMILES.gz.1 \ + --output ./data/pubchem_dataset_v2 \ + --target_per_op 20 \ + --pool 20000 \ + --seed 42 +""" + +import os, sys, json, random, argparse, subprocess, signal +sys.path.insert(0, os.path.dirname(__file__)) + +from rdkit import Chem +from rdkit.Chem import Draw, AllChem +from rdkit import RDLogger +RDLogger.DisableLog("rdApp.*") + +from mol_corrupt import corrupt_molecule, CORRUPTION_TYPES + + +# --------------------------------------------------------------------------- +# Molecule filtering +# --------------------------------------------------------------------------- + +def is_valid(mol, smiles): + if mol is None or "." in smiles: + return False + n = mol.GetNumAtoms() + if n < 5 or n > 60: + return False + if not any(a.GetAtomicNum() == 6 for a in mol.GetAtoms()): + return False + return True + + +# --------------------------------------------------------------------------- +# Streaming sample from gzip file +# --------------------------------------------------------------------------- + +def stream_sample(filepath, pool_size, seed=42): + rng = random.Random(seed) + pool = [] + proc = subprocess.Popen( + ["zcat", filepath], + stdout=subprocess.PIPE, + stderr=subprocess.DEVNULL, + preexec_fn=lambda: signal.signal(signal.SIGPIPE, signal.SIG_DFL), + ) + for raw in proc.stdout: + line = raw.decode("ascii", errors="ignore").strip() + parts = line.split("\t") + if len(parts) >= 2 and parts[0].isdigit(): + pool.append((parts[0], parts[1])) + if len(pool) >= pool_size: + break + proc.kill(); proc.wait() + rng.shuffle(pool) + return pool + + +def render(smiles, path, size=(400, 300)): + mol = Chem.MolFromSmiles(smiles) + if mol is None: + return False + AllChem.Compute2DCoords(mol) + Draw.MolToFile(mol, path, size=size) + return True + + +# --------------------------------------------------------------------------- +# Main builder +# --------------------------------------------------------------------------- + +def build(input_path, output_dir, target_per_op=20, pool_size=20000, seed=42): + img_dir = os.path.join(output_dir, "images") + os.makedirs(img_dir, exist_ok=True) + + print(f"Sampling {pool_size} candidates from {input_path} ...") + raw_pool = stream_sample(input_path, pool_size, seed=seed) + print(f" Got {len(raw_pool)} candidates, filtering ...") + + valid = [] + for cid, smi in raw_pool: + mol = Chem.MolFromSmiles(smi) + if is_valid(mol, smi): + valid.append((cid, Chem.MolToSmiles(mol), mol)) + print(f" {len(valid)} molecules passed filtering") + + collected = {op: 0 for op in CORRUPTION_TYPES} + records = [] + idx = 0 + skipped = 0 + + # Pass through the pool repeatedly until all op types hit target + # or we've done max_passes full sweeps (to avoid infinite loop) + max_passes = 5 + for pass_num in range(1, max_passes + 1): + remaining_ops = [op for op in CORRUPTION_TYPES if collected[op] < target_per_op] + if not remaining_ops: + break + print(f"\nPass {pass_num}: {len(remaining_ops)} op types still need samples") + + random.seed(seed + pass_num) + random.shuffle(valid) + + for cid, canonical, mol in valid: + if not remaining_ops: + break + + for op_type in list(remaining_ops): + if collected[op_type] >= target_per_op: + remaining_ops.remove(op_type) + continue + + result = corrupt_molecule(canonical, op_type=op_type, max_retries=15) + if result is None: + skipped += 1 + continue + + wrong_smi, wrong_smi_mapped, correction = result + item_id = f"{idx:06d}" + img_rel = os.path.join("images", f"{item_id}.png") + abs_img = os.path.join(output_dir, img_rel) + + if not render(canonical, abs_img): + skipped += 1 + continue + + records.append({ + "id": item_id, + "cid": cid, + "correct_smiles": canonical, + "wrong_smiles": wrong_smi, + "wrong_smiles_mapped": wrong_smi_mapped, + "image_path": img_rel, + "operation": correction, + }) + collected[op_type] += 1 + idx += 1 + + if idx % 50 == 0: + print(f" {idx} samples collected ...") + + remaining_ops = [op for op in CORRUPTION_TYPES if collected[op] < target_per_op] + + print("\nOp type coverage:") + for op in CORRUPTION_TYPES: + mark = "✓" if collected[op] >= target_per_op else f"✗ (only {collected[op]})" + print(f" {op:<35} {collected[op]:>4} {mark}") + + json_path = os.path.join(output_dir, "dataset.json") + with open(json_path, "w") as f: + json.dump(records, f, indent=2, ensure_ascii=False) + + print(f"\nDone: {len(records)} samples → {json_path} (skipped {skipped})") + return records + + +# --------------------------------------------------------------------------- +# CLI +# --------------------------------------------------------------------------- + +if __name__ == "__main__": + parser = argparse.ArgumentParser() + parser.add_argument("--input", default="/home/dataset-assist-0/usr/lh/mzm/data/pubchem/CID-SMILES.gz.1") + parser.add_argument("--output", default="./data/pubchem_dataset_v2") + parser.add_argument("--target_per_op", type=int, default=20, help="Samples per op type") + parser.add_argument("--pool", type=int, default=20000, help="Candidate pool size from input file") + parser.add_argument("--seed", type=int, default=42) + args = parser.parse_args() + + build( + input_path=args.input, + output_dir=args.output, + target_per_op=args.target_per_op, + pool_size=args.pool, + seed=args.seed, + ) diff --git a/code/mol_corrupt.py b/code/mol_corrupt.py new file mode 100644 index 0000000000000000000000000000000000000000..a87d94554425f379150bbb5a780be208cb5dd8d1 --- /dev/null +++ b/code/mol_corrupt.py @@ -0,0 +1,544 @@ +""" +Corruption engine using atom map numbers for stable atom identification. + +Each corrupt_* function returns (wrong_rw, raw_correction_with_wrong_rw_indices). +corrupt_molecule() assigns atom map nums to wrong_rw, translates indices → map_nums, +and returns (wrong_smiles, wrong_smiles_mapped, correction_with_maps). + +wrong_smiles : clean SMILES without maps (for display / training input) +wrong_smiles_mapped : SMILES with :[n] map tags (for executor to locate atoms) +correction : operation params use atom_map/anchor_map/atom1_map/atom2_map + instead of raw atom_idx — these survive SMILES round-trips. +""" + +import copy +import random +from rdkit import Chem +from rdkit.Chem import AllChem + +from mol_ops import ( + BOND_TYPE_MAP, BOND_TYPE_NAME, ELEM_TO_NUM, NUM_TO_ELEM, + FUNCTIONAL_GROUPS, + change_atom_element, add_atom, remove_atom, change_charge, + change_bond_order, add_bond, remove_bond, + add_functional_group, remove_functional_group, + flip_chirality, flip_ez, + validate_mol, +) + +CORRUPTION_TYPES = [ + "change_atom_element", + "add_atom", + "remove_atom", + "change_charge", + "change_bond_order", + "add_bond", + "remove_bond", + "add_functional_group", + "remove_functional_group", + "flip_chirality", + "flip_ez", + "move_substituent", + "swap_substituents", +] + + +# --------------------------------------------------------------------------- +# Helpers +# --------------------------------------------------------------------------- + +def _random_other_elem(current_elem): + candidates = [e for e in ("C", "N", "O", "S") if e != current_elem] + return random.choice(candidates) + + +def _has_free_valence(atom): + try: + return atom.GetNumImplicitHs() > 0 + except Exception: + return False + + +def _assign_atom_maps(rw): + """Assign map_num = idx+1 to every atom in rw (in-place).""" + for atom in rw.GetAtoms(): + atom.SetAtomMapNum(atom.GetIdx() + 1) + + +def _strip_atom_maps(rw): + """Return a copy of rw with all atom maps removed.""" + c = copy.deepcopy(rw) + for atom in c.GetAtoms(): + atom.SetAtomMapNum(0) + return c + + +def _translate_correction(wrong_rw, raw): + """ + Translate a raw correction (atom_idx → map_num) for stable cross-SMILES use. + raw = {'type': ..., 'params': {atom_idx: X, ...}, 'description': ...} + Returns new correction dict with map_num-based params. + """ + params = {} + for k, v in raw["params"].items(): + if k == "atom_idx": + params["atom_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "anchor_idx": + params["anchor_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "atom_idx1": + params["atom1_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "atom_idx2": + params["atom2_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "substituent_idx": + params["substituent_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "from_idx": + params["from_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "to_idx": + params["to_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "ring_idx1": + params["ring1_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + elif k == "ring_idx2": + params["ring2_map"] = wrong_rw.GetAtomWithIdx(v).GetAtomMapNum() + else: + params[k] = v + return {"type": raw["type"], "params": params, "description": raw["description"]} + + +# --------------------------------------------------------------------------- +# Individual corruption functions +# Each returns (wrong_rw, raw_correction) or None +# raw_correction uses atom indices in wrong_rw space +# --------------------------------------------------------------------------- + +def corrupt_change_atom_element(mol): + rw = Chem.RWMol(mol) + atoms = [a for a in rw.GetAtoms() + if a.GetAtomicNum() > 1 and not a.GetIsAromatic()] + if not atoms: + return None + atom = random.choice(atoms) + idx = atom.GetIdx() + old_elem = NUM_TO_ELEM.get(atom.GetAtomicNum(), "C") + new_elem = _random_other_elem(old_elem) + result = change_atom_element(rw, atom_idx=idx, to_elem=new_elem) + if result is None: + return None + return result, { + "type": "change_atom_element", + "params": {"atom_idx": idx, "from_elem": new_elem, "to_elem": old_elem}, + "description": f"Change atom {idx} from {new_elem} back to {old_elem}", + } + + +def corrupt_add_atom(mol): + rw = Chem.RWMol(mol) + atoms = [a for a in rw.GetAtoms() if _has_free_valence(a)] + if not atoms: + return None + anchor = random.choice(atoms) + new_elem = random.choice(["C", "N", "O"]) + result = add_atom(rw, anchor_idx=anchor.GetIdx(), new_elem=new_elem) + if result is None: + return None + new_idx = result.GetNumAtoms() - 1 + return result, { + "type": "remove_atom", + "params": {"atom_idx": new_idx, "elem": new_elem}, + "description": f"Remove extra {new_elem} atom (added by corruption)", + } + + +def corrupt_remove_atom(mol): + rw = Chem.RWMol(mol) + terminals = [a for a in rw.GetAtoms() + if a.GetDegree() == 1 and not a.IsInRing() and a.GetAtomicNum() > 1] + if not terminals: + return None + atom = random.choice(terminals) + idx = atom.GetIdx() + elem = NUM_TO_ELEM.get(atom.GetAtomicNum(), "C") + neighbor = atom.GetNeighbors()[0] + anchor_idx = neighbor.GetIdx() + bond = rw.GetBondBetweenAtoms(idx, anchor_idx) + bond_type = BOND_TYPE_NAME.get(bond.GetBondType(), "SINGLE") + + result = remove_atom(rw, atom_idx=idx) + if result is None: + return None + # Atoms after idx shift down by 1 + adj_anchor = anchor_idx if anchor_idx < idx else anchor_idx - 1 + return result, { + "type": "add_atom", + "params": {"anchor_idx": adj_anchor, "new_elem": elem, "bond_type": bond_type}, + "description": f"Add missing {elem} atom back to anchor", + } + + +def corrupt_change_charge(mol): + rw = Chem.RWMol(mol) + # Only corrupt atoms that currently have charge 0 (reversible: 0→±1, then ±1→0 is safe) + candidates = [a for a in rw.GetAtoms() + if a.GetAtomicNum() in (7, 8) and not a.GetIsAromatic() + and a.GetFormalCharge() == 0 and a.GetNumImplicitHs() == 0] + if not candidates: + return None + atom = random.choice(candidates) + idx = atom.GetIdx() + old_charge = 0 + new_charge = random.choice([-1, 1]) + result = change_charge(rw, atom_idx=idx, to_charge=new_charge) + if result is None: + return None + return result, { + "type": "change_charge", + "params": {"atom_idx": idx, "from_charge": new_charge, "to_charge": old_charge}, + "description": f"Change charge at atom back from {new_charge:+d} to {old_charge:+d}", + } + + +def corrupt_change_bond_order(mol): + rw = Chem.RWMol(mol) + bonds = [b for b in rw.GetBonds() + if b.GetBondType() in (Chem.BondType.SINGLE, Chem.BondType.DOUBLE) + and not b.GetIsAromatic()] + if not bonds: + return None + bond = random.choice(bonds) + idx1, idx2 = bond.GetBeginAtomIdx(), bond.GetEndAtomIdx() + old_order = BOND_TYPE_NAME[bond.GetBondType()] + new_order = "DOUBLE" if old_order == "SINGLE" else "SINGLE" + result = change_bond_order(rw, atom_idx1=idx1, atom_idx2=idx2, to_order=new_order) + if result is None: + return None + return result, { + "type": "change_bond_order", + "params": {"atom_idx1": idx1, "atom_idx2": idx2, + "from_order": new_order, "to_order": old_order}, + "description": f"Change bond ({idx1}-{idx2}) from {new_order} back to {old_order}", + } + + +def corrupt_add_bond(mol): + rw = Chem.RWMol(mol) + n = rw.GetNumAtoms() + if n < 4: + return None + pairs = [(i, j) for i in range(n) for j in range(i + 2, n) + if rw.GetBondBetweenAtoms(i, j) is None] + if not pairs: + return None + i, j = random.choice(pairs) + result = add_bond(rw, atom_idx1=i, atom_idx2=j, bond_type="SINGLE") + if result is None: + return None + return result, { + "type": "remove_bond", + "params": {"atom_idx1": i, "atom_idx2": j}, + "description": f"Remove spurious bond between atoms {i} and {j}", + } + + +def corrupt_remove_bond(mol): + rw = Chem.RWMol(mol) + bonds = [b for b in rw.GetBonds() if not b.IsInRing()] + if not bonds: + return None + bond = random.choice(bonds) + idx1, idx2 = bond.GetBeginAtomIdx(), bond.GetEndAtomIdx() + order = BOND_TYPE_NAME.get(bond.GetBondType(), "SINGLE") + result = remove_bond(rw, atom_idx1=idx1, atom_idx2=idx2) + if result is None: + return None + return result, { + "type": "add_bond", + "params": {"atom_idx1": idx1, "atom_idx2": idx2, "bond_type": order}, + "description": f"Add back {order} bond between atoms {idx1} and {idx2}", + } + + +def corrupt_add_functional_group(mol): + rw = Chem.RWMol(mol) + atoms = [a for a in rw.GetAtoms() if a.GetAtomicNum() == 6] + if not atoms: + return None + anchor = random.choice(atoms) + group = random.choice(["OH", "NH2", "F", "Cl", "Br", "CH3"]) + result = add_functional_group(rw, anchor_idx=anchor.GetIdx(), group_name=group) + if result is None: + return None + # anchor idx unchanged after adding group atoms at the end + return result, { + "type": "remove_functional_group", + "params": {"anchor_idx": anchor.GetIdx(), "group_name": group}, + "description": f"Remove extra -{group} group", + } + + +def corrupt_remove_functional_group(mol): + rw = Chem.RWMol(mol) + for group in ("OH", "NH2", "F", "Cl", "Br", "CH3"): + for atom in rw.GetAtoms(): + if atom.GetAtomicNum() != 6: + continue + test = Chem.RWMol(mol) + result, removed = remove_functional_group(test, atom.GetIdx(), group) + if result is None: + continue + removed_idx = removed[0] + anchor_in_mol = atom.GetIdx() + # After removing atom at removed_idx, anchor shifts if removed_idx < anchor + adj_anchor = anchor_in_mol if removed_idx > anchor_in_mol else anchor_in_mol - 1 + return result, { + "type": "add_functional_group", + "params": {"anchor_idx": adj_anchor, "group_name": group}, + "description": f"Add -{group} back to anchor atom", + } + return None + + +def corrupt_flip_chirality(mol): + rw = Chem.RWMol(mol) + Chem.AssignStereochemistry(rw, cleanIt=True, force=True) + chiral = [a for a in rw.GetAtoms() + if a.GetChiralTag() != Chem.ChiralType.CHI_UNSPECIFIED] + if not chiral: + return None + atom = random.choice(chiral) + idx = atom.GetIdx() + result = flip_chirality(rw, atom_idx=idx) + if result is None: + return None + return result, { + "type": "flip_chirality", + "params": {"atom_idx": idx}, + "description": f"Flip chirality back at atom {idx}", + } + + +def corrupt_flip_ez(mol): + """SMILES-level; returns (wrong_smi, raw_correction) directly.""" + smi = Chem.MolToSmiles(mol, isomericSmiles=True) + if "/" not in smi and "\\" not in smi: + return None + wrong_smi = flip_ez(smi) + if wrong_smi is None or wrong_smi == smi: + return None + return wrong_smi, { + "type": "flip_ez", + "params": {}, + "description": "Flip E/Z configuration back", + } + + +def corrupt_move_substituent(mol): + """ + Move a non-ring substituent from one ring atom to a different ring atom + in the same ring (e.g. ortho→meta shift on benzene). + Operates in Kekulé form to avoid aromatic bond issues. + Correction: MoveSubstituent back. + """ + rw = Chem.RWMol(mol) + try: + Chem.Kekulize(rw, clearAromaticFlags=True) + except Exception: + return None + + ri = rw.GetRingInfo() + rings = [set(r) for r in ri.AtomRings() if len(r) >= 5] + if not rings: + return None + + # Build all (from_idx, sub_idx, to_idx) triples and shuffle + triples = [] + for ring in rings: + ring_list = list(ring) + for from_idx in ring_list: + atom = rw.GetAtomWithIdx(from_idx) + subs = [nb for nb in atom.GetNeighbors() + if nb.GetIdx() not in ring and nb.GetAtomicNum() > 1] + for sub in subs: + sub_idx = sub.GetIdx() + for to_idx in ring_list: + if to_idx != from_idx and rw.GetBondBetweenAtoms(to_idx, sub_idx) is None: + triples.append((from_idx, sub_idx, to_idx)) + random.shuffle(triples) + + for from_idx, sub_idx, to_idx in triples: + rw2 = Chem.RWMol(copy.deepcopy(rw)) + rw2.RemoveBond(from_idx, sub_idx) + rw2.AddBond(to_idx, sub_idx, Chem.BondType.SINGLE) + if not validate_mol(rw2): + continue + # Check it actually changed the molecule + wrong_smi = Chem.MolToSmiles(rw2) + orig_smi = Chem.MolToSmiles(mol) + if wrong_smi == orig_smi: + continue + return rw2, { + "type": "move_substituent", + "params": { + "substituent_idx": sub_idx, + "from_idx": to_idx, # correction reverses: from=to, to=from + "to_idx": from_idx, + }, + "description": f"Move substituent {sub_idx} back from ring atom {to_idx} to {from_idx}", + } + return None + + +def corrupt_swap_substituents(mol): + """ + Swap the non-ring substituents of two ring atoms in the same ring. + Operates in Kekulé form to avoid aromatic bond issues. + Correction: SwapSubstituents back (same action). + """ + rw = Chem.RWMol(mol) + try: + Chem.Kekulize(rw, clearAromaticFlags=True) + except Exception: + return None + + ri = rw.GetRingInfo() + rings = [list(r) for r in ri.AtomRings() if len(r) >= 5] + if not rings: + return None + + random.shuffle(rings) + for ring in rings: + ring_set = set(ring) + substituted = [] + for idx in ring: + subs = [nb.GetIdx() for nb in rw.GetAtomWithIdx(idx).GetNeighbors() + if nb.GetIdx() not in ring_set and nb.GetAtomicNum() > 1] + if subs: + substituted.append((idx, subs)) + if len(substituted) < 2: + continue + + random.shuffle(substituted) + (idx1, subs1), (idx2, subs2) = substituted[0], substituted[1] + + def bonds_to(center, sub_list): + return [(s, rw.GetBondBetweenAtoms(center, s).GetBondType()) for s in sub_list] + + b1 = bonds_to(idx1, subs1) + b2 = bonds_to(idx2, subs2) + + if any(rw.GetBondBetweenAtoms(idx2, s) is not None for s, _ in b1): + continue + if any(rw.GetBondBetweenAtoms(idx1, s) is not None for s, _ in b2): + continue + + rw2 = Chem.RWMol(copy.deepcopy(rw)) + for s, _ in b1: + rw2.RemoveBond(idx1, s) + for s, _ in b2: + rw2.RemoveBond(idx2, s) + for s, bt in b1: + rw2.AddBond(idx2, s, Chem.BondType.SINGLE) + for s, bt in b2: + rw2.AddBond(idx1, s, Chem.BondType.SINGLE) + + if not validate_mol(rw2): + continue + return rw2, { + "type": "swap_substituents", + "params": { + "ring_idx1": idx1, + "ring_idx2": idx2, + }, + "description": f"Swap substituents back between ring atoms {idx1} and {idx2}", + } + return None + + +CORRUPT_FUNCS = { + "change_atom_element": corrupt_change_atom_element, + "add_atom": corrupt_add_atom, + "remove_atom": corrupt_remove_atom, + "change_charge": corrupt_change_charge, + "change_bond_order": corrupt_change_bond_order, + "add_bond": corrupt_add_bond, + "remove_bond": corrupt_remove_bond, + "add_functional_group": corrupt_add_functional_group, + "remove_functional_group": corrupt_remove_functional_group, + "flip_chirality": corrupt_flip_chirality, + "flip_ez": corrupt_flip_ez, + "move_substituent": corrupt_move_substituent, + "swap_substituents": corrupt_swap_substituents, +} + + +# --------------------------------------------------------------------------- +# Main API +# --------------------------------------------------------------------------- + +def corrupt_molecule(smiles, op_type=None, max_retries=20): + """ + Returns (wrong_smiles, wrong_smiles_mapped, correction) or None. + + wrong_smiles — clean SMILES (no atom maps), the erroneous input + wrong_smiles_mapped — SMILES with :[n] atom map tags for executor use + correction — dict with type, params (map_num-based), description + """ + mol = Chem.MolFromSmiles(smiles) + if mol is None: + return None + + for _ in range(max_retries): + chosen_type = op_type or random.choice(CORRUPTION_TYPES) + func = CORRUPT_FUNCS[chosen_type] + raw = func(mol) + if raw is None: + continue + + # flip_ez is SMILES-level — handle separately + if chosen_type == "flip_ez": + wrong_smi, raw_correction = raw + if wrong_smi == smiles: + continue + wrong_mol = Chem.MolFromSmiles(wrong_smi) + if wrong_mol is None: + continue + wrong_rw = Chem.RWMol(wrong_mol) + _assign_atom_maps(wrong_rw) + wrong_smiles_mapped = Chem.MolToSmiles(wrong_rw) + correction = {"type": "flip_ez", "params": {}, + "description": raw_correction["description"]} + return wrong_smi, wrong_smiles_mapped, correction + + wrong_rw, raw_correction = raw + if not validate_mol(wrong_rw): + continue + + # Assign atom map numbers to wrong_rw (map_num = idx + 1) + _assign_atom_maps(wrong_rw) + + # Translate index-based params → map-num-based params + try: + correction = _translate_correction(wrong_rw, raw_correction) + except (IndexError, RuntimeError): + continue + + # Generate clean wrong SMILES (no maps) + wrong_smiles = Chem.MolToSmiles(_strip_atom_maps(wrong_rw)) + if wrong_smiles == smiles: + continue + + wrong_smiles_mapped = Chem.MolToSmiles(wrong_rw) + + # ── Verify round-trip before accepting ────────────────────────────── + from action_executor import ActionExecutor as _AE + from validate_with_executor import translate_operation + try: + action = translate_operation(correction) + restored = _AE().execute(wrong_smiles_mapped, action) + except Exception: + continue + restored_mol = Chem.MolFromSmiles(restored) if restored else None + if restored_mol is None or Chem.MolToSmiles(restored_mol) != smiles: + continue # bad sample — discard and retry + + return wrong_smiles, wrong_smiles_mapped, correction + + return None diff --git a/code/mol_ops.py b/code/mol_ops.py new file mode 100644 index 0000000000000000000000000000000000000000..fbf86046f1e66ced01af361d1375890b7b075a65 --- /dev/null +++ b/code/mol_ops.py @@ -0,0 +1,287 @@ +""" +Core molecular editing operations using RDKit's RWMol API. + +Each operation takes an RWMol and parameters, returns the modified RWMol. +Each has a forward (corruption) and inverse (correction) form. +""" + +import copy +from rdkit import Chem +from rdkit.Chem import AllChem, rdmolops + + +BOND_TYPE_MAP = { + "SINGLE": Chem.BondType.SINGLE, + "DOUBLE": Chem.BondType.DOUBLE, + "TRIPLE": Chem.BondType.TRIPLE, + "AROMATIC": Chem.BondType.AROMATIC, +} + +BOND_TYPE_NAME = {v: k for k, v in BOND_TYPE_MAP.items()} + +ELEM_TO_NUM = { + "C": 6, "N": 7, "O": 8, "S": 16, "P": 15, "F": 9, + "Cl": 17, "Br": 35, "I": 53, "B": 5, "Si": 14, "Se": 34, +} + +NUM_TO_ELEM = {v: k for k, v in ELEM_TO_NUM.items()} + +FUNCTIONAL_GROUPS = { + "OH": "[OH]", + "NH2": "[NH2]", + "F": "[F]", + "Cl": "[Cl]", + "Br": "[Br]", + "CH3": "[CH3]", + "NO2": "[N+](=O)[O-]", + "COOH": "C(=O)[OH]", + "CHO": "[CH]=O", +} + + +def validate_mol(mol): + if mol is None: + return False + try: + Chem.SanitizeMol(mol) + return True + except Exception: + return False + + +def safe_apply(func): + """Decorator: returns None if the operation produces an invalid molecule.""" + def wrapper(mol, **kwargs): + rw = copy.deepcopy(mol) + try: + result = func(rw, **kwargs) + if result is None: + return None + if not validate_mol(result): + return None + return result + except Exception: + return None + return wrapper + + +# --------------------------------------------------------------------------- +# 1. change_atom_element +# --------------------------------------------------------------------------- +@safe_apply +def change_atom_element(mol, atom_idx, to_elem): + atom = mol.GetAtomWithIdx(atom_idx) + atom.SetAtomicNum(ELEM_TO_NUM[to_elem]) + atom.SetNoImplicit(False) + atom.UpdatePropertyCache(strict=False) + return mol + + +# --------------------------------------------------------------------------- +# 2. add_atom — adds a new atom bonded to anchor +# --------------------------------------------------------------------------- +@safe_apply +def add_atom(mol, anchor_idx, new_elem, bond_type="SINGLE"): + new_idx = mol.AddAtom(Chem.Atom(ELEM_TO_NUM[new_elem])) + mol.AddBond(anchor_idx, new_idx, BOND_TYPE_MAP[bond_type]) + return mol + + +# --------------------------------------------------------------------------- +# 3. remove_atom +# --------------------------------------------------------------------------- +@safe_apply +def remove_atom(mol, atom_idx): + mol.RemoveAtom(atom_idx) + return mol + + +# --------------------------------------------------------------------------- +# 4. change_charge +# --------------------------------------------------------------------------- +@safe_apply +def change_charge(mol, atom_idx, to_charge): + atom = mol.GetAtomWithIdx(atom_idx) + atom.SetFormalCharge(to_charge) + atom.UpdatePropertyCache(strict=False) + return mol + + +# --------------------------------------------------------------------------- +# 5. change_bond_order +# --------------------------------------------------------------------------- +@safe_apply +def change_bond_order(mol, atom_idx1, atom_idx2, to_order): + bond = mol.GetBondBetweenAtoms(atom_idx1, atom_idx2) + if bond is None: + return None + bond.SetBondType(BOND_TYPE_MAP[to_order]) + return mol + + +# --------------------------------------------------------------------------- +# 6. add_bond +# --------------------------------------------------------------------------- +@safe_apply +def add_bond(mol, atom_idx1, atom_idx2, bond_type="SINGLE"): + existing = mol.GetBondBetweenAtoms(atom_idx1, atom_idx2) + if existing is not None: + return None + mol.AddBond(atom_idx1, atom_idx2, BOND_TYPE_MAP[bond_type]) + return mol + + +# --------------------------------------------------------------------------- +# 7. remove_bond +# --------------------------------------------------------------------------- +@safe_apply +def remove_bond(mol, atom_idx1, atom_idx2): + bond = mol.GetBondBetweenAtoms(atom_idx1, atom_idx2) + if bond is None: + return None + mol.RemoveBond(atom_idx1, atom_idx2) + return mol + + +# --------------------------------------------------------------------------- +# 8. add_functional_group +# --------------------------------------------------------------------------- +@safe_apply +def add_functional_group(mol, anchor_idx, group_name): + group_smi = FUNCTIONAL_GROUPS.get(group_name) + if group_smi is None: + return None + group_mol = Chem.MolFromSmiles(group_smi) + if group_mol is None: + return None + + combo = Chem.RWMol(rdmolops.CombineMols(mol, group_mol)) + old_n = mol.GetNumAtoms() + anchor = combo.GetAtomWithIdx(anchor_idx) + anchor.SetNumExplicitHs(0) + anchor.SetNoImplicit(False) + anchor.SetNumRadicalElectrons(0) + combo.AddBond(anchor_idx, old_n, Chem.BondType.SINGLE) + return combo + + +# --------------------------------------------------------------------------- +# 9. remove_functional_group (removes a terminal substituent at anchor) +# --------------------------------------------------------------------------- +def remove_functional_group(mol, anchor_idx, group_name): + """Remove atoms belonging to a terminal functional group attached at anchor_idx. + Returns (new_mol, removed_atom_indices) or (None, []).""" + rw = copy.deepcopy(mol) + anchor = rw.GetAtomWithIdx(anchor_idx) + neighbors = [n for n in anchor.GetNeighbors()] + + if group_name in ("F", "Cl", "Br"): + target_num = ELEM_TO_NUM.get(group_name) + for n in neighbors: + if n.GetAtomicNum() == target_num and n.GetDegree() == 1: + idx = n.GetIdx() + rw.RemoveAtom(idx) + try: + Chem.SanitizeMol(rw) + return rw, [idx] + except Exception: + return None, [] + return None, [] + + if group_name == "OH": + for n in neighbors: + if n.GetAtomicNum() == 8 and n.GetDegree() == 1: + bond = rw.GetBondBetweenAtoms(anchor_idx, n.GetIdx()) + if bond and bond.GetBondType() == Chem.BondType.SINGLE: + idx = n.GetIdx() + rw.RemoveAtom(idx) + try: + Chem.SanitizeMol(rw) + return rw, [idx] + except Exception: + return None, [] + return None, [] + + if group_name == "NH2": + for n in neighbors: + if n.GetAtomicNum() == 7 and n.GetDegree() == 1: + idx = n.GetIdx() + rw.RemoveAtom(idx) + try: + Chem.SanitizeMol(rw) + return rw, [idx] + except Exception: + return None, [] + return None, [] + + if group_name == "CH3": + for n in neighbors: + if n.GetAtomicNum() == 6 and n.GetDegree() == 1 and n.GetTotalNumHs() == 3: + idx = n.GetIdx() + rw.RemoveAtom(idx) + try: + Chem.SanitizeMol(rw) + return rw, [idx] + except Exception: + return None, [] + return None, [] + + return None, [] + + +# --------------------------------------------------------------------------- +# 10. flip_chirality +# --------------------------------------------------------------------------- +@safe_apply +def flip_chirality(mol, atom_idx): + atom = mol.GetAtomWithIdx(atom_idx) + chi = atom.GetChiralTag() + if chi == Chem.ChiralType.CHI_TETRAHEDRAL_CW: + atom.SetChiralTag(Chem.ChiralType.CHI_TETRAHEDRAL_CCW) + elif chi == Chem.ChiralType.CHI_TETRAHEDRAL_CCW: + atom.SetChiralTag(Chem.ChiralType.CHI_TETRAHEDRAL_CW) + else: + return None + return mol + + +# --------------------------------------------------------------------------- +# 11. flip_ez — flip E/Z via SMILES-level slash inversion +# --------------------------------------------------------------------------- +def flip_ez(smiles): + """Flip E/Z by inverting the first /-slash in the SMILES. + Works at the SMILES string level since RDKit mol-level stereo + doesn't round-trip reliably through MolToSmiles.""" + if "/" not in smiles and "\\" not in smiles: + return None + chars = list(smiles) + for i, c in enumerate(chars): + if c == "/": + chars[i] = "\\" + break + elif c == "\\": + chars[i] = "/" + break + new_smi = "".join(chars) + mol = Chem.MolFromSmiles(new_smi) + if mol is None: + return None + return Chem.MolToSmiles(mol, isomericSmiles=True) + + +# --------------------------------------------------------------------------- +# Registry: maps operation type name → apply function +# --------------------------------------------------------------------------- +OP_REGISTRY = { + "change_atom_element": change_atom_element, + "add_atom": add_atom, + "remove_atom": remove_atom, + "change_charge": change_charge, + "change_bond_order": change_bond_order, + "add_bond": add_bond, + "remove_bond": remove_bond, + "add_functional_group": add_functional_group, + "remove_functional_group": lambda mol, **kw: remove_functional_group(mol, **kw)[0], + "flip_chirality": flip_chirality, + "flip_ez": flip_ez, +} diff --git a/code/validate_with_executor.py b/code/validate_with_executor.py new file mode 100644 index 0000000000000000000000000000000000000000..e7523092a41cd0211f5e1a2f95f7c5507d977c37 --- /dev/null +++ b/code/validate_with_executor.py @@ -0,0 +1,263 @@ +""" +Validate pubchem_dataset records using ActionExecutor. + +Translates old-format operation dicts (raw atom_idx params) to the new +ActionExecutor JSON protocol, then checks that executing the action on +wrong_smiles reproduces correct_smiles. + +Usage: + python validate_with_executor.py [--dataset ./data/pubchem_dataset] [--verbose] +""" + +import os, sys, json, argparse +from collections import Counter, defaultdict +sys.path.insert(0, os.path.dirname(__file__)) + +from rdkit import Chem, RDLogger +RDLogger.DisableLog("rdApp.*") + +from action_executor import ActionExecutor, ActionError + + +# --------------------------------------------------------------------------- +# Old-format → ActionExecutor JSON translation +# --------------------------------------------------------------------------- + +def translate_operation(op: dict) -> dict: + """ + Convert a mol_corrupt.py correction dict to an ActionExecutor action dict. + + New format (atom_map / anchor_map / atom1_map / atom2_map) uses map_num refs. + Old format (atom_idx / anchor_idx / atom_idx1 / atom_idx2) uses idx refs. + Both are handled transparently. + """ + old_type = op["type"] + params = op.get("params", {}) + + # Determine ref style: map-num (new) or raw idx (old) + has_maps = any(k in params for k in ("atom_map", "anchor_map", "atom1_map", "atom2_map")) + + def atom_ref(map_key, idx_key): + if has_maps and map_key in params: + return {"map_num": params[map_key]} + return {"idx": params[idx_key]} + + def bond_ref(map1, idx1, map2, idx2): + return {"atom1": atom_ref(map1, idx1), "atom2": atom_ref(map2, idx2)} + + if old_type == "change_atom_element": + return { + "type": "ChangeAtom", + "atom": atom_ref("atom_map", "atom_idx"), + "element": params["to_elem"], + } + + if old_type == "change_charge": + return { + "type": "ChangeAtom", + "atom": atom_ref("atom_map", "atom_idx"), + "charge": params["to_charge"], + } + + if old_type == "add_atom": + return { + "type": "AddAtom", + "anchor": atom_ref("anchor_map", "anchor_idx"), + "element": params["new_elem"], + "bond_order": params.get("bond_type", "SINGLE"), + } + + if old_type == "remove_atom": + return { + "type": "RemoveAtom", + "atom": atom_ref("atom_map", "atom_idx"), + } + + if old_type == "change_bond_order": + return { + "type": "ChangeBond", + "bond": bond_ref("atom1_map", "atom_idx1", "atom2_map", "atom_idx2"), + "order": params["to_order"], + } + + if old_type == "add_bond": + return { + "type": "AddBond", + "bond": bond_ref("atom1_map", "atom_idx1", "atom2_map", "atom_idx2"), + "order": params.get("bond_type", "SINGLE"), + } + + if old_type == "remove_bond": + return { + "type": "RemoveBond", + "bond": bond_ref("atom1_map", "atom_idx1", "atom2_map", "atom_idx2"), + } + + if old_type == "add_functional_group": + return { + "type": "AddGroup", + "anchor": atom_ref("anchor_map", "anchor_idx"), + "group": params["group_name"], + } + + if old_type == "remove_functional_group": + return { + "type": "RemoveGroup", + "anchor": atom_ref("anchor_map", "anchor_idx"), + "group": params["group_name"], + } + + if old_type == "flip_chirality": + return { + "type": "FlipChirality", + "atom": atom_ref("atom_map", "atom_idx"), + } + + if old_type == "flip_ez": + # SMILES-level op — find the double bond automatically + return {"type": "FlipEZ"} + + if old_type == "move_substituent": + return { + "type": "MoveSubstituent", + "substituent": {"map_num": params["substituent_map"]}, + "from_atom": {"map_num": params["from_map"]}, + "to_atom": {"map_num": params["to_map"]}, + } + + if old_type == "swap_substituents": + return { + "type": "SwapSubstituents", + "atom1": {"map_num": params["ring1_map"]}, + "atom2": {"map_num": params["ring2_map"]}, + } + + raise ValueError(f"Unhandled old type: {old_type!r}") + + +# --------------------------------------------------------------------------- +# Validation +# --------------------------------------------------------------------------- + +def validate(records, verbose=False): + ex = ActionExecutor() + results = defaultdict(lambda: {"pass": 0, "fail": 0, "error": 0}) + failures = [] + + for r in records: + op_type = r["operation"]["type"] + # Prefer mapped SMILES (new format) so map_num refs work correctly + wrong = r.get("wrong_smiles_mapped") or r.get("wrong_smiles", "") + correct = r["correct_smiles"] + + try: + action = translate_operation(r["operation"]) + except Exception as e: + results[op_type]["error"] += 1 + failures.append({"id": r.get("id"), "op": op_type, "kind": "translate_error", "msg": str(e)}) + continue + + try: + restored = ex.execute(wrong, action) + except ActionError as e: + results[op_type]["error"] += 1 + failures.append({ + "id": r.get("id"), "op": op_type, "kind": "executor_error", + "msg": str(e), "wrong": wrong, "action": action, + }) + continue + except Exception as e: + results[op_type]["error"] += 1 + failures.append({ + "id": r.get("id"), "op": op_type, "kind": "unexpected_error", + "msg": str(e), "wrong": wrong, + }) + continue + + # Canonicalize both for fair comparison + mol_r = Chem.MolFromSmiles(restored) if restored else None + mol_c = Chem.MolFromSmiles(correct) + canon_r = Chem.MolToSmiles(mol_r) if mol_r else None + canon_c = Chem.MolToSmiles(mol_c) if mol_c else None + + if canon_r == canon_c: + results[op_type]["pass"] += 1 + else: + results[op_type]["fail"] += 1 + failures.append({ + "id": r.get("id"), "op": op_type, "kind": "mismatch", + "wrong": wrong, "expected": correct, "got": restored, + "action": action, + }) + + return results, failures + + +# --------------------------------------------------------------------------- +# Report +# --------------------------------------------------------------------------- + +def report(results, failures, verbose=False): + print("=" * 76) + print(f"{'Op Type':<35} {'Total':>6} {'Pass':>5} {'Fail':>5} {'Error':>6} {'Rate':>6}") + print("-" * 76) + + total_p = total_f = total_e = 0 + for op in sorted(results): + r = results[op] + p, f, e = r["pass"], r["fail"], r["error"] + n = p + f + e + rate = p / n * 100 if n else 0 + mark = "" if (f + e) == 0 else " ✗" + print(f"{op:<35} {n:>6} {p:>5} {f:>5} {e:>6} {rate:>5.0f}%{mark}") + total_p += p; total_f += f; total_e += e + + total = total_p + total_f + total_e + print("-" * 76) + rate = total_p / total * 100 if total else 0 + print(f"{'TOTAL':<35} {total:>6} {total_p:>5} {total_f:>5} {total_e:>6} {rate:>5.0f}%") + print("=" * 76) + + if failures: + show = failures if verbose else failures[:5] + print(f"\n--- {len(failures)} failure(s){' (showing first 5)' if not verbose and len(failures) > 5 else ''} ---") + for fl in show: + print(f"\n [{fl['op']}] id={fl.get('id')} kind={fl['kind']}") + if fl["kind"] == "mismatch": + print(f" wrong : {fl['wrong']}") + print(f" action : {fl['action']}") + print(f" expected : {fl['expected']}") + print(f" got : {fl['got']}") + elif fl["kind"] in ("executor_error", "translate_error", "unexpected_error"): + print(f" wrong : {fl.get('wrong', '')}") + print(f" action : {fl.get('action', '')}") + print(f" error : {fl['msg']}") + else: + print("\n✓ All records pass validation.") + + +def main(): + parser = argparse.ArgumentParser() + parser.add_argument("--dataset", default="./data/pubchem_dataset") + parser.add_argument("--verbose", action="store_true", help="Show all failures") + args = parser.parse_args() + + for name in ("dataset.json", "roundtrip_test.json"): + p = os.path.join(args.dataset, name) + if os.path.exists(p): + json_path = p + break + else: + print(f"No dataset JSON found in {args.dataset}") + sys.exit(1) + + with open(json_path) as f: + records = json.load(f) + print(f"Loaded {len(records)} records from {json_path}\n") + + results, failures = validate(records, verbose=args.verbose) + report(results, failures, verbose=args.verbose) + + +if __name__ == "__main__": + main() diff --git a/data/benchmark_results_claude_opus46.json b/data/benchmark_results_claude_opus46.json new file mode 100644 index 0000000000000000000000000000000000000000..a1e1d09d370268d53109269a44cbcdc83e8cef55 --- /dev/null +++ b/data/benchmark_results_claude_opus46.json @@ -0,0 +1,5198 @@ +[ + { + "id": "000004", + "op_type": "add_bond", + "image_path": "images/000004.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:12]1.[OH2:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the image, I see a benzene ring with a tert-butyl group and two OH groups on the ring (a catechol-like arrangement with OH groups on adjacent carbons).\n\nThe wrong SMILES has: tert-butyl group on the ring, one OH at position :8, and a separate water molecule (OH2 at :11).\n\nThe correct molecule should have two OH groups on the ring (no water molecule). The water molecule's oxygen (:11) needs to be added as an OH group to the ring. Looking at the image, the second OH is on the carbon adjacent to the existing OH, which corresponds to atom :10.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 10}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 10 + }, + "group": "OH" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1.O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000005", + "op_type": "remove_functional_group", + "image_path": "images/000005.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:13])[c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the image, I see a benzene ring with a tert-butyl group and two OH groups. The correct molecule is 4-tert-butylcatechol (two adjacent OH groups) without any fluorine atom.\n\nThe wrong SMILES has a fluorine atom at position 13 (on atom 7) that shouldn't be there. In the image, there's no fluorine \u2014 just the tert-butyl group and two hydroxyl groups on the ring.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000006", + "op_type": "add_functional_group", + "image_path": "images/000006.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the image, I see a benzene ring with a tert-butyl group and TWO hydroxyl (OH) groups on the ring (at adjacent positions, forming a catechol-like arrangement).\n\nThe wrong SMILES has only one OH group (on atom 9). The correct molecule has an additional OH group. Looking at the image, the second OH is on the carbon between the tert-butyl-bearing carbon and the existing OH-bearing carbon \u2014 that would be atom 11.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 11}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 11 + }, + "group": "OH" + }, + "restored_smiles": "CC(C)(C)c1cccc(O)c1O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000009", + "op_type": "change_atom_element", + "image_path": "images/000009.png", + "wrong_smiles_mapped": "[NH2:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "Looking at the image, the correct molecule is 3-hydroxyphenylalanine (m-tyrosine): an amino acid with a carbon backbone bearing an NH2 group and a COOH group, connected via a CH2 to a phenyl ring with an OH substituent.\n\nIn the wrong SMILES, the NH2 and the COOH are both directly attached to atom :2 (a nitrogen), making it a hydrazine-like structure. In the correct molecule, atom :2 should be a carbon (the alpha-carbon of the amino acid).\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000000", + "op_type": "change_atom_element", + "image_path": "images/000000.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([SH:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the image, the correct molecule is 4-tert-butylcatechol (or 4-tert-butylbenzene-1,2-diol). The tert-butyl group has three CH3 groups attached to a central carbon, with no SH group.\n\nIn the wrong SMILES, atom :3 is an SH group, but in the correct molecule it should be a CH3 group.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000012", + "op_type": "change_charge", + "image_path": "images/000012.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[OH+:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 12}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 12 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000011", + "op_type": "add_atom", + "image_path": "images/000011.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "Looking at the image, the correct molecule is 3-hydroxyphenylalanine (m-tyrosine), which has a carboxylic acid group (COOH) instead of an aldehyde (CHO).\n\nIn the wrong SMILES, atom :11 is a CH and atom :12 is =O, forming an aldehyde (CHO). In the correct molecule, this should be a carboxylic acid (COOH), meaning there needs to be an OH group added to the carbonyl carbon.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 11}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 11 + }, + "group": "OH" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000010", + "op_type": "remove_atom", + "image_path": "images/000010.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][NH2:14])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"O\", \"charge\": 0}\n\nWait, let me re-examine. The wrong SMILES has `[O:9][NH2:14]` which is an O-NH2 group (hydroxylamine-like). The correct molecule shows just an OH group at that position.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 8}, \"group\": \"NH2\"}\n\nHmm, let me reconsider. The wrong SMILES has `-[O:9][NH2:14]` on the ring, but the image shows just `-OH`. So I need to remove atom 14 (NH2) and the oxygen becomes OH.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000007", + "op_type": "move_substituent", + "image_path": "images/000007.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:7]1[cH:6][cH:5][cH:12][c:10]([OH:11])[c:8]1[OH:9]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the image, I see 4-tert-butylcatechol (a benzene ring with a tert-butyl group and two adjacent OH groups).\n\nIn the wrong SMILES, the ring connectivity is: atom 7 \u2192 6 \u2192 5 \u2192 12 \u2192 10(OH) \u2192 8(OH) \u2192 back to 7. The tert-butyl is on atom 7, and the two OH groups are on atoms 10 and 8 (adjacent to each other, and atom 8 is adjacent to atom 7).\n\nIn the image, the tert-butyl group is at position 4 relative to the catechol (1,2-dihydroxy). The two OH groups are on adjacent carbons, and the tert-butyl is separated from the nearest OH by two carbons (para to one OH).\n\nIn the wrong SMILES, the tert-butyl (atom 7) is directly adjacent to an OH-bearing carbon (atom 8). That makes it 3-tert-butylcatechol. In the correct molecule (4-tert-butylcatechol), the tert-butyl should be one position further away.\n\nThis means the tert-butyl group should move from atom 7 to atom 12 (or equivalently, the OH on atom 8 should move to atom 5). Looking more carefully at the topology:\n\nWrong: tBu-c7=c6-c5=c12-c10(OH)=c8(OH) (tBu adjacent to OH on c8)\nCorrect: tBu should be para to one OH, meaning two carbons between tBu and nearest OH.\n\nSwapping the tert-butyl substituent from atom 7 to atom 12 would give the correct 4-tert-butylcatechol, but that's complex. The simplest fix: move the OH from atom 8 to atom 5, so the two OHs are on atoms 10 and 5 (adjacent), and tBu on atom 7 is two positions away.\n\nActually, the simplest single action is to swap atoms 8 and 5 (moving OH from position 8 next to tBu to position 5 away from tBu):\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 8}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + }, + "restored_smiles": "CC(C)(C)c1cc(O)cc(O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000003", + "op_type": "remove_bond", + "image_path": "images/000003.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1([CH3:4])[CH2:3][O:9][c:8]2[cH:7][cH:6][c:5]1[cH:12][c:10]2[OH:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the image, I see a benzene ring with a tert-butyl group, and two OH groups on the ring. There is no oxygen bridge (no chromane/benzofuran-like ring) \u2014 it's simply a substituted benzene.\n\nThe wrong SMILES has an oxygen atom :9 forming a bridge (`[CH2:3][O:9][c:8]`), creating a fused ring system. In the correct molecule, there's no such oxygen bridge. Instead, atom :3 should connect directly to the ring, and the oxygen at position :9 should be removed. Looking more carefully, the correct molecule has a tert-butyl group (C(CH3)3, not C(CH3)2CH2O...) and two OH groups on the ring.\n\nThe key difference: the wrong SMILES has `[CH2:3]` bridging to `[O:9]` which connects to the ring. In the correct structure, there's no such CH2-O bridge. Atom :9 (the bridging O) needs to be removed, and atom :3 needs to become a CH3 group (the third methyl of the tert-butyl group), while the ring position where O:9 was connected should instead bear an OH group.\n\nExamining more carefully: removing the O at :9 and converting :3 from CH2 (bridging) to CH3 (methyl) effectively breaks the fused ring and gives us the tert-butyl group C(CH3)3. The ring atom :8 that was connected to O:9 now needs an OH \u2014 but :8 already connects to :10 which has OH:11. The image shows two OH groups on the ring.\n\nThe simplest fix: remove the bridging oxygen atom :9, which breaks the ring and leaves :3 as a pendant CH2 needing to become CH3, and :8 needing an OH.\n\nThe single most impactful correction is removing atom :9 (the bridging O):\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "CC(C)(C)c1cccc(O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000008", + "op_type": "swap_substituents", + "image_path": "images/000008.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the image, I see a benzene ring with a tert-butyl group and two OH groups. The two OH groups are on adjacent carbons (catechol-like arrangement) at positions 3 and 4 relative to the tert-butyl group.\n\nIn the wrong SMILES, the OH groups are at atoms 9 (on atom 8) and 11 (on atom 5). Let me trace the ring: atom 10 is connected to atom 8 (has OH:9), then 7, 6, 5 (has OH:11), then 12 back to 10. So the tert-butyl is on atom 10, and the OHs are on atoms 8 and 5 \u2014 these are at positions 2 and 5 (1,4 relative to each other).\n\nIn the correct image, the two OH groups are on adjacent carbons (positions 3,4 relative to tert-butyl, i.e., meta and para). That means one OH should move from atom 8 to be adjacent to atom 5's OH.\n\nThe correct molecule is 4-tert-butylcatechol, with OHs on adjacent carbons. Currently the OH at atom 8 (ortho to tert-butyl) needs to move to atom 6 (adjacent to atom 5 which has OH), making the two OHs adjacent.\n\nThis means moving the OH from atom 8 to atom 6.\n\n```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 8}, \"to_atom\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 8 + }, + "to_atom": { + "map_num": 6 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000014", + "op_type": "remove_bond", + "image_path": "images/000014.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:10]1)[O:9]2)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "Looking at the wrong SMILES, the aromatic ring contains a furan-like oxygen bridge (atoms 8, 9, 10 forming a benzofuran). In the correct image, the molecule is 3-hydroxyphenylalanine \u2014 the ring is a simple benzene with an OH group, not a fused oxygen ring.\n\nThe wrong SMILES has an oxygen atom at position :9 bridging atoms :8 and :10 (creating a benzofuran). In the correct molecule, atom :9 should be a carbon (part of the benzene ring) with an OH substituent.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"C\", \"charge\": 0}\n\nWait, let me re-examine. The wrong SMILES: `[c:8]([cH:10]1)[O:9]2` \u2014 atom 9 is an oxygen forming the bridge in the fused ring. In the correct molecule, there's no fused ring; instead there's a regular benzene ring with an OH group on one carbon.\n\nThe key difference: atom :9 (O) is part of the ring structure. In the correct molecule, that position should be a carbon atom bearing an OH group. Changing O:9 to C would break the furan ring and we need an OH group there.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"C\", \"charge\": 0}\n\nHmm, but that alone doesn't add the OH. Let me reconsider \u2014 the simplest single action:\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 9}, \"group\": \"OH\"}\n\nNo \u2014 the atom itself needs changing too. The most precise single fix: changing the oxygen atom :9 to a carbon effectively converts the benzofuran to a benzene ring, and we need an OH. But looking more carefully, if :9 becomes C, we also need an OH on :7 (the meta position).\n\nGiven the structure, the best single action:\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000001", + "op_type": "remove_atom", + "image_path": "images/000001.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([O:11][CH3:13])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the wrong SMILES, I see a benzene ring with a tert-butyl group, an OH, and an OCH3 group. The correct molecule in the image shows a benzene ring with a tert-butyl group and two OH groups (no OCH3).\n\nThe fix is to remove the CH3 group (atom map 13) attached to the oxygen (atom map 11), converting the -OCH3 into -OH.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 11}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 11 + }, + "group": "CH3" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000017", + "op_type": "add_functional_group", + "image_path": "images/000017.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "Looking at the image, the correct molecule is 3-hydroxyphenylalanine (meta-tyrosine), which has an OH group on the meta position of the benzene ring. The wrong SMILES has an unsubstituted benzene ring.\n\nIn the image, the OH group is at the meta position relative to the CH2 attachment. The CH2 is attached at atom :4, so the meta position would be atom :6 or :8. Looking at the structure, the OH is on atom :7 (the para-to-one-ortho, i.e., meta position from :4).\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 7 + }, + "group": "OH" + }, + "restored_smiles": "NC(Cc1ccc(O)cc1)C(=O)O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000002", + "op_type": "add_atom", + "image_path": "images/000002.png", + "wrong_smiles_mapped": "[CH:1]([CH3:2])([CH3:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "Looking at the wrong SMILES, atom :1 is `[CH]` with two methyl groups and an aryl group \u2014 that's only 3 explicit connections plus one H, meaning it's a carbon with a radical or unusual valence. In the correct image, the tert-butyl group has a central carbon with THREE methyl groups attached to the ring. So atom :1 should be a full `C` with three methyls (currently it only has two).\n\nThe fix is to add a CH3 group to atom :1.\n\n```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000019", + "op_type": "change_atom_element", + "image_path": "images/000019.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([SH:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 14}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000015", + "op_type": "add_bond", + "image_path": "images/000015.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12].[OH2:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "Looking at the image, the correct molecule is 3-hydroxyphenylalanine (m-tyrosine), which has a carboxylic acid group (COOH) instead of an aldehyde (CHO).\n\nIn the wrong SMILES, atom :11 is a CH (part of CHO aldehyde) and atom :12 is =O. The correct structure needs a carboxylic acid: C(=O)OH. The wrong SMILES has CHO where it should be COOH.\n\nI need to add an OH group to the carbonyl carbon (atom :11) to convert the aldehyde to a carboxylic acid.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 11}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 11 + }, + "group": "OH" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O.O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000023", + "op_type": "add_bond", + "image_path": "images/000023.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "Looking at the image, I see a triphenylene/anthracene-like fused ring system (specifically 2-methyltetraphene or a methylated tricyclic aromatic) with a methyl group on the rightmost ring. The wrong SMILES has a disconnected CH4 fragment (atom map 1) that shouldn't be there, and the methyl group (atom map 14) is on the wrong position.\n\nThe image shows the correct molecule is 2,8-dimethylanthracene or similar \u2014 actually, it's a three-fused-ring system (tetraphene/benz[a]anthracene) with two methyl groups: one on the left ring and one on the right ring.\n\nWait \u2014 looking more carefully at the wrong SMILES, there's a disconnected methane [CH4:1] and only one methyl group on the fused ring system. The correct image shows the methyl on the left side of the molecule as well. The disconnected CH4 (atom :1) should be connected to the left ring as a methyl group.\n\nLooking at the fused ring system, atom :3 or a similar position on the left ring needs the methyl. Based on the structure in the image, the methyl on the left appears to be at a position corresponding to atom :3 in the SMILES.\n\nThe fix is to connect the disconnected CH4 (atom :1) to the appropriate atom on the left ring. Examining the topology, atom :4 appears to be the correct anchor point on the left ring.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 4}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Cc1ccc2c(ccc3cc4cccc(C)c4cc32)c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000013", + "op_type": "change_bond_order", + "image_path": "images/000013.png", + "wrong_smiles_mapped": "[NH:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}\n\nWait, let me re-analyze.\n\nThe wrong SMILES has `[NH:1]=[C:2]` \u2014 an imine (N=C double bond). The correct molecule in the image shows an amine (NH2 group) with a single bond to carbon. So I need to change the N=C double bond to a single bond, and also fix the NH to NH2.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"SINGLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000021", + "op_type": "add_atom", + "image_path": "images/000021.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "Looking at the image, I see a triphenylene/anthracene-like fused ring system with two methyl groups \u2014 one on the left side and one on the right side.\n\nThe wrong SMILES has only one methyl group (on atom :2). The correct molecule has a second methyl group on the rightmost ring.\n\nExamining the structure, the second methyl group needs to be added to atom :13, which corresponds to the para position on the rightmost ring.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 13}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 13 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000022", + "op_type": "remove_bond", + "image_path": "images/000022.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]-2[c:7]2[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]24)[cH:18][c:19]3[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 1}, \"from_atom\": {\"map_num\": 2}, \"to_atom\": {\"map_num\": 4}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 1 + }, + "from_atom": { + "map_num": 2 + }, + "to_atom": { + "map_num": 4 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 3 C, 5, is greater than permitted" + }, + { + "id": "000020", + "op_type": "remove_atom", + "image_path": "images/000020.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH2:14][OH:21])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 13}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "CH3" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='CH3' not found at anchor=12" + }, + { + "id": "000024", + "op_type": "remove_functional_group", + "image_path": "images/000024.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH3:21])[c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 21}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 21 + } + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000025", + "op_type": "add_functional_group", + "image_path": "images/000025.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]3[c:7]([cH:8][cH:9][c:10]4[cH:11][c:12]([CH3:13])[cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "Looking at the image, I see a triphenylene/anthracene-like fused ring system (specifically, this appears to be 2-methylanthracene or similar). The methyl group is on the leftmost ring in the image.\n\nLet me analyze the wrong SMILES. The current SMILES has the methyl group on atom :12. I need to determine where it should be instead by comparing the structure.\n\nThe image shows a three-fused-ring system (anthracene skeleton) with a methyl group on the far-right ring at a specific position, and looking more carefully, there's a methyl on the left side too \u2014 no, there's just one methyl group visible on the right side of the molecule.\n\nWait, looking again at the image, I see the methyl group is on the left ring (bottom-left position). In the wrong SMILES, the methyl is attached to atom :12. Let me trace the structure to see where it needs to move.\n\nTracing the SMILES: This is a three-fused ring (anthracene) system. The methyl is currently on atom :12 in the rightmost ring. In the image, the methyl appears to be on the leftmost ring instead.\n\nLooking at the symmetry, the methyl needs to move from atom :12 (right ring) to the corresponding position on the left ring, which would be atom :2 or :3.\n\nExamining the image more carefully, the methyl is at the para-like position of the left ring, which corresponds to atom :2.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 13}, \"from_atom\": {\"map_num\": 12}, \"to_atom\": {\"map_num\": 2}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 13 + }, + "from_atom": { + "map_num": 12 + }, + "to_atom": { + "map_num": 2 + } + }, + "restored_smiles": "Cc1ccc2cc3ccc4ccccc4c3cc2c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000018", + "op_type": "move_substituent", + "image_path": "images/000018.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:10]1[OH:9])[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "Looking at the wrong SMILES: `[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:10]1[OH:9])[C:11](=[O:12])[OH:13]`\n\nThis represents tyrosine with the OH group on the ortho position (attached to atom 10, which is adjacent to atom 4 where the CH2 connects).\n\nIn the correct image, the OH group is on the meta position (3-position) of the benzene ring, not the ortho position (2-position).\n\nThe wrong SMILES has the OH on atom 10 which is directly bonded to atom 4 (the attachment point of CH2). I need to move the OH from atom 10 to atom 7 (the meta position).\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "NC(Cc1ccc(O)cc1)C(=O)O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000027", + "op_type": "swap_substituents", + "image_path": "images/000027.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:20][c:19]2[c:5]3[cH:6][c:7]([c:8]([cH:18]2)[CH:4]=[CH:3]1)-[c:17]1[c:11]([cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[CH:10]=[CH:9]3", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "Looking at the image, I see a fully aromatic tricyclic system (triphenylene/anthracene-like) with two methyl groups. The correct molecule is 2,10-dimethylanthracene (or similar), where all three rings are fully aromatic.\n\nExamining the wrong SMILES, I notice atom :2 is `[C:2]` (aliphatic carbon with a double bond pattern), but in the correct molecule this should be an aromatic carbon since all rings are fully aromatic.\n\nThe key issue is that atom :2 is written as an aliphatic `C` with explicit double bonds, breaking the aromaticity. Changing atom :2 to aromatic `c` would fix the structure.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}\n\nHmm, let me re-examine more carefully.\n\nLooking at the wrong SMILES, atoms :1 through :4 form a non-aromatic chain: `[CH3:1][C:2]1=[CH:20]...[CH:4]=[CH:3]1`. This means atom :1 is a methyl group attached to a non-aromatic carbon :2, and there are explicit double bonds through :3 and :4.\n\nIn the image, all three fused rings are aromatic. The methyl at atom :1 should be attached to an aromatic ring. The issue is that atom :2 should be aromatic \u2014 but actually the deeper problem is the bond between :3 and :4 is shown as a double bond (`[CH:4]=[CH:3]`), whereas in a fully aromatic system these should be aromatic bonds.\n\nThe simplest single fix: removing the methyl group at atom :1 and making :2 part of the aromatic system won't work as a single action. Let me reconsider.\n\nComparing the two methyl groups: the image shows two CH\u2083 groups on the outer rings. The wrong SMILES has CH\u2083 at :1 and :14. Atom :1's CH\u2083 is on atom :2 which is non-aromatic. The fix is to make atom :2 aromatic.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 1}}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000029", + "op_type": "add_atom", + "image_path": "images/000029.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])[OH:33])[cH:34][cH:35][cH:36][c:37]34)[c:38]3[cH:39][cH:40][cH:41][cH:42][c:43]23)[cH:44]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has two sulfonic acid groups (SO\u2083H), each with S(=O)(=O)(OH). \n\nExamining the wrong SMILES, the sulfonic acid group at atom :31 (S) only has one =O (atom :32) and one OH (atom :33), meaning it's missing a second =O. The other sulfonic acid group at atom :2 has two =O groups (atoms :1 and :3) plus OH (atom :4), which is correct.\n\nSo the fix is to add a double-bonded oxygen to the sulfur at atom :31.\n\n```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 31}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 31 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000032", + "op_type": "remove_bond", + "image_path": "images/000032.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]3[c:39]4[cH:40][cH:41][cH:42][c:43]([c:44]24)-[c:37]2[cH:36][cH:35][c:30]([S:31](=[O:32])(=[O:33])[OH:34])[c:29]4[c:21]([NH:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:20][cH:19][c:18]([c:38]42)[N:17]=[N:16]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the image, I can see two naphthalene units connected by azo groups (N=N), with sulfonic acid groups and other substituents. The correct molecule is a linear/extended structure, not a fused ring system.\n\nComparing the wrong SMILES to the image: the wrong SMILES has a bond connecting atoms that creates a fused polycyclic system (between the two naphthalene cores), whereas the image shows two separate naphthalene units linked via azo bonds (N=N).\n\nSpecifically, the bond between atoms 16 and 15 creates the unwanted ring fusion. In the image, atom 16 (from the right-side azo group N=N) connects to atom 15 (part of the left naphthalene), but looking more carefully at the structure, the issue is that there's a bond between atoms 39/44 and 37/38 that fuses the two naphthalene rings together.\n\nThe wrong SMILES has a direct bond between the two naphthalene systems (atoms 43 and 37), creating a fused structure. In the correct molecule, these naphthalene units are separate, connected only through the azo linkage (N=N).\n\nRemoving the bond between atoms 43 and 37 would break the direct connection between the two naphthalene units, making them separate and connected only via the azo groups as shown in the image.\n\n```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 43}, \"atom2\": {\"map_num\": 37}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 43 + }, + "atom2": { + "map_num": 37 + } + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000028", + "op_type": "remove_atom", + "image_path": "images/000028.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[OH:46])[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the image, I need to compare the correct molecule with the wrong SMILES.\n\nThe correct molecule shows an NH group connecting to a phenyl ring without an OH substituent on that phenyl ring. In the wrong SMILES, atom 46 is an OH group attached to the phenyl ring (atom 28) that is connected via NH (atom 22).\n\nIn the image, the phenyl ring connected to the NH group is unsubstituted (no OH group).\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 46}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 46 + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000034", + "op_type": "remove_functional_group", + "image_path": "images/000034.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[c:13]([Cl:46])[cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has the left side azo group (N=N) connecting to a naphthalene ring system, not to a benzene ring with a Cl substituent.\n\nComparing the wrong SMILES with the image:\n- The wrong SMILES has a Cl atom (map 46) on the naphthalene ring at position map 13\n- The correct molecule in the image shows no Cl substituent on that ring\n\nThe fix is to remove the Cl atom.\n\n```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 13}, \"group\": \"Cl\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "Cl" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000030", + "op_type": "change_charge", + "image_path": "images/000030.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[NH+:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has two azo groups (N=N) connecting aromatic rings, with the middle section being a naphthalene system. Comparing with the wrong SMILES, the key difference is at atom 17 - in the wrong SMILES it's `[NH+]` (a protonated nitrogen in a hydrazone-like linkage), but in the image it shows a neutral azo bond (N=N) without any protonation.\n\nThe wrong SMILES has `[N:16]=[NH+:17]` while the image shows `N=N` (a neutral azo linkage).\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 17}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 17 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000038", + "op_type": "add_atom", + "image_path": "images/000038.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "NCSSc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000026", + "op_type": "move_substituent", + "image_path": "images/000026.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][c:15]([CH3:14])[cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "Looking at the wrong SMILES, I need to parse the structure. The wrong SMILES represents a three-ring fused system (anthracene-like) with two methyl groups. Let me trace the atom map numbers to understand the current structure and compare with the image.\n\nThe image shows a triphenylene/anthracene-type structure with three linearly fused rings and two methyl groups - one on the leftmost ring and one on the rightmost ring.\n\nAnalyzing the wrong SMILES: `[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][c:15]([CH3:14])[cH:16][c:17]34)[cH:18][c:19]2[cH:20]1`\n\nThis is a three-ring fused system (anthracene backbone) with:\n- CH3 at atom 1 attached to atom 2 (one end)\n- CH3 at atom 14 attached to atom 15 (other end)\n\nThe image shows the correct molecule is 2,8-dimethylanthracene (or similar positioning). Let me check the methyl positions carefully.\n\nIn the wrong SMILES, the methyl (atom 14) is on atom 15. Looking at the image, the right-side methyl appears to be at a different position on that ring. In the current SMILES, atom 15 is the 3rd carbon of the right ring. The image shows the methyl should be on what corresponds to atom 11 (the para position of the right ring relative to the fusion).\n\nComparing the structure: the methyl at atom 14 is currently on atom 15, but in the image it should be on atom 11.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 14}, \"from_atom\": {\"map_num\": 15}, \"to_atom\": {\"map_num\": 11}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 15 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 10 C, 5, is greater than permitted" + }, + { + "id": "000037", + "op_type": "remove_atom", + "image_path": "images/000037.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 11}, \"group\": \"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 11 + }, + "group": "OH" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000036", + "op_type": "change_atom_element", + "image_path": "images/000036.png", + "wrong_smiles_mapped": "[NH2:1][NH:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "Looking at the image, the correct molecule is H\u2082N-CH\u2082-CH\u2082-S-S-c\u2081ccccc\u2081 (2-aminoethyl phenyl disulfide).\n\nThe wrong SMILES is: [NH2:1][NH:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1\n\nThis has NH at position 2, but the image shows a CH\u2082 group there (it's an ethylamine chain: NH\u2082-CH\u2082-CH\u2082-S-S-Ph).\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000039", + "op_type": "change_bond_order", + "image_path": "images/000039.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[SH:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "Looking at the image, the correct molecule is H\u2082N-CH\u2082-CH\u2082-S-S-c\u2081ccccc\u2081 (2-aminoethyl phenyl disulfide).\n\nComparing with the wrong SMILES: `[NH2:1][CH2:2][CH:3]=[SH:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1`\n\nThe issue is between atoms 3 and 4: the wrong SMILES has `[CH:3]=[SH:4]` (a C=S double bond with an H on sulfur), but the correct molecule has `[CH2:3]-[S:4]` (a C-S single bond). Atom 3 should be CH\u2082 and atom 4 should be S without H, connected by a single bond.\n\nThe key fix is changing the double bond between atoms 3 and 4 to a single bond (the hydrogens will adjust automatically).\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000041", + "op_type": "add_bond", + "image_path": "images/000041.png", + "wrong_smiles_mapped": "[CH3:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH3:2]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "Looking at the image, the correct molecule is 2-aminoethyl phenyl disulfide: H\u2082N-CH\u2082-CH\u2082-S-S-c\u2081ccccc\u2081.\n\nThe wrong SMILES has two disconnected fragments: `[CH3:3][S:4][S:5]c1ccccc1` and `[NH2:1][CH3:2]`. These should be connected \u2014 the NH2-CH2 fragment (atoms 1,2) should be bonded to atom 3 (which is CH2, connecting to the disulfide chain).\n\nThe fix is to add a bond between atom 2 and atom 3, connecting the two fragments.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000040", + "op_type": "remove_bond", + "image_path": "images/000040.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[c:7]2[cH:8][cH:9][cH:10][c:11]1-2", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "Looking at the image, I see a simple phenyl ring (benzene) connected to the disulfide chain, not a fused bicyclic system like azulene/indene.\n\nThe wrong SMILES has a fused ring system (indicated by the -2 closure creating a bond between atoms 7 and 11), while the correct molecule has a regular 6-membered benzene ring.\n\nThe wrong SMILES ring system has 5 atoms (c6, c7, c8, c9, c10, c11 with a bridge between c7 and c11), but the image shows a normal phenyl group. I need to remove the extra bond that creates the fused ring and add a missing CH to complete the benzene ring.\n\nThe issue is that atom 11 is bonded back to atom 7 (the `-2` closure), creating a fused ring. Removing that bond and adding a proper CH to close a 6-membered ring is needed. Let me re-examine:\n\nThe wrong SMILES: `[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[c:7]2[cH:8][cH:9][cH:10][c:11]1-2`\n\nThis creates a bicyclic system. The correct molecule just has a phenyl ring. I need to remove the bond between atoms 7 and 11 (the \"2\" ring closure) and add a CH atom to complete the 6-membered ring.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 11}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 11 + } + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000042", + "op_type": "remove_functional_group", + "image_path": "images/000042.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[Cl:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "Looking at the image, the correct molecule is 2-aminoethyl phenyl disulfide: H\u2082N-CH\u2082-CH\u2082-S-S-c\u2081ccccc\u2081.\n\nThe wrong SMILES has: NH\u2082-CH\u2082-CH(Cl)-S-S-Ph\n\nComparing to the image, atom :3 (CH) should be CH\u2082 (no Cl substituent), so the Cl atom at map_num 12 needs to be removed.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 12}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000033", + "op_type": "add_bond", + "image_path": "images/000033.png", + "wrong_smiles_mapped": "[O:1]=[S:2]([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1.[OH2:3]", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the wrong SMILES, I need to compare it with the image of the correct molecule.\n\nThe wrong SMILES has `[OH2:3]` as a disconnected water molecule and the sulfonic acid group on the left ring (`[S:2]`) only has one `=O` and one `OH`, i.e., `S(=O)(OH)` which is incomplete for a sulfonic acid group.\n\nIn the correct molecule image, the left side has a full sulfonic acid group `S(=O)(=O)(OH)` \u2014 matching the right side's sulfonic acid group. The wrong SMILES is missing a `=O` on atom :2 and has a separate water molecule `:3` instead.\n\nThe fix is to remove the disconnected water molecule (atom :3) and add the missing `=O` to the sulfur atom :2 to complete the sulfonic acid group.\n\nLooking more carefully: the wrong SMILES has `[O:1]=[S:2]([OH:4])` plus `[OH2:3]` as a fragment. The correct structure needs `O=S(=O)(OH)` on atom :2. So I need to change the water atom :3 into an oxygen double-bonded to sulfur :2.\n\nThe simplest single action: add a bond between atom :3 (the oxygen of water) and atom :2 (the sulfur), making it a double bond. But atom :3 is `OH2` which isn't right for `=O`.\n\nThe best single fix is to change atom :3 from water to a double-bonded oxygen on the sulfur:\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000016", + "op_type": "remove_functional_group", + "image_path": "images/000016.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:14])[c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000035", + "op_type": "move_substituent", + "image_path": "images/000035.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][C:12]2=[CH:13][CH:14]=[C:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:41]3[cH:40][cH:39][c:44]2[cH:43][cH:42]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has two naphthalene groups connected by azo linkages, with sulfonic acid groups and an NH-phenyl group. Comparing with the wrong SMILES:\n\nIn the wrong SMILES, the left-side aromatic ring (atoms 5-9, 45) is a benzene (6-membered single ring), but in the image, the left side also has a naphthalene system (fused bicyclic ring), similar to the right side.\n\nThe wrong SMILES has atoms 5,6,7,8,9,45 forming a simple benzene ring with the SO3H at atom 5 and the azo group at atom 9. But in the image, the left portion is a naphthalene with SO3H on one ring and the azo linkage on the other.\n\nLooking more carefully at the structure, the left aromatic system bearing the SO3H needs to be a naphthalene (two fused rings) rather than a single benzene ring. This means I need to add a fused ring. The simplest correction is to convert the benzene ring into a naphthalene by adding a bond to fuse it with the naphthalene ring from atom 12's side.\n\nActually, re-examining: the central naphthalene (atoms 12-15, 41,40,39,44,43,42) connects to both azo groups. The left aromatic is atoms 5,6,7,8,9,45 (benzene). The right aromatic is atoms 18,19,20,21,29,30,35,36,37,38 (naphthalene).\n\nIn the image, both sides are naphthalene systems. So the left benzene (atoms 5-9,45) needs an additional fused ring to become naphthalene.\n\nThe fix is to convert the central part: looking again, the central unit in the wrong SMILES (atoms 12,13,14,15,41,40,39,44,43,42) is a naphthalene. In the image, the central unit is also naphthalene. The left unit is a single benzene but should be naphthalene.\n\nThe most direct single action to fix this is to add a bond between atoms 8 and 12 to extend/fuse, but that changes connectivity. Instead, looking at atom 15 connecting to the right azo and atom 12 connecting via the left azo \u2014 the central naphthalene seems correct.\n\nThe simplest fix: the left benzene needs to become a naphthalene. This can be done by adding a fused ring. Since we need a single action, I'll use `AddBond` to create the fusion, but that doesn't add atoms.\n\nRe-examining: perhaps the issue is simpler. The bond between atoms 14 and 15 in the central naphthalene \u2014 comparing carefully, maybe atom 12's ring system should connect to the left benzene to form one larger naphthalene, and the separate benzene shouldn't exist. But that's multiple changes.\n\nLet me reconsider: perhaps the NH group (atom 22) should be an N=N azo group instead.\n\nLooking at the image: left SO3H-naphthalene \u2014 N=N \u2014 naphthalene \u2014 N=N \u2014 naphthalene(NH-phenyl)(SO3H). The wrong SMILES has: left SO3H-benzene \u2014 N=N \u2014 naphthalene \u2014 N=N \u2014 naphthalene(NH-phenyl)(SO3H).\n\nThe difference is benzene vs naphthalene on the left. The simplest single fix to address this structural difference would be adding a fused ring to the left benzene. But that requires multiple atoms. Using AddGroup isn't quite right either.\n\nGiven the action types available, the closest single action: the bond between atoms 8 and 45 could be changed, but actually we need to add atoms. Let me check if MoveSubstituent works \u2014 moving the SO3H from the benzene to be on a naphthalene.\n\nAfter deeper analysis, the most likely single-action fix is changing atom 12's ring connectivity. But actually, perhaps the simplest difference is that the bond 14-15 should be a single bond instead of double (or vice versa):\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 9}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 9 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Can't kekulize mol. Unkekulized atoms: 4 5 6 8 44" + }, + { + "id": "000046", + "op_type": "add_atom", + "image_path": "images/000046.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9](=[O:10])[OH:11]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 9}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 9 + }, + "group": "OH" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000047", + "op_type": "change_charge", + "image_path": "images/000047.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[OH+:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000031", + "op_type": "change_bond_order", + "image_path": "images/000031.png", + "wrong_smiles_mapped": "[OH:1][SH:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "Looking at the wrong SMILES, I need to compare it with the correct molecule shown in the image.\n\nThe image shows a symmetric-like molecule with two naphthalene rings connected by azo groups, with sulfonic acid groups and a phenylamino group. \n\nIn the wrong SMILES, atom :2 is `[SH]` \u2014 a sulfur with a hydrogen attached. In a sulfonic acid group (`-S(=O)(=O)OH`), the sulfur should not have a hydrogen. The sulfur in a proper sulfonic acid group has three oxygen substituents (two =O and one -OH) plus the connection to the aromatic ring, with no S-H bond.\n\nLooking at the SMILES more carefully: `[OH:1][SH:2](=[O:3])([OH:4])` \u2014 this sulfur has an H, two OH groups, and one =O. A proper sulfonic acid is `S(=O)(=O)OH` \u2014 two double-bonded oxygens and one OH.\n\nThe issue is that atom :2 (S) has an extra H and an extra OH, but is missing a second C=O. Actually, comparing: the wrong SMILES has S bonded to OH:1, =O:3, and OH:4 (plus SH). The correct sulfonic acid should be S(=O)(=O)(OH) with no SH.\n\nThe fix: one of the OH groups (atom :1) should be a double-bonded O instead, and the H on sulfur should be removed. But since I can only output a single action, let me reconsider.\n\nThe wrong molecule has `[OH:1][SH:2](=[O:3])([OH:4])` which gives S with: -OH(1), =O(3), -OH(4), and an H on S. The correct sulfonic acid needs S with: =O, =O, -OH. So the bond between atoms 1 and 2 should be a double bond (changing -OH to =O), and the H on S needs removal.\n\nThe simplest single fix: Change atom :2 from `SH` to `S` (removing the H) and change the bond to atom :1 to double. But that's two actions.\n\nActually, looking again at the image, the left sulfonic acid group has S with =O, =O, and OH \u2014 three oxygens. The wrong SMILES has S with -OH, =O, -OH plus an H on S. The key single change: change the bond between atom :1 (O) and atom :2 (S) from single to double, which would implicitly remove the H from S.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000048", + "op_type": "change_bond_order", + "image_path": "images/000048.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9]([OH:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "Looking at the image, the correct molecule has a phosphorus atom with two OH groups and one =O (double-bonded oxygen), connected via sulfur. \n\nIn the wrong SMILES, the phosphorus (atom 9) has three OH groups (atoms 10, 11, 12) all as single bonds, and it's a PH. The correct structure should have P with two OH groups, one =O, and no H on P.\n\nComparing: the wrong SMILES has P bonded to three OH groups all via single bonds (and an H on P). The correct molecule has P with two OH, one =O, and no PH. So I need to change one of the OH oxygens to a double-bonded O (removing its H) and remove the H from P.\n\nThe key single change: atom 12 (OH) should become a =O instead. But I also need to handle the PH \u2192 P. Let me focus on the most impactful single action.\n\nLooking more carefully, the wrong SMILES has `[PH:9]` with three `[OH]` groups. The correct molecule has `P(=O)(OH)(OH)` with no H on P. Changing one OH to =O would fix the oxygen, but the PH still has an extra H.\n\nActually, if we change atom 12 from OH to O with a double bond, that accounts for removing one H from O. The PH having an extra H \u2014 changing the bond order from single to double between P and O12 would remove the H from both P and O if we think in terms of valence.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 9}, \"atom2\": {\"map_num\": 12}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 9 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000044", + "op_type": "change_atom_element", + "image_path": "images/000044.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][P:9](=[O:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "Looking at the image, the correct molecule has a sulfur (S) atom connecting the carbon chain to the phosphorus, whereas the wrong SMILES has an oxygen (O) at that position (atom map number 8).\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 8}, \"element\": \"S\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 8 + }, + "element": "S", + "charge": 0 + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000045", + "op_type": "remove_atom", + "image_path": "images/000045.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[OH:13]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "Looking at the image, I see: NH2-CH2-CH2-CH2-NH-CH2-CH2-S-P(=O)(OH)(OH)\n\nThe correct molecule is a linear chain without the OH group on the carbon. In the wrong SMILES, atom :2 is a CH with an OH group attached (atom :13), making it a chiral center. In the image, there's no OH on that carbon \u2014 it should be a CH2.\n\nThe fix is to remove the OH group (atom :13) from atom :2.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "OH" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000052", + "op_type": "add_functional_group", + "image_path": "images/000052.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][S:7][P:8](=[O:9])([OH:10])[OH:11]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"NH2\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "NH2" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000054", + "op_type": "remove_atom", + "image_path": "images/000054.png", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([NH2:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "NH2" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000055", + "op_type": "change_charge", + "image_path": "images/000055.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][NH+:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000051", + "op_type": "remove_functional_group", + "image_path": "images/000051.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[F:13]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "Looking at the image, I see: NH2-CH2-CH2-CH2-NH-CH2-CH2-S-P(=O)(OH)(OH)\n\nThe correct molecule has a simple CH2 chain from NH2, with no fluorine atom. In the wrong SMILES, atom :2 is a CH with F attached, but in the correct molecule it should be a CH2 (no fluorine).\n\nThe fix is to remove the fluorine atom (map_num 13).\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000053", + "op_type": "change_atom_element", + "image_path": "images/000053.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][N:5]=[N:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "Looking at the image, I see a 6-membered ring with two nitrogen atoms: one N at the top and one NH at the bottom-left. This is 1,2,3,4-tetrahydropyrimidine (or a pyrimidine-like ring with partial saturation). The nitrogens are at positions 1 and 3 of the ring (para-like, separated by two carbons on each side).\n\nThe correct molecule from the image is a 6-membered ring with two N atoms (one =N, one NH) and four carbons, with a double bond visible on the right side.\n\nThe wrong SMILES: `[CH:1]1=[CH:2][NH:3][CH2:4][N:5]=[N:6]1`\n\nThis has atoms: CH=CH-NH-CH2-N=N in a ring \u2014 notably it has two adjacent nitrogens (N=N at positions 5-6), which doesn't match the image.\n\nThe correct molecule should be a pyrimidine-type ring (1,4-diazine or similar). Looking at the image carefully: N at top, then two carbons going right with a double bond between them, then NH at bottom-left, then CH2 going up to the top N. This matches 1,2,3,4-tetrahydropyrimidine.\n\nThe wrong SMILES has N=N (atom 6 is N), but in the correct structure atom 6 should be C (part of CH=CH). I need to change atom 6 from N to C.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000050", + "op_type": "add_bond", + "image_path": "images/000050.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12].[NH2:1][CH3:2]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "Looking at the image, the correct molecule is a single connected chain: H2N-CH2-CH2-CH2-NH-CH2-CH2-S-P(=O)(OH)(OH).\n\nIn the wrong SMILES, the NH2 and CH3 (atoms :1 and :2) are a separate fragment disconnected from the main chain. The main chain starts with CH3:3. To match the image, atom :3 should have an NH2 group attached (making it CH2-NH2 instead of CH3), and the separate NH2-CH3 fragment (atoms :1 and :2) should be removed.\n\nLooking more carefully: the wrong SMILES has `[CH3:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12]` plus a disconnected `[NH2:1][CH3:2]`. The correct molecule needs atom :1 (NH2) connected to atom :3's chain to form NH2-CH2-CH2-CH2-NH-...\n\nThe fix is to change atom :2 from CH3 to CH2 and bond it to atom :3, but since we need a single action, the simplest correction is to add a bond between atom :2 and atom :3.\n\nBut atom :3 is CH3 (3 hydrogens) and atom :2 is CH3 (3 hydrogens). Adding a bond between them would give CH2-CH2, and with NH2 on atom :1, we'd get NH2-CH2-CH2-... which matches.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000043", + "op_type": "add_functional_group", + "image_path": "images/000043.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"NH2\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "NH2" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000058", + "op_type": "remove_functional_group", + "image_path": "images/000058.png", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([CH3:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000057", + "op_type": "remove_bond", + "image_path": "images/000057.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH:4]2[N:5]=[C:6]12", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "The wrong SMILES represents a bicyclic fused ring system (a purine-like fragment), while the image shows a 6-membered ring with two nitrogens \u2014 pyrimidine/1,2-dihydropyrimidine (a single ring). The key issue is the bond between atoms 4 and 6 that creates the fused bicyclic system. Removing that bond converts it to the correct single 6-membered ring matching the image.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 6}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000061", + "op_type": "add_atom", + "image_path": "images/000061.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a CH2OH (hydroxymethyl) group on the aromatic ring, whereas the wrong SMILES has a CH3 group at position 16.\n\nThe substituent on the ring at atom 15 should be a CH2OH group instead of just CH3.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 16}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 16 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000056", + "op_type": "change_bond_order", + "image_path": "images/000056.png", + "wrong_smiles_mapped": "[C:1]1=[CH:2][NH:3][CH2:4][N:5]=[C:6]=1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "Looking at the image, I see a six-membered ring with two nitrogens (a pyrimidine-like structure): one N at the top and one NH at the bottom-left. The ring has double bonds creating a partially saturated system (1,2-dihydropyrimidine).\n\nThe wrong SMILES is: `C1=C[NH]C[N]=C1` \u2014 a 6-membered ring with atoms mapped 1-6.\n\nComparing the image to the wrong SMILES, the issue is that atom :4 (between the two nitrogens) is `CH2` in the wrong SMILES, but in the correct molecule from the image, the corresponding carbon should be part of a double bond (C=C), and atom :2 should be `CH2` instead.\n\nSpecifically, in the wrong SMILES there's a double bond between atoms 1 and 2, but in the correct image the double bond pattern differs. The key difference is that atom :4 should not be CH2 \u2014 looking more carefully:\n\nThe correct molecule is 1,2-dihydropyrimidine. The wrong SMILES has the NH at position 3 and a CH2 at position 4. In the image, the saturated portion is at the top-left (between the top N and the NH). So atom :2 (currently `CH`) should be `CH2`, and atom :4 (currently `CH2`) should be `CH` with a double bond adjustment.\n\nThis means the bond between atoms 4 and 5 should be a double bond (currently single), and the bond between atoms 1 and 2 should be single (currently double).\n\nThe net correction is swapping substituents/hydrogens between atoms 2 and 4:\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 4}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 4 + } + }, + "restored_smiles": "C1=C=NCNC=1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000063", + "op_type": "change_bond_order", + "image_path": "images/000063.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a long alkyl chain attached to the nitrogen. Let me count the carbons in the chain from the image: the chain extends from N through about 8 CH2 groups ending in a CH3, making it a decyl chain (10 carbons total).\n\nIn the wrong SMILES, the chain is: [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][N:11]\n\nThis chain has a double bond between atoms 6 and 7. In the image, the chain is fully saturated (all single bonds).\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000049", + "op_type": "remove_bond", + "image_path": "images/000049.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[O:12]1", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "Looking at the image, the correct molecule is an open-chain structure: H2N-CH2-CH2-CH2-NH-CH2-CH2-S-P(=O)(OH)(OH).\n\nThe wrong SMILES has a ring closure between atoms :3 and :12 (the CH and the O on phosphorus), making it cyclic. In the correct molecule, the phosphorus has two OH groups and no ring \u2014 the O:12 should be replaced by an OH group, and the bond closing the ring between atom :3 and :12 needs to be removed.\n\nComparing more carefully:\n- Wrong SMILES ring: CH:3 is connected back to O:12 on phosphorus, forming a cycle.\n- Correct molecule: P has =O, OH, OH (two OH groups), and is connected to S. No ring.\n\nThe fix is to remove the ring bond between atom :3 (CH) and atom :12 (O), and atom :12 becomes an OH group on phosphorus. But since :12 is already an O bonded to P:9, removing the bond from :3 to :12 opens the ring, and :12 would need a hydrogen (becoming OH).\n\nThe simplest single action: remove the bond between atoms :3 and :12.\n\n```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 12}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 12 + } + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000067", + "op_type": "add_functional_group", + "image_path": "images/000067.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a CH2OH (hydroxymethyl) group on the aromatic ring, whereas the wrong SMILES has a CH3 group at position 16.\n\nThe substituent at atom map 16 (the methyl group on the ring between the N-acetyl and the N-methyl/alkyl groups) should be a CH2OH group instead of just CH3.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 16}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 16 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000059", + "op_type": "change_atom_element", + "image_path": "images/000059.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][SH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a hydroxymethyl group (CH2OH) on the benzene ring, whereas the wrong SMILES has a CH2SH (thiol) group instead.\n\nSpecifically, atom :17 is S (sulfur, as SH) in the wrong SMILES, but should be O (oxygen, as OH) in the correct molecule.\n\n```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 17}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 17 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000065", + "op_type": "add_bond", + "image_path": "images/000065.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH2:20])[cH:24]1.[CH:21]([CH3:22])=[O:23]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has an acetamide group (NHC(=O)CH3) attached to the aromatic ring at the position where the NH2 group is in the wrong SMILES. The wrong SMILES has NH2 at atom 19 and a separate aldehyde fragment (CH(CH3)=O as atoms 21-23).\n\nThe fix is to convert the NH2 group at atom 19 into an NHCOCH3 (acetamide) group, which means removing the NH2 and adding the correct group. Looking more carefully, the separate fragment `[CH:21]([CH3:22])=[O:23]` is an acetaldehyde-like piece that should be connected to the NH2 nitrogen as an amide.\n\nThe NH2 at position 20 on atom 19 needs to be replaced by the NHC(=O)CH3 group. The separate fragment (atoms 21-23) represents the acetyl portion. So the fix is to bond the nitrogen of NH2 (which becomes NH) to the carbonyl carbon of the acetyl fragment.\n\nThe NH2 group on atom 19 should connect to atom 21 (the carbonyl carbon). This means adding a bond between the NH (from NH2 at atom 19's substituent) and atom 21.\n\nSince the NH2 is a group on atom 19, and atoms 21-23 are a disconnected fragment, the correction is to add a bond from atom 19 to atom 21, converting NH2 to NH (by forming the new bond).\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 20}, \"atom2\": {\"map_num\": 21}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 20 + }, + "atom2": { + "map_num": 21 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000066", + "op_type": "remove_functional_group", + "image_path": "images/000066.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[OH:25]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, the correct molecule has:\n- A pyridine ring with NH-acetyl group, a CH2OH group, and an N(CH3) group connected to a straight alkyl chain\n- The alkyl chain connected to the nitrogen on the ring is a straight chain without the branching (no OH and no extra CH3 branch)\n\nComparing the wrong SMILES to the image:\n- The wrong SMILES has `[CH3:1][CH:2]([...chain...])[OH:25]`, meaning the chain has a branch with CH3 and OH (a sec-alcohol)\n- In the image, the chain is a straight unbranched alkyl chain (decyl/nonyl chain) with no OH group\n\nThe fix is to remove the OH group at atom 25.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000069", + "op_type": "change_atom_element", + "image_path": "images/000069.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][O:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 10}, \"atom2\": {\"map_num\": 11}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + } + }, + "restored_smiles": "CC1(CCN(O)CCCC(=O)c2ccc(F)cc2)C(=O)NCN1c1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000060", + "op_type": "remove_atom", + "image_path": "images/000060.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[NH2:25]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I see a molecule with:\n- A pyridine ring with an acetylamino group, a hydroxymethyl group, and an N-methyl-N-alkyl amino group\n- The nitrogen on the ring is connected to a methyl group and a long alkyl chain (appears to be a straight chain without branching or an NH2 group at the end)\n\nIn the wrong SMILES, the long chain ends with `[CH:2]([NH2:25])[CH3:1]`, meaning there's a branching point with an NH2 and a CH3 at the end of the chain. In the image, the chain is simply a straight unbranched alkyl chain with no NH2 group.\n\nThe fix is to remove the NH2 group from atom 2.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "NH2" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000072", + "op_type": "change_charge", + "image_path": "images/000072.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][NH+:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000064", + "op_type": "remove_bond", + "image_path": "images/000064.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]2[cH:14][c:15]([CH2:16][OH:17])[c:18]1[c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]2", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I see a molecule with:\n- An aromatic ring with substituents: an acetylamino group (NHAc), a hydroxymethyl group (CH2OH), and a nitrogen with a methyl and a long alkyl chain\n- The nitrogen is directly attached to the aromatic ring (no saturated ring)\n\nIn the wrong SMILES, atoms 7-10 form a saturated ring (cyclohexane-like ring fused to the aromatic ring) with the nitrogen. In the correct molecule from the image, there is no such saturated ring \u2014 the long alkyl chain is simply a straight chain attached to the nitrogen.\n\nThe issue is the bond between atom 7 (CH) and atom 18 (aromatic carbon) that closes the saturated ring. Removing this bond and the ring, the chain becomes a straight open chain attached to nitrogen.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 18}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 18 + } + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000076", + "op_type": "remove_functional_group", + "image_path": "images/000076.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:30])[cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "Looking at the image, the correct molecule has only one fluorine on the phenyl ring (at the para position), while the wrong SMILES has two fluorines (atoms :27 and :30).\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 30}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 30 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000062", + "op_type": "change_charge", + "image_path": "images/000062.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH+:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 11}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 11 + } + }, + "restored_smiles": "C.CC(=O)Nc1cccc(CO)c1.CCCCCCCCCC", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000077", + "op_type": "add_functional_group", + "image_path": "images/000077.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a fluorine substituent on the phenyl ring attached to the carbonyl chain (para position). The wrong SMILES has an unsubstituted phenyl ring at that position.\n\nComparing the two structures:\n- The wrong SMILES has `[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1` \u2014 an unsubstituted phenyl ring\n- The correct molecule shows a para-fluorophenyl group\n\nThe atom at the para position (map_num 26) needs a fluorine substituent.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 26}, \"group\": \"F\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 26 + }, + "group": "F" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000071", + "op_type": "add_atom", + "image_path": "images/000071.png", + "wrong_smiles_mapped": "[CH2:1]([CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[C:11](=[O:12])[NH:13][CH2:14][N:15]2[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a carbonyl group (C=O) connecting the chain to the fluorophenyl ring. In the wrong SMILES, atom :1 is a CH2 group, but in the correct structure it should be a carbonyl carbon (C=O).\n\nThe image shows: F-phenyl-C(=O)-CH2-CH2-CH2-N(piperidine)...\n\nIn the wrong SMILES, the chain from the phenyl ring is: [CH2:1]([CH2:2][CH2:3][CH2:4][N:5]...)[c:22]...\n\nBut it should be a C(=O) at position :1, meaning atom :1 needs to be changed from CH2 to a ketone carbon. I need to change atom :1 to a carbonyl carbon by adding an oxygen with a double bond.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CHO\"}\n\nWait, let me reconsider. The atom :1 is CH2 but should be C(=O). I need to change the atom to have a double-bonded oxygen. The simplest fix is to change atom :1 from CH2 to C with a =O attached.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}\n\nHmm, but that alone won't add the =O. Let me reconsider \u2014 I need to add an oxygen double bond to atom 1.\n\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000068", + "op_type": "move_substituent", + "image_path": "images/000068.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][cH:15][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]1[CH2:16][OH:17]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "Looking at the image, I can see the correct molecule has the hydroxymethyl group (CH2OH) on the meta position relative to the N(CH3)(decyl) group, and the acetamido group on the other meta position. The aromatic ring has substituents at positions that give a 1,3,5-trisubstituted pattern.\n\nComparing the wrong SMILES with the image, the alkyl chain in the wrong SMILES has 9 carbons (nonyl) connecting to the nitrogen, but the image shows a longer chain with 10 carbons (decyl). The wrong SMILES chain is: CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2- (9 carbons), but the image shows 10 carbons in the chain.\n\nWait, let me recount. The wrong SMILES: [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10] \u2014 that's 10 carbons total (1 CH3 + 9 CH2), making it a decyl chain. \n\nLet me re-examine. The image shows 8 CH2 groups + 1 CH3 = nonyl (9 carbons). The wrong SMILES has CH3 + 9\u00d7CH2 = 10 carbons (decyl).\n\nSo the fix is to remove one CH2 from the chain to make it a nonyl group matching the image.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 10}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 10 + } + }, + "restored_smiles": "CCCCCCCCC.CNc1cccc(NC(C)=O)c1CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000073", + "op_type": "change_bond_order", + "image_path": "images/000073.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "Looking at the image, the correct molecule has a saturated chain (CH2-CH2-CH2) connecting the carbonyl to the piperidine nitrogen, not a CH=CH-CH2 (with a double bond) as in the wrong SMILES.\n\nThe wrong SMILES has a double bond between atoms :3 and :4 (`[CH:3]=[CH:4]`), but the correct molecule shows a single bond there (all single bonds in the chain).\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000080", + "op_type": "remove_atom", + "image_path": "images/000080.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH:22]([OH:31])[O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000074", + "op_type": "remove_bond", + "image_path": "images/000074.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][C:9]3([CH:10]1[CH2:11]2)[C:12](=[O:13])[NH:14][CH2:15][N:16]3[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a chain of three carbons (propyl chain) connecting the carbonyl group to the piperidine nitrogen, rather than the direct attachment shown in the wrong SMILES.\n\nIn the wrong SMILES, atom :3 (CH) is directly bonded to both the carbonyl carbon :2 and is part of the piperidine ring. In the correct structure, there's a three-carbon chain (CH2-CH2-CH2) between the carbonyl and the piperidine nitrogen :6.\n\nThe wrong SMILES has the carbonyl carbon :2 directly attached to CH :3, which is part of the ring. In the image, the carbonyl is connected via a -(CH2)3- chain to the nitrogen :6 of the piperidine ring, and atom :3 should be a CH2 (not CH) since it's no longer at a branch point but part of the chain.\n\nComparing more carefully: the wrong SMILES connects C:2 to C:3 which is in the piperidine ring. The correct molecule connects C:2 through additional CH2 groups to N:6. The key difference is that atom :10 (CH) should be a CH2 \u2014 it shouldn't be bonded to C:3. Instead, C:3 is part of the open chain.\n\nThe simplest fix: the bond between atom :3 and atom :10 needs to be removed, making :3 a CH2 in the chain and :10 a CH2 in the ring.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 10}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 10 + } + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000081", + "op_type": "add_atom", + "image_path": "images/000081.png", + "wrong_smiles_mapped": "[OH:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([O:7][CH3:8])[c:9]1[O:10][CH3:11])-[c:12]1[cH:13][c:14]3[c:15]([cH:16][c:17]1[C:18](=[O:19])[CH:20]1[CH2:21][O:22][C:23](=[O:24])[CH:25]1[CH2:26]2)[O:27][CH2:28][O:29]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "Looking at the image, I can see the correct molecule has three methoxy (OCH3) groups on the right-hand ring, plus the methylenedioxy group on the left ring. The wrong SMILES has only two methoxy groups and one hydroxyl (OH) group at position 1.\n\nComparing the image to the wrong SMILES: the OH group at atom map 1 should be an OCH3 group instead.\n\n```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000078", + "op_type": "move_substituent", + "image_path": "images/000078.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][c:25]([F:27])[cH:26][cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "Looking at the image, I can see the correct molecule has the fluorine substituent at the para position of the phenyl ring attached to the carbonyl group.\n\nIn the wrong SMILES, the fluorine is at the meta position (attached to atom :25, which is meta relative to the attachment point :23).\n\nLet me trace the ring in the wrong SMILES: c:23 \u2192 c:24 \u2192 c:25(F) \u2192 c:26 \u2192 c:28 \u2192 c:29 \u2192 back to c:23. The carbonyl is attached at :23, and F is on :25 (two carbons away = meta).\n\nIn the image, the F is at the para position (opposite the attachment point). That would be atom :28 (three carbons away from :23 going around the ring: :23\u2192:24\u2192:25\u2192:26 or :23\u2192:29\u2192:28). Looking at the numbering: :23\u2192:29\u2192:28 is two steps, and :23\u2192:24\u2192:25\u2192:26 is three steps \u2014 so :26 or :28 could be para depending on ring connectivity.\n\nThe ring is: :23-:24-:25-:26-:28-:29-:23. So para to :23 is :26 (position 4 in a 6-membered ring: :23(1), :24(2), :25(3), :26(4), :28(5), :29(6)).\n\nI need to move the fluorine from atom :25 to atom :26.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 27}, \"from_atom\": {\"map_num\": 25}, \"to_atom\": {\"map_num\": 26}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 27 + }, + "from_atom": { + "map_num": 25 + }, + "to_atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000075", + "op_type": "add_bond", + "image_path": "images/000075.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[O:1]=[CH:2][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a ketone (C=O) connecting the fluorophenyl group to the chain, rather than an aldehyde (CHO). Specifically, in the wrong SMILES, atom :2 is a CH (aldehyde), but in the correct molecule it should be a carbonyl carbon (C=O) connected to the fluorophenyl ring and the chain.\n\nThe wrong SMILES has `[O:1]=[CH:2][c:23]1...` (an aldehyde), but the image shows a ketone where that carbon is bonded to both the aromatic ring and the propyl chain. The chain `[CH3:3][CH2:4][CH2:5]` in the wrong SMILES should connect to atom :2 to form the ketone.\n\nSo I need to add a bond between atom :3 (currently CH3 at the end of the chain) and atom :2 (the aldehyde carbon), making it a ketone. But looking more carefully, the chain should be: fluorophenyl-C(=O)-CH2-CH2-CH2-N...\n\nThe wrong SMILES has the chain as CH3-CH2-CH2-N (atoms 3,4,5,6) disconnected from the aldehyde O=CH-aryl. In the correct molecule, atom :2 should connect to atom :3, forming the ketone bridge.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000085", + "op_type": "add_bond", + "image_path": "images/000085.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3.[OH:8][CH3:9]", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "Looking at the image, the correct molecule has three methoxy (OCH3) groups on the right-hand ring. In the wrong SMILES, there are only two methoxy groups on that ring (at positions 2-1 and 11-12), and there's a disconnected fragment `[OH:8][CH3:9]` that should instead be attached to the ring.\n\nExamining the ring: atoms 3, 4, 5, 6, 7, 10 form the right aromatic ring. In the wrong SMILES, atom 10 has OMe (via O:11, CH3:12) and atom 3 has OMe (via O:2, CH3:1). The image shows three OMe groups on this ring. Atom 5 (between atoms 4 and 6) currently has no substituent but should bear the third OMe group.\n\nThe disconnected `[OH:8][CH3:9]` represents the missing methoxy group. I need to attach it to atom 5.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 5}, \"group\": \"OH\"}\n\nWait, let me reconsider. The fragment [OH:8][CH3:9] is already present. I need to connect O:8 to atom 5 and remove the H from O:8 to make it an ether linkage.\n\nThe simplest fix: add a bond between atom 5 and atom 8 to connect the methoxy group to the ring.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 8}}, \"order\": \"SINGLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000079", + "op_type": "change_atom_element", + "image_path": "images/000079.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][S:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "Looking at the image, I can see the correct molecule has a lactone ring (five-membered ring with O and C=O), not a thiolactone. The wrong SMILES contains a sulfur atom (S at map_num 23) that should be an oxygen atom.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 23}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 23 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000083", + "op_type": "change_bond_order", + "image_path": "images/000083.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[CH:19]([OH:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "Looking at the image, I can see the correct molecule has a ketone (C=O) group where the wrong SMILES has a hydroxyl (C-OH) group. Specifically, atom 19 in the wrong SMILES is `[CH:19]([OH:20])`, but in the correct image, this position is a carbonyl (C=O), i.e., a ketone.\n\nSo the fix is to remove the OH group at atom 19 and change the bond between atom 19 and atom 20 to reflect a ketone. Looking more carefully:\n\n- Atom 19 is `[CH:19]([OH:20])` \u2014 this is a carbon with an OH attached.\n- In the correct molecule, this should be a C=O (ketone).\n\nThis means I need to change the bond between atom 19 and atom 20 from single to double, and change atom 20 from OH to O (removing the H). But the simplest single action is to remove the OH group and note that the carbon needs a =O instead.\n\nLooking at the available actions, I can use `RemoveGroup` to remove OH from atom 19, but that would leave the carbon without the oxygen. Let me reconsider.\n\nThe carbon at atom 19 has an OH group (atom 20). In the correct structure, it should be a C=O (double bond to oxygen). I need to change the bond between atoms 19 and 20 from SINGLE to DOUBLE, and the oxygen loses its hydrogen. But that's two changes.\n\nActually, the `ChangeBond` action changes the bond order, and making O-H implicit would follow from making it a double bond C=O. The most direct single fix: change the bond between atom 19 and atom 20 from SINGLE to DOUBLE.\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 19}, \"atom2\": {\"map_num\": 20}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 19 + }, + "atom2": { + "map_num": 20 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000088", + "op_type": "change_atom_element", + "image_path": "images/000088.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([NH:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the wrong SMILES, I need to compare it with the image.\n\nThe wrong SMILES has `[NH:18]` connecting the piperazine nitrogen (atom 17) to the `[CH:19]=[CH:20]` cinnamyl group via an NH linkage.\n\nIn the image, the cinnamyl group is connected to the piperazine nitrogen via a CH2 group (N-CH2-CH=CH-Ph), not via NH-CH=CH-Ph.\n\nSo atom 18 (currently NH) should be changed to a CH2 group \u2014 i.e., the element should be changed from N to C.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 18}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 18 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000082", + "op_type": "change_charge", + "image_path": "images/000082.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[OH+:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 25}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 25 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000087", + "op_type": "move_substituent", + "image_path": "images/000087.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:26]1([CH2:21][CH2:22][O:23][C:24]1=[O:25])[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "Looking at the wrong SMILES and comparing it to the image:\n\nThe wrong SMILES has atom map :5 and :6 connected by an aromatic bond (part of the aromatic ring), and the bond between atoms :6 and :27 is a single bond (indicated by `-`). Similarly, atoms :2 and :26/:27 connectivity needs checking.\n\nLet me trace through more carefully. The image shows a large ring system where the central ring contains double bonds (it's not fully saturated). Specifically, looking at the image, there's a C=C double bond in the large ring between what corresponds to atoms :5 and :6 in the SMILES.\n\nIn the wrong SMILES, atoms :5 and :6 are part of an aromatic ring `[c:5]2[c:6]`, and atom :6 connects to :27 via `[CH2:27]2` (ring closure). But in the image, the bond between :6 and :27 appears to be a double bond (C=C), and :27 should be a CH (not CH2).\n\nLooking more carefully at the central macrocyclic ring in the image, there's a double bond between the carbon connecting to the methylenedioxy-phenyl ring and the adjacent carbon. In the SMILES, atom :27 is `[CH2:27]` connecting atoms :6 and :2 (ring closure 2). The image shows this should be a `=CH-` (double bond to atom :6).\n\nThis means the bond between :6 and :27 should be a double bond, and :27 changes from CH2 to CH.\n\nBut since I can only output one action, the key structural difference is the bond order between atoms :6 and :27.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 27}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 27 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "No bond between atom idx 5 and 26" + }, + { + "id": "000089", + "op_type": "remove_atom", + "image_path": "images/000089.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH:27]([CH3:31])[CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, I see a piperazine ring connected to a CH(Ar)(Ar) group and an allyl-phenyl group. The correct molecule has a standard piperazine (two nitrogens, all CH2 groups in the ring), but the wrong SMILES has a CH with a CH3 branch at atom 27 (and atom 31 for the methyl).\n\nIn the image, the piperazine ring is a simple 6-membered ring with no methyl substituent. The wrong SMILES has a methyl group on atom 27. I need to remove that methyl group (atom 31) to make atom 27 a regular CH2.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000090", + "op_type": "add_atom", + "image_path": "images/000090.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, the correct molecule has a CH group bonded to TWO fluorophenyl rings and a piperazine nitrogen. The wrong SMILES only has one fluorophenyl ring on the CH group \u2014 the other ring attached to atom :4 is an unsubstituted phenyl ring (atoms :1, :2, :3, :28, :29).\n\nIn the image, that second phenyl ring also has a fluorine at the para position. So I need to add a fluorine to the phenyl ring attached via atom :4. The para position on that ring (relative to atom :4) would be atom :2.\n\nLooking at the ring: :4 \u2192 :28 \u2192 :29 \u2192 :1 \u2192 :2 \u2192 :3 \u2192 :4. The para position to :4 is :1.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"F\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "F" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000084", + "op_type": "remove_bond", + "image_path": "images/000084.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([c:17]4[c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[C:26]41[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "Looking at the image, I can see the correct molecule has a double bond between the two carbon atoms in the large ring connecting the two aromatic systems (making it a typical colchicine-like tropolone/cycloheptane system with a C=C bond).\n\nComparing the wrong SMILES to the image: the bond between atoms 6 and 27 (the CH2 group connecting the aromatic ring to the rest of the macrocycle) should be a double bond, and atom 27 should lose a hydrogen (becoming CH instead of CH2, or rather =CH2 becoming =CH\u2014but looking more carefully):\n\nThe wrong SMILES has `[CH2:27]2` connecting atom 6 to atom 2's ring closure. In the image, there's a C=C double bond in the large ring between the two aromatic portions. Specifically, the bond between atom 2 (part of the ring) and atom 27 should be a double bond, and correspondingly atom 27 should be CH (not CH2).\n\nLooking more carefully at the connectivity: atoms 6 and 27 are bonded via the `[CH2:27]2` ring closure to atom 5. The image shows a double bond between these carbons in the medium ring.\n\nThe fix is to change the single bond between atoms 5 and 27 to a double bond (the ring closure bond).\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 27}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 27 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Can't kekulize mol. Unkekulized atoms: 2 3 5 6 9 12 13 14 15 16 17" + }, + { + "id": "000070", + "op_type": "remove_atom", + "image_path": "images/000070.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH:7]([OH:30])[CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "OH" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000094", + "op_type": "add_bond", + "image_path": "images/000094.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1.[cH:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, I see a molecule with:\n- A piperazine ring\n- One nitrogen connected to a cinnamyl group (CH2-CH=CH-phenyl)\n- The other nitrogen connected to a CH group bearing two 4-fluorophenyl groups (a bis(4-fluorophenyl)methyl group)\n\nIn the wrong SMILES, the second 4-fluorophenyl group (atoms 7-13) is disconnected \u2014 it's a separate fragment not bonded to anything in the main molecule. It should be connected to the CH2 group (atom 6) to form a CHR2 group, making atom 6 a CH that bridges both 4-fluorophenyl rings and connects to the piperazine nitrogen.\n\nLooking more carefully: atom 6 is `[CH2:6]` connected to N:14 of piperazine and to c:5 of one fluorophenyl. The second fluorophenyl (c:10) needs to be bonded to atom 6 as well, making it a CH (not CH2) bearing two aryl groups.\n\n```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 10}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 10 + } + }, + "order": "SINGLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (AddBond): Can't kekulize mol. Unkekulized atoms: 23 24 25 28 29" + }, + { + "id": "000095", + "op_type": "remove_functional_group", + "image_path": "images/000095.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)([N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[CH3:31])[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, the correct molecule has a CH (methine) center connected to two 4-fluorophenyl groups and a piperazine nitrogen \u2014 no methyl group on that carbon. The wrong SMILES has a methyl group (CH3, atom 31) on the central carbon (atom 6), making it a quaternary carbon.\n\nThe fix is to remove the methyl group (atom 31).\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000091", + "op_type": "change_charge", + "image_path": "images/000091.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[NH+:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, the correct molecule has a neutral nitrogen in the piperazine ring where the CH group is attached, and the bond between C19 and C20 should be a double bond (trans-cinnamyl group).\n\nComparing the wrong SMILES to the image:\n\n- The wrong SMILES has `[NH+:14]` (positively charged nitrogen), but the image shows a neutral nitrogen.\n- The wrong SMILES has `[CH:19]=[CH:20]` which is already a double bond \u2014 that's correct for the cinnamyl group.\n\nThe key difference is the charged nitrogen at atom 14. In the image, it's a neutral tertiary amine, not a protonated one.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 14}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000086", + "op_type": "remove_functional_group", + "image_path": "images/000086.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:21]1([NH2:31])[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "Looking at the wrong SMILES, I can see it has an NH2 group at atom map number 31. Comparing with the image of the correct molecule, there is no NH2 group present \u2014 that position should just be a CH2 (or similar carbon without the amine).\n\nThe correct molecule in the image shows no nitrogen-containing groups. The NH2 at atom 31 (attached to atom 21) needs to be removed.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 21}, \"group\": \"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 21 + }, + "group": "NH2" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000099", + "op_type": "remove_atom", + "image_path": "images/000099.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH2:8][CH3:25])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the wrong SMILES, I need to identify the difference from the correct molecule shown in the image.\n\nThe wrong SMILES has three ethoxy groups on the phosphorus: `[O:3][CH2:2][CH3:1]`, `[O:6][CH2:7][CH2:8][CH3:25]`, and `[O:9]` connecting to the naphthalimide nitrogen.\n\nIn the image, I can see the phosphorus has two ethoxy groups (`OEt`) and one `=O`, connected via oxygen to the naphthalimide nitrogen. The second ethoxy group `[O:6][CH2:7][CH2:8][CH3:25]` has an ethyl chain (CH2CH2CH3 = propyl, 3 carbons), but in the image both alkoxy groups appear to be ethoxy (OEt, 2 carbons each).\n\nLooking more carefully at the wrong SMILES: `[O:6][CH2:7][CH2:8][CH3:25]` \u2014 this is a propoxy group (O-CH2-CH2-CH3), but the image shows an ethoxy group (O-CH2-CH3).\n\nThe fix is to remove atom 8 (the extra CH2), making the chain O-CH2-CH3 instead of O-CH2-CH2-CH3.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 8}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 8 + } + }, + "restored_smiles": "C.CCOP(=O)(OC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000100", + "op_type": "add_atom", + "image_path": "images/000100.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4]([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the wrong SMILES, the phosphorus atom (map_num 4) has three oxygen substituents but no double-bonded oxygen for the P=O group. In the image, I can see the phosphorus has a P=O (shown in the lower-left area of the molecule).\n\nThe wrong SMILES has P with three single-bonded oxygens (O at map 3, O at map 5, O at map 8), but the image shows P with a double-bonded O (the P=O), two O-ethyl groups, and one O connecting to N. Currently, the bond between P (map 4) and O (map 5) is single, but looking at the image, atom map 5 corresponds to the P=O oxygen.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 5}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 4 O, 3, is greater than permitted" + }, + { + "id": "000092", + "op_type": "change_bond_order", + "image_path": "images/000092.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH:15]=[CH:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the wrong SMILES, I see it contains an imidazole-like ring (N-CH=CH-N pattern with atoms 14-17), but the correct molecule in the image shows a piperazine ring (a six-membered ring with two nitrogens, fully saturated).\n\nThe wrong SMILES has a 4-membered fragment: N:14, CH:15=CH:16, N:17, CH2:27, CH2:28 forming a 5-membered ring with two double bonds. The image shows a piperazine (6-membered ring with two N atoms and four CH2 groups).\n\nThe key difference is that the bond between atoms 15 and 16 is a double bond in the wrong SMILES (CH=CH), but in the correct piperazine structure it should be a single bond (making them CH2-CH2).\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 15}, \"atom2\": {\"map_num\": 16}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 15 + }, + "atom2": { + "map_num": 16 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000093", + "op_type": "remove_bond", + "image_path": "images/000093.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]2[cH:29][c:30]1[CH:16]1[CH2:15][N:14]([CH:6]2[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[CH2:28][CH2:27][N:17]1[CH2:18][CH:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, I see a molecule with:\n- A piperazine ring\n- One nitrogen connected to a CH(Ar)(Ar) group bearing two 4-fluorophenyl rings\n- The other nitrogen connected to a CH2-CH=CH-phenyl (cinnamyl) group\n\nIn the wrong SMILES, the CH at atom :16 bridges between the two aromatic rings (atoms :5/:30 and connected to N:14), forming a fused ring system with atoms :29 and :30. This means atoms :29 and :30 are part of the first fluorophenyl ring, creating a fused/bridged structure.\n\nIn the correct molecule, the two fluorophenyl rings are separate, both attached to the CH (atom :16), not fused. The bond between atoms :29 and :5 (which creates the bridged ring) needs to be removed, and instead atom :29 should be a separate part of a second 4-fluorophenyl group.\n\nThe key difference: in the wrong SMILES, atom :29 is bonded to atom :5, making it part of the first phenyl ring. In the correct structure, there's no bond between :29 and :5 \u2014 instead :29 should connect to a full second 4-fluorophenyl ring hanging off :16.\n\nThe simplest fix is to remove the bond between atoms :29 and :5, breaking the fused system, and recognize that atom :30 and :29 need restructuring. But looking more carefully, the wrong SMILES has atoms :29 and :30 bridging the ring. Removing the bond between :29 and :5 would leave :29 as a CH with only two connections.\n\nThe core issue is that the bond between :5 and :29 should not exist \u2014 it fuses what should be two separate phenyl rings.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 29}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 29 + } + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (RemoveBond): Can't kekulize mol. Unkekulized atoms: 1 2 3 4 6" + }, + { + "id": "000098", + "op_type": "change_atom_element", + "image_path": "images/000098.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[S:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the wrong SMILES, I see the phosphorus atom at position 4 is connected to a sulfur atom (S, map_num 9) which then connects to the nitrogen (N, map_num 10). In the correct molecule shown in the image, the phosphorus connects to an oxygen which connects to the nitrogen \u2014 there's no sulfur in the molecule.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 9 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000097", + "op_type": "move_substituent", + "image_path": "images/000097.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:9]2[cH:8][cH:7][cH:13][cH:12][c:10]2[F:11])[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, I see a molecule with:\n- A CH group connected to two 4-fluorophenyl rings and a piperazine nitrogen\n- The piperazine's other nitrogen is connected to a CH2CH=CH-phenyl (cinnamyl) group with trans geometry\n\nComparing with the wrong SMILES:\n- The wrong SMILES has one fluorophenyl ring with F at the ortho position (atom :11 on atom :10, which is adjacent to :9 where the CH is attached)\n- In the image, both fluorophenyl rings have F at the para position\n\nSo the F (atom :11) needs to move from the ortho position (atom :10) to the para position (atom :13) on the second ring.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 13 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000096", + "op_type": "add_functional_group", + "image_path": "images/000096.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "Looking at the image, the correct molecule has a CH group connected to two 4-fluorophenyl rings and a piperazine. The wrong SMILES only has one fluorophenyl ring \u2014 the other ring (atoms 1,2,3,28,29 and atom 4) is an unsubstituted phenyl ring. In the correct molecule, that second phenyl ring should also be a 4-fluorophenyl ring.\n\nThe unsubstituted phenyl ring in the wrong SMILES is: c1(:[1]) - c(:[2]) - c(:[3]) - c(:[4]) - c(:[28]) - c(:[29]). The para position to atom 4 is atom 2. I need to add a fluorine to atom 2.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"F\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "F" + }, + "restored_smiles": "Fc1ccc(C(c2cccc(F)c2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000104", + "op_type": "add_bond", + "image_path": "images/000104.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4](=[O:5])[O:6][CH2:7][CH3:8].[OH:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the image, I can see the nitrogen atom (N, shown in blue) is connected to the phosphate group's oxygen, not through an OH group. In the wrong SMILES, atom :9 is an OH group bonded to the nitrogen, but in the correct molecule, the N-O bond connects directly to the phosphate oxygen (atom :6).\n\nThe wrong SMILES has an extra OH group at atom :9 with the nitrogen bearing an OH substituent. In the correct structure, the nitrogen (atom :10) is directly bonded to the oxygen (atom :6) of the phosphate group, and there's no separate OH on nitrogen.\n\nComparing the two structures:\n- Wrong: The nitrogen :10 has an OH (:9) attached, and the phosphate oxygen :6 has an H\n- Correct: The nitrogen :10 is directly bonded to oxygen :6 (which bridges to phosphorus), and there's no OH on nitrogen\n\nThis means we need to remove the hydroxyl group (atom :9) from nitrogen and add a bond from nitrogen :10 to oxygen :6.\n\nBut since we can only output a single action, the key difference is removing the OH from nitrogen :10, since the N-O-P connection needs to be established. Looking more carefully, the simplest single fix is to remove atom :9 (the OH) and add a bond between :10 and :6.\n\nThe most appropriate single action: Remove the OH group from the nitrogen anchor.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 10}, \"group\": \"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 10 + }, + "group": "OH" + }, + "restored_smiles": "CCO[PH](=O)OCC.O=C1[N]C(=O)c2cccc3cccc1c23", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000109", + "op_type": "change_atom_element", + "image_path": "images/000109.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES:\n\nThe image shows a glycolipid with two fatty acid chains connected to a glycerol, which is linked to a sugar sulfonate. \n\nIn the wrong SMILES, the upper chain (atoms 1-18) contains a sulfur atom at position 7 (`[S:7]`), making it a thioether. In the correct molecule shown in the image, both chains are simple hydrocarbon fatty acid chains \u2014 there's no sulfur in the chain. That S:7 should be a CH2 group (a regular carbon in the chain).\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000103", + "op_type": "remove_bond", + "image_path": "images/000103.png", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]2[C:11](=[O:12])[c:13]3[c:14]1[cH:15][cH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([c:22]31)[C:23]2=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the wrong SMILES, I need to identify the phosphorus substituents. The phosphorus atom (map 4) currently has:\n- =O (map 5)\n- O-CH2-CH3 (maps 6, 7, 8)\n- Two ring O connections (maps 3 and 9)\n\nIn the image, the phosphorus has two ethoxy groups (OEt) plus the =O and the ring oxygen. Currently, the SMILES only shows one OEt group on phosphorus. The other oxygen (map 3) connects into the ring but in the image it should bear an ethyl group (OEt) as a separate substituent, meaning the phosphorus needs an additional OEt group.\n\nLooking more carefully: atom 6 is an oxygen connecting P to CH2CH3 (one OEt). The image shows two OEt groups on phosphorus. Currently atom 3 (O) bridges P back into the ring (CH2 groups 1,2). But in the image, there's no such CH2-CH2 bridge \u2014 instead that oxygen has its own ethyl group.\n\nSo the fix is to change atom 3's connection: instead of being part of the ring connecting to CH2 (atom 2), it should have an ethyl group. But since I can only output a single action, let me reconsider.\n\nComparing more carefully: the wrong SMILES has atoms 1 (CH2) and 2 (CH2) forming a bridge. In the image, there's no such CH2-CH2 bridge. Instead, the phosphorus oxygen (map 6) leads to OCH2CH3, and the other oxygen (map 3) also leads to OCH2CH3.\n\nThe simplest single fix: atom 1 (CH2) is bridging between atom 14 (aromatic) and atom 2. If I change atom 1's element to oxygen, that doesn't work structurally.\n\nActually, removing atom 2 would break the P-O-CH2-CH2 bridge into P-O-CH2 directly on the aromatic ring, giving an OEt-like group on the other oxygen. Let me reconsider \u2014 removing atom 1 would leave O(3)-CH2(2) as a separate ethyl-like piece.\n\nThe key difference: the wrong molecule has -O-CH2-CH2- bridging P to the aromatic ring, while the correct one has -O-CH2-CH3 (an ethoxy group not connected back to the ring). So I need to remove the bond between atom 1 and atom 14 to break the ring, and add an H to make CH3. This is effectively removing atom 1 from between atom 2 and atom 14, but as a single action:\n\nThe simplest fix is to remove atom 1, which breaks the CH2-CH2 bridge. Atom 2 then becomes a CH3 terminal group on O(3), giving the second OEt group.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 1}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 1 + } + }, + "restored_smiles": "CCOP(=O)(OC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000107", + "op_type": "move_substituent", + "image_path": "images/000107.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][n:10]1[c:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][c:17]([cH:22]2)[CH:18]=[CH:19][CH:20]=[c:21]3[c:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the image, I can see a molecule with a naphthalene-based ring system fused with a nitrogen-containing ring (a 1,8-naphthalimide derivative) where the nitrogen is connected to an oxygen that links to a diethoxyphosphoryl group.\n\nComparing the image to the wrong SMILES, the key issue is in the aromatic ring system. In the image, the naphthalene portion is fully aromatic, but in the wrong SMILES, atoms 18-21 have single/double bond alternation with explicit CH groups (`[CH:18]=[CH:19][CH:20]=[c:21]`), indicating non-aromatic carbons where there should be aromatic ones.\n\nSpecifically, looking at the bond between atoms 17 and 18: atom 18 is `[CH:18]` but in the correct molecule (image), this ring is aromatic. The bond between atoms 19 and 20 needs to be examined too.\n\nThe critical difference: in the wrong SMILES, the bond between atom 20 and atom 21 is represented as a double bond (`=`), but looking at the fully aromatic naphthalene in the image, the bond between atoms 18 and 19 is shown as a double bond (`[CH:18]=[CH:19]`), while in the correct aromatic structure these should all be aromatic bonds.\n\nLooking more carefully, the simplest single fix: atom 20 should be `cH` (aromatic) rather than `CH` (non-aromatic). But since we need one action, the core issue is that the bond between atoms 19 and 20 should be a double bond to restore proper aromaticity/conjugation matching the image.\n\nRe-examining: the wrong SMILES has `[CH:18]=[CH:19][CH:20]=[c:21]` \u2014 bonds 18=19 (double), 19-20 (single), 20=21 (double). In the image, the correct structure shows 18-19 (single), 19=20 (double), 20-21 (single) pattern, i.e., the bond between 18 and 19 should be single, and 19-20 should be double.\n\nThis is an E/Z or bond pattern shift \u2014 effectively swapping bond orders. The simplest fix is:\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 18}, \"atom2\": {\"map_num\": 19}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 18 + }, + "atom2": { + "map_num": 19 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCOP(=O)(OCC)On1c(=O)c2c3cc(cc(c3)c1=O)CCC=2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000101", + "op_type": "change_charge", + "image_path": "images/000101.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][OH+:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":3},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000108", + "op_type": "swap_substituents", + "image_path": "images/000108.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][C:22]1=[C:13]2[C:11](=[O:12])[N:10]3[C:17](=[CH:16][CH:15]=[CH:14]2)[CH:18]=[CH:19][CH:20]=[C:21]1[C:23]3=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the image, I can see a 1,8-naphthalimide derivative where the nitrogen is connected to an oxygen that links to the phosphonate group. The correct molecule has a CH2 group between the nitrogen's oxygen and the phosphorus.\n\nComparing the wrong SMILES to the image:\n\nIn the wrong SMILES, the phosphorus atom (:4) is directly bonded to O(:9), which is directly bonded to C(:22) in the ring system. \n\nIn the image, there's a CH2 group between the O-P linkage and the N atom \u2014 specifically, the O(:9) connects to a CH2 which then connects to N(:10), not directly from O(:9) to the ring carbon C(:22).\n\nActually, let me re-examine. The image shows the P-O connects to a CH2 group, and that CH2 connects to N. In the wrong SMILES, O:9 connects directly to C:22 (a ring carbon). But in the correct structure, O:9 should connect to a CH2 which connects to N:10.\n\nLooking more carefully at the image: the nitrogen is part of the naphthalimide ring and has a bond going to O-P(=O)(OEt)2 directly. There's no extra CH2 between N and O-P.\n\nRe-examining: The wrong SMILES has O:6 bonded to the ethyl group (CH2CH3) as one substituent, O:3 bonded to another ethyl, and O:9 bonded to C:22 in the aromatic ring. The image shows O:9 bonded to N, not to a ring carbon.\n\nThe issue is that O:9 should be bonded to N:10 instead of C:22.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 22}, \"to_atom\": {\"map_num\": 10}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 22 + }, + "to_atom": { + "map_num": 10 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 13 N, 4, is greater than permitted" + }, + { + "id": "000110", + "op_type": "remove_atom", + "image_path": "images/000110.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[C:35]([OH:36])([CH3:57])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I need to compare the correct molecule with the wrong SMILES.\n\nThe correct molecule shows a sugar ring where all carbons have standard hydroxyl groups - there's no methyl group attached to the ring carbon. In the wrong SMILES, atom 35 is `C([OH:36])([CH3:57])` - a quaternary carbon bearing both an OH and a CH3 group.\n\nIn the image, that carbon on the sugar ring clearly has just an H and OH (a typical CHOH of a pyranose ring), not a tertiary carbon with a methyl group.\n\nThe fix is to remove the CH3 group (atom map 57) from atom 35.\n\n```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 35}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 35 + }, + "group": "CH3" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000112", + "op_type": "change_charge", + "image_path": "images/000112.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[OH+:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to identify the difference.\n\nIn the wrong SMILES, atom 26 is `[OH+:26]`, which represents a protonated oxygen in the sugar ring. In the correct molecule shown in the image, this should be a normal ring oxygen `O` with no charge.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 26}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 26 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000111", + "op_type": "add_atom", + "image_path": "images/000111.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][SH:29](=[O:30])=[O:31])[CH:32]([OH:33])[CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I can see a sulfonate group (SO\u2083H) on the sugar moiety. In the wrong SMILES, atom 29 is `[SH]` with two double-bonded oxygens (=O), giving a sulfinic acid-like group. The correct molecule has a sulfonic acid group, which requires three oxygens on sulfur \u2014 the two =O plus an OH.\n\nThe current SMILES has `[SH:29](=[O:30])=[O:31]`, but it should be `[S:29](=[O:30])(=[O:31])[OH]` \u2014 i.e., the SH needs to lose its H and gain an OH group, effectively adding one more oxygen.\n\nThe fix is to add an OH group to the sulfur atom (map_num 29):\n\n```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 29}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 29 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000113", + "op_type": "change_bond_order", + "image_path": "images/000113.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I can see the correct molecule has two saturated fatty acid chains (no double bonds). The wrong SMILES has a double bond between atoms 16 and 17 in the upper chain.\n\nI need to change the double bond between atoms 16 and 17 to a single bond.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 16}, \"atom2\": {\"map_num\": 17}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 16 + }, + "atom2": { + "map_num": 17 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000116", + "op_type": "remove_functional_group", + "image_path": "images/000116.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[Br:57]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 57}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 57 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000105", + "op_type": "remove_functional_group", + "image_path": "images/000105.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][c:15]([Cl:25])[cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the image, I see the correct molecule is a naphthalimide derivative with a diethoxyphosphoryloxy group on the nitrogen, and no chlorine substituent on the aromatic ring.\n\nThe wrong SMILES has a Cl atom (map_num 25) attached to the aromatic ring at position 15. The correct molecule shown in the image has no such chlorine \u2014 that position is simply a CH.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 15}, \"group\": \"Cl\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 15 + }, + "group": "Cl" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000102", + "op_type": "change_bond_order", + "image_path": "images/000102.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4]([OH:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the wrong SMILES, I see the phosphorus atom (map_num 4) is `[PH]`, meaning it has an explicit hydrogen. However, in the correct molecule shown in the image, the phosphorus has a double-bonded oxygen (P=O) instead of a P-H bond.\n\nThe wrong SMILES already has three oxygen substituents on P (O at map 3, O at map 6, O at map 9), plus the explicit H. The image shows a phosphonate with P=O, meaning the H on phosphorus should be replaced by adding a P=O group.\n\nLooking more carefully at the SMILES: the P atom (map 4) has `[PH]` with connections to O:3, O:6, and O:9. In the image, the phosphorus has a double-bonded oxygen (P=O) shown in red/yellow. So I need to remove the H from P and add a =O group. But since the atom already has an explicit H, changing the atom to remove the H and adding an oxygen would be the fix.\n\nThe simplest correction: the P-H should be a P=O. This can be done by changing the atom to remove H and adding an =O group.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 4}, \"group\": \"OH\"}\n\nWait \u2014 let me reconsider. The image shows P=O (a phosphoryl oxygen). The current SMILES has PH. I need to replace that H with a =O.\n\nThe best single action here is to add an oxygen with a double bond to the phosphorus anchor:\n\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 4}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000106", + "op_type": "add_functional_group", + "image_path": "images/000106.png", + "wrong_smiles_mapped": "[CH3:1][O:2][P:3](=[O:4])([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "Looking at the wrong SMILES, I see the phosphorus atom (map 8) is connected to the nitrogen via O-N, but in the image, the phosphorus group connects through O to the ring system, not directly to nitrogen.\n\nComparing the structures:\n\n- The wrong SMILES has: `[O:8][N:9]1` \u2014 meaning O:8 is bonded to N:9\n- In the image, the naphthalimide nitrogen is bonded to an O which connects to P, but looking more carefully, the connectivity shows the P group is connected via O to the carbon adjacent to N, not to N itself.\n\nActually, re-examining: in the wrong SMILES, the N is directly bonded to O:8 (which goes to P) and also to C:10 and C:22. In the image, N is bonded to C(=O), C(=O), and O-P. This matches. \n\nLet me look more carefully at the difference. The wrong SMILES has `[O:5][CH2:6][CH3:7]` \u2014 an ethoxy group on P. It also has `[CH3:1][O:2]` \u2014 a methoxy group on P. \n\nIn the image, I see TWO ethoxy groups (CH3CH2O-) on the phosphorus. The wrong SMILES has one methoxy (CH3-O-) and one ethoxy (CH3CH2-O-). So atom :1 (CH3) should have a CH2 inserted between it and O:2, or equivalently, we need to add a CH2 group.\n\nThe fix is to add a CH2 between CH3:1 and O:2, making it an ethoxy group. This can be done by adding an atom.\n\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n\nHmm, but that adds a carbon to CH3 without connecting to O. Let me reconsider.\n\nThe simplest fix: change the methoxy to ethoxy by adding a CH2 group between O:2 and CH3:1. Since we need to insert an atom, the better approach is to use AddGroup to add a CH3 to atom 1 (making it CH2-CH3 effectively) \u2014 but that changes connectivity.\n\nActually the simplest single action: the wrong molecule has CH3-O-P while it should be CH3CH2-O-P. Atom :1 is CH3 bonded to O:2. We need to insert a carbon. Using AddAtom on anchor O:2 won't help directly.\n\nThe most direct fix is adding a CH2 between atoms 1 and 2, but since we can't insert, let me reconsider: Change atom 1 from CH3 to CH2CH3 by adding a CH3 group to it.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000114", + "op_type": "remove_bond", + "image_path": "images/000114.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I need to compare the correct molecule with the wrong SMILES.\n\nThe correct molecule shows a glycerolipid with a sugar sulfonate head group. Let me trace the structure:\n\n- There's a glycerol backbone with two fatty acid ester chains and a sugar sulfonate group\n- The top chain appears to be a shorter chain with a cyclopropane ring (matching the wrong SMILES)\n- The bottom chain appears to be a longer straight chain (around 16 carbons)\n\nIn the wrong SMILES, the bottom acyl chain has 15 carbons in the chain (atoms 42-56). Looking at the image carefully, the bottom chain appears to have a longer chain - approximately 16 carbons total in the tail, meaning 17 carbons including the carbonyl carbon.\n\nComparing more carefully: the wrong SMILES bottom chain goes C(=O)-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3 (15 carbons after carbonyl = C16:0 chain, atoms 42-56).\n\nLooking at the image again, the bottom chain seems to have a cyclopropane ring as well, but actually no - the bottom chain is straight but longer.\n\nWait - let me re-examine. The top chain in the wrong SMILES has a cyclopropane ring (atoms 5-8). Looking at the image, the top chain has a cyclopropane ring. The bottom chain in the image looks straight.\n\nThe key difference: counting carbons in the bottom chain in the image, it appears to have one more CH2 group than what's in the wrong SMILES. The bottom chain needs an additional CH2.\n\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 55}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 55 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "CCCCC1CCC1CCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCC(C)C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000120", + "op_type": "change_atom_element", + "image_path": "images/000120.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[N:4]([OH:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 4}, \"group\": \"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 4 + }, + "group": "OH" + }, + "restored_smiles": "CC(=O)NN", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000121", + "op_type": "remove_atom", + "image_path": "images/000121.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[CH3:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 7}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000122", + "op_type": "add_atom", + "image_path": "images/000122.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CN(N)C=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000117", + "op_type": "add_functional_group", + "image_path": "images/000117.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH2:33][CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I need to compare the correct molecule with the wrong SMILES.\n\nThe image shows a glycolipid with a sugar ring connected to a glycerol backbone with two fatty acid chains. The sugar ring has multiple OH groups and a sulfonate group (SO3H).\n\nExamining the wrong SMILES carefully, I notice the sugar ring portion. In the wrong SMILES, the ring is: `[CH:25]1[O:26][CH:27]([CH2:28][S:29]...)[CH2:33][CH:34]([OH:35])[CH:36]1[OH:37]`\n\nThis gives a 5-membered ring: 25-26-27-33-34-36-25 (6 atoms in the ring path, so it's a 6-membered ring: 25, 26, 27, 33, 34, 36).\n\nLooking at the image, the sugar ring has OH groups on multiple carbons. In the image, I can count OH groups on the ring - there appear to be three OH groups on ring carbons plus the CH2-SO3H substituent.\n\nIn the wrong SMILES, atom 33 is `[CH2:33]` - but looking at the image, the corresponding position in the sugar ring should have an OH group (making it a CH with OH, typical of a sugar like glucose/galactose). The image shows a fully hydroxylated sugar (except for the position with CH2SO3H).\n\nSo atom 33 should be a CH with an OH group instead of a CH2. This means I need to add an OH group to atom 33.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 33}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 33 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000123", + "op_type": "change_charge", + "image_path": "images/000123.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[OH+:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000115", + "op_type": "add_bond", + "image_path": "images/000115.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I can see a glycerolipid with two acyl chains and a sugar sulfate group. The correct molecule has:\n\n- sn-1 position: an ester-linked acyl chain (connected to the top CH2 of glycerol)\n- sn-2 position: an ester-linked acyl chain (connected to the middle CH of glycerol)\n- sn-3 position: connected to the sugar sulfate via an oxygen\n\nIn the wrong SMILES, the sn-1 position has a formate ester (CHO - atom 18) instead of a full acyl chain ester. Looking at the image, the top chain is clearly a long fatty acid ester, not a formate.\n\nThe wrong SMILES has atom 18 as a CH (formate: `[CH:18](=[O:19])[O:20]`), while the first fragment `[CH3:1]...[CH3:17]` is a free heptadecane not connected to anything.\n\nTo fix this, I need to connect the free alkyl chain (atoms 1-17) to atom 18, making it a proper long-chain acyl group. Atom 18 should become a carbon connected to the alkyl chain, turning the formate into a long-chain fatty acid ester. This means adding a bond between atom 17 (the terminal CH3 of the free chain, which should become CH2) and atom 18.\n\nBut looking more carefully: the free chain is atoms 1-17 (17 carbons), and atom 18 is the carbonyl carbon. Adding a bond from atom 17 to atom 18 would give an 18-carbon acyl group total, but atom 17 is CH3. Actually, we need to connect them \u2014 atom 17 to atom 18 with a single bond.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 17}, \"atom2\": {\"map_num\": 18}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 17 + }, + "atom2": { + "map_num": 18 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000128", + "op_type": "add_functional_group", + "image_path": "images/000128.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CN(N)C=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000127", + "op_type": "remove_functional_group", + "image_path": "images/000127.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[NH2:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 7}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000118", + "op_type": "move_substituent", + "image_path": "images/000118.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][C:25]1([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH2:27][CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I need to compare the correct molecule with the wrong SMILES.\n\nThe correct molecule shows a glycerolipid with a sugar headgroup bearing a sulfonate group. Let me trace the structure carefully.\n\nIn the image, I can see two acyl chains. The top chain appears shorter and the bottom chain appears longer. Let me count the carbons in each chain from the image.\n\nThe wrong SMILES has:\n- Top chain (atoms 1-18): CH3-(CH2)16-C(=O)- \u2192 18 carbons total (C17 fatty acid chain + carbonyl) = stearoyl (C18:0)\n- Bottom chain (atoms 40-56): -C(=O)-(CH2)14-CH3 \u2192 16 carbons total = palmitoyl (C16:0)\n\nLooking at the image more carefully, the top chain looks shorter than the bottom chain. The top chain appears to have fewer carbons than the bottom, suggesting the chains should be swapped - the shorter chain on top and the longer chain on bottom.\n\nIn the wrong SMILES, the top chain has 17 carbons (C1-C17 + C18 carbonyl = C18:0) and the bottom has 15 carbons (C42-C56 + C40 carbonyl = C16:0). In the image, the bottom chain is clearly longer than the top chain, which matches. But let me look more carefully...\n\nActually, re-examining: the top chain in the image appears to have fewer CH2 groups than in the wrong SMILES. The bottom chain appears longer. Counting more carefully in the image, the top chain looks like about 14 carbons (palmitoyl, C16:0) and the bottom like 16 carbons (stearoyl, C18:0). This means the two chains are swapped compared to the wrong SMILES.\n\nThe fix is to swap the two acyl chain substituents on the glycerol backbone. The anchor atoms connecting to glycerol are atom 21 (connected to the top ester via O20) and atom 22 (connected to the bottom ester via O39). The substituents to swap would be at the ester oxygens.\n\nGiven the structure, swapping the substituents at the glycerol positions (atoms 21 and 22 carry the two different chains via their respective oxygens), the simplest correction is:\n\n```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 20}, \"atom2\": {\"map_num\": 39}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 20 + }, + "atom2": { + "map_num": 39 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1(CS(=O)(=O)O)OCC(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000129", + "op_type": "change_atom_element", + "image_path": "images/000129.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[N:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the wrong SMILES, I need to compare it with the correct molecule shown in the image.\n\nThe image shows a complex indole alkaloid (likely a Strychnos-type alkaloid) with an amide nitrogen connecting to the carbonyl. In the wrong SMILES, atom :20 is N and atom :21 is N, forming an N-N bond between the indole nitrogen and another nitrogen. \n\nIn the correct structure, the indole nitrogen (:20) should connect directly to the carbonyl carbon (:2) through the lactam ring, and there should not be two adjacent nitrogens. The atom at position :21 should be a carbon, not a nitrogen.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 21}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 21 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000119", + "op_type": "swap_substituents", + "image_path": "images/000119.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:35]1[CH:33]([OH:34])[CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH:25]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "Looking at the image, I need to compare the correct molecule with the wrong SMILES.\n\nThe correct molecule shows a glycerolipid with a sugar headgroup bearing a sulfate group. Let me trace the structure:\n\n- There's a glycerol backbone with two fatty acid chains (ester linkages) and a sugar moiety\n- The sugar has hydroxyl groups and a sulfate group (with S, showing SO3H on the CH2)\n\nExamining the wrong SMILES carefully, I see the sugar ring connectivity. In the wrong SMILES, atom 25 (CH) has an OH at position 36, and atom 35 (CH) connects to atom 33. Let me trace the ring: O:26 - CH:25(OH:36) - CH:37(OH:38) - CH:35(OH:34, connected to O:24) - CH:33(OH... wait, no, 33 has OH:34) - CH:27 - back to O:26.\n\nRing in wrong SMILES: O:26, CH:25, CH:37, CH:35, CH:33, CH:27 with CH:27 having CH2-SO3H.\n\nLooking at the image, the sulfate group is on the CH2 attached to the sugar. The sugar ring shows specific OH positions. Comparing the image carefully, I notice the carbon chain lengths.\n\nThe wrong SMILES has:\n- First chain (atoms 1-18): CH3-(CH2)16-C(=O)- \u2192 18 carbons (C18:0)\n- Second chain (atoms 42-56): -(CH2)13-CH3 \u2192 C15 chain, so C16:0 total with carbonyl\n\nLooking at the image, the bottom chain appears longer than the top chain. The top chain looks shorter. It seems the two acyl chains need to be swapped - the longer chain should be on the sn-2 position and the shorter on sn-1, or vice versa.\n\nActually, re-examining more carefully, the chain lengths in the image: the top chain has fewer carbons and the bottom chain has more. In the wrong SMILES, the top chain (atoms 1-17, C(=O)) is 17 CH2/CH3 + carbonyl = C18, and bottom chain is 15 CH2/CH3 + carbonyl = C16.\n\nThe image shows the bottom chain is clearly longer. So the chains appear swapped. Atoms 21 and 22 are the glycerol carbons bearing the two ester groups. The substituents (the two acyl chains) need to be swapped.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 21}, \"atom2\": {\"map_num\": 22}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 21 + }, + "atom2": { + "map_num": 22 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1C(O)C(O)OC(CS(=O)(=O)O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000130", + "op_type": "remove_atom", + "image_path": "images/000130.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH:6]([NH2:26])[CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 6}, \"group\": \"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 6 + }, + "group": "NH2" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000124", + "op_type": "change_bond_order", + "image_path": "images/000124.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([OH:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "Looking at the image, I see: NH2 connected to N, which is connected to CH3 (left/bottom) and to a carbon that has CH3 (top right) and =O (aldehyde/ketone oxygen).\n\nThe correct molecule is: CH3-N(NH2)-CH(=O)-CH3 \u2192 the carbon at position 2 should have a double bond to oxygen instead of a single bond to OH.\n\nComparing with the wrong SMILES: `[CH3:1][CH:2]([OH:3])[N:4]([CH3:5])[NH2:6]`\n\nThe wrong molecule has a single bond C-OH at atom 2, but the correct molecule has a C=O (carbonyl). This means I need to change the bond between atoms 2 and 3 from SINGLE to DOUBLE, and change atom 3 from OH to O.\n\nThe key fix: change the OH group to a =O by changing the bond order between atom 2 and atom 3 from single to double (the H on the OH is implicitly removed when the bond becomes double).\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000132", + "op_type": "change_charge", + "image_path": "images/000132.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the wrong SMILES, atom 1 is `[OH+]` which is a protonated oxygen with a double bond to C:2. In the correct molecule image, I can see a carbonyl group (C=O) at that position \u2014 a standard ketone oxygen, not a charged `[OH+]`.\n\nThe oxygen at atom map 1 should be a neutral oxygen with no charge.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000136", + "op_type": "remove_functional_group", + "image_path": "images/000136.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][C:4]2([F:26])[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 26}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000125", + "op_type": "remove_bond", + "image_path": "images/000125.png", + "wrong_smiles_mapped": "[CH2:1]1[C:2](=[O:3])[N:4]([NH2:6])[CH2:5]1", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "Looking at the image, I see an open-chain molecule: H\u2082N-N(CH\u2083)-CH=O, which is essentially an amino group (NH\u2082) attached to a nitrogen, which is also bonded to a methyl group (CH\u2083) and a formyl group (CHO).\n\nThe wrong SMILES represents a cyclic molecule (a 4-membered ring) with atoms 1, 2, 5 forming a ring with N(4). The correct molecule is open-chain, so I need to remove the bond that closes the ring between atoms 1 and 5.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 5}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 5 + } + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000126", + "op_type": "add_bond", + "image_path": "images/000126.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][N:4]([CH3:5])[NH2:6].[OH2:3]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "Looking at the image, I see a molecule with:\n- An NH2 group connected to a nitrogen\n- The nitrogen connected to a CH (methyl group below)\n- The nitrogen connected to a carbon that has a CH3 and a =O (aldehyde/carbonyl)\n\nSo the correct structure is: CH3-N(NH2)-CH(=O)-CH3, which is essentially N,N-substituted with a methyl, an NH2, and an acetaldehyde-like group.\n\nComparing with the wrong SMILES: `[CH3:1][CH2:2][N:4]([CH3:5])[NH2:6].[OH2:3]`\n\nThe wrong molecule has: CH3-CH2-N(CH3)(NH2) and a separate water molecule (OH2).\n\nThe correct molecule from the image shows the nitrogen connected to: NH2, CH3 (via CH2 is wrong - should be direct), and a CHO group (aldehyde) instead of CH3.\n\nThe key difference: atom map :5 is a CH3 that should be a CHO group, and atom :3 (water) and atom :2 (CH2) need adjustment.\n\nActually, let me re-examine. The wrong SMILES has CH3:5 where the image shows a CHO group. The water (O:3) is separate. The fix would be to change CH3:5 to CHO \u2014 replacing the methyl group with an aldehyde group.\n\nBut also, CH2:2 should be just CH2... Looking more carefully at the image, the N connects directly to the carbon bearing =O and CH3. So atom :2 (CH2) seems extra, and the O:3 is disconnected.\n\nThe simplest single action: Change atom :5 from CH3 to CHO, and handle the oxygen. But we need one action.\n\nThe core issue is that atom :5 (CH3) should have an aldehyde oxygen, and atom :3 (water) shouldn't be separate. This means we need to move the oxygen from being a standalone water to being bonded to atom :5.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 5}, \"group\": \"CH3\"}\n\nWait \u2014 let me reconsider. The simplest fix: change atom :5's CH3 to CHO.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"C\", \"charge\": 0}\n\nHmm, but that doesn't add the =O. Let me think about this as swapping: atom :3 (O as water) should bond to atom :5, and atom :5 should become CHO.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000139", + "op_type": "change_atom_element", + "image_path": "images/000139.png", + "wrong_smiles_mapped": "[F:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000140", + "op_type": "remove_atom", + "image_path": "images/000140.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH3:9]", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000133", + "op_type": "change_bond_order", + "image_path": "images/000133.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH2:7][CH:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the image, I can see the correct molecule has a double bond in the seven-membered ring region, appearing as a C=C double bond (the alkene visible in the left portion of the structure).\n\nComparing the wrong SMILES to the image, I need to identify where the structural difference is. The image shows a C=C double bond between carbons in the bridge/macrocyclic region (the left side with the zigzag alkene), while the wrong SMILES has all single bonds in that region.\n\nSpecifically, the bond between atoms mapped as :6 and :7 (CH2-CH2 in the oxygen-containing bridge) should include a double bond character elsewhere. Looking more carefully, the alkene is in the larger ring on the left side \u2014 between atoms :8 and :9, which in the wrong SMILES are CH2-CH2 but in the image one of these should be part of a C=C double bond.\n\nRe-examining: the double bond visible in the image is between atoms :8 and :9 (the left-side bridge). Changing this bond from single to double would also mean those carbons lose hydrogens (CH2 \u2192 CH).\n\nActually, looking more carefully at the wrong SMILES and the image, the bond between atoms :6 and :7 appears to be where the double bond should be \u2014 these are currently both CH2 groups connected by a single bond in the ether bridge region, but the image shows a C=C double bond there.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 9}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 9 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1CC2OCCC3=CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000134", + "op_type": "remove_bond", + "image_path": "images/000134.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH:3]2[CH:4]3[O:5][CH2:6][CH:7]=[C:8]4[CH:9]2[N:10]2[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]3[C@H:23]4[CH2:24][C@H:25]26", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the wrong SMILES and comparing it to the image:\n\nThe image shows a structure where the carbonyl (C=O) is part of a lactam connected to the nitrogen. Examining the wrong SMILES, atom :3 (CH) is between the carbonyl carbon :2 and atom :4. In the image, there's a CH2-CH2 pattern adjacent to the carbonyl and nitrogen, forming a six-membered lactam ring.\n\nComparing the connectivity carefully, in the wrong SMILES the bond between atoms :7 and :8 is a double bond (CH=C), representing the alkene. Looking at the image, the alkene is present but the bond between atoms :8 and :9 should be examined.\n\nThe key difference I can identify is that the bond between atom :2 (the carbonyl carbon) and atom :3 is a single bond in the wrong SMILES (C-CH), but looking more carefully at the structure, the issue is the bond between atoms :3 and :4. In the image, there's a CH2-CH2 linkage there, but in the wrong SMILES atom :3 is CH which participates in a bridged system.\n\nAfter careful analysis, the difference is that in the wrong SMILES, the bond between atoms :8 and :9 appears as a single bond, but examining the connectivity around the vinyl group and comparing to the image, the actual correction needed is changing the bond between atoms :7 and :8 from double to single:\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 8}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 8 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C1C2C3OCCC4C2N2CC[C@]56c7ccccc7N1C5[C@H]3[C@H]4C[C@H]26", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000131", + "op_type": "add_atom", + "image_path": "images/000131.png", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][CH:3]2[O:4][CH2:5][CH:6]=[C:7]3[CH2:8][N:9]4[CH2:10][CH2:11][C@:12]56[c:13]7[cH:14][cH:15][cH:16][cH:17][c:18]7[N:19]1[CH:20]5[C@H:21]2[C@H:22]3[CH2:23][C@H:24]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the image, I can see a carbonyl group (C=O) in the ring system. In the wrong SMILES, atom 7 is `[C:7]` which is connected to `[O:4]` via the ring. In the image, there's a C=O (ketone) group on the six-membered ring containing the oxygen ether and the nitrogen.\n\nExamining the structure more carefully: the image shows an oxygen with a double bond (C=O, shown in red) adjacent to the nitrogen in the upper ring. In the wrong SMILES, atom 5 `[CH2:5]` is between `[O:4]` and `[CH:6]`. The `[CH:6]` has a double bond to `[C:7]`. But in the correct image, the double bond from atom 6 should not be to atom 7 \u2014 instead, there should be a C=O ketone.\n\nLooking more carefully: In the image, the C=O is at the position between O (ether) and N. The wrong SMILES has `[CH:6]=[C:7]` making a C=C double bond. In the correct molecule, atom 6 should be a carbonyl carbon (C=O) with a single bond to atom 7, and the double bond should be the C=O of the ketone.\n\nSo the fix is to change the bond between atoms 6 and 7 from double to single, and change atom 6 from CH to a carbonyl C (by adding a =O group). But since we can only output one action, let me reconsider.\n\nActually, the key difference is that atom 6 in the wrong SMILES is `[CH:6]=` (part of a C=C), but in the correct image it should be a C=O (ketone). The simplest single fix: change atom 6's double bond partner. The C=C between 6 and 7 should instead be a C=O at atom 6.\n\nThe most appropriate single action is to add an =O group (making it a ketone) \u2014 but we need to also handle the double bond. Let me reconsider: changing the bond between 6 and 7 from double to single, combined with adding =O... that's two actions.\n\nThe simplest single correction: the `[CH:6]=[C:7]` should be `[C:6](=O)-[CH:7]`. Using AddGroup with \"CHO\" won't work. The best single action is:\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}\n\nWait \u2014 but that alone doesn't add the =O. Let me reconsider what's truly the one difference. The image shows no C=C double bond but has a C=O. The atom 6 needs an oxo group added.\n\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 6}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000141", + "op_type": "add_atom", + "image_path": "images/000141.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}\n\nWait, let me reconsider. The wrong SMILES is `[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1` which is toluene (methylbenzene). The image shows fluoromethylbenzene (benzyl fluoride), where the CH3 group should be a CH2F group. So I need to add an F to the CH3 group (atom 1).\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"F\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000143", + "op_type": "add_bond", + "image_path": "images/000143.png", + "wrong_smiles_mapped": "[F:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000144", + "op_type": "remove_functional_group", + "image_path": "images/000144.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:9])[cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "CH3" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000135", + "op_type": "add_bond", + "image_path": "images/000135.png", + "wrong_smiles_mapped": "[CH2:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46.[OH2:1]", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the image, I can see the correct molecule has a C=O (ketone) group where the wrong SMILES has an O-CH2 ether linkage and a water molecule.\n\nIn the wrong SMILES, atom :1 is a water molecule (OH2) and atom :5 is an oxygen in an ether bridge (O between atoms :4 and :6). In the correct image, there's a carbonyl (C=O) at that position \u2014 the oxygen should be double-bonded to a carbon, not bridging two carbons.\n\nComparing the wrong SMILES to the image: the water molecule (atom :1) needs to be removed, and the bond between O:5 and C:6 needs to be removed while the bond between O:5 and C:4 should become a double bond (making a ketone C=O). But atom :6 (CH2) connects further in the ring, so we need to maintain connectivity.\n\nLooking more carefully: In the image, the oxygen is a carbonyl oxygen (C=O) on the six-membered ring containing N. The ring goes through C:6 directly to C:4 without the oxygen bridge. So the fix is:\n\n1. The bond O:5\u2013C:6 should be removed (breaking the ether bridge)\n2. The bond C:4\u2013O:5 should become a double bond (making C=O)\n3. A bond C:4\u2013C:6 should be added (closing the ring directly)\n4. Water :1 should be removed\n\nBut I can only output a single JSON action. The key structural difference is that the bond between atoms :4 and :6 should exist directly, and O:5 should be a double bond to :4 rather than bridging. The simplest single fix that captures the main error is removing the water molecule (atom :1), but that alone doesn't fix the carbonyl.\n\nRe-examining: the wrong SMILES has `[CH:4]2[O:5][CH2:6]` where the image shows a ketone. The most impactful single change is changing the bond between :4 and :5 from single to double, which would make the carbonyl.\n\nBut actually, removing atom :1 (the water) is likely the artifact of the structural change. The core error is the bond order between C:4 and O:5.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 5}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 3 O, 3, is greater than permitted" + }, + { + "id": "000138", + "op_type": "move_substituent", + "image_path": "images/000138.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:6]2[O:5][CH2:4][C@H:22]3[CH:21]4[C@:13]5([CH2:12][CH2:11][N:10]6[CH2:9][C:8](=[CH:7]2)[C@@H:23]3[CH2:24][C@H:25]65)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]14", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES:\n\nThe image shows the correct molecule where the carbonyl (C=O) is adjacent to the nitrogen in the lactam ring, and there's a CH\u2082 group next to the oxygen in the ether bridge.\n\nIn the wrong SMILES, atom :2 (the carbonyl carbon C=O) is bonded to atom :3 (CH2) and through the ring to atom :20 (N). The oxygen ether bridge connects via atoms :4, :5, :6.\n\nComparing the structure carefully, the wrong SMILES has atom :3 as CH2 (between the carbonyl and the rest of the ring) and atom :6 as CH (connected to the ether oxygen). In the correct image, the carbonyl should be at the other position in that ring \u2014 effectively the C=O and CH2 positions need to swap.\n\nThis means atom :3 (currently CH2 next to the carbonyl) should become a CH (losing one H), and atom :6 (currently CH next to the ether oxygen) should become a CH2 (gaining one H). But more precisely, the bond between atoms :2 and :1 (C=O) needs to move \u2014 the carbonyl oxygen should be on atom :6 instead, and atom :1's oxygen should become the ether oxygen.\n\nAfter careful analysis, the key difference is that atoms :3 and :6 need to be swapped in their positions within the ring.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 6}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 6 + } + }, + "restored_smiles": "O=C1C2C=C3CN4CC[C@]56c7ccccc7N1C5[C@H](COC2)[C@H]3C[C@H]46", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000137", + "op_type": "flip_chirality", + "image_path": "images/000137.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "Looking at the wrong SMILES and comparing it to the image:\n\nThe image shows the correct molecule where the carbonyl (C=O) is connected to the nitrogen of the indole system through a CH2-CH2 linkage forming a lactam ring. \n\nAnalyzing the wrong SMILES, atom :7 is `[CH]` (with a double bond to atom :8), meaning there's a C=C double bond between atoms 7 and 8. But in the image, looking at the oxygen-containing ring with the ketone, the bond between the corresponding atoms should be a single bond \u2014 the double bond character is between atoms 6 and 7 instead (the vinyl ether portion visible in the image).\n\nWait, let me re-examine. In the wrong SMILES: `[CH2:6][CH:7]=[C:8]3` \u2014 so there's a double bond between atoms 7 and 8. In the image, I can see a C=C double bond in the seven-membered ring near the oxygen bridge. The double bond appears to be between atoms 6 and 7 instead of 7 and 8.\n\nThis means I need to move the double bond from 7-8 to 6-7.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 8}}, \"order\": \"SINGLE\"}\n\nHmm, but that's only half the fix. Let me reconsider \u2014 only one action is allowed.\n\nRe-examining more carefully: the double bond in the image is between atoms 6 and 7 (the CH=CH near the ether oxygen). The wrong SMILES has it between 7 and 8. Since atom 6 is CH2 and atom 8 is C, swapping the double bond position means changing bond 7\u20138 from double to single and 6\u20137 from single to double. But I can only output one action.\n\nLooking again at the atoms: maybe swapping substituents or a different single action applies. Actually, the simplest interpretation might be that atoms 6 and 8 need to be swapped.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 8}}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000147", + "op_type": "remove_atom", + "image_path": "images/000147.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH3:9]", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000150", + "op_type": "add_bond", + "image_path": "images/000150.png", + "wrong_smiles_mapped": "[Cl:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 6}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "ClCc1ccccn1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000146", + "op_type": "change_atom_element", + "image_path": "images/000146.png", + "wrong_smiles_mapped": "[Cl:1][O:2][c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "The wrong SMILES has `[Cl:1][O:2][c:3]1...` which represents Cl-O-pyridine. The correct molecule from the image shows a chloromethyl group (ClCH2-) attached to the pyridine ring \u2014 there's no oxygen. The oxygen atom (map_num 2) needs to be changed to a carbon.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000145", + "op_type": "add_functional_group", + "image_path": "images/000145.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}\n\nWait, let me reconsider. The wrong SMILES is `[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1` which is toluene (methylbenzene). The image shows fluoromethylbenzene (benzyl fluoride), where the CH3 group should be a CH2F group. So I need to add an F to the CH3 group (atom 1).\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"F\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000142", + "op_type": "remove_bond", + "image_path": "images/000142.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][c:8]1-2", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "The image shows benzyl fluoride (fluoromethylbenzene), which is FCH2 attached to a regular benzene ring (6-membered aromatic ring). The wrong SMILES has a fused bicyclic system with a bond between atoms 1 and 8 creating a 4-membered ring fused to a 5-membered ring instead of a normal 6-membered benzene ring.\n\nLooking at the wrong SMILES: `[F:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][c:8]1-2`\n\nThis has a bond between atom 8 and atom 1 (via ring closure \"1\") and between atoms 5 and 8 (via ring closure \"2\"), creating an abnormal fused ring. The correct molecule is a simple benzene ring, which needs 6 carbons in the ring. The ring is missing two carbon atoms to complete the benzene ring.\n\nThe key issue is the bond between atoms 8 and 3 (the \"-2\" closure connecting atom 8 back to atom 5, and the \"1\" closure connecting atom 8 to atom 3). We need to remove the direct bond between atom 8 and atom 3 to break the fused ring system.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 8}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (RemoveBond): non-ring atom 2 marked aromatic" + }, + { + "id": "000151", + "op_type": "remove_functional_group", + "image_path": "images/000151.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Br:9]", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000152", + "op_type": "add_functional_group", + "image_path": "images/000152.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "Looking at the image, I see a pyridine ring with a chloromethyl (ClCH2-) substituent. The wrong SMILES has a methyl group (CH3) attached to the pyridine at atom map 1. The correct molecule has a ClCH2- group instead, meaning the CH3 needs to be changed to a ClCH2- group.\n\nThe wrong SMILES has `[CH3:1]` attached to the ring. In the correct molecule, this carbon should have a Cl attached to it (making it a CH2Cl group).\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"Cl\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "Cl" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000156", + "op_type": "add_atom", + "image_path": "images/000156.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "Looking at the image, I see a naphthalene ring with three methyl groups: at positions 1, 2, and 8 (or equivalently, three CH3 groups on the naphthalene skeleton).\n\nThe wrong SMILES represents a naphthalene with two methyl groups (at atoms 9 and 12). The correct molecule has three methyl groups.\n\nExamining the image carefully, there's a methyl group on what corresponds to atom 3 in the wrong SMILES (which currently is just a bare CH in the ring).\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 3}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 3 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc(C)c2c(C)cccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000148", + "op_type": "add_atom", + "image_path": "images/000148.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "Looking at the image, I see a pyridine ring with a chloromethyl (ClCH2-) substituent. The wrong SMILES has a methyl group (CH3) attached to the pyridine at atom map 1. The correct molecule has a ClCH2- group instead, meaning the CH3 needs to be changed to a ClCH2- group.\n\nThe simplest fix is to add a Cl to the existing CH3 group (atom map 1), effectively converting -CH3 to -CH2Cl.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"Cl\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "Cl" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000155", + "op_type": "remove_atom", + "image_path": "images/000155.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([CH3:14])[cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "Looking at the image, I see a naphthalene ring with three methyl groups. The correct molecule is 1,2,8-trimethylnaphthalene (methyl groups at positions 1, 2, and 8 of the naphthalene).\n\nThe wrong SMILES has four methyl groups (at map numbers 1, 10, 13, 14), but the correct molecule only has three methyl groups. I need to identify which extra methyl group to remove.\n\nAnalyzing the wrong SMILES: `[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([CH3:14])[cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]`\n\nThis represents a naphthalene with methyl groups at atoms 2, 7, 9, and 12. The image shows only three methyl groups. The extra one is at atom 9 (map_num 10 is the CH3 on atom 9). Removing that methyl group gives three methyls matching the image.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 9}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 9 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(C)c(C)ccc2c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000157", + "op_type": "remove_bond", + "image_path": "images/000157.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[cH:7][c:8]-3[c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "Looking at the image, I see a naphthalene ring system with three methyl groups. The correct molecule is 1,2,8-trimethylnaphthalene \u2014 a fully aromatic naphthalene with CH3 groups.\n\nIn the wrong SMILES, there's a problematic bond between atoms 7 and 8 \u2014 it's written as `[cH:7][c:8]-3` which creates a single bond (breaking aromaticity in that ring). The naphthalene in the image is fully aromatic, so this bond should be aromatic/part of the aromatic system. The issue is the explicit single bond `-` between atoms 7 and 8, which should be removed to restore aromaticity.\n\nLooking more carefully, the `-3` notation means a single bond to ring closure 3. This makes atom 8 have a single bond to atom 6 (ring closure 3), breaking the aromaticity. That bond should be aromatic (double bond in Kekul\u00e9 form).\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 8}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 8 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Can't kekulize mol. Unkekulized atoms: 1 2 3 4 6 8 10 11" + }, + { + "id": "000154", + "op_type": "change_atom_element", + "image_path": "images/000154.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "Looking at the image, I see a naphthalene ring with three methyl groups (at positions 1, 2, and 8) and no hydroxyl group. The wrong SMILES has two methyl groups and an OH group.\n\nThe correction needed is to change the OH group at atom map 10 to a CH3 group.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 9}, \"group\": \"OH\"}\n\nWait, let me reconsider. The wrong molecule has an OH at atom 9 (via atom 10), while the correct molecule has a CH3 there instead.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"C\"}\n\nHmm, but that doesn't fully capture it. The simplest fix: replace the OH group with a CH3 group.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 9}, \"group\": \"OH\"}\n\nBut I need to also add CH3. Let me reconsider \u2014 only one action is allowed.\n\nThe difference is that atom 10 (which is O in OH) should be a CH3 group instead. Swapping OH for CH3:\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"C\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000159", + "op_type": "remove_functional_group", + "image_path": "images/000159.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]([Cl:14])[c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000160", + "op_type": "add_functional_group", + "image_path": "images/000160.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "Looking at the image, I see a naphthalene ring with three methyl groups: at positions 1, 2, and 8 (or equivalently, three CH3 groups on the naphthalene skeleton).\n\nThe wrong SMILES represents a naphthalene with two methyl groups (at atoms 9 and 12). The correct molecule has three methyl groups.\n\nExamining the image carefully, there are methyl groups on three positions of the naphthalene. The wrong molecule is missing one methyl group. Looking at the structure, atom 3 (currently a bare CH in the ring) should have a methyl group attached to match the three-methyl substituted naphthalene in the image.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 3}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 3 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc(C)c2c(C)cccc12", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000153", + "op_type": "move_substituent", + "image_path": "images/000153.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:6]1[cH:5][cH:4][cH:3][cH:8][n:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "Looking at the wrong SMILES: `[Cl:1][CH2:2][c:6]1[cH:5][cH:4][cH:3][cH:8][n:7]1`\n\nThis represents a chloromethyl group attached to a pyridine ring. The wrong SMILES has the nitrogen at position 7, between atoms 8 and 6, making it a 2-substituted pyridine (nitrogen ortho to the CH2Cl group).\n\nIn the image, the nitrogen is across the ring from the CH2Cl substituent, corresponding to a 3-(chloromethyl)pyridine. The nitrogen should be between atoms 3 and 8 (the position para/meta relative to the substituent).\n\nIn the wrong SMILES, the ring order is: 6-5-4-3-8-7(N)-6. The nitrogen is at position 7 (adjacent to atom 6 where CH2Cl is attached). In the correct molecule, the nitrogen should be at the position of atom 3 (across the ring), and atom 7 should be a carbon.\n\nSo I need to swap: change atom 7 from N to C (adding an H), and change atom 3 from C to N (removing its H).\n\nBut since only one action is allowed, let me reconsider. Looking more carefully at the image, the CH2Cl is on the carbon adjacent to N in a 3-position arrangement. The nitrogen needs to move from being directly bonded to atom 6 (the attachment point) to being one position further away.\n\nSwapping atoms 7 (N) and 8 (CH) would move nitrogen from adjacent to atom 6 to one position away, matching a 3-substituted pyridine.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 8}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 8 + } + }, + "restored_smiles": "ClCc1ccccn1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000164", + "op_type": "add_atom", + "image_path": "images/000164.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[CH:4][CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 4}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 4 + }, + "group": "CH3" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000163", + "op_type": "remove_atom", + "image_path": "images/000163.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[CH3:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 8}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 8 + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000165", + "op_type": "change_charge", + "image_path": "images/000165.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[OH+:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000162", + "op_type": "change_atom_element", + "image_path": "images/000162.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "Looking at the image, I see 2-methylpent-2-enal: a chain with an aldehyde group, a methyl branch, and a propyl chain. The correct molecule has no NH2 group \u2014 the nitrogen should be a carbon.\n\nThe wrong SMILES has an NH2 at position 1, but the image shows a simple carbon chain (CH3) at that end.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000158", + "op_type": "add_bond", + "image_path": "images/000158.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "Looking at the image, I see a naphthalene ring with three methyl groups attached. The correct molecule is 1,2,8-trimethylnaphthalene (or similar trimethylnaphthalene).\n\nThe wrong SMILES has a disconnected methane fragment [CH4:1] and only two methyl groups on the naphthalene. The image shows three methyl groups on the naphthalene, so the fix is to attach the disconnected CH4 (atom 1) as a CH3 group to the appropriate position on the naphthalene ring.\n\nLooking at the wrong SMILES structure: the naphthalene has CH3 at atom 10 (on atom 9) and CH3 at atom 13 (on atom 12). The image shows a third methyl group on an adjacent aromatic carbon. Atom 2 is adjacent to atom 12 and currently has a hydrogen \u2014 this is where the third methyl should go.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 1}}\n\nWait, I need to reconsider \u2014 I can only output a single action. Let me use AddGroup to add the methyl to the ring, but the disconnected CH4 needs to be removed too.\n\nThe simplest single action: Move the disconnected methane (atom 1) to become a substituent on atom 2 of the naphthalene ring.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 1}, \"from_atom\": {\"map_num\": 1}, \"to_atom\": {\"map_num\": 2}}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000168", + "op_type": "add_bond", + "image_path": "images/000168.png", + "wrong_smiles_mapped": "[CH2:3]=[C:4]([CH3:5])[CH:6]=[O:7].[CH3:1][CH3:2]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000149", + "op_type": "remove_bond", + "image_path": "images/000149.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]1-2", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "Looking at the image, I see a pyridine ring with a chloromethyl (ClCH2) substituent. This is 3-(chloromethyl)pyridine \u2014 a six-membered aromatic ring with one nitrogen.\n\nThe wrong SMILES `[Cl:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]1-2` contains a fused bicyclic system (indicated by the ring closure numbers 1 and 2 creating a bridge between atoms 5-8), which is not what the image shows. The image shows a simple pyridine ring.\n\nThe issue is the bond between atoms 5 and 8 that creates the fused ring system. Removing that bond will give a proper pyridine ring with the chloromethyl group.\n\n```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 8}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000169", + "op_type": "remove_functional_group", + "image_path": "images/000169.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[Br:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 8}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 8 + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000161", + "op_type": "move_substituent", + "image_path": "images/000161.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[C:12]([CH3:13])[c:11]2[cH:5][cH:6][cH:7][c:8]([c:9]2[CH3:10])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "Looking at the image, I see a naphthalene core with three methyl groups: at positions 1, 2, and 8 (peri positions and adjacent). The correct molecule has three methyl groups on the naphthalene ring.\n\nAnalyzing the wrong SMILES: `[CH3:1][C:2]1=[C:12]([CH3:13])[c:11]2[cH:5][cH:6][cH:7][c:8]([c:9]2[CH3:10])[CH:4]=[CH:3]1`\n\nThis has methyl groups at atoms 2 (via CH3:1), 12 (via CH3:13), and 9 (via CH3:10). The ring system has atom 8 bearing a substituent CH3:10 through atom 9.\n\nComparing with the image: the correct molecule has methyl groups at three positions on the naphthalene, but the wrong SMILES has atom 9 as a carbon bearing a methyl group (CH3:10), making it part of the ring junction area. In the image, the position corresponding to atom 9 should not have a methyl group \u2014 instead it's an unsubstituted aromatic carbon at the ring junction. The methyl at atom 8 is what's shown in the image.\n\nThe issue is that the methyl group (CH3:10) is on atom 9 (ring junction) instead of atom 8. It needs to be moved from atom 9 to atom 8.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 10}, \"from_atom\": {\"map_num\": 9}, \"to_atom\": {\"map_num\": 8}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 9 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 8 C, 5, is greater than permitted" + }, + { + "id": "000167", + "op_type": "remove_bond", + "image_path": "images/000167.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]1[CH:3]=[C:4]([CH3:5])[C:6]1=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "Looking at the wrong SMILES, it represents a cyclopentenone derivative (a 5-membered ring with a ketone). The image shows an open-chain aldehyde: 2-methylpent-2-enal (a linear molecule with an aldehyde group, a methyl branch, and a double bond).\n\nThe key difference is that the wrong molecule has a ring (bond between atoms 2 and 6 closing the cycle), while the correct molecule is open-chain. Removing the ring-closing bond between atoms 2 and 6 will open the ring and give the correct linear structure.\n\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 6}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000166", + "op_type": "change_bond_order", + "image_path": "images/000166.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "Looking at the image, I can see a molecule with an aldehyde group and a methyl branch, where there's a C=C double bond in the chain (not a C=O single bond with C-C single bond arrangement).\n\nThe correct molecule is 2-methylpent-2-enal: the double bond should be between C4 and C6 (currently C=O aldehyde carbon), and the bond between C4 and C6 should be a double bond, while C6-O7 remains as the aldehyde.\n\nComparing:\n- Wrong SMILES: `CH3-CH2-CH2-CH(CH3)-CH=O` \u2014 the double bond is between C6 and O7, and C4-C6 is single. C4 has an H.\n- Image shows: `CH3-CH2-CH=C(CH3)-CH=O` \u2014 there's a C=C double bond between C3 and C4, making it an \u03b1,\u03b2-unsaturated aldehyde.\n\nSo the fix is to change the bond between C3 and C4 from single to double. This converts the saturated aldehyde to the unsaturated one shown in the image.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000174", + "op_type": "change_charge", + "image_path": "images/000174.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[OH+:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 9 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000170", + "op_type": "add_functional_group", + "image_path": "images/000170.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]=[C:3]([CH3:4])[CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "Looking at the wrong SMILES: `[CH3:1][CH:2]=[C:3]([CH3:4])[CH:5]=[O:6]`\n\nThis represents: CH3-CH=C(CH3)-CHO (2-methylbut-2-enal)\n\nThe correct molecule in the image shows a longer carbon chain: it has an ethyl group (not methyl) on the left side, with a methyl branch and an aldehyde. This corresponds to 2-methylpent-2-enal: CH3CH2CH=C(CH3)CHO.\n\nThe difference is that atom 1 (CH3) attached to atom 2 should be an ethyl group (CH2CH3) instead of just CH3. I need to add a CH3 group to atom 1.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000172", + "op_type": "remove_atom", + "image_path": "images/000172.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[NH2:13])[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the wrong SMILES, I can identify the structure as a methylated isatin derivative with an NH2 group. The correct molecule in the image is 5-methylisatin, which has no NH2 group on the ring.\n\nThe wrong SMILES has an NH2 group attached at atom :7. The correct molecule doesn't have this NH2 group.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "NH2" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000177", + "op_type": "remove_functional_group", + "image_path": "images/000177.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[c:3]([Cl:13])[cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000171", + "op_type": "change_atom_element", + "image_path": "images/000171.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the wrong SMILES, it represents an isatin with an NH2 group at one position. The correct molecule in the image shows an isatin (indoline-2,3-dione) with a methyl (CH3) group on the benzene ring instead of an NH2 group.\n\nThe wrong SMILES has an NH2 group at atom map :1, but the image shows a CH3 group at that position on the aromatic ring.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}\n\nWait, let me reconsider. The NH2 at atom :1 is attached to the aromatic ring. In the image, there's a methyl group on the ring. The simplest fix is to replace the NH2 group with a CH3 group.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"NH2\"}\n\nLet me re-examine more carefully. The wrong SMILES has NH2 on atom :2 (via atom :1). The correct image has CH3 on the ring. The most direct action:\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000173", + "op_type": "add_atom", + "image_path": "images/000173.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the image, I see 5-methylisatin \u2014 an isatin with a methyl group on the benzene ring at the 5-position.\n\nThe wrong SMILES represents unsubstituted isatin. The correct molecule has a methyl group (CH3) added to the benzene ring.\n\nLooking at the numbering, the methyl group should be on atom :1 (the position corresponding to the 5-position of the indole ring, which in the image has the CH3 substituent).\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(c1)NC(=O)C2=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000178", + "op_type": "add_functional_group", + "image_path": "images/000178.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the image, I see 5-methylisatin \u2014 an isatin with a methyl group at the 5-position of the benzene ring.\n\nThe wrong SMILES represents unsubstituted isatin. The correct molecule has a methyl group (CH3) on the benzene ring. Based on the image, the methyl group is at the 5-position, which corresponds to atom map number 2 in the SMILES.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(c1)NC(=O)C2=O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000176", + "op_type": "add_bond", + "image_path": "images/000176.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][NH:12]2.[OH2:11]", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the wrong SMILES, I can identify the structure as a methylindole derivative. The wrong SMILES has a `[CH2:10]` between the carbonyl and NH in the five-membered ring, plus a water molecule `[OH2:11]`.\n\nThe correct molecule in the image is 5-methylisatin, which has two carbonyl groups (C=O) on the five-membered ring \u2014 one at position 8 (already present) and one at position 10 (which is currently CH2 and needs to become C=O).\n\nThe atom map 10 is currently `[CH2:10]`, but it should be a carbonyl carbon `C(=O)`. The water molecule (atom 11) provides the oxygen that should be the second C=O.\n\nI need to change the bond between atom 10 and the oxygen (atom 11) \u2014 but first, atom 11 is a disconnected water. The simplest fix: add a group to atom 10.\n\nLooking more carefully: atom 10 is `[CH2:10]` and atom 11 is `[OH2:11]` (water, disconnected). The correct molecule needs atom 10 to have a `=O`. So I need to add a bond between atom 10 and atom 11, making it a double bond (and adjusting hydrogens implicitly).\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 10}, \"atom2\": {\"map_num\": 11}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000175", + "op_type": "change_bond_order", + "image_path": "images/000175.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH:10]([OH:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the image, I see 5-methylindoline-2,3-dione (5-methylisatin), which has:\n- A methylated benzene ring fused with a five-membered ring\n- NH in the five-membered ring\n- Two C=O groups (at positions 2 and 3 of the five-membered ring)\n\nThe wrong SMILES has atom 10 as CH with an OH group, but in the correct molecule, atom 10 should be a carbonyl carbon (C=O), meaning the OH group needs to be removed and atom 10 changed to have a double bond to oxygen instead.\n\nLooking more carefully:\n- Wrong SMILES: `[CH:10]([OH:11])` \u2014 atom 10 has an OH and a single bond to O:9 (C=O at atom 8)\n- Correct molecule: atom 10 should be C=O (a second ketone), no OH\n\nThe fix is to remove the OH group from atom 10 and change the bond between atom 10 and its oxygen (atom 11) to be a C=O instead. But atom 11 is the OH. Let me re-examine.\n\nIn the wrong SMILES: `[C:8](=[O:9])[CH:10]([OH:11])[NH:12]2`\n- Atom 8: C=O (correct, one ketone)\n- Atom 10: CH-OH (wrong, should be C=O)\n\nSo atom 10 has an OH (atom 11) attached via single bond, but it should be =O. I need to:\n1. Change atom 10 from CH to C\n2. Change atom 11 from OH to O\n3. Change bond between 10 and 11 from SINGLE to DOUBLE\n\nThe simplest single action: Change the bond between atom 10 and atom 11 from single to double, which effectively converts C-OH to C=O.\n\nBut that leaves extra H. Let me use `ChangeAtom` on atom 11 to remove the H and change the bond.\n\nThe most direct single fix is changing the bond order:\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 10}, \"atom2\": {\"map_num\": 11}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000181", + "op_type": "change_atom_element", + "image_path": "images/000181.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][SH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES, I need to identify the difference between it and the image.\n\nThe wrong SMILES contains an S atom at position :6 (`[SH:6]`), but in the image, the correct molecule shows a nitrogen (N) at that position \u2014 it's a fused bicyclic system with an oxazoline ring fused to a cyclopentane, where the atom connecting the two rings is N, not S.\n\nThe image shows an N atom (no H attached) at that position in the ring junction.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CN(C)C1=NN2C(O)C(O)C(CO)C2O1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000179", + "op_type": "move_substituent", + "image_path": "images/000179.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:7][N:12]2[C:5](=[CH:6][C:8](=[O:9])[C:10]2=[O:11])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the image, I see 5-methylisatin: a methylated indole derivative with an NH group and two carbonyl oxygens (isatin core).\n\nIn the wrong SMILES, atom :12 is nitrogen, and looking at the structure, the nitrogen should be bonded to a hydrogen (NH), not be part of a six-membered ring arrangement. The key issue is that atom :5 is currently a carbon with a double bond to :6, making a 6-membered ring with the nitrogen. In the correct molecule (isatin), the five-membered ring should have the nitrogen bonded to a CH2-like carbon (C:5), not through a C=C bond.\n\nComparing more carefully: the wrong SMILES has a C=C double bond between atoms :5 and :6, but in isatin the bond between the carbon adjacent to NH and the carbon bearing the C=O should be a single bond (C:5 is sp3 in the five-membered ring of isatin).\n\nThe wrong molecule has `[C:5](=[CH:6]...)` \u2014 a double bond between :5 and :6. In the correct isatin structure, this should be a single bond (the C at position 3 of isatin is sp3, bonded to two C=O groups and the ring).\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 6}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC1=CN2C(=O)C(=O)CC2C=C1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000185", + "op_type": "remove_bond", + "image_path": "images/000185.png", + "wrong_smiles_mapped": "[CH3:1][N:2]1[CH2:3][C:9]2([OH:10])[CH:7]([OH:8])[CH:6]3[N:5]=[C:4]1[O:15][CH:14]3[CH:11]2[CH2:12][OH:13]", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES, I need to trace the structure and compare it to the image.\n\nIn the wrong SMILES: `[CH3:1][N:2]1[CH2:3][C:9]2([OH:10])[CH:7]([OH:8])[CH:6]3[N:5]=[C:4]1[O:15][CH:14]3[CH:11]2[CH2:12][OH:13]`\n\nThe N-methyl group (atom :2) is connected to the ring at position :3 and :4. In the image, the NMe group is on the oxazoline carbon (C=N side), connected via N with two methyl groups (dimethylamine).\n\nLooking at the image carefully, the nitrogen on the right side has TWO methyl groups (it's an NMe2 group). In the wrong SMILES, atom :2 (N) only has one CH3 group attached.\n\nSo the fix is to add another CH3 group to atom :2.\n\n```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "AddGroup failed: group='CH3' anchor=1" + }, + { + "id": "000187", + "op_type": "add_functional_group", + "image_path": "images/000187.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH2:7][CH:8]([OH:9])[CH:10]([CH2:11][OH:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES and the correct molecule image:\n\nThe wrong SMILES has the OH group on atom 9 (attached to atom 8) and the CH2OH group on atoms 11-12 (attached to atom 10). The image shows:\n- OH on the top of the cyclopentane ring\n- HO on the left side\n- HOCH2 at the bottom\n\nTracing through the structure, in the wrong SMILES atom 8 has OH and atom 10 has CH2OH. But looking at the image carefully, the hydroxyl groups and the CH2OH need to be in specific positions.\n\nComparing the wrong SMILES connectivity with the image, the issue is that the OH on atom 9 (attached to atom 8) and the CH2OH group on atom 10 need to be swapped \u2014 in the image, the CH2OH is on the atom corresponding to atom 8, and the OH is on the atom corresponding to atom 10.\n\nThis means atoms 8 and 10 have their substituents swapped.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 10}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 10 + } + }, + "restored_smiles": "CN(C)C1=NC2CC(CO)C(O)C2O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000182", + "op_type": "add_atom", + "image_path": "images/000182.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH3:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the image, I can see the correct molecule has a CH2OH (hydroxymethyl) group where the wrong SMILES has just a CH3 group at atom map number 12.\n\nIn the wrong SMILES, atom :11 has a CH3 group (atom :12), but in the image, that position has a CH2OH group instead.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 12}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 12 + }, + "group": "OH" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000180", + "op_type": "swap_substituents", + "image_path": "images/000180.png", + "wrong_smiles_mapped": "[CH3:1][c:5]1[cH:4][cH:3][c:2]2[cH:7][c:6]1[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "Looking at the wrong SMILES, I need to parse the structure and compare it to the image.\n\nThe wrong SMILES: `[CH3:1][c:5]1[cH:4][cH:3][c:2]2[cH:7][c:6]1[C:8](=[O:9])[C:10](=[O:11])[NH:12]2`\n\nThis represents a methylated isatin where the NH is at position 2 (connected to atom :2) and the carbonyl C(=O) at atom :8 is connected to atom :6, with another C(=O) at atom :10 between atoms :8 and :12.\n\nIn the wrong SMILES, the NH (:12) connects to atom :2 and atom :10. The ring closure `2` links atom :2 and atom :12, meaning NH is bonded to the carbon at position :2 on the benzene ring.\n\nIn the image, the correct molecule shows 5-methylisatin where NH is at the top of the five-membered ring, connecting to the benzene ring at the position adjacent to where it currently connects. Specifically, the NH should be connected to atom :7 (the other bridgehead carbon), not atom :2.\n\nLooking more carefully: In the wrong SMILES, the bond path around the five-membered ring is: :2 \u2014 :12(NH) \u2014 :10(C=O) \u2014 :8(C=O) \u2014 :6, with :2 and :6 being the fusion carbons. In the image, the NH connects to the top of the ring and the C=O is at the bottom near the benzene ring. This means the NH and the adjacent C=O should swap positions relative to the fusion carbons.\n\nThe issue is that in the wrong molecule, NH(:12) is bonded to atom :2, but in the correct molecule it should be bonded to atom :7. This is effectively moving the NH substituent from atom :2 to atom :7.\n\nThis corresponds to swapping atoms :12 (NH) and :8 (C=O) positions, or equivalently swapping the connectivity. Looking at the five-membered ring: the wrong order is :6-:8(=O)-:10(=O)-:12(NH)-:2, but it should be :7-:12(NH)-:10(=O)-:8(=O)-:6.\n\nThe simplest fix: move the bond of NH from atom :2 to atom :7.\n\n```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 12}, \"from_atom\": {\"map_num\": 2}, \"to_atom\": {\"map_num\": 7}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 12 + }, + "from_atom": { + "map_num": 2 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "Cc1cccc2c1C(=O)C(=O)N2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000192", + "op_type": "add_functional_group", + "image_path": "images/000192.png", + "wrong_smiles_mapped": "[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]1[OH:12]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "Looking at the wrong SMILES, I see: an aldehyde (CHO) at position 2, a carboxylic acid (COOH) at positions 8-9-10, and an OH at position 12 on the ring.\n\nThe correct molecule in the image shows: two carboxylic acid groups (COOH) on adjacent ring carbons, with an OH group on the ring carbon between them. So the aldehyde (CHO at atom 2) needs to become a carboxylic acid (COOH).\n\nThe wrong SMILES has `[O:1]=[CH:2]` (an aldehyde) where the image shows a full COOH group. I need to add an OH group to atom 2 to convert the aldehyde to a carboxylic acid.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "OH" + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000186", + "op_type": "add_bond", + "image_path": "images/000186.png", + "wrong_smiles_mapped": "[CH3:12][OH:13].[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES, I see it contains a disconnected methanol fragment `[CH3:12][OH:13]` and the main molecule has `[CH2:11]` connecting atoms 14 and 9.\n\nIn the correct image, the molecule has a `CH2OH` group (hydroxymethyl) hanging off the cyclopentane ring, meaning atom 11 should connect to an OH group, and the methanol fragment should be incorporated.\n\nThe wrong SMILES has a separate `[CH3:12][OH:13]` fragment and atom 11 is `[CH2:11]` with no OH. The correct structure shows atom 14 bearing a `CH2OH` substituent. Looking more carefully, atom 11 is bonded to atoms 9 and 14 in the ring. In the image, the carbon corresponding to atom 14 has a CH2OH pendant group.\n\nThe fix is to move the OH group (atom 13) from being attached to atom 12 (the disconnected methanol) and instead attach it to atom 12 which should connect to atom 11. But actually, the simplest correction: the disconnected `[CH3:12][OH:13]` should be connected to the main ring. Atom 11 in the wrong SMILES is `CH2` bridging atoms 9 and 14. In the image, the CH2OH hangs off atom 14.\n\nComparing: the wrong molecule has atom 11 as CH2 in the ring between atoms 9 and 14, plus a disconnected CH3OH. The correct molecule should have atom 12 bonded to atom 14 (making the CH2OH group on atom 14). So I need to add a bond between atom 14 and atom 12.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 14}, \"atom2\": {\"map_num\": 12}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 14 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)CC2(CO)O1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000191", + "op_type": "change_bond_order", + "image_path": "images/000191.png", + "wrong_smiles_mapped": "[OH:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "Looking at the image, I see a molecule with:\n- A benzene ring\n- Two carboxylic acid groups (COOH) at positions 1 and 3\n- One OH group at position 2 (between the two COOH groups)\n\nThe correct molecule is 2-hydroxyisophthalic acid.\n\nNow analyzing the wrong SMILES: `[OH:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]`\n\nThis has:\n- Atom :2 is a CH with two OH groups (:1 and :3) \u2014 this is a CH(OH)2 group, not a COOH group\n- Atom :8 has a proper COOH group (:9, :10, :11)\n- Atom :12 has an OH (:13)\n\nIn the correct molecule, atom :2 should be a carbon of a COOH group (C=O with OH), not CH(OH)(OH). Specifically, atom :2 should be a carbonyl carbon (C with a double bond to one oxygen), and the bond to atom :2 from :1 (OH) should be single, while :3 (OH) should become =O.\n\nThe key difference: atom :3 (OH) should be =O instead of OH. The bond between :2 and :3 should be a double bond, and :2 should lose its hydrogen (become a sp2 carbon).\n\nThe simplest fix is changing atom :3 from OH to O and making the bond a double bond. But since :2 is `[CH]`, it also needs to lose its H. Let me use a single action.\n\nThe core issue is that the bond between atom :2 and atom :3 should be a double bond (making :3 a ketone oxygen and :2 a proper carboxylic acid carbon).\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000190", + "op_type": "change_charge", + "image_path": "images/000190.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "Looking at the image, the correct molecule is 2-hydroxyisophthalic acid \u2014 a benzene ring with an OH group and two COOH groups. The left carboxylic acid group should be a normal C(=O)(OH) group.\n\nIn the wrong SMILES, atom :1 is `[OH+]=` (a positively charged OH double-bonded to carbon :2), whereas in the correct molecule this should be a neutral `O` double-bonded to carbon :2 (the carbonyl oxygen of the left COOH group).\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000188", + "op_type": "move_substituent", + "image_path": "images/000188.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][C:14]2([CH2:12][OH:13])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES and the correct molecule image:\n\nThe wrong SMILES has atom :11 as CH2 and atom :14 as a quaternary carbon C (connected to CH2OH and O). Looking at the image, the carbon bearing the CH2OH group should be a CH, not a quaternary carbon bonded to both the ring CH2 and O. \n\nExamining more carefully: In the wrong SMILES, the connectivity around atoms :11 and :14 shows `[CH2:11][C:14]2([CH2:12][OH:13])[O:15]1`, meaning atom :14 is connected to atoms :11, :12, :7 (ring closure 2), and :15 (ring closure 1).\n\nIn the image, the carbon bearing the CH2OH substituent also has an H (it's a CH). The ring junction atom :14 should have an H. But looking at the bond between atoms :11 and :14 \u2014 in the image, there's no extra CH2 group there. The hydroxymethyl group hangs off what corresponds to atom :11 area.\n\nRe-examining: The wrong SMILES has `[CH2:11][C:14]2([CH2:12][OH:13])[O:15]1` \u2014 atom :14 is the ring junction with 4 bonds (to :11, :7, :12, :15). In the image, the ring junction carbon that connects to O has an H, making it CH, and the CH2OH hangs off the adjacent carbon.\n\nThe issue is that the CH2OH group should be on atom :11 instead of atom :14. This is a MoveSubstituent action \u2014 moving the CH2OH from atom :14 to atom :11.\n\nWait, but atom :11 is CH2 \u2014 if we move CH2OH there, we need it to become CH. Let me reconsider.\n\nActually, the simplest fix: swap the substituent (the CH2OH group, anchored at atom :12) from atom :14 to atom :11.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 12}, \"from_atom\": {\"map_num\": 14}, \"to_atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 12 + }, + "from_atom": { + "map_num": 14 + }, + "to_atom": { + "map_num": 9 + } + }, + "restored_smiles": "CN(C)C1=NC2C(CC(O)(CO)C2O)O1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000183", + "op_type": "change_charge", + "image_path": "images/000183.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[NH+:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES, the nitrogen at position 5 (the ring nitrogen) has a positive charge `[NH+:5]`, meaning it's protonated with an H attached.\n\nIn the correct molecule image, the ring nitrogen is shown as a neutral `N` with a double bond (imine-like, `=N-`), with no hydrogen and no charge.\n\nThe fix is to change atom 5 from `[NH+]` to neutral `N` (charge 0).\n\n```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000189", + "op_type": "swap_substituents", + "image_path": "images/000189.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[CH:14]1[CH:6]2[N:5]=[C:4]([CH:11]([CH2:12][OH:13])[CH:9]([OH:10])[CH:7]2[OH:8])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES, I need to trace the structure and compare it with the image.\n\nIn the wrong SMILES, the N(CH3)2 group is attached to atom :4 (the C in the oxazoline ring), and the CH(CH2OH)(CH(OH)(CH(OH))) substituent is on atom :14.\n\nIn the image, the correct molecule shows:\n- An oxazoline ring (O-C=N fused with a cyclopentane)\n- The N(CH3)2 group is on the C=N carbon of the oxazoline\n- The CH2OH group is a substituent coming off the ring junction atom connected to O\n\nLooking more carefully at the connectivity: In the wrong SMILES, the hydroxymethyl group (CH2OH, atoms :12, :13) is attached to atom :11, which is attached to atom :4 (the C=N carbon). But in the image, the hydroxymethyl group is on the atom adjacent to the O in the ring (the ring junction carbon).\n\nComparing the wrong SMILES with the image, the key difference is that the NMe2 group is connected to atom :4 (C=N carbon) in the image, and the CH(CH2OH) branch is on atom :14 (the carbon bonded to O). In the wrong SMILES, atom :11 with its substituents is bonded to atom :4, while NMe2 is on atom :2 bonded... \n\nLet me re-examine. The wrong SMILES has NMe2 on atom :2 which connects to atom :14. Atom :4 has atom :11 attached. In the image, NMe2 is on the C=N carbon (atom :4), and the CH(CH2OH) should be on atom :14.\n\nSo the substituents on atoms :4 and :14 need to be swapped: NMe2 should move to atom :4, and the CH(CH2OH)(CH(OH)...) group should be on atom :14.\n\nActually, looking again: atom :11 is currently bonded to atom :4. It should be bonded to atom :14 instead.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 4}, \"to_atom\": {\"map_num\": 14}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 4 + }, + "to_atom": { + "map_num": 14 + } + }, + "restored_smiles": "CN(C)C12OC=NC1C(O)C(O)C2CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000196", + "op_type": "change_charge", + "image_path": "images/000196.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[OH+:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000195", + "op_type": "add_functional_group", + "image_path": "images/000195.png", + "wrong_smiles_mapped": "[cH:1]1[n:2][c:3]([Cl:4])[n:5][c:6]([C:7]([Cl:8])([Cl:9])[Cl:10])[n:11]1", + "correct_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "predicted_raw": "Looking at the image, I see a triazine ring with three substituents:\n- One position has a single Cl attached to a CH (like CHCl)\n- One position has a CCl3 group\n- One position has a single Cl\n\nThe wrong SMILES has: position 3 has Cl, position 6 has CCl3, and position 1 is just CH.\n\nThe image shows that the CH at position 1 should also have a Cl attached. Looking more carefully, the image shows Cl on the top-left carbon and Cl on the bottom-left carbon, plus CCl3 on the right carbon.\n\nThe wrong SMILES has atom 1 as `[cH:1]` with no substituent, atom 3 with one Cl, and atom 6 with CCl3. The image shows Cl on both ring carbons (not just one) plus CCl3 on the third.\n\nSo atom 1 (which is bare `cH`) needs a Cl group added.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"Cl\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "Cl" + }, + "restored_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000198", + "op_type": "add_functional_group", + "image_path": "images/000198.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "NCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000193", + "op_type": "move_substituent", + "image_path": "images/000193.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[c:5]([C:9](=[O:10])[OH:11])[cH:6][cH:7][cH:8][c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "Looking at the wrong SMILES, I see the structure has:\n- A COOH group at position 1 (atoms 1,2,3)\n- A COOH group at position 2 (atoms 9,10,11)\n- An OH group at position 6 (atom 13)\n\nThe wrong SMILES places the OH on atom 12, which is adjacent to atom 5 (bearing the second COOH). In the image, the OH is between the two COOH groups \u2014 attached to the carbon between them.\n\nIn the wrong SMILES: the ring is c4-c5-c6-c7-c8-c12, with COOH on c4, COOH on c5, and OH on c12. So OH is on the carbon adjacent to c4 (opposite side from c5).\n\nIn the correct image: OH is on the carbon between the two COOH-bearing carbons (i.e., adjacent to both). So the OH needs to move from atom 12 to atom 5, and the second COOH needs to move from atom 5 to atom 12.\n\nThis is a swap of substituents between atoms 5 and 12.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 12}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 12 + } + }, + "restored_smiles": "O=C(O)c1cccc(O)c1C(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000197", + "op_type": "change_bond_order", + "image_path": "images/000197.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]=[CH:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "Looking at the image, the correct molecule has an ethylamine chain (NH2-CH2-CH2-) connected to the sulfonamide nitrogen, not a vinyl amine (NH2-CH=CH-) as in the wrong SMILES.\n\nThe difference is that the bond between atoms 2 and 3 should be a single bond, not a double bond.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000184", + "op_type": "change_bond_order", + "image_path": "images/000184.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][C:6]2=[C:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "Looking at the wrong SMILES and the correct molecule image:\n\nThe wrong SMILES has an OH group on atom 8 (C7), but in the image, the correct molecule doesn't have an OH on that carbon of the fused ring junction. The carbon at position 7 (C7) in the wrong SMILES bears an OH group, but in the image, that carbon (the ring junction between the oxazoline and cyclopentane) has no OH \u2014 it just has hydrogens.\n\nLet me trace through more carefully:\n\nWrong SMILES: `[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][C:6]2=[C:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1`\n\nThe issue is atom 6 and 7: `[C:6]2=[C:7]` \u2014 there's a double bond between C6 and C7. But in the image, the fused bicyclic system has a single bond between those ring-junction carbons (they are sp3 in the cyclopentane ring). The double bond `C6=C7` doesn't match the image.\n\nActually, looking more carefully: the oxazoline ring has C4=N5 double bond and C4-O15 (closing the ring). C6 should be connected to N5 and be part of the cyclopentane. In the image, C6-C7 is a single bond in the cyclopentane ring, and C6 has a hydrogen (it's a CH).\n\nThe wrong SMILES has `[C:6]2=[C:7]` (double bond), but the image shows a single bond there. Also, `[C:6]` without H becomes `[CH:6]` with a single bond.\n\nBut the key single correction: the bond between atoms 6 and 7 should be SINGLE, not DOUBLE.\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000194", + "op_type": "swap_substituents", + "image_path": "images/000194.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:13])[c:12]1[C:9](=[O:10])[OH:11]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "Looking at the wrong SMILES, I see the molecule has two COOH groups and an OH on the benzene ring. The wrong SMILES has the OH at position 8 (between the two COOH-bearing carbons at positions 4 and 8, via atom 12).\n\nIn the correct image, the OH is on atom 12 (the carbon between the two COOH-bearing ring carbons), and the structure shows the OH is between the two carboxylic acid groups at the bottom of the ring.\n\nComparing the wrong SMILES to the image: the wrong SMILES has OH on atom 8, but in the correct molecule, the OH should be on atom 12 (which is the carbon between atoms 4 and 8). Wait \u2014 atom 12 is a ring carbon. Let me re-parse:\n\nRing: c4-c5-c6-c7-c8-c12-c4, with OH on atom 8 and COOH on atoms 4 and 12 (via atom 9).\n\nIn the image, the OH is on the ring carbon between the two COOH-bearing carbons \u2014 that's atom 12. But atom 12 already bears the second COOH group. Actually, looking more carefully: in the wrong SMILES, atom 8 has OH (atom 13) and atom 12 has COOH. In the correct image, the OH is on atom 12 (between atoms 4 and 8), and atom 8 has the COOH.\n\nThis means the OH (atom 13) and COOH (atom 9's group) need to swap \u2014 OH should move from atom 8 to atom 12, and COOH should move from atom 12 to atom 8.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 12}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 12 + } + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000201", + "op_type": "change_bond_order", + "image_path": "images/000201.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][CH:41]([CH3:42])[OH:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to identify the structural difference.\n\nIn the wrong SMILES, atom 43 is an OH group attached to atom 41. In the image, I can see that the corresponding position has no free OH group \u2014 instead, looking carefully at the structure, atom 41 (the CH with CH3 group) doesn't have a hydroxyl group. The correct molecule shows that this OH is not present.\n\nExamining more carefully, the image shows the oxygen-containing ring system where the position corresponding to atom 43 (OH) should not be there. The correct structure lacks this hydroxyl group at that position.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 41}, \"group\": \"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 41 + }, + "group": "OH" + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OCC", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000204", + "op_type": "change_charge", + "image_path": "images/000204.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][C:4](=[OH+:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "Looking at the image, I see a five-membered ring with:\n- Two C=O groups (neutral oxygen atoms, no charges)\n- An NH group\n- Two bromine substituents on the carbons between the C=O groups\n- A C=C double bond between the two brominated carbons\n\nIn the wrong SMILES, atom :5 (the oxygen on C4) is `[OH+]` \u2014 a positively charged, protonated oxygen. In the correct molecule, this should be a neutral `O` (a carbonyl oxygen, C=O with no charge).\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000200", + "op_type": "change_charge", + "image_path": "images/000200.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[OH+:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "Looking at the image carefully, I can see the correct molecule has a neutral ester group (C(=O)O) at the position where the wrong SMILES has a protonated oxocarbenium ([OH+:43]). The atom mapped as :43 is shown as `[OH+]` but in the correct structure it should be a neutral oxygen (part of an ester/lactone C-O bond, not protonated).\n\nExamining the SMILES end: `[O:40][C:41]([CH3:42])=[OH+:43]` \u2014 this represents a protonated carboxylic acid/ester. In the image, this group is a normal acetate ester `OC(CH3)=O`, so atom 43 should be a neutral O with no charge.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 43}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 43 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000206", + "op_type": "move_substituent", + "image_path": "images/000206.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[N:3]([Br:9])[C:4](=[O:5])[C:6]([Br:7])=[CH:8]1", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "Looking at the wrong SMILES: `[O:1]=[C:2]1[N:3]([Br:9])[C:4](=[O:5])[C:6]([Br:7])=[CH:8]1`\n\nThe wrong molecule has:\n- N:3 has a Br:9 attached to it\n- C:6 has one Br:7\n- C:8 has no Br\n\nThe correct molecule (from the image) shows:\n- NH (no Br on nitrogen)\n- Two Br atoms on adjacent carbons (C:6 and C:8)\n- The double bond is between C:6 and C:8\n\nSo the Br:9 needs to move from N:3 to C:8.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 3}, \"to_atom\": {\"map_num\": 8}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 3 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000205", + "op_type": "change_bond_order", + "image_path": "images/000205.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][CH:4]([OH:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "Looking at the wrong SMILES: `[O:1]=[C:2]1[NH:3][CH:4]([OH:5])[C:6]([Br:7])=[C:8]1[Br:9]`\n\nThis gives: O=C1-NH-CH(OH)-C(Br)=C1(Br)\n\nThe correct molecule from the image shows a pyrrole ring with:\n- Two C=O groups (at positions 2 and 5)\n- Two Br atoms on the double-bond carbons (positions 3 and 4)\n- NH in the ring\n\nSo the correct structure is: O=C1-NH-C(=O)-C(Br)=C1(Br)\n\nComparing: atom 4 in the wrong SMILES is CH(OH) but should be C(=O). The OH group at atom 5 needs to be changed to a ketone oxygen (=O).\n\nThe fix is to remove the OH group on atom 4 and replace it with a C=O, but more precisely, atom 5 (OH) should become a double-bonded O (like atom 1). This means changing the bond between atom 4 and atom 5 from single to double, and changing atom 5 from OH to O.\n\nActually, the simplest correction: atom 4 has an OH group (atom 5) attached via single bond. In the correct molecule, this should be =O. So I need to change the bond order between atom 4 and atom 5 from SINGLE to DOUBLE, and the OH needs to lose its H (becoming just O).\n\nThis can be captured as removing the OH group and adding a =O, but looking at the available actions, the most direct fix is:\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 5}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000207", + "op_type": "change_charge", + "image_path": "images/000207.png", + "wrong_smiles_mapped": "[CH3:1][OH+:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "Looking at the image, I see a methyl ester group (C(=O)OCH3) at the relevant position. In the wrong SMILES, atom :2 is `[OH+]` (a positively charged oxygen), but it should be a neutral oxygen connecting the carbonyl to the methyl group, i.e., a normal ester oxygen.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000203", + "op_type": "swap_substituents", + "image_path": "images/000203.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:23]1([CH3:8])[CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[CH2:11][CH:9]([CH3:10])[C:7]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]21)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[O:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to identify the structural difference.\n\nThe wrong SMILES has a terminal `[CH2:1]=[CH:2]` (vinyl group, CH2=CH-), but the image shows a terminal `CH2=C(CH3)-` pattern, indicating there's a methyl branch on the alkene. Specifically, the image shows an isobutenyl/isopropenyl group: `CH2=C(CH3)-CH=CH-`.\n\nLooking more carefully, the image shows the side chain as `CH2=C(CH3)-CH=CH-CH2-` which means atom 3 (which currently has a CH3 substituent) is correct, but atom 1 should be `CH2=` and atom 2 connects to atom 3 which bears a methyl. Actually, re-examining: the current SMILES has `[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6]` which is `CH2=CH-C(CH3)=CH-CH2-`.\n\nThe image shows the terminal group as `CH2=C(CH3)-` meaning the double bond is between atoms 1 and 2, with the methyl on atom 2 instead of atom 3. Looking at the connectivity, atom 2 is `[CH:2]` but should be `[C:2]` (no H, bearing the methyl), and atom 3 currently `[C:3]` bearing CH3 should become `[CH:3]`.\n\nThis means the methyl group (atom 4) needs to move from atom 3 to atom 2.\n\n```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 4}, \"from_atom\": {\"map_num\": 3}, \"to_atom\": {\"map_num\": 2}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 4 + }, + "from_atom": { + "map_num": 3 + }, + "to_atom": { + "map_num": 2 + } + }, + "restored_smiles": "C=C(C)C=CCC1(C)C(OC(=O)c2ccc(O)cc2)CC(C)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000199", + "op_type": "move_substituent", + "image_path": "images/000199.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][c:15]([Cl:14])[cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "Looking at the image, the sulfur is directly bonded to the naphthalene ring (specifically to a ring carbon), not through an NH group. In the wrong SMILES, there's an NH (atom map :4) between the chain and the sulfur, but in the correct molecule, the sulfonamide nitrogen is between the ethylamine chain and the sulfur, and the sulfur connects directly to the aromatic ring.\n\nComparing the wrong SMILES and the image more carefully:\n\n- Wrong SMILES: `[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1...` \u2014 S is bonded to c8 at position 1 of the naphthalene.\n- Image: S is bonded to the naphthalene at a different position. The Cl is on position 5 of the naphthalene.\n\nLooking at the connectivity in the image, the Cl is at position 5 of the naphthalene (on the second ring, at a peri-like position relative to S). In the wrong SMILES, Cl is at atom :14 bonded to atom :15. The issue is that in the wrong SMILES, the S is attached to c8 (position 1), but in the image the S appears to be attached to what would be position 2 (adjacent position).\n\nRe-examining: the wrong SMILES has S bonded to atom :8, and the naphthalene ring goes 8-9-10-11-12-13-15-16-17-18 with Cl on :15. In the image, the Cl is clearly on the opposite ring from S, at a specific position. The key structural difference is that the bond between S and the ring should be at a different carbon \u2014 specifically, S should be on atom :18 instead of :8, or equivalently, we need to move the S attachment.\n\nActually, re-examining more carefully: the sulfonyl group in the image is attached at position 1, and Cl is at position 5. The wrong SMILES has Cl on atom 15 which is c3 of the second ring. In the image, Cl appears to be on the position corresponding to atom :17 rather than :15.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 14}, \"from_atom\": {\"map_num\": 15}, \"to_atom\": {\"map_num\": 17}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 15 + }, + "to_atom": { + "map_num": 17 + } + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2cccc(Cl)c12", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000202", + "op_type": "move_substituent", + "image_path": "images/000202.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:26]2([O:27][C:28]([CH3:29])=[O:30])[CH:25]=[C:24]3[CH:23]([CH:32]1[CH2:31]2)[CH:39]([O:40][C:41]([CH3:42])=[O:43])[O:38][CH:33]3[O:34][C:35]([CH3:36])=[O:37]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to identify the structural difference.\n\nThe wrong SMILES has atom map :6 as CH2 (a methylene group), but in the correct molecule image, this position should have an oxygen-acetyl group attached, indicating it bears an OAc substituent. Looking more carefully at the image, I can see that the CH2 at position 6 should actually be a CH with an OAc (acetoxy) group attached.\n\nExamining the image closely, I see there's an acetoxy group (OC(=O)CH3) connected to the carbon chain between the ring system and the side chain. In the wrong SMILES, atom :6 is CH2, but in the correct structure it should be CH with an OAc group.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 6}, \"group\": \"OH\"}\n\nWait, let me re-examine. The image shows three acetoxy groups and one hydroxybenzoyl group. The wrong SMILES already has acetoxy groups at atoms 12, 39, and 33, plus the benzoyl at 12. Let me look at what's different.\n\nComparing carefully: in the image, the side chain carbon (position 6 area) has an OAc group. But in the wrong SMILES, atom 6 is CH2 with no substituent. The correct molecule shows this should carry an OAc.\n\nBut since the SMILES already has three OAc groups matching the image, let me check bond orders. Looking at the bond between atoms 24 and 25: in the SMILES it's CH=C (double bond), which matches the image's cyclohexene ring.\n\nRe-examining: the difference is that atom :1 is CH2= (terminal alkene) in the wrong SMILES, but in the image the terminal group is CH2= which looks correct. Let me check atom :3 \u2014 it has a methyl branch and is C=CH. In the image, this matches.\n\nAfter careful comparison, the key difference is the bond between atoms :5 and :6. In the wrong SMILES, this is a single bond (CH=CH-CH2), but looking at the image, there appears to be a double bond at that position (E configuration of the side chain).\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 6}}, \"order\": \"DOUBLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000208", + "op_type": "move_substituent", + "image_path": "images/000208.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:18]2[O:16][CH3:17])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "Looking at the image, I can see the trimethoxyphenyl substituent has three methoxy groups. Comparing the image to the SMILES, I need to check the substitution pattern on that ring.\n\nIn the wrong SMILES, the ring `[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:18]2[O:16][CH3:17]` has methoxy groups at positions 9, 12, and 18 (three adjacent positions with two CH between them).\n\nLooking at the image carefully, the phenyl ring attached to the main scaffold has three methoxy groups in a 3,4,5-trimethoxy pattern, meaning the middle position (between the two OCH3-bearing carbons on either side) should also bear OCH3. In the wrong SMILES, atom 15 is `[cH:15]`, but in the correct molecule this should bear a methoxy group to give a symmetric 3,4,5-trimethoxy pattern.\n\nWait, let me re-examine. The wrong SMILES has OMe at atoms 9, 12, and 18. The image shows a symmetric 3,4,5-trimethoxyphenyl group. Atom 8 is `[cH:8]` and atom 15 is `[cH:15]`. The pattern in the SMILES gives consecutive substitution at 9,12,18 with H at 8 and 15 \u2014 that's three OMe groups at positions 2,3,6 of the ring (not symmetric).\n\nIn the image, the three OMe groups are at 3,4,5 positions (symmetric). This means the OMe on atom 18 should move to atom 15 to create the symmetric pattern.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 16}, \"from_atom\": {\"map_num\": 18}, \"to_atom\": {\"map_num\": 15}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 16 + }, + "from_atom": { + "map_num": 18 + }, + "to_atom": { + "map_num": 15 + } + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000213", + "op_type": "swap_substituents", + "image_path": "images/000213.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[n:3][cH:4][c:5]([CH2:6][c:26]2[n+:7]([CH3:27])[cH:8][s:9][c:10]2[CH2:11][CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:18](=[O:19])([OH:20])[O:21][P:22](=[O:23])([O-:24])[OH:25])[c:28]([NH2:29])[n:30]1", + "correct_smiles": "Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)c2C)c(N)n1", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES:\n\nThe image shows a thiazolium ring connected to a pyrimidine via a CH2 bridge, with the pyrimidine having a methyl group and an amino group. The key difference is that in the wrong SMILES, the methyl group is on atom :2 (adjacent to the nitrogen :3), but in the image, the methyl group should be on atom :4 (the carbon between the two nitrogens of the pyrimidine, i.e., at the 2-position corresponding to the bottom of the ring near \"N\").\n\nLooking more carefully at the image: the pyrimidine ring has NH2 on one carbon and CH3 at the bottom position (near the lower nitrogen). In the wrong SMILES, the CH3 at :1 is attached to :2, but in the correct molecule, it should be attached to :4.\n\nThis is a MoveSubstituent action \u2014 moving the CH3 (atom :1) from atom :2 to atom :4.\n\n```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 1}, \"from_atom\": {\"map_num\": 2}, \"to_atom\": {\"map_num\": 4}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 1 + }, + "from_atom": { + "map_num": 2 + }, + "to_atom": { + "map_num": 4 + } + }, + "restored_smiles": "Cc1ncnc(N)c1Cc1c(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)sc[n+]1C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000209", + "op_type": "swap_substituents", + "image_path": "images/000209.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:6]1[c:5](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[n:35](-[c:36]2[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]2)[c:33](=[O:34])[c:32]2[c:19]1[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][n:30]1)[cH:31]2", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to identify the difference.\n\nThe wrong SMILES has three methoxy groups on the pendant phenyl ring (atoms 10/11, 13/14, 16/17), corresponding to 3,4,5-trimethoxyphenyl. The image also shows a 3,4,5-trimethoxyphenyl group.\n\nLet me trace through more carefully. The image shows the pyridine ring connected via OCH2 to the naphthalene-like aromatic system. Looking at the wrong SMILES, atom 30 is nitrogen in the pyridine ring.\n\nComparing the overall structure, the image shows the same connectivity. Let me check the methoxy groups on the trimethoxyphenyl ring more carefully.\n\nIn the image, I see three OMe groups on the lower phenyl ring. The SMILES has OMe at positions corresponding to atoms 9, 12, and 15. This matches.\n\nNow let me look at the aminophenyl group. The image shows NH2 on the para position of the phenyl attached to nitrogen - this matches.\n\nLet me re-examine the pyridine ring. In the wrong SMILES, the pyridine has nitrogen at position 30. Looking at the image, the pyridine ring shows nitrogen at a specific position. The SMILES encodes: `[cH:26][cH:27][cH:28][cH:29][n:30]` \u2014 this is a 2-pyridyl (nitrogen adjacent to the CH2 attachment point, atom 25).\n\nIn the image, the nitrogen appears to be at the position opposite to the CH2 attachment, which would make it a 3-pyridyl or 4-pyridyl. Looking more carefully at the image, the N appears to be at the 3-position relative to the CH2 linkage.\n\nActually, examining the image closely, the nitrogen in the pyridine ring is at the position para to the attachment point \u2014 that would be a 4-pyridinyl. The wrong SMILES has a 2-pyridinyl (nitrogen ortho to attachment).\n\nTo fix this, I need to move the nitrogen from atom 30 (ortho) to atom 28 (para position).\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 28}, \"atom2\": {\"map_num\": 30}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 28 + }, + "atom2": { + "map_num": 30 + } + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)n(-c2ccc(N)cc2)c(=O)c2cc(OCc3ccccn3)ccc12", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000210", + "op_type": "swap_substituents", + "image_path": "images/000210.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:13]1[c:7]([CH3:14])[cH:8][cH:9][c:10]([Cl:11])[cH:12]1", + "correct_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "predicted_raw": "Looking at the image, the correct molecule has:\n- A methyl ester group (CH3-O-C(=O)-CH2-)\n- Connected via oxygen to a benzene ring\n- The oxygen connects to one ring carbon, the methyl (CH3) is on the adjacent carbon, and Cl is on the para position relative to the oxygen.\n\nIn the image, the oxygen links to a ring carbon, and the methyl group is on the neighboring carbon (ortho to O), with Cl at the para position to the methyl group (which is meta to O... let me look more carefully).\n\nThe image shows: O is at one position, CH3 is on the adjacent carbon (ortho), and Cl is two carbons away from CH3 (para to O).\n\nIn the wrong SMILES, the ring connectivity is: O6-c13-c7(CH3)-cH8-cH9-c10(Cl)-cH12-c13. So the methyl is on c7 (adjacent to c13 where O attaches), and Cl is on c10 (para to c13).\n\nIn the image, the methyl is on the carbon adjacent to the O-bearing carbon but on the other side \u2014 it's ortho but the Cl appears to be para to the CH3, meaning Cl is meta to O.\n\nComparing: In the wrong SMILES, CH3 is ortho to O and Cl is para to O. In the image, CH3 is ortho to O and Cl is para to CH3 (i.e., meta to O).\n\nSo Cl needs to move from c10 (para to O/c13) to c9 (meta to O). This means swapping what's on c9 and c10.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 9}, \"atom2\": {\"map_num\": 10}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 9 + }, + "atom2": { + "map_num": 10 + } + }, + "restored_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000212", + "op_type": "swap_substituents", + "image_path": "images/000212.png", + "wrong_smiles_mapped": "[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([CH2:10][CH2:11][Cl:12])[n:7][cH:8][n:9]2[n:13]([CH3:14])[c:15]1=[O:16]", + "correct_smiles": "Cn1c(=O)c2c(ncn2CCCl)n(C)c1=O", + "predicted_raw": "Looking at the image, I can see the correct molecule is a xanthine-like structure with:\n- Two carbonyl groups (C=O)\n- Two N-CH3 groups\n- A chloroethyl chain attached to a nitrogen\n- An imidazole ring fused to a pyrimidine ring\n\nComparing the wrong SMILES to the image, I need to check where the N-CH3 groups are. In the image, there's a methyl group on the nitrogen at the top right (between the two C=O groups) and another methyl on the nitrogen at the bottom right of the five-membered ring.\n\nIn the wrong SMILES, atom :13 is a nitrogen with a CH3 group (:14), and atom :2 is a nitrogen with a CH3 group (:1). The chloroethyl chain is on atom :6.\n\nLooking at the image carefully, the N-CH3 at the bottom right is on the imidazole nitrogen (atom :13), and the N-CH3 at the top is on atom :2. The chloroethyl group is attached to atom :7 (the other imidazole nitrogen).\n\nIn the wrong SMILES, the chloroethyl chain (CH2CH2Cl) is attached to atom :6 (a carbon), but in the image it should be attached to atom :7 (the nitrogen). Let me re-examine.\n\nThe wrong SMILES has `[c:6]([CH2:10][CH2:11][Cl:12])` \u2014 the chloroethyl is on carbon :6. But in the image, the chloroethyl chain is on the nitrogen :7 of the imidazole ring.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 10}, \"from_atom\": {\"map_num\": 6}, \"to_atom\": {\"map_num\": 7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 9 N, 4, is greater than permitted" + }, + { + "id": "000211", + "op_type": "swap_substituents", + "image_path": "images/000211.png", + "wrong_smiles_mapped": "[CH3:1][NH:2][C:3](=[O:4])[CH:26]1[CH:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([NH2:19])[cH:20][cH:21]4)[n:22][cH:23][n:24][c:25]23)[O:6][CH:5]([OH:27])[CH:28]1[OH:29]", + "correct_smiles": "CNC(=O)C1OC(n2cnc3c(NCc4ccc(N)cc4)ncnc32)C(O)C1O", + "predicted_raw": "Looking at the image, I need to trace the correct molecule structure and compare it with the wrong SMILES.\n\nIn the image, the sugar ring has:\n- An oxygen in the ring\n- A carbon connected to the purine via N\n- Carbons with OH groups\n- A carbon connected to O in the ring, and that same carbon is connected to C(=O)NHMe\n\nIn the wrong SMILES, the connectivity around the sugar ring is: `[CH:26]1[CH:7](...)[O:6][CH:5]([OH:27])[CH:28]1[OH:29]` with `[CH:26]` bonded to `[C:3](=[O:4])`.\n\nLooking at the image carefully, the carbon at the top right connects to both the ring oxygen AND the NH-CH3 group. In the image, there's no OH on that carbon (atom 5) \u2014 instead, atom 5 connects to O in the ring and to C(=O). The OH:27 on atom 5 appears to be wrong.\n\nComparing the image structure with the SMILES: In the image, the carbon bearing the C(=O)NHMe group is directly bonded to the ring oxygen. Atom 5 has an OH:27 group that shouldn't be there \u2014 instead, atom 5 should be directly part of the ring connecting to the carbonyl carbon (atom 3).\n\nActually, let me re-examine. The wrong SMILES has the ring as: atom26-atom7-O6-atom5(OH27)-atom28(OH29)-atom26, and atom26 is bonded to C3(=O4). In the image, the C(=O)NHMe is on the carbon bonded to the ring oxygen. So atom 5 is bonded to O6 and to C3. The OH on atom 5 (OH:27) needs to be removed, making atom 5 a CH2 or just having two ring bonds + bond to C3.\n\nWait \u2014 looking more carefully at the image, the top-right carbon connects to: ring O, NH(CH3) via C=O, and the adjacent ring carbon. That's three connections for that carbon, no OH. So removing the OH group from atom 5 is the fix.\n\n```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 5}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 5 + }, + "group": "OH" + }, + "restored_smiles": "CNC(=O)C1C(O)COC1n1cnc2c(NCc3ccc(N)cc3)ncnc21", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000214", + "op_type": "swap_substituents", + "image_path": "images/000214.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([Cl:3])[c:6]1[cH:5][c:4]([Cl:7])[c:10]([Cl:11])[cH:9][cH:8]1", + "correct_smiles": "O=C(Cl)c1cc(Cl)ccc1Cl", + "predicted_raw": "Looking at the wrong SMILES, I need to parse the structure:\n\nThe wrong SMILES `[O:1]=[C:2]([Cl:3])[c:6]1[cH:5][c:4]([Cl:7])[c:10]([Cl:11])[cH:9][cH:8]1` represents a dichlorobenzoyl chloride with:\n- C(=O)Cl group attached to the ring at atom 6\n- Cl at atom 4 (meta position relative to C=O)\n- Cl at atom 10 (para position relative to C=O)\n\nThis gives a 3,4-dichloro substitution pattern on the ring.\n\nThe image shows 2,5-dichlorobenzoyl chloride:\n- Cl ortho to the C(=O)Cl group (position 2)\n- Cl at position 5 (para to the ortho-Cl)\n\nComparing: In the wrong molecule, Cl:11 is on atom 10 (adjacent to atom 4 which has Cl:7). In the image, the second Cl should be on atom 5 instead of atom 10. So I need to move the Cl from atom 10 to atom 5.\n\nLooking at the ring: atoms 6-5-4-10-9-8. The C(=O)Cl is on atom 6. In the image, Cl is on the ortho carbon (atom 5, next to atom 6) and on atom 9 or the position para to that. \n\nActually, re-examining: the wrong molecule has Cl on atoms 4 and 10 (positions 3,4 relative to the acyl group). The correct molecule needs Cl on atoms 4 and 5 (positions 2,5 \u2014 i.e., ortho and meta on the other side).\n\nWait \u2014 let me recount. Ring: 6\u21925\u21924\u219210\u21929\u21928\u21926. Acyl on 6. Image shows Cl ortho (atom 5) and Cl at atom 4 would be meta... \n\nThe correct molecule is 2,4-dichlorobenzoyl chloride: Cl ortho at atom 5, Cl at atom 10. So the Cl needs to move from atom 4 to atom 5.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 7}, \"from_atom\": {\"map_num\": 4}, \"to_atom\": {\"map_num\": 5}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 7 + }, + "from_atom": { + "map_num": 4 + }, + "to_atom": { + "map_num": 5 + } + }, + "restored_smiles": "O=C(Cl)c1ccc(Cl)cc1Cl", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000215", + "op_type": "swap_substituents", + "image_path": "images/000215.png", + "wrong_smiles_mapped": "[CH3:1][C:8]12[C:2]([CH3:9])([CH3:10])[CH:3]=[CH:4][CH:5]1[CH2:6][CH2:7]2", + "correct_smiles": "CC12C=CC(CC1)C2(C)C", + "predicted_raw": "Looking at the image, I see a bicyclo[2.2.1]heptane (norbornane) skeleton with a cyclopropane ring fused to it, and methyl groups. This is a tricyclic structure.\n\nLet me analyze the wrong SMILES: `[CH3:1][C:8]12[C:2]([CH3:9])([CH3:10])[CH:3]=[CH:4][CH:5]1[CH2:6][CH2:7]2`\n\nThis represents a bicyclo[2.2.1]heptene with gem-dimethyl at C2 and a methyl at C8. The bridgehead C8 has a methyl group attached.\n\nLooking at the correct molecule in the image, I see the gem-dimethyl group is present, and there's a double bond in the five-membered ring portion. But the methyl at C1 (attached to C8) should instead form a cyclopropane ring \u2014 the image shows a three-membered ring (cyclopropane) fused to the norbornane skeleton rather than a simple methyl substituent.\n\nComparing the structures: In the wrong SMILES, atom :1 is a CH3 group attached to bridgehead :8. In the correct image, there's a cyclopropane ring connecting atoms in the norbornane framework. The cyclopropane appears to bridge between C8 and C5 (or a nearby carbon), meaning the CH3 at :1 should instead be connected to form a bond creating the three-membered ring.\n\nThe cyclopropane spans between the bridgehead carbon :8 and carbon :5, with :1 being the CH2 of the cyclopropane. So atom :1 needs a bond to atom :5 to close the three-membered ring, and :1 should be CH2 not CH3.\n\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 5}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC1(C)C=CC23CCC12C3", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000217", + "op_type": "flip_chirality", + "image_path": "images/000217.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@@H:5]([OH:6])[CH2:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[C:13](=[O:14])[CH2:15][C@@:16]2([CH3:17])[C@H:18]1[CH2:19][CH2:20][C@@:21]2([OH:22])[C:23](=[O:24])[CH2:25][OH:26]", + "correct_smiles": "C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO", + "predicted_raw": "Looking at the wrong SMILES and comparing it to the image:\n\nThe image shows a steroid structure with a double bond in the B/C ring junction area (between the rings), which appears to be a \u03944 or similar enone-type unsaturation. Looking at the wrong SMILES, the bond between atoms 11 and 12 (or nearby) needs examination.\n\nIn the image, I can see the C=O at position 11 (the ketone in ring C) and there's a C=C double bond between what corresponds to atoms 11 and 12 in the wrong SMILES. Currently in the wrong SMILES, the bond between atoms 11 and 12 is single (both are [C@@H]), but in the image there's a double bond there (making it part of an enone system with the C=O at atom 14).\n\nLooking more carefully at the image, the double bond is between the carbon bearing the ring junction H atoms \u2014 specifically between atoms 8 and 11, which would create the conjugated enone with the C=O (atoms 13-14).\n\nExamining the connectivity: atom 8 connects to atom 11, and in the correct structure this should be a double bond (consistent with the enone visible in the image).\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 11}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "No bond between atom idx 7 and 10" + }, + { + "id": "000218", + "op_type": "swap_substituents", + "image_path": "images/000218.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[c:11]([CH2:12][CH2:13][N:14]([CH3:15])[CH3:16])[cH:17][c:18]3[c:19]([c:20]2[O:21][CH3:22])[O:23][CH2:24][O:25]3)[c:26]([O:31][CH3:32])[c:30]1[C:27](=[O:28])[OH:29]", + "correct_smiles": "COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(C(=O)O)c1OC", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES:\n\nThe image shows the molecule has a COOH (carboxylic acid) group attached to the central CH carbon (atom 9), and the right-side ring has two OMe groups but no carboxylic acid group on it.\n\nIn the wrong SMILES, atom 30 on the left ring bears a C(=O)OH group (atoms 27, 28, 29), and atom 26 has an OMe group. But in the image, the carboxylic acid is on the central carbon (atom 9), not on the aromatic ring.\n\nLooking more carefully at the image: the central carbon has OH and C=O attached (i.e., a COOH), plus it connects to the two aromatic ring CH2 groups. In the wrong SMILES, atom 9 is CH2 but should be CH with a COOH attached. Meanwhile, atoms 27/28/29 (the C(=O)OH on atom 30) should not be there, and atom 30 should just be a regular cH.\n\nThe fix is to move the carboxylic acid substituent from atom 30 to atom 9.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 27}, \"from_atom\": {\"map_num\": 30}, \"to_atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 27 + }, + "from_atom": { + "map_num": 30 + }, + "to_atom": { + "map_num": 9 + } + }, + "restored_smiles": "COc1ccc(C(=O)C(C(=O)O)c2c(CCN(C)C)cc3c(c2OC)OCO3)c(OC)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000216", + "op_type": "swap_substituents", + "image_path": "images/000216.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[S:5])([O:6][CH2:7][CH3:8])[O:9][c:12]1[cH:11][c:10]([CH3:13])[n:15][nH:14]1", + "correct_smiles": "CCOP(=S)(OCC)Oc1cc(C)[nH]n1", + "predicted_raw": "Looking at the image, I can see the phosphorothioate group is connected to the pyrazole ring at a specific position. Let me trace the structure:\n\nThe image shows:\n- A pyrazole ring with NH, and a methyl group on one carbon\n- The P(=S)(OEt)2 group is connected via oxygen to a carbon of the pyrazole\n\nIn the wrong SMILES, the P-O is connected to atom :12 (a carbon in the pyrazole), and the methyl group :13 is on atom :10.\n\nLooking at the image carefully:\n- The O-P connects to C3 of the pyrazole (the carbon between the two nitrogens is not the one with O attached)\n- The methyl is on C5 (adjacent to NH)\n- The phosphorothioate oxygen connects to C5... \n\nLet me re-examine: In the image, going around the pyrazole ring, the NH is at top right, the carbon with CH3 is adjacent to NH (bottom right), then a CH, then N (top middle-left area), then back to NH. The O-P connects to the C that is between N= and CH(CH3).\n\nIn the wrong SMILES: `[O:9][c:12]1[cH:11][c:10]([CH3:13])[n:15][nH:14]1` \u2014 the O is on :12, and the methyl is on :10. The connectivity is: O-c12=cH11-c10(CH3)-n15=nH14-c12.\n\nIn the image, the methyl group is on the carbon adjacent to NH (atom next to nH:14), which would be atom :15's neighbor. Currently the methyl is on :10 which is bonded to :15(n) and :11(cH). The atom adjacent to nH:14 is :15 and :12. \n\nThe methyl needs to move from atom :10 to atom :12 (or equivalently, the O-P needs to swap). Looking more carefully at the image: the O connects to the C between the two N atoms (C3 position), and CH3 is on C5 (next to NH).\n\nSo the methyl should be on atom :12 (adjacent to nH:14) and the O-P should be on atom :10. This means swapping the substituents on atoms :10 and :12.\n\n```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 10}, \"atom2\": {\"map_num\": 12}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 12 + } + }, + "restored_smiles": "CCOP(=S)(OCC)Oc1cc(C)[nH]n1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000219", + "op_type": "swap_substituents", + "image_path": "images/000219.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([F:18])[cH:16][c:17]1[N:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1", + "correct_smiles": "CN(C)c1ccc(N=Nc2ccccc2)cc1F", + "predicted_raw": "Looking at the image, the fluorine is on the carbon adjacent to the NMe2 group (on the same ring), specifically at the position between the NMe2-bearing carbon and the azo-bearing carbon, closer to the NMe2 side.\n\nIn the wrong SMILES, the fluorine (F:18) is on atom :7 (which is the carbon para to NMe2, adjacent to the azo linkage side). But in the correct molecule, the fluorine should be on the carbon adjacent to the NMe2-bearing carbon on the other side \u2014 that would be atom :17.\n\nLet me trace the wrong SMILES ring: the ring is c:4(NMe2) - c:5 - c:6 - c:7(F) - c:16 - c:17 - back to c:4. The azo group (N=N) is on c:17.\n\nIn the image: the NMe2 is at one position, F is on the carbon adjacent to NMe2, and the azo N=N is on a carbon that is para to NMe2. So F should move from atom :7 to atom :16 (adjacent to NMe2-bearing carbon :17... wait, let me re-examine).\n\nActually, looking at the image more carefully: NMe2 is on the left, F is below it on an adjacent carbon, and the azo group is on the carbon across the ring. In the SMILES, the azo is on :17, NMe2 is on :4. F is on :7 in the wrong SMILES. In the image, F should be on :16 (the carbon between :17 and :7, adjacent to :17 which bears NMe2's neighbor).\n\nRe-reading: ring order is :4-:5-:6-:7-:16-:17-:4. NMe2 on :4, azo on :17, F on :7. In the image, F is adjacent to NMe2 carbon, so it should be on :5 or :17. Since :17 has the azo group, F must be on :5.\n\nThe fix is to move F from atom :7 to atom :5.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 18}, \"from_atom\": {\"map_num\": 7}, \"to_atom\": {\"map_num\": 5}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 18 + }, + "from_atom": { + "map_num": 7 + }, + "to_atom": { + "map_num": 5 + } + }, + "restored_smiles": "CN(C)c1c(F)cccc1N=Nc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000222", + "op_type": "flip_chirality", + "image_path": "images/000222.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([c:18]3[cH:19][cH:20][c:21](=[O:22])[o:23][cH:24]3)[CH2:25][CH2:26][C@:27]12[OH:28]", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "predicted_raw": "Looking at the image, I can see a steroid framework with an OH group at C-27 (not at C-28 as a separate OH), and the lactone ring attached. Comparing the correct molecule in the image with the wrong SMILES:\n\nThe wrong SMILES has a methyl group [CH3:16] on atom 15, but in the image, the corresponding position shows a hydrogen (no methyl). Instead, looking more carefully at the steroid skeleton in the image, atom 2 has a methyl group [CH3:1] which is correct.\n\nLet me re-examine: The wrong SMILES has both [CH3:1] (methyl at C2) and [CH3:16] (methyl at C15). In the image, I can see only one angular methyl group on the steroid. The C15 position should not have a methyl group \u2014 it should be a CH2 instead of a quaternary carbon with methyl.\n\nLooking more carefully at the image, C15 appears to be a CH (not a quaternary C with CH3). The methyl group at atom 16 needs to be removed, and atom 15 should become a CH.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 15}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 15 + }, + "group": "CH3" + }, + "restored_smiles": "C[C@]12CC[C@H](O)C[C@@H]1CCC1C2CC[C@@H]2[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000220", + "op_type": "swap_substituents", + "image_path": "images/000220.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([F:13])[c:9]([OH:10])[cH:11][c:12]1[OH:8]", + "correct_smiles": "NCC(O)c1cc(O)c(O)cc1F", + "predicted_raw": "Looking at the image, the correct molecule has:\n- A benzene ring with F at one position, and two OH groups on adjacent carbons\n- A side chain with CH(OH)CH2NH2\n\nIn the wrong SMILES, the ring has three substituents: F (at atom 7), OH (at atom 9), and OH (at atom 12). That's two OHs and one F on the ring, plus the side chain at atom 5.\n\nComparing the image to the wrong SMILES, the issue is that atom 8 (OH at position 12) needs to be removed and there's no OH there in the correct molecule \u2014 wait, let me re-examine.\n\nThe image shows: F on the ring, two OH groups on the ring (meta to each other, at positions 4 and 5 relative to the side chain), and the side chain.\n\nThe wrong SMILES ring: c5-c6-c7(F)-c9(OH)-c11-c12(OH) with the side chain at c5. That gives F and two OHs on the ring, plus the side chain \u2014 matching the image.\n\nBut the wrong SMILES has atom 8 as OH on c12. Let me recount: `[c:5]1[cH:6][c:7]([F:13])[c:9]([OH:10])[cH:11][c:12]1[OH:8]`\n\nThe image shows the two ring OHs are on adjacent carbons (4,5-dihydroxy pattern). In the wrong SMILES, OH groups are at c9 and c12, which are separated by one carbon (c11). That matches a 1,3 pattern on the ring relative to each other.\n\nLooking more carefully at the image, the F is ortho to the side chain, and the two OHs are at positions 4 and 5 (adjacent). In the wrong SMILES, F(c7) and OH(c9) are separated by one carbon, and OH(c12) is adjacent to c5. The OHs at c9 and c12 are separated by c11 \u2014 they are NOT adjacent.\n\nThe fix: move the OH from c9 to c11 so the two OHs become adjacent.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 10}, \"from_atom\": {\"map_num\": 9}, \"to_atom\": {\"map_num\": 11}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 9 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": "NCC(O)c1cc(F)cc(O)c1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000223", + "op_type": "flip_chirality", + "image_path": "images/000223.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[C:11]1=[C:12]([CH2:13][C@H:14]([CH3:15])[O:16][C@H:17]1[CH3:18])[C:19]2=[O:20]", + "correct_smiles": "COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C2=O", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES:\n\nThe image shows a molecule where the carbon between the two carbonyl groups (C=O) is connected to a hydrogen (it's a CH, not a bare C at the ring junction). Specifically, atom :8 in the wrong SMILES is at the ring junction between the aromatic ring and the quinone system. \n\nExamining more carefully: In the image, the junction between the two rings (connecting the aromatic ring to the cyclohexanone/pyran system) has CH groups rather than bare carbons. The wrong SMILES has atom :8 as a bare carbon `[C:8]`, but in the correct molecule this should be a CH \u2014 indicating the ring junction is not fully conjugated but has a hydrogen.\n\nComparing the wrong SMILES structure to the image: the double bond between C:11 and C:12 in the wrong SMILES makes C:8 part of a conjugated system. In the image, the bond between C:8 and C:9 (or C:8 and C:19) appears to be a single bond with C:8 bearing a hydrogen, meaning the double bond pattern differs.\n\nLooking more carefully at the connectivity: In the image, the bond between C:11 and C:12 appears to be a double bond (part of the enone), and C:8 is sp3 (bearing H). The wrong SMILES has C:8 as sp2. Changing C:8 to have a hydrogen would fix this.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 8}, \"element\": \"C\", \"charge\": 0}\n\nWait, let me reconsider. The key difference is that atom :8 should be a CH (sp3) in the correct molecule.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 19}}, \"order\": \"SINGLE\"}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000229", + "op_type": "flip_chirality", + "image_path": "images/000229.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][CH:16]([OH:17])[C@H:18]1[O:19][CH2:20][C@@H:21]([OH:22])[C@H:23]1[OH:24]", + "correct_smiles": "CCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O", + "predicted_raw": "Looking at the image, I can count the carbon chain length. The correct molecule has a longer alkyl chain than the wrong SMILES. \n\nThe image shows a fatty acid ester with what appears to be a 12-carbon chain (including the carbonyl carbon), while the wrong SMILES has an 11-carbon chain (atoms 1-12, where 12 is the carbonyl carbon). That's 10 CH2/CH3 carbons in the wrong SMILES (atoms 1-11) but the image shows 11 CH2/CH3 carbons.\n\nI need to add one more CH2 group to extend the alkyl chain.\n\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@H]1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000225", + "op_type": "flip_chirality", + "image_path": "images/000225.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:8][CH2:9][CH:10]1[CH:11]2[CH2:12][CH2:13][C:14]2([CH3:15])[CH:16]1[CH2:17][CH2:18][C@H:19]2[OH:20]", + "correct_smiles": "CC12CCCC[C@@H]1CCC1C2CCC2(C)C1CC[C@@H]2O", + "predicted_raw": "Looking at the wrong SMILES, I need to compare it with the correct molecule shown in the image.\n\nThe image shows a steroid skeleton (androstane-type) with an OH group and two methyl groups. The wrong SMILES has only one methyl group (at C2 position, map_num 1) and one methyl group at C14 (map_num 15).\n\nExamining the steroid framework, the correct molecule should have a methyl group at the ring junction corresponding to C10 (in steroid numbering). In the wrong SMILES, atom 2 (C2) has one methyl group (map_num 1), and atom 14 has one methyl group (map_num 15). The image shows methyl groups at both ring junctions (C10 and C13 in steroid numbering).\n\nLooking more carefully at the connectivity, the wrong SMILES has atom 2 with a methyl group attached. In the correct structure, there should also be a methyl group at the other ring junction. Atom 7 corresponds to the other ring junction (C10 in steroid numbering) which in the image appears to have a methyl group but in the wrong SMILES does not.\n\nThe wrong SMILES has `[C@@H:7]` \u2014 this is a CH, meaning no methyl substituent. The correct molecule in the image shows a methyl group at this ring junction.\n\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 7 + }, + "group": "CH3" + }, + "restored_smiles": "CC12CCC3C(CC[C@@]4(C)CCCCC34C)C1CC[C@H]2O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000227", + "op_type": "flip_chirality", + "image_path": "images/000227.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[NH:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15]", + "correct_smiles": "CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O", + "predicted_raw": "Looking at the image, I can see the correct molecule is pantoic acid linked to beta-alanine (pantothenic acid). The structure shows a gem-dimethyl group with a hydroxymethyl group, a chiral center bearing OH, then a C(=O)NH chain to a propionic acid.\n\nComparing the wrong SMILES to the image:\n\nThe wrong SMILES has `[C:2]([CH3:3])([CH2:4][OH:5])` \u2014 this is a quaternary carbon with two methyls and a CH2OH group. But looking at the image, the quaternary carbon has two methyls and a CH2OH, which matches. The chiral center `[C@H:6]([OH:7])` is between the quaternary carbon and the C=O.\n\nWait \u2014 examining more carefully, the wrong SMILES has `[CH3:1]` attached to atom 2. In the image, the quaternary carbon (atom 2) has two CH3 groups and one CH2OH. That matches atoms 1, 3, and 4-5.\n\nThe chiral center in the image has the OH pointing up (wedge). The wrong SMILES has `[C@H:6]`. Looking at the stereochemistry in the image versus the SMILES, the OH is on a wedge bond going up, suggesting the chirality should be `@@` rather than `@`. This is a chirality flip.\n\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 6}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 6 + } + }, + "restored_smiles": "CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000221", + "op_type": "swap_substituents", + "image_path": "images/000221.png", + "wrong_smiles_mapped": "[NH2:1][C:2]1=[N:3][CH:4]=[CH:5][c:9]2[cH:8][cH:7][c:6]([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]4[cH:20][c:21]5[n:22][cH:23][cH:24][cH:25][c:26]5[s:27]4)[C:28]3=[O:29])[c:31]1[cH:30]2", + "correct_smiles": "Nc1nccc2ccc(CN3CCC(NS(=O)(=O)c4cc5ncccc5s4)C3=O)cc12", + "predicted_raw": "Looking at the image, I can see the correct molecule has:\n- A thienopyridine (benzothiophene fused with pyridine) attached to the sulfonamide\n- An aminoquinoline group attached via a CH2 linker\n\nComparing with the wrong SMILES, the sulfonamide group is on the thienopyridine and the aminoquinoline is connected via CH2. In the wrong SMILES, the sulfonamide (S atom :16) is connected to the thienopyridine ring (atom :19), and the aminoquinoline (atoms :1-:5, :8-:9, :30-:31) is connected via CH2 (atom :10).\n\nLooking more carefully at the connectivity: in the wrong SMILES, the CH2 (:10) is on atom :6 of the quinoline ring, and the NH2 (:1) is on the aminopyridine part. In the image, the CH2 linker connects from the quinoline ring to the pyrrolidine nitrogen, and the sulfonyl connects from the thienopyridine to the pyrrolidine NH.\n\nThe key difference I see is that in the wrong SMILES, the C=O is at position :29 on atom :28, making it a lactam. In the image, the C=O is clearly present. Let me check the ring system more carefully.\n\nThe wrong SMILES has the aminopyridine as a 6-membered ring (atoms 2,3,4,5,9,31 or similar). In the image, this is clearly a quinoline (two fused 6-membered rings with one nitrogen). The wrong SMILES actually does encode a quinoline fused system.\n\nLooking again at the thienopyridine: in the image, the sulfur is part of a thiophene fused with pyridine. In the wrong SMILES, atom :27 is sulfur in a thienopyridine connected to the sulfonamide.\n\nThe difference: in the wrong SMILES, the pyrrolidinone nitrogen (:11) connects to CH2 (:12) and CH2 (:13), with CH (:14) bearing NH (:15). The carbonyl is C(:28)=O(:29). In the image, the C=O is on the same ring but the connectivity suggests the piperidone/pyrrolidinone orientation might be swapped \u2014 specifically the C=O and N positions.\n\nAfter careful analysis, the issue is that atom :28 should be swapped with atom :11 \u2014 the nitrogen and carbonyl positions in the pyrrolidine ring are reversed. This means moving the substituent (CH2, atom :10) from atom :6 to... \n\nActually, the simplest fix: the bond order between atoms :2 and :3 should be single (it's currently double), and :4-:5 should be double. But looking more carefully, the real difference is that atom :3 (N) in the pyridine ring \u2014 in the image the NH2 is on a carbon adjacent to N in a quinoline.\n\nAfter thorough comparison, the issue is the bond between atoms :4 and :5: it should be a double bond in the image but appears as single (aromatic) context may differ. The actual structural difference is that atom :5 and :9 bond should be a single bond vs aromatic.\n\nThe real fix: the C=O group and N in the pyrrolidinone are swapped. Swap atoms :11 and :28.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 11}, \"atom2\": {\"map_num\": 28}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 28 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (SwapSubstituents): Explicit valence for atom # 10 N, 4, is greater than permitted" + }, + { + "id": "000226", + "op_type": "flip_chirality", + "image_path": "images/000226.png", + "wrong_smiles_mapped": "[CH2:1]=[C:2]([CH3:3])[C@H:4]1[CH2:5][c:6]2[c:7]([cH:8][cH:9][c:10]3[c:11]2[O:12][C@H:13]2[CH2:14][O:15][c:16]4[cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24][c:25]4[C@@H:26]2[C:27]3=[O:28])[O:29]1", + "correct_smiles": "C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES:\n\nThe image shows the correct molecule where atom 29 (O) is connected as part of a furan ring system. In the wrong SMILES, there's an oxygen at position 29 bonded to atom 7, forming a bond that creates a dihydrofuran ring with atom 4. However, examining the connectivity more carefully:\n\nIn the wrong SMILES, the oxygen at map 29 closes a ring back to atom 4 (`[O:29]1`), creating a five-membered ring: C4-C5-c6-c7-O29. \n\nIn the image, the five-membered ring oxygen connects c6 and c7 to form part of a benzofuran system, but looking more closely, the ring closure with O29 goes back to atom 4, which seems consistent.\n\nThe key difference I notice is that in the wrong SMILES, atom 11 (between the aromatic ring and O12) is aromatic lowercase `c`, but in the image, this carbon bears a carbonyl (C=O at position 28), meaning atom 11 should be at a ring junction that's part of the chromone/chromanone system. Looking at the connectivity: atom 27 has `[C:27]3=[O:28]` and connects to atom 11 via ring closure 3. In the image, the C=O is clearly present.\n\nComparing more carefully, the difference is that atom 10 in the wrong SMILES is aromatic (`[c:10]`), but in the image, this carbon is at the junction bearing the ketone, making it sp3/sp2 non-aromatic. Since atom 27 (C=O) connects to atom 10 via ring closure, and atom 10 also connects to atom 11, atom 10 should be a non-aromatic carbon `C` to properly support the ketone system.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "C=C(C)[C@H]1Cc2c(ccc3c2O[C@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000233", + "op_type": "flip_chirality", + "image_path": "images/000233.png", + "wrong_smiles_mapped": "[CH3:1][C@@H:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "C[C@H](N)Cc1ccccc1", + "predicted_raw": "{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 2}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 2 + } + }, + "restored_smiles": "C[C@H](N)Cc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000224", + "op_type": "flip_chirality", + "image_path": "images/000224.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][n:7][c:8]2[c:9]1[n:10][cH:11][n:12]2[C@@H:13]1[O:14][C@@H:15]([CH2:16][OH:17])[C@@H:18]([O:19][P:20](=[O:21])([OH:22])[OH:23])[C@H:24]1[OH:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1", + "correct_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O)c1cccnc1", + "predicted_raw": "Looking at the image, I can see the correct molecule has the phosphate group attached to the 3' position of the ribose sugar, and the hydroxyl is at the 2' position. In the wrong SMILES, the phosphate is on atom 18 (2' position) and the hydroxyl is on atom 24 (3' position).\n\nComparing the wrong SMILES to the image:\n- In the wrong SMILES: atom 18 has the phosphate group, atom 24 has OH\n- In the image: the phosphate should be on the 3' carbon and OH on the 2' carbon\n\nThis means I need to swap the substituents on atoms 18 and 24.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 18}, \"atom2\": {\"map_num\": 24}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 18 + }, + "atom2": { + "map_num": 24 + } + }, + "restored_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO)[C@H](O)[C@@H]1OP(=O)(O)O)c1cccnc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000228", + "op_type": "flip_chirality", + "image_path": "images/000228.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH:5]3[c:6]4[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[c:13]4[CH2:14][CH2:15][CH:16]3[CH:17]1[CH2:18][CH2:19][C@H:20]2[OH:21]", + "correct_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@@H]2O", + "predicted_raw": "Looking at the image, I can see a steroid-like structure (estradiol derivative) with:\n- OH group on the aromatic ring\n- F substituent adjacent to OH on the aromatic ring\n- OH group on the cyclopentane ring (with methyl group)\n\nIn the image, the F is on the carbon closer to the saturated ring system (position 4, adjacent to the ring junction), and OH is on the next carbon (position 3). \n\nIn the wrong SMILES, the OH is on atom :9 and F is on atom :11. Looking at the connectivity, atom :11 is between atom :9 and atom :13 (which connects to the CH2 groups of the saturated ring). So in the wrong SMILES, F is at the position closer to the saturated ring and OH is further away.\n\nIn the image, F is at the position closer to the saturated ring junction and OH is at the position further from it \u2014 which matches the arrangement where F is on :11 and OH is on :9.\n\nWait, let me re-examine. In the wrong SMILES: `[c:9]([OH:10])[c:11]([F:12])` \u2014 atom :9 has OH and atom :11 has F. Atom :11 connects to :13 which connects to CH2 groups leading to the saturated ring.\n\nIn the image, the OH is on the top-right of the aromatic ring and F is on the bottom-right, closer to the saturated ring system. This means F should be on :13 (or near the junction) and OH should stay where it is \u2014 or they need to be swapped.\n\nComparing carefully: in the image, OH is at the 3-position and F is at the 2-position (closer to ring junction). In the wrong SMILES, OH is on :9 and F is on :11. Since :11 is closer to the junction via :13, F is already closer to the junction. This seems correct.\n\nBut re-examining the image more carefully, F is at the 4-position (bottom, adjacent to the saturated ring) and OH is at the 3-position. In the wrong SMILES, the positions appear swapped relative to the image.\n\nThe fix is to swap the substituents on atoms :9 and :11:\n\n```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 9}, \"atom2\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 9 + }, + "atom2": { + "map_num": 11 + } + }, + "restored_smiles": "CC12CCC3c4ccc(F)c(O)c4CCC3C1CC[C@H]2O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000230", + "op_type": "flip_chirality", + "image_path": "images/000230.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@:5]1([C:6]([CH3:7])=[O:8])[C@H:9]([CH3:10])[CH2:11][C@H:12]2[CH:13]3[CH:14]=[C:15]([Cl:16])[C:17]4=[CH:18][C:19](=[O:20])[CH2:21][CH2:22][C:23]4([CH3:24])[C@@H:25]3[CH2:26][CH2:27][C:28]12[CH3:29]", + "correct_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3C=C(Cl)C4=CC(=O)CCC4(C)[C@H]3CCC21C", + "predicted_raw": "Looking at the image, I can see the correct molecule is a steroid derivative with a chlorine substituent and specific stereochemistry. Comparing the image to the wrong SMILES:\n\nIn the image, the atom corresponding to map_num 9 (the CH at the ring junction near the methyl/ethyl substituent region) has a specific stereochemistry. Looking at the wrong SMILES, atom 9 is `[C@H:9]`, but examining the image carefully, I notice the methyl group at that position \u2014 actually, let me compare more carefully.\n\nLooking at the bottom-left portion of the molecule in the image, I see a CH2-CH3 group (ethyl-like chain) coming off the cyclopentane ring, along with a methyl group. In the wrong SMILES, atom 10 is CH3 attached to atom 9. But in the image, that substituent appears to be an ethyl group (CH2CH3), not a methyl.\n\nWait \u2014 re-examining more carefully, the image shows \"CH3\" attached via \"CH\" with a methyl branch. Let me reconsider.\n\nComparing the wrong SMILES to the image systematically: The key difference I can identify is at atom 14. In the wrong SMILES, atom 14 is `[CH:14]` which is part of a double bond `[CH:14]=[C:15]([Cl:16])`. But in the image, looking at the bond between the corresponding positions, this appears to be `[CH2:14]` with a single bond to C15, and the double bond is between C15 and C17 instead.\n\nActually, looking more carefully at the image, the double bond pattern around the Cl-bearing carbon: the C=C double bond is between atoms 15 and 14 in the wrong SMILES, but in the image the Cl is on a carbon that's part of a C=CH arrangement. The difference is that atom 18 in the wrong SMILES shows `=[CH:18]` (double bond to C17), but in the image this should be a single bond, with the double bond repositioned.\n\nRe-examining: In the wrong SMILES, atom 13 is CH and atom 14 is CH with a double bond to 15. In the image, atom 13 appears to be CH2 (no double bond involvement). The fix is changing atom 13 from CH to CH2 by removing aromaticity \u2014 but actually the simplest fix is:\n\nThe bond between atoms 13 and 14 should be a double bond, and the bond between 14 and 15 should be single.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 14}, \"atom2\": {\"map_num\": 15}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 14 + }, + "atom2": { + "map_num": 15 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3CC(Cl)C4=CC(=O)CCC4(C)[C@@H]3CCC21C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000237", + "op_type": "flip_chirality", + "image_path": "images/000237.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[C@H:13]([OH:14])[CH2:15][C@:16]2([CH3:17])[C@@H:18]([c:19]3[cH:20][cH:21][c:22](=[O:23])[o:24][cH:25]3)[CH2:26][CH2:27][C@:28]12[OH:29]", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2[C@H](O)C[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "predicted_raw": "Looking at the image, I can see a steroid framework with a pyranone (\u03b1-pyrone) ring attached. The correct molecule has a double bond in the steroid skeleton (between the C/D ring junction area), which appears to be between atoms 11 and 12 based on the structure.\n\nIn the wrong SMILES, the bond between atoms 11 and 12 is a single bond (both are CH), but in the correct molecule from the image, there's a double bond at that position (C=C), consistent with a bufalin-type structure with a \u039411,12 or similar unsaturation.\n\nComparing more carefully, the image shows a C=C double bond between what corresponds to atoms 11 and 12 in the SMILES.\n\n```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 11}, \"atom2\": {\"map_num\": 12}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "C[C@]12CC[C@H](O)C[C@@H]1CCC1=C2[C@H](O)C[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000238", + "op_type": "flip_chirality", + "image_path": "images/000238.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@H:5]([CH2:6][C:7](=[O:8])[OH:9])[CH2:10][N+:11]([CH3:12])([CH3:13])[CH3:14]", + "correct_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "predicted_raw": "Looking at the image, I see the correct molecule is acetylcarnitine. The stereocenter has the CH2-N+(CH3)3 group on one side and the CH2-COOH group on the other, with the O-acetyl group attached.\n\nComparing the image to the wrong SMILES: The wrong SMILES has the `[C@H:5]` with the O-acetyl on one side, CH2-COOH, and CH2-N+(CH3)3. The image shows the (R)-configuration, but the wrong SMILES encodes the (S)-configuration. The fix is to flip the chirality at atom 5.\n\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 5}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 5 + } + }, + "restored_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000231", + "op_type": "flip_chirality", + "image_path": "images/000231.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C@H:3]1[O:4][C:5](=[O:6])[C@H:7]([CH3:8])[C@@H:9]([O:10][CH:11]2[CH2:12][C:13]([CH3:14])([O:15][CH3:16])[CH:17]([OH:18])[CH:19]([CH3:20])[O:21]2)[CH:22]([CH3:23])[C@@H:24]([O:25][CH:26]2[O:27][CH:28]([CH3:29])[CH2:30][CH:31]([N:32]([CH3:33])[CH3:34])[CH:35]2[OH:36])[C@@:37]([CH3:38])([OH:39])[CH2:40][C@@H:41]([CH3:42])[C:43](=[O:44])[C@H:45]([CH3:46])[C@@H:47]([OH:48])[C@H:49]1[CH3:50]", + "correct_smiles": "CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(C)(OC)C(O)C(C)O2)C(C)[C@@H](OC2OC(C)CC(N(C)C)C2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to trace through the structure carefully.\n\nThe image shows erythromycin A or a closely related macrolide. Examining the macrolactone ring and substituents, I notice that in the image, the atom corresponding to position 22 (between the two sugar attachment points) has a hydroxyl group visible, and atom 24 doesn't appear to carry an OH in the wrong SMILES region where expected.\n\nComparing more carefully: In the wrong SMILES, atom 7 has a CH3 group (atom 8), but looking at the image, the carbon adjacent to the carbonyl (lactone C=O) on that side should bear an H, not a methyl group. \n\nActually, let me re-examine. The key difference I can identify is at the cladinose sugar. In the wrong SMILES, atom 15 is an oxygen connected to atom 16 (OCH3) \u2014 that's the methoxy group on cladinose. Atom 18 is OH on atom 17. Looking at the image's cladinose sugar, I see OH and OCH3 groups present.\n\nLooking more carefully at the macrolide core: in the image, atom 22 between the two sugars appears to not have a methyl substituent \u2014 or rather, comparing the connectivity, I notice that in the wrong SMILES, atom 24 has an oxygen linking to the desosamine sugar, while atom 9 links to cladinose. \n\nAfter careful comparison, the difference is that atom 7 in the wrong SMILES has a methyl group (atom 8), but in the correct structure shown in the image, this position should have a hydrogen (no methyl). This corresponds to the difference between erythromycin derivatives.\n\nWait \u2014 re-examining the image more carefully around the lactone portion: the carbon next to C=O at the bottom-left has an ethyl group and connects to the ring. The issue is that atom 48 (OH on atom 47) \u2014 in the image, that carbon appears to not have an OH group.\n\nAfter thorough analysis, the difference is: atom 22 in the wrong SMILES has a methyl group (atom 23) but in the image, that position carries an OH group instead.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 23}}\n\nHmm, let me reconsider. The most consistent single correction: atom 22 should have OH instead of CH3.\n\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 23}, \"element\": \"O\", \"charge\": 0}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000236", + "op_type": "flip_chirality", + "image_path": "images/000236.png", + "wrong_smiles_mapped": "[CH3:1][C:2]#[C:3][C@:4]1([OH:5])[CH2:6][CH2:7][C@H:8]2[C@@H:9]3[CH2:10][C@H:11]([CH3:12])[C:13]4=[CH:14][C:15](=[O:16])[CH2:17][CH2:18][C@:19]4([CH3:20])[C@H:21]3[CH2:22][CH2:23][C@@:24]12[CH3:25]", + "correct_smiles": "CC#C[C@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C", + "predicted_raw": "Looking at the wrong SMILES and comparing it to the image:\n\nThe wrong SMILES has a methyl group at atom 12 attached to atom 11, and also a methyl group at atom 25 attached to atom 24. The image shows a steroid skeleton. Examining the image carefully, I can see the molecule has a methyl group on atom 11 (in the C/D ring junction area) but does NOT have a methyl group at the C-13 position (atom 24). The angular methyl at C-13 (map_num 25) needs to be removed.\n\nLooking more carefully: the correct molecule in the image is a norethindrone-like structure. The standard structure has no methyl group at C-13 (the 13-position). The wrong SMILES has `[C@@:24]12[CH3:25]` indicating a methyl at that position, but the image shows this should be a hydrogen (nor- steroid, i.e., 19-norsteroid without the C-18 methyl... actually let me reconsider).\n\nRe-examining: The image shows the typical levonorgestrel/norgestrel-type structure. It has the C-18 methyl (at C-13 junction) but does NOT have the C-19 methyl (at C-10 junction). The wrong SMILES has methyl groups at both atom 20 (on atom 19, the C-10 position) and atom 25 (on atom 24, the C-13 position).\n\nThe image clearly shows no methyl at the C-10 position (atom 19) \u2014 this is a 19-norsteroid. So the methyl at map_num 20 should be removed.\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 19}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 19 + }, + "group": "CH3" + }, + "restored_smiles": "CC#C[C@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@@H]4[C@H]3CC[C@]21C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000235", + "op_type": "flip_chirality", + "image_path": "images/000235.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C@@H:3]1[C@@H:4]([O:5][C@@H:6]2[O:7][C@H:8]([CH3:9])[C@@H:10]([O:11][C@H:12]3[CH2:13][C@@:14]([CH3:15])([OH:16])[C@H:17]([O:18][C:19](=[O:20])[CH2:21][CH:22]([CH3:23])[CH3:24])[C@H:25]([CH3:26])[O:27]3)[C@H:28]([N:29]([CH3:30])[CH3:31])[C@H:32]2[OH:33])[C@@H:34]([CH2:35][CH:36]=[O:37])[CH2:38][C@@H:39]([CH3:40])[C:41](=[O:42])[CH:43]=[CH:44][CH:45]2[O:46][CH:47]2[CH2:48][C@@H:49]([CH3:50])[O:51][C:52](=[O:53])[CH2:54][C@H:55]1[O:56][C:57]([CH3:58])=[O:59]", + "correct_smiles": "CO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)C(=O)C=CC2OC2C[C@@H](C)OC(=O)C[C@H]1OC(C)=O", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to identify the structural difference.\n\nIn the wrong SMILES, there's an aldehyde group at atoms 36-37 (`[CH:36]=[O:37]`), where atom 36 is `CH`. Looking at the image, I can see that the corresponding position shows a `CHO` group, but examining more carefully, the image shows a ketone (C=O) at that position rather than an aldehyde with a bare CH.\n\nActually, let me re-examine. The fragment `[CH2:35][CH:36]=[O:37]` represents an aldehyde. Looking at the image carefully, I see that this position should be a `CH2-CH=O` \u2014 but comparing the overall structure, the key difference appears to be the bond between atoms 43 and 44.\n\nIn the wrong SMILES: `[CH:43]=[CH:44]` \u2014 this is a double bond.\nIn the image, looking at the macrolide ring, I can see that the corresponding bond appears to be a single bond (no double bond indication at that position in the macrocyclic ring).\n\nWait, let me look more carefully at the image. The macrolide ring in the image does show a double bond (C=C) in that region. Let me reconsider.\n\nComparing the wrong SMILES to the image more carefully: the aldehyde `[CH:36]=[O:37]` \u2014 in the image, I see a ketone C=O on the macrolide ring, suggesting atom 36 should not have a hydrogen \u2014 it should be a carbon with no H (part of a C=O as a ketone, not an aldehyde).\n\nLooking again at the image, the fragment should be a ketone, meaning atom 36 should be a carbonyl carbon (no H), not a CH.\n\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 35}, \"atom2\": {\"map_num\": 36}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 35 + }, + "atom2": { + "map_num": 36 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@H](OC(=O)CC(C)C)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](C=C=O)C[C@@H](C)C(=O)C=CC2OC2C[C@@H](C)OC(=O)C[C@H]1OC(C)=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000239", + "op_type": "flip_chirality", + "image_path": "images/000239.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@H:11]1[O:12][C@H:13]([CH2:14][O:15][P:16](=[O:17])([OH:18])[OH:19])[C@@H:20]([OH:21])[C@H:22]1[OH:23]", + "correct_smiles": "Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O", + "predicted_raw": "Looking at the image, I see adenosine 5'-monophosphate (AMP). The correct molecule has the amino group on C6 of the purine ring and the ribose connected at N9.\n\nComparing the wrong SMILES to the image:\n\nThe wrong SMILES has the amino group (NH2) attached at position 2 of the purine, with the connectivity `[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2`. This makes the NH2 on the atom adjacent to two nitrogens (atom 2), which corresponds to C2 of the purine \u2014 giving 2-aminopurine.\n\nIn the correct molecule (AMP), the NH2 is on C6 of adenine. I need to move the NH2 from atom 2 to atom 6.\n\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 4}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 4 + } + }, + "restored_smiles": "CC1=NN[N]c2c1ncn2[C@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000234", + "op_type": "flip_chirality", + "image_path": "images/000234.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@@H:11]1[CH2:12][C@H:13]([OH:14])[C@@H:15]([CH2:16][O:17][P:18](=[O:19])([OH:20])[OH:21])[O:22]1", + "correct_smiles": "Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1", + "predicted_raw": "Looking at the wrong SMILES and comparing it to the image:\n\nThe image shows deoxyadenosine monophosphate (dAMP). The key difference is that in the correct molecule, the phosphorus has three OH groups and one =O (i.e., it's a phosphate with three hydroxy groups), but looking more carefully, the image shows P(=O)(OH)(OH) which matches. Let me re-examine.\n\nThe wrong SMILES has the amino group on atom 1 (connected to c:2), and the connectivity goes: NH2-c1-n-ch-n-c2-c1-n-ch-n2. Looking at the image, the NH2 is at the bottom of the purine (on C6 of the adenine), and the numbering in the SMILES connects NH2 to c:2 which connects to n:3.\n\nComparing the purine ring connectivity in the wrong SMILES vs the image: the image shows adenine with standard connectivity. The wrong SMILES has `[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2` \u2014 this is adenine attached via N9 (atom 10) to the sugar.\n\nNow looking at the sugar: the wrong SMILES has a 3'-OH group on atom 13 via atom 14. In the image, this is deoxyadenosine \u2014 there should be no 3'-OH... wait, actually looking again at the image, there IS an OH on the sugar ring (top of the ring). But in deoxyribose, position 2' lacks an OH.\n\nThe wrong SMILES has: C@@H:11 (C1') - CH2:12 (C2') - C@H:13(OH:14) (C3') - C@@H:15 (C4') - O:22 completing the ring. This matches 2'-deoxyribose with 3'-OH.\n\nThe phosphate in the wrong SMILES: P(=O)(OH)(OH) \u2014 that's two OH groups. The image also shows P(=O)(OH)(OH). These match.\n\nLet me recheck chirality. The C4' atom (atom 15) in the image shows the stereochemistry going the opposite way. Comparing the image carefully, the wedge/dash at C1' (atom 11) suggests flipped chirality compared to the wrong SMILES.\n\nLooking at C4' (atom 15): in the image the configuration appears flipped relative to the wrong SMILES.\n\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 15}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 15 + } + }, + "restored_smiles": "Nc1ncnc2c1ncn2[C@@H]1C[C@H](O)[C@H](COP(=O)(O)O)O1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000241", + "op_type": "flip_ez", + "image_path": "images/000241.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "Looking at the image, I see the carboxylic acid group (COOH) is attached to the carbon adjacent to the naphthyl group, and the butenyl chain extends from that same carbon. The COOH is on the carbon at position 5 in the wrong SMILES, but in the image, the COOH is on a separate carbon between the chain and the naphthyl group.\n\nComparing the wrong SMILES structure with the image:\n\nIn the wrong SMILES: the chain is CH3-CH=CH-CH2-CH(COOH)(naphthyl) \u2014 the COOH and naphthyl are on the same carbon (atom 5).\n\nIn the image: the COOH and naphthyl are on separate carbons \u2014 it's CH3-CH=CH-CH2-CH(COOH)-CH(naphthyl)... wait, let me re-examine.\n\nActually, looking more carefully at the image, the structure shows: the COOH is on one carbon, and the naphthyl is on the adjacent carbon (atom 5). The correct structure is: CH3-CH=CH-CH2-C(COOH)-c1... where the COOH is actually on a different carbon.\n\nRe-examining: In the image, COOH is on the carbon between CH2 and the naphthyl-bearing carbon. So the naphthyl is on atom 5, and COOH should be moved from atom 5 to atom 4.\n\nWait \u2014 in the wrong SMILES, atom 4 is CH2 and atom 5 has both COOH and naphthyl. In the image, the COOH is on the carbon that also bears the CH2 chain, not on the naphthyl carbon. So COOH should move from atom 5 to atom 4.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 6}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 4}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 6 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 4 + } + }, + "restored_smiles": "C/C=C\\C(Cc1cccc2ccccc12)C(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000242", + "op_type": "flip_ez", + "image_path": "images/000242.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "Looking at the image, I see the carboxylic acid group (COOH) is attached to the carbon adjacent to the naphthyl group, and the butenyl chain extends from that same carbon. The COOH is on the carbon at position 5 in the wrong SMILES, but in the image, the COOH is on a separate carbon between the chain and the naphthyl group.\n\nComparing the wrong SMILES structure with the image:\n\nIn the wrong SMILES: the chain is CH3-CH=CH-CH2-CH(COOH)(naphthyl) \u2014 the COOH and naphthyl are on the same carbon (atom 5).\n\nIn the image: the COOH and naphthyl are on separate carbons \u2014 it's CH3-CH=CH-CH2-CH(COOH)-CH(naphthyl)... wait, let me re-examine.\n\nActually, looking more carefully at the image, the structure shows: the COOH is on one carbon, and the naphthyl is on the adjacent carbon (atom 5). The correct structure is: CH3-CH=CH-CH2-C(COOH)-c1... where the COOH is actually on a different carbon.\n\nRe-examining: In the image, COOH is on the carbon between CH2 and the naphthyl-bearing carbon. So the naphthyl is on atom 5, and COOH should be moved from atom 5 to atom 4.\n\nWait \u2014 in the wrong SMILES, atom 4 is CH2 and atom 5 has both COOH and naphthyl. In the image, the COOH is on the carbon that also bears the CH2 chain, not on the naphthyl carbon. So COOH should move from atom 5 to atom 4.\n\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 6}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 4}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 6 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 4 + } + }, + "restored_smiles": "C/C=C\\C(Cc1cccc2ccccc12)C(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000244", + "op_type": "flip_ez", + "image_path": "images/000244.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "Looking at the image, I see the carboxylic acid group (COOH) is attached to the carbon adjacent to the naphthyl group, and the butenyl chain extends from that same carbon. The COOH is on the carbon at position 5 in the wrong SMILES, but in the image it should be on the carbon corresponding to position 5's neighbor.\n\nLet me trace the wrong SMILES more carefully:\n- Wrong: `[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1...` \u2014 the COOH and naphthyl are both on atom 5.\n- Image: the COOH and naphthyl are on the same carbon, but the chain connects CH2-CH2 (not CH2-CH). Looking more carefully, the image shows the COOH is on the carbon between the CH2 and the naphthyl \u2014 that matches atom 5.\n\nComparing the stereochemistry: the wrong SMILES has `[CH3:1]/[CH:2]=[CH:3]\\[CH2:4]` which gives (E)-configuration. The image shows the CH3 and CH2 on the same side of the double bond, which is (Z)-configuration.\n\n{\"type\": \"FlipEZ\"}", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000240", + "op_type": "flip_ez", + "image_path": "images/000240.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "Looking at the image, the COOH group is on the carbon adjacent to the naphthyl group (atom 5), and the chain extends from there. Comparing the wrong SMILES to the image:\n\nIn the wrong SMILES, the carboxylic acid (C(=O)OH) is attached to atom 5 (the carbon bonded to the naphthyl group). In the image, the carboxylic acid is on the carbon next to the naphthyl-bearing carbon \u2014 i.e., it should be on atom 4's position relative to atom 5.\n\nWait, let me re-examine. The wrong SMILES has: CH3-CH=CH-CH2-CH(C(=O)OH)(naphthyl). The COOH and naphthyl are both on atom 5.\n\nIn the image, the correct molecule shows: CH3-CH=CH-CH2-CH(naphthyl)-C(=O)OH, where the COOH is on a separate carbon between the chain CH2 and the naphthyl. Actually, looking more carefully at the image, the COOH is on a carbon between the CH2CH=CHCH3 chain and the naphthyl group \u2014 so the structure is CH3CH=CHCH2-CH(COOH)-naphthyl, which matches the wrong SMILES.\n\nLet me reconsider the stereochemistry. The wrong SMILES has `/[CH:2]=[CH:3]\\` which is (E)-configuration. The image shows (E) as well (CH3 and CH2 on opposite sides).\n\nLooking again more carefully at the image: the double bond geometry appears to show CH3 and CH2 on the same side, which would be (Z). The wrong SMILES encodes (E). So the fix is to flip E/Z.\n\n{\"type\": \"FlipEZ\"}", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000232", + "op_type": "flip_chirality", + "image_path": "images/000232.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]1[O:9][c:10]1[cH:11][c:12]3[c:13]([cH:14][c:15]1[O:16][CH3:17])[CH2:18][CH2:19][N+:20]([CH3:21])([CH3:22])[C@@H:23]3[CH2:24][c:25]1[cH:26][cH:27][c:28]([cH:29][cH:30]1)[O:31][c:32]1[c:33]([O:34][CH3:35])[c:36]([O:37][CH3:38])[cH:39][c:40]3[c:41]1[C@@H:42]([CH2:43]2)[N+:44]([CH3:45])([CH3:46])[CH2:47][CH2:48]3", + "correct_smiles": "COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+](C)(C)[C@H]3Cc1ccc(cc1)Oc1c(OC)c(OC)cc3c1[C@@H](C2)[N+](C)(C)CC3", + "predicted_raw": "Looking at the image and comparing it to the wrong SMILES, I need to identify the structural difference.\n\nThe image shows the correct molecule which is a bis-benzylisoquinoline alkaloid (like tubocurarine). Examining the SMILES carefully, I notice the wrong SMILES has an extra methoxy group. Specifically, atom :36 has an OCH3 group (atoms :37 and :38), but in the image, the corresponding ring position doesn't have that methoxy substituent \u2014 it just has a hydrogen.\n\nRemoving the OCH3 group at atom :36:\n\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 36}, \"group\": \"OH\"}\n\nWait, let me re-examine. Looking more carefully at the image, I can count the methoxy groups. The image shows methoxy groups on specific positions. Comparing the two aromatic rings in the lower portion, the wrong SMILES has two OCH3 groups on one ring (at atoms :33 and :36), but the image shows only one OCH3 on that ring.\n\nThe extra group is the OCH3 at position :36 (atoms :37 for O and :38 for CH3). This needs to be removed.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 37}}\n\nHmm, but RemoveAtom only removes one atom. Let me reconsider \u2014 the `RemoveGroup` action should handle removing the OCH3 as a group from anchor :36. The group attached is OCH3, but the available groups don't include \"OCH3\". The closest available is \"OH\". But actually, looking again at the image vs SMILES, atom :36 with O:37 and CH3:38 forms an -OCH3. \n\nRe-examining: the correct molecule in the image has an OH instead of OCH3 at that position.\n\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 38}}", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000243", + "op_type": "flip_ez", + "image_path": "images/000243.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "Looking at the image, I see the carboxylic acid group (COOH) is attached to the carbon adjacent to the naphthyl group, and the butenyl chain extends from that same carbon. The COOH is on the carbon at position 5 in the wrong SMILES, but in the image, the COOH is on a separate carbon between the chain and the naphthyl group.\n\nComparing the wrong SMILES structure with the image more carefully:\n\n- Wrong SMILES: The chain is CH3-CH=CH-CH2-CH(COOH)(naphthyl) \u2014 the COOH and naphthyl are on the same carbon (atom 5), with CH2 (atom 4) connecting to the chain.\n- Image: The COOH is on a carbon between the naphthyl-bearing carbon and the CH2 chain. So the structure is CH3-CH=CH-CH2-CH(COOH)-CH(naphthyl)... wait, looking again at the image, the COOH is on the carbon above, and the naphthyl is below, with the chain going left.\n\nActually, re-examining: in the image, the structure shows HO and O on a carbon, which connects to a CH that bears both the naphthyl and a CH2CH=CHCH3 chain. This matches the wrong SMILES. \n\nThe key difference: in the wrong SMILES, the stereochemistry is `/[CH:2]=[CH:3]\\` which is (E)-configuration. In the image, the CH3 and CH2 are on the same side of the double bond, indicating (Z)-configuration. So the E/Z stereochemistry needs to be flipped.\n\n{\"type\": \"FlipEZ\"}", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + } +] \ No newline at end of file diff --git a/data/benchmark_results_gemini3.json b/data/benchmark_results_gemini3.json new file mode 100644 index 0000000000000000000000000000000000000000..4aa89c07e71db94a6075f17198797b3c0d5a8ce4 --- /dev/null +++ b/data/benchmark_results_gemini3.json @@ -0,0 +1,5222 @@ +[ + { + "id": "000001", + "op_type": "remove_atom", + "image_path": "images/000001.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([O:11][CH3:13])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000002", + "op_type": "add_atom", + "image_path": "images/000002.png", + "wrong_smiles_mapped": "[CH:1]([CH3:2])([CH3:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000000", + "op_type": "change_atom_element", + "image_path": "images/000000.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([SH:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "C" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000003", + "op_type": "remove_bond", + "image_path": "images/000003.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1([CH3:4])[CH2:3][O:9][c:8]2[cH:7][cH:6][c:5]1[cH:12][c:10]2[OH:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 9}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000005", + "op_type": "remove_functional_group", + "image_path": "images/000005.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:13])[c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000010", + "op_type": "remove_atom", + "image_path": "images/000010.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][NH2:14])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000006", + "op_type": "add_functional_group", + "image_path": "images/000006.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 8}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 8 + }, + "group": "OH" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000009", + "op_type": "change_atom_element", + "image_path": "images/000009.png", + "wrong_smiles_mapped": "[NH2:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000012", + "op_type": "change_charge", + "image_path": "images/000012.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[OH+:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 12}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 12 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000004", + "op_type": "add_bond", + "image_path": "images/000004.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:12]1.[OH2:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 11}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000007", + "op_type": "move_substituent", + "image_path": "images/000007.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:7]1[cH:6][cH:5][cH:12][c:10]([OH:11])[c:8]1[OH:9]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 5}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 5 + } + }, + "restored_smiles": "CC(C)(C)c1cc(O)ccc1O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000011", + "op_type": "add_atom", + "image_path": "images/000011.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 11}, \"element\": \"O\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 11 + }, + "element": "O", + "bond_order": "SINGLE" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000013", + "op_type": "change_bond_order", + "image_path": "images/000013.png", + "wrong_smiles_mapped": "[NH:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000017", + "op_type": "add_functional_group", + "image_path": "images/000017.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 6}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 6 + }, + "group": "OH" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000014", + "op_type": "remove_bond", + "image_path": "images/000014.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:10]1)[O:9]2)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 9}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000015", + "op_type": "add_bond", + "image_path": "images/000015.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12].[OH2:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 11}, \"atom2\": {\"map_num\": 13}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 13 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000016", + "op_type": "remove_functional_group", + "image_path": "images/000016.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:14])[c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000018", + "op_type": "move_substituent", + "image_path": "images/000018.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:10]1[OH:9])[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000020", + "op_type": "remove_atom", + "image_path": "images/000020.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH2:14][OH:21])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 13}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "OH" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='OH' not found at anchor=12" + }, + { + "id": "000008", + "op_type": "swap_substituents", + "image_path": "images/000008.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(C)(C)c1cccc(O)c1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000019", + "op_type": "change_atom_element", + "image_path": "images/000019.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([SH:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 14}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000024", + "op_type": "remove_functional_group", + "image_path": "images/000024.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH3:21])[c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 21}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 21 + } + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000022", + "op_type": "remove_bond", + "image_path": "images/000022.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]-2[c:7]2[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]24)[cH:18][c:19]3[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 6}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000021", + "op_type": "add_atom", + "image_path": "images/000021.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 13}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 13 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000023", + "op_type": "add_bond", + "image_path": "images/000023.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Cc1ccc2cc3ccc4cc(C)ccc4c3cc2c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000027", + "op_type": "swap_substituents", + "image_path": "images/000027.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:20][c:19]2[c:5]3[cH:6][c:7]([c:8]([cH:18]2)[CH:4]=[CH:3]1)-[c:17]1[c:11]([cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[CH:10]=[CH:9]3", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 18}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 18 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (RemoveAtom): Can't kekulize mol. Unkekulized atoms: 3 4 5 6 7 10 11 12 13 15 16" + }, + { + "id": "000026", + "op_type": "move_substituent", + "image_path": "images/000026.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][c:15]([CH3:14])[cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 17}, \"from_atom\": {\"map_num\": 7}, \"to_atom\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 17 + }, + "from_atom": { + "map_num": 7 + }, + "to_atom": { + "map_num": 6 + } + }, + "restored_smiles": "Cc1ccc2c(c1)-c1cc(cc3cc(C)ccc13)C=C2", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000030", + "op_type": "change_charge", + "image_path": "images/000030.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[NH+:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 17}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 17 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000028", + "op_type": "remove_atom", + "image_path": "images/000028.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[OH:46])[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 46}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 46 + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000029", + "op_type": "add_atom", + "image_path": "images/000029.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])[OH:33])[cH:34][cH:35][cH:36][c:37]34)[c:38]3[cH:39][cH:40][cH:41][cH:42][c:43]23)[cH:44]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 31}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 31 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000025", + "op_type": "add_functional_group", + "image_path": "images/000025.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]3[c:7]([cH:8][cH:9][c:10]4[cH:11][c:12]([CH3:13])[cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cc3ccc4cc(C)ccc4c3cc2c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000031", + "op_type": "change_bond_order", + "image_path": "images/000031.png", + "wrong_smiles_mapped": "[OH:1][SH:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000034", + "op_type": "remove_functional_group", + "image_path": "images/000034.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[c:13]([Cl:46])[cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 46}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 46 + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000037", + "op_type": "remove_atom", + "image_path": "images/000037.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 12}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000038", + "op_type": "add_atom", + "image_path": "images/000038.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"NH2\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "NH2" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000035", + "op_type": "move_substituent", + "image_path": "images/000035.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][C:12]2=[CH:13][CH:14]=[C:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:41]3[cH:40][cH:39][c:44]2[cH:43][cH:42]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 44}, \"from_atom\": {\"map_num\": 39}, \"to_atom\": {\"map_num\": 40}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 44 + }, + "from_atom": { + "map_num": 39 + }, + "to_atom": { + "map_num": 40 + } + }, + "restored_smiles": "C=C1C2=CC=C1C(N=Nc1ccc(Nc3ccccc3)c3c(S(=O)(=O)O)cccc13)=CC=C2N=Nc1cccc(S(=O)(=O)O)c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000036", + "op_type": "change_atom_element", + "image_path": "images/000036.png", + "wrong_smiles_mapped": "[NH2:1][NH:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000040", + "op_type": "remove_bond", + "image_path": "images/000040.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[c:7]2[cH:8][cH:9][cH:10][c:11]1-2", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 11}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 11 + } + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000033", + "op_type": "add_bond", + "image_path": "images/000033.png", + "wrong_smiles_mapped": "[O:1]=[S:2]([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1.[OH2:3]", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000041", + "op_type": "add_bond", + "image_path": "images/000041.png", + "wrong_smiles_mapped": "[CH3:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH3:2]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000032", + "op_type": "remove_bond", + "image_path": "images/000032.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]3[c:39]4[cH:40][cH:41][cH:42][c:43]([c:44]24)-[c:37]2[cH:36][cH:35][c:30]([S:31](=[O:32])(=[O:33])[OH:34])[c:29]4[c:21]([NH:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:20][cH:19][c:18]([c:38]42)[N:17]=[N:16]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "29 and 37.\nSo the right part is a naphthalene ring:\nRing 1: 37-36-35-30-29-38-37\nRing 2: 29-21-20-19-18-38-29\nThis is a naphthalene ring.\nSubstituents on right naphthalene:\nAt 30: SO3H\nAt 21: NHPh\nAt 18: N=N\nLet's check the relative positions.\n38 is the bridgehead between 37 and 18.\n29 is the bridgehead between 30 and 21.\nSo 37, 36, ", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000044", + "op_type": "change_atom_element", + "image_path": "images/000044.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][P:9](=[O:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 8}, \"element\": \"S\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 8 + }, + "element": "S", + "charge": 0 + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000047", + "op_type": "change_charge", + "image_path": "images/000047.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[OH+:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000042", + "op_type": "remove_functional_group", + "image_path": "images/000042.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[Cl:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 12}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000046", + "op_type": "add_atom", + "image_path": "images/000046.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9](=[O:10])[OH:11]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 9}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 9 + }, + "group": "OH" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000043", + "op_type": "add_functional_group", + "image_path": "images/000043.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"NH2\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "NH2" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000051", + "op_type": "remove_functional_group", + "image_path": "images/000051.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[F:13]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000045", + "op_type": "remove_atom", + "image_path": "images/000045.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[OH:13]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000049", + "op_type": "remove_bond", + "image_path": "images/000049.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[O:12]1", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 12}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 12 + } + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000048", + "op_type": "change_bond_order", + "image_path": "images/000048.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9]([OH:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 9}, \"atom2\": {\"map_num\": 12}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 9 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000050", + "op_type": "add_bond", + "image_path": "images/000050.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12].[NH2:1][CH3:2]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000039", + "op_type": "change_bond_order", + "image_path": "images/000039.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[SH:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000059", + "op_type": "change_atom_element", + "image_path": "images/000059.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][SH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 17}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 17 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000053", + "op_type": "change_atom_element", + "image_path": "images/000053.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][N:5]=[N:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"C\"}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "C" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000052", + "op_type": "add_functional_group", + "image_path": "images/000052.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][S:7][P:8](=[O:9])([OH:10])[OH:11]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"N\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeAtom): Explicit valence for atom # 0 N, 4, is greater than permitted" + }, + { + "id": "000056", + "op_type": "change_bond_order", + "image_path": "images/000056.png", + "wrong_smiles_mapped": "[C:1]1=[CH:2][NH:3][CH2:4][N:5]=[C:6]=1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 6}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000054", + "op_type": "remove_atom", + "image_path": "images/000054.png", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([NH2:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"NH2\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "NH2" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000060", + "op_type": "remove_atom", + "image_path": "images/000060.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[NH2:25]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000058", + "op_type": "remove_functional_group", + "image_path": "images/000058.png", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([CH3:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000055", + "op_type": "change_charge", + "image_path": "images/000055.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][NH+:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000062", + "op_type": "change_charge", + "image_path": "images/000062.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH+:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 11}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 11 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000057", + "op_type": "remove_bond", + "image_path": "images/000057.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH:4]2[N:5]=[C:6]12", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 6}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000061", + "op_type": "add_atom", + "image_path": "images/000061.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 16}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 16 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000063", + "op_type": "change_bond_order", + "image_path": "images/000063.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000064", + "op_type": "remove_bond", + "image_path": "images/000064.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]2[cH:14][c:15]([CH2:16][OH:17])[c:18]1[c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]2", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 18}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 18 + } + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000067", + "op_type": "add_functional_group", + "image_path": "images/000067.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 16}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 16 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000065", + "op_type": "add_bond", + "image_path": "images/000065.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH2:20])[cH:24]1.[CH:21]([CH3:22])=[O:23]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 20}, \"atom2\": {\"map_num\": 21}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 20 + }, + "atom2": { + "map_num": 21 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000066", + "op_type": "remove_functional_group", + "image_path": "images/000066.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[OH:25]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000070", + "op_type": "remove_atom", + "image_path": "images/000070.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH:7]([OH:30])[CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 30}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 30 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000073", + "op_type": "change_bond_order", + "image_path": "images/000073.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000068", + "op_type": "move_substituent", + "image_path": "images/000068.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][cH:15][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]1[CH2:16][OH:17]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 16}, \"from_atom\": {\"map_num\": 24}, \"to_atom\": {\"map_num\": 15}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 16 + }, + "from_atom": { + "map_num": 24 + }, + "to_atom": { + "map_num": 15 + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000069", + "op_type": "change_atom_element", + "image_path": "images/000069.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][O:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 11}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 11 + }, + "element": "C" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000071", + "op_type": "add_atom", + "image_path": "images/000071.png", + "wrong_smiles_mapped": "[CH2:1]([CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[C:11](=[O:12])[NH:13][CH2:14][N:15]2[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000075", + "op_type": "add_bond", + "image_path": "images/000075.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[O:1]=[CH:2][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000076", + "op_type": "remove_functional_group", + "image_path": "images/000076.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:30])[cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 30}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 30 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000074", + "op_type": "remove_bond", + "image_path": "images/000074.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][C:9]3([CH:10]1[CH2:11]2)[C:12](=[O:13])[NH:14][CH2:15][N:16]3[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 10}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 10 + } + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000078", + "op_type": "move_substituent", + "image_path": "images/000078.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][c:25]([F:27])[cH:26][cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 27}, \"from_atom\": {\"map_num\": 25}, \"to_atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 27 + }, + "from_atom": { + "map_num": 25 + }, + "to_atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000072", + "op_type": "change_charge", + "image_path": "images/000072.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][NH+:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000077", + "op_type": "add_functional_group", + "image_path": "images/000077.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 26}, \"group\": \"F\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 26 + }, + "group": "F" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000080", + "op_type": "remove_atom", + "image_path": "images/000080.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH:22]([OH:31])[O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000079", + "op_type": "change_atom_element", + "image_path": "images/000079.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][S:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 23}, \"element\": \"O\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 23 + }, + "element": "O" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000081", + "op_type": "add_atom", + "image_path": "images/000081.png", + "wrong_smiles_mapped": "[OH:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([O:7][CH3:8])[c:9]1[O:10][CH3:11])-[c:12]1[cH:13][c:14]3[c:15]([cH:16][c:17]1[C:18](=[O:19])[CH:20]1[CH2:21][O:22][C:23](=[O:24])[CH:25]1[CH2:26]2)[O:27][CH2:28][O:29]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000088", + "op_type": "change_atom_element", + "image_path": "images/000088.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([NH:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 18}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 18 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000089", + "op_type": "remove_atom", + "image_path": "images/000089.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH:27]([CH3:31])[CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000091", + "op_type": "change_charge", + "image_path": "images/000091.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[NH+:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 14}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000090", + "op_type": "add_atom", + "image_path": "images/000090.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000084", + "op_type": "remove_bond", + "image_path": "images/000084.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([c:17]4[c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[C:26]41[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "[CH2:27]2`\nC26 has ring closures 4 and 1.\n4 connects to c17.\n1 connects to CH21.\nIt is also bonded to C24 and CH2:27.\nSo C26 is bonded to: c17, CH21, C24, CH2:27.\nLet's check CH21:\n`[CH:21]1` -> bonded to C19, CH2:22, and C26 (via ring closure 1).\nSo CH21 is bonded to C19, CH2:22, C26.\nLet's check the image again.\nIn the image, the", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000092", + "op_type": "change_bond_order", + "image_path": "images/000092.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH:15]=[CH:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 15}, \"atom2\": {\"map_num\": 16}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 15 + }, + "atom2": { + "map_num": 16 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000086", + "op_type": "remove_functional_group", + "image_path": "images/000086.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:21]1([NH2:31])[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000082", + "op_type": "change_charge", + "image_path": "images/000082.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[OH+:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 25}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 25 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000083", + "op_type": "change_bond_order", + "image_path": "images/000083.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[CH:19]([OH:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 19}, \"atom2\": {\"map_num\": 20}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 19 + }, + "atom2": { + "map_num": 20 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000085", + "op_type": "add_bond", + "image_path": "images/000085.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3.[OH:8][CH3:9]", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 8}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 8 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000087", + "op_type": "move_substituent", + "image_path": "images/000087.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:26]1([CH2:21][CH2:22][O:23][C:24]1=[O:25])[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 27}, \"from_atom\": {\"map_num\": 26}, \"to_atom\": {\"map_num\": 24}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 27 + }, + "from_atom": { + "map_num": 26 + }, + "to_atom": { + "map_num": 24 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 24 C, 5, is greater than permitted" + }, + { + "id": "000098", + "op_type": "change_atom_element", + "image_path": "images/000098.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[S:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 9 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000094", + "op_type": "add_bond", + "image_path": "images/000094.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1.[cH:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\n \"type\": \"AddBond\",\n \"bond\": {\n \"atom1\": {\n \"map_num\": 6\n },\n \"atom2\": {\n \"map_num\": 7\n }\n },\n \"order\": \"SINGLE\"\n}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000097", + "op_type": "move_substituent", + "image_path": "images/000097.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:9]2[cH:8][cH:7][cH:13][cH:12][c:10]2[F:11])[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 13 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000095", + "op_type": "remove_functional_group", + "image_path": "images/000095.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)([N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[CH3:31])[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000096", + "op_type": "add_functional_group", + "image_path": "images/000096.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000093", + "op_type": "remove_bond", + "image_path": "images/000093.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]2[cH:29][c:30]1[CH:16]1[CH2:15][N:14]([CH:6]2[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[CH2:28][CH2:27][N:17]1[CH2:18][CH:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 30}, \"atom2\": {\"map_num\": 16}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 30 + }, + "atom2": { + "map_num": 16 + } + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000101", + "op_type": "change_charge", + "image_path": "images/000101.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][OH+:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000104", + "op_type": "add_bond", + "image_path": "images/000104.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4](=[O:5])[O:6][CH2:7][CH3:8].[OH:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 9}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 9 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000100", + "op_type": "add_atom", + "image_path": "images/000100.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4]([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 4}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 4 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000102", + "op_type": "change_bond_order", + "image_path": "images/000102.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4]([OH:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 5}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000105", + "op_type": "remove_functional_group", + "image_path": "images/000105.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][c:15]([Cl:25])[cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000099", + "op_type": "remove_atom", + "image_path": "images/000099.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH2:8][CH3:25])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000106", + "op_type": "add_functional_group", + "image_path": "images/000106.png", + "wrong_smiles_mapped": "[CH3:1][O:2][P:3](=[O:4])([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000103", + "op_type": "remove_bond", + "image_path": "images/000103.png", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]2[C:11](=[O:12])[c:13]3[c:14]1[cH:15][cH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([c:22]31)[C:23]2=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 14}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 14 + } + } + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000112", + "op_type": "change_charge", + "image_path": "images/000112.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[OH+:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 26}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 26 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000109", + "op_type": "change_atom_element", + "image_path": "images/000109.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000108", + "op_type": "swap_substituents", + "image_path": "images/000108.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][C:22]1=[C:13]2[C:11](=[O:12])[N:10]3[C:17](=[CH:16][CH:15]=[CH:14]2)[CH:18]=[CH:19][CH:20]=[C:21]1[C:23]3=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": ")`\n`[N:10]3`\n`[C:17](=[CH:16][CH:15]=[CH:14]2)`\n`[CH:18]=[CH:19][CH:20]=[C:21]1`\n`[C:23]3=[O:24]`\nLet's re-evaluate the connections.\n`[C:17]` is bonded to `[CH:16]` (double).\n`[CH:16]` is bonded to `[CH:15]` (single).\n`[CH:15]` is bonded to `[CH:14]` (double).\n`[CH:14]` is bonded to `[C", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000116", + "op_type": "remove_functional_group", + "image_path": "images/000116.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[Br:57]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 57}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 57 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000113", + "op_type": "change_bond_order", + "image_path": "images/000113.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 16}, \"atom2\": {\"map_num\": 17}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 16 + }, + "atom2": { + "map_num": 17 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000107", + "op_type": "move_substituent", + "image_path": "images/000107.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][n:10]1[c:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][c:17]([cH:22]2)[CH:18]=[CH:19][CH:20]=[c:21]3[c:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 15}, \"atom2\": {\"map_num\": 21}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 15 + }, + "atom2": { + "map_num": 21 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCOP(=O)(OCC)On1c(=O)c2c3cc(cc(c3)c1=O)C=CC=2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000110", + "op_type": "remove_atom", + "image_path": "images/000110.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[C:35]([OH:36])([CH3:57])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 57}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 57 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000111", + "op_type": "add_atom", + "image_path": "images/000111.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][SH:29](=[O:30])=[O:31])[CH:32]([OH:33])[CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 29}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 29 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000114", + "op_type": "remove_bond", + "image_path": "images/000114.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 8}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000115", + "op_type": "add_bond", + "image_path": "images/000115.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 17}, \"atom2\": {\"map_num\": 18}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 17 + }, + "atom2": { + "map_num": 18 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000121", + "op_type": "remove_atom", + "image_path": "images/000121.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[CH3:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 7}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000120", + "op_type": "change_atom_element", + "image_path": "images/000120.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[N:4]([OH:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000117", + "op_type": "add_functional_group", + "image_path": "images/000117.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH2:33][CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 33}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 33 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000124", + "op_type": "change_bond_order", + "image_path": "images/000124.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([OH:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000126", + "op_type": "add_bond", + "image_path": "images/000126.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][N:4]([CH3:5])[NH2:6].[OH2:3]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000125", + "op_type": "remove_bond", + "image_path": "images/000125.png", + "wrong_smiles_mapped": "[CH2:1]1[C:2](=[O:3])[N:4]([NH2:6])[CH2:5]1", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 5}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 5 + } + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000118", + "op_type": "move_substituent", + "image_path": "images/000118.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][C:25]1([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH2:27][CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 28}, \"from_atom\": {\"map_num\": 25}, \"to_atom\": {\"map_num\": 27}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 28 + }, + "from_atom": { + "map_num": 25 + }, + "to_atom": { + "map_num": 27 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000122", + "op_type": "add_atom", + "image_path": "images/000122.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000119", + "op_type": "swap_substituents", + "image_path": "images/000119.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:35]1[CH:33]([OH:34])[CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH:25]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 24}, \"atom2\": {\"map_num\": 36}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 24 + }, + "atom2": { + "map_num": 36 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1C(O)C(O)OC(CS(=O)(=O)O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000127", + "op_type": "remove_functional_group", + "image_path": "images/000127.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[NH2:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 7}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000123", + "op_type": "change_charge", + "image_path": "images/000123.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[OH+:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000128", + "op_type": "add_functional_group", + "image_path": "images/000128.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000130", + "op_type": "remove_atom", + "image_path": "images/000130.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH:6]([NH2:26])[CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000132", + "op_type": "change_charge", + "image_path": "images/000132.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000136", + "op_type": "remove_functional_group", + "image_path": "images/000136.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][C:4]2([F:26])[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000131", + "op_type": "add_atom", + "image_path": "images/000131.png", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][CH:3]2[O:4][CH2:5][CH:6]=[C:7]3[CH2:8][N:9]4[CH2:10][CH2:11][C@:12]56[c:13]7[cH:14][cH:15][cH:16][cH:17][c:18]7[N:19]1[CH:20]5[C@H:21]2[C@H:22]3[CH2:23][C@H:24]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000139", + "op_type": "change_atom_element", + "image_path": "images/000139.png", + "wrong_smiles_mapped": "[F:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000140", + "op_type": "remove_atom", + "image_path": "images/000140.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH3:9]", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000134", + "op_type": "remove_bond", + "image_path": "images/000134.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH:3]2[CH:4]3[O:5][CH2:6][CH:7]=[C:8]4[CH:9]2[N:10]2[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]3[C@H:23]4[CH2:24][C@H:25]26", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 9}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000141", + "op_type": "add_atom", + "image_path": "images/000141.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000142", + "op_type": "remove_bond", + "image_path": "images/000142.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][c:8]1-2", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 8}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000143", + "op_type": "add_bond", + "image_path": "images/000143.png", + "wrong_smiles_mapped": "[F:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000137", + "op_type": "flip_chirality", + "image_path": "images/000137.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 4}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 4 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@@H]2[C@H]3C[C@H]46", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000138", + "op_type": "move_substituent", + "image_path": "images/000138.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:6]2[O:5][CH2:4][C@H:22]3[CH:21]4[C@:13]5([CH2:12][CH2:11][N:10]6[CH2:9][C:8](=[CH:7]2)[C@@H:23]3[CH2:24][C@H:25]65)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]14", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 4}, \"from_atom\": {\"map_num\": 22}, \"to_atom\": {\"map_num\": 7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 4 + }, + "from_atom": { + "map_num": 22 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "O=C1CC2OCC2=C2CN3CC[C@]45c6ccccc6N1C4C[C@H]2C[C@H]35", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000129", + "op_type": "change_atom_element", + "image_path": "images/000129.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[N:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 21}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 21 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000144", + "op_type": "remove_functional_group", + "image_path": "images/000144.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:9])[cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000135", + "op_type": "add_bond", + "image_path": "images/000135.png", + "wrong_smiles_mapped": "[CH2:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46.[OH2:1]", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 1}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 1 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000145", + "op_type": "add_functional_group", + "image_path": "images/000145.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000146", + "op_type": "change_atom_element", + "image_path": "images/000146.png", + "wrong_smiles_mapped": "[Cl:1][O:2][c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000133", + "op_type": "change_bond_order", + "image_path": "images/000133.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH2:7][CH:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\n \"type\": \"ChangeBond\",\n \"bond\": {\n \"atom1\": {\n \"map_num\": 7\n },\n \"atom2\": {\n \"map_num\": 8\n }\n },\n \"order\": \"DOUBLE\"\n}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 8 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000151", + "op_type": "remove_functional_group", + "image_path": "images/000151.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Br:9]", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000152", + "op_type": "add_functional_group", + "image_path": "images/000152.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"Cl\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "Cl", + "bond_order": "SINGLE" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000148", + "op_type": "add_atom", + "image_path": "images/000148.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"Cl\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "Cl", + "bond_order": "SINGLE" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000147", + "op_type": "remove_atom", + "image_path": "images/000147.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH3:9]", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000153", + "op_type": "move_substituent", + "image_path": "images/000153.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:6]1[cH:5][cH:4][cH:3][cH:8][n:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 2}, \"from_atom\": {\"map_num\": 6}, \"to_atom\": {\"map_num\": 5}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 2 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 5 + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000150", + "op_type": "add_bond", + "image_path": "images/000150.png", + "wrong_smiles_mapped": "[Cl:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000149", + "op_type": "remove_bond", + "image_path": "images/000149.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]1-2", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\n \"type\": \"RemoveBond\",\n \"bond\": {\n \"atom1\": {\n \"map_num\": 5\n },\n \"atom2\": {\n \"map_num\": 8\n }\n }\n}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000158", + "op_type": "add_bond", + "image_path": "images/000158.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\n \"type\": \"AddBond\",\n \"bond\": {\n \"atom1\": {\n \"map_num\": 1\n },\n \"atom2\": {\n \"map_num\": 2\n }\n },\n \"order\": \"SINGLE\"\n}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000156", + "op_type": "add_atom", + "image_path": "images/000156.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 7 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000154", + "op_type": "change_atom_element", + "image_path": "images/000154.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000155", + "op_type": "remove_atom", + "image_path": "images/000155.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([CH3:14])[cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000159", + "op_type": "remove_functional_group", + "image_path": "images/000159.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]([Cl:14])[c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000165", + "op_type": "change_charge", + "image_path": "images/000165.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[OH+:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000164", + "op_type": "add_atom", + "image_path": "images/000164.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[CH:4][CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 4}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 4 + }, + "group": "CH3" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000157", + "op_type": "remove_bond", + "image_path": "images/000157.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[cH:7][c:8]-3[c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 8}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000160", + "op_type": "add_functional_group", + "image_path": "images/000160.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 7 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000162", + "op_type": "change_atom_element", + "image_path": "images/000162.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000166", + "op_type": "change_bond_order", + "image_path": "images/000166.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000163", + "op_type": "remove_atom", + "image_path": "images/000163.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[CH3:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 8 + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000168", + "op_type": "add_bond", + "image_path": "images/000168.png", + "wrong_smiles_mapped": "[CH2:3]=[C:4]([CH3:5])[CH:6]=[O:7].[CH3:1][CH3:2]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000167", + "op_type": "remove_bond", + "image_path": "images/000167.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]1[CH:3]=[C:4]([CH3:5])[C:6]1=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 6}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000169", + "op_type": "remove_functional_group", + "image_path": "images/000169.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[Br:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 8 + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000161", + "op_type": "move_substituent", + "image_path": "images/000161.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[C:12]([CH3:13])[c:11]2[cH:5][cH:6][cH:7][c:8]([c:9]2[CH3:10])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 4}, \"from_atom\": {\"map_num\": 8}, \"to_atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 4 + }, + "from_atom": { + "map_num": 8 + }, + "to_atom": { + "map_num": 9 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 9 C, 5, is greater than permitted" + }, + { + "id": "000170", + "op_type": "add_functional_group", + "image_path": "images/000170.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]=[C:3]([CH3:4])[CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000174", + "op_type": "change_charge", + "image_path": "images/000174.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[OH+:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 9 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000173", + "op_type": "add_atom", + "image_path": "images/000173.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000171", + "op_type": "change_atom_element", + "image_path": "images/000171.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeGroup\", \"atom\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "ChangeGroup", + "atom": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Unknown action type: 'ChangeGroup'. Valid types: ['AddAtom', 'AddBond', 'AddGroup', 'ChangeAtom', 'ChangeBond', 'FlipChirality', 'MoveSubstituent', 'RemoveAtom', 'RemoveBond', 'RemoveGroup', 'SwapSubstituents', 'FlipEZ', 'Batch']" + }, + { + "id": "000172", + "op_type": "remove_atom", + "image_path": "images/000172.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[NH2:13])[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"NH2\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "NH2" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000176", + "op_type": "add_bond", + "image_path": "images/000176.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][NH:12]2.[OH2:11]", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 10}, \"atom2\": {\"map_num\": 11}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000177", + "op_type": "remove_functional_group", + "image_path": "images/000177.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[c:3]([Cl:13])[cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000183", + "op_type": "change_charge", + "image_path": "images/000183.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[NH+:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000179", + "op_type": "move_substituent", + "image_path": "images/000179.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:7][N:12]2[C:5](=[CH:6][C:8](=[O:9])[C:10]2=[O:11])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"N\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "N" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeAtom): Explicit valence for atom # 5 N, 4, is greater than permitted" + }, + { + "id": "000182", + "op_type": "add_atom", + "image_path": "images/000182.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH3:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 12}, \"element\": \"O\", \"bond_order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 12 + }, + "element": "O", + "bond_order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000181", + "op_type": "change_atom_element", + "image_path": "images/000181.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][SH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "C" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000178", + "op_type": "add_functional_group", + "image_path": "images/000178.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": " to (1, -0.5)? Yes, up-right.\nLet me re-read the image.\nIs there a vertical bond on the left?\nLooking at the image, the leftmost part of the benzene ring is a VERTEX, not a vertical edge.\nWait, if the leftmost part is a vertex, then the top and bottom edges must be horizontal.\nLet's check if top and bottom edges are horizontal.\nTop edge: from top fused carbon, goes left (horizontal).\nBottom edge: from bottom fused carbon, goes left (horizontal).\nLet's check the image.\nYes! The top edge of the benzene ring is horizontal.\nThe bottom edge of the benzene ring is horizontal.\nSo the vertices are:\nTop", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000184", + "op_type": "change_bond_order", + "image_path": "images/000184.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][C:6]2=[C:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000175", + "op_type": "change_bond_order", + "image_path": "images/000175.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH:10]([OH:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "C" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(O)N2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000180", + "op_type": "swap_substituents", + "image_path": "images/000180.png", + "wrong_smiles_mapped": "[CH3:1][c:5]1[cH:4][cH:3][c:2]2[cH:7][c:6]1[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 1}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 4}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 1 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 4 + } + }, + "restored_smiles": "Cc1cc2cc(c1)C(=O)C(=O)N2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000185", + "op_type": "remove_bond", + "image_path": "images/000185.png", + "wrong_smiles_mapped": "[CH3:1][N:2]1[CH2:3][C:9]2([OH:10])[CH:7]([OH:8])[CH:6]3[N:5]=[C:4]1[O:15][CH:14]3[CH:11]2[CH2:12][OH:13]", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "C" + }, + "restored_smiles": "CN1CC2(O)C(O)C3N=C1OC3C2CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000190", + "op_type": "change_charge", + "image_path": "images/000190.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000191", + "op_type": "change_bond_order", + "image_path": "images/000191.png", + "wrong_smiles_mapped": "[OH:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000186", + "op_type": "add_bond", + "image_path": "images/000186.png", + "wrong_smiles_mapped": "[CH3:12][OH:13].[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 11}, \"atom2\": {\"map_num\": 12}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000188", + "op_type": "move_substituent", + "image_path": "images/000188.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][C:14]2([CH2:12][OH:13])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 12}, \"from_atom\": {\"map_num\": 14}, \"to_atom\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 12 + }, + "from_atom": { + "map_num": 14 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000187", + "op_type": "add_functional_group", + "image_path": "images/000187.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH2:7][CH:8]([OH:9])[CH:10]([CH2:11][OH:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\": \"ChangeGroup\", \"anchor\": {\"map_num\": 10}, \"group\": \"OH\"}", + "predicted_action": { + "type": "ChangeGroup", + "anchor": { + "map_num": 10 + }, + "group": "OH" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Unknown action type: 'ChangeGroup'. Valid types: ['AddAtom', 'AddBond', 'AddGroup', 'ChangeAtom', 'ChangeBond', 'FlipChirality', 'MoveSubstituent', 'RemoveAtom', 'RemoveBond', 'RemoveGroup', 'SwapSubstituents', 'FlipEZ', 'Batch']" + }, + { + "id": "000192", + "op_type": "add_functional_group", + "image_path": "images/000192.png", + "wrong_smiles_mapped": "[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]1[OH:12]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 2}, \"element\": \"O\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 2 + }, + "element": "O", + "bond_order": "SINGLE" + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000195", + "op_type": "add_functional_group", + "image_path": "images/000195.png", + "wrong_smiles_mapped": "[cH:1]1[n:2][c:3]([Cl:4])[n:5][c:6]([C:7]([Cl:8])([Cl:9])[Cl:10])[n:11]1", + "correct_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"Cl\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "Cl", + "bond_order": "SINGLE" + }, + "restored_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000194", + "op_type": "swap_substituents", + "image_path": "images/000194.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:13])[c:12]1[C:9](=[O:10])[OH:11]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 12}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 12 + } + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000197", + "op_type": "change_bond_order", + "image_path": "images/000197.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]=[CH:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000193", + "op_type": "move_substituent", + "image_path": "images/000193.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[c:5]([C:9](=[O:10])[OH:11])[cH:6][cH:7][cH:8][c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000200", + "op_type": "change_charge", + "image_path": "images/000200.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[OH+:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 43}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 43 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000199", + "op_type": "move_substituent", + "image_path": "images/000199.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][c:15]([Cl:14])[cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 14}, \"from_atom\": {\"map_num\": 15}, \"to_atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 15 + }, + "to_atom": { + "map_num": 13 + } + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000196", + "op_type": "change_charge", + "image_path": "images/000196.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[OH+:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000198", + "op_type": "add_functional_group", + "image_path": "images/000198.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "NCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000204", + "op_type": "change_charge", + "image_path": "images/000204.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][C:4](=[OH+:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "```json\n{\n \"type\": \"ChangeAtom\",\n \"atom\": {\n \"map_num\": 5\n },\n \"element\": \"O\",\n \"charge\": 0\n}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000189", + "op_type": "swap_substituents", + "image_path": "images/000189.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[CH:14]1[CH:6]2[N:5]=[C:4]([CH:11]([CH2:12][OH:13])[CH:9]([OH:10])[CH:7]2[OH:8])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 11 + } + }, + "restored_smiles": "CC(C)C1OC2=NC1C(O)C(O)N2CO", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000202", + "op_type": "move_substituent", + "image_path": "images/000202.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:26]2([O:27][C:28]([CH3:29])=[O:30])[CH:25]=[C:24]3[CH:23]([CH:32]1[CH2:31]2)[CH:39]([O:40][C:41]([CH3:42])=[O:43])[O:38][CH:33]3[O:34][C:35]([CH3:36])=[O:37]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 12}, \"atom2\": {\"map_num\": 26}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 12 + }, + "atom2": { + "map_num": 26 + } + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC2(OC(C)=O)C=C3C(OC(C)=O)OC(OC(C)=O)C3C1CC2OC(=O)c1ccc(O)cc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000201", + "op_type": "change_bond_order", + "image_path": "images/000201.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][CH:41]([CH3:42])[OH:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "C:23]`.\nAnd `[CH:33]` is attached to `[O:38]`.\n`[O:38]` is attached to `[CH:39]`.\n`[CH:39]` is attached to `[C:23]`.\nThis forms an oxetane: C23 - CH(OAc) - O - CH - C23.\nWait, the SMILES has `[CH:39]` attached to `[O:40][CH:41]([CH3:42])[OH:43]`.\nLet's look at the image.\nIs there an oxetane?\nNo, the image shows a 5-membered ring", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000203", + "op_type": "swap_substituents", + "image_path": "images/000203.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:23]1([CH3:8])[CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[CH2:11][CH:9]([CH3:10])[C:7]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]21)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[O:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 24}, \"atom2\": {\"map_num\": 33}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 24 + }, + "atom2": { + "map_num": 33 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 23 C, 5, is greater than permitted" + }, + { + "id": "000207", + "op_type": "change_charge", + "image_path": "images/000207.png", + "wrong_smiles_mapped": "[CH3:1][OH+:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000205", + "op_type": "change_bond_order", + "image_path": "images/000205.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][CH:4]([OH:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 5}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000206", + "op_type": "move_substituent", + "image_path": "images/000206.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[N:3]([Br:9])[C:4](=[O:5])[C:6]([Br:7])=[CH:8]1", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 3}, \"to_atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 3 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000210", + "op_type": "swap_substituents", + "image_path": "images/000210.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:13]1[c:7]([CH3:14])[cH:8][cH:9][c:10]([Cl:11])[cH:12]1", + "correct_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 9 + } + }, + "restored_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000209", + "op_type": "swap_substituents", + "image_path": "images/000209.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:6]1[c:5](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[n:35](-[c:36]2[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]2)[c:33](=[O:34])[c:32]2[c:19]1[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][n:30]1)[cH:31]2", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 6 + } + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000212", + "op_type": "swap_substituents", + "image_path": "images/000212.png", + "wrong_smiles_mapped": "[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([CH2:10][CH2:11][Cl:12])[n:7][cH:8][n:9]2[n:13]([CH3:14])[c:15]1=[O:16]", + "correct_smiles": "Cn1c(=O)c2c(ncn2CCCl)n(C)c1=O", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 10}, \"from_atom\": {\"map_num\": 6}, \"to_atom\": {\"map_num\": 7}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 9 N, 4, is greater than permitted" + }, + { + "id": "000211", + "op_type": "swap_substituents", + "image_path": "images/000211.png", + "wrong_smiles_mapped": "[CH3:1][NH:2][C:3](=[O:4])[CH:26]1[CH:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([NH2:19])[cH:20][cH:21]4)[n:22][cH:23][n:24][c:25]23)[O:6][CH:5]([OH:27])[CH:28]1[OH:29]", + "correct_smiles": "CNC(=O)C1OC(n2cnc3c(NCc4ccc(N)cc4)ncnc32)C(O)C1O", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 27}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 27 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (SwapSubstituents): Explicit valence for atom # 26 O, 4, is greater than permitted" + }, + { + "id": "000208", + "op_type": "move_substituent", + "image_path": "images/000208.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:18]2[O:16][CH3:17])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 16}, \"from_atom\": {\"map_num\": 18}, \"to_atom\": {\"map_num\": 15}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 16 + }, + "from_atom": { + "map_num": 18 + }, + "to_atom": { + "map_num": 15 + } + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000214", + "op_type": "swap_substituents", + "image_path": "images/000214.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([Cl:3])[c:6]1[cH:5][c:4]([Cl:7])[c:10]([Cl:11])[cH:9][cH:8]1", + "correct_smiles": "O=C(Cl)c1cc(Cl)ccc1Cl", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 2}, \"from_atom\": {\"map_num\": 6}, \"to_atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 2 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 9 + } + }, + "restored_smiles": "O=C(Cl)c1cccc(Cl)c1Cl", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000213", + "op_type": "swap_substituents", + "image_path": "images/000213.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[n:3][cH:4][c:5]([CH2:6][c:26]2[n+:7]([CH3:27])[cH:8][s:9][c:10]2[CH2:11][CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:18](=[O:19])([OH:20])[O:21][P:22](=[O:23])([O-:24])[OH:25])[c:28]([NH2:29])[n:30]1", + "correct_smiles": "Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)c2C)c(N)n1", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 26 + } + }, + "restored_smiles": "Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)c2C)c(N)n1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000215", + "op_type": "swap_substituents", + "image_path": "images/000215.png", + "wrong_smiles_mapped": "[CH3:1][C:8]12[C:2]([CH3:9])([CH3:10])[CH:3]=[CH:4][CH:5]1[CH2:6][CH2:7]2", + "correct_smiles": "CC12C=CC(CC1)C2(C)C", + "predicted_raw": "[CH2:7]2`\nWait, the wrong SMILES has:\nC8 connected to C1(Me), C2, C5, C7.\nC2 connected to C8, C9(Me), C10(Me), C3.\nC3 connected to C2, C4.\nC4 connected to C3, C5.\nC5 connected to C4, C8, C6.\nC6 connected to C5, C7.\nC7 connected to C6, C8.\nLet's draw this wrong SMILES:\nC8 is a bridgehead. C5 is a bridgehead.\nPath 1 between C8 and C5: C8 - C2 - C3 =", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000216", + "op_type": "swap_substituents", + "image_path": "images/000216.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[S:5])([O:6][CH2:7][CH3:8])[O:9][c:12]1[cH:11][c:10]([CH3:13])[n:15][nH:14]1", + "correct_smiles": "CCOP(=S)(OCC)Oc1cc(C)[nH]n1", + "predicted_raw": "{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 14}, \"atom2\": {\"map_num\": 15}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 14 + }, + "atom2": { + "map_num": 15 + } + }, + "restored_smiles": "CCOP(=S)(OCC)Oc1cc(C)n[nH]1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000219", + "op_type": "swap_substituents", + "image_path": "images/000219.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([F:18])[cH:16][c:17]1[N:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1", + "correct_smiles": "CN(C)c1ccc(N=Nc2ccccc2)cc1F", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 18}, \"atom2\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 18 + }, + "atom2": { + "map_num": 8 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (SwapSubstituents): Explicit valence for atom # 7 F, 3, is greater than permitted" + }, + { + "id": "000217", + "op_type": "flip_chirality", + "image_path": "images/000217.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@@H:5]([OH:6])[CH2:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[C:13](=[O:14])[CH2:15][C@@:16]2([CH3:17])[C@H:18]1[CH2:19][CH2:20][C@@:21]2([OH:22])[C:23](=[O:24])[CH2:25][OH:26]", + "correct_smiles": "C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@@]2(O)C(=O)CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000218", + "op_type": "swap_substituents", + "image_path": "images/000218.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[c:11]([CH2:12][CH2:13][N:14]([CH3:15])[CH3:16])[cH:17][c:18]3[c:19]([c:20]2[O:21][CH3:22])[O:23][CH2:24][O:25]3)[c:26]([O:31][CH3:32])[c:30]1[C:27](=[O:28])[OH:29]", + "correct_smiles": "COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(C(=O)O)c1OC", + "predicted_raw": "cH:5][c:6]([C:7](=[O:8])...)[c:26]([O:31][CH3:32])[c:30]1[C:27](=[O:28])[OH:29]`\nWait, `[c:6](...)[c:26](...)[c:30]1`\nThis means c6 is connected to c26, and c26 is connected to c30.\nSo c6 and c30 are separated by c26.\nIf the image has them ortho, then the wrong SMILES has the wrong connectivity or I am misinterpreting the image.\nLet's re-examine the image.\nMaybe", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000220", + "op_type": "swap_substituents", + "image_path": "images/000220.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([F:13])[c:9]([OH:10])[cH:11][c:12]1[OH:8]", + "correct_smiles": "NCC(O)c1cc(O)c(O)cc1F", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 13}, \"from_atom\": {\"map_num\": 7}, \"to_atom\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 13 + }, + "from_atom": { + "map_num": 7 + }, + "to_atom": { + "map_num": 6 + } + }, + "restored_smiles": "NCC(O)c1c(O)cc(O)cc1F", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000221", + "op_type": "swap_substituents", + "image_path": "images/000221.png", + "wrong_smiles_mapped": "[NH2:1][C:2]1=[N:3][CH:4]=[CH:5][c:9]2[cH:8][cH:7][c:6]([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]4[cH:20][c:21]5[n:22][cH:23][cH:24][cH:25][c:26]5[s:27]4)[C:28]3=[O:29])[c:31]1[cH:30]2", + "correct_smiles": "Nc1nccc2ccc(CN3CCC(NS(=O)(=O)c4cc5ncccc5s4)C3=O)cc12", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 22}, \"element\": \"C\"}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 22 + }, + "element": "C" + }, + "restored_smiles": "NC1=NC=Cc2ccc(CN3CCC(NS(=O)(=O)c4cc5ccccc5s4)C3=O)c1c2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000223", + "op_type": "flip_chirality", + "image_path": "images/000223.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[C:11]1=[C:12]([CH2:13][C@H:14]([CH3:15])[O:16][C@H:17]1[CH3:18])[C:19]2=[O:20]", + "correct_smiles": "COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C2=O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "COc1cccc2c1C(=O)C1=C(C[C@@H](C)O[C@H]1C)C2=O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000224", + "op_type": "flip_chirality", + "image_path": "images/000224.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][n:7][c:8]2[c:9]1[n:10][cH:11][n:12]2[C@@H:13]1[O:14][C@@H:15]([CH2:16][OH:17])[C@@H:18]([O:19][P:20](=[O:21])([OH:22])[OH:23])[C@H:24]1[OH:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1", + "correct_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O)c1cccnc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 19}, \"from_atom\": {\"map_num\": 18}, \"to_atom\": {\"map_num\": 24}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 19 + }, + "from_atom": { + "map_num": 18 + }, + "to_atom": { + "map_num": 24 + } + }, + "restored_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO)C[C@]1(O)OP(=O)(O)O)c1cccnc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000222", + "op_type": "flip_chirality", + "image_path": "images/000222.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([c:18]3[cH:19][cH:20][c:21](=[O:22])[o:23][cH:24]3)[CH2:25][CH2:26][C@:27]12[OH:28]", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 17}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 17 + } + }, + "restored_smiles": "C[C@]12CC[C@H](O)C[C@@H]1CCC1C2CC[C@]2(C)[C@H](c3ccc(=O)oc3)CC[C@]12O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000227", + "op_type": "flip_chirality", + "image_path": "images/000227.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[NH:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15]", + "correct_smiles": "CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 6 + } + }, + "restored_smiles": "CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000226", + "op_type": "flip_chirality", + "image_path": "images/000226.png", + "wrong_smiles_mapped": "[CH2:1]=[C:2]([CH3:3])[C@H:4]1[CH2:5][c:6]2[c:7]([cH:8][cH:9][c:10]3[c:11]2[O:12][C@H:13]2[CH2:14][O:15][c:16]4[cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24][c:25]4[C@@H:26]2[C:27]3=[O:28])[O:29]1", + "correct_smiles": "C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 26 + } + }, + "restored_smiles": "C=C(C)[C@H]1Cc2c(ccc3c2O[C@H]2COc4cc(OC)c(OC)cc4[C@H]2C3=O)O1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000225", + "op_type": "flip_chirality", + "image_path": "images/000225.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:8][CH2:9][CH:10]1[CH:11]2[CH2:12][CH2:13][C:14]2([CH3:15])[CH:16]1[CH2:17][CH2:18][C@H:19]2[OH:20]", + "correct_smiles": "CC12CCCC[C@@H]1CCC1C2CCC2(C)C1CC[C@@H]2O", + "predicted_raw": "Left-down from C_BL to a CH2.\nUp-left from that CH2 to the CH-OH.\nThis is the 5-membered ring.\nNow from C_TL, a bond goes right to a CH. Let's call it C_M1.\nFrom C_BL, a bond goes right to a CH2, then right to a CH. Let's call this CH C_M2.\nAre C_M1 and C_M2 connected?\nIf they are connected, the middle ring is C_TL - C_M1 - C_M2 - CH2 - C_BL. That's 5 atoms.\nBut looking at the image, C_M1 and C_M2 are connected", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000229", + "op_type": "flip_chirality", + "image_path": "images/000229.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][CH:16]([OH:17])[C@H:18]1[O:19][CH2:20][C@@H:21]([OH:22])[C@H:23]1[OH:24]", + "correct_smiles": "CCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O", + "predicted_raw": " (3)\n\\ (4)\n/ (5)\n\\ (6)\n/ (7)\n\\ (8)\n/ (9)\n\\ (10)\n/ (11)\n\\ (12, C=O)\nLet's count the segments (bonds):\n1-2, 2-3, 3-4, 4-5, 5-6, 6-7, 7-8, 8-9, 9-10, 10-11, 11-12.\nThat's 11 bonds, so 12 carbons.\nWrong SMILES has:\n[CH3:1][CH2:2][CH2:", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000231", + "op_type": "flip_chirality", + "image_path": "images/000231.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C@H:3]1[O:4][C:5](=[O:6])[C@H:7]([CH3:8])[C@@H:9]([O:10][CH:11]2[CH2:12][C:13]([CH3:14])([O:15][CH3:16])[CH:17]([OH:18])[CH:19]([CH3:20])[O:21]2)[CH:22]([CH3:23])[C@@H:24]([O:25][CH:26]2[O:27][CH:28]([CH3:29])[CH2:30][CH:31]([N:32]([CH3:33])[CH3:34])[CH:35]2[OH:36])[C@@:37]([CH3:38])([OH:39])[CH2:40][C@@H:41]([CH3:42])[C:43](=[O:44])[C@H:45]([CH3:46])[C@@H:47]([OH:48])[C@H:49]1[CH3:50]", + "correct_smiles": "CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(C)(OC)C(O)C(C)O2)C(C)[C@@H](OC2OC(C)CC(N(C)C)C2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 18}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 18 + } + }, + "restored_smiles": "CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(C)(OC)CC(C)O2)C(C)[C@@H](OC2OC(C)CC(N(C)C)C2O)[C@@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000228", + "op_type": "flip_chirality", + "image_path": "images/000228.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH:5]3[c:6]4[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[c:13]4[CH2:14][CH2:15][CH:16]3[CH:17]1[CH2:18][CH2:19][C@H:20]2[OH:21]", + "correct_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@@H]2O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 20}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 20 + } + }, + "restored_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@@H]2O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000230", + "op_type": "flip_chirality", + "image_path": "images/000230.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@:5]1([C:6]([CH3:7])=[O:8])[C@H:9]([CH3:10])[CH2:11][C@H:12]2[CH:13]3[CH:14]=[C:15]([Cl:16])[C:17]4=[CH:18][C:19](=[O:20])[CH2:21][CH2:22][C:23]4([CH3:24])[C@@H:25]3[CH2:26][CH2:27][C:28]12[CH3:29]", + "correct_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3C=C(Cl)C4=CC(=O)CCC4(C)[C@H]3CCC21C", + "predicted_raw": "{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 14}, \"atom2\": {\"map_num\": 15}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 14 + }, + "atom2": { + "map_num": 15 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3CC(Cl)C4=CC(=O)CCC4(C)[C@@H]3CCC21C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000233", + "op_type": "flip_chirality", + "image_path": "images/000233.png", + "wrong_smiles_mapped": "[CH3:1][C@@H:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "C[C@H](N)Cc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 2}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 2 + } + }, + "restored_smiles": "C[C@H](N)Cc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000234", + "op_type": "flip_chirality", + "image_path": "images/000234.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@@H:11]1[CH2:12][C@H:13]([OH:14])[C@@H:15]([CH2:16][O:17][P:18](=[O:19])([OH:20])[OH:21])[O:22]1", + "correct_smiles": "Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 11 + } + }, + "restored_smiles": "Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000235", + "op_type": "flip_chirality", + "image_path": "images/000235.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C@@H:3]1[C@@H:4]([O:5][C@@H:6]2[O:7][C@H:8]([CH3:9])[C@@H:10]([O:11][C@H:12]3[CH2:13][C@@:14]([CH3:15])([OH:16])[C@H:17]([O:18][C:19](=[O:20])[CH2:21][CH:22]([CH3:23])[CH3:24])[C@H:25]([CH3:26])[O:27]3)[C@H:28]([N:29]([CH3:30])[CH3:31])[C@H:32]2[OH:33])[C@@H:34]([CH2:35][CH:36]=[O:37])[CH2:38][C@@H:39]([CH3:40])[C:41](=[O:42])[CH:43]=[CH:44][CH:45]2[O:46][CH:47]2[CH2:48][C@@H:49]([CH3:50])[O:51][C:52](=[O:53])[CH2:54][C@H:55]1[O:56][C:57]([CH3:58])=[O:59]", + "correct_smiles": "CO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)C(=O)C=CC2OC2C[C@@H](C)OC(=O)C[C@H]1OC(C)=O", + "predicted_raw": "5, Ring2 (C2'), O7, H.\nWait, the SMILES string is: `[O:5][C@@H:6]2[O:7]...`\nActually, it's `[O:5]` then `[C@@H:6]`. The neighbors of 6 are: O5 (from left), Ring2 (C32), O7 (forward), H (implicit).\nOrder: O5, C32, O7.\n`@@` means clockwise.\nLooking from H, O5 -> C32 -> O7 is clockwise.\nLet's draw it: C1' is up (beta). O5 is up.\nIf O5 is up, C32 is right-", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000241", + "op_type": "flip_ez", + "image_path": "images/000241.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000240", + "op_type": "flip_ez", + "image_path": "images/000240.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000238", + "op_type": "flip_chirality", + "image_path": "images/000238.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@H:5]([CH2:6][C:7](=[O:8])[OH:9])[CH2:10][N+:11]([CH3:12])([CH3:13])[CH3:14]", + "correct_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 5}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 5 + } + }, + "restored_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000237", + "op_type": "flip_chirality", + "image_path": "images/000237.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[C@H:13]([OH:14])[CH2:15][C@:16]2([CH3:17])[C@@H:18]([c:19]3[cH:20][cH:21][c:22](=[O:23])[o:24][cH:25]3)[CH2:26][CH2:27][C@:28]12[OH:29]", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2[C@H](O)C[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "C[C@]12CC[C@H](O)C[C@@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000236", + "op_type": "flip_chirality", + "image_path": "images/000236.png", + "wrong_smiles_mapped": "[CH3:1][C:2]#[C:3][C@:4]1([OH:5])[CH2:6][CH2:7][C@H:8]2[C@@H:9]3[CH2:10][C@H:11]([CH3:12])[C:13]4=[CH:14][C:15](=[O:16])[CH2:17][CH2:18][C@:19]4([CH3:20])[C@H:21]3[CH2:22][CH2:23][C@@:24]12[CH3:25]", + "correct_smiles": "CC#C[C@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C", + "predicted_raw": " o'clock) is clockwise!\nSo 12 must be pointing towards us (wedged) or away (dashed)?\nLet's use standard rules.\nAtom 11 is the chiral center.\nNeighbors: 10, 12, 13, H.\nCoordinates:\n13 is at (-0.866, 0.5)\n10 is at (0.866, 0.5)\n12 is at (0, -1)\nIf 12 is in plane, 10 -> 12 -> 13 is clockwise.\nBut SMILES says `[C@]` which is anti-clockwise.\nSo H must be pointing towards us (wedged), which means", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000243", + "op_type": "flip_ez", + "image_path": "images/000243.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000242", + "op_type": "flip_ez", + "image_path": "images/000242.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000244", + "op_type": "flip_ez", + "image_path": "images/000244.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000232", + "op_type": "flip_chirality", + "image_path": "images/000232.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]1[O:9][c:10]1[cH:11][c:12]3[c:13]([cH:14][c:15]1[O:16][CH3:17])[CH2:18][CH2:19][N+:20]([CH3:21])([CH3:22])[C@@H:23]3[CH2:24][c:25]1[cH:26][cH:27][c:28]([cH:29][cH:30]1)[O:31][c:32]1[c:33]([O:34][CH3:35])[c:36]([O:37][CH3:38])[cH:39][c:40]3[c:41]1[C@@H:42]([CH2:43]2)[N+:44]([CH3:45])([CH3:46])[CH2:47][CH2:48]3", + "correct_smiles": "COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+](C)(C)[C@H]3Cc1ccc(cc1)Oc1c(OC)c(OC)cc3c1[C@@H](C2)[N+](C)(C)CC3", + "predicted_raw": " (CH2) is 4.\nWait, 1 and 6 are ortho. 1 and 4 are para. 6 and 4 are meta.\nThis matches the image perfectly!\n\nLet's check the bottom phenyl ring.\nImage:\nConnected to left THIQ via CH2.\nConnected to right THIQ via O.\nIt has NO methoxy groups.\nIt is a p-substituted benzene ring.\nLet's check the image:\nLeft side: CH2 linkage.\nRight side: O linkage.\nThey are para to each other.\nLet's check the SMILES:\n`[c:25]1[cH:26][cH:27][c:28]([cH:2", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000239", + "op_type": "flip_chirality", + "image_path": "images/000239.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@H:11]1[O:12][C@H:13]([CH2:14][O:15][P:16](=[O:17])([OH:18])[OH:19])[C@@H:20]([OH:21])[C@H:22]1[OH:23]", + "correct_smiles": "Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O", + "predicted_raw": "0.866, 0).\nOH at (0, -1, 1) (solid wedge, pointing down-left in 2D, but UP in 3D).\nH at (0, -1, -1) (dashed wedge, pointing down-left in 2D, but DOWN in 3D).\nWait, usually in Haworth-like or standard 2D projections of ribose:\nC2' is at the bottom left.\nThe bonds to C1' and C3' are in the ring plane.\nThe bond to OH is pointing towards us (solid wedge).\nThe bond to H is pointing away (dashed wedge).\nSo OH is +z, H is -z.\nPriority 1: OH (+", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + } +] \ No newline at end of file diff --git a/data/benchmark_results_gemini31.json b/data/benchmark_results_gemini31.json new file mode 100644 index 0000000000000000000000000000000000000000..7f93cbfa7090a8a2efd2cbf06bfe809ae9508db1 --- /dev/null +++ b/data/benchmark_results_gemini31.json @@ -0,0 +1,5203 @@ +[ + { + "id": "000004", + "op_type": "add_bond", + "image_path": "images/000004.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:12]1.[OH2:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 10}, \"atom2\": {\"map_num\": 11}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000003", + "op_type": "remove_bond", + "image_path": "images/000003.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1([CH3:4])[CH2:3][O:9][c:8]2[cH:7][cH:6][c:5]1[cH:12][c:10]2[OH:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 9}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000002", + "op_type": "add_atom", + "image_path": "images/000002.png", + "wrong_smiles_mapped": "[CH:1]([CH3:2])([CH3:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000007", + "op_type": "move_substituent", + "image_path": "images/000007.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:7]1[cH:6][cH:5][cH:12][c:10]([OH:11])[c:8]1[OH:9]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 5}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 5 + } + }, + "restored_smiles": "CC(C)(C)c1cc(O)ccc1O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000000", + "op_type": "change_atom_element", + "image_path": "images/000000.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([SH:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\n \"type\": \"ChangeAtom\",\n \"atom\": {\n \"map_num\": 3\n },\n \"element\": \"C\",\n \"charge\": 0\n}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000010", + "op_type": "remove_atom", + "image_path": "images/000010.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][NH2:14])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000001", + "op_type": "remove_atom", + "image_path": "images/000001.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([O:11][CH3:13])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000006", + "op_type": "add_functional_group", + "image_path": "images/000006.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 8}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 8 + }, + "group": "OH" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000012", + "op_type": "change_charge", + "image_path": "images/000012.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[OH+:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 12}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 12 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000015", + "op_type": "add_bond", + "image_path": "images/000015.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12].[OH2:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 11}, \"atom2\": {\"map_num\": 13}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 13 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000008", + "op_type": "swap_substituents", + "image_path": "images/000008.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(C)(C)c1cccc(O)c1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000011", + "op_type": "add_atom", + "image_path": "images/000011.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 11}, \"element\": \"O\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 11 + }, + "element": "O", + "bond_order": "SINGLE" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000013", + "op_type": "change_bond_order", + "image_path": "images/000013.png", + "wrong_smiles_mapped": "[NH:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\n \"type\": \"ChangeBond\",\n \"bond\": {\n \"atom1\": {\n \"map_num\": 1\n },\n \"atom2\": {\n \"map_num\": 2\n }\n },\n \"order\": \"SINGLE\"\n}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000014", + "op_type": "remove_bond", + "image_path": "images/000014.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:10]1)[O:9]2)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 9}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000017", + "op_type": "add_functional_group", + "image_path": "images/000017.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 6}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 6 + }, + "group": "OH" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000009", + "op_type": "change_atom_element", + "image_path": "images/000009.png", + "wrong_smiles_mapped": "[NH2:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000019", + "op_type": "change_atom_element", + "image_path": "images/000019.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([SH:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 14}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000016", + "op_type": "remove_functional_group", + "image_path": "images/000016.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:14])[c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000021", + "op_type": "add_atom", + "image_path": "images/000021.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 13}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 13 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000020", + "op_type": "remove_atom", + "image_path": "images/000020.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH2:14][OH:21])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 13}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "OH" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='OH' not found at anchor=12" + }, + { + "id": "000022", + "op_type": "remove_bond", + "image_path": "images/000022.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]-2[c:7]2[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]24)[cH:18][c:19]3[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 6}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000018", + "op_type": "move_substituent", + "image_path": "images/000018.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:10]1[OH:9])[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000024", + "op_type": "remove_functional_group", + "image_path": "images/000024.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH3:21])[c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 21}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 21 + } + }, + "restored_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000025", + "op_type": "add_functional_group", + "image_path": "images/000025.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]3[c:7]([cH:8][cH:9][c:10]4[cH:11][c:12]([CH3:13])[cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cc3ccc4cc(C)ccc4c3cc2c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000023", + "op_type": "add_bond", + "image_path": "images/000023.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Cc1ccc2cc3ccc4cc(C)ccc4c3cc2c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000026", + "op_type": "move_substituent", + "image_path": "images/000026.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][c:15]([CH3:14])[cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 17}, \"from_atom\": {\"map_num\": 7}, \"to_atom\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 17 + }, + "from_atom": { + "map_num": 7 + }, + "to_atom": { + "map_num": 6 + } + }, + "restored_smiles": "Cc1ccc2c(c1)-c1cc(cc3cc(C)ccc13)C=C2", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000027", + "op_type": "swap_substituents", + "image_path": "images/000027.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:20][c:19]2[c:5]3[cH:6][c:7]([c:8]([cH:18]2)[CH:4]=[CH:3]1)-[c:17]1[c:11]([cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[CH:10]=[CH:9]3", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 20}, \"atom2\": {\"map_num\": 19}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 20 + }, + "atom2": { + "map_num": 19 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC1=Cc2cc(c3cc2C=Cc2cc(C)ccc2-3)C=C1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000028", + "op_type": "remove_atom", + "image_path": "images/000028.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[OH:46])[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 46}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 46 + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000030", + "op_type": "change_charge", + "image_path": "images/000030.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[NH+:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 17}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 17 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000005", + "op_type": "remove_functional_group", + "image_path": "images/000005.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:13])[c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000033", + "op_type": "add_bond", + "image_path": "images/000033.png", + "wrong_smiles_mapped": "[O:1]=[S:2]([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1.[OH2:3]", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000032", + "op_type": "remove_bond", + "image_path": "images/000032.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]3[c:39]4[cH:40][cH:41][cH:42][c:43]([c:44]24)-[c:37]2[cH:36][cH:35][c:30]([S:31](=[O:32])(=[O:33])[OH:34])[c:29]4[c:21]([NH:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:20][cH:19][c:18]([c:38]42)[N:17]=[N:16]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "29 and 37.\nSo the right part is a naphthalene ring:\nRing 1: 37-36-35-30-29-38-37\nRing 2: 29-21-20-19-18-38-29\nThis is a naphthalene ring.\nSubstituents on right naphthalene:\nAt 30: SO3H\nAt 21: NHPh\nAt 18: N=N\nLet's check the relative positions.\n38 is the bridgehead between 37 and 18.\n29 is the bridgehead between 30 and 21.\nSo 37, 36, ", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000031", + "op_type": "change_bond_order", + "image_path": "images/000031.png", + "wrong_smiles_mapped": "[OH:1][SH:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000036", + "op_type": "change_atom_element", + "image_path": "images/000036.png", + "wrong_smiles_mapped": "[NH2:1][NH:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000039", + "op_type": "change_bond_order", + "image_path": "images/000039.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[SH:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000037", + "op_type": "remove_atom", + "image_path": "images/000037.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 12}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000029", + "op_type": "add_atom", + "image_path": "images/000029.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])[OH:33])[cH:34][cH:35][cH:36][c:37]34)[c:38]3[cH:39][cH:40][cH:41][cH:42][c:43]23)[cH:44]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 31}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 31 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000040", + "op_type": "remove_bond", + "image_path": "images/000040.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[c:7]2[cH:8][cH:9][cH:10][c:11]1-2", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 11}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 11 + } + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000038", + "op_type": "add_atom", + "image_path": "images/000038.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"NH2\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "NH2" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000042", + "op_type": "remove_functional_group", + "image_path": "images/000042.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[Cl:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 12}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000044", + "op_type": "change_atom_element", + "image_path": "images/000044.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][P:9](=[O:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 8}, \"element\": \"S\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 8 + }, + "element": "S", + "charge": 0 + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000034", + "op_type": "remove_functional_group", + "image_path": "images/000034.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[c:13]([Cl:46])[cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 46}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 46 + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000041", + "op_type": "add_bond", + "image_path": "images/000041.png", + "wrong_smiles_mapped": "[CH3:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH3:2]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000043", + "op_type": "add_functional_group", + "image_path": "images/000043.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"NH2\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "NH2" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000047", + "op_type": "change_charge", + "image_path": "images/000047.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[OH+:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000035", + "op_type": "move_substituent", + "image_path": "images/000035.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][C:12]2=[CH:13][CH:14]=[C:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:41]3[cH:40][cH:39][c:44]2[cH:43][cH:42]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 44}, \"from_atom\": {\"map_num\": 39}, \"to_atom\": {\"map_num\": 40}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 44 + }, + "from_atom": { + "map_num": 39 + }, + "to_atom": { + "map_num": 40 + } + }, + "restored_smiles": "C=C1C2=CC=C1C(N=Nc1ccc(Nc3ccccc3)c3c(S(=O)(=O)O)cccc13)=CC=C2N=Nc1cccc(S(=O)(=O)O)c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000046", + "op_type": "add_atom", + "image_path": "images/000046.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9](=[O:10])[OH:11]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 9}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 9 + }, + "group": "OH" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000048", + "op_type": "change_bond_order", + "image_path": "images/000048.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9]([OH:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 9}, \"atom2\": {\"map_num\": 12}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 9 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000050", + "op_type": "add_bond", + "image_path": "images/000050.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12].[NH2:1][CH3:2]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000051", + "op_type": "remove_functional_group", + "image_path": "images/000051.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[F:13]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000049", + "op_type": "remove_bond", + "image_path": "images/000049.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[O:12]1", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 12}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 12 + } + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000045", + "op_type": "remove_atom", + "image_path": "images/000045.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[OH:13]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000059", + "op_type": "change_atom_element", + "image_path": "images/000059.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][SH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 17}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 17 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000052", + "op_type": "add_functional_group", + "image_path": "images/000052.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][S:7][P:8](=[O:9])([OH:10])[OH:11]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"N\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeAtom): Explicit valence for atom # 0 N, 4, is greater than permitted" + }, + { + "id": "000060", + "op_type": "remove_atom", + "image_path": "images/000060.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[NH2:25]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000058", + "op_type": "remove_functional_group", + "image_path": "images/000058.png", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([CH3:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000056", + "op_type": "change_bond_order", + "image_path": "images/000056.png", + "wrong_smiles_mapped": "[C:1]1=[CH:2][NH:3][CH2:4][N:5]=[C:6]=1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 6 + } + }, + "restored_smiles": "C=CNCN", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000053", + "op_type": "change_atom_element", + "image_path": "images/000053.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][N:5]=[N:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"C\"}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "C" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000055", + "op_type": "change_charge", + "image_path": "images/000055.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][NH+:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000062", + "op_type": "change_charge", + "image_path": "images/000062.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH+:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 11}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 11 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000061", + "op_type": "add_atom", + "image_path": "images/000061.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 16}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 16 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000057", + "op_type": "remove_bond", + "image_path": "images/000057.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH:4]2[N:5]=[C:6]12", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 6}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000063", + "op_type": "change_bond_order", + "image_path": "images/000063.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000054", + "op_type": "remove_atom", + "image_path": "images/000054.png", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([NH2:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "```json\n{\"type\": \"RemoveGroup\", \"anchor\": {\"map_num\": 2}, \"group\": \"NH2\"}\n```", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "NH2" + }, + "restored_smiles": "C1=CNCN=C1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000067", + "op_type": "add_functional_group", + "image_path": "images/000067.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 16}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 16 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000066", + "op_type": "remove_functional_group", + "image_path": "images/000066.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[OH:25]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000064", + "op_type": "remove_bond", + "image_path": "images/000064.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]2[cH:14][c:15]([CH2:16][OH:17])[c:18]1[c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]2", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 18}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 18 + } + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000070", + "op_type": "remove_atom", + "image_path": "images/000070.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH:7]([OH:30])[CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 30}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 30 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000065", + "op_type": "add_bond", + "image_path": "images/000065.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH2:20])[cH:24]1.[CH:21]([CH3:22])=[O:23]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 20}, \"atom2\": {\"map_num\": 21}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 20 + }, + "atom2": { + "map_num": 21 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000075", + "op_type": "add_bond", + "image_path": "images/000075.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[O:1]=[CH:2][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000072", + "op_type": "change_charge", + "image_path": "images/000072.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][NH+:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000076", + "op_type": "remove_functional_group", + "image_path": "images/000076.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:30])[cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 30}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 30 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000074", + "op_type": "remove_bond", + "image_path": "images/000074.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][C:9]3([CH:10]1[CH2:11]2)[C:12](=[O:13])[NH:14][CH2:15][N:16]3[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 10}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 10 + } + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000071", + "op_type": "add_atom", + "image_path": "images/000071.png", + "wrong_smiles_mapped": "[CH2:1]([CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[C:11](=[O:12])[NH:13][CH2:14][N:15]2[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000073", + "op_type": "change_bond_order", + "image_path": "images/000073.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000069", + "op_type": "change_atom_element", + "image_path": "images/000069.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][O:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 11}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 11 + }, + "element": "C" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000068", + "op_type": "move_substituent", + "image_path": "images/000068.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][cH:15][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]1[CH2:16][OH:17]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 16}, \"from_atom\": {\"map_num\": 24}, \"to_atom\": {\"map_num\": 15}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 16 + }, + "from_atom": { + "map_num": 24 + }, + "to_atom": { + "map_num": 15 + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000077", + "op_type": "add_functional_group", + "image_path": "images/000077.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 26}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 26 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000082", + "op_type": "change_charge", + "image_path": "images/000082.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[OH+:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 25}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 25 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000078", + "op_type": "move_substituent", + "image_path": "images/000078.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][c:25]([F:27])[cH:26][cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 27}, \"from_atom\": {\"map_num\": 25}, \"to_atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 27 + }, + "from_atom": { + "map_num": 25 + }, + "to_atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000079", + "op_type": "change_atom_element", + "image_path": "images/000079.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][S:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 23}, \"element\": \"O\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 23 + }, + "element": "O" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000080", + "op_type": "remove_atom", + "image_path": "images/000080.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH:22]([OH:31])[O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000081", + "op_type": "add_atom", + "image_path": "images/000081.png", + "wrong_smiles_mapped": "[OH:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([O:7][CH3:8])[c:9]1[O:10][CH3:11])-[c:12]1[cH:13][c:14]3[c:15]([cH:16][c:17]1[C:18](=[O:19])[CH:20]1[CH2:21][O:22][C:23](=[O:24])[CH:25]1[CH2:26]2)[O:27][CH2:28][O:29]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000083", + "op_type": "change_bond_order", + "image_path": "images/000083.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[CH:19]([OH:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 19}, \"atom2\": {\"map_num\": 20}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 19 + }, + "atom2": { + "map_num": 20 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000084", + "op_type": "remove_bond", + "image_path": "images/000084.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([c:17]4[c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[C:26]41[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 17}, \"atom2\": {\"map_num\": 26}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 17 + }, + "atom2": { + "map_num": 26 + } + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000089", + "op_type": "remove_atom", + "image_path": "images/000089.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH:27]([CH3:31])[CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000088", + "op_type": "change_atom_element", + "image_path": "images/000088.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([NH:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 18}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 18 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000086", + "op_type": "remove_functional_group", + "image_path": "images/000086.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:21]1([NH2:31])[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000092", + "op_type": "change_bond_order", + "image_path": "images/000092.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH:15]=[CH:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 15}, \"atom2\": {\"map_num\": 16}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 15 + }, + "atom2": { + "map_num": 16 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000085", + "op_type": "add_bond", + "image_path": "images/000085.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3.[OH:8][CH3:9]", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 8}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 8 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000087", + "op_type": "move_substituent", + "image_path": "images/000087.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:26]1([CH2:21][CH2:22][O:23][C:24]1=[O:25])[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "22]`? No, I can only do one action.\nLet's re-read the image carefully.\nMaybe the wrong SMILES is NOT a spiro ring.\nLet's look at the SMILES again:\n`[C:19](=[O:20])[C:26]1([CH2:21][CH2:22][O:23][C:24]1=[O:25])[CH2:27]2`\nWait, `[C:26]1` means C26 is connected to C24.\nWhat if the bond is NOT C26-C24, but C26-C22? No.\nLet's look at the image", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000091", + "op_type": "change_charge", + "image_path": "images/000091.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[NH+:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 14}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000098", + "op_type": "change_atom_element", + "image_path": "images/000098.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[S:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 9 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000095", + "op_type": "remove_functional_group", + "image_path": "images/000095.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)([N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[CH3:31])[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 31}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000090", + "op_type": "add_atom", + "image_path": "images/000090.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000094", + "op_type": "add_bond", + "image_path": "images/000094.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1.[cH:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000096", + "op_type": "add_functional_group", + "image_path": "images/000096.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000099", + "op_type": "remove_atom", + "image_path": "images/000099.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH2:8][CH3:25])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000100", + "op_type": "add_atom", + "image_path": "images/000100.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4]([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 4}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 4 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000093", + "op_type": "remove_bond", + "image_path": "images/000093.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]2[cH:29][c:30]1[CH:16]1[CH2:15][N:14]([CH:6]2[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[CH2:28][CH2:27][N:17]1[CH2:18][CH:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 16}, \"atom2\": {\"map_num\": 30}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 16 + }, + "atom2": { + "map_num": 30 + } + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000102", + "op_type": "change_bond_order", + "image_path": "images/000102.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4]([OH:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 5}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000097", + "op_type": "move_substituent", + "image_path": "images/000097.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:9]2[cH:8][cH:7][cH:13][cH:12][c:10]2[F:11])[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 13 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000103", + "op_type": "remove_bond", + "image_path": "images/000103.png", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]2[C:11](=[O:12])[c:13]3[c:14]1[cH:15][cH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([c:22]31)[C:23]2=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 14}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 14 + } + } + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000101", + "op_type": "change_charge", + "image_path": "images/000101.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][OH+:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000106", + "op_type": "add_functional_group", + "image_path": "images/000106.png", + "wrong_smiles_mapped": "[CH3:1][O:2][P:3](=[O:4])([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000112", + "op_type": "change_charge", + "image_path": "images/000112.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[OH+:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 26}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 26 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000105", + "op_type": "remove_functional_group", + "image_path": "images/000105.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][c:15]([Cl:25])[cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 25}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 25 + } + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000107", + "op_type": "move_substituent", + "image_path": "images/000107.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][n:10]1[c:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][c:17]([cH:22]2)[CH:18]=[CH:19][CH:20]=[c:21]3[c:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "c:13]2[cH:14][c:15]3[cH:16][c:17]([cH:22]2)[CH:18]=[CH:19][CH:20]=[c:21]3`\nLet's trace the outer loop:\n13 - 14 - 15 - 21 - 20 - 19 - 18 - 17 - 22 - 13.\nThis is a 9-membered outer loop.\nWait, 13(1)-14(2)-15(3)-21(4)-20(5)-19(6)-18(7)-17(8)-2", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000108", + "op_type": "swap_substituents", + "image_path": "images/000108.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][C:22]1=[C:13]2[C:11](=[O:12])[N:10]3[C:17](=[CH:16][CH:15]=[CH:14]2)[CH:18]=[CH:19][CH:20]=[C:21]1[C:23]3=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": ")`\n`[N:10]3`\n`[C:17](=[CH:16][CH:15]=[CH:14]2)`\n`[CH:18]=[CH:19][CH:20]=[C:21]1`\n`[C:23]3=[O:24]`\nLet's re-evaluate the connections.\n`[C:17]` is bonded to `[CH:16]` (double).\n`[CH:16]` is bonded to `[CH:15]` (single).\n`[CH:15]` is bonded to `[CH:14]` (double).\n`[CH:14]` is bonded to `[C", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000111", + "op_type": "add_atom", + "image_path": "images/000111.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][SH:29](=[O:30])=[O:31])[CH:32]([OH:33])[CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 29}, \"element\": \"O\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 29 + }, + "element": "O", + "bond_order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000113", + "op_type": "change_bond_order", + "image_path": "images/000113.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 16}, \"atom2\": {\"map_num\": 17}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 16 + }, + "atom2": { + "map_num": 17 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000110", + "op_type": "remove_atom", + "image_path": "images/000110.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[C:35]([OH:36])([CH3:57])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 57}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 57 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000114", + "op_type": "remove_bond", + "image_path": "images/000114.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 8}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000104", + "op_type": "add_bond", + "image_path": "images/000104.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4](=[O:5])[O:6][CH2:7][CH3:8].[OH:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 9}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 9 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000117", + "op_type": "add_functional_group", + "image_path": "images/000117.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH2:33][CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 33}, \"group\": \"OH\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 33 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000115", + "op_type": "add_bond", + "image_path": "images/000115.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 17}, \"atom2\": {\"map_num\": 18}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 17 + }, + "atom2": { + "map_num": 18 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000116", + "op_type": "remove_functional_group", + "image_path": "images/000116.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[Br:57]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 57}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 57 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000121", + "op_type": "remove_atom", + "image_path": "images/000121.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[CH3:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 7}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000118", + "op_type": "move_substituent", + "image_path": "images/000118.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][C:25]1([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH2:27][CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 28}, \"from_atom\": {\"map_num\": 25}, \"to_atom\": {\"map_num\": 27}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 28 + }, + "from_atom": { + "map_num": 25 + }, + "to_atom": { + "map_num": 27 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000109", + "op_type": "change_atom_element", + "image_path": "images/000109.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000122", + "op_type": "add_atom", + "image_path": "images/000122.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000120", + "op_type": "change_atom_element", + "image_path": "images/000120.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[N:4]([OH:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000119", + "op_type": "swap_substituents", + "image_path": "images/000119.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:35]1[CH:33]([OH:34])[CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH:25]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 33}, \"atom2\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 33 + }, + "atom2": { + "map_num": 26 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (SwapSubstituents): Explicit valence for atom # 33 O, 3, is greater than permitted" + }, + { + "id": "000125", + "op_type": "remove_bond", + "image_path": "images/000125.png", + "wrong_smiles_mapped": "[CH2:1]1[C:2](=[O:3])[N:4]([NH2:6])[CH2:5]1", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 5}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 5 + } + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000124", + "op_type": "change_bond_order", + "image_path": "images/000124.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([OH:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000128", + "op_type": "add_functional_group", + "image_path": "images/000128.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000132", + "op_type": "change_charge", + "image_path": "images/000132.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000127", + "op_type": "remove_functional_group", + "image_path": "images/000127.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[NH2:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 7}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000130", + "op_type": "remove_atom", + "image_path": "images/000130.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH:6]([NH2:26])[CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000129", + "op_type": "change_atom_element", + "image_path": "images/000129.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[N:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 21}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 21 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000126", + "op_type": "add_bond", + "image_path": "images/000126.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][N:4]([CH3:5])[NH2:6].[OH2:3]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000123", + "op_type": "change_charge", + "image_path": "images/000123.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[OH+:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000136", + "op_type": "remove_functional_group", + "image_path": "images/000136.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][C:4]2([F:26])[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 26 + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000133", + "op_type": "change_bond_order", + "image_path": "images/000133.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH2:7][CH:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 7}, \"atom2\": {\"map_num\": 8}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 7 + }, + "atom2": { + "map_num": 8 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000131", + "op_type": "add_atom", + "image_path": "images/000131.png", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][CH:3]2[O:4][CH2:5][CH:6]=[C:7]3[CH2:8][N:9]4[CH2:10][CH2:11][C@:12]56[c:13]7[cH:14][cH:15][cH:16][cH:17][c:18]7[N:19]1[CH:20]5[C@H:21]2[C@H:22]3[CH2:23][C@H:24]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"O\", \"bond_order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "O", + "bond_order": "DOUBLE" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000141", + "op_type": "add_atom", + "image_path": "images/000141.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000139", + "op_type": "change_atom_element", + "image_path": "images/000139.png", + "wrong_smiles_mapped": "[F:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000138", + "op_type": "move_substituent", + "image_path": "images/000138.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:6]2[O:5][CH2:4][C@H:22]3[CH:21]4[C@:13]5([CH2:12][CH2:11][N:10]6[CH2:9][C:8](=[CH:7]2)[C@@H:23]3[CH2:24][C@H:25]65)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]14", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 4}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 4 + } + }, + "restored_smiles": "O=C1CC2C=C3CN4CC[C@]56c7ccccc7N1C5[C@H](CO2)[C@H]3C[C@H]46", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000137", + "op_type": "flip_chirality", + "image_path": "images/000137.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 23}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 23 + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@@H]2[C@@H]3C[C@H]46", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000142", + "op_type": "remove_bond", + "image_path": "images/000142.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][c:8]1-2", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 8}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000134", + "op_type": "remove_bond", + "image_path": "images/000134.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH:3]2[CH:4]3[O:5][CH2:6][CH:7]=[C:8]4[CH:9]2[N:10]2[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]3[C@H:23]4[CH2:24][C@H:25]26", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 9}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000145", + "op_type": "add_functional_group", + "image_path": "images/000145.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"F\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000140", + "op_type": "remove_atom", + "image_path": "images/000140.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH3:9]", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000144", + "op_type": "remove_functional_group", + "image_path": "images/000144.png", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:9])[cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000143", + "op_type": "add_bond", + "image_path": "images/000143.png", + "wrong_smiles_mapped": "[F:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "correct_smiles": "FCc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "FCc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000135", + "op_type": "add_bond", + "image_path": "images/000135.png", + "wrong_smiles_mapped": "[CH2:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46.[OH2:1]", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "```json\n{\n \"type\": \"AddBond\",\n \"bond\": {\n \"atom1\": {\n \"map_num\": 2\n },\n \"atom2\": {\n \"map_num\": 1\n }\n },\n \"order\": \"DOUBLE\"\n}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 1 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000146", + "op_type": "change_atom_element", + "image_path": "images/000146.png", + "wrong_smiles_mapped": "[Cl:1][O:2][c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000148", + "op_type": "add_atom", + "image_path": "images/000148.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"Cl\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "Cl", + "bond_order": "SINGLE" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000151", + "op_type": "remove_functional_group", + "image_path": "images/000151.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Br:9]", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000152", + "op_type": "add_functional_group", + "image_path": "images/000152.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"Cl\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "Cl", + "bond_order": "SINGLE" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000153", + "op_type": "move_substituent", + "image_path": "images/000153.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:6]1[cH:5][cH:4][cH:3][cH:8][n:7]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 2}, \"from_atom\": {\"map_num\": 6}, \"to_atom\": {\"map_num\": 5}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 2 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 5 + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000154", + "op_type": "change_atom_element", + "image_path": "images/000154.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 10}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000149", + "op_type": "remove_bond", + "image_path": "images/000149.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]1-2", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\n \"type\": \"RemoveBond\",\n \"bond\": {\n \"atom1\": {\n \"map_num\": 5\n },\n \"atom2\": {\n \"map_num\": 8\n }\n }\n}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000147", + "op_type": "remove_atom", + "image_path": "images/000147.png", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH3:9]", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": " attached to CH2Cl)\n2. Top-Left\n3. Top-Right\n4. Right\n5. Bottom-Right (N)\n6. Bottom-Left\nLet's check the bonds for this:\n- Left to Top-Left: UP-RIGHT\n- Top-Left to Top-Right: HORIZONTAL\n- Top-Right to Right: DOWN-RIGHT\n- Right to Bottom-Right (N): DOWN-LEFT\n- Bottom-Right (N) to Bottom-Left: HORIZONTAL\n- Bottom-Left to Left: UP-LEFT\nLet's look at the image.\nIs there a horizontal bond at the bottom?\nYes, the bond to the left of N looks horizontal!\nWait, N is at the bottom right.", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000155", + "op_type": "remove_atom", + "image_path": "images/000155.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([CH3:14])[cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000150", + "op_type": "add_bond", + "image_path": "images/000150.png", + "wrong_smiles_mapped": "[Cl:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "correct_smiles": "ClCc1cccnc1", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "ClCc1cccnc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000162", + "op_type": "change_atom_element", + "image_path": "images/000162.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000157", + "op_type": "remove_bond", + "image_path": "images/000157.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[cH:7][c:8]-3[c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 8}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 8 + } + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000158", + "op_type": "add_bond", + "image_path": "images/000158.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000159", + "op_type": "remove_functional_group", + "image_path": "images/000159.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]([Cl:14])[c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000165", + "op_type": "change_charge", + "image_path": "images/000165.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[OH+:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000164", + "op_type": "add_atom", + "image_path": "images/000164.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[CH:4][CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 4}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 4 + }, + "group": "CH3" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000166", + "op_type": "change_bond_order", + "image_path": "images/000166.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 4}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000156", + "op_type": "add_atom", + "image_path": "images/000156.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 7 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000160", + "op_type": "add_functional_group", + "image_path": "images/000160.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 7 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000167", + "op_type": "remove_bond", + "image_path": "images/000167.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]1[CH:3]=[C:4]([CH3:5])[C:6]1=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"RemoveBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 6}}}\n```", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 6 + } + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000170", + "op_type": "add_functional_group", + "image_path": "images/000170.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]=[C:3]([CH3:4])[CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"C\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000168", + "op_type": "add_bond", + "image_path": "images/000168.png", + "wrong_smiles_mapped": "[CH2:3]=[C:4]([CH3:5])[CH:6]=[O:7].[CH3:1][CH3:2]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000161", + "op_type": "move_substituent", + "image_path": "images/000161.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[C:12]([CH3:13])[c:11]2[cH:5][cH:6][cH:7][c:8]([c:9]2[CH3:10])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 9}}, \"order\": \"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 9 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CC1=C(C)c2cccc(c2C)C=C1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000169", + "op_type": "remove_functional_group", + "image_path": "images/000169.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[Br:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 8 + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000163", + "op_type": "remove_atom", + "image_path": "images/000163.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[CH3:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 8 + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000172", + "op_type": "remove_atom", + "image_path": "images/000172.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[NH2:13])[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000174", + "op_type": "change_charge", + "image_path": "images/000174.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[OH+:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 9}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 9 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000171", + "op_type": "change_atom_element", + "image_path": "images/000171.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"C\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000176", + "op_type": "add_bond", + "image_path": "images/000176.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][NH:12]2.[OH2:11]", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 10}, \"atom2\": {\"map_num\": 11}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000175", + "op_type": "change_bond_order", + "image_path": "images/000175.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH:10]([OH:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 11}, \"element\": \"O\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 11 + }, + "element": "O" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(O)N2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000179", + "op_type": "move_substituent", + "image_path": "images/000179.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:7][N:12]2[C:5](=[CH:6][C:8](=[O:9])[C:10]2=[O:11])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"N\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "N" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeAtom): Explicit valence for atom # 5 N, 4, is greater than permitted" + }, + { + "id": "000178", + "op_type": "add_functional_group", + "image_path": "images/000178.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 1}, \"group\": \"CH3\"}\n```", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000183", + "op_type": "change_charge", + "image_path": "images/000183.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[NH+:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"N\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000177", + "op_type": "remove_functional_group", + "image_path": "images/000177.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[c:3]([Cl:13])[cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000181", + "op_type": "change_atom_element", + "image_path": "images/000181.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][SH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 6}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "C" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000184", + "op_type": "change_bond_order", + "image_path": "images/000184.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][C:6]2=[C:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 6}, \"atom2\": {\"map_num\": 7}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000173", + "op_type": "add_atom", + "image_path": "images/000173.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": " to (1, -0.5)? Yes, up-right.\nLet me re-read the image.\nIs there a vertical bond on the left?\nLooking at the image, the leftmost part of the benzene ring is a VERTEX, not a vertical edge.\nWait, if the leftmost part is a vertex, then the top and bottom edges must be horizontal.\nLet's check if top and bottom edges are horizontal.\nTop edge: from top fused carbon, goes left (horizontal).\nBottom edge: from bottom fused carbon, goes left (horizontal).\nLet's check the image.\nYes! The top edge of the benzene ring is horizontal.\nThe bottom edge of the benzene ring is horizontal.\nSo the vertices are:\nTop", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000182", + "op_type": "add_atom", + "image_path": "images/000182.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH3:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 12}, \"element\": \"O\", \"bond_order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 12 + }, + "element": "O", + "bond_order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000180", + "op_type": "swap_substituents", + "image_path": "images/000180.png", + "wrong_smiles_mapped": "[CH3:1][c:5]1[cH:4][cH:3][c:2]2[cH:7][c:6]1[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 1}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 4}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 1 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 4 + } + }, + "restored_smiles": "Cc1cc2cc(c1)C(=O)C(=O)N2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000190", + "op_type": "change_charge", + "image_path": "images/000190.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000191", + "op_type": "change_bond_order", + "image_path": "images/000191.png", + "wrong_smiles_mapped": "[OH:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 1}, \"atom2\": {\"map_num\": 2}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000185", + "op_type": "remove_bond", + "image_path": "images/000185.png", + "wrong_smiles_mapped": "[CH3:1][N:2]1[CH2:3][C:9]2([OH:10])[CH:7]([OH:8])[CH:6]3[N:5]=[C:4]1[O:15][CH:14]3[CH:11]2[CH2:12][OH:13]", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 3}, \"element\": \"C\"}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "C" + }, + "restored_smiles": "CN1CC2(O)C(O)C3N=C1OC3C2CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000186", + "op_type": "add_bond", + "image_path": "images/000186.png", + "wrong_smiles_mapped": "[CH3:12][OH:13].[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\": \"AddBond\", \"bond\": {\"atom1\": {\"map_num\": 11}, \"atom2\": {\"map_num\": 12}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000192", + "op_type": "add_functional_group", + "image_path": "images/000192.png", + "wrong_smiles_mapped": "[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]1[OH:12]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 2}, \"element\": \"O\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 2 + }, + "element": "O", + "bond_order": "SINGLE" + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000195", + "op_type": "add_functional_group", + "image_path": "images/000195.png", + "wrong_smiles_mapped": "[cH:1]1[n:2][c:3]([Cl:4])[n:5][c:6]([C:7]([Cl:8])([Cl:9])[Cl:10])[n:11]1", + "correct_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "predicted_raw": "```json\n{\"type\": \"AddAtom\", \"anchor\": {\"map_num\": 1}, \"element\": \"Cl\", \"bond_order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "Cl", + "bond_order": "SINGLE" + }, + "restored_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000188", + "op_type": "move_substituent", + "image_path": "images/000188.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][C:14]2([CH2:12][OH:13])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 12}, \"from_atom\": {\"map_num\": 14}, \"to_atom\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 12 + }, + "from_atom": { + "map_num": 14 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000189", + "op_type": "swap_substituents", + "image_path": "images/000189.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[CH:14]1[CH:6]2[N:5]=[C:4]([CH:11]([CH2:12][OH:13])[CH:9]([OH:10])[CH:7]2[OH:8])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 11 + } + }, + "restored_smiles": "CC(C)C1OC2=NC1C(O)C(O)N2CO", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000187", + "op_type": "add_functional_group", + "image_path": "images/000187.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH2:7][CH:8]([OH:9])[CH:10]([CH2:11][OH:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\": \"AddGroup\", \"anchor\": {\"map_num\": 7}, \"group\": \"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 7 + }, + "group": "OH" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000194", + "op_type": "swap_substituents", + "image_path": "images/000194.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:13])[c:12]1[C:9](=[O:10])[OH:11]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 8}, \"atom2\": {\"map_num\": 12}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 12 + } + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000196", + "op_type": "change_charge", + "image_path": "images/000196.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[OH+:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 7}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000193", + "op_type": "move_substituent", + "image_path": "images/000193.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[c:5]([C:9](=[O:10])[OH:11])[cH:6][cH:7][cH:8][c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 5}, \"to_atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000200", + "op_type": "change_charge", + "image_path": "images/000200.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[OH+:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 43}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 43 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000197", + "op_type": "change_bond_order", + "image_path": "images/000197.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]=[CH:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 2}, \"atom2\": {\"map_num\": 3}}, \"order\": \"SINGLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000199", + "op_type": "move_substituent", + "image_path": "images/000199.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][c:15]([Cl:14])[cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 14}, \"from_atom\": {\"map_num\": 15}, \"to_atom\": {\"map_num\": 13}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 15 + }, + "to_atom": { + "map_num": 13 + } + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000202", + "op_type": "move_substituent", + "image_path": "images/000202.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:26]2([O:27][C:28]([CH3:29])=[O:30])[CH:25]=[C:24]3[CH:23]([CH:32]1[CH2:31]2)[CH:39]([O:40][C:41]([CH3:42])=[O:43])[O:38][CH:33]3[O:34][C:35]([CH3:36])=[O:37]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 12}, \"atom2\": {\"map_num\": 26}}", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 12 + }, + "atom2": { + "map_num": 26 + } + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC2(OC(C)=O)C=C3C(OC(C)=O)OC(OC(C)=O)C3C1CC2OC(=O)c1ccc(O)cc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000205", + "op_type": "change_bond_order", + "image_path": "images/000205.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][CH:4]([OH:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 4}, \"atom2\": {\"map_num\": 5}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000198", + "op_type": "add_functional_group", + "image_path": "images/000198.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 1}, \"element\": \"N\", \"charge\": 0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "NCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000207", + "op_type": "change_charge", + "image_path": "images/000207.png", + "wrong_smiles_mapped": "[CH3:1][OH+:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 2}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000201", + "op_type": "change_bond_order", + "image_path": "images/000201.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][CH:41]([CH3:42])[OH:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "C:23]`.\nAnd `[CH:33]` is attached to `[O:38]`.\n`[O:38]` is attached to `[CH:39]`.\n`[CH:39]` is attached to `[C:23]`.\nThis forms an oxetane: C23 - CH(OAc) - O - CH - C23.\nWait, the SMILES has `[CH:39]` attached to `[O:40][CH:41]([CH3:42])[OH:43]`.\nLet's look at the image.\nIs there an oxetane?\nNo, the image shows a 5-membered ring", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000206", + "op_type": "move_substituent", + "image_path": "images/000206.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[N:3]([Br:9])[C:4](=[O:5])[C:6]([Br:7])=[CH:8]1", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 9}, \"from_atom\": {\"map_num\": 3}, \"to_atom\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 3 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000204", + "op_type": "change_charge", + "image_path": "images/000204.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][C:4](=[OH+:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "```json\n{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 5}, \"element\": \"O\", \"charge\": 0}\n```", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C1NC(=O)C(Br)=C1Br", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000203", + "op_type": "swap_substituents", + "image_path": "images/000203.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:23]1([CH3:8])[CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[CH2:11][CH:9]([CH3:10])[C:7]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]21)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[O:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "```json\n{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 24}, \"atom2\": {\"map_num\": 33}}, \"order\": \"DOUBLE\"}\n```", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 24 + }, + "atom2": { + "map_num": 33 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 23 C, 5, is greater than permitted" + }, + { + "id": "000210", + "op_type": "swap_substituents", + "image_path": "images/000210.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:13]1[c:7]([CH3:14])[cH:8][cH:9][c:10]([Cl:11])[cH:12]1", + "correct_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 11}, \"from_atom\": {\"map_num\": 10}, \"to_atom\": {\"map_num\": 9}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 9 + } + }, + "restored_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000209", + "op_type": "swap_substituents", + "image_path": "images/000209.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:6]1[c:5](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[n:35](-[c:36]2[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]2)[c:33](=[O:34])[c:32]2[c:19]1[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][n:30]1)[cH:31]2", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 5}, \"atom2\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 6 + } + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000208", + "op_type": "move_substituent", + "image_path": "images/000208.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:18]2[O:16][CH3:17])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 16}, \"from_atom\": {\"map_num\": 18}, \"to_atom\": {\"map_num\": 15}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 16 + }, + "from_atom": { + "map_num": 18 + }, + "to_atom": { + "map_num": 15 + } + }, + "restored_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000212", + "op_type": "swap_substituents", + "image_path": "images/000212.png", + "wrong_smiles_mapped": "[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([CH2:10][CH2:11][Cl:12])[n:7][cH:8][n:9]2[n:13]([CH3:14])[c:15]1=[O:16]", + "correct_smiles": "Cn1c(=O)c2c(ncn2CCCl)n(C)c1=O", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 10}, \"from_atom\": {\"map_num\": 6}, \"to_atom\": {\"map_num\": 7}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 9 N, 4, is greater than permitted" + }, + { + "id": "000215", + "op_type": "swap_substituents", + "image_path": "images/000215.png", + "wrong_smiles_mapped": "[CH3:1][C:8]12[C:2]([CH3:9])([CH3:10])[CH:3]=[CH:4][CH:5]1[CH2:6][CH2:7]2", + "correct_smiles": "CC12C=CC(CC1)C2(C)C", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 7}, \"from_atom\": {\"map_num\": 8}, \"to_atom\": {\"map_num\": 5}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 7 + }, + "from_atom": { + "map_num": 8 + }, + "to_atom": { + "map_num": 5 + } + }, + "restored_smiles": "CC1C(C)(C)C=CC12CC2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000214", + "op_type": "swap_substituents", + "image_path": "images/000214.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([Cl:3])[c:6]1[cH:5][c:4]([Cl:7])[c:10]([Cl:11])[cH:9][cH:8]1", + "correct_smiles": "O=C(Cl)c1cc(Cl)ccc1Cl", + "predicted_raw": "{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 2}, \"from_atom\": {\"map_num\": 6}, \"to_atom\": {\"map_num\": 9}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 2 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 9 + } + }, + "restored_smiles": "O=C(Cl)c1cccc(Cl)c1Cl", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000211", + "op_type": "swap_substituents", + "image_path": "images/000211.png", + "wrong_smiles_mapped": "[CH3:1][NH:2][C:3](=[O:4])[CH:26]1[CH:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([NH2:19])[cH:20][cH:21]4)[n:22][cH:23][n:24][c:25]23)[O:6][CH:5]([OH:27])[CH:28]1[OH:29]", + "correct_smiles": "CNC(=O)C1OC(n2cnc3c(NCc4ccc(N)cc4)ncnc32)C(O)C1O", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 3}, \"atom2\": {\"map_num\": 27}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 27 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (SwapSubstituents): Explicit valence for atom # 26 O, 4, is greater than permitted" + }, + { + "id": "000216", + "op_type": "swap_substituents", + "image_path": "images/000216.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[S:5])([O:6][CH2:7][CH3:8])[O:9][c:12]1[cH:11][c:10]([CH3:13])[n:15][nH:14]1", + "correct_smiles": "CCOP(=S)(OCC)Oc1cc(C)[nH]n1", + "predicted_raw": "NH) is connected to 12(O) and 15(N).\n15(N) is connected to 14(NH) and 10(C-CH3).\n10(C-CH3) is connected to 15(N) and 11(CH).\n11(CH) is connected to 10(C-CH3) and 12(O).\nSo the SMILES sequence is: C(O) - NH - N - C(CH3) - CH - C(O).\nBut the image sequence is: C(O) - N - NH - C(CH3) - CH - C(O).\nWait, let me re-read the image", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000219", + "op_type": "swap_substituents", + "image_path": "images/000219.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([F:18])[cH:16][c:17]1[N:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1", + "correct_smiles": "CN(C)c1ccc(N=Nc2ccccc2)cc1F", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 18}, \"atom2\": {\"map_num\": 8}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 18 + }, + "atom2": { + "map_num": 8 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (SwapSubstituents): Explicit valence for atom # 7 F, 3, is greater than permitted" + }, + { + "id": "000218", + "op_type": "swap_substituents", + "image_path": "images/000218.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[c:11]([CH2:12][CH2:13][N:14]([CH3:15])[CH3:16])[cH:17][c:18]3[c:19]([c:20]2[O:21][CH3:22])[O:23][CH2:24][O:25]3)[c:26]([O:31][CH3:32])[c:30]1[C:27](=[O:28])[OH:29]", + "correct_smiles": "COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(C(=O)O)c1OC", + "predicted_raw": "```json\n{\"type\": \"SwapSubstituents\", \"atom1\": {\"map_num\": 26}, \"atom2\": {\"map_num\": 30}}\n```", + "predicted_action": { + "type": "SwapSubstituents", + "atom1": { + "map_num": 26 + }, + "atom2": { + "map_num": 30 + } + }, + "restored_smiles": "COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(C(=O)O)c1OC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000213", + "op_type": "swap_substituents", + "image_path": "images/000213.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[n:3][cH:4][c:5]([CH2:6][c:26]2[n+:7]([CH3:27])[cH:8][s:9][c:10]2[CH2:11][CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:18](=[O:19])([OH:20])[O:21][P:22](=[O:23])([O-:24])[OH:25])[c:28]([NH2:29])[n:30]1", + "correct_smiles": "Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)c2C)c(N)n1", + "predicted_raw": ") is attached to C(CH3).\nC(CH3) is attached to N+(Bridge).\nThis perfectly matches the image!\nImage: N+(Bridge) - CH - S - C(CH2CH2OPP) - C(CH3) - N+(Bridge).\nSo the substituents on c26 and n+7 are swapped in the SMILES.\nThe bridge is [CH2:6] (Wait, the bridge is a substituent? No, the bridge is part of the main chain in SMILES).\nLet's look at the SMILES string:\n`[CH3:1][c:2]1[n:3][cH:4][c:5]([CH2:6][c:2", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000220", + "op_type": "swap_substituents", + "image_path": "images/000220.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([F:13])[c:9]([OH:10])[cH:11][c:12]1[OH:8]", + "correct_smiles": "NCC(O)c1cc(O)c(O)cc1F", + "predicted_raw": "12]1[OH:8]\nWait, is c11 really `[cH:11]`? Yes.\nIs c12 really `[c:12]1[OH:8]`? Yes.\nLet's trace the ring again.\nc5 - c6 - c7 - c9 - c11 - c12 - c5\nSubstituents:\nc5: CH(OH)CH2NH2\nc6: H\nc7: F\nc9: OH\nc11: H\nc12: OH\nThis is 1-subst, 2-OH (c12), 4-OH (c9), 5-F (c7).\nWait!", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000223", + "op_type": "flip_chirality", + "image_path": "images/000223.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[C:11]1=[C:12]([CH2:13][C@H:14]([CH3:15])[O:16][C@H:17]1[CH3:18])[C:19]2=[O:20]", + "correct_smiles": "COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C2=O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 17}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 17 + } + }, + "restored_smiles": "COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C2=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000222", + "op_type": "flip_chirality", + "image_path": "images/000222.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([c:18]3[cH:19][cH:20][c:21](=[O:22])[o:23][cH:24]3)[CH2:25][CH2:26][C@:27]12[OH:28]", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 17}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 17 + } + }, + "restored_smiles": "C[C@]12CC[C@H](O)C[C@@H]1CCC1C2CC[C@]2(C)[C@H](c3ccc(=O)oc3)CC[C@]12O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000226", + "op_type": "flip_chirality", + "image_path": "images/000226.png", + "wrong_smiles_mapped": "[CH2:1]=[C:2]([CH3:3])[C@H:4]1[CH2:5][c:6]2[c:7]([cH:8][cH:9][c:10]3[c:11]2[O:12][C@H:13]2[CH2:14][O:15][c:16]4[cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24][c:25]4[C@@H:26]2[C:27]3=[O:28])[O:29]1", + "correct_smiles": "C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 26}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 26 + } + }, + "restored_smiles": "C=C(C)[C@H]1Cc2c(ccc3c2O[C@H]2COc4cc(OC)c(OC)cc4[C@H]2C3=O)O1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000224", + "op_type": "flip_chirality", + "image_path": "images/000224.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][n:7][c:8]2[c:9]1[n:10][cH:11][n:12]2[C@@H:13]1[O:14][C@@H:15]([CH2:16][OH:17])[C@@H:18]([O:19][P:20](=[O:21])([OH:22])[OH:23])[C@H:24]1[OH:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1", + "correct_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O)c1cccnc1", + "predicted_raw": "{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 18}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 18 + } + }, + "restored_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO)[C@H](OP(=O)(O)O)[C@H]1O)c1cccnc1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000227", + "op_type": "flip_chirality", + "image_path": "images/000227.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[NH:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15]", + "correct_smiles": "CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 6}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 6 + } + }, + "restored_smiles": "CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000225", + "op_type": "flip_chirality", + "image_path": "images/000225.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:8][CH2:9][CH:10]1[CH:11]2[CH2:12][CH2:13][C:14]2([CH3:15])[CH:16]1[CH2:17][CH2:18][C@H:19]2[OH:20]", + "correct_smiles": "CC12CCCC[C@@H]1CCC1C2CCC2(C)C1CC[C@@H]2O", + "predicted_raw": "Left-down from C_BL to a CH2.\nUp-left from that CH2 to the CH-OH.\nThis is the 5-membered ring.\nNow from C_TL, a bond goes right to a CH. Let's call it C_M1.\nFrom C_BL, a bond goes right to a CH2, then right to a CH. Let's call this CH C_M2.\nAre C_M1 and C_M2 connected?\nIf they are connected, the middle ring is C_TL - C_M1 - C_M2 - CH2 - C_BL. That's 5 atoms.\nBut looking at the image, C_M1 and C_M2 are connected", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000217", + "op_type": "flip_chirality", + "image_path": "images/000217.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@@H:5]([OH:6])[CH2:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[C:13](=[O:14])[CH2:15][C@@:16]2([CH3:17])[C@H:18]1[CH2:19][CH2:20][C@@:21]2([OH:22])[C:23](=[O:24])[CH2:25][OH:26]", + "correct_smiles": "C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO", + "predicted_raw": "```json\n{\"type\": \"MoveSubstituent\", \"substituent\": {\"map_num\": 14}, \"from_atom\": {\"map_num\": 13}, \"to_atom\": {\"map_num\": 19}}\n```", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 13 + }, + "to_atom": { + "map_num": 19 + } + }, + "restored_smiles": "C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C(=O)C[C@@]2(O)C(=O)CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000228", + "op_type": "flip_chirality", + "image_path": "images/000228.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH:5]3[c:6]4[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[c:13]4[CH2:14][CH2:15][CH:16]3[CH:17]1[CH2:18][CH2:19][C@H:20]2[OH:21]", + "correct_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@@H]2O", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 20}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 20 + } + }, + "restored_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@@H]2O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000230", + "op_type": "flip_chirality", + "image_path": "images/000230.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@:5]1([C:6]([CH3:7])=[O:8])[C@H:9]([CH3:10])[CH2:11][C@H:12]2[CH:13]3[CH:14]=[C:15]([Cl:16])[C:17]4=[CH:18][C:19](=[O:20])[CH2:21][CH2:22][C:23]4([CH3:24])[C@@H:25]3[CH2:26][CH2:27][C:28]12[CH3:29]", + "correct_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3C=C(Cl)C4=CC(=O)CCC4(C)[C@H]3CCC21C", + "predicted_raw": "{\"type\": \"ChangeBond\", \"bond\": {\"atom1\": {\"map_num\": 14}, \"atom2\": {\"map_num\": 15}}, \"order\": \"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 14 + }, + "atom2": { + "map_num": 15 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3CC(Cl)C4=CC(=O)CCC4(C)[C@@H]3CCC21C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000232", + "op_type": "flip_chirality", + "image_path": "images/000232.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]1[O:9][c:10]1[cH:11][c:12]3[c:13]([cH:14][c:15]1[O:16][CH3:17])[CH2:18][CH2:19][N+:20]([CH3:21])([CH3:22])[C@@H:23]3[CH2:24][c:25]1[cH:26][cH:27][c:28]([cH:29][cH:30]1)[O:31][c:32]1[c:33]([O:34][CH3:35])[c:36]([O:37][CH3:38])[cH:39][c:40]3[c:41]1[C@@H:42]([CH2:43]2)[N+:44]([CH3:45])([CH3:46])[CH2:47][CH2:48]3", + "correct_smiles": "COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+](C)(C)[C@H]3Cc1ccc(cc1)Oc1c(OC)c(OC)cc3c1[C@@H](C2)[N+](C)(C)CC3", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 23}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 23 + } + }, + "restored_smiles": "COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+](C)(C)[C@H]3Cc1ccc(cc1)Oc1c(OC)c(OC)cc3c1[C@@H](C2)[N+](C)(C)CC3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000221", + "op_type": "swap_substituents", + "image_path": "images/000221.png", + "wrong_smiles_mapped": "[NH2:1][C:2]1=[N:3][CH:4]=[CH:5][c:9]2[cH:8][cH:7][c:6]([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]4[cH:20][c:21]5[n:22][cH:23][cH:24][cH:25][c:26]5[s:27]4)[C:28]3=[O:29])[c:31]1[cH:30]2", + "correct_smiles": "Nc1nccc2ccc(CN3CCC(NS(=O)(=O)c4cc5ncccc5s4)C3=O)cc12", + "predicted_raw": "{\"type\": \"ChangeAtom\", \"atom\": {\"map_num\": 22}, \"element\": \"C\"}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 22 + }, + "element": "C" + }, + "restored_smiles": "NC1=NC=Cc2ccc(CN3CCC(NS(=O)(=O)c4cc5ccccc5s4)C3=O)c1c2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000229", + "op_type": "flip_chirality", + "image_path": "images/000229.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][CH:16]([OH:17])[C@H:18]1[O:19][CH2:20][C@@H:21]([OH:22])[C@H:23]1[OH:24]", + "correct_smiles": "CCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O", + "predicted_raw": " (3)\n\\ (4)\n/ (5)\n\\ (6)\n/ (7)\n\\ (8)\n/ (9)\n\\ (10)\n/ (11)\n\\ (12, C=O)\nLet's count the segments (bonds):\n1-2, 2-3, 3-4, 4-5, 5-6, 6-7, 7-8, 8-9, 9-10, 10-11, 11-12.\nThat's 11 bonds, so 12 carbons.\nWrong SMILES has:\n[CH3:1][CH2:2][CH2:", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000231", + "op_type": "flip_chirality", + "image_path": "images/000231.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C@H:3]1[O:4][C:5](=[O:6])[C@H:7]([CH3:8])[C@@H:9]([O:10][CH:11]2[CH2:12][C:13]([CH3:14])([O:15][CH3:16])[CH:17]([OH:18])[CH:19]([CH3:20])[O:21]2)[CH:22]([CH3:23])[C@@H:24]([O:25][CH:26]2[O:27][CH:28]([CH3:29])[CH2:30][CH:31]([N:32]([CH3:33])[CH3:34])[CH:35]2[OH:36])[C@@:37]([CH3:38])([OH:39])[CH2:40][C@@H:41]([CH3:42])[C:43](=[O:44])[C@H:45]([CH3:46])[C@@H:47]([OH:48])[C@H:49]1[CH3:50]", + "correct_smiles": "CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(C)(OC)C(O)C(C)O2)C(C)[C@@H](OC2OC(C)CC(N(C)C)C2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C", + "predicted_raw": "{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 18}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 18 + } + }, + "restored_smiles": "CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(C)(OC)CC(C)O2)C(C)[C@@H](OC2OC(C)CC(N(C)C)C2O)[C@@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000234", + "op_type": "flip_chirality", + "image_path": "images/000234.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@@H:11]1[CH2:12][C@H:13]([OH:14])[C@@H:15]([CH2:16][O:17][P:18](=[O:19])([OH:20])[OH:21])[O:22]1", + "correct_smiles": "Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 11 + } + }, + "restored_smiles": "Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000236", + "op_type": "flip_chirality", + "image_path": "images/000236.png", + "wrong_smiles_mapped": "[CH3:1][C:2]#[C:3][C@:4]1([OH:5])[CH2:6][CH2:7][C@H:8]2[C@@H:9]3[CH2:10][C@H:11]([CH3:12])[C:13]4=[CH:14][C:15](=[O:16])[CH2:17][CH2:18][C@:19]4([CH3:20])[C@H:21]3[CH2:22][CH2:23][C@@:24]12[CH3:25]", + "correct_smiles": "CC#C[C@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 11}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 11 + } + }, + "restored_smiles": "CC#C[C@]1(O)CC[C@H]2[C@@H]3C[C@@H](C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]21C", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000240", + "op_type": "flip_ez", + "image_path": "images/000240.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000241", + "op_type": "flip_ez", + "image_path": "images/000241.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000233", + "op_type": "flip_chirality", + "image_path": "images/000233.png", + "wrong_smiles_mapped": "[CH3:1][C@@H:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "C[C@H](N)Cc1ccccc1", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 2}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 2 + } + }, + "restored_smiles": "C[C@H](N)Cc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000242", + "op_type": "flip_ez", + "image_path": "images/000242.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000237", + "op_type": "flip_chirality", + "image_path": "images/000237.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[C@H:13]([OH:14])[CH2:15][C@:16]2([CH3:17])[C@@H:18]([c:19]3[cH:20][cH:21][c:22](=[O:23])[o:24][cH:25]3)[CH2:26][CH2:27][C@:28]12[OH:29]", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2[C@H](O)C[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "predicted_raw": "```json\n{\"type\": \"RemoveAtom\", \"atom\": {\"map_num\": 14}}\n```", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "C[C@]12CC[C@H](O)C[C@@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000239", + "op_type": "flip_chirality", + "image_path": "images/000239.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@H:11]1[O:12][C@H:13]([CH2:14][O:15][P:16](=[O:17])([OH:18])[OH:19])[C@@H:20]([OH:21])[C@H:22]1[OH:23]", + "correct_smiles": "Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O", + "predicted_raw": "0.866, 0).\nOH at (0, -1, 1) (solid wedge, pointing down-left in 2D, but UP in 3D).\nH at (0, -1, -1) (dashed wedge, pointing down-left in 2D, but DOWN in 3D).\nWait, usually in Haworth-like or standard 2D projections of ribose:\nC2' is at the bottom left.\nThe bonds to C1' and C3' are in the ring plane.\nThe bond to OH is pointing towards us (solid wedge).\nThe bond to H is pointing away (dashed wedge).\nSo OH is +z, H is -z.\nPriority 1: OH (+", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000235", + "op_type": "flip_chirality", + "image_path": "images/000235.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C@@H:3]1[C@@H:4]([O:5][C@@H:6]2[O:7][C@H:8]([CH3:9])[C@@H:10]([O:11][C@H:12]3[CH2:13][C@@:14]([CH3:15])([OH:16])[C@H:17]([O:18][C:19](=[O:20])[CH2:21][CH:22]([CH3:23])[CH3:24])[C@H:25]([CH3:26])[O:27]3)[C@H:28]([N:29]([CH3:30])[CH3:31])[C@H:32]2[OH:33])[C@@H:34]([CH2:35][CH:36]=[O:37])[CH2:38][C@@H:39]([CH3:40])[C:41](=[O:42])[CH:43]=[CH:44][CH:45]2[O:46][CH:47]2[CH2:48][C@@H:49]([CH3:50])[O:51][C:52](=[O:53])[CH2:54][C@H:55]1[O:56][C:57]([CH3:58])=[O:59]", + "correct_smiles": "CO[C@@H]1[C@@H](O[C@@H]2O[C@H](C)[C@@H](O[C@H]3C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O3)[C@H](N(C)C)[C@H]2O)[C@@H](CC=O)C[C@@H](C)C(=O)C=CC2OC2C[C@@H](C)OC(=O)C[C@H]1OC(C)=O", + "predicted_raw": "5, Ring2 (C2'), O7, H.\nWait, the SMILES string is: `[O:5][C@@H:6]2[O:7]...`\nActually, it's `[O:5]` then `[C@@H:6]`. The neighbors of 6 are: O5 (from left), Ring2 (C32), O7 (forward), H (implicit).\nOrder: O5, C32, O7.\n`@@` means clockwise.\nLooking from H, O5 -> C32 -> O7 is clockwise.\nLet's draw it: C1' is up (beta). O5 is up.\nIf O5 is up, C32 is right-", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000243", + "op_type": "flip_ez", + "image_path": "images/000243.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000244", + "op_type": "flip_ez", + "image_path": "images/000244.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "```json\n{\"type\": \"FlipEZ\"}\n```", + "predicted_action": { + "type": "FlipEZ" + }, + "restored_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000238", + "op_type": "flip_chirality", + "image_path": "images/000238.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@H:5]([CH2:6][C:7](=[O:8])[OH:9])[CH2:10][N+:11]([CH3:12])([CH3:13])[CH3:14]", + "correct_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "predicted_raw": "```json\n{\"type\": \"FlipChirality\", \"atom\": {\"map_num\": 5}}\n```", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 5 + } + }, + "restored_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + } +] \ No newline at end of file diff --git a/data/benchmark_results_gpt54.json b/data/benchmark_results_gpt54.json new file mode 100644 index 0000000000000000000000000000000000000000..3c650ddd4a52ec1746e1520f23d0857ded997e08 --- /dev/null +++ b/data/benchmark_results_gpt54.json @@ -0,0 +1,5525 @@ +[ + { + "id": "000001", + "op_type": "remove_atom", + "image_path": "images/000001.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([O:11][CH3:13])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":11},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 11 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "COc1cc(C(C)(C)C)ccc1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000004", + "op_type": "add_bond", + "image_path": "images/000004.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:12]1.[OH2:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":10},\"group\":\"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 10 + }, + "group": "OH" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1.O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000000", + "op_type": "change_atom_element", + "image_path": "images/000000.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([SH:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":3}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 3 + } + }, + "restored_smiles": "CC(C)c1ccc(O)c(O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000005", + "op_type": "remove_functional_group", + "image_path": "images/000005.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:13])[c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":7},\"group\":\"F\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "F" + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000006", + "op_type": "add_functional_group", + "image_path": "images/000006.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":11},\"group\":\"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 11 + }, + "group": "OH" + }, + "restored_smiles": "CC(C)(C)c1cccc(O)c1O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000007", + "op_type": "move_substituent", + "image_path": "images/000007.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:7]1[cH:6][cH:5][cH:12][c:10]([OH:11])[c:8]1[OH:9]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":11},\"from_atom\":{\"map_num\":10},\"to_atom\":{\"map_num\":12}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 11 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 12 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)cc1O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000003", + "op_type": "remove_bond", + "image_path": "images/000003.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1([CH3:4])[CH2:3][O:9][c:8]2[cH:7][cH:6][c:5]1[cH:12][c:10]2[OH:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":9}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 9 + } + }, + "restored_smiles": "CC(C)(C)c1cccc(O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000008", + "op_type": "swap_substituents", + "image_path": "images/000008.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":9},\"from_atom\":{\"map_num\":8},\"to_atom\":{\"map_num\":12}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 8 + }, + "to_atom": { + "map_num": 12 + } + }, + "restored_smiles": "CC(C)(C)c1cccc(O)c1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000011", + "op_type": "add_atom", + "image_path": "images/000011.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":11},\"atom2\":{\"map_num\":12}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC(CO)Cc1cccc(O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000012", + "op_type": "change_charge", + "image_path": "images/000012.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[OH+:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":12},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 12 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000013", + "op_type": "change_bond_order", + "image_path": "images/000013.png", + "wrong_smiles_mapped": "[NH:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":2}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000002", + "op_type": "add_atom", + "image_path": "images/000002.png", + "wrong_smiles_mapped": "[CH:1]([CH3:2])([CH3:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([OH:10])[cH:11]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":8},\"from_atom\":{\"map_num\":7},\"to_atom\":{\"map_num\":11}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 8 + }, + "from_atom": { + "map_num": 7 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": "CC(C)c1cccc(O)c1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000014", + "op_type": "remove_bond", + "image_path": "images/000014.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:10]1)[O:9]2)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":9},\"element\":\"C\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 9 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "NC(Cc1ccc2c(c1)C2)C(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000010", + "op_type": "remove_atom", + "image_path": "images/000010.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][NH2:14])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":14},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NC(Cc1cccc(OO)c1)C(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000009", + "op_type": "change_atom_element", + "image_path": "images/000009.png", + "wrong_smiles_mapped": "[NH2:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":1},\"from_atom\":{\"map_num\":2},\"to_atom\":{\"map_num\":3}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 1 + }, + "from_atom": { + "map_num": 2 + }, + "to_atom": { + "map_num": 3 + } + }, + "restored_smiles": "NC(NC(=O)O)c1cccc(O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000016", + "op_type": "remove_functional_group", + "image_path": "images/000016.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:14])[c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":7},\"group\":\"F\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "F" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000019", + "op_type": "change_atom_element", + "image_path": "images/000019.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([SH:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":13},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "OH" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='OH' not found at anchor=12" + }, + { + "id": "000017", + "op_type": "add_functional_group", + "image_path": "images/000017.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":8},\"group\":\"OH\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 8 + }, + "group": "OH" + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000020", + "op_type": "remove_atom", + "image_path": "images/000020.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH2:14][OH:21])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":13},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "OH" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='OH' not found at anchor=12" + }, + { + "id": "000021", + "op_type": "add_atom", + "image_path": "images/000021.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":16},\"group\":\"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 16 + }, + "group": "CH3" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "AddGroup failed: group='CH3' anchor=15" + }, + { + "id": "000015", + "op_type": "add_bond", + "image_path": "images/000015.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12].[OH2:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":11},\"atom2\":{\"map_num\":12}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 12 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC(CO)Cc1cccc(O)c1.O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000024", + "op_type": "remove_functional_group", + "image_path": "images/000024.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH3:21])[c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":13},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(C)c3c(ccc4ccccc43)cc2c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000018", + "op_type": "move_substituent", + "image_path": "images/000018.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:10]1[OH:9])[C:11](=[O:12])[OH:13]", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":9},\"from_atom\":{\"map_num\":10},\"to_atom\":{\"map_num\":8}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000026", + "op_type": "move_substituent", + "image_path": "images/000026.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][c:15]([CH3:14])[cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":14},\"from_atom\":{\"map_num\":15},\"to_atom\":{\"map_num\":11}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 15 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 10 C, 5, is greater than permitted" + }, + { + "id": "000023", + "op_type": "add_bond", + "image_path": "images/000023.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"AddBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":5}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "SINGLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (AddBond): Can't kekulize mol. Unkekulized atoms: 1 2 3 5 6 7 8 9 10 11 12 14 15 16 17 18 19" + }, + { + "id": "000025", + "op_type": "add_functional_group", + "image_path": "images/000025.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]3[c:7]([cH:8][cH:9][c:10]4[cH:11][c:12]([CH3:13])[cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":13},\"from_atom\":{\"map_num\":12},\"to_atom\":{\"map_num\":10}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 13 + }, + "from_atom": { + "map_num": 12 + }, + "to_atom": { + "map_num": 10 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 9 C, 5, is greater than permitted" + }, + { + "id": "000027", + "op_type": "swap_substituents", + "image_path": "images/000027.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:20][c:19]2[c:5]3[cH:6][c:7]([c:8]([cH:18]2)[CH:4]=[CH:3]1)-[c:17]1[c:11]([cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[CH:10]=[CH:9]3", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":14},\"from_atom\":{\"map_num\":13},\"to_atom\":{\"map_num\":15}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 13 + }, + "to_atom": { + "map_num": 15 + } + }, + "restored_smiles": "CC1=Cc2cc(c3cc2C=Cc2ccc(C)cc2-3)C=C1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000033", + "op_type": "add_bond", + "image_path": "images/000033.png", + "wrong_smiles_mapped": "[O:1]=[S:2]([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1.[OH2:3]", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":15},\"atom2\":{\"map_num\":16}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 15 + }, + "atom2": { + "map_num": 16 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O.O=S(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000029", + "op_type": "add_atom", + "image_path": "images/000029.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])[OH:33])[cH:34][cH:35][cH:36][c:37]34)[c:38]3[cH:39][cH:40][cH:41][cH:42][c:43]23)[cH:44]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":31},\"atom2\":{\"map_num\":33}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 31 + }, + "atom2": { + "map_num": 33 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=[SH](=O)c1cccc2c(N=Nc3ccc(N=Nc4cccc(S(=O)(=O)O)c4)c4ccccc34)ccc(Nc3ccccc3)c12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000030", + "op_type": "change_charge", + "image_path": "images/000030.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[NH+:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":16},\"atom2\":{\"map_num\":17}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 16 + }, + "atom2": { + "map_num": 17 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N[NH2+]c3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000031", + "op_type": "change_bond_order", + "image_path": "images/000031.png", + "wrong_smiles_mapped": "[OH:1][SH:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":1},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 1 + }, + "group": "OH" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='OH' not found at anchor=0" + }, + { + "id": "000034", + "op_type": "remove_functional_group", + "image_path": "images/000034.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[c:13]([Cl:46])[cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":13},\"group\":\"Cl\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "Cl" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000022", + "op_type": "remove_bond", + "image_path": "images/000022.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]-2[c:7]2[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]24)[cH:18][c:19]3[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":14},\"from_atom\":{\"map_num\":13},\"to_atom\":{\"map_num\":17}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 13 + }, + "to_atom": { + "map_num": 17 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 16 C, 5, is greater than permitted" + }, + { + "id": "000032", + "op_type": "remove_bond", + "image_path": "images/000032.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]3[c:39]4[cH:40][cH:41][cH:42][c:43]([c:44]24)-[c:37]2[cH:36][cH:35][c:30]([S:31](=[O:32])(=[O:33])[OH:34])[c:29]4[c:21]([NH:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:20][cH:19][c:18]([c:38]42)[N:17]=[N:16]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":22},\"from_atom\":{\"map_num\":21},\"to_atom\":{\"map_num\":43}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 22 + }, + "from_atom": { + "map_num": 21 + }, + "to_atom": { + "map_num": 43 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 19 C, 5, is greater than permitted" + }, + { + "id": "000036", + "op_type": "change_atom_element", + "image_path": "images/000036.png", + "wrong_smiles_mapped": "[NH2:1][NH:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":2}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 2 + } + }, + "restored_smiles": "CSSc1ccccc1.N", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000035", + "op_type": "move_substituent", + "image_path": "images/000035.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][C:12]2=[CH:13][CH:14]=[C:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:41]3[cH:40][cH:39][c:44]2[cH:43][cH:42]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":21},\"atom2\":{\"map_num\":29}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 21 + }, + "atom2": { + "map_num": 29 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=NC2=CC=C(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccc2cc3)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000037", + "op_type": "remove_atom", + "image_path": "images/000037.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":11},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 11 + }, + "group": "OH" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000039", + "op_type": "change_bond_order", + "image_path": "images/000039.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[SH:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":4}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000038", + "op_type": "add_atom", + "image_path": "images/000038.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":1},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "NCSSc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000041", + "op_type": "add_bond", + "image_path": "images/000041.png", + "wrong_smiles_mapped": "[CH3:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH3:2]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":1},\"from_atom\":{\"map_num\":2},\"to_atom\":{\"map_num\":3}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 1 + }, + "from_atom": { + "map_num": 2 + }, + "to_atom": { + "map_num": 3 + } + }, + "restored_smiles": "C.NCSSc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + 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"{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":11},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 11 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(C)cc(NC(C)=O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000057", + "op_type": "remove_bond", + "image_path": "images/000057.png", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH:4]2[N:5]=[C:6]12", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":5},\"atom2\":{\"map_num\":6}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "C1=CC2NC2N1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000056", + "op_type": "change_bond_order", + "image_path": "images/000056.png", + "wrong_smiles_mapped": "[C:1]1=[CH:2][NH:3][CH2:4][N:5]=[C:6]=1", + "correct_smiles": "C1=CNCN=C1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":5},\"atom2\":{\"map_num\":6}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "C1=CNCNC=1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000063", + "op_type": "change_bond_order", + "image_path": "images/000063.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": 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"remove_functional_group", + "image_path": "images/000066.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[OH:25]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":2},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "OH" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000065", + "op_type": "add_bond", + "image_path": "images/000065.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH2:20])[cH:24]1.[CH:21]([CH3:22])=[O:23]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":11},\"atom2\":{\"map_num\":13}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 13 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC=O.CCCCCCCCCCN(C)c1cc(N)cc(CO)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000068", + "op_type": "move_substituent", + "image_path": "images/000068.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][cH:15][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]1[CH2:16][OH:17]", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":16},\"from_atom\":{\"map_num\":24},\"to_atom\":{\"map_num\":18}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 16 + }, + "from_atom": { + "map_num": 24 + }, + "to_atom": { + "map_num": 18 + } + }, + "restored_smiles": "CCCCCCCCCCN(C)c1ccc(CO)c(NC(C)=O)c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000069", + "op_type": "change_atom_element", + "image_path": "images/000069.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][O:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":11}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 11 + } + }, + "restored_smiles": "CC1(CCNCCCC(=O)c2ccc(F)cc2)C(=O)NCN1c1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000067", + "op_type": "add_functional_group", + "image_path": "images/000067.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":11},\"atom2\":{\"map_num\":13}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 11 + }, + "atom2": { + "map_num": 13 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCN(C)c1cc(C)cc(NC(C)=O)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000070", + "op_type": "remove_atom", + "image_path": "images/000070.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH:7]([OH:30])[CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":7},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "OH" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000074", + "op_type": "remove_bond", + "image_path": "images/000074.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][C:9]3([CH:10]1[CH2:11]2)[C:12](=[O:13])[NH:14][CH2:15][N:16]3[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":3}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + } + }, + "restored_smiles": "O=C1NCN(c2ccccc2)C12CCN1CCCC2C1.O=Cc1ccc(F)cc1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000071", + "op_type": "add_atom", + "image_path": "images/000071.png", + "wrong_smiles_mapped": "[CH2:1]([CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[C:11](=[O:12])[NH:13][CH2:14][N:15]2[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":22}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 22 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Can't kekulize mol. Unkekulized atoms: 22 23 24 26 27" + }, + { + "id": "000075", + "op_type": "add_bond", + "image_path": "images/000075.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[O:1]=[CH:2][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":2}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + } + }, + "restored_smiles": "CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1.Cc1ccc(F)cc1.O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000072", + "op_type": "change_charge", + "image_path": "images/000072.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][NH+:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":6},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000073", + "op_type": "change_bond_order", + "image_path": "images/000073.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":4}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000076", + "op_type": "remove_functional_group", + "image_path": "images/000076.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:30])[cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":30}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 30 + } + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000080", + "op_type": "remove_atom", + "image_path": "images/000080.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH:22]([OH:31])[O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":22},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 22 + }, + "group": "OH" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000078", + "op_type": "move_substituent", + "image_path": "images/000078.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][c:25]([F:27])[cH:26][cH:28][cH:29]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":25},\"atom2\":{\"map_num\":27}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 25 + }, + "atom2": { + "map_num": 27 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1cccc(F)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000077", + "op_type": "add_functional_group", + "image_path": "images/000077.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":27},\"group\":\"F\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 27 + }, + "group": "F" + }, + "restored_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1cccc(F)c1", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000081", + "op_type": "add_atom", + "image_path": "images/000081.png", + "wrong_smiles_mapped": "[OH:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([O:7][CH3:8])[c:9]1[O:10][CH3:11])-[c:12]1[cH:13][c:14]3[c:15]([cH:16][c:17]1[C:18](=[O:19])[CH:20]1[CH2:21][O:22][C:23](=[O:24])[CH:25]1[CH2:26]2)[O:27][CH2:28][O:29]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":2},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "OH" + }, + "restored_smiles": "COc1[c]cc2c(c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000082", + "op_type": "change_charge", + "image_path": "images/000082.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[OH+:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":24},\"atom2\":{\"map_num\":25}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 24 + }, + "atom2": { + "map_num": 25 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=[OH+])C1C2)OCO3", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000083", + "op_type": "change_bond_order", + "image_path": "images/000083.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[CH:19]([OH:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":19},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 19 + }, + "group": "OH" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1CC1COC(=O)C1C2)OCO3", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000079", + "op_type": "change_atom_element", + "image_path": "images/000079.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][S:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":23}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 23 + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C(C)C(C=O)C2)OCO3", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000084", + "op_type": "remove_bond", + "image_path": "images/000084.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([c:17]4[c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[C:26]41[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":17},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 17 + }, + "group": "CH3" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='CH3' not found at anchor=16" + }, + { + "id": "000087", + "op_type": "move_substituent", + "image_path": "images/000087.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:26]1([CH2:21][CH2:22][O:23][C:24]1=[O:25])[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":18},\"atom2\":{\"map_num\":19}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 18 + }, + "atom2": { + "map_num": 19 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 18 C, 5, is greater than permitted" + }, + { + "id": "000086", + "op_type": "remove_functional_group", + "image_path": "images/000086.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:21]1([NH2:31])[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":19},\"group\":\"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 19 + }, + "group": "NH2" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='NH2' not found at anchor=18" + }, + { + "id": "000085", + "op_type": "add_bond", + "image_path": "images/000085.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3.[OH:8][CH3:9]", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":8},\"atom2\":{\"map_num\":9}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "C.COc1cc2c(cc1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3.O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000088", + "op_type": "change_atom_element", + "image_path": "images/000088.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([NH:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":18},\"group\":\"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 18 + }, + "group": "NH2" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='NH2' not found at anchor=17" + }, + { + "id": "000089", + "op_type": "remove_atom", + "image_path": "images/000089.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH:27]([CH3:31])[CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":19},\"atom2\":{\"map_num\":20}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 19 + }, + "atom2": { + "map_num": 20 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC1CN(C(c2ccc(F)cc2)c2ccc(F)cc2)CCN1CCCc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000090", + "op_type": "add_atom", + "image_path": "images/000090.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":17},\"atom2\":{\"map_num\":18}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 17 + }, + "atom2": { + "map_num": 18 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccccc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000091", + "op_type": "change_charge", + "image_path": "images/000091.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[NH+:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":14},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 14 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000093", + "op_type": "remove_bond", + "image_path": "images/000093.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]2[cH:29][c:30]1[CH:16]1[CH2:15][N:14]([CH:6]2[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[CH2:28][CH2:27][N:17]1[CH2:18][CH:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":19},\"atom2\":{\"map_num\":20}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 19 + }, + "atom2": { + "map_num": 20 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C2c3ccc(F)c(c3)C3CN2CCN3CCCc2ccccc2)cc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000092", + "op_type": "change_bond_order", + "image_path": "images/000092.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH:15]=[CH:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":15},\"atom2\":{\"map_num\":16}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 15 + }, + "atom2": { + "map_num": 16 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000096", + "op_type": "add_functional_group", + "image_path": "images/000096.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":17},\"atom2\":{\"map_num\":18}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 17 + }, + "atom2": { + "map_num": 18 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccccc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000094", + "op_type": "add_bond", + "image_path": "images/000094.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1.[cH:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"AddBond\",\"bond\":{\"atom1\":{\"map_num\":10},\"atom2\":{\"map_num\":19}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 19 + } + }, + "order": "SINGLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (AddBond): Can't kekulize mol. Unkekulized atoms: 23 24 25 28 29" + }, + { + "id": "000095", + "op_type": "remove_functional_group", + "image_path": "images/000095.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)([N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[CH3:31])[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":31}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000097", + "op_type": "move_substituent", + "image_path": "images/000097.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:9]2[cH:8][cH:7][cH:13][cH:12][c:10]2[F:11])[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":19},\"atom2\":{\"map_num\":20}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 19 + }, + "atom2": { + "map_num": 20 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccccc2F)N2CCN(CCCc3ccccc3)CC2)cc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000098", + "op_type": "change_atom_element", + "image_path": "images/000098.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[S:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":9},\"atom2\":{\"map_num\":10}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 9 + }, + "atom2": { + "map_num": 10 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCOP(=O)(OCC)SN1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000099", + "op_type": "remove_atom", + "image_path": "images/000099.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH2:8][CH3:25])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":6},\"atom2\":{\"map_num\":7}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 5 O, 3, is greater than permitted" + }, + { + "id": "000100", + "op_type": "add_atom", + "image_path": "images/000100.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4]([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":5}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 4 O, 3, is greater than permitted" + }, + { + "id": "000101", + "op_type": "change_charge", + "image_path": "images/000101.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][OH+:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":3},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000102", + "op_type": "change_bond_order", + "image_path": "images/000102.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4]([OH:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":5}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000103", + "op_type": "remove_bond", + "image_path": "images/000103.png", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]2[C:11](=[O:12])[c:13]3[c:14]1[cH:15][cH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([c:22]31)[C:23]2=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":2}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCOP1(=O)OCCc2ccc3cccc4c3c2C(=O)N(O1)C4=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000106", + "op_type": "add_functional_group", + "image_path": "images/000106.png", + "wrong_smiles_mapped": "[CH3:1][O:2][P:3](=[O:4])([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"AddAtom\",\"anchor\":{\"map_num\":6},\"element\":\"C\",\"bond_order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 6 + }, + "element": "C", + "bond_order": "SINGLE" + }, + "restored_smiles": "COP(=O)(OC(C)C)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000104", + "op_type": "add_bond", + "image_path": "images/000104.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4](=[O:5])[O:6][CH2:7][CH3:8].[OH:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":10},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 10 + }, + "group": "OH" + }, + "restored_smiles": "CCO[PH](=O)OCC.O=C1[N]C(=O)c2cccc3cccc1c23", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000107", + "op_type": "move_substituent", + "image_path": "images/000107.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][n:10]1[c:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][c:17]([cH:22]2)[CH:18]=[CH:19][CH:20]=[c:21]3[c:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":10},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 10 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "CCOP(=O)(OCC)On1c(=O)c2c3cc(cc(c3)c1=O)C=CC=2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000108", + "op_type": "swap_substituents", + "image_path": "images/000108.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][C:22]1=[C:13]2[C:11](=[O:12])[N:10]3[C:17](=[CH:16][CH:15]=[CH:14]2)[CH:18]=[CH:19][CH:20]=[C:21]1[C:23]3=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":17},\"atom2\":{\"map_num\":23}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 17 + }, + "atom2": { + "map_num": 23 + } + }, + "order": "SINGLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "No bond between atom idx 14 and 22" + }, + { + "id": "000109", + "op_type": "change_atom_element", + "image_path": "images/000109.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":40},\"atom2\":{\"map_num\":42}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 40 + }, + "atom2": { + "map_num": 42 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCSCCCCCC)COC1OC(CS(=O)(=O)O)C(O)C(O)C1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000105", + "op_type": "remove_functional_group", + "image_path": "images/000105.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][c:15]([Cl:25])[cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":15},\"group\":\"Cl\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 15 + }, + "group": "Cl" + }, + "restored_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000112", + "op_type": "change_charge", + "image_path": "images/000112.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[OH+:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":26},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 26 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000110", + "op_type": "remove_atom", + "image_path": "images/000110.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[C:35]([OH:36])([CH3:57])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":57}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 57 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000114", + "op_type": "remove_bond", + "image_path": "images/000114.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":29},\"atom2\":{\"map_num\":32}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 29 + }, + "atom2": { + "map_num": 32 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 28 S, 7, is greater than permitted" + }, + { + "id": "000115", + "op_type": "add_bond", + "image_path": "images/000115.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":29}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 29 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCC(=O)OC(COC=O)COC1OC(C)C(O)C(O)C1O.CCCCCCCCCCCCCCCCC.O.O.O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000111", + "op_type": "add_atom", + "image_path": "images/000111.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][SH:29](=[O:30])=[O:31])[CH:32]([OH:33])[CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":29},\"element\":\"S\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 29 + }, + "element": "S", + "charge": 0 + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(C[SH](=O)=O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000113", + "op_type": "change_bond_order", + "image_path": "images/000113.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":29},\"atom2\":{\"map_num\":32}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 29 + }, + "atom2": { + "map_num": 32 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 28 S, 7, is greater than permitted" + }, + { + "id": "000121", + "op_type": "remove_atom", + "image_path": "images/000121.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[CH3:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":1},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000118", + "op_type": "move_substituent", + "image_path": "images/000118.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][C:25]1([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH2:27][CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":29},\"atom2\":{\"map_num\":32}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 29 + }, + "atom2": { + "map_num": 32 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 26 S, 7, is greater than permitted" + }, + { + "id": "000116", + "op_type": "remove_functional_group", + "image_path": "images/000116.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[Br:57]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":57}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 57 + } + }, + "restored_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000117", + "op_type": "add_functional_group", + "image_path": "images/000117.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH2:33][CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":29},\"atom2\":{\"map_num\":32}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 29 + }, + "atom2": { + "map_num": 32 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 28 S, 7, is greater than permitted" + }, + { + "id": "000122", + "op_type": "add_atom", + "image_path": "images/000122.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"AddBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":5}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "SINGLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Bond already exists between atoms 2 and 4" + }, + { + "id": "000119", + "op_type": "swap_substituents", + "image_path": "images/000119.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:35]1[CH:33]([OH:34])[CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH:25]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":29},\"atom2\":{\"map_num\":32}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 29 + }, + "atom2": { + "map_num": 32 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 29 S, 7, is greater than permitted" + }, + { + "id": "000120", + "op_type": "change_atom_element", + "image_path": "images/000120.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[N:4]([OH:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":5},\"element\":\"C\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 5 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000123", + "op_type": "change_charge", + "image_path": "images/000123.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[OH+:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":3},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 3 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000124", + "op_type": "change_bond_order", + "image_path": "images/000124.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]([OH:3])[N:4]([CH3:5])[NH2:6]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":3}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000125", + "op_type": "remove_bond", + "image_path": "images/000125.png", + "wrong_smiles_mapped": "[CH2:1]1[C:2](=[O:3])[N:4]([NH2:6])[CH2:5]1", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":5}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 5 + } + } + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000127", + "op_type": "remove_functional_group", + "image_path": "images/000127.png", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[NH2:7]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":1},\"group\":\"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 1 + }, + "group": "NH2" + }, + "restored_smiles": "CC(=O)N(C)N", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000126", + "op_type": "add_bond", + "image_path": "images/000126.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][N:4]([CH3:5])[NH2:6].[OH2:3]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":4}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 2 N, 4, is greater than permitted" + }, + { + "id": "000128", + "op_type": "add_functional_group", + "image_path": "images/000128.png", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "correct_smiles": "CC(=O)N(C)N", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":5}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(N)C=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000129", + "op_type": "change_atom_element", + "image_path": "images/000129.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[N:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":20},\"atom2\":{\"map_num\":2}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 20 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1N5[C@H]2[C@H]3C[C@H]46", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000132", + "op_type": "change_charge", + "image_path": "images/000132.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":2}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 2 + } + }, + "order": "SINGLE" + }, + "restored_smiles": 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"exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 3 C, 5, is greater than permitted" + }, + { + "id": "000155", + "op_type": "remove_atom", + "image_path": "images/000155.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([CH3:14])[cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":9},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 9 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(C)c(C)ccc2c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000157", + "op_type": "remove_bond", + "image_path": "images/000157.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[cH:7][c:8]-3[c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":10},\"from_atom\":{\"map_num\":9},\"to_atom\":{\"map_num\":8}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 9 + }, + "to_atom": { + "map_num": 8 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 7 C, 5, is greater than permitted" + }, + { + "id": "000159", + "op_type": "remove_functional_group", + "image_path": "images/000159.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]([Cl:14])[c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":14}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 14 + } + }, + "restored_smiles": "Cc1ccc2cccc(C)c2c1C", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000160", + "op_type": "add_functional_group", + "image_path": "images/000160.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":9},\"from_atom\":{\"map_num\":8},\"to_atom\":{\"map_num\":3}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 9 + }, + "from_atom": { + "map_num": 8 + }, + "to_atom": { + "map_num": 3 + } + }, + "restored_smiles": "Cc1ccc(C)c2ccccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000158", + "op_type": "add_bond", + "image_path": "images/000158.png", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\":\"AddBond\",\"bond\":{\"atom1\":{\"map_num\":1},\"atom2\":{\"map_num\":5}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 1 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "SINGLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (AddBond): Can't kekulize mol. Unkekulized atoms: 1 2 3 5 6 7 8 10 11" + }, + { + "id": "000162", + "op_type": "change_atom_element", + "image_path": "images/000162.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":2},\"group\":\"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "NH2" + }, + "restored_smiles": "[CH2]C=C(C)C=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000161", + "op_type": "move_substituent", + "image_path": "images/000161.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[C:12]([CH3:13])[c:11]2[cH:5][cH:6][cH:7][c:8]([c:9]2[CH3:10])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":8},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 8 + }, + "group": "CH3" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='CH3' not found at anchor=8" + }, + { + "id": "000164", + "op_type": "add_atom", + "image_path": "images/000164.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[CH:4][CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":5},\"atom2\":{\"map_num\":6}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCC=CC=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000163", + "op_type": "remove_atom", + "image_path": "images/000163.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[CH3:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":6},\"atom2\":{\"map_num\":7}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCC(C)=C(C)CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000166", + "op_type": "change_bond_order", + "image_path": "images/000166.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH:6]=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":6}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCCC(C)=C=O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000167", + "op_type": "remove_bond", + "image_path": "images/000167.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]1[CH:3]=[C:4]([CH3:5])[C:6]1=[O:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":6},\"atom2\":{\"map_num\":2}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 2 + } + } + }, + "restored_smiles": "CCC=C(C)C=O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000168", + "op_type": "add_bond", + "image_path": "images/000168.png", + "wrong_smiles_mapped": "[CH2:3]=[C:4]([CH3:5])[CH:6]=[O:7].[CH3:1][CH3:2]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":5},\"from_atom\":{\"map_num\":4},\"to_atom\":{\"map_num\":6}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 5 + }, + "from_atom": { + "map_num": 4 + }, + "to_atom": { + "map_num": 6 + } + }, + "restored_smiles": "C=CC(C)=O.CC", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000170", + "op_type": "add_functional_group", + "image_path": "images/000170.png", + "wrong_smiles_mapped": "[CH3:1][CH:2]=[C:3]([CH3:4])[CH:5]=[O:6]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":5},\"atom2\":{\"map_num\":6}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 6 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC=C(C)CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000169", + "op_type": "remove_functional_group", + "image_path": "images/000169.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[Br:8]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":8}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 8 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CCC(Br)=C(C)C=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000165", + "op_type": "change_charge", + "image_path": "images/000165.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[OH+:7]", + "correct_smiles": "CCC=C(C)C=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":6},\"atom2\":{\"map_num\":7}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 6 + }, + "atom2": { + "map_num": 7 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "CCC=C(C)C=[OH+]", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000171", + "op_type": "change_atom_element", + "image_path": "images/000171.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":2},\"group\":\"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "NH2" + }, + "restored_smiles": "O=C1Nc2cc[c]cc2C1=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000172", + "op_type": "remove_atom", + "image_path": "images/000172.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[NH2:13])[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":7},\"group\":\"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "NH2" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000173", + "op_type": "add_atom", + "image_path": "images/000173.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":2},\"group\":\"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1ccc2c(c1)NC(=O)C2=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000174", + "op_type": "change_charge", + "image_path": "images/000174.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[OH+:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":8},\"atom2\":{\"map_num\":9}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 8 + }, + "atom2": { + "map_num": 9 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "Cc1ccc2c(c1)C([OH2+])C(=O)N2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000175", + "op_type": "change_bond_order", + "image_path": "images/000175.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH:10]([OH:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":10},\"atom2\":{\"map_num\":11}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000177", + "op_type": "remove_functional_group", + "image_path": "images/000177.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[c:3]([Cl:13])[cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":3},\"group\":\"Cl\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 3 + }, + "group": "Cl" + }, + "restored_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000178", + "op_type": "add_functional_group", + "image_path": "images/000178.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":3},\"group\":\"CH3\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 3 + }, + "group": "CH3" + }, + "restored_smiles": "Cc1cccc2c1NC(=O)C2=O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000176", + "op_type": "add_bond", + "image_path": "images/000176.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][NH:12]2.[OH2:11]", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":10},\"atom2\":{\"map_num\":11}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "No bond between atom idx 9 and 11" + }, + { + "id": "000180", + "op_type": "swap_substituents", + "image_path": "images/000180.png", + "wrong_smiles_mapped": "[CH3:1][c:5]1[cH:4][cH:3][c:2]2[cH:7][c:6]1[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":1}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 1 + } + }, + "restored_smiles": "O=C1Nc2cccc(c2)C1=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000181", + "op_type": "change_atom_element", + "image_path": "images/000181.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][SH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":6},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 6 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeAtom): Explicit valence for atom # 5 O, 3, is greater than permitted" + }, + { + "id": "000179", + "op_type": "move_substituent", + "image_path": "images/000179.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:7][N:12]2[C:5](=[CH:6][C:8](=[O:9])[C:10]2=[O:11])[CH:4]=[CH:3]1", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":8},\"element\":\"C\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 8 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "CC1=CN2C(=O)C(=O)C=C2C=C1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000183", + "op_type": "change_charge", + "image_path": "images/000183.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[NH+:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":5}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1[NH2+]C2C(O)C(O)C(CO)C2O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000184", + "op_type": "change_bond_order", + "image_path": "images/000184.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][C:6]2=[C:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":7},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 7 + }, + "group": "OH" + }, + "restored_smiles": "CN(C)C1=NC2=CC(O)C(CO)C2O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000185", + "op_type": "remove_bond", + "image_path": "images/000185.png", + "wrong_smiles_mapped": "[CH3:1][N:2]1[CH2:3][C:9]2([OH:10])[CH:7]([OH:8])[CH:6]3[N:5]=[C:4]1[O:15][CH:14]3[CH:11]2[CH2:12][OH:13]", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":9},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 9 + }, + "group": "OH" + }, + "restored_smiles": "CN1CC2C(O)C3N=C1OC3C2CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000182", + "op_type": "add_atom", + "image_path": "images/000182.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH3:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":11},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 11 + }, + "group": "CH3" + }, + "restored_smiles": "CN(C)C1=NC2C(CC(O)C2O)O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000186", + "op_type": "add_bond", + "image_path": "images/000186.png", + "wrong_smiles_mapped": "[CH3:12][OH:13].[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][CH:14]2[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":8},\"from_atom\":{\"map_num\":7},\"to_atom\":{\"map_num\":11}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 8 + }, + "from_atom": { + "map_num": 7 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": "CN(C)C1=NC2CC(O)C(O)C2O1.CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000188", + "op_type": "move_substituent", + "image_path": "images/000188.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][C:14]2([CH2:12][OH:13])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":15}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 15 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2C(O)C(O)CC2(CO)O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000187", + "op_type": "add_functional_group", + "image_path": "images/000187.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH2:7][CH:8]([OH:9])[CH:10]([CH2:11][OH:12])[CH:13]2[O:14]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":14}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 14 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1=NC2CC(O)C(CO)C2O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000190", + "op_type": "change_charge", + "image_path": "images/000190.png", + "wrong_smiles_mapped": "[OH+:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":1},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000189", + "op_type": "swap_substituents", + "image_path": "images/000189.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[CH:14]1[CH:6]2[N:5]=[C:4]([CH:11]([CH2:12][OH:13])[CH:9]([OH:10])[CH:7]2[OH:8])[O:15]1", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":15}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 15 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CN(C)C1OC2=NC1C(O)C(O)C2CO", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000191", + "op_type": "change_bond_order", + "image_path": "images/000191.png", + "wrong_smiles_mapped": "[OH:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":2},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "OH" + }, + "restored_smiles": "O=C(O)c1cccc([CH]O)c1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000192", + "op_type": "add_functional_group", + "image_path": "images/000192.png", + "wrong_smiles_mapped": "[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]1[OH:12]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":2},\"group\":\"CHO\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "CHO" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='CHO' not found at anchor=1" + }, + { + "id": "000193", + "op_type": "move_substituent", + "image_path": "images/000193.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[c:5]([C:9](=[O:10])[OH:11])[cH:6][cH:7][cH:8][c:12]1[OH:13]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":13},\"from_atom\":{\"map_num\":12},\"to_atom\":{\"map_num\":7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 13 + }, + "from_atom": { + "map_num": 12 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "O=C(O)c1ccc(O)cc1C(=O)O", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000194", + "op_type": "swap_substituents", + "image_path": "images/000194.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:13])[c:12]1[C:9](=[O:10])[OH:11]", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":13},\"from_atom\":{\"map_num\":8},\"to_atom\":{\"map_num\":7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 13 + }, + "from_atom": { + "map_num": 8 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "O=C(O)c1ccc(O)cc1C(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000199", + "op_type": "move_substituent", + "image_path": "images/000199.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][c:15]([Cl:14])[cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":14},\"from_atom\":{\"map_num\":15},\"to_atom\":{\"map_num\":17}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 14 + }, + "from_atom": { + "map_num": 15 + }, + "to_atom": { + "map_num": 17 + } + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2cccc(Cl)c12", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000198", + "op_type": "add_functional_group", + "image_path": "images/000198.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\":\"AddGroup\",\"anchor\":{\"map_num\":2},\"group\":\"NH2\"}", + "predicted_action": { + "type": "AddGroup", + "anchor": { + "map_num": 2 + }, + "group": "NH2" + }, + "restored_smiles": "CC(N)NS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000195", + "op_type": "add_functional_group", + "image_path": "images/000195.png", + "wrong_smiles_mapped": "[cH:1]1[n:2][c:3]([Cl:4])[n:5][c:6]([C:7]([Cl:8])([Cl:9])[Cl:10])[n:11]1", + "correct_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":4},\"from_atom\":{\"map_num\":3},\"to_atom\":{\"map_num\":1}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 4 + }, + "from_atom": { + "map_num": 3 + }, + "to_atom": { + "map_num": 1 + } + }, + "restored_smiles": "Clc1ncnc(C(Cl)(Cl)Cl)n1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000200", + "op_type": "change_charge", + "image_path": "images/000200.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[OH+:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":41},\"atom2\":{\"map_num\":43}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 41 + }, + "atom2": { + "map_num": 43 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=[OH+]", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000197", + "op_type": "change_bond_order", + "image_path": "images/000197.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]=[CH:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":3}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000201", + "op_type": "change_bond_order", + "image_path": "images/000201.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][CH:41]([CH3:42])[OH:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":41},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 41 + }, + "group": "OH" + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OCC", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000196", + "op_type": "change_charge", + "image_path": "images/000196.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[OH+:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":7},\"element\":\"O\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 7 + }, + "element": "O", + "charge": 0 + }, + "restored_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000203", + "op_type": "swap_substituents", + "image_path": "images/000203.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:23]1([CH3:8])[CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[CH2:11][CH:9]([CH3:10])[C:7]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]21)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[O:43]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":24},\"atom2\":{\"map_num\":25}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 24 + }, + "atom2": { + "map_num": 25 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "C=CC(C)=CCC1(C)C(OC(=O)c2ccc(O)cc2)CC(C)C23C(OC(C)=O)OC(OC(C)=O)C2CC(OC(C)=O)CC13", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000202", + "op_type": "move_substituent", + "image_path": "images/000202.png", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:26]2([O:27][C:28]([CH3:29])=[O:30])[CH:25]=[C:24]3[CH:23]([CH:32]1[CH2:31]2)[CH:39]([O:40][C:41]([CH3:42])=[O:43])[O:38][CH:33]3[O:34][C:35]([CH3:36])=[O:37]", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":12},\"atom2\":{\"map_num\":26}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 12 + }, + "atom2": { + "map_num": 26 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Explicit valence for atom # 22 C, 5, is greater than permitted" + }, + { + "id": "000204", + "op_type": "change_charge", + "image_path": "images/000204.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][C:4](=[OH+:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":5}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=C1NC(=[OH+])C(Br)=C1Br", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000205", + "op_type": "change_bond_order", + "image_path": "images/000205.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][CH:4]([OH:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":4},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 4 + }, + "group": "OH" + }, + "restored_smiles": "O=C1NCC(Br)=C1Br", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000206", + "op_type": "move_substituent", + "image_path": "images/000206.png", + "wrong_smiles_mapped": "[O:1]=[C:2]1[N:3]([Br:9])[C:4](=[O:5])[C:6]([Br:7])=[CH:8]1", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":9}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 9 + } + } + }, + "restored_smiles": "Br.O=C1C=C(Br)C(=O)N1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000208", + "op_type": "move_substituent", + "image_path": "images/000208.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:18]2[O:16][CH3:17])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":29},\"atom2\":{\"map_num\":30}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 29 + }, + "atom2": { + "map_num": 30 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Can't kekulize mol. Unkekulized atoms: 24 25 26 27 29" + }, + { + "id": "000211", + "op_type": "swap_substituents", + "image_path": "images/000211.png", + "wrong_smiles_mapped": "[CH3:1][NH:2][C:3](=[O:4])[CH:26]1[CH:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([NH2:19])[cH:20][cH:21]4)[n:22][cH:23][n:24][c:25]23)[O:6][CH:5]([OH:27])[CH:28]1[OH:29]", + "correct_smiles": "CNC(=O)C1OC(n2cnc3c(NCc4ccc(N)cc4)ncnc32)C(O)C1O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":18},\"group\":\"NH2\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 18 + }, + "group": "NH2" + }, + "restored_smiles": "CNC(=O)C1C(O)C(O)OC1n1cnc2c(NCc3ccccc3)ncnc21", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000210", + "op_type": "swap_substituents", + "image_path": "images/000210.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:13]1[c:7]([CH3:14])[cH:8][cH:9][c:10]([Cl:11])[cH:12]1", + "correct_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":6},\"from_atom\":{\"map_num\":13},\"to_atom\":{\"map_num\":10}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 6 + }, + "from_atom": { + "map_num": 13 + }, + "to_atom": { + "map_num": 10 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 11 C, 5, is greater than permitted" + }, + { + "id": "000207", + "op_type": "change_charge", + "image_path": "images/000207.png", + "wrong_smiles_mapped": "[CH3:1][OH+:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":1}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 1 + } + }, + "restored_smiles": "COc1cc(-c2c(C(=O)[OH2+])n(-c3ccc(N)cc3)c(=O)c3cc(OCc4ccccn4)ccc23)cc(OC)c1OC", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000209", + "op_type": "swap_substituents", + "image_path": "images/000209.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:6]1[c:5](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[n:35](-[c:36]2[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]2)[c:33](=[O:34])[c:32]2[c:19]1[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][n:30]1)[cH:31]2", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":29},\"atom2\":{\"map_num\":30}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 29 + }, + "atom2": { + "map_num": 30 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Can't kekulize mol. Unkekulized atoms: 35 36 37 38 40" + }, + { + "id": "000213", + "op_type": "swap_substituents", + "image_path": "images/000213.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[n:3][cH:4][c:5]([CH2:6][c:26]2[n+:7]([CH3:27])[cH:8][s:9][c:10]2[CH2:11][CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:18](=[O:19])([OH:20])[O:21][P:22](=[O:23])([O-:24])[OH:25])[c:28]([NH2:29])[n:30]1", + "correct_smiles": "Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)c2C)c(N)n1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":3}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "Cc1ncc(Cc2c(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)sc[n+]2C)c(N)n1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000212", + "op_type": "swap_substituents", + "image_path": "images/000212.png", + "wrong_smiles_mapped": "[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([CH2:10][CH2:11][Cl:12])[n:7][cH:8][n:9]2[n:13]([CH3:14])[c:15]1=[O:16]", + "correct_smiles": "Cn1c(=O)c2c(ncn2CCCl)n(C)c1=O", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":10},\"from_atom\":{\"map_num\":6},\"to_atom\":{\"map_num\":2}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 6 + }, + "to_atom": { + "map_num": 2 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (MoveSubstituent): Explicit valence for atom # 1 N, 4, is greater than permitted" + }, + { + "id": "000215", + "op_type": "swap_substituents", + "image_path": "images/000215.png", + "wrong_smiles_mapped": "[CH3:1][C:8]12[C:2]([CH3:9])([CH3:10])[CH:3]=[CH:4][CH:5]1[CH2:6][CH2:7]2", + "correct_smiles": "CC12C=CC(CC1)C2(C)C", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":4}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "CC1(C)CCC2CCC21C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000214", + "op_type": "swap_substituents", + "image_path": "images/000214.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([Cl:3])[c:6]1[cH:5][c:4]([Cl:7])[c:10]([Cl:11])[cH:9][cH:8]1", + "correct_smiles": "O=C(Cl)c1cc(Cl)ccc1Cl", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":11}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 11 + } + }, + "restored_smiles": "O=C(Cl)c1cccc(Cl)c1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000219", + "op_type": "swap_substituents", + "image_path": "images/000219.png", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([F:18])[cH:16][c:17]1[N:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1", + "correct_smiles": "CN(C)c1ccc(N=Nc2ccccc2)cc1F", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":18},\"from_atom\":{\"map_num\":7},\"to_atom\":{\"map_num\":16}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 18 + }, + "from_atom": { + "map_num": 7 + }, + "to_atom": { + "map_num": 16 + } + }, + "restored_smiles": "CN(C)c1cccc(F)c1N=Nc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000218", + "op_type": "swap_substituents", + "image_path": "images/000218.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[c:11]([CH2:12][CH2:13][N:14]([CH3:15])[CH3:16])[cH:17][c:18]3[c:19]([c:20]2[O:21][CH3:22])[O:23][CH2:24][O:25]3)[c:26]([O:31][CH3:32])[c:30]1[C:27](=[O:28])[OH:29]", + "correct_smiles": "COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(C(=O)O)c1OC", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":3},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 3 + }, + "group": "CH3" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='CH3' not found at anchor=2" + }, + { + "id": "000217", + "op_type": "flip_chirality", + "image_path": "images/000217.png", + "wrong_smiles_mapped": 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"[CH3:1][CH2:2][O:3][P:4](=[S:5])([O:6][CH2:7][CH3:8])[O:9][c:12]1[cH:11][c:10]([CH3:13])[n:15][nH:14]1", + "correct_smiles": "CCOP(=S)(OCC)Oc1cc(C)[nH]n1", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":13},\"from_atom\":{\"map_num\":10},\"to_atom\":{\"map_num\":14}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 13 + }, + "from_atom": { + "map_num": 10 + }, + "to_atom": { + "map_num": 14 + } + }, + "restored_smiles": "CCOP(=S)(OCC)Oc1ccnn1C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000221", + "op_type": "swap_substituents", + "image_path": "images/000221.png", + "wrong_smiles_mapped": "[NH2:1][C:2]1=[N:3][CH:4]=[CH:5][c:9]2[cH:8][cH:7][c:6]([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]4[cH:20][c:21]5[n:22][cH:23][cH:24][cH:25][c:26]5[s:27]4)[C:28]3=[O:29])[c:31]1[cH:30]2", + "correct_smiles": "Nc1nccc2ccc(CN3CCC(NS(=O)(=O)c4cc5ncccc5s4)C3=O)cc12", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":3}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NC1NC=Cc2ccc(CN3CCC(NS(=O)(=O)c4cc5ncccc5s4)C3=O)c1c2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000222", + "op_type": "flip_chirality", + "image_path": "images/000222.png", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([c:18]3[cH:19][cH:20][c:21](=[O:22])[o:23][cH:24]3)[CH2:25][CH2:26][C@:27]12[OH:28]", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":27},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 27 + }, + "group": "OH" + }, + "restored_smiles": "C[C@]12CCC3C(CC[C@H]4C[C@@H](O)CC[C@]34C)[C@H]1CC[C@@H]2c1ccc(=O)oc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000223", + "op_type": "flip_chirality", + "image_path": "images/000223.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[C:11]1=[C:12]([CH2:13][C@H:14]([CH3:15])[O:16][C@H:17]1[CH3:18])[C:19]2=[O:20]", + "correct_smiles": "COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C2=O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":14},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 14 + }, + "group": "CH3" + }, + "restored_smiles": "COc1cccc2c1C(=O)C1=C(CCO[C@H]1C)C2=O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000220", + "op_type": "swap_substituents", + "image_path": "images/000220.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([F:13])[c:9]([OH:10])[cH:11][c:12]1[OH:8]", + "correct_smiles": "NCC(O)c1cc(O)c(O)cc1F", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":10},\"from_atom\":{\"map_num\":9},\"to_atom\":{\"map_num\":11}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 10 + }, + "from_atom": { + "map_num": 9 + }, + "to_atom": { + "map_num": 11 + } + }, + "restored_smiles": "NCC(O)c1cc(F)cc(O)c1O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000224", + "op_type": "flip_chirality", + "image_path": "images/000224.png", + "wrong_smiles_mapped": "[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][n:7][c:8]2[c:9]1[n:10][cH:11][n:12]2[C@@H:13]1[O:14][C@@H:15]([CH2:16][OH:17])[C@@H:18]([O:19][P:20](=[O:21])([OH:22])[OH:23])[C@H:24]1[OH:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1", + "correct_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O)c1cccnc1", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":20},\"atom2\":{\"map_num\":22}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 20 + }, + "atom2": { + "map_num": 22 + } + } + }, + "restored_smiles": "O.O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO)[C@@H](O[PH](=O)O)[C@H]1O)c1cccnc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000225", + "op_type": "flip_chirality", + "image_path": "images/000225.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:8][CH2:9][CH:10]1[CH:11]2[CH2:12][CH2:13][C:14]2([CH3:15])[CH:16]1[CH2:17][CH2:18][C@H:19]2[OH:20]", + "correct_smiles": "CC12CCCC[C@@H]1CCC1C2CCC2(C)C1CC[C@@H]2O", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":20},\"from_atom\":{\"map_num\":19},\"to_atom\":{\"map_num\":7}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 20 + }, + "from_atom": { + "map_num": 19 + }, + "to_atom": { + "map_num": 7 + } + }, + "restored_smiles": "CC12CCCC1C1CC[C@@]3(O)CCCCC3(C)C1CC2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000226", + "op_type": "flip_chirality", + "image_path": "images/000226.png", + "wrong_smiles_mapped": "[CH2:1]=[C:2]([CH3:3])[C@H:4]1[CH2:5][c:6]2[c:7]([cH:8][cH:9][c:10]3[c:11]2[O:12][C@H:13]2[CH2:14][O:15][c:16]4[cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24][c:25]4[C@@H:26]2[C:27]3=[O:28])[O:29]1", + "correct_smiles": "C=C(C)[C@H]1Cc2c(ccc3c2O[C@@H]2COc4cc(OC)c(OC)cc4[C@@H]2C3=O)O1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":25},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 25 + }, + "group": "OH" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "RemoveGroup failed: group='OH' not found at anchor=24" + }, + { + "id": "000228", + "op_type": "flip_chirality", + "image_path": "images/000228.png", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH:5]3[c:6]4[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[c:13]4[CH2:14][CH2:15][CH:16]3[CH:17]1[CH2:18][CH2:19][C@H:20]2[OH:21]", + "correct_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@@H]2O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":20},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 20 + }, + "group": "OH" + }, + "restored_smiles": "CC12CCCC1C1CCc3c(ccc(O)c3F)C1CC2", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000227", + "op_type": "flip_chirality", + "image_path": "images/000227.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[NH:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15]", + "correct_smiles": "CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":2},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 2 + }, + "group": "CH3" + }, + "restored_smiles": "C[C](CO)[C@H](O)C(=O)NCCC(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000229", + "op_type": "flip_chirality", + "image_path": "images/000229.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][CH:16]([OH:17])[C@H:18]1[O:19][CH2:20][C@@H:21]([OH:22])[C@H:23]1[OH:24]", + "correct_smiles": "CCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O", + "predicted_raw": "{\"type\":\"FlipChirality\",\"atom\":{\"map_num\":16}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 16 + } + }, + "restored_smiles": null, + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": "Atom idx=15 has no specified chirality to flip" + }, + { + "id": "000232", + "op_type": "flip_chirality", + "image_path": "images/000232.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]1[O:9][c:10]1[cH:11][c:12]3[c:13]([cH:14][c:15]1[O:16][CH3:17])[CH2:18][CH2:19][N+:20]([CH3:21])([CH3:22])[C@@H:23]3[CH2:24][c:25]1[cH:26][cH:27][c:28]([cH:29][cH:30]1)[O:31][c:32]1[c:33]([O:34][CH3:35])[c:36]([O:37][CH3:38])[cH:39][c:40]3[c:41]1[C@@H:42]([CH2:43]2)[N+:44]([CH3:45])([CH3:46])[CH2:47][CH2:48]3", + "correct_smiles": "COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+](C)(C)[C@H]3Cc1ccc(cc1)Oc1c(OC)c(OC)cc3c1[C@@H](C2)[N+](C)(C)CC3", + "predicted_raw": "{\"type\":\"FlipChirality\",\"atom\":{\"map_num\":42}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 42 + } + }, + "restored_smiles": "COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+](C)(C)[C@@H]3Cc1ccc(cc1)Oc1c(OC)c(OC)cc3c1[C@H](C2)[N+](C)(C)CC3", + "exec_match": false, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000231", + "op_type": "flip_chirality", + "image_path": "images/000231.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C@H:3]1[O:4][C:5](=[O:6])[C@H:7]([CH3:8])[C@@H:9]([O:10][CH:11]2[CH2:12][C:13]([CH3:14])([O:15][CH3:16])[CH:17]([OH:18])[CH:19]([CH3:20])[O:21]2)[CH:22]([CH3:23])[C@@H:24]([O:25][CH:26]2[O:27][CH:28]([CH3:29])[CH2:30][CH:31]([N:32]([CH3:33])[CH3:34])[CH:35]2[OH:36])[C@@:37]([CH3:38])([OH:39])[CH2:40][C@@H:41]([CH3:42])[C:43](=[O:44])[C@H:45]([CH3:46])[C@@H:47]([OH:48])[C@H:49]1[CH3:50]", + "correct_smiles": "CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(C)(OC)C(O)C(C)O2)C(C)[C@@H](OC2OC(C)CC(N(C)C)C2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":13},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "CH3" + }, + "restored_smiles": "CC[C@H]1OC(=O)[C@H](C)[C@@H](OC2CC(OC)C(O)C(C)O2)C(C)[C@@H](OC2OC(C)CC(N(C)C)C2O)[C@@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000230", + "op_type": "flip_chirality", + "image_path": "images/000230.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@:5]1([C:6]([CH3:7])=[O:8])[C@H:9]([CH3:10])[CH2:11][C@H:12]2[CH:13]3[CH:14]=[C:15]([Cl:16])[C:17]4=[CH:18][C:19](=[O:20])[CH2:21][CH2:22][C:23]4([CH3:24])[C@@H:25]3[CH2:26][CH2:27][C:28]12[CH3:29]", + "correct_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3C=C(Cl)C4=CC(=O)CCC4(C)[C@H]3CCC21C", + "predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":16},\"from_atom\":{\"map_num\":15},\"to_atom\":{\"map_num\":18}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 16 + }, + "from_atom": { + "map_num": 15 + }, + "to_atom": { + "map_num": 18 + } + }, + "restored_smiles": "CC(=O)O[C@]1(C(C)=O)[C@H](C)C[C@H]2C3C=CC4=C(Cl)C(=O)CCC4(C)[C@@H]3CCC21C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000233", + "op_type": "flip_chirality", + "image_path": "images/000233.png", + "wrong_smiles_mapped": "[CH3:1][C@@H:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "C[C@H](N)Cc1ccccc1", + "predicted_raw": "{\"type\":\"FlipChirality\",\"atom\":{\"map_num\":2}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 2 + } + }, + "restored_smiles": "C[C@H](N)Cc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000234", + "op_type": "flip_chirality", + "image_path": "images/000234.png", + "wrong_smiles_mapped": "[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]1[n:8][cH:9][n:10]2[C@@H:11]1[CH2:12][C@H:13]([OH:14])[C@@H:15]([CH2:16][O:17][P:18](=[O:19])([OH:20])[OH:21])[O:22]1", + "correct_smiles": "Nc1ncnc2c1ncn2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":13},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 13 + }, + "group": "OH" + }, + "restored_smiles": "Nc1ncnc2c1ncn2[C@@H]1CC[C@@H](COP(=O)(O)O)O1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000235", + "op_type": "flip_chirality", + "image_path": "images/000235.png", + "wrong_smiles_mapped": "[CH3:1][O:2][C@@H:3]1[C@@H:4]([O:5][C@@H:6]2[O:7][C@H:8]([CH3:9])[C@@H:10]([O:11][C@H:12]3[CH2:13][C@@:14]([CH3:15])([OH:16])[C@H:17]([O:18][C:19](=[O:20])[CH2:21][CH:22]([CH3:23])[CH3:24])[C@H:25]([CH3:26])[O:27]3)[C@H:28]([N:29]([CH3:30])[CH3:31])[C@H:32]2[OH:33])[C@@H:34]([CH2:35][CH:36]=[O:37])[CH2:38][C@@H:39]([CH3:40])[C:41](=[O:42])[CH:43]=[CH:44][CH:45]2[O:46][CH:47]2[CH2:48][C@@H:49]([CH3:50])[O:51][C:52](=[O:53])[CH2:54][C@H:55]1[O:56][C:57]([CH3:58])=[O:59]", + "correct_smiles": 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"{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":12}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "CC#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]21C", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000238", + "op_type": "flip_chirality", + "image_path": "images/000238.png", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[O:4][C@H:5]([CH2:6][C:7](=[O:8])[OH:9])[CH2:10][N+:11]([CH3:12])([CH3:13])[CH3:14]", + "correct_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "predicted_raw": "{\"type\":\"FlipChirality\",\"atom\":{\"map_num\":5}}", + "predicted_action": { + "type": "FlipChirality", + "atom": { + "map_num": 5 + } + }, + "restored_smiles": "CC(=O)O[C@@H](CC(=O)O)C[N+](C)(C)C", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000239", + "op_type": "flip_chirality", + "image_path": 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"predicted_raw": "{\"type\":\"MoveSubstituent\",\"substituent\":{\"map_num\":6},\"from_atom\":{\"map_num\":5},\"to_atom\":{\"map_num\":4}}", + "predicted_action": { + "type": "MoveSubstituent", + "substituent": { + "map_num": 6 + }, + "from_atom": { + "map_num": 5 + }, + "to_atom": { + "map_num": 4 + } + }, + "restored_smiles": "C/C=C\\C(Cc1cccc2ccccc12)C(=O)O", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000240", + "op_type": "flip_ez", + "image_path": "images/000240.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":5}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "C/C=C\\C=C(C(=O)O)c1cccc2ccccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000242", + "op_type": "flip_ez", + "image_path": "images/000242.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":5}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "C/C=C\\C=C(C(=O)O)c1cccc2ccccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000244", + "op_type": "flip_ez", + "image_path": "images/000244.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":4},\"atom2\":{\"map_num\":5}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 4 + }, + "atom2": { + "map_num": 5 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "C/C=C\\C=C(C(=O)O)c1cccc2ccccc12", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000243", + "op_type": "flip_ez", + "image_path": "images/000243.png", + "wrong_smiles_mapped": "[CH3:1]/[CH:2]=[CH:3]\\[CH2:4][CH:5]([C:6](=[O:7])[OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12", + "correct_smiles": "C/C=C/CC(C(=O)O)c1cccc2ccccc12", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":5},\"atom2\":{\"map_num\":9}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 5 + }, + "atom2": { + "map_num": 9 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": "Sanitization failed (ChangeBond): Can't kekulize mol. Unkekulized atoms: 9 10 11 12 13 14 15 16 17" + }, + { + "id": "000028", + "op_type": "remove_atom", + "image_path": "images/000028.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[OH:46])[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":28},\"group\":\"OH\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 28 + }, + "group": "OH" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000050", + "op_type": "add_bond", + "image_path": "images/000050.png", + "wrong_smiles_mapped": "[CH3:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12].[NH2:1][CH3:2]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "{\"type\":\"RemoveGroup\",\"anchor\":{\"map_num\":1},\"group\":\"CH3\"}", + "predicted_action": { + "type": "RemoveGroup", + "anchor": { + "map_num": 1 + }, + "group": "CH3" + }, + "restored_smiles": "CCNCCSP(=O)(O)O.N", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + } +] \ No newline at end of file diff --git a/data/benchmark_results_gpt55.json b/data/benchmark_results_gpt55.json new file mode 100644 index 0000000000000000000000000000000000000000..188b44253ce62d3d28caa96e4dd30c9de295afd7 --- /dev/null +++ b/data/benchmark_results_gpt55.json @@ -0,0 +1,1901 @@ +[ + { + "id": "000005", + "op_type": "remove_functional_group", + "image_path": "images/000005.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:13])[c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":13}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 13 + } + }, + "restored_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000004", + "op_type": "add_bond", + "image_path": "images/000004.png", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:12]1.[OH2:11]", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "predicted_raw": "{\"type\":\"AddBond\",\"bond\":{\"atom1\":{\"map_num\":10},\"atom2\":{\"map_num\":11}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 10 + }, + "atom2": { + "map_num": 11 + } + }, + "order": "SINGLE" + }, + "restored_smiles": 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null + }, + { + "id": "000027", + "op_type": "swap_substituents", + "image_path": "images/000027.png", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:20][c:19]2[c:5]3[cH:6][c:7]([c:8]([cH:18]2)[CH:4]=[CH:3]1)-[c:17]1[c:11]([cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[CH:10]=[CH:9]3", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000030", + "op_type": "change_charge", + "image_path": "images/000030.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[NH+:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":17},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 17 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000031", + "op_type": "change_bond_order", + "image_path": "images/000031.png", + "wrong_smiles_mapped": "[OH:1][SH:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":4}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000034", + "op_type": "remove_functional_group", + "image_path": "images/000034.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[c:13]([Cl:46])[cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":46}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 46 + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000036", + "op_type": "change_atom_element", + "image_path": "images/000036.png", + "wrong_smiles_mapped": "[NH2:1][NH:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":2},\"element\":\"C\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 2 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000038", + "op_type": "add_atom", + "image_path": "images/000038.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":1},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "NCSSc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000037", + "op_type": "remove_atom", + "image_path": "images/000037.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":12}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000032", + "op_type": "remove_bond", + "image_path": "images/000032.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]3[c:39]4[cH:40][cH:41][cH:42][c:43]([c:44]24)-[c:37]2[cH:36][cH:35][c:30]([S:31](=[O:32])(=[O:33])[OH:34])[c:29]4[c:21]([NH:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:20][cH:19][c:18]([c:38]42)[N:17]=[N:16]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "{\"type\":\"RemoveBond\",\"bond\":{\"atom1\":{\"map_num\":43},\"atom2\":{\"map_num\":37}}}", + "predicted_action": { + "type": "RemoveBond", + "bond": { + "atom1": { + "map_num": 43 + }, + "atom2": { + "map_num": 37 + } + } + }, + "restored_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000039", + "op_type": "change_bond_order", + "image_path": "images/000039.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[SH:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":3},\"atom2\":{\"map_num\":4}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 3 + }, + "atom2": { + "map_num": 4 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000035", + "op_type": "move_substituent", + "image_path": "images/000035.png", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][C:12]2=[CH:13][CH:14]=[C:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:41]3[cH:40][cH:39][c:44]2[cH:43][cH:42]3)[cH:45]1", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "predicted_raw": "", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000026", + "op_type": "move_substituent", + "image_path": "images/000026.png", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][c:15]([CH3:14])[cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "predicted_raw": "", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000043", + "op_type": "add_functional_group", + "image_path": "images/000043.png", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":1},\"element\":\"N\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 1 + }, + "element": "N", + "charge": 0 + }, + "restored_smiles": "NCSSc1ccccc1", + "exec_match": false, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000042", + "op_type": "remove_functional_group", + "image_path": "images/000042.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[Cl:12]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":12}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 12 + } + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000041", + "op_type": "add_bond", + "image_path": "images/000041.png", + "wrong_smiles_mapped": "[CH3:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH3:2]", + "correct_smiles": "NCCSSc1ccccc1", + "predicted_raw": "{\"type\":\"AddBond\",\"bond\":{\"atom1\":{\"map_num\":2},\"atom2\":{\"map_num\":3}},\"order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddBond", + "bond": { + "atom1": { + "map_num": 2 + }, + "atom2": { + "map_num": 3 + } + }, + "order": "SINGLE" + }, + "restored_smiles": "NCCSSc1ccccc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000044", + "op_type": "change_atom_element", + "image_path": "images/000044.png", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][P:9](=[O:10])([OH:11])[OH:12]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":8},\"element\":\"S\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 8 + }, + "element": "S", + "charge": 0 + }, + "restored_smiles": "NCCCNCCSP(=O)(O)O", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000045", + "op_type": "remove_atom", + "image_path": "images/000045.png", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[OH:13]", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + 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"COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":31}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": false, + "parse_error": false, + "exec_error": null + }, + { + "id": "000083", + "op_type": "change_bond_order", + "image_path": "images/000083.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[CH:19]([OH:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "{\"type\":\"ChangeBond\",\"bond\":{\"atom1\":{\"map_num\":19},\"atom2\":{\"map_num\":20}},\"order\":\"DOUBLE\"}", + "predicted_action": { + "type": "ChangeBond", + "bond": { + "atom1": { + "map_num": 19 + }, + "atom2": { + "map_num": 20 + } + }, + "order": "DOUBLE" + }, + "restored_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000088", + "op_type": "change_atom_element", + "image_path": "images/000088.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([NH:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"ChangeAtom\",\"atom\":{\"map_num\":18},\"element\":\"C\",\"charge\":0}", + "predicted_action": { + "type": "ChangeAtom", + "atom": { + "map_num": 18 + }, + "element": "C", + "charge": 0 + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000084", + "op_type": "remove_bond", + "image_path": "images/000084.png", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([c:17]4[c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[C:26]41[CH2:27]2)[O:28][CH2:29][O:30]3", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "predicted_raw": "", + "predicted_action": null, + "restored_smiles": null, + "exec_match": false, + "type_match": false, + "parse_error": true, + "exec_error": null + }, + { + "id": "000090", + "op_type": "add_atom", + "image_path": "images/000090.png", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"AddAtom\",\"anchor\":{\"map_num\":1},\"element\":\"F\",\"bond_order\":\"SINGLE\"}", + "predicted_action": { + "type": "AddAtom", + "anchor": { + "map_num": 1 + }, + "element": "F", + "bond_order": "SINGLE" + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + }, + { + "id": "000089", + "op_type": "remove_atom", + "image_path": "images/000089.png", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH:27]([CH3:31])[CH2:28]2)[cH:29][cH:30]1", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "predicted_raw": "{\"type\":\"RemoveAtom\",\"atom\":{\"map_num\":31}}", + "predicted_action": { + "type": "RemoveAtom", + "atom": { + "map_num": 31 + } + }, + "restored_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "exec_match": true, + "type_match": true, + "parse_error": false, + "exec_error": null + } +] \ No newline at end of file diff --git a/data/benchmark_summary.json b/data/benchmark_summary.json new file mode 100644 index 0000000000000000000000000000000000000000..99ffb252b744d2577a839ba656a38e9fa288a46a --- /dev/null +++ b/data/benchmark_summary.json @@ -0,0 +1,302 @@ +{ + "gpt-5.4": { + "total": 245, + "exec_match": 63, + "type_match": 66, + "parse_error": 0, + "exec_error": 45, + "by_op": { + "add_atom": { + "n": 20, + "exec_match": 1, + "type_match": 0, + "parse_error": 0, + "exec_error": 5 + }, + "add_bond": { + "n": 20, + "exec_match": 0, + "type_match": 3, + "parse_error": 0, + "exec_error": 6 + }, + "add_functional_group": { + "n": 20, + "exec_match": 2, + "type_match": 6, + "parse_error": 0, + "exec_error": 3 + }, + "change_atom_element": { + "n": 20, + "exec_match": 4, + "type_match": 5, + "parse_error": 0, + "exec_error": 3 + }, + "change_bond_order": { + "n": 20, + "exec_match": 9, + "type_match": 14, + "parse_error": 0, + "exec_error": 2 + }, + "change_charge": { + "n": 20, + "exec_match": 10, + "type_match": 10, + "parse_error": 0, + "exec_error": 0 + }, + "flip_chirality": { + "n": 20, + "exec_match": 2, + "type_match": 4, + "parse_error": 0, + "exec_error": 4 + }, + "flip_ez": { + "n": 5, + "exec_match": 0, + "type_match": 0, + "parse_error": 0, + "exec_error": 1 + }, + "move_substituent": { + "n": 20, + "exec_match": 2, + "type_match": 7, + "parse_error": 0, + "exec_error": 6 + }, + "remove_atom": { + "n": 20, + "exec_match": 13, + "type_match": 3, + "parse_error": 0, + "exec_error": 2 + }, + "remove_bond": { + "n": 20, + "exec_match": 3, + "type_match": 4, + "parse_error": 0, + "exec_error": 6 + }, + "remove_functional_group": { + "n": 20, + "exec_match": 17, + "type_match": 10, + "parse_error": 0, + "exec_error": 1 + }, + "swap_substituents": { + "n": 20, + "exec_match": 0, + "type_match": 0, + "parse_error": 0, + "exec_error": 6 + } + } + }, + "gemini-3.1-pro-preview": { + "total": 245, + "exec_match": 195, + "type_match": 173, + "parse_error": 14, + "exec_error": 8, + "by_op": { + "add_atom": { + "n": 20, + "exec_match": 19, + "type_match": 12, + "parse_error": 1, + "exec_error": 0 + }, + "add_bond": { + "n": 20, + "exec_match": 19, + "type_match": 20, + "parse_error": 0, + "exec_error": 0 + }, + "add_functional_group": { + "n": 20, + "exec_match": 17, + "type_match": 10, + "parse_error": 0, + "exec_error": 1 + }, + "change_atom_element": { + "n": 20, + "exec_match": 20, + "type_match": 20, + "parse_error": 0, + "exec_error": 0 + }, + "change_bond_order": { + "n": 20, + "exec_match": 17, + "type_match": 17, + "parse_error": 1, + "exec_error": 0 + }, + "change_charge": { + "n": 20, + "exec_match": 20, + "type_match": 20, + "parse_error": 0, + "exec_error": 0 + }, + "flip_chirality": { + "n": 20, + "exec_match": 7, + "type_match": 12, + "parse_error": 4, + "exec_error": 0 + }, + "flip_ez": { + "n": 5, + "exec_match": 5, + "type_match": 5, + "parse_error": 0, + "exec_error": 0 + }, + "move_substituent": { + "n": 20, + "exec_match": 11, + "type_match": 14, + "parse_error": 2, + "exec_error": 1 + }, + "remove_atom": { + "n": 20, + "exec_match": 18, + "type_match": 17, + "parse_error": 1, + "exec_error": 1 + }, + "remove_bond": { + "n": 20, + "exec_match": 18, + "type_match": 18, + "parse_error": 1, + "exec_error": 0 + }, + "remove_functional_group": { + "n": 20, + "exec_match": 20, + "type_match": 1, + "parse_error": 0, + "exec_error": 0 + }, + "swap_substituents": { + "n": 20, + "exec_match": 4, + "type_match": 7, + "parse_error": 4, + "exec_error": 5 + } + } + }, + "claude-opus-4-6": { + "total": 245, + "exec_match": 138, + "type_match": 126, + "parse_error": 20, + "exec_error": 18, + "by_op": { + "add_atom": { + "n": 20, + "exec_match": 12, + "type_match": 1, + "parse_error": 3, + "exec_error": 1 + }, + "add_bond": { + "n": 20, + "exec_match": 9, + "type_match": 13, + "parse_error": 3, + "exec_error": 2 + }, + "add_functional_group": { + "n": 20, + "exec_match": 9, + "type_match": 14, + "parse_error": 2, + "exec_error": 0 + }, + "change_atom_element": { + "n": 20, + "exec_match": 15, + "type_match": 16, + "parse_error": 2, + "exec_error": 0 + }, + "change_bond_order": { + "n": 20, + "exec_match": 15, + "type_match": 16, + "parse_error": 2, + "exec_error": 0 + }, + "change_charge": { + "n": 20, + "exec_match": 19, + "type_match": 19, + "parse_error": 0, + "exec_error": 0 + }, + "flip_chirality": { + "n": 20, + "exec_match": 3, + "type_match": 4, + "parse_error": 4, + "exec_error": 1 + }, + "flip_ez": { + "n": 5, + "exec_match": 3, + "type_match": 3, + "parse_error": 0, + "exec_error": 0 + }, + "move_substituent": { + "n": 20, + "exec_match": 4, + "type_match": 9, + "parse_error": 1, + "exec_error": 4 + }, + "remove_atom": { + "n": 20, + "exec_match": 16, + "type_match": 8, + "parse_error": 1, + "exec_error": 1 + }, + "remove_bond": { + "n": 20, + "exec_match": 9, + "type_match": 11, + "parse_error": 1, + "exec_error": 6 + }, + "remove_functional_group": { + "n": 20, + "exec_match": 20, + "type_match": 6, + "parse_error": 0, + "exec_error": 0 + }, + "swap_substituents": { + "n": 20, + "exec_match": 4, + "type_match": 6, + "parse_error": 1, + "exec_error": 3 + } + } + } +} \ No newline at end of file diff --git a/data/dataset.json b/data/dataset.json new file mode 100644 index 0000000000000000000000000000000000000000..6625bb335fc9a69425cbb9ba22b3986557eb8d3d --- /dev/null +++ b/data/dataset.json @@ -0,0 +1,4027 @@ +[ + { + "id": "000000", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC(C)(S)c1ccc(O)c(O)c1", + "wrong_smiles_mapped": "[CH3:1][C:2]([SH:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "image_path": "images/000000.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 3, + "from_elem": "S", + "to_elem": "C" + }, + "description": "Change atom 2 from S back to C" + } + }, + { + "id": "000001", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "COc1cc(C(C)(C)C)ccc1O", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([O:11][CH3:13])[cH:12]1", + "image_path": "images/000001.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 13, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000002", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC(C)c1ccc(O)c(O)c1", + "wrong_smiles_mapped": "[CH:1]([CH3:2])([CH3:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:9]([OH:10])[cH:11]1", + "image_path": "images/000002.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "C", + "bond_type": "SINGLE" + }, + "description": "Add missing C atom back to anchor" + } + }, + { + "id": "000003", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC1(C)COc2ccc1cc2O", + "wrong_smiles_mapped": "[CH3:1][C:2]1([CH3:4])[CH2:3][O:9][c:8]2[cH:7][cH:6][c:5]1[cH:12][c:10]2[OH:11]", + "image_path": "images/000003.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 3, + "atom2_map": 9 + }, + "description": "Remove spurious bond between atoms 2 and 8" + } + }, + { + "id": "000004", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC(C)(C)c1ccc(O)cc1.O", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:12]1.[OH2:11]", + "image_path": "images/000004.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 10, + "atom2_map": 11, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 9 and 10" + } + }, + { + "id": "000005", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC(C)(C)c1cc(O)c(O)c(F)c1", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c:7]([F:13])[c:8]([OH:9])[c:10]([OH:11])[cH:12]1", + "image_path": "images/000005.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 7, + "group_name": "F" + }, + "description": "Remove extra -F group" + } + }, + { + "id": "000006", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC(C)(C)c1cccc(O)c1", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:11]1", + "image_path": "images/000006.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 8, + "group_name": "OH" + }, + "description": "Add -OH back to anchor atom" + } + }, + { + "id": "000007", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC(C)(C)c1cccc(O)c1O", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:7]1[cH:6][cH:5][cH:12][c:10]([OH:11])[c:8]1[OH:9]", + "image_path": "images/000007.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 2, + "from_map": 7, + "to_map": 5 + }, + "description": "Move substituent 1 back from ring atom 6 to 4" + } + }, + { + "id": "000008", + "cid": "7381", + "correct_smiles": "CC(C)(C)c1ccc(O)c(O)c1", + "wrong_smiles": "CC(C)(C)c1cc(O)ccc1O", + "wrong_smiles_mapped": "[CH3:1][C:2]([CH3:3])([CH3:4])[c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([OH:11])[cH:12]1", + "image_path": "images/000008.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 5, + "ring2_map": 10 + }, + "description": "Swap substituents back between ring atoms 4 and 9" + } + }, + { + "id": "000009", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NN(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles_mapped": "[NH2:1][N:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "image_path": "images/000009.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 2, + "from_elem": "N", + "to_elem": "C" + }, + "description": "Change atom 1 from N back to C" + } + }, + { + "id": "000010", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NOc1cccc(CC(N)C(=O)O)c1", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][NH2:14])[cH:10]1)[C:11](=[O:12])[OH:13]", + "image_path": "images/000010.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 14, + "elem": "N" + }, + "description": "Remove extra N atom (added by corruption)" + } + }, + { + "id": "000011", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NC(C=O)Cc1cccc(O)c1", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12]", + "image_path": "images/000011.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 11, + "new_elem": "O", + "bond_type": "SINGLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000012", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NC(Cc1cccc(O)c1)C(O)=[OH+]", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[OH+:12])[OH:13]", + "image_path": "images/000012.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 12, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000013", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "N=C(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles_mapped": "[NH:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "image_path": "images/000013.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 1, + "atom2_map": 2, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (0-1) from DOUBLE back to SINGLE" + } + }, + { + "id": "000014", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NC(Cc1ccc2c(c1)O2)C(=O)O", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:10]1)[O:9]2)[C:11](=[O:12])[OH:13]", + "image_path": "images/000014.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 7, + "atom2_map": 9 + }, + "description": "Remove spurious bond between atoms 6 and 8" + } + }, + { + "id": "000015", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NC(C=O)Cc1cccc(O)c1.O", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:10]1)[CH:11]=[O:12].[OH2:13]", + "image_path": "images/000015.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 11, + "atom2_map": 13, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 10 and 12" + } + }, + { + "id": "000016", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NC(Cc1ccc(F)c(O)c1)C(=O)O", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([F:14])[c:8]([OH:9])[cH:10]1)[C:11](=[O:12])[OH:13]", + "image_path": "images/000016.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 7, + "group_name": "F" + }, + "description": "Remove extra -F group" + } + }, + { + "id": "000017", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NC(Cc1ccccc1)C(=O)O", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[C:10](=[O:11])[OH:12]", + "image_path": "images/000017.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 8, + "group_name": "OH" + }, + "description": "Add -OH back to anchor atom" + } + }, + { + "id": "000018", + "cid": "13052", + "correct_smiles": "NC(Cc1cccc(O)c1)C(=O)O", + "wrong_smiles": "NC(Cc1ccccc1O)C(=O)O", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:10]1[OH:9])[C:11](=[O:12])[OH:13]", + "image_path": "images/000018.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 9, + "from_map": 10, + "to_map": 8 + }, + "description": "Move substituent 8 back from ring atom 9 to 7" + } + }, + { + "id": "000019", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "Cc1ccc2cc3c(ccc4cc(S)ccc43)cc2c1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([SH:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "image_path": "images/000019.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 14, + "from_elem": "S", + "to_elem": "C" + }, + "description": "Change atom 13 from S back to C" + } + }, + { + "id": "000020", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "Cc1ccc2cc3c(ccc4cc(CO)ccc43)cc2c1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH2:14][OH:21])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "image_path": "images/000020.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 21, + "elem": "O" + }, + "description": "Remove extra O atom (added by corruption)" + } + }, + { + "id": "000021", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "Cc1ccc2cc3c(ccc4ccccc43)cc2c1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "image_path": "images/000021.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 13, + "new_elem": "C", + "bond_type": "SINGLE" + }, + "description": "Add missing C atom back to anchor" + } + }, + { + "id": "000022", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "Cc1cc2c3c-2c2c(ccc4cc(C)ccc42)cc3c1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]2[c:5]3[c:6]-2[c:7]2[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]24)[cH:18][c:19]3[cH:20]1", + "image_path": "images/000022.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 4, + "atom2_map": 6 + }, + "description": "Remove spurious bond between atoms 3 and 5" + } + }, + { + "id": "000023", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "C.Cc1ccc2c(ccc3cc4ccccc4cc32)c1", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "image_path": "images/000023.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 1, + "atom2_map": 2, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 0 and 1" + } + }, + { + "id": "000024", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "Cc1ccc2c(C)c3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH3:21])[c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][c:13]([CH3:14])[cH:15][cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "image_path": "images/000024.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 6, + "group_name": "CH3" + }, + "description": "Remove extra -CH3 group" + } + }, + { + "id": "000025", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "Cc1ccc2c(ccc3cc4ccccc4cc32)c1", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][c:6]3[c:7]([cH:8][cH:9][c:10]4[cH:11][c:12]([CH3:13])[cH:14][cH:15][c:16]34)[cH:17][c:18]2[cH:19]1", + "image_path": "images/000025.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "CH3" + }, + "description": "Add -CH3 back to anchor atom" + } + }, + { + "id": "000026", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "Cc1ccc2cc3c(ccc4ccc(C)cc43)cc2c1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10][c:11]4[cH:12][cH:13][c:15]([CH3:14])[cH:16][c:17]34)[cH:18][c:19]2[cH:20]1", + "image_path": "images/000026.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 14, + "from_map": 15, + "to_map": 13 + }, + "description": "Move substituent 13 back from ring atom 14 to 12" + } + }, + { + "id": "000027", + "cid": "9428", + "correct_smiles": "Cc1ccc2cc3c(ccc4cc(C)ccc43)cc2c1", + "wrong_smiles": "CC1=Cc2cc(c3cc2C=Cc2cc(C)ccc2-3)C=C1", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:20][c:19]2[c:5]3[cH:6][c:7]([c:8]([cH:18]2)[CH:4]=[CH:3]1)-[c:17]1[c:11]([cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[CH:10]=[CH:9]3", + "image_path": "images/000027.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 8, + "ring2_map": 5 + }, + "description": "Swap substituents back between ring atoms 7 and 4" + } + }, + { + "id": "000028", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4O)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]4[OH:46])[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "image_path": "images/000028.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 46, + "elem": "O" + }, + "description": "Remove extra O atom (added by corruption)" + } + }, + { + "id": "000029", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O=S(O)c1cccc2c(N=Nc3ccc(N=Nc4cccc(S(=O)(=O)O)c4)c4ccccc34)ccc(Nc3ccccc3)c12", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])[OH:33])[cH:34][cH:35][cH:36][c:37]34)[c:38]3[cH:39][cH:40][cH:41][cH:42][c:43]23)[cH:44]1", + "image_path": "images/000029.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 31, + "new_elem": "O", + "bond_type": "DOUBLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000030", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=[NH+]c3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[NH+:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "image_path": "images/000030.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 17, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000031", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O=S(=O)(O)c1cccc2c(N=Nc3ccc(N=Nc4cccc([SH](=O)(O)O)c4)c4ccccc34)ccc(Nc3ccccc3)c12", + "wrong_smiles_mapped": "[OH:1][SH:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "image_path": "images/000031.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 1, + "atom2_map": 2, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (0-1) from SINGLE back to DOUBLE" + } + }, + { + "id": "000032", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc3c4cccc(c24)-c2ccc(S(=O)(=O)O)c4c(Nc5ccccc5)ccc(c24)N=N3)c1", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]3[c:39]4[cH:40][cH:41][cH:42][c:43]([c:44]24)-[c:37]2[cH:36][cH:35][c:30]([S:31](=[O:32])(=[O:33])[OH:34])[c:29]4[c:21]([NH:22][c:23]5[cH:24][cH:25][cH:26][cH:27][cH:28]5)[cH:20][cH:19][c:18]([c:38]42)[N:17]=[N:16]3)[cH:45]1", + "image_path": "images/000032.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 37, + "atom2_map": 43 + }, + "description": "Remove spurious bond between atoms 36 and 42" + } + }, + { + "id": "000033", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O.O=S(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles_mapped": "[O:1]=[S:2]([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[cH:13][cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1.[OH2:3]", + "image_path": "images/000033.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "DOUBLE" + }, + "description": "Add back DOUBLE bond between atoms 1 and 2" + } + }, + { + "id": "000034", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O=S(=O)(O)c1cccc(N=Nc2c(Cl)cc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][c:12]2[c:13]([Cl:46])[cH:14][c:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:39]3[cH:40][cH:41][cH:42][cH:43][c:44]23)[cH:45]1", + "image_path": "images/000034.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 13, + "group_name": "Cl" + }, + "description": "Remove extra -Cl group" + } + }, + { + "id": "000035", + "cid": "18777", + "correct_smiles": "O=S(=O)(O)c1cccc(N=Nc2ccc(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccccc23)c1", + "wrong_smiles": "O=S(=O)(O)c1cccc(N=NC2=CC=C(N=Nc3ccc(Nc4ccccc4)c4c(S(=O)(=O)O)cccc34)c3ccc2cc3)c1", + "wrong_smiles_mapped": "[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([N:10]=[N:11][C:12]2=[CH:13][CH:14]=[C:15]([N:16]=[N:17][c:18]3[cH:19][cH:20][c:21]([NH:22][c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:29]4[c:30]([S:31](=[O:32])(=[O:33])[OH:34])[cH:35][cH:36][cH:37][c:38]34)[c:41]3[cH:40][cH:39][c:44]2[cH:43][cH:42]3)[cH:45]1", + "image_path": "images/000035.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 15, + "from_map": 41, + "to_map": 39 + }, + "description": "Move substituent 14 back from ring atom 40 to 38" + } + }, + { + "id": "000036", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "NNCSSc1ccccc1", + "wrong_smiles_mapped": "[NH2:1][NH:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "image_path": "images/000036.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 2, + "from_elem": "N", + "to_elem": "C" + }, + "description": "Change atom 1 from N back to C" + } + }, + { + "id": "000037", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "NCCSSc1ccccc1O", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12]", + "image_path": "images/000037.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 12, + "elem": "O" + }, + "description": "Remove extra O atom (added by corruption)" + } + }, + { + "id": "000038", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "CCSSc1ccccc1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "image_path": "images/000038.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "N", + "bond_type": "SINGLE" + }, + "description": "Add missing N atom back to anchor" + } + }, + { + "id": "000039", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "NCC=[SH]Sc1ccccc1", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[SH:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1", + "image_path": "images/000039.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 3, + "atom2_map": 4, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (2-3) from DOUBLE back to SINGLE" + } + }, + { + "id": "000040", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "NCCSSc1c2cccc1-2", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][S:4][S:5][c:6]1[c:7]2[cH:8][cH:9][cH:10][c:11]1-2", + "image_path": "images/000040.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 7, + "atom2_map": 11 + }, + "description": "Remove spurious bond between atoms 6 and 10" + } + }, + { + "id": "000041", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "CN.CSSc1ccccc1", + "wrong_smiles_mapped": "[CH3:3][S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:1][CH3:2]", + "image_path": "images/000041.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 1 and 2" + } + }, + { + "id": "000042", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "NCC(Cl)SSc1ccccc1", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([S:4][S:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[Cl:12]", + "image_path": "images/000042.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 3, + "group_name": "Cl" + }, + "description": "Remove extra -Cl group" + } + }, + { + "id": "000043", + "cid": "19796", + "correct_smiles": "NCCSSc1ccccc1", + "wrong_smiles": "CCSSc1ccccc1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][S:3][S:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1", + "image_path": "images/000043.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "NH2" + }, + "description": "Add -NH2 back to anchor atom" + } + }, + { + "id": "000044", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "NCCCNCCOP(=O)(O)O", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][P:9](=[O:10])([OH:11])[OH:12]", + "image_path": "images/000044.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 8, + "from_elem": "O", + "to_elem": "S" + }, + "description": "Change atom 7 from O back to S" + } + }, + { + "id": "000045", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "NC(O)CCNCCSP(=O)(O)O", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[OH:13]", + "image_path": "images/000045.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 13, + "elem": "O" + }, + "description": "Remove extra O atom (added by corruption)" + } + }, + { + "id": "000046", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "NCCCNCCS[PH](=O)O", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9](=[O:10])[OH:11]", + "image_path": "images/000046.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 9, + "new_elem": "O", + "bond_type": "SINGLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000047", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "NCCCNCCSP(O)(O)=[OH+]", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[OH+:10])([OH:11])[OH:12]", + "image_path": "images/000047.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 10, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000048", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "NCCCNCCS[PH](O)(O)O", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][PH:9]([OH:10])([OH:11])[OH:12]", + "image_path": "images/000048.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 9, + "atom2_map": 10, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (8-9) from SINGLE back to DOUBLE" + } + }, + { + "id": "000049", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "NCC1CNCCSP(=O)(O)O1", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[O:12]1", + "image_path": "images/000049.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 3, + "atom2_map": 12 + }, + "description": "Remove spurious bond between atoms 2 and 11" + } + }, + { + "id": "000050", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "CCNCCSP(=O)(O)O.CN", + "wrong_smiles_mapped": "[CH3:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12].[NH2:1][CH3:2]", + "image_path": "images/000050.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 1 and 2" + } + }, + { + "id": "000051", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "NC(F)CCNCCSP(=O)(O)O", + "wrong_smiles_mapped": "[NH2:1][CH:2]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][S:8][P:9](=[O:10])([OH:11])[OH:12])[F:13]", + "image_path": "images/000051.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 2, + "group_name": "F" + }, + "description": "Remove extra -F group" + } + }, + { + "id": "000052", + "cid": "2141", + "correct_smiles": "NCCCNCCSP(=O)(O)O", + "wrong_smiles": "CCCNCCSP(=O)(O)O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][S:7][P:8](=[O:9])([OH:10])[OH:11]", + "image_path": "images/000052.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "NH2" + }, + "description": "Add -NH2 back to anchor atom" + } + }, + { + "id": "000053", + "cid": "1056", + "correct_smiles": "C1=CNCN=C1", + "wrong_smiles": "C1=CNCN=N1", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][N:5]=[N:6]1", + "image_path": "images/000053.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 6, + "from_elem": "N", + "to_elem": "C" + }, + "description": "Change atom 5 from N back to C" + } + }, + { + "id": "000054", + "cid": "1056", + "correct_smiles": "C1=CNCN=C1", + "wrong_smiles": "NC1=CC=NCN1", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([NH2:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "image_path": "images/000054.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 7, + "elem": "N" + }, + "description": "Remove extra N atom (added by corruption)" + } + }, + { + "id": "000055", + "cid": "1056", + "correct_smiles": "C1=CNCN=C1", + "wrong_smiles": "C1=CNC[NH+]=C1", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH2:4][NH+:5]=[CH:6]1", + "image_path": "images/000055.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 5, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000056", + "cid": "1056", + "correct_smiles": "C1=CNCN=C1", + "wrong_smiles": "C1=C=NCNC=1", + "wrong_smiles_mapped": "[C:1]1=[CH:2][NH:3][CH2:4][N:5]=[C:6]=1", + "image_path": "images/000056.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 6, + "atom2_map": 1, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (5-0) from DOUBLE back to SINGLE" + } + }, + { + "id": "000057", + "cid": "1056", + "correct_smiles": "C1=CNCN=C1", + "wrong_smiles": "C1=CC2=NC2N1", + "wrong_smiles_mapped": "[CH:1]1=[CH:2][NH:3][CH:4]2[N:5]=[C:6]12", + "image_path": "images/000057.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 4, + "atom2_map": 6 + }, + "description": "Remove spurious bond between atoms 3 and 5" + } + }, + { + "id": "000058", + "cid": "1056", + "correct_smiles": "C1=CNCN=C1", + "wrong_smiles": "CC1=CC=NCN1", + "wrong_smiles_mapped": "[CH:1]1=[C:2]([CH3:7])[NH:3][CH2:4][N:5]=[CH:6]1", + "image_path": "images/000058.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 2, + "group_name": "CH3" + }, + "description": "Remove extra -CH3 group" + } + }, + { + "id": "000059", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CCCCCCCCCCN(C)c1cc(CS)cc(NC(C)=O)c1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][SH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "image_path": "images/000059.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 17, + "from_elem": "S", + "to_elem": "O" + }, + "description": "Change atom 16 from S back to O" + } + }, + { + "id": "000060", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CC(=O)Nc1cc(CO)cc(N(C)CCCCCCCCC(C)N)c1", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[NH2:25]", + "image_path": "images/000060.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 25, + "elem": "N" + }, + "description": "Remove extra N atom (added by corruption)" + } + }, + { + "id": "000061", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CCCCCCCCCCN(C)c1cc(C)cc(NC(C)=O)c1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "image_path": "images/000061.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 16, + "new_elem": "O", + "bond_type": "SINGLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000062", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CCCCCCCCCC[NH+](C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH+:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "image_path": "images/000062.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 11, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000063", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CCCCCC=CCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1", + "image_path": "images/000063.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 6, + "atom2_map": 7, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (5-6) from DOUBLE back to SINGLE" + } + }, + { + "id": "000064", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CCCCCCC1CCCN(C)c2cc(CO)c1c(NC(C)=O)c2", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]2[cH:14][c:15]([CH2:16][OH:17])[c:18]1[c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]2", + "image_path": "images/000064.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 7, + "atom2_map": 18 + }, + "description": "Remove spurious bond between atoms 6 and 17" + } + }, + { + "id": "000065", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CC=O.CCCCCCCCCCN(C)c1cc(N)cc(CO)c1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH2:20])[cH:24]1.[CH:21]([CH3:22])=[O:23]", + "image_path": "images/000065.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 20, + "atom2_map": 21, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 19 and 20" + } + }, + { + "id": "000066", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CC(=O)Nc1cc(CO)cc(N(C)CCCCCCCCC(C)O)c1", + "wrong_smiles_mapped": "[CH3:1][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH2:16][OH:17])[cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[cH:24]1)[OH:25]", + "image_path": "images/000066.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 2, + "group_name": "OH" + }, + "description": "Remove extra -OH group" + } + }, + { + "id": "000067", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CCCCCCCCCCN(C)c1cc(C)cc(NC(C)=O)c1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][c:15]([CH3:16])[cH:17][c:18]([NH:19][C:20]([CH3:21])=[O:22])[cH:23]1", + "image_path": "images/000067.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 16, + "group_name": "OH" + }, + "description": "Add -OH back to anchor atom" + } + }, + { + "id": "000068", + "cid": "2032", + "correct_smiles": "CCCCCCCCCCN(C)c1cc(CO)cc(NC(C)=O)c1", + "wrong_smiles": "CCCCCCCCCCN(C)c1cccc(NC(C)=O)c1CO", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH3:12])[c:13]1[cH:14][cH:15][cH:18][c:19]([NH:20][C:21]([CH3:22])=[O:23])[c:24]1[CH2:16][OH:17]", + "image_path": "images/000068.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 16, + "from_map": 24, + "to_map": 15 + }, + "description": "Move substituent 15 back from ring atom 23 to 14" + } + }, + { + "id": "000069", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(CCCN1CCC2(CO1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][O:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "image_path": "images/000069.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 11, + "from_elem": "O", + "to_elem": "C" + }, + "description": "Change atom 10 from O back to C" + } + }, + { + "id": "000070", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(CCCN1CCC2(CC1O)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH:7]([OH:30])[CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "image_path": "images/000070.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 30, + "elem": "O" + }, + "description": "Remove extra O atom (added by corruption)" + } + }, + { + "id": "000071", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C1NCN(c2ccccc2)C12CCN(CCCCc1ccc(F)cc1)CC2", + "wrong_smiles_mapped": "[CH2:1]([CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[C:11](=[O:12])[NH:13][CH2:14][N:15]2[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1", + "image_path": "images/000071.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "O", + "bond_type": "DOUBLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000072", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(CCC[NH+]1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][NH+:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "image_path": "images/000072.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 6, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000073", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(C=CCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]=[CH:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "image_path": "images/000073.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 3, + "atom2_map": 4, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (2-3) from DOUBLE back to SINGLE" + } + }, + { + "id": "000074", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(c1ccc(F)cc1)C1CCN2CCC3(C(=O)NCN3c3ccccc3)C1C2", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH:3]1[CH2:4][CH2:5][N:6]2[CH2:7][CH2:8][C:9]3([CH:10]1[CH2:11]2)[C:12](=[O:13])[NH:14][CH2:15][N:16]3[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "image_path": "images/000074.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 3, + "atom2_map": 10 + }, + "description": "Remove spurious bond between atoms 2 and 9" + } + }, + { + "id": "000075", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1.O=Cc1ccc(F)cc1", + "wrong_smiles_mapped": "[CH3:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[O:1]=[CH:2][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1", + "image_path": "images/000075.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 1 and 2" + } + }, + { + "id": "000076", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)c(F)c1", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([F:27])[c:28]([F:30])[cH:29]1", + "image_path": "images/000076.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 28, + "group_name": "F" + }, + "description": "Remove extra -F group" + } + }, + { + "id": "000077", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccccc1", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1", + "image_path": "images/000077.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 26, + "group_name": "F" + }, + "description": "Add -F back to anchor atom" + } + }, + { + "id": "000078", + "cid": "5265", + "correct_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1", + "wrong_smiles": "O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1cccc(F)c1", + "wrong_smiles_mapped": "[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[C:12](=[O:13])[NH:14][CH2:15][N:16]2[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][c:25]([F:27])[cH:26][cH:28][cH:29]1", + "image_path": "images/000078.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 27, + "from_map": 25, + "to_map": 26 + }, + "description": "Move substituent 26 back from ring atom 24 to 25" + } + }, + { + "id": "000079", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1CSC(=O)C1C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][S:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "image_path": "images/000079.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 23, + "from_elem": "S", + "to_elem": "O" + }, + "description": "Change atom 22 from S back to O" + } + }, + { + "id": "000080", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1C(O)OC(=O)C1C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH:22]([OH:31])[O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "image_path": "images/000080.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 31, + "elem": "O" + }, + "description": "Remove extra O atom (added by corruption)" + } + }, + { + "id": "000081", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1c(O)cc2c(c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles_mapped": "[OH:1][c:2]1[cH:3][c:4]2[c:5]([c:6]([O:7][CH3:8])[c:9]1[O:10][CH3:11])-[c:12]1[cH:13][c:14]3[c:15]([cH:16][c:17]1[C:18](=[O:19])[CH:20]1[CH2:21][O:22][C:23](=[O:24])[CH:25]1[CH2:26]2)[O:27][CH2:28][O:29]3", + "image_path": "images/000081.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "C", + "bond_type": "SINGLE" + }, + "description": "Add missing C atom back to anchor" + } + }, + { + "id": "000082", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=[OH+])C1C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[OH+:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "image_path": "images/000082.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 25, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000083", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(O)C1COC(=O)C1C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[CH:19]([OH:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "image_path": "images/000083.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 19, + "atom2_map": 20, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (18-19) from SINGLE back to DOUBLE" + } + }, + { + "id": "000084", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(c4c1C(=O)C1COC(=O)C41C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([c:17]4[c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[C:26]41[CH2:27]2)[O:28][CH2:29][O:30]3", + "image_path": "images/000084.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 17, + "atom2_map": 26 + }, + "description": "Remove spurious bond between atoms 16 and 25" + } + }, + { + "id": "000085", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "CO.COc1cc2c(cc1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[CH:21]1[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3.[OH:8][CH3:9]", + "image_path": "images/000085.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 7, + "atom2_map": 8, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 6 and 7" + } + }, + { + "id": "000086", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1(N)COC(=O)C1C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:21]1([NH2:31])[CH2:22][O:23][C:24](=[O:25])[CH:26]1[CH2:27]2)[O:28][CH2:29][O:30]3", + "image_path": "images/000086.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 21, + "group_name": "NH2" + }, + "description": "Remove extra -NH2 group" + } + }, + { + "id": "000087", + "cid": "5283", + "correct_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1COC(=O)C1C2)OCO3", + "wrong_smiles": "COc1cc2c(c(OC)c1OC)-c1cc3c(cc1C(=O)C1(CCOC1=O)C2)OCO3", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([c:7]([O:8][CH3:9])[c:10]1[O:11][CH3:12])-[c:13]1[cH:14][c:15]3[c:16]([cH:17][c:18]1[C:19](=[O:20])[C:26]1([CH2:21][CH2:22][O:23][C:24]1=[O:25])[CH2:27]2)[O:28][CH2:29][O:30]3", + "image_path": "images/000087.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 19, + "from_map": 26, + "to_map": 21 + }, + "description": "Move substituent 18 back from ring atom 25 to 20" + } + }, + { + "id": "000088", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(NC=Cc3ccccc3)CC2)cc1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([NH:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "image_path": "images/000088.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 18, + "from_elem": "N", + "to_elem": "C" + }, + "description": "Change atom 17 from N back to C" + } + }, + { + "id": "000089", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "CC1CN(C(c2ccc(F)cc2)c2ccc(F)cc2)CCN1CC=Cc1ccccc1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH:27]([CH3:31])[CH2:28]2)[cH:29][cH:30]1", + "image_path": "images/000089.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 31, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000090", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(C(c2ccccc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "image_path": "images/000090.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "F", + "bond_type": "SINGLE" + }, + "description": "Add missing F atom back to anchor" + } + }, + { + "id": "000091", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(C(c2ccc(F)cc2)[NH+]2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[NH+:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "image_path": "images/000091.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 14, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000092", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2C=CN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[N:14]2[CH:15]=[CH:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "image_path": "images/000092.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 15, + "atom2_map": 16, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (14-15) from DOUBLE back to SINGLE" + } + }, + { + "id": "000093", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(C2c3ccc(F)c(c3)C3CN2CCN3CC=Cc2ccccc2)cc1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]2[cH:29][c:30]1[CH:16]1[CH2:15][N:14]([CH:6]2[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[CH2:28][CH2:27][N:17]1[CH2:18][CH:19]=[CH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1", + "image_path": "images/000093.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 16, + "atom2_map": 30 + }, + "description": "Remove spurious bond between atoms 15 and 29" + } + }, + { + "id": "000094", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(CN2CCN(CC=Cc3ccccc3)CC2)cc1.Fc1ccccc1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1.[cH:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]1", + "image_path": "images/000094.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 6, + "atom2_map": 7, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 5 and 6" + } + }, + { + "id": "000095", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "CC(c1ccc(F)cc1)(c1ccc(F)cc1)N1CCN(CC=Cc2ccccc2)CC1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)([N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[CH3:31])[cH:29][cH:30]1", + "image_path": "images/000095.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 6, + "group_name": "CH3" + }, + "description": "Remove extra -CH3 group" + } + }, + { + "id": "000096", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(C(c2ccccc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]([CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[N:13]2[CH2:14][CH2:15][N:16]([CH2:17][CH:18]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1", + "image_path": "images/000096.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "F" + }, + "description": "Add -F back to anchor atom" + } + }, + { + "id": "000097", + "cid": "3378", + "correct_smiles": "Fc1ccc(C(c2ccc(F)cc2)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles": "Fc1ccc(C(c2ccccc2F)N2CCN(CC=Cc3ccccc3)CC2)cc1", + "wrong_smiles_mapped": "[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([c:9]2[cH:8][cH:7][cH:13][cH:12][c:10]2[F:11])[N:14]2[CH2:15][CH2:16][N:17]([CH2:18][CH:19]=[CH:20][c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][cH:30]1", + "image_path": "images/000097.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 6, + "from_map": 9, + "to_map": 7 + }, + "description": "Move substituent 5 back from ring atom 8 to 6" + } + }, + { + "id": "000098", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP(=O)(OCC)SN1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[S:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "image_path": "images/000098.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 9, + "from_elem": "S", + "to_elem": "O" + }, + "description": "Change atom 8 from S back to O" + } + }, + { + "id": "000099", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH2:8][CH3:25])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "image_path": "images/000099.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 25, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000100", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4]([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "image_path": "images/000100.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 4, + "new_elem": "O", + "bond_type": "DOUBLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000101", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP(=O)(ON1C(=O)c2cccc3cccc(c23)C1=O)[OH+]CC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][OH+:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "image_path": "images/000101.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 3, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000102", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCO[PH](O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4]([OH:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "image_path": "images/000102.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 4, + "atom2_map": 5, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (3-4) from SINGLE back to DOUBLE" + } + }, + { + "id": "000103", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP1(=O)OCCc2ccc3cccc4c3c2C(=O)N(O1)C4=O", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]2[C:11](=[O:12])[c:13]3[c:14]1[cH:15][cH:16][c:17]1[cH:18][cH:19][cH:20][c:21]([c:22]31)[C:23]2=[O:24]", + "image_path": "images/000103.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 1, + "atom2_map": 14 + }, + "description": "Remove spurious bond between atoms 0 and 13" + } + }, + { + "id": "000104", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCO[PH](=O)OCC.O=C1c2cccc3cccc(c23)C(=O)N1O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][PH:4](=[O:5])[O:6][CH2:7][CH3:8].[OH:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "image_path": "images/000104.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 4, + "atom2_map": 9, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 3 and 8" + } + }, + { + "id": "000105", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cc(Cl)cc(c23)C1=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][c:15]([Cl:25])[cH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([c:22]23)[C:23]1=[O:24]", + "image_path": "images/000105.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 15, + "group_name": "Cl" + }, + "description": "Remove extra -Cl group" + } + }, + { + "id": "000106", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP(=O)(OC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles_mapped": "[CH3:1][O:2][P:3](=[O:4])([O:5][CH2:6][CH3:7])[O:8][N:9]1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([c:21]23)[C:22]1=[O:23]", + "image_path": "images/000106.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "CH3" + }, + "description": "Add -CH3 back to anchor atom" + } + }, + { + "id": "000107", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP(=O)(OCC)On1c(=O)c2c3cc(cc(c3)c1=O)C=CC=2", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][n:10]1[c:11](=[O:12])[c:13]2[cH:14][c:15]3[cH:16][c:17]([cH:22]2)[CH:18]=[CH:19][CH:20]=[c:21]3[c:23]1=[O:24]", + "image_path": "images/000107.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 21, + "from_map": 15, + "to_map": 22 + }, + "description": "Move substituent 20 back from ring atom 14 to 21" + } + }, + { + "id": "000108", + "cid": "15148", + "correct_smiles": "CCOP(=O)(OCC)ON1C(=O)c2cccc3cccc(c23)C1=O", + "wrong_smiles": "CCOP(=O)(OCC)OC1=C2C=CC=C3C=CC=C1C(=O)N3C2=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[O:5])([O:6][CH2:7][CH3:8])[O:9][C:22]1=[C:13]2[C:11](=[O:12])[N:10]3[C:17](=[CH:16][CH:15]=[CH:14]2)[CH:18]=[CH:19][CH:20]=[C:21]1[C:23]3=[O:24]", + "image_path": "images/000108.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 22, + "ring2_map": 10 + }, + "description": "Swap substituents back between ring atoms 21 and 9" + } + }, + { + "id": "000109", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCSCCCCCC)COC1OC(CS(=O)(=O)O)C(O)C(O)C1O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000109.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 7, + "from_elem": "S", + "to_elem": "C" + }, + "description": "Change atom 6 from S back to C" + } + }, + { + "id": "000110", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(C)(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[C:35]([OH:36])([CH3:57])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000110.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 57, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000111", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(C[SH](=O)=O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][SH:29](=[O:30])=[O:31])[CH:32]([OH:33])[CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "image_path": "images/000111.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 29, + "new_elem": "O", + "bond_type": "SINGLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000112", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1[OH+]C(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[OH+:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000112.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 26, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000113", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCC=CC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000113.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 16, + "atom2_map": 17, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (15-16) from DOUBLE back to SINGLE" + } + }, + { + "id": "000114", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCC1CCC1CCCC)COC1OC(CS(=O)(=O)O)C(O)C(O)C1O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000114.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 5, + "atom2_map": 8 + }, + "description": "Remove spurious bond between atoms 4 and 7" + } + }, + { + "id": "000115", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCC(=O)OC(COC=O)COC1OC(CS(=O)(=O)O)C(O)C(O)C1O.CCCCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000115.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 17, + "atom2_map": 18, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 16 and 17" + } + }, + { + "id": "000116", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCC(Br)CCCC)COC1OC(CS(=O)(=O)O)C(O)C(O)C1O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[Br:57]", + "image_path": "images/000116.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 5, + "group_name": "Br" + }, + "description": "Remove extra -Br group" + } + }, + { + "id": "000117", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)CC(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:25]1[O:26][CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[CH2:33][CH:34]([OH:35])[CH:36]1[OH:37])[O:38][C:39](=[O:40])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]", + "image_path": "images/000117.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 33, + "group_name": "OH" + }, + "description": "Add -OH back to anchor atom" + } + }, + { + "id": "000118", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1(CS(=O)(=O)O)OCC(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][C:25]1([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH2:27][CH:33]([OH:34])[CH:35]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000118.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 28, + "from_map": 25, + "to_map": 27 + }, + "description": "Move substituent 27 back from ring atom 24 to 26" + } + }, + { + "id": "000119", + "cid": "5346", + "correct_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1OC(CS(=O)(=O)O)C(O)C(O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles": "CCCCCCCCCCCCCCCCCC(=O)OCC(COC1C(O)C(O)OC(CS(=O)(=O)O)C1O)OC(=O)CCCCCCCCCCCCCCC", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]([CH2:23][O:24][CH:35]1[CH:33]([OH:34])[CH:27]([CH2:28][S:29](=[O:30])(=[O:31])[OH:32])[O:26][CH:25]([OH:36])[CH:37]1[OH:38])[O:39][C:40](=[O:41])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]", + "image_path": "images/000119.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 25, + "ring2_map": 35 + }, + "description": "Swap substituents back between ring atoms 24 and 34" + } + }, + { + "id": "000120", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CC(=O)N(N)O", + "wrong_smiles_mapped": "[CH3:1][C:2](=[O:3])[N:4]([OH:5])[NH2:6]", + "image_path": "images/000120.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 5, + "from_elem": "O", + "to_elem": "C" + }, + "description": "Change atom 4 from O back to C" + } + }, + { + "id": "000121", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CCC(=O)N(C)N", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[CH3:7]", + "image_path": "images/000121.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 7, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000122", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CN(N)C=O", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "image_path": "images/000122.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "C", + "bond_type": "SINGLE" + }, + "description": "Add missing C atom back to anchor" + } + }, + { + "id": "000123", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CC(=[OH+])N(C)N", + "wrong_smiles_mapped": "[CH3:1][C:2](=[OH+:3])[N:4]([CH3:5])[NH2:6]", + "image_path": "images/000123.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 3, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000124", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CC(O)N(C)N", + "wrong_smiles_mapped": "[CH3:1][CH:2]([OH:3])[N:4]([CH3:5])[NH2:6]", + "image_path": "images/000124.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (1-2) from SINGLE back to DOUBLE" + } + }, + { + "id": "000125", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "NN1CCC1=O", + "wrong_smiles_mapped": "[CH2:1]1[C:2](=[O:3])[N:4]([NH2:6])[CH2:5]1", + "image_path": "images/000125.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 1, + "atom2_map": 5 + }, + "description": "Remove spurious bond between atoms 0 and 4" + } + }, + { + "id": "000126", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CCN(C)N.O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][N:4]([CH3:5])[NH2:6].[OH2:3]", + "image_path": "images/000126.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "DOUBLE" + }, + "description": "Add back DOUBLE bond between atoms 1 and 2" + } + }, + { + "id": "000127", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CN(N)C(=O)CN", + "wrong_smiles_mapped": "[CH2:1]([C:2](=[O:3])[N:4]([CH3:5])[NH2:6])[NH2:7]", + "image_path": "images/000127.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 1, + "group_name": "NH2" + }, + "description": "Remove extra -NH2 group" + } + }, + { + "id": "000128", + "cid": "19051", + "correct_smiles": "CC(=O)N(C)N", + "wrong_smiles": "CN(N)C=O", + "wrong_smiles_mapped": "[CH:1](=[O:2])[N:3]([CH3:4])[NH2:5]", + "image_path": "images/000128.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "CH3" + }, + "description": "Add -CH3 back to anchor atom" + } + }, + { + "id": "000129", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1N5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[N:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "image_path": "images/000129.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 21, + "from_elem": "N", + "to_elem": "C" + }, + "description": "Change atom 20 from N back to C" + } + }, + { + "id": "000130", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "NC1C=C2CN3CC[C@]45c6ccccc6N6C(=O)CC(O1)[C@@H](C64)[C@H]2C[C@H]35", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH:6]([NH2:26])[CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "image_path": "images/000130.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 26, + "elem": "N" + }, + "description": "Remove extra N atom (added by corruption)" + } + }, + { + "id": "000131", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "C1=C2CN3CC[C@]45c6ccccc6N6CCC(OC1)[C@@H](C64)[C@H]2C[C@H]35", + "wrong_smiles_mapped": "[CH2:1]1[CH2:2][CH:3]2[O:4][CH2:5][CH:6]=[C:7]3[CH2:8][N:9]4[CH2:10][CH2:11][C@:12]56[c:13]7[cH:14][cH:15][cH:16][cH:17][c:18]7[N:19]1[CH:20]5[C@H:21]2[C@H:22]3[CH2:23][C@H:24]46", + "image_path": "images/000131.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "O", + "bond_type": "DOUBLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000132", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "[OH+]=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles_mapped": "[OH+:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "image_path": "images/000132.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 1, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000133", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "O=C1CC2OCCC3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH2:7][CH:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "image_path": "images/000133.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 7, + "atom2_map": 8, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (6-7) from SINGLE back to DOUBLE" + } + }, + { + "id": "000134", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "O=C1C2C3OCC=C4C2N2CC[C@]56c7ccccc7N1C5[C@H]3[C@H]4C[C@H]26", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH:3]2[CH:4]3[O:5][CH2:6][CH:7]=[C:8]4[CH:9]2[N:10]2[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]3[C@H:23]4[CH2:24][C@H:25]26", + "image_path": "images/000134.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 3, + "atom2_map": 9 + }, + "description": "Remove spurious bond between atoms 2 and 8" + } + }, + { + "id": "000135", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "C1=C2CN3CC[C@]45c6ccccc6N6CCC(OC1)[C@@H](C64)[C@H]2C[C@H]35.O", + "wrong_smiles_mapped": "[CH2:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46.[OH2:1]", + "image_path": "images/000135.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 1, + "atom2_map": 2, + "bond_type": "DOUBLE" + }, + "description": "Add back DOUBLE bond between atoms 0 and 1" + } + }, + { + "id": "000136", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "O=C1CC2(F)OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][C:4]2([F:26])[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "image_path": "images/000136.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 4, + "group_name": "F" + }, + "description": "Remove extra -F group" + } + }, + { + "id": "000137", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@@H]2[C@H]3C[C@H]46", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:4]2[O:5][CH2:6][CH:7]=[C:8]3[CH2:9][N:10]4[CH2:11][CH2:12][C@:13]56[c:14]7[cH:15][cH:16][cH:17][cH:18][c:19]7[N:20]1[CH:21]5[C@@H:22]2[C@H:23]3[CH2:24][C@H:25]46", + "image_path": "images/000137.png", + "operation": { + "type": "flip_chirality", + "params": { + "atom_map": 22 + }, + "description": "Flip chirality back at atom 21" + } + }, + { + "id": "000138", + "cid": "5979", + "correct_smiles": "O=C1CC2OCC=C3CN4CC[C@]56c7ccccc7N1C5[C@H]2[C@H]3C[C@H]46", + "wrong_smiles": "O=C1CC2C=C3CN4CC[C@]56c7ccccc7N1C5[C@H](CO2)[C@H]3C[C@H]46", + "wrong_smiles_mapped": "[O:1]=[C:2]1[CH2:3][CH:6]2[O:5][CH2:4][C@H:22]3[CH:21]4[C@:13]5([CH2:12][CH2:11][N:10]6[CH2:9][C:8](=[CH:7]2)[C@@H:23]3[CH2:24][C@H:25]65)[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[N:20]14", + "image_path": "images/000138.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 3, + "from_map": 6, + "to_map": 4 + }, + "description": "Move substituent 2 back from ring atom 5 to 3" + } + }, + { + "id": "000139", + "cid": "9591", + "correct_smiles": "FCc1ccccc1", + "wrong_smiles": "FOc1ccccc1", + "wrong_smiles_mapped": "[F:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "image_path": "images/000139.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 2, + "from_elem": "O", + "to_elem": "C" + }, + "description": "Change atom 1 from O back to C" + } + }, + { + "id": "000140", + "cid": "9591", + "correct_smiles": "FCc1ccccc1", + "wrong_smiles": "Cc1ccccc1CF", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH3:9]", + "image_path": "images/000140.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 9, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000141", + "cid": "9591", + "correct_smiles": "FCc1ccccc1", + "wrong_smiles": "Cc1ccccc1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "image_path": "images/000141.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "F", + "bond_type": "SINGLE" + }, + "description": "Add missing F atom back to anchor" + } + }, + { + "id": "000142", + "cid": "9591", + "correct_smiles": "FCc1ccccc1", + "wrong_smiles": "FCc1cc2ccc1-2", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][c:8]1-2", + "image_path": "images/000142.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 5, + "atom2_map": 8 + }, + "description": "Remove spurious bond between atoms 4 and 7" + } + }, + { + "id": "000143", + "cid": "9591", + "correct_smiles": "FCc1ccccc1", + "wrong_smiles": "CF.c1ccccc1", + "wrong_smiles_mapped": "[F:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1", + "image_path": "images/000143.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 1 and 2" + } + }, + { + "id": "000144", + "cid": "9591", + "correct_smiles": "FCc1ccccc1", + "wrong_smiles": "Cc1cccc(CF)c1", + "wrong_smiles_mapped": "[F:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH3:9])[cH:8]1", + "image_path": "images/000144.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 7, + "group_name": "CH3" + }, + "description": "Remove extra -CH3 group" + } + }, + { + "id": "000145", + "cid": "9591", + "correct_smiles": "FCc1ccccc1", + "wrong_smiles": "Cc1ccccc1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1", + "image_path": "images/000145.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "F" + }, + "description": "Add -F back to anchor atom" + } + }, + { + "id": "000146", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "ClOc1cccnc1", + "wrong_smiles_mapped": "[Cl:1][O:2][c:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "image_path": "images/000146.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 2, + "from_elem": "O", + "to_elem": "C" + }, + "description": "Change atom 1 from O back to C" + } + }, + { + "id": "000147", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "Cc1ncccc1CCl", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[CH3:9]", + "image_path": "images/000147.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 9, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000148", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "Cc1cccnc1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "image_path": "images/000148.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "Cl", + "bond_type": "SINGLE" + }, + "description": "Add missing Cl atom back to anchor" + } + }, + { + "id": "000149", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "ClCc1cc2cnc1-2", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][n:7][c:8]1-2", + "image_path": "images/000149.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 5, + "atom2_map": 8 + }, + "description": "Remove spurious bond between atoms 4 and 7" + } + }, + { + "id": "000150", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "CCl.c1ccncc1", + "wrong_smiles_mapped": "[Cl:1][CH3:2].[cH:3]1[cH:4][cH:5][cH:6][n:7][cH:8]1", + "image_path": "images/000150.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 1 and 2" + } + }, + { + "id": "000151", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "ClCc1cccnc1Br", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][n:7][c:8]1[Br:9]", + "image_path": "images/000151.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 8, + "group_name": "Br" + }, + "description": "Remove extra -Br group" + } + }, + { + "id": "000152", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "Cc1cccnc1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][cH:7]1", + "image_path": "images/000152.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "Cl" + }, + "description": "Add -Cl back to anchor atom" + } + }, + { + "id": "000153", + "cid": "18358", + "correct_smiles": "ClCc1cccnc1", + "wrong_smiles": "ClCc1ccccn1", + "wrong_smiles_mapped": "[Cl:1][CH2:2][c:6]1[cH:5][cH:4][cH:3][cH:8][n:7]1", + "image_path": "images/000153.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 2, + "from_map": 6, + "to_map": 3 + }, + "description": "Move substituent 1 back from ring atom 5 to 2" + } + }, + { + "id": "000154", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "Cc1ccc2cccc(O)c2c1C", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([OH:10])[c:11]2[c:12]1[CH3:13]", + "image_path": "images/000154.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 10, + "from_elem": "O", + "to_elem": "C" + }, + "description": "Change atom 9 from O back to C" + } + }, + { + "id": "000155", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "Cc1cc(C)c2c(C)c(C)ccc2c1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([CH3:14])[cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "image_path": "images/000155.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 14, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000156", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "Cc1cccc2cccc(C)c12", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "image_path": "images/000156.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "C", + "bond_type": "SINGLE" + }, + "description": "Add missing C atom back to anchor" + } + }, + { + "id": "000157", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "Cc1ccc2c3cc-3c(C)c2c1C", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[cH:7][c:8]-3[c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "image_path": "images/000157.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 6, + "atom2_map": 8 + }, + "description": "Remove spurious bond between atoms 5 and 7" + } + }, + { + "id": "000158", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "C.Cc1cccc2cccc(C)c12", + "wrong_smiles_mapped": "[CH4:1].[cH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "image_path": "images/000158.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 1, + "atom2_map": 2, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 0 and 1" + } + }, + { + "id": "000159", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "Cc1cc(Cl)c2cccc(C)c2c1C", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][c:4]([Cl:14])[c:5]2[cH:6][cH:7][cH:8][c:9]([CH3:10])[c:11]2[c:12]1[CH3:13]", + "image_path": "images/000159.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 4, + "group_name": "Cl" + }, + "description": "Remove extra -Cl group" + } + }, + { + "id": "000160", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "Cc1cccc2cccc(C)c12", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:10]2[c:11]1[CH3:12]", + "image_path": "images/000160.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "CH3" + }, + "description": "Add -CH3 back to anchor atom" + } + }, + { + "id": "000161", + "cid": "19753", + "correct_smiles": "Cc1ccc2cccc(C)c2c1C", + "wrong_smiles": "CC1=C(C)c2cccc(c2C)C=C1", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[C:12]([CH3:13])[c:11]2[cH:5][cH:6][cH:7][c:8]([c:9]2[CH3:10])[CH:4]=[CH:3]1", + "image_path": "images/000161.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 4, + "from_map": 8, + "to_map": 5 + }, + "description": "Move substituent 3 back from ring atom 7 to 4" + } + }, + { + "id": "000162", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CC(C=O)=CCN", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[O:7]", + "image_path": "images/000162.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 1, + "from_elem": "N", + "to_elem": "C" + }, + "description": "Change atom 0 from N back to C" + } + }, + { + "id": "000163", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CCC(C)=C(C)C=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[CH3:8]", + "image_path": "images/000163.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 8, + "elem": "C" + }, + "description": "Remove extra C atom (added by corruption)" + } + }, + { + "id": "000164", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CCC=CC=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[CH:4][CH:5]=[O:6]", + "image_path": "images/000164.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 4, + "new_elem": "C", + "bond_type": "SINGLE" + }, + "description": "Add missing C atom back to anchor" + } + }, + { + "id": "000165", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CCC=C(C)C=[OH+]", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH:3]=[C:4]([CH3:5])[CH:6]=[OH+:7]", + "image_path": "images/000165.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 7, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000166", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CCCC(C)C=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH:4]([CH3:5])[CH:6]=[O:7]", + "image_path": "images/000166.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 3, + "atom2_map": 4, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (2-3) from SINGLE back to DOUBLE" + } + }, + { + "id": "000167", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CC1=CC(C)C1=O", + "wrong_smiles_mapped": "[CH3:1][CH:2]1[CH:3]=[C:4]([CH3:5])[C:6]1=[O:7]", + "image_path": "images/000167.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 2, + "atom2_map": 6 + }, + "description": "Remove spurious bond between atoms 1 and 5" + } + }, + { + "id": "000168", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "C=C(C)C=O.CC", + "wrong_smiles_mapped": "[CH2:3]=[C:4]([CH3:5])[CH:6]=[O:7].[CH3:1][CH3:2]", + "image_path": "images/000168.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 1 and 2" + } + }, + { + "id": "000169", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CCC(Br)=C(C)C=O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][C:3](=[C:4]([CH3:5])[CH:6]=[O:7])[Br:8]", + "image_path": "images/000169.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 3, + "group_name": "Br" + }, + "description": "Remove extra -Br group" + } + }, + { + "id": "000170", + "cid": "12177", + "correct_smiles": "CCC=C(C)C=O", + "wrong_smiles": "CC=C(C)C=O", + "wrong_smiles_mapped": "[CH3:1][CH:2]=[C:3]([CH3:4])[CH:5]=[O:6]", + "image_path": "images/000170.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "CH3" + }, + "description": "Add -CH3 back to anchor atom" + } + }, + { + "id": "000171", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "Nc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles_mapped": "[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "image_path": "images/000171.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 1, + "from_elem": "N", + "to_elem": "C" + }, + "description": "Change atom 0 from N back to C" + } + }, + { + "id": "000172", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "Cc1ccc2c(c1N)C(=O)C(=O)N2", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([c:7]1[NH2:13])[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "image_path": "images/000172.png", + "operation": { + "type": "remove_atom", + "params": { + "atom_map": 13, + "elem": "N" + }, + "description": "Remove extra N atom (added by corruption)" + } + }, + { + "id": "000173", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "O=C1Nc2ccccc2C1=O", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "image_path": "images/000173.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 1, + "new_elem": "C", + "bond_type": "SINGLE" + }, + "description": "Add missing C atom back to anchor" + } + }, + { + "id": "000174", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "Cc1ccc2c(c1)C(=[OH+])C(=O)N2", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[OH+:9])[C:10](=[O:11])[NH:12]2", + "image_path": "images/000174.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 9, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000175", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "Cc1ccc2c(c1)C(=O)C(O)N2", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH:10]([OH:11])[NH:12]2", + "image_path": "images/000175.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 10, + "atom2_map": 11, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (9-10) from SINGLE back to DOUBLE" + } + }, + { + "id": "000176", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "Cc1ccc2c(c1)C(=O)CN2.O", + "wrong_smiles_mapped": "[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[CH2:10][NH:12]2.[OH2:11]", + "image_path": "images/000176.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 10, + "atom2_map": 11, + "bond_type": "DOUBLE" + }, + "description": "Add back DOUBLE bond between atoms 9 and 10" + } + }, + { + "id": "000177", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "Cc1cc2c(cc1Cl)NC(=O)C2=O", + "wrong_smiles_mapped": "[CH3:1][c:2]1[c:3]([Cl:13])[cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "image_path": "images/000177.png", + "operation": { + "type": "remove_functional_group", + "params": { + "anchor_map": 3, + "group_name": "Cl" + }, + "description": "Remove extra -Cl group" + } + }, + { + "id": "000178", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "O=C1Nc2ccccc2C1=O", + "wrong_smiles_mapped": "[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[C:7](=[O:8])[C:9](=[O:10])[NH:11]2", + "image_path": "images/000178.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "CH3" + }, + "description": "Add -CH3 back to anchor atom" + } + }, + { + "id": "000179", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "CC1=CN2C(=O)C(=O)C=C2C=C1", + "wrong_smiles_mapped": "[CH3:1][C:2]1=[CH:7][N:12]2[C:5](=[CH:6][C:8](=[O:9])[C:10]2=[O:11])[CH:4]=[CH:3]1", + "image_path": "images/000179.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 7, + "from_map": 12, + "to_map": 6 + }, + "description": "Move substituent 6 back from ring atom 11 to 5" + } + }, + { + "id": "000180", + "cid": "11840", + "correct_smiles": "Cc1ccc2c(c1)C(=O)C(=O)N2", + "wrong_smiles": "Cc1ccc2cc1C(=O)C(=O)N2", + "wrong_smiles_mapped": "[CH3:1][c:5]1[cH:4][cH:3][c:2]2[cH:7][c:6]1[C:8](=[O:9])[C:10](=[O:11])[NH:12]2", + "image_path": "images/000180.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 2, + "ring2_map": 5 + }, + "description": "Swap substituents back between ring atoms 1 and 4" + } + }, + { + "id": "000181", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN(C)C1=N[SH]2C(O)C(O)C(CO)C2O1", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][SH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "image_path": "images/000181.png", + "operation": { + "type": "change_atom_element", + "params": { + "atom_map": 6, + "from_elem": "S", + "to_elem": "C" + }, + "description": "Change atom 5 from S back to C" + } + }, + { + "id": "000182", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CC1C(O)C(O)C2N=C(N(C)C)OC12", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH3:12])[CH:13]2[O:14]1", + "image_path": "images/000182.png", + "operation": { + "type": "add_atom", + "params": { + "anchor_map": 12, + "new_elem": "O", + "bond_type": "SINGLE" + }, + "description": "Add missing O atom back to anchor" + } + }, + { + "id": "000183", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN(C)C1=[NH+]C2C(O)C(O)C(CO)C2O1", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[NH+:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "image_path": "images/000183.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 5, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000184", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN(C)C1=NC2=C(O)C(O)C(CO)C2O1", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][C:6]2=[C:7]([OH:8])[CH:9]([OH:10])[CH:11]([CH2:12][OH:13])[CH:14]2[O:15]1", + "image_path": "images/000184.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 6, + "atom2_map": 7, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (5-6) from DOUBLE back to SINGLE" + } + }, + { + "id": "000185", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN1CC2(O)C(O)C3N=C1OC3C2CO", + "wrong_smiles_mapped": "[CH3:1][N:2]1[CH2:3][C:9]2([OH:10])[CH:7]([OH:8])[CH:6]3[N:5]=[C:4]1[O:15][CH:14]3[CH:11]2[CH2:12][OH:13]", + "image_path": "images/000185.png", + "operation": { + "type": "remove_bond", + "params": { + "atom1_map": 3, + "atom2_map": 9 + }, + "description": "Remove spurious bond between atoms 2 and 8" + } + }, + { + "id": "000186", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN(C)C1=NC2C(CC(O)C2O)O1.CO", + "wrong_smiles_mapped": "[CH3:12][OH:13].[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][CH:14]2[O:15]1", + "image_path": "images/000186.png", + "operation": { + "type": "add_bond", + "params": { + "atom1_map": 11, + "atom2_map": 12, + "bond_type": "SINGLE" + }, + "description": "Add back SINGLE bond between atoms 10 and 11" + } + }, + { + "id": "000187", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN(C)C1=NC2CC(O)C(CO)C2O1", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH2:7][CH:8]([OH:9])[CH:10]([CH2:11][OH:12])[CH:13]2[O:14]1", + "image_path": "images/000187.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 7, + "group_name": "OH" + }, + "description": "Add -OH back to anchor atom" + } + }, + { + "id": "000188", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN(C)C1=NC2C(O)C(O)CC2(CO)O1", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[C:4]1=[N:5][CH:6]2[CH:7]([OH:8])[CH:9]([OH:10])[CH2:11][C:14]2([CH2:12][OH:13])[O:15]1", + "image_path": "images/000188.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 12, + "from_map": 14, + "to_map": 11 + }, + "description": "Move substituent 11 back from ring atom 13 to 10" + } + }, + { + "id": "000189", + "cid": "2095", + "correct_smiles": "CN(C)C1=NC2C(O)C(O)C(CO)C2O1", + "wrong_smiles": "CN(C)C1OC2=NC1C(O)C(O)C2CO", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[CH:14]1[CH:6]2[N:5]=[C:4]([CH:11]([CH2:12][OH:13])[CH:9]([OH:10])[CH:7]2[OH:8])[O:15]1", + "image_path": "images/000189.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 14, + "ring2_map": 4 + }, + "description": "Swap substituents back between ring atoms 13 and 3" + } + }, + { + "id": "000190", + "cid": "11812", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "wrong_smiles": "O=C(O)c1cccc(C(O)=[OH+])c1O", + "wrong_smiles_mapped": "[OH+:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "image_path": "images/000190.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 1, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000191", + "cid": "11812", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "wrong_smiles": "O=C(O)c1cccc(C(O)O)c1O", + "wrong_smiles_mapped": "[OH:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[OH:13]", + "image_path": "images/000191.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 1, + "atom2_map": 2, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (0-1) from SINGLE back to DOUBLE" + } + }, + { + "id": "000192", + "cid": "11812", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "wrong_smiles": "O=Cc1cccc(C(=O)O)c1O", + "wrong_smiles_mapped": "[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]1[OH:12]", + "image_path": "images/000192.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 2, + "group_name": "OH" + }, + "description": "Add -OH back to anchor atom" + } + }, + { + "id": "000193", + "cid": "11812", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "wrong_smiles": "O=C(O)c1cccc(O)c1C(=O)O", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[c:5]([C:9](=[O:10])[OH:11])[cH:6][cH:7][cH:8][c:12]1[OH:13]", + "image_path": "images/000193.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 9, + "from_map": 5, + "to_map": 8 + }, + "description": "Move substituent 8 back from ring atom 4 to 7" + } + }, + { + "id": "000194", + "cid": "11812", + "correct_smiles": "O=C(O)c1cccc(C(=O)O)c1O", + "wrong_smiles": "O=C(O)c1cccc(O)c1C(=O)O", + "wrong_smiles_mapped": "[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:13])[c:12]1[C:9](=[O:10])[OH:11]", + "image_path": "images/000194.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 12, + "ring2_map": 8 + }, + "description": "Swap substituents back between ring atoms 11 and 7" + } + }, + { + "id": "000195", + "cid": "16442", + "correct_smiles": "Clc1nc(Cl)nc(C(Cl)(Cl)Cl)n1", + "wrong_smiles": "Clc1ncnc(C(Cl)(Cl)Cl)n1", + "wrong_smiles_mapped": "[cH:1]1[n:2][c:3]([Cl:4])[n:5][c:6]([C:7]([Cl:8])([Cl:9])[Cl:10])[n:11]1", + "image_path": "images/000195.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "Cl" + }, + "description": "Add -Cl back to anchor atom" + } + }, + { + "id": "000196", + "cid": "1960", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "wrong_smiles": "NCCNS(=O)(=[OH+])c1cccc2c(Cl)cccc12", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[OH+:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "image_path": "images/000196.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 7, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000197", + "cid": "1960", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "wrong_smiles": "NC=CNS(=O)(=O)c1cccc2c(Cl)cccc12", + "wrong_smiles_mapped": "[NH2:1][CH:2]=[CH:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]12", + "image_path": "images/000197.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 2, + "atom2_map": 3, + "from_order": "DOUBLE", + "to_order": "SINGLE" + }, + "description": "Change bond (1-2) from DOUBLE back to SINGLE" + } + }, + { + "id": "000198", + "cid": "1960", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "wrong_smiles": "CCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "wrong_smiles_mapped": "[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]12", + "image_path": "images/000198.png", + "operation": { + "type": "add_functional_group", + "params": { + "anchor_map": 1, + "group_name": "NH2" + }, + "description": "Add -NH2 back to anchor atom" + } + }, + { + "id": "000199", + "cid": "1960", + "correct_smiles": "NCCNS(=O)(=O)c1cccc2c(Cl)cccc12", + "wrong_smiles": "NCCNS(=O)(=O)c1cccc2cc(Cl)ccc12", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][c:15]([Cl:14])[cH:16][cH:17][c:18]12", + "image_path": "images/000199.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 14, + "from_map": 15, + "to_map": 13 + }, + "description": "Move substituent 13 back from ring atom 14 to 12" + } + }, + { + "id": "000200", + "cid": "2590", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "wrong_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=[OH+]", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[OH+:43]", + "image_path": "images/000200.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 43, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000201", + "cid": "2590", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "wrong_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)O", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:23]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]12)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][CH:41]([CH3:42])[OH:43]", + "image_path": "images/000201.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 41, + "atom2_map": 43, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (40-42) from SINGLE back to DOUBLE" + } + }, + { + "id": "000202", + "cid": "2590", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "wrong_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C2(OC(C)=O)C=C3C(OC(C)=O)OC(OC(C)=O)C3C1C2", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:7]1([CH3:8])[CH:9]([CH3:10])[CH2:11][CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[C:26]2([O:27][C:28]([CH3:29])=[O:30])[CH:25]=[C:24]3[CH:23]([CH:32]1[CH2:31]2)[CH:39]([O:40][C:41]([CH3:42])=[O:43])[O:38][CH:33]3[O:34][C:35]([CH3:36])=[O:37]", + "image_path": "images/000202.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 12, + "from_map": 26, + "to_map": 23 + }, + "description": "Move substituent 11 back from ring atom 25 to 22" + } + }, + { + "id": "000203", + "cid": "2590", + "correct_smiles": "C=CC(C)=CCC1(C)C(C)CC(OC(=O)c2ccc(O)cc2)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "wrong_smiles": "C=CC(C)=CCC1(C)C(OC(=O)c2ccc(O)cc2)CC(C)C23C(=CC(OC(C)=O)CC12)C(OC(C)=O)OC3OC(C)=O", + "wrong_smiles_mapped": "[CH2:1]=[CH:2][C:3]([CH3:4])=[CH:5][CH2:6][C:23]1([CH3:8])[CH:12]([O:13][C:14](=[O:15])[c:16]2[cH:17][cH:18][c:19]([OH:20])[cH:21][cH:22]2)[CH2:11][CH:9]([CH3:10])[C:7]23[C:24](=[CH:25][CH:26]([O:27][C:28]([CH3:29])=[O:30])[CH2:31][CH:32]21)[CH:33]([O:34][C:35]([CH3:36])=[O:37])[O:38][CH:39]3[O:40][C:41]([CH3:42])=[O:43]", + "image_path": "images/000203.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 23, + "ring2_map": 7 + }, + "description": "Swap substituents back between ring atoms 22 and 6" + } + }, + { + "id": "000204", + "cid": "14279", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "wrong_smiles": "O=C1NC(=[OH+])C(Br)=C1Br", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][C:4](=[OH+:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "image_path": "images/000204.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 5, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000205", + "cid": "14279", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "wrong_smiles": "O=C1NC(O)C(Br)=C1Br", + "wrong_smiles_mapped": "[O:1]=[C:2]1[NH:3][CH:4]([OH:5])[C:6]([Br:7])=[C:8]1[Br:9]", + "image_path": "images/000205.png", + "operation": { + "type": "change_bond_order", + "params": { + "atom1_map": 4, + "atom2_map": 5, + "from_order": "SINGLE", + "to_order": "DOUBLE" + }, + "description": "Change bond (3-4) from SINGLE back to DOUBLE" + } + }, + { + "id": "000206", + "cid": "14279", + "correct_smiles": "O=C1NC(=O)C(Br)=C1Br", + "wrong_smiles": "O=C1C=C(Br)C(=O)N1Br", + "wrong_smiles_mapped": "[O:1]=[C:2]1[N:3]([Br:9])[C:4](=[O:5])[C:6]([Br:7])=[CH:8]1", + "image_path": "images/000206.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 9, + "from_map": 3, + "to_map": 8 + }, + "description": "Move substituent 8 back from ring atom 2 to 7" + } + }, + { + "id": "000207", + "cid": "5369", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "wrong_smiles": "COc1cc(-c2c(C(=O)[OH+]C)n(-c3ccc(N)cc3)c(=O)c3cc(OCc4ccccn4)ccc23)cc(OC)c1OC", + "wrong_smiles_mapped": "[CH3:1][OH+:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "image_path": "images/000207.png", + "operation": { + "type": "change_charge", + "params": { + "atom_map": 2, + "from_charge": 1, + "to_charge": 0 + }, + "description": "Change charge at atom back from +1 to +0" + } + }, + { + "id": "000208", + "cid": "5369", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "wrong_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)cc2OC)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[cH:15][c:18]2[O:16][CH3:17])[c:19]2[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]3[cH:26][cH:27][cH:28][cH:29][n:30]3)[cH:31][c:32]2[c:33](=[O:34])[n:35]1-[c:36]1[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]1", + "image_path": "images/000208.png", + "operation": { + "type": "move_substituent", + "params": { + "substituent_map": 16, + "from_map": 18, + "to_map": 15 + }, + "description": "Move substituent 15 back from ring atom 17 to 14" + } + }, + { + "id": "000209", + "cid": "5369", + "correct_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)cc2c(=O)n1-c1ccc(N)cc1", + "wrong_smiles": "COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)n(-c2ccc(N)cc2)c(=O)c2cc(OCc3ccccn3)ccc12", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[c:6]1[c:5](-[c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[cH:18]2)[n:35](-[c:36]2[cH:37][cH:38][c:39]([NH2:40])[cH:41][cH:42]2)[c:33](=[O:34])[c:32]2[c:19]1[cH:20][cH:21][c:22]([O:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][n:30]1)[cH:31]2", + "image_path": "images/000209.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 6, + "ring2_map": 5 + }, + "description": "Swap substituents back between ring atoms 5 and 4" + } + }, + { + "id": "000210", + "cid": "17089", + "correct_smiles": "COC(=O)COc1ccc(Cl)cc1C", + "wrong_smiles": "COC(=O)COc1cc(Cl)ccc1C", + "wrong_smiles_mapped": "[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:13]1[c:7]([CH3:14])[cH:8][cH:9][c:10]([Cl:11])[cH:12]1", + "image_path": "images/000210.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 7, + "ring2_map": 13 + }, + "description": "Swap substituents back between ring atoms 6 and 12" + } + }, + { + "id": "000211", + "cid": "1970", + "correct_smiles": "CNC(=O)C1OC(n2cnc3c(NCc4ccc(N)cc4)ncnc32)C(O)C1O", + "wrong_smiles": "CNC(=O)C1C(O)C(O)OC1n1cnc2c(NCc3ccc(N)cc3)ncnc21", + "wrong_smiles_mapped": "[CH3:1][NH:2][C:3](=[O:4])[CH:26]1[CH:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH2:14][c:15]4[cH:16][cH:17][c:18]([NH2:19])[cH:20][cH:21]4)[n:22][cH:23][n:24][c:25]23)[O:6][CH:5]([OH:27])[CH:28]1[OH:29]", + "image_path": "images/000211.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 26, + "ring2_map": 5 + }, + "description": "Swap substituents back between ring atoms 25 and 4" + } + }, + { + "id": "000212", + "cid": "1882", + "correct_smiles": "Cn1c(=O)c2c(ncn2CCCl)n(C)c1=O", + "wrong_smiles": "Cn1c(=O)c2c(CCCl)ncn2n(C)c1=O", + "wrong_smiles_mapped": "[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[c:6]([CH2:10][CH2:11][Cl:12])[n:7][cH:8][n:9]2[n:13]([CH3:14])[c:15]1=[O:16]", + "image_path": "images/000212.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 6, + "ring2_map": 9 + }, + "description": "Swap substituents back between ring atoms 5 and 8" + } + }, + { + "id": "000213", + "cid": "18989", + "correct_smiles": "Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)c2C)c(N)n1", + "wrong_smiles": "Cc1ncc(Cc2c(CCOP(=O)(O)OP(=O)(O)OP(=O)([O-])O)sc[n+]2C)c(N)n1", + "wrong_smiles_mapped": "[CH3:1][c:2]1[n:3][cH:4][c:5]([CH2:6][c:26]2[n+:7]([CH3:27])[cH:8][s:9][c:10]2[CH2:11][CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:18](=[O:19])([OH:20])[O:21][P:22](=[O:23])([O-:24])[OH:25])[c:28]([NH2:29])[n:30]1", + "image_path": "images/000213.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 7, + "ring2_map": 26 + }, + "description": "Swap substituents back between ring atoms 6 and 25" + } + }, + { + "id": "000214", + "cid": "17945", + "correct_smiles": "O=C(Cl)c1cc(Cl)ccc1Cl", + "wrong_smiles": "O=C(Cl)c1ccc(Cl)c(Cl)c1", + "wrong_smiles_mapped": "[O:1]=[C:2]([Cl:3])[c:6]1[cH:5][c:4]([Cl:7])[c:10]([Cl:11])[cH:9][cH:8]1", + "image_path": "images/000214.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 6, + "ring2_map": 4 + }, + "description": "Swap substituents back between ring atoms 5 and 3" + } + }, + { + "id": "000215", + "cid": "10047", + "correct_smiles": "CC12C=CC(CC1)C2(C)C", + "wrong_smiles": "CC1(C)C=CC2CCC21C", + "wrong_smiles_mapped": "[CH3:1][C:8]12[C:2]([CH3:9])([CH3:10])[CH:3]=[CH:4][CH:5]1[CH2:6][CH2:7]2", + "image_path": "images/000215.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 8, + "ring2_map": 2 + }, + "description": "Swap substituents back between ring atoms 7 and 1" + } + }, + { + "id": "000216", + "cid": "7926", + "correct_smiles": "CCOP(=S)(OCC)Oc1cc(C)[nH]n1", + "wrong_smiles": "CCOP(=S)(OCC)Oc1cc(C)n[nH]1", + "wrong_smiles_mapped": "[CH3:1][CH2:2][O:3][P:4](=[S:5])([O:6][CH2:7][CH3:8])[O:9][c:12]1[cH:11][c:10]([CH3:13])[n:15][nH:14]1", + "image_path": "images/000216.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 10, + "ring2_map": 12 + }, + "description": "Swap substituents back between ring atoms 9 and 11" + } + }, + { + "id": "000217", + "cid": "5866", + "correct_smiles": "C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO", + "wrong_smiles": "C[C@]12CC[C@@H](O)C[C@H]1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@@]2(O)C(=O)CO", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@@H:5]([OH:6])[CH2:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]1[C@@H:12]2[C:13](=[O:14])[CH2:15][C@@:16]2([CH3:17])[C@H:18]1[CH2:19][CH2:20][C@@:21]2([OH:22])[C:23](=[O:24])[CH2:25][OH:26]", + "image_path": "images/000217.png", + "operation": { + "type": "flip_chirality", + "params": { + "atom_map": 21 + }, + "description": "Flip chirality back at atom 20" + } + }, + { + "id": "000218", + "cid": "8564", + "correct_smiles": "COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(C(=O)O)c1OC", + "wrong_smiles": "COc1ccc(C(=O)Cc2c(CCN(C)C)cc3c(c2OC)OCO3)c(OC)c1C(=O)O", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][c:10]2[c:11]([CH2:12][CH2:13][N:14]([CH3:15])[CH3:16])[cH:17][c:18]3[c:19]([c:20]2[O:21][CH3:22])[O:23][CH2:24][O:25]3)[c:26]([O:31][CH3:32])[c:30]1[C:27](=[O:28])[OH:29]", + "image_path": "images/000218.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 30, + "ring2_map": 26 + }, + "description": "Swap substituents back between ring atoms 29 and 25" + } + }, + { + "id": "000219", + "cid": "9448", + "correct_smiles": "CN(C)c1ccc(N=Nc2ccccc2)cc1F", + "wrong_smiles": "CN(C)c1ccc(F)cc1N=Nc1ccccc1", + "wrong_smiles_mapped": "[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([F:18])[cH:16][c:17]1[N:8]=[N:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1", + "image_path": "images/000219.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 17, + "ring2_map": 7 + }, + "description": "Swap substituents back between ring atoms 16 and 6" + } + }, + { + "id": "000220", + "cid": "1862", + "correct_smiles": "NCC(O)c1cc(O)c(O)cc1F", + "wrong_smiles": "NCC(O)c1cc(F)c(O)cc1O", + "wrong_smiles_mapped": "[NH2:1][CH2:2][CH:3]([OH:4])[c:5]1[cH:6][c:7]([F:13])[c:9]([OH:10])[cH:11][c:12]1[OH:8]", + "image_path": "images/000220.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 7, + "ring2_map": 12 + }, + "description": "Swap substituents back between ring atoms 6 and 11" + } + }, + { + "id": "000221", + "cid": "5110", + "correct_smiles": "Nc1nccc2ccc(CN3CCC(NS(=O)(=O)c4cc5ncccc5s4)C3=O)cc12", + "wrong_smiles": "NC1=NC=Cc2ccc(CN3CCC(NS(=O)(=O)c4cc5ncccc5s4)C3=O)c1c2", + "wrong_smiles_mapped": "[NH2:1][C:2]1=[N:3][CH:4]=[CH:5][c:9]2[cH:8][cH:7][c:6]([CH2:10][N:11]3[CH2:12][CH2:13][CH:14]([NH:15][S:16](=[O:17])(=[O:18])[c:19]4[cH:20][c:21]5[n:22][cH:23][cH:24][cH:25][c:26]5[s:27]4)[C:28]3=[O:29])[c:31]1[cH:30]2", + "image_path": "images/000221.png", + "operation": { + "type": "swap_substituents", + "params": { + "ring1_map": 6, + "ring2_map": 9 + }, + "description": "Swap substituents back between ring atoms 5 and 8" + } + }, + { + "id": "000222", + "cid": "10061", + "correct_smiles": "C[C@]12CC[C@H](O)C[C@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "wrong_smiles": "C[C@]12CC[C@H](O)C[C@@H]1CCC1C2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O", + "wrong_smiles_mapped": "[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]([OH:6])[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH:11]1[CH:12]2[CH2:13][CH2:14][C@:15]2([CH3:16])[C@@H:17]([c:18]3[cH:19][cH:20][c:21](=[O:22])[o:23][cH:24]3)[CH2:25][CH2:26][C@:27]12[OH:28]", + "image_path": "images/000222.png", + "operation": { + "type": "flip_chirality", + "params": { + "atom_map": 8 + }, + "description": "Flip chirality back at atom 7" + } + }, + { + "id": "000223", + "cid": "10166", + "correct_smiles": "COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@@H]1C)C2=O", + "wrong_smiles": "COc1cccc2c1C(=O)C1=C(C[C@H](C)O[C@H]1C)C2=O", + "wrong_smiles_mapped": "[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[c:8]1[C:9](=[O:10])[C:11]1=[C:12]([CH2:13][C@H:14]([CH3:15])[O:16][C@H:17]1[CH3:18])[C:19]2=[O:20]", + "image_path": "images/000223.png", + "operation": { + "type": "flip_chirality", + "params": { + "atom_map": 17 + }, + "description": "Flip chirality back at atom 16" + } + }, + { + "id": "000224", + "cid": "14847", + "correct_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O)c1cccnc1", + "wrong_smiles": "O=C(Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO)[C@@H](OP(=O)(O)O)[C@H]1O)c1cccnc1", + "wrong_smiles_mapped": "[O:1]=[C:2]([NH:3][c:4]1[n:5][cH:6][n:7][c:8]2[c:9]1[n:10][cH:11][n:12]2[C@@H:13]1[O:14][C@@H:15]([CH2:16][OH:17])[C@@H:18]([O:19][P:20](=[O:21])([OH:22])[OH:23])[C@H:24]1[OH:25])[c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1", + "image_path": "images/000224.png", + "operation": { + "type": "flip_chirality", + "params": { + "atom_map": 15 + }, + "description": "Flip chirality back at atom 14" + } + }, + { + "id": "000225", + "cid": "14666", + "correct_smiles": "CC12CCCC[C@@H]1CCC1C2CCC2(C)C1CC[C@@H]2O", + "wrong_smiles": "CC12CCCC[C@@H]1CCC1C2CCC2(C)C1CC[C@H]2O", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:8][CH2:9][CH:10]1[CH:11]2[CH2:12][CH2:13][C:14]2([CH3:15])[CH:16]1[CH2:17][CH2:18][C@H:19]2[OH:20]", + "image_path": "images/000225.png", + "operation": { + "type": "flip_chirality", + "params": { + "atom_map": 19 + }, + "description": "Flip chirality back at atom 18" + } + }, + { + "id": "000226", + "cid": "6758", + "correct_smiles": 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back at atom 5" + } + }, + { + "id": "000228", + "cid": "15889", + "correct_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@@H]2O", + "wrong_smiles": "CC12CCC3c4ccc(O)c(F)c4CCC3C1CC[C@H]2O", + "wrong_smiles_mapped": "[CH3:1][C:2]12[CH2:3][CH2:4][CH:5]3[c:6]4[cH:7][cH:8][c:9]([OH:10])[c:11]([F:12])[c:13]4[CH2:14][CH2:15][CH:16]3[CH:17]1[CH2:18][CH2:19][C@H:20]2[OH:21]", + "image_path": "images/000228.png", + "operation": { + "type": "flip_chirality", + "params": { + "atom_map": 20 + }, + "description": "Flip chirality back at atom 19" + } + }, + { + "id": "000229", + "cid": "14926", + "correct_smiles": "CCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@@H]1O", + "wrong_smiles": "CCCCCCCCCCCC(=O)OCC(O)[C@H]1OC[C@@H](O)[C@H]1O", + "wrong_smiles_mapped": "[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[O:14][CH2:15][CH:16]([OH:17])[C@H:18]1[O:19][CH2:20][C@@H:21]([OH:22])[C@H:23]1[OH:24]", + "image_path": "images/000229.png", + "operation": { + "type": 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