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mol_edit_data / train_mol_edit_val.json
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 [
{
"id": "323f6a40-499f-4ea0-b822-3907805f3914",
"task": "delete",
"question": "Modify the molecule CC1(c2ccccc2)OOC(C)(C2CC3CCCC(C3)C2)O1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(c2ccccc2)OOC(C)(C2CC3CCCC(C3)C2)O1",
"ref_smiles": "CC1OOC(C)(C2CC3CCCC(C3)C2)O1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "a5383d3c-537b-43f1-b500-7ecfa5eec06c",
"task": "add",
"question": "Modify the molecule CC(C)=CCCC(C)[NH2+]CC1CCCCC1O by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)=CCCC(C)[NH2+]CC1CCCCC1O",
"ref_smiles": "CC(=CCCC(C)[NH2+]CC1CCCCC1O)Cc1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "9216d35d-b1e8-4f21-930d-3aa62ee7fcd1",
"task": "add",
"question": "Please add a amine to the molecule C[NH2+]C(C(=O)NC(C(=O)N(C)C(C=C(C)C(=O)OC)C(C)C)C(C)(C)C)C(C)(C)c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH2+]C(C(=O)NC(C(=O)N(C)C(C=C(C)C(=O)OC)C(C)C)C(C)(C)C)C(C)(C)c1ccccc1.",
"ref_smiles": "C[NH2+]C(C(=O)NC(C(=O)N(C)C(C=C(C)C(=O)OC)C(C)(C)N)C(C)(C)C)C(C)(C)c1ccccc1",
"add_group": "amine",
"remove_group": null
},
{
"id": "cb76a82b-29d0-4d57-8fdd-b3a914680a31",
"task": "add",
"question": "Please add a hydroxyl to the molecule CCc1nc(N)c(C)c(Sc2nc3ccccc3[nH]2)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1nc(N)c(C)c(Sc2nc3ccccc3[nH]2)n1.",
"ref_smiles": "Cc1c(N)nc(C(C)O)nc1Sc1nc2ccccc2[nH]1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "3fbc9069-ab7f-40ad-bb64-179f281541ce",
"task": "add",
"question": "Modify the molecule CCOC(=O)C(C(=O)OCC)C(CC(=O)c1ccc(N(C)C)cc1)Cc1ccc([N+](=O)[O-])cc1 by adding a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(=O)C(C(=O)OCC)C(CC(=O)c1ccc(N(C)C)cc1)Cc1ccc([N+](=O)[O-])cc1",
"ref_smiles": "CCOC(=O)C(C(=O)OCC)C(CC(=O)c1ccc(N(C)CCC=O)cc1)Cc1ccc([N+](=O)[O-])cc1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "83768c14-8ae5-4bcb-be0d-2023f605fa64",
"task": "sub",
"question": "Please substitute a halo in the molecule NC(=O)c1cccc(C[NH2+]Cc2c(Cl)ccc(Cl)c2Cl)c1 with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "NC(=O)c1cccc(C[NH2+]Cc2c(Cl)ccc(Cl)c2Cl)c1",
"ref_smiles": "NC(=O)c1cccc(C[NH2+]Cc2c([N+](=O)[O-])ccc(Cl)c2Cl)c1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "3ed54e0f-dff4-45bc-a136-d96d362f4e3b",
"task": "delete",
"question": "Please remove a benzene ring from the molecule [C-]#[N+]c1c(C)c(N=Nc2ccccc2O)c(=O)n(Cc2ccc(-c3ccccc3)cc2)c1[O-].\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "[C-]#[N+]c1c(C)c(N=Nc2ccccc2O)c(=O)n(Cc2ccc(-c3ccccc3)cc2)c1[O-].",
"ref_smiles": "[C-]#[N+]c1c(C)c(N=Nc2ccccc2O)c(=O)n(Cc2ccccc2)c1[O-]",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "2a8a61ad-d622-4814-b334-090998fd3798",
"task": "delete",
"question": "Modify the molecule CC(C)(C)c1c[nH+]c(COCc2ccccc2)[nH]1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)c1c[nH+]c(COCc2ccccc2)[nH]1",
"ref_smiles": "COCc1[nH]c(C(C)(C)C)c[nH+]1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "f3a8c818-6bdc-453e-9e8b-09ac07def527",
"task": "add",
"question": "Modify the molecule Cc1c(C(=O)NCC(=O)N2CCN(c3ccc(Cl)cc3)CC2)cnn1-c1cccc(Cl)c1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(C(=O)NCC(=O)N2CCN(c3ccc(Cl)cc3)CC2)cnn1-c1cccc(Cl)c1",
"ref_smiles": "Cc1c(C(=O)NCC(=O)N2CCN(c3ccc(Cl)c(-c4ccccc4)c3)CC2)cnn1-c1cccc(Cl)c1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "353d868e-ecb2-4979-905d-11cafe4ed46a",
"task": "delete",
"question": "Please remove a amine from the molecule CCn1ccnc(N(CCC(N)=S)CC(C)C)c1=O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCn1ccnc(N(CCC(N)=S)CC(C)C)c1=O.",
"ref_smiles": "CCn1ccnc(N(CCC=S)CC(C)C)c1=O",
"add_group": null,
"remove_group": "amine"
},
{
"id": "fa37b86b-9f42-4240-af2c-eae10087c1c3",
"task": "delete",
"question": "Modify the molecule O=C1[NH+]=C(Nc2cccc(C(=O)[O-])c2)SC1=Cc1ccc([N+](=O)[O-])o1 by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C1[NH+]=C(Nc2cccc(C(=O)[O-])c2)SC1=Cc1ccc([N+](=O)[O-])o1",
"ref_smiles": "O=C([O-])c1cccc(NC(S)Cc2ccc([N+](=O)[O-])o2)c1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "1ea49471-bcf7-43cb-81a9-fcccdb580ae3",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CC(C)c1cc(Br)cc2cc(C(O)C(C)C)oc12 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)c1cc(Br)cc2cc(C(O)C(C)C)oc12",
"ref_smiles": "CC(C)c1cc(Br)cc2cc(C(C(=O)O)C(C)C)oc12",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "1daa9b00-3948-4d7e-9e5d-d5d7e247ea73",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1cc(C)n(CCC(=O)Nc2ccnn2Cc2ccccc2Br)n1 with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C)n(CCC(=O)Nc2ccnn2Cc2ccccc2Br)n1",
"ref_smiles": "Cc1cc(C)n(CCC(=O)Nc2ccnn2Cc2ccccc2NO)n1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "a241c464-f333-4ad5-b0b4-a6400df21cd6",
"task": "sub",
"question": "Modify the molecule C[NH+](CCSc1ccc(F)cc1)C1CCC(c2ccc3[nH]c(=O)oc3c2)CC1 by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH+](CCSc1ccc(F)cc1)C1CCC(c2ccc3[nH]c(=O)oc3c2)CC1",
"ref_smiles": "C[NH+](CCSc1ccc(O)cc1)C1CCC(c2ccc3[nH]c(=O)oc3c2)CC1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "2bedf33b-ba67-4563-b81b-bdeb2ed5f591",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CC(=O)N1CCN(C(=O)CCc2ccnn2C)CC1c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)N1CCN(C(=O)CCc2ccnn2C)CC1c1ccccc1.",
"ref_smiles": "CC(=O)N1CCN(C(=O)CCc2ccnn2C)CC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "0d12938b-ce3f-4003-bb3a-76a59055f08d",
"task": "delete",
"question": "Modify the molecule O=C(NCc1ccc(F)cc1)C1CCc2[nH]c3ccccc3c2C1 by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCc1ccc(F)cc1)C1CCc2[nH]c3ccccc3c2C1",
"ref_smiles": "Fc1ccc(CC2Cc3[nH]c4ccccc4c3C2)cc1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "de08fe33-ece5-4a37-b14b-9b835b9bf39f",
"task": "sub",
"question": "Please substitute a halo in the molecule CN(Cc1ccccc1)C(=O)c1cccc(NCC(=O)Nc2ccc(I)cc2)c1 with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(Cc1ccccc1)C(=O)c1cccc(NCC(=O)Nc2ccc(I)cc2)c1",
"ref_smiles": "CN(Cc1ccccc1)C(=O)c1cccc(NCC(=O)Nc2ccc(S)cc2)c1",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "69120660-a0bd-4245-a460-561089edec65",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CC12CCC=CC1N(c1ccc(-c3ccc(N(c4ccc(-c5ccccc5)cc4)c4ccc(-c5ccccc5)cc4)cc3)cc1)c1ccccc12.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC12CCC=CC1N(c1ccc(-c3ccc(N(c4ccc(-c5ccccc5)cc4)c4ccc(-c5ccccc5)cc4)cc3)cc1)c1ccccc12.",
"ref_smiles": "CC12CCC=CC1N(c1ccc(-c3ccc(N(c4ccccc4)c4ccc(-c5ccccc5)cc4)cc3)cc1)c1ccccc12",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "419a4aea-b4d1-4d58-a823-d01094d712af",
"task": "delete",
"question": "Please remove a halo from the molecule Nc1cccc(C2CC2(NS(=O)(=O)c2ccc(-c3cc(C(F)(F)F)on3)s2)C(=O)[O-])c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Nc1cccc(C2CC2(NS(=O)(=O)c2ccc(-c3cc(C(F)(F)F)on3)s2)C(=O)[O-])c1.",
"ref_smiles": "Nc1cccc(C2CC2(NS(=O)(=O)c2ccc(-c3cc(C(F)F)on3)s2)C(=O)[O-])c1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "62869c59-4828-417a-847e-a67c75d61a57",
"task": "add",
"question": "Please add a amine to the molecule CCOCCC(=O)C(C#N)c1ccccc1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOCCC(=O)C(C#N)c1ccccc1C.",
"ref_smiles": "CCOCCC(=O)C(N)(C#N)c1ccccc1C",
"add_group": "amine",
"remove_group": null
},
{
"id": "a2cbb1b1-5c92-4862-bc94-36735df3de41",
"task": "add",
"question": "Please add a benzene ring to the molecule [NH3+]C(c1ccccc1)C(NS(=O)(=O)c1c(-c2ccccc2)cccc1-c1ccccc1)c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "[NH3+]C(c1ccccc1)C(NS(=O)(=O)c1c(-c2ccccc2)cccc1-c1ccccc1)c1ccccc1.",
"ref_smiles": "[NH3+]C(c1ccccc1)C(NS(=O)(=O)c1c(-c2ccccc2)cccc1-c1ccccc1-c1ccccc1)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "16f8b120-a279-4d38-8ac2-acc519d90677",
"task": "delete",
"question": "Please remove a amide from the molecule C[NH2+]CC1CCCN(C(=O)C2NNC(c3ccccc3)C2Br)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH2+]CC1CCCN(C(=O)C2NNC(c3ccccc3)C2Br)C1.",
"ref_smiles": "C[NH2+]CC1CCC(C2(Br)NNC2c2ccccc2)C1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "d752b95a-4d1e-42f2-84ce-ec50ee164d0b",
"task": "add",
"question": "Please add a benzene ring to the molecule Cc1cc(Br)ccc1NCCC(=O)[O-].\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(Br)ccc1NCCC(=O)[O-].",
"ref_smiles": "Cc1cc(Br)ccc1NC(CC(=O)[O-])c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "149c7b38-8216-46a8-9b3d-731925870308",
"task": "delete",
"question": "Modify the molecule CC1(C)CCCC2(C)c3cc(-c4cc(-c5ccc6c(c5)C5(C)CCCC(C)(C)C5(C)N6c5ccccc5)c5ccc6c(-c7cccc8ccccc78)cc(-c7ccc8c(c7)C7(C)CCCC(C)(C)C7(C)N8c7ccccc7)c7ccc4c5c76)ccc3N(c3ccccc3)C12C by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(C)CCCC2(C)c3cc(-c4cc(-c5ccc6c(c5)C5(C)CCCC(C)(C)C5(C)N6c5ccccc5)c5ccc6c(-c7cccc8ccccc78)cc(-c7ccc8c(c7)C7(C)CCCC(C)(C)C7(C)N8c7ccccc7)c7ccc4c5c76)ccc3N(c3ccccc3)C12C",
"ref_smiles": "CC1(C)CCCC2(C)c3cc(-c4cc(-c5cccc6ccccc56)c5ccc6c(-c7ccc8c(c7)C7(C)CCCC(C)(C)C7(C)N8c7ccccc7)cc(-c7ccc8c(c7)C7(C)CCCC(C)(C)C7(C)N8c7ccccc7)c7ccc4c5c76)ccc3NC12C",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "4df56105-3447-4582-9aad-a6a24d0eca0e",
"task": "delete",
"question": "Please remove a halo from the molecule Cc1c(C[NH+]2CCN(c3ccccc3Cl)CC2)cc(C(=O)N2CCN(c3ccccc3)CC2)n1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(C[NH+]2CCN(c3ccccc3Cl)CC2)cc(C(=O)N2CCN(c3ccccc3)CC2)n1C.",
"ref_smiles": "Cc1c(C[NH+]2CCN(c3ccccc3)CC2)cc(C(=O)N2CCN(c3ccccc3)CC2)n1C",
"add_group": null,
"remove_group": "halo"
},
{
"id": "2756a48e-3e0c-4dc7-9b15-d053e6f5e1b5",
"task": "add",
"question": "Please add a carboxyl to the molecule CC(C)C(C)NC(=O)C[NH2+]Cc1ccn(C)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)C(C)NC(=O)C[NH2+]Cc1ccn(C)n1.",
"ref_smiles": "CC(C)C(CC(=O)O)NC(=O)C[NH2+]Cc1ccn(C)n1",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "1fafee10-89b1-4642-94e0-8249d50abdd2",
"task": "delete",
"question": "Modify the molecule COc1cccc(CNC(=O)Cn2cnc(-c3ccccc3OC)cc2=O)c1 by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cccc(CNC(=O)Cn2cnc(-c3ccccc3OC)cc2=O)c1",
"ref_smiles": "COc1cccc(Cn2cnc(-c3ccccc3OC)cc2=O)c1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "a0a5513a-ffe1-4eba-8cea-6df9e6e58d18",
"task": "delete",
"question": "Please remove a benzene ring from the molecule c1cncc(-c2ccc(-c3nnc(-c4cccc(-c5nnc(-c6ccc(-c7cccnc7)nc6)s5)c4)s3)cn2)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "c1cncc(-c2ccc(-c3nnc(-c4cccc(-c5nnc(-c6ccc(-c7cccnc7)nc6)s5)c4)s3)cn2)c1.",
"ref_smiles": "c1cncc(-c2ccc(-c3nnc(-c4nnc(-c5ccc(-c6cccnc6)nc5)s4)s3)cn2)c1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "b3344e1d-e49f-431d-b436-0f8aafe94eff",
"task": "sub",
"question": "Modify the molecule CC1(C)C=C(CCO)C(=O)CC1 by substituting a hydroxyl with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(C)C=C(CCO)C(=O)CC1",
"ref_smiles": "CC1(C)C=C(CCC(=O)O)C(=O)CC1",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "f0bc73bb-36ec-41fd-a0f4-9cb701f46ed8",
"task": "delete",
"question": "Please remove a benzene ring from the molecule Cc1cccc(CNC(=O)CN2C(=O)c3cccnc3Oc3ccc(Cl)cc32)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cccc(CNC(=O)CN2C(=O)c3cccnc3Oc3ccc(Cl)cc32)c1.",
"ref_smiles": "CCNC(=O)CN1C(=O)c2cccnc2Oc2ccc(Cl)cc21",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "92d31022-30fd-4a18-a857-e880fc3a6ef3",
"task": "add",
"question": "Please add a benzene ring to the molecule CCCCC(CC)CNC(=O)C(=O)NCc1cccc(C)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCC(CC)CNC(=O)C(=O)NCc1cccc(C)c1.",
"ref_smiles": "CCC(CNC(=O)C(=O)NCc1cccc(C)c1)CC(CC)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "53054c44-45ce-4801-9ec3-d0501467d9e1",
"task": "sub",
"question": "Modify the molecule Cc1c(Cl)cccc1NC(C)c1cc2c(s1)CCCC2 by substituting a halo with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(Cl)cccc1NC(C)c1cc2c(s1)CCCC2",
"ref_smiles": "Cc1c(NC(C)c2cc3c(s2)CCCC3)cccc1C(=O)[OH]",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "93963492-f6ce-4a2f-bcd3-8590cccee659",
"task": "delete",
"question": "Modify the molecule CC(C)(C)CCCNC(=O)N1CCOCC1CC(O)c1ccco1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)CCCNC(=O)N1CCOCC1CC(O)c1ccco1",
"ref_smiles": "CC(C)(C)CCCNC(=O)N1CCOCC1CCc1ccco1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "61c51098-1ebf-4ecc-9469-c1fdb594c1cf",
"task": "add",
"question": "Please add a benzene ring to the molecule CN(Cc1ccccc1C#CC[NH3+])C(=O)C1CCC(=O)N1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(Cc1ccccc1C#CC[NH3+])C(=O)C1CCC(=O)N1.",
"ref_smiles": "CN(Cc1ccccc1C#CC[NH3+])C(=O)C1(c2ccccc2)CCC(=O)N1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "d41df9e2-34a8-4659-936d-35d50e9f88de",
"task": "sub",
"question": "Please substitute a halo in the molecule CCc1cc(Br)ccc1NC1CCCOCC1 with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1cc(Br)ccc1NC1CCCOCC1",
"ref_smiles": "CCc1cc(O)ccc1NC1CCCOCC1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "d734270e-d136-411b-93d8-3d13694209db",
"task": "delete",
"question": "Modify the molecule C=C(C(C(C)C)N(CCO)C(=O)OC(C)(C)C)[Si](C)(C)c1ccccc1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=C(C(C(C)C)N(CCO)C(=O)OC(C)(C)C)[Si](C)(C)c1ccccc1",
"ref_smiles": "C=C(C(C(C)C)N(CC)C(=O)OC(C)(C)C)[Si](C)(C)c1ccccc1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "3dd0e1b3-b61a-4cd0-94a5-08a092d686ae",
"task": "add",
"question": "Please add a hydroxyl to the molecule Cc1ccc(-c2cn3ccnc3c(Nc3cccc(CC(=O)N(C)C)c3)n2)cc1NC(=O)c1ccc(C(C)(C)C)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(-c2cn3ccnc3c(Nc3cccc(CC(=O)N(C)C)c3)n2)cc1NC(=O)c1ccc(C(C)(C)C)cc1.",
"ref_smiles": "Cc1ccc(-c2cn3ccnc3c(Nc3cccc(CC(=O)N(C)C)c3)n2)cc1NC(=O)c1ccc(C(C)(C)CO)cc1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "73180235-e5ba-4c5f-bf4c-e30d57cd62cd",
"task": "delete",
"question": "Modify the molecule Cc1ccc2cccc(Oc3ncnc(NCc4ccccc4)c3N)c2n1 by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc2cccc(Oc3ncnc(NCc4ccccc4)c3N)c2n1",
"ref_smiles": "Cc1ccc2cccc(Oc3cc(NCc4ccccc4)ncn3)c2n1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "55e336c0-eb82-48f8-be71-5e49403f636e",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1cc(Br)cc(C)c1NS(=O)(=O)c1cc(Br)sc1C with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(Br)cc(C)c1NS(=O)(=O)c1cc(Br)sc1C",
"ref_smiles": "Cc1cc(S)cc(C)c1NS(=O)(=O)c1cc(Br)sc1C",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "3cdce90b-2df9-4225-bb85-0882db448ab1",
"task": "sub",
"question": "Modify the molecule CCCn1cc(NCc2csc([N+](=O)[O-])c2)ccc1=O by substituting a nitro with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCn1cc(NCc2csc([N+](=O)[O-])c2)ccc1=O",
"ref_smiles": "CCCn1cc(NCc2csc([SH]=O)c2)ccc1=O",
"add_group": "thiol",
"remove_group": "nitro"
},
{
"id": "bc2a7f33-5308-484f-97fd-b8562fc8c973",
"task": "delete",
"question": "Please remove a amide from the molecule CCCCOC(=O)C(Cc1cnc[nH]1)NC(=O)C(NC(C)=O)C(C)C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCOC(=O)C(Cc1cnc[nH]1)NC(=O)C(NC(C)=O)C(C)C.",
"ref_smiles": "CCCCOC(=O)C(Cc1cnc[nH]1)NC(=O)CC(C)C",
"add_group": null,
"remove_group": "amide"
},
{
"id": "20eed894-439f-4352-84ee-50beb5c1a91d",
"task": "sub",
"question": "Modify the molecule CCN(Cc1nc(N)c2cnn(C)c2n1)CC(C)C#N by substituting a nitrile with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN(Cc1nc(N)c2cnn(C)c2n1)CC(C)C#N",
"ref_smiles": "CCN(Cc1nc(N)c2cnn(C)c2n1)CC(C)NO",
"add_group": "nitro",
"remove_group": "nitrile"
},
{
"id": "ab2dc671-e303-4870-b668-1038d2daabd6",
"task": "add",
"question": "Please add a benzene ring to the molecule CC(=O)NCC(CCl)OC(=O)OCc1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)NCC(CCl)OC(=O)OCc1ccccc1.",
"ref_smiles": "O=C(Cc1ccccc1)NCC(CCl)OC(=O)OCc2ccccc2",
"add_group": "benzene",
"remove_group": null
},
{
"id": "4408b57b-5599-48ce-8982-b0c83cc0753f",
"task": "delete",
"question": "Please remove a halo from the molecule CC1C[NH2+]C(C2CC2)CN1C(C)CC(F)(F)F.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1C[NH2+]C(C2CC2)CN1C(C)CC(F)(F)F.",
"ref_smiles": "CC1C[NH2+]C(C2CC2)CN1C(C)CC(F)F",
"add_group": null,
"remove_group": "halo"
},
{
"id": "75da67d9-7eac-419b-a2a2-971317de021b",
"task": "add",
"question": "Modify the molecule O=C(Cc1nc2ccccc2oc1=O)c1ccc(Cl)cc1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(Cc1nc2ccccc2oc1=O)c1ccc(Cl)cc1",
"ref_smiles": "O=C(c1ccc(Cl)cc1)C(c1ccccc1)c1nc2ccccc2oc1=O",
"add_group": "benzene",
"remove_group": null
},
{
"id": "9bbc5e62-1bc5-4ad8-9f68-f5fffd646b87",
"task": "add",
"question": "Modify the molecule O=Cc1ssc(=O)c1-c1ccccc1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=Cc1ssc(=O)c1-c1ccccc1",
"ref_smiles": "O=Cc1ssc(=O)c1-c1cccc(O)c1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "5c12a7ab-d40f-4f7a-9af3-a2e9b29c0621",
"task": "delete",
"question": "Modify the molecule O=C1C(=Cc2cc(Br)ccc2F)Cc2c(O)cccc21 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C1C(=Cc2cc(Br)ccc2F)Cc2c(O)cccc21",
"ref_smiles": "O=C1C(=Cc2ccccc2F)Cc2c(O)cccc21",
"add_group": null,
"remove_group": "halo"
},
{
"id": "42458139-45e9-4e8b-a1a3-901a46eb8404",
"task": "sub",
"question": "Modify the molecule C[NH+]=C(NCc1cccc(C(N)=O)c1)NC1CCN(c2ncccc2Cl)C1 by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH+]=C(NCc1cccc(C(N)=O)c1)NC1CCN(c2ncccc2Cl)C1",
"ref_smiles": "C[NH+]=C(NCc1cccc(C(N)=O)c1)NC1CCN(c2ncccc2O)C1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "3a0bd848-135d-4b31-8e78-596f3726b1f6",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule Nc1ccc(NCC(O)CO)cc1-c1ccco1 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Nc1ccc(NCC(O)CO)cc1-c1ccco1",
"ref_smiles": "Nc1ccc(NCC(CO)C(=O)O)cc1-c1ccco1",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "6da4c218-2bc0-49dc-8f86-9b44e9616a7c",
"task": "sub",
"question": "Please substitute a halo in the molecule CC(=O)c1c(Cl)c(=O)[nH]n1C with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)c1c(Cl)c(=O)[nH]n1C",
"ref_smiles": "CC(=O)c1c(O)c(=O)[nH]n1C",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "b3420c80-09b0-4b40-a222-cbd010aad240",
"task": "delete",
"question": "Modify the molecule O=C([O-])C1CCC(C(=O)NC2(c3cccc(Cl)c3)CC2)[NH+]1C1CC1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C([O-])C1CCC(C(=O)NC2(c3cccc(Cl)c3)CC2)[NH+]1C1CC1",
"ref_smiles": "O=C([O-])C1CCC(C(=O)NC2(Cl)CC2)[NH+]1C1CC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "09efe4a5-9f1b-4c1e-8774-36f60f187461",
"task": "delete",
"question": "Modify the molecule CC(C)Oc1nc(Cl)nc(Oc2cnn(C)c2)n1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)Oc1nc(Cl)nc(Oc2cnn(C)c2)n1",
"ref_smiles": "CC(C)Oc1ncnc(Oc2cnn(C)c2)n1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "6e8e50ad-2128-44c1-893b-106c06c894e5",
"task": "delete",
"question": "Please remove a halo from the molecule CC(C)n1nc(-c2ccccc2)cc1NC(=O)c1cnn(-c2ccccc2F)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)n1nc(-c2ccccc2)cc1NC(=O)c1cnn(-c2ccccc2F)c1.",
"ref_smiles": "CC(C)n1nc(-c2ccccc2)cc1NC(=O)c1cnn(-c2ccccc2)c1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "10227d6d-5afb-4199-b535-48bb954d45c3",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule O=C(NCC(O)COc1ccc2c(c1)OCO2)c1cc(-c2ccccc2)c(N2CCOCC2)s1 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCC(O)COc1ccc2c(c1)OCO2)c1cc(-c2ccccc2)c(N2CCOCC2)s1",
"ref_smiles": "N#CC(CNC(=O)c1cc(-c2ccccc2)c(N2CCOCC2)s1)COc1ccc2c(c1)OCO2",
"add_group": "nitrile",
"remove_group": "hydroxyl"
},
{
"id": "65bb5f8f-12ea-4146-8e16-811d1ed02073",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(Nc1ccc(Cl)cn1)c1ccc(F)cc1Br with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(Nc1ccc(Cl)cn1)c1ccc(F)cc1Br",
"ref_smiles": "O=C(Nc1ccc(S)cn1)c1ccc(F)cc1Br",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "407840ef-81ff-4e6c-bea2-dc326a66dc36",
"task": "delete",
"question": "Please remove a amine from the molecule Cc1cc(C)c(NC(=S)NCCC[NH+](C)C)c(C)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C)c(NC(=S)NCCC[NH+](C)C)c(C)c1.",
"ref_smiles": "Cc1cc(C)c(C(=S)NCCC[NH+](C)C)c(C)c1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "3c1ed9e8-178f-4732-8b8f-37f114ac9840",
"task": "add",
"question": "Modify the molecule CCOC(=O)C(C)OC(=O)OC(C#N)c1ccccc1 by adding a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(=O)C(C)OC(=O)OC(C#N)c1ccccc1",
"ref_smiles": "CCOC(=O)C(C)OC(=O)OC(S)(C#N)c1ccccc1",
"add_group": "thiol",
"remove_group": null
},
{
"id": "550d22a1-d217-41bd-98a2-93fcccb3271b",
"task": "delete",
"question": "Modify the molecule O=C(c1ncccc1O)N1CCS(=O)CC1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(c1ncccc1O)N1CCS(=O)CC1",
"ref_smiles": "O=C(c1ccccn1)N1CCS(=O)CC1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "1be8719b-9543-4d9c-9f69-376fc0ebbbe6",
"task": "delete",
"question": "Please remove a amide from the molecule CCC(C(=O)NC1CCCCC1)N(Cc1ccccc1Cl)C(=O)CN(c1ccccc1F)S(=O)(=O)c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(C(=O)NC1CCCCC1)N(Cc1ccccc1Cl)C(=O)CN(c1ccccc1F)S(=O)(=O)c1ccccc1.",
"ref_smiles": "CCC(Cc1ccccc1Cl)(C(=O)NC1CCCCC1)N(c1ccccc1F)S(=O)(=O)c1ccccc1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "59e12609-c68f-4ba3-ad91-a41895e49d2c",
"task": "add",
"question": "Modify the molecule CCN(CCNC(NCc1cccc(C(=O)NC)c1)=[NH+]C)c1cccc(C)c1 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN(CCNC(NCc1cccc(C(=O)NC)c1)=[NH+]C)c1cccc(C)c1",
"ref_smiles": "CNC(=O)c1cccc(CNC(NCCN(CCN)c2cccc(C)c2)=[NH+]C)c1",
"add_group": "amine",
"remove_group": null
},
{
"id": "da9d62ea-cf13-4444-90f1-43c2ea4d7177",
"task": "add",
"question": "Please add a carboxyl to the molecule COc1cccc(Nc2cc(-c3nc(N4CC[NH2+]CC4)c4c(C5CC5)cncc4n3)ccn2)c1F.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cccc(Nc2cc(-c3nc(N4CC[NH2+]CC4)c4c(C5CC5)cncc4n3)ccn2)c1F.",
"ref_smiles": "COc1cccc(Nc2cc(-c3nc(N4CC[NH2+]CC4)c4c(C5CC5)cncc4n3)c(C(=O)O)cn2)c1F",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "25c0f522-6340-4e18-a021-d648f9616938",
"task": "add",
"question": "Modify the molecule CC(C)n1cncc1COC1CCC(O)CC1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)n1cncc1COC1CCC(O)CC1",
"ref_smiles": "CC(C)n1cncc1COC1CCC(O)C(c2ccccc2)C1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "031949c3-9409-4557-9d41-097edb09fc21",
"task": "delete",
"question": "Modify the molecule CC(C)C(NC(=O)OCc1ccccc1)C(=O)N1C(C(=O)NC(Cc2ccccc2)C(O)C(=O)[O-])CSC1c1ccccc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)C(NC(=O)OCc1ccccc1)C(=O)N1C(C(=O)NC(Cc2ccccc2)C(O)C(=O)[O-])CSC1c1ccccc1",
"ref_smiles": "COC(=O)NC(C(=O)N1C(C(=O)NC(Cc2ccccc2)C(O)C(=O)[O-])CSC1c1ccccc1)C(C)C",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "fbfb3ad4-41ed-4426-a431-eb206ef07c1a",
"task": "sub",
"question": "Modify the molecule COCC1CCC(CO)[NH+]1CCc1ccc2c(c1)COC2=C1C(=O)Nc2ccccc21 by substituting a hydroxyl with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCC1CCC(CO)[NH+]1CCc1ccc2c(c1)COC2=C1C(=O)Nc2ccccc21",
"ref_smiles": "COCC1CCC(CC#N)[NH+]1CCc1ccc2c(c1)COC2=C1C(=O)Nc2ccccc21",
"add_group": "nitrile",
"remove_group": "hydroxyl"
},
{
"id": "dbb77e04-4c06-426e-b3ab-9e181ac213f4",
"task": "delete",
"question": "Please remove a benzene ring from the molecule COc1cccc(NC(=O)NCc2nc3ccccc3[nH]2)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cccc(NC(=O)NCc2nc3ccccc3[nH]2)c1.",
"ref_smiles": "CONC(=O)NCc1nc2ccccc2[nH]1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "e78c0820-6611-4ff3-bb8f-76551e135b09",
"task": "add",
"question": "Modify the molecule COC(=O)C(Nc1cccnc1C(N)=S)c1ccccc1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)C(Nc1cccnc1C(N)=S)c1ccccc1",
"ref_smiles": "COC(=O)C(Nc1cccnc1C(N)=S)c1cccc(O)c1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "3321b055-acfd-4f27-9997-854ce2242626",
"task": "delete",
"question": "Please remove a halo from the molecule CCc1cccc2c(I)c(SC)sc12.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1cccc2c(I)c(SC)sc12.",
"ref_smiles": "CCc1cccc2cc(SC)sc12",
"add_group": null,
"remove_group": "halo"
},
{
"id": "54664f03-4b3e-4a42-88f6-918a623eb3d0",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1cc(=O)n(CC(=O)NCc2ccccc2Br)c(N2CCOCC2)n1 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(=O)n(CC(=O)NCc2ccccc2Br)c(N2CCOCC2)n1",
"ref_smiles": "Cc1cc(=O)n(CC(=O)NCc2ccccc2C(=O)O)c(N2CCOCC2)n1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "9412c25e-d0b1-4715-a3ea-1e675fddda29",
"task": "delete",
"question": "Modify the molecule Cc1nccn2c(C3CCN(C)C(=O)C3)nc(Br)c12 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nccn2c(C3CCN(C)C(=O)C3)nc(Br)c12",
"ref_smiles": "Cc1nccn2c(C3CCN(C)C(=O)C3)ncc12",
"add_group": null,
"remove_group": "halo"
},
{
"id": "23105a3a-f4d7-4101-bea3-d417ae029111",
"task": "delete",
"question": "Please remove a halo from the molecule C=NOc1ccnc(Cl)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=NOc1ccnc(Cl)n1.",
"ref_smiles": "C=NOc1ccncn1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "8b73f189-be80-4b6f-82a2-9ceb9e4cc6eb",
"task": "add",
"question": "Please add a hydroxyl to the molecule COCc1nnc2n1Cc1c(C)ncn1-c1ccc(OC)cc1-2.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCc1nnc2n1Cc1c(C)ncn1-c1ccc(OC)cc1-2.",
"ref_smiles": "COc1ccc2c(c1)-c1nnc(COCO)n1Cc1c(C)ncn1-2",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "d645f74a-f14d-4cfe-8674-0bf63e8da3dd",
"task": "sub",
"question": "Please substitute a halo in the molecule CCN(CC)C(=O)c1cccc(NC(=O)C(C)[NH+]2CCC(C(=O)NCC(=O)Nc3ccc(NC(C)=O)c(Cl)c3)CC2)c1C with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN(CC)C(=O)c1cccc(NC(=O)C(C)[NH+]2CCC(C(=O)NCC(=O)Nc3ccc(NC(C)=O)c(Cl)c3)CC2)c1C",
"ref_smiles": "CCN(CC)C(=O)c1cccc(NC(=O)C(C)[NH+]2CCC(C(=O)NCC(=O)Nc3ccc(NC(C)=O)c(C#N)c3)CC2)c1C",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "2876c2e9-bd69-4eef-8fd1-2759d3350c02",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1cc(C=C2C(=O)NC(=O)N(c3cccc(Cl)c3)C2=O)c(C)n1-c1ccccc1C(=O)[O-] with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C=C2C(=O)NC(=O)N(c3cccc(Cl)c3)C2=O)c(C)n1-c1ccccc1C(=O)[O-]",
"ref_smiles": "Cc1cc(C=C2C(=O)NC(=O)N(c3cccc(C(=O)[OH])c3)C2=O)c(C)n1-c1ccccc1C(=O)[O-]",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "18e29158-8c91-480f-a66a-c3b26945b795",
"task": "add",
"question": "Modify the molecule COC(=O)c1ccc(N)c(OCOCC(F)(F)F)c1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)c1ccc(N)c(OCOCC(F)(F)F)c1",
"ref_smiles": "Nc1ccc(C(=O)OCc2ccccc2)cc1OCOCC(F)(F)F",
"add_group": "benzene",
"remove_group": null
},
{
"id": "a0a0d182-c614-4a54-9d05-7fc4cb856795",
"task": "delete",
"question": "Please remove a benzene ring from the molecule C=CCn1c(=NS(=O)(=O)c2ccc(OC)cc2)sc2cc(OCC)ccc21.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CCn1c(=NS(=O)(=O)c2ccc(OC)cc2)sc2cc(OCC)ccc21.",
"ref_smiles": "C=CCn1c(=NS(=O)(=O)OC)sc2cc(OCC)ccc21",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "ad2da0a0-c792-4377-bf51-b78134162013",
"task": "delete",
"question": "Modify the molecule O=C(C1CN(c2ncc(C(F)(F)F)cc2Cl)C1)N1CCCC1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(C1CN(c2ncc(C(F)(F)F)cc2Cl)C1)N1CCCC1",
"ref_smiles": "O=C(C1CN(c2ncc(C(F)F)cc2Cl)C1)N1CCCC1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "7c26b3e0-4dc8-419e-9e5f-600e4b935410",
"task": "add",
"question": "Please add a benzene ring to the molecule O=C(NCc1cccnc1)C1CCN(c2nccc3nc(NCc4ccccc4Cl)ncc23)CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCc1cccnc1)C1CCN(c2nccc3nc(NCc4ccccc4Cl)ncc23)CC1.",
"ref_smiles": "O=C(NC(c1ccccc1)c1cccnc1)C1CCN(c2nccc3nc(NCc4ccccc4Cl)ncc23)CC1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "6f4c54ac-049e-4090-ab9f-6fb054262178",
"task": "add",
"question": "Modify the molecule Cc1ccc(C(=O)N2CCOCC2c2[nH]ncc2S(C)(=O)=O)s1 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(C(=O)N2CCOCC2c2[nH]ncc2S(C)(=O)=O)s1",
"ref_smiles": "Cc1ccc(C(=O)N2CC(C(=O)O)OCC2c2[nH]ncc2S(C)(=O)=O)s1",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "87ff0adb-dc71-486d-a789-9fba69c664bd",
"task": "delete",
"question": "Modify the molecule Cc1cc(C2CCC[NH2+]C2)cc(Br)c1OCc1ccccc1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C2CCC[NH2+]C2)cc(Br)c1OCc1ccccc1",
"ref_smiles": "Cc1cc(C2CCC[NH2+]C2)ccc1OCc1ccccc1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "fdf003f0-9cd8-4ac4-803c-a2cfcff1a1b6",
"task": "add",
"question": "Please add a benzene ring to the molecule CCN(CC(C)C)S(=O)(=O)c1c(Cl)nc2sccn12.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN(CC(C)C)S(=O)(=O)c1c(Cl)nc2sccn12.",
"ref_smiles": "CCN(CC(C)C)S(=O)(=O)c1c(Cl)nc2sc(-c3ccccc3)cn12",
"add_group": "benzene",
"remove_group": null
},
{
"id": "4d5eaef3-fdbb-4a48-9e4b-a910d30688e6",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CC[NH+]1CCc2c(c(CN(C3CC3)S(=O)(=O)c3ccccc3C#N)nn2-c2cccc(F)c2)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC[NH+]1CCc2c(c(CN(C3CC3)S(=O)(=O)c3ccccc3C#N)nn2-c2cccc(F)c2)C1.",
"ref_smiles": "CC[NH+]1CCc2c(c(CN(C3CC3)S(=O)(=O)C#N)nn2-c2cccc(F)c2)C1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "b1d4b038-5921-430d-b538-2109c0c4ad44",
"task": "add",
"question": "Modify the molecule CC(C)(C)c1cc(O)c2c(c1)OC(C)(C)C1CC=C(CO)CC21 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)c1cc(O)c2c(c1)OC(C)(C)C1CC=C(CO)CC21",
"ref_smiles": "CC(C)(C)c1cc(O)c2c(c1)OC(C)(C)C1CC=C(CO)C(O)C21",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "7da26799-6d55-492c-b384-eb4b15eae52b",
"task": "add",
"question": "Modify the molecule O=C(Nc1nc(-c2cc(O)ccc2O)cs1)c1c(F)cccc1F by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(Nc1nc(-c2cc(O)ccc2O)cs1)c1c(F)cccc1F",
"ref_smiles": "O=C(Nc1nc(-c2cc(O)cc(O)c2O)cs1)c1c(F)cccc1F",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "a3b2ab31-56d1-4b12-bb9c-ca28505984af",
"task": "delete",
"question": "Please remove a amine from the molecule c1ccc(C2CNCC3(CCCC3)[NH2+]2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "c1ccc(C2CNCC3(CCCC3)[NH2+]2)cc1.",
"ref_smiles": "c1ccc(C2CCC3(CCCC3)[NH2+]2)cc1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "74c02f3b-f0a6-4436-9eab-e3be5cbdc384",
"task": "sub",
"question": "Modify the molecule CCC=Cc1nc2cc(F)ccc2cc1C(C)N1C(=O)c2ccccc2C1=O by substituting a halo with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC=Cc1nc2cc(F)ccc2cc1C(C)N1C(=O)c2ccccc2C1=O",
"ref_smiles": "CCC=Cc1nc2cc([N+](=O)[O-])ccc2cc1C(C)N1C(=O)c2ccccc2C1=O",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "cdf70f8d-270c-4226-acba-4f12127432a4",
"task": "delete",
"question": "Please remove a amide from the molecule CC(C)(C)C=CC(=O)Nc1ccc(Cl)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)C=CC(=O)Nc1ccc(Cl)cc1.",
"ref_smiles": "CC(C)(C)Cc1ccc(Cl)cc1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "933b5adf-e051-4087-8291-930d2828517a",
"task": "delete",
"question": "Modify the molecule CCc1ccc(-c2c[n+]3c(n2-c2ccc(Cl)cc2)CCCCC3)cc1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1ccc(-c2c[n+]3c(n2-c2ccc(Cl)cc2)CCCCC3)cc1",
"ref_smiles": "CCc1ccc(-c2c[n+]3c(n2-c2ccccc2)CCCCC3)cc1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "853f922d-9b15-4bad-abf6-8201621acbc9",
"task": "add",
"question": "Please add a benzene ring to the molecule COC(=O)N1CCN(C(=O)Nc2ccc([N+](=O)[O-])cc2)CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)N1CCN(C(=O)Nc2ccc([N+](=O)[O-])cc2)CC1.",
"ref_smiles": "COC(=O)N1CCN(C(=O)Nc2ccc([N+](=O)[O-])cc2-c2ccccc2)CC1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "aa849b07-3c39-41c9-b033-341d33aa30e0",
"task": "delete",
"question": "Modify the molecule O=C(CN(C(=O)c1ccco1)C1CC1)N1CCCN(c2ccc(-c3ccc(F)cc3)nn2)CC1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(CN(C(=O)c1ccco1)C1CC1)N1CCCN(c2ccc(-c3ccc(F)cc3)nn2)CC1",
"ref_smiles": "O=C(CN(C(=O)c1ccco1)C1CC1)N1CCCN(c2ccc(nn2)CC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "1f8a35d9-431f-4c91-8b12-9a6d0cd5a27a",
"task": "delete",
"question": "Modify the molecule CC(C)CCCOC1CCC(C#N)(NC(C)C)C1 by removing a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)CCCOC1CCC(C#N)(NC(C)C)C1",
"ref_smiles": "CC(C)CCCOC1CCC(NC(C)C)C1",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "3ff3f9c7-1372-470c-a1ee-8116ccc0dcc3",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CCCc1sc(C([NH3+])CSCCCO)nc1C with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCc1sc(C([NH3+])CSCCCO)nc1C",
"ref_smiles": "CCCc1sc(C([NH3+])CSCCCC(=O)O)nc1C",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "984a8263-65a4-437a-a64e-647a56a0d4d5",
"task": "delete",
"question": "Modify the molecule C=C(CO)CCC(C)NS(=O)(=O)c1ccc(C)cc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=C(CO)CCC(C)NS(=O)(=O)c1ccc(C)cc1",
"ref_smiles": "C=C(CO)CCC(C)NS(C)(=O)=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "7309fea3-ebb8-4c44-abf7-95dc16c0b645",
"task": "add",
"question": "Please add a carboxyl to the molecule CCN(CCC(=O)OC)c1nccc(C)c1[N+](=O)[O-].\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN(CCC(=O)OC)c1nccc(C)c1[N+](=O)[O-].",
"ref_smiles": "CCN(CCC(=O)OCC(=O)O)c1nccc(C)c1[N+](=O)[O-]",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "467b5aee-834d-40f3-9ef7-ba50b72a1870",
"task": "delete",
"question": "Please remove a amine from the molecule Cc1ccc(-c2cnccc2-c2cnc(Nc3cccc(F)c3)s2)c(Cl)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(-c2cnccc2-c2cnc(Nc3cccc(F)c3)s2)c(Cl)c1.",
"ref_smiles": "Cc1ccc(-c2cnccc2-c2cnc(-c3cccc(F)c3)s2)c(Cl)c1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "de98a54d-cab0-4295-bad7-ad1cec5bd318",
"task": "delete",
"question": "Please remove a amide from the molecule O=C(C[NH+]1CCC(c2cncc(Nc3ccc(F)cn3)n2)CC1)Nc1ccccc1C(F)(F)F.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(C[NH+]1CCC(c2cncc(Nc3ccc(F)cn3)n2)CC1)Nc1ccccc1C(F)(F)F.",
"ref_smiles": "Fc1ccc(Nc2cncc(C3CC[NH+](c4ccccc4C(F)(F)F)CC3)n2)nc1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "22c5fdb5-4c98-442a-aa34-446c27f31875",
"task": "delete",
"question": "Modify the molecule CCNC(c1ccccc1)(C(C)C)C(F)F by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCNC(c1ccccc1)(C(C)C)C(F)F",
"ref_smiles": "CCC(c1ccccc1)(C(C)C)C(F)F",
"add_group": null,
"remove_group": "amine"
},
{
"id": "6b42e624-21d3-477c-843e-e93296eb4090",
"task": "delete",
"question": "Please remove a benzene ring from the molecule O=C([O-])c1c(Br)nnn1Cc1cccc(F)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C([O-])c1c(Br)nnn1Cc1cccc(F)c1.",
"ref_smiles": "O=C([O-])c1c(Br)nnn1CF",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "83415959-5ae9-4abb-91aa-cb5a810b6501",
"task": "sub",
"question": "Please substitute a halo in the molecule CCOC(=O)c1ccc(C)c(NC(=O)c2ccc(F)cc2)c1 with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(=O)c1ccc(C)c(NC(=O)c2ccc(F)cc2)c1",
"ref_smiles": "CCOC(=O)c1ccc(C)c(NC(=O)c2ccc(NO)cc2)c1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "c2f3dbad-68b5-44d5-ae10-6b52eb4b670c",
"task": "delete",
"question": "Please remove a benzene ring from the molecule COC(=O)C=Cc1ccc(-c2nc(-c3ccc4oc5c(C(=O)OC)cccc5c4c3)cs2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)C=Cc1ccc(-c2nc(-c3ccc4oc5c(C(=O)OC)cccc5c4c3)cs2)cc1.",
"ref_smiles": "COC(=O)C=Cc1nc(-c2ccc3oc4c(C(=O)OC)cccc4c3c2)cs1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "abab656d-2218-4a81-8ec5-b5441b584b63",
"task": "delete",
"question": "Modify the molecule COc1cccc(OCC(=O)C(Cc2c[nH]c3ccccc23)C([NH3+])NC(=O)CCc2ccccc2OC)c1 by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cccc(OCC(=O)C(Cc2c[nH]c3ccccc23)C([NH3+])NC(=O)CCc2ccccc2OC)c1",
"ref_smiles": "COc1cccc(OCC(=O)C(Cc2c[nH]c3ccccc23)C([NH3+])Cc2ccccc2OC)c1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "2c5e8897-9c82-499c-87a4-d3323300fd7e",
"task": "sub",
"question": "Modify the molecule Cc1c(F)cc(F)c(Bc2c(F)cc(F)c(C)c2F)c1F by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(F)cc(F)c(Bc2c(F)cc(F)c(C)c2F)c1F",
"ref_smiles": "Cc1c(O)cc(F)c(Bc2c(F)cc(F)c(C)c2F)c1F",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "1d8df281-02bf-4805-9012-6e985e50d56b",
"task": "add",
"question": "Please add a benzene ring to the molecule O=C(NCc1ccc(OCc2cccnc2)cc1)c1cc(Cl)nc(Cl)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCc1ccc(OCc2cccnc2)cc1)c1cc(Cl)nc(Cl)c1.",
"ref_smiles": "O=C(NCc1ccc(OCc2cncc(-c3ccccc3)c2)cc1)c1cc(Cl)nc(Cl)c1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "ddebdf69-70ef-4062-bbb5-be6b2dc13189",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule O=C(CCn1nc(-c2ccccc2)cc1-c1ccccc1)N=Nc1c(O)[nH]c2ccccc12 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(CCn1nc(-c2ccccc2)cc1-c1ccccc1)N=Nc1c(O)[nH]c2ccccc12",
"ref_smiles": "N#Cc1[nH]c2ccccc2c1N=NC(=O)CCn1nc(-c2ccccc2)cc1-c1ccccc1",
"add_group": "nitrile",
"remove_group": "hydroxyl"
},
{
"id": "0cce25fd-4dfe-4fc3-a381-7c2cfa708bd9",
"task": "add",
"question": "Modify the molecule CC(CCNc1ccc2c(c1)CCC2)c1ccccc1 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(CCNc1ccc2c(c1)CCC2)c1ccccc1",
"ref_smiles": "CC(c1ccccc1)C(CNc1ccc2c(c1)CCC2)C(=O)O",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "3b1da969-a5c3-405e-b137-e013b1c7a4ce",
"task": "add",
"question": "Please add a benzene ring to the molecule O=C(CCCN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)NCC1CCCO1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(CCCN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)NCC1CCCO1.",
"ref_smiles": "O=C(CCC(c1ccccc1)N1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)NCC1CCCO1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "19952cc5-b421-44c3-bbe7-2ad8aeb5b664",
"task": "sub",
"question": "Modify the molecule CCc1cnc(C(O)C2CCC2)s1 by substituting a hydroxyl with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1cnc(C(O)C2CCC2)s1",
"ref_smiles": "CCc1cnc(C(C(=O)O)C2CCC2)s1",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "e17f6201-40f1-4702-9062-d928e2c439ad",
"task": "delete",
"question": "Please remove a hydroxyl from the molecule COCC(C)OCC(O)C[NH+]1CCSCC1C(=O)[O-].\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCC(C)OCC(O)C[NH+]1CCSCC1C(=O)[O-].",
"ref_smiles": "COCC(C)OCCC[NH+]1CCSCC1C(=O)[O-]",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "52b64480-e4d3-4ec6-9286-b84087cd0adc",
"task": "sub",
"question": "Please substitute a halo in the molecule C[NH2+]Cc1csc(-c2ccc(Cl)cc2Cl)c1 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH2+]Cc1csc(-c2ccc(Cl)cc2Cl)c1",
"ref_smiles": "C[NH2+]Cc1csc(-c2ccc(C#N)cc2Cl)c1",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "626e7c5a-a797-4ea5-972d-f078b9b102de",
"task": "delete",
"question": "Please remove a halo from the molecule CCC(C(=O)c1ccc(Cl)cc1)C(c1ccc(Br)cc1)C(C(=O)Nc1ccc(OC)cc1)C(=O)OC.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(C(=O)c1ccc(Cl)cc1)C(c1ccc(Br)cc1)C(C(=O)Nc1ccc(OC)cc1)C(=O)OC.",
"ref_smiles": "CCC(C(=O)c1ccccc1)C(c1ccc(Br)cc1)C(C(=O)Nc1ccc(OC)cc1)C(=O)OC",
"add_group": null,
"remove_group": "halo"
},
{
"id": "edc0f2e5-1336-48b7-996e-f6975ef72331",
"task": "add",
"question": "Please add a aldehyde to the molecule CS(=O)(=O)CCOc1cncc([B-](F)(F)F)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CS(=O)(=O)CCOc1cncc([B-](F)(F)F)c1.",
"ref_smiles": "CS(=O)(=O)CCOc1cnc(CC=O)c([B-](F)(F)F)c1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "7f1ad3c1-d64b-43d7-860b-308eeb765e62",
"task": "add",
"question": "Please add a hydroxyl to the molecule Cc1ccc(C[NH2+]CC(=O)NCC#N)cn1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(C[NH2+]CC(=O)NCC#N)cn1.",
"ref_smiles": "Cc1cc(O)c(C[NH2+]CC(=O)NCC#N)cn1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "a4abf303-b3a9-4391-bc83-89dceef46402",
"task": "sub",
"question": "Modify the molecule COc1ccc(C(NN)c2cnnn2C)cc1F by substituting a halo with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(C(NN)c2cnnn2C)cc1F",
"ref_smiles": "COc1ccc(C(NN)c2cnnn2C)cc1[N+](=O)[O-]",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "7abfe9d0-40ce-430d-b0d4-b2b7e853d51c",
"task": "add",
"question": "Modify the molecule Cc1ccc(C(=O)NN2C(=O)C(=Cc3cn(Cc4ccc(F)cc4Cl)c4ccccc34)SC2=S)c(Cl)c1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(C(=O)NN2C(=O)C(=Cc3cn(Cc4ccc(F)cc4Cl)c4ccccc34)SC2=S)c(Cl)c1",
"ref_smiles": "Cc1ccc(C(=O)NN2C(=O)C(=Cc3cn(Cc4ccc(F)c(-c5ccccc5)c4Cl)c4ccccc34)SC2=S)c(Cl)c1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "d9b30d79-4e6c-49f3-86a9-99133b2d49af",
"task": "add",
"question": "Modify the molecule O=C(NC1CCN(C(=O)NCc2ccccn2)CC1)c1ccccc1C(F)(F)F by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NC1CCN(C(=O)NCc2ccccn2)CC1)c1ccccc1C(F)(F)F",
"ref_smiles": "O=C(NC1CCN(C(=O)NCc2ccccn2)CC1)c1ccc(-c2ccccc2)cc1C(F)(F)F",
"add_group": "benzene",
"remove_group": null
},
{
"id": "078bf609-0974-4223-870b-2fae874111e4",
"task": "delete",
"question": "Please remove a amine from the molecule CCN=CC(C=N)c1cc(C(=N)c2ccc(C)c(N3CC[NH2+]CC3)n2)c(N)cn1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN=CC(C=N)c1cc(C(=N)c2ccc(C)c(N3CC[NH2+]CC3)n2)c(N)cn1.",
"ref_smiles": "CCN=CC(C=N)c1cc(C(=N)c2ccc(C)c(N3CC[NH2+]CC3)n2)ccn1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "07addc0f-268f-4947-bfc3-9313daf2d030",
"task": "add",
"question": "Please add a benzene ring to the molecule Cc1nccn1CC1CCCN1C(=O)NCCN1c2ccccc2CC1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nccn1CC1CCCN1C(=O)NCCN1c2ccccc2CC1C.",
"ref_smiles": "Cc1nccn1CC1CCCN1C(=O)NCCN1c2c(cccc2-c2ccccc2)CC1C",
"add_group": "benzene",
"remove_group": null
},
{
"id": "65dea3c1-dcd8-4d67-9e00-477f50ab651c",
"task": "sub",
"question": "Modify the molecule COc1cc(C(C)=O)ccc1OCC(=O)Nc1ccc(OC)c(S(=O)(=O)Nc2ccccc2Cl)c1 by substituting a halo with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cc(C(C)=O)ccc1OCC(=O)Nc1ccc(OC)c(S(=O)(=O)Nc2ccccc2Cl)c1",
"ref_smiles": "COc1cc(C(C)=O)ccc1OCC(=O)Nc1ccc(OC)c(S(=O)(=O)Nc2ccccc2NO2)c1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "bebfde1b-0153-44c3-9ad7-2e1630b1aa22",
"task": "delete",
"question": "Modify the molecule COCCC(C)(C)C[NH2+]Cc1cccc(Br)c1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCCC(C)(C)C[NH2+]Cc1cccc(Br)c1",
"ref_smiles": "COCCC(C)(C)C[NH2+]Cc1ccccc1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "36514e85-c9f9-4b44-ac30-5defc12ed0c9",
"task": "add",
"question": "Modify the molecule CCC([NH3+])C(=O)NCCCCOC by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC([NH3+])C(=O)NCCCCOC",
"ref_smiles": "COCCCCNC(=O)C([NH3+])C(C)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "38e6e53f-2e60-4811-9026-df2be6d14791",
"task": "delete",
"question": "Please remove a nitrile from the molecule COc1ccc(CN(Cc2ccc(OC)cc2)c2cc(Nc3ccc(C#N)nc3F)cc3c2ncn3C)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(CN(Cc2ccc(OC)cc2)c2cc(Nc3ccc(C#N)nc3F)cc3c2ncn3C)cc1.",
"ref_smiles": "COc1ccc(CN(Cc2ccc(OC)cc2)c2cc(Nc3cccnc3F)cc3c2ncn3C)cc1",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "a4377dd8-3f43-4ef1-b534-549c1a209871",
"task": "delete",
"question": "Modify the molecule O=CC1CCc2nnn(N3CC4(CCN(C(=O)OCc5ccc(OCC(F)(F)F)c(F)c5)CC4)C3)c2C1 by removing a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=CC1CCc2nnn(N3CC4(CCN(C(=O)OCc5ccc(OCC(F)(F)F)c(F)c5)CC4)C3)c2C1",
"ref_smiles": "O=C(OCc1ccc(OCC(F)(F)F)c(F)c1)N1CCC2(CC1)CN(n1nnc3c1CCC3)C2",
"add_group": null,
"remove_group": "aldehyde"
},
{
"id": "d6aa69e7-ed14-4224-b041-9418d1f53563",
"task": "delete",
"question": "Modify the molecule CCCCc1nnc(SCc2ccccc2F)n1N=Cc1cccc(OCc2ccc(Cl)cc2)c1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCc1nnc(SCc2ccccc2F)n1N=Cc1cccc(OCc2ccc(Cl)cc2)c1",
"ref_smiles": "CCCCc1nnc(SCc2ccccc2F)n1N=Cc1cccc(OCc2ccccc2)c1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "64705bf4-d504-4f8c-aaa8-9079c86aaa3d",
"task": "add",
"question": "Modify the molecule CCNC(=O)Nc1cccc(NC(=O)CCCOc2ccc3c(c2)CCC(=O)N3)c1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCNC(=O)Nc1cccc(NC(=O)CCCOc2ccc3c(c2)CCC(=O)N3)c1",
"ref_smiles": "CCNC(=O)Nc1cccc(NC(=O)CCC(Oc2ccc3c(c2)CCC(=O)N3)c2ccccc2)c1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "4b6abd87-a19f-4318-ac22-d0be6757be90",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(-c2ccc(C(F)(F)F)cc2F)n2ccccc12 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(-c2ccc(C(F)(F)F)cc2F)n2ccccc12",
"ref_smiles": "O=C(NC12CC3CC(CC(C3)C1)C2)c1nc(-c2ccc(C(F)(F)C(=O)O)cc2F)n2ccccc12",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "963edb15-72cd-464a-abe1-b490474f22e5",
"task": "delete",
"question": "Modify the molecule CN(Cc1cc(F)cc2cccnc12)c1c(N)n(Cc2ccccc2)c(=O)[nH]c1=O by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(Cc1cc(F)cc2cccnc12)c1c(N)n(Cc2ccccc2)c(=O)[nH]c1=O",
"ref_smiles": "CN(Cc1cc(F)cc2cccnc12)c1cn(Cc2ccccc2)c(=O)[nH]c1=O",
"add_group": null,
"remove_group": "amine"
},
{
"id": "65ca5436-5c13-47e2-ba8b-7741e500f0bf",
"task": "add",
"question": "Modify the molecule O=C1NC(c2ccc(Cl)cc2)Nc2scc(-c3ccccc3)c21 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C1NC(c2ccc(Cl)cc2)Nc2scc(-c3ccccc3)c21",
"ref_smiles": "O=C(O)c1sc2c(c1-c1ccccc1)C(=O)NC(c1ccc(Cl)cc1)N2",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "1c75346f-2d83-46a5-bb65-a33c4db134c9",
"task": "add",
"question": "Modify the molecule CCC(Sc1cccc(NC(=O)c2cccs2)c1)C(=O)Nc1ccccc1F by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(Sc1cccc(NC(=O)c2cccs2)c1)C(=O)Nc1ccccc1F",
"ref_smiles": "CCC(Sc1cc(NC(=O)c2cccs2)ccc1-c1ccccc1)C(=O)Nc1ccccc1F",
"add_group": "benzene",
"remove_group": null
},
{
"id": "97eaadf1-daad-41c7-8557-b5c8959e298d",
"task": "sub",
"question": "Please substitute a halo in the molecule Cn1ncnc1CC(C[NH3+])Cc1ccc(Cl)cc1 with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cn1ncnc1CC(C[NH3+])Cc1ccc(Cl)cc1",
"ref_smiles": "Cn1ncnc1CC(C[NH3+])Cc1ccc(S)cc1",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "690f5bfe-c8b1-4408-a589-8fd9ebe17ae4",
"task": "add",
"question": "Modify the molecule CC(C)(O)CNc1nc(-c2ccccc2CO)cn2c(-c3ccc(C(N)=O)c(C4CC4)c3)c[nH+]c12 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(O)CNc1nc(-c2ccccc2CO)cn2c(-c3ccc(C(N)=O)c(C4CC4)c3)c[nH+]c12",
"ref_smiles": "CC(C)(O)CNc1nc(-c2ccc(-c3ccccc3)cc2CO)cn2c(-c3ccc(C(N)=O)c(C4CC4)c3)c[nH+]c12",
"add_group": "benzene",
"remove_group": null
},
{
"id": "3b7a6d07-aa99-4e3d-933a-6ee556fafb4b",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1cccc(C2C(=C([O-])c3ccncc3)C(=O)C(=O)N2Cc2ccc(F)cc2)c1 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cccc(C2C(=C([O-])c3ccncc3)C(=O)C(=O)N2Cc2ccc(F)cc2)c1",
"ref_smiles": "Cc1cccc(C2C(=C([O-])c3ccncc3)C(=O)C(=O)N2Cc2ccc(C(=O)[OH])cc2)c1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "c4047406-cfce-454d-95ce-3fa7ce1825b9",
"task": "add",
"question": "Please add a benzene ring to the molecule CCOC(C)(CC)c1[nH+]c(O)cn1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(C)(CC)c1[nH+]c(O)cn1C.",
"ref_smiles": "CCOC(C)(c1[nH+]c(O)cn1C)C(C)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "0d38dae5-5b2f-41d5-ac39-7456dc3ec1e3",
"task": "add",
"question": "Modify the molecule CCOCCCCCc1ccc(C2CCC([NH3+])(COP(=O)([O-])[O-])C2)cc1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOCCCCCc1ccc(C2CCC([NH3+])(COP(=O)([O-])[O-])C2)cc1",
"ref_smiles": "CCOCCCCCc1ccc(C2CCC([NH3+])(COP(=O)([O-])[O-])C2)c(O)c1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "cce400af-726e-4f3f-bbd1-cbd8f5af528d",
"task": "add",
"question": "Modify the molecule CC1CN(C(=O)CCc2ccsc2)CC(C(=O)[O-])O1 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1CN(C(=O)CCc2ccsc2)CC(C(=O)[O-])O1",
"ref_smiles": "NCC1CN(C(=O)CCc2ccsc2)CC(C(=O)[O-])O1",
"add_group": "amine",
"remove_group": null
},
{
"id": "3fd91bb6-a431-4387-a71e-47f7cc792517",
"task": "sub",
"question": "Modify the molecule OCc1ccccc1-c1coc(CSc2ncnc3sccc23)c1 by substituting a hydroxyl with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "OCc1ccccc1-c1coc(CSc2ncnc3sccc23)c1",
"ref_smiles": "O=Cc1ccccc1-c1coc(CSc2ncnc3sccc23)c1",
"add_group": "aldehyde",
"remove_group": "hydroxyl"
},
{
"id": "1c228b59-7203-4bfa-a3d4-6e95e1e93a1b",
"task": "add",
"question": "Please add a benzene ring to the molecule O=C(Cc1ccc2ccccc2c1)Nc1nc2c(nc1-c1cccs1)-c1ccc(O)cc1CC2.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(Cc1ccc2ccccc2c1)Nc1nc2c(nc1-c1cccs1)-c1ccc(O)cc1CC2.",
"ref_smiles": "O=C(Cc1ccc2cc(-c3ccccc3)ccc2c1)Nc1nc2c(nc1-c1cccs1)-c1ccc(O)cc1CC2",
"add_group": "benzene",
"remove_group": null
},
{
"id": "cd04d7a0-2032-4d0c-ac60-6ed18c3238a9",
"task": "sub",
"question": "Modify the molecule CCCC[NH+](CP1OCC(Cl)(Cl)C(C)O1)CP1OCC(Cl)(Cl)C(C)O1 by substituting a halo with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCC[NH+](CP1OCC(Cl)(Cl)C(C)O1)CP1OCC(Cl)(Cl)C(C)O1",
"ref_smiles": "CCCC[NH+](CP1OCC(S)(Cl)C(C)O1)CP1OCC(Cl)(Cl)C(C)O1",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "c1e7cd02-064e-4010-b39b-4de35938f249",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule C=CC(N)[NH2+]CC(O)COc1ccccc1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CC(N)[NH2+]CC(O)COc1ccccc1",
"ref_smiles": "CC(=O)C(C[NH2+]C(N)C=C)COc1ccccc1",
"add_group": "aldehyde",
"remove_group": "hydroxyl"
},
{
"id": "4abb4946-6bc0-4fd3-b597-315d4f7a4cf1",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CC1(C)CN(C(=O)c2ccc3c(c2)CCC3)CC1O with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(C)CN(C(=O)c2ccc3c(c2)CCC3)CC1O",
"ref_smiles": "CC1(C)CN(C(=O)c2ccc3c(c2)CCC3)CC1C(=O)O",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "2a61ba54-1da4-4624-8bae-3ac5acd3713f",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CSc1ccc(C=CC(=O)NCC2CCN(C(=O)Oc3ccccc3)CC2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CSc1ccc(C=CC(=O)NCC2CCN(C(=O)Oc3ccccc3)CC2)cc1.",
"ref_smiles": "CSC=CC(=O)NCC1CCN(C(=O)Oc2ccccc2)CC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "01316cd6-e426-43e2-a62f-00d67a3965e0",
"task": "add",
"question": "Please add a amine to the molecule Nc1noc(-c2ccc(I)cc2)c1-c1cc(F)cc(F)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Nc1noc(-c2ccc(I)cc2)c1-c1cc(F)cc(F)c1.",
"ref_smiles": "Nc1cc(-c2onc(N)c2-c2cc(F)cc(F)c2)ccc1I",
"add_group": "amine",
"remove_group": null
},
{
"id": "c1222128-7830-46d0-9b27-735a84a6969c",
"task": "delete",
"question": "Modify the molecule C=CCNC(NCCc1ccco1)=[NH+]CCC by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CCNC(NCCc1ccco1)=[NH+]CCC",
"ref_smiles": "C=CCC(NCCc1ccco1)=[NH+]CCC",
"add_group": null,
"remove_group": "amine"
},
{
"id": "32d54dd0-6600-405e-a79a-334e5a6f34d7",
"task": "add",
"question": "Please add a aldehyde to the molecule O=C([O-])c1cc(Cl)cc(NS(=O)(=O)N2CCCC2)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C([O-])c1cc(Cl)cc(NS(=O)(=O)N2CCCC2)c1.",
"ref_smiles": "O=CCc1c(Cl)cc(NS(=O)(=O)N2CCCC2)cc1C(=O)[O-]",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "18cf0c53-832d-4880-bcd5-60689c122c56",
"task": "add",
"question": "Modify the molecule CCC(=O)N(c1ccc(C(=O)OC)cn1)C1CCCC1c1ccc(N)cc1 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(=O)N(c1ccc(C(=O)OC)cn1)C1CCCC1c1ccc(N)cc1",
"ref_smiles": "CCC(=O)N(c1ccc(C(=O)OC)cn1)C1CCC(N)C1c1ccc(N)cc1",
"add_group": "amine",
"remove_group": null
},
{
"id": "df9b11b3-d36d-4a32-b7dd-e592f6206598",
"task": "delete",
"question": "Please remove a halo from the molecule Fc1cccc(Cl)c1CN(CCCl)CC(F)F.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Fc1cccc(Cl)c1CN(CCCl)CC(F)F.",
"ref_smiles": "CCN(Cc1c(F)cccc1Cl)CC(F)F",
"add_group": null,
"remove_group": "halo"
},
{
"id": "3a7fbdfb-5c6b-4ce5-844d-00bcbc8c9cda",
"task": "sub",
"question": "Please substitute a halo in the molecule CCC([NH3+])C(Sc1nnc(SC)s1)c1ccc(Cl)cc1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC([NH3+])C(Sc1nnc(SC)s1)c1ccc(Cl)cc1",
"ref_smiles": "CC(=O)c1ccc(C(Sc2nnc(SC)s2)C([NH3+])CC)cc1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "e5467d99-474c-4a69-9f35-612833151c89",
"task": "add",
"question": "Please add a benzene ring to the molecule COC(C(=O)OC(C1CC=CC(=O)O1)C(c1ccccc1)c1cc([O-])c2c(c1)OC(c1ccccc1)CC2=O)(c1ccccc1)C(F)(F)F.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(C(=O)OC(C1CC=CC(=O)O1)C(c1ccccc1)c1cc([O-])c2c(c1)OC(c1ccccc1)CC2=O)(c1ccccc1)C(F)(F)F.",
"ref_smiles": "COC(C(=O)OC(c1ccccc1)(C1CC=CC(=O)O1)C(c1ccccc1)c1cc([O-])c2c(c1)OC(c1ccccc1)CC2=O)(c1ccccc1)C(F)(F)F",
"add_group": "benzene",
"remove_group": null
},
{
"id": "e79963ae-98b3-487f-bd72-00d2786a2cac",
"task": "add",
"question": "Please add a nitrile to the molecule C=CC([NH3+])c1c(-c2ccccc2)[nH]c2ccccc12.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CC([NH3+])c1c(-c2ccccc2)[nH]c2ccccc12.",
"ref_smiles": "C=CC([NH3+])c1c(-c2ccc(C#N)cc2)[nH]c2ccccc12",
"add_group": "nitrile",
"remove_group": null
},
{
"id": "03d7639e-1594-4baa-8c9c-b35eddfdc9b3",
"task": "delete",
"question": "Modify the molecule C=CCOC(=O)C(=[N+]=[N-])C(=O)C(C)C1NC(=O)C1C(C)O by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CCOC(=O)C(=[N+]=[N-])C(=O)C(C)C1NC(=O)C1C(C)O",
"ref_smiles": "C=CCOC(=O)C(=[N+]=[N-])C(=O)C(C)C1NC(=O)C1CC",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "add5090a-85ea-4812-829f-27af56a734e3",
"task": "sub",
"question": "Modify the molecule CC(C)c1c(Cl)ccc(C(=O)[O-])c1S(=O)(=O)N=C=O by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)c1c(Cl)ccc(C(=O)[O-])c1S(=O)(=O)N=C=O",
"ref_smiles": "CC(C)c1c(O)ccc(C(=O)[O-])c1S(=O)(=O)N=C=O",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "4cc763e2-67a1-4fe0-8c73-3a52f2bc9189",
"task": "sub",
"question": "Modify the molecule CC(C)(C)CC([NH3+])C(=O)NC1(C#N)CC[NH+](C2CCCCC2c2ccccc2)CC1 by substituting a nitrile with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)CC([NH3+])C(=O)NC1(C#N)CC[NH+](C2CCCCC2c2ccccc2)CC1",
"ref_smiles": "CC(=O)C1(NC(=O)C([NH3+])CC(C)(C)C)CC[NH+](C2CCCCC2c2ccccc2)CC1",
"add_group": "aldehyde",
"remove_group": "nitrile"
},
{
"id": "dbda8333-b1e6-45aa-a611-78ce8aa685f2",
"task": "delete",
"question": "Please remove a nitro from the molecule Cc1cc(Oc2c(C(=O)[O-])cccc2[N+](=O)[O-])ccc1Br.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(Oc2c(C(=O)[O-])cccc2[N+](=O)[O-])ccc1Br.",
"ref_smiles": "Cc1cc(Oc2c(C(=O)[O-])cccc2)ccc1Br",
"add_group": null,
"remove_group": "nitro"
},
{
"id": "97120a6d-96b3-4604-af92-903d7a96aa4c",
"task": "delete",
"question": "Modify the molecule CCOC(=O)c1nc(-c2cccc(C)c2Cl)oc1N by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(=O)c1nc(-c2cccc(C)c2Cl)oc1N",
"ref_smiles": "CCOC(=O)c1coc(-c2cccc(C)c2Cl)n1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "f63455d8-103b-4ebf-8ac6-be74996ca88d",
"task": "delete",
"question": "Please remove a halo from the molecule Cc1nc(-c2ccncc2)c(-c2ccccc2Cl)[nH]1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nc(-c2ccncc2)c(-c2ccccc2Cl)[nH]1.",
"ref_smiles": "Cc1nc(-c2ccncc2)c(-c2ccccc2)[nH]1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "464fd6a2-98ce-4354-a82a-45f524bbaca6",
"task": "delete",
"question": "Please remove a benzene ring from the molecule C[NH2+]Cc1ccc(OCCOc2ccccc2C(C)(C)C)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH2+]Cc1ccc(OCCOc2ccccc2C(C)(C)C)cc1.",
"ref_smiles": "C[NH2+]COCCOc1ccccc1C(C)(C)C",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "42bc347b-40be-43f4-ba3d-06c7611851b0",
"task": "delete",
"question": "Please remove a hydroxyl from the molecule CC(O)(CO)c1ccc(Cl)c(Cl)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(O)(CO)c1ccc(Cl)c(Cl)c1.",
"ref_smiles": "CC(CO)c1ccc(Cl)c(Cl)c1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "17bff0f9-4e6e-4a50-8f82-07f3b25351d5",
"task": "delete",
"question": "Please remove a benzene ring from the molecule Cc1cc(CNc2cc(-c3ccccc3C)nn2C)no1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(CNc2cc(-c3ccccc3C)nn2C)no1.",
"ref_smiles": "Cc1cc(NCc2cc(C)on2)n(C)n1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "e2a6521c-e925-47c9-9dee-909dd33d66f2",
"task": "sub",
"question": "Please substitute a halo in the molecule COc1ccccc1C(=O)NC(=Cc1ccc([N+](=O)[O-])cc1)C(=O)Nc1ccc(F)c(Cl)c1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccccc1C(=O)NC(=Cc1ccc([N+](=O)[O-])cc1)C(=O)Nc1ccc(F)c(Cl)c1",
"ref_smiles": "COc1ccccc1C(=O)NC(=Cc1ccc([N+](=O)[O-])cc1)C(=O)Nc1ccc(C=O)cc1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "d75ce0e1-1399-49dd-bda3-c418be3c4958",
"task": "add",
"question": "Please add a benzene ring to the molecule CCn1cc(C2CCN(C(=O)Nc3ccccc3N(C)C3CCCC3)CC2)cn1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCn1cc(C2CCN(C(=O)Nc3ccccc3N(C)C3CCCC3)CC2)cn1.",
"ref_smiles": "CCn1cc(C2CCN(C(=O)Nc3c(-c4ccccc4)cccc3N(C)C3CCCC3)CC2)cn1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "1d408cfc-1678-4eeb-9ce1-f72e846ce489",
"task": "add",
"question": "Modify the molecule C=CCn1c(=O)c(C(=O)OCCCC)c([O-])c2cc(OC)c(OC)cc21 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CCn1c(=O)c(C(=O)OCCCC)c([O-])c2cc(OC)c(OC)cc21",
"ref_smiles": "C=CCn1c(=O)c(C(=O)OC(N)CCC)c([O-])c2cc(OC)c(OC)cc21",
"add_group": "amine",
"remove_group": null
},
{
"id": "52942b8e-62a0-4c92-9bbc-912fce6fb3fa",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CCCCCCCOc1c(C(=O)N=Nc2c(O)[nH]c3ccccc23)sc(C(=O)N=Nc2c(O)[nH]c3ccccc23)c1OCCCCCCC with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCCCOc1c(C(=O)N=Nc2c(O)[nH]c3ccccc23)sc(C(=O)N=Nc2c(O)[nH]c3ccccc23)c1OCCCCCCC",
"ref_smiles": "CCCCCCCOc1c(C(=O)N=Nc2c(O)[nH]c3ccccc23)sc(C(=O)N=Nc2c(S)[nH]c3ccccc23)c1OCCCCCCC",
"add_group": "thiol",
"remove_group": "hydroxyl"
},
{
"id": "210a7b86-3fe9-4f1a-890b-9dd2b75578df",
"task": "add",
"question": "Please add a carboxyl to the molecule O=C1CCCCC1C1CCCCCN1C(=O)c1ccc(-n2cncn2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C1CCCCC1C1CCCCCN1C(=O)c1ccc(-n2cncn2)cc1.",
"ref_smiles": "O=C1CCCCC1C1CCCCC(C(=O)O)N1C(=O)c1ccc(-n2cncn2)cc1",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "71bed53c-04bb-4537-b5ac-1728fdc7a015",
"task": "add",
"question": "Modify the molecule CN(CC1CCCCC1)c1nc(N)nc2ccccc12 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(CC1CCCCC1)c1nc(N)nc2ccccc12",
"ref_smiles": "CN(CC1CCCCC1)c1nc(N)nc2c(C(=O)O)cccc12",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "3ba8c1e9-b45d-48c4-9ccc-098f05ce8b29",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CCCCc1[nH+]cc(C=C(Cc2ccc(C)s2)c2nn[n-]n2)n1Cc1ccccc1Cl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCc1[nH+]cc(C=C(Cc2ccc(C)s2)c2nn[n-]n2)n1Cc1ccccc1Cl.",
"ref_smiles": "CCCCc1[nH+]cc(C=C(Cc2ccc(C)s2)c2nn[n-]n2)n1CCl",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "e1081218-46ca-4c27-8401-85f211be2192",
"task": "add",
"question": "Please add a hydroxyl to the molecule CC(C)Nc1cc[nH+]c(C(=O)Nc2c(Cl)cccc2Cl)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)Nc1cc[nH+]c(C(=O)Nc2c(Cl)cccc2Cl)c1.",
"ref_smiles": "CC(CO)Nc1cc[nH+]c(C(=O)Nc2c(Cl)cccc2Cl)c1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "3ca3483b-6d26-460b-84a2-8cf1cb230b45",
"task": "delete",
"question": "Modify the molecule O=C([O-])c1cncnc1C[NH2+]CCCCCO by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C([O-])c1cncnc1C[NH2+]CCCCCO",
"ref_smiles": "CCCCC[NH2+]Cc1ncncc1C(=O)[O-]",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "659a8a4c-d983-4505-b9b8-6b2f7c718b74",
"task": "sub",
"question": "Modify the molecule Cc1ccc(F)c(C(CC2CCOCC2)NN)c1 by substituting a halo with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(F)c(C(CC2CCOCC2)NN)c1",
"ref_smiles": "Cc1ccc(C(=O)[OH])c(C(CC2CCOCC2)NN)c1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "7af67ad2-d8c8-4d37-b70d-8fe418975dd8",
"task": "add",
"question": "Modify the molecule C=[P+](CC)CC([P+](=C)CC)[P+](=C)C(O)C12CC1C(C)C(C)(O)C2C by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=[P+](CC)CC([P+](=C)CC)[P+](=C)C(O)C12CC1C(C)C(C)(O)C2C",
"ref_smiles": "C=[P+](CC([P+](=C)CC)[P+](=C)C(O)C12CC1C(C)C(C)(O)C2C)C(C)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "789a4171-bda3-4afb-9cad-86c3f07c6d61",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CCNC(NC1CCCC(C)C1)=[NH+]CC(O)Cc1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCNC(NC1CCCC(C)C1)=[NH+]CC(O)Cc1ccccc1.",
"ref_smiles": "CCNC(NC1CCCC(C)C1)=[NH+]CC(C)O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "8d3c25d5-e07f-4f89-8a27-4238621f3110",
"task": "sub",
"question": "Modify the molecule Clc1ccccc1C1=NCCNc2ccccc21 by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Clc1ccccc1C1=NCCNc2ccccc21",
"ref_smiles": "Oc1ccccc1C1=NCCNc2ccccc21",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "f5e5db6d-492c-49f7-b61e-9d27f3102fdb",
"task": "delete",
"question": "Modify the molecule C#CCSCC[NH2+]C(C)C(=O)NC(CC)CC by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C#CCSCC[NH2+]C(C)C(=O)NC(CC)CC",
"ref_smiles": "C#CCSCC[NH2+]C(C)(CC)CC",
"add_group": null,
"remove_group": "amide"
},
{
"id": "166dfdbe-3404-4955-9b70-6ca84f4bc706",
"task": "add",
"question": "Modify the molecule c1cc(-c2ccc3c(c2)C[NH2+]CC3)c2cc[nH]c2n1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "c1cc(-c2ccc3c(c2)C[NH2+]CC3)c2cc[nH]c2n1",
"ref_smiles": "Oc1c(-c2ccnc3[nH]ccc23)ccc2c1C[NH2+]CC2",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "23a73f3b-5bf6-490f-a4d0-45c4e06431ac",
"task": "delete",
"question": "Modify the molecule O=C([O-])CN1CC(=O)N(c2ccc(Cl)cc2)C1=O by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C([O-])CN1CC(=O)N(c2ccc(Cl)cc2)C1=O",
"ref_smiles": "O=C([O-])CN1CC(=O)N(Cl)C1=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "f6311a3e-28c2-46c6-b208-70dac6d7658c",
"task": "add",
"question": "Modify the molecule COCCC1(c2ccc(Nc3nc(-c4c(F)cccc4F)[nH]c4c[nH]c(=O)c3-4)cc2)CCN(C)C1=O by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCCC1(c2ccc(Nc3nc(-c4c(F)cccc4F)[nH]c4c[nH]c(=O)c3-4)cc2)CCN(C)C1=O",
"ref_smiles": "COCCC1(c2ccc(Nc3nc(-c4c(F)cccc4F)[nH]c4c(C(=O)O)[nH]c(=O)c3-4)cc2)CCN(C)C1=O",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "1f68b91a-73ba-45ad-a672-7d3498400ba6",
"task": "sub",
"question": "Please substitute a halo in the molecule CNC(=O)C(Cc1ccccc1)N(Cc1cccc(Br)c1)C(=O)CN(c1ccccc1OC)S(C)(=O)=O with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CNC(=O)C(Cc1ccccc1)N(Cc1cccc(Br)c1)C(=O)CN(c1ccccc1OC)S(C)(=O)=O",
"ref_smiles": "CNC(=O)C(Cc1ccccc1)N(Cc1cccc(C(=O)[OH])c1)C(=O)CN(c1ccccc1OC)S(C)(=O)=O",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "fa39af57-c0c8-423d-8529-813fa9ecc596",
"task": "sub",
"question": "Modify the molecule COc1cc(Br)c(CNc2cnc(Cl)c(C)c2)cc1OC by substituting a halo with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cc(Br)c(CNc2cnc(Cl)c(C)c2)cc1OC",
"ref_smiles": "COc1cc(C#N)c(CNc2cnc(Cl)c(C)c2)cc1OC",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "8617eb83-9dac-4a01-9128-c0445adf5ba8",
"task": "delete",
"question": "Modify the molecule COCCn1cc(C)sc1=NC(=O)C12CC3CC(CC(O)(C3)C1)C2 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCCn1cc(C)sc1=NC(=O)C12CC3CC(CC(O)(C3)C1)C2",
"ref_smiles": "COCCn1cc(C)sc1=NC(=O)C12CC3CC(CC(C3)C1)C2",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "0e62632c-6cfd-41ef-a682-2a42e2eefa4a",
"task": "add",
"question": "Modify the molecule CCCCCCN(C(=O)C(CS)NC(=O)OC(C)(C)C)C(C(=O)NC(C)C)c1ccc(CC)cc1 by adding a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCCN(C(=O)C(CS)NC(=O)OC(C)(C)C)C(C(=O)NC(C)C)c1ccc(CC)cc1",
"ref_smiles": "CCCCCCN(C(=O)C(CS)NC(=O)OC(C)(C)C)C(C(=O)NC(C)C)c1ccc(CCS)cc1",
"add_group": "thiol",
"remove_group": null
},
{
"id": "fccf9b83-19a9-4555-aab8-5d3c8072509c",
"task": "add",
"question": "Modify the molecule CC(C(=O)[O-])C(=O)N1CCCC1C1CCCC1 by adding a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C(=O)[O-])C(=O)N1CCCC1C1CCCC1",
"ref_smiles": "CC(C(=O)[O-])C(=O)N1CCCC1C1CCC(CC=O)C1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "ea4da524-1f5b-4de8-bae0-e2261468ae27",
"task": "sub",
"question": "Modify the molecule COCCC[NH2+]Cc1cccc(Cl)c1 by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCCC[NH2+]Cc1cccc(Cl)c1",
"ref_smiles": "COCCC[NH2+]Cc1cccc(O)c1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "9af76d1e-e760-4e94-8e24-9b469d78c131",
"task": "add",
"question": "Modify the molecule Cc1c(SCCCSc2n[nH]c(N)n2)ccnc1CSc1nc2ccccc2[nH]1 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(SCCCSc2n[nH]c(N)n2)ccnc1CSc1nc2ccccc2[nH]1",
"ref_smiles": "Cc1c(SCC(CSc2n[nH]c(N)n2)C(=O)O)ccnc1CSc1nc2ccccc2[nH]1",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "846c5051-4620-4895-9112-5aa04b80ef3f",
"task": "add",
"question": "Modify the molecule CCC(C#N)S(=O)(=O)NCC(O)C(F)(F)F by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(C#N)S(=O)(=O)NCC(O)C(F)(F)F",
"ref_smiles": "CCC(C#N)S(=O)(=O)NC(C(=O)O)C(O)C(F)(F)F",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "df1aa995-9903-46de-8615-6eef4b5b10fe",
"task": "delete",
"question": "Please remove a nitrile from the molecule Cc1cccc(C)c1NC1=[NH+]C(=O)C(=Cc2ccccc2OCC#N)S1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cccc(C)c1NC1=[NH+]C(=O)C(=Cc2ccccc2OCC#N)S1.",
"ref_smiles": "COc1ccccc1C=C1SC(Nc2c(C)cccc2C)=[NH+]C1=O",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "5f8a00fe-0852-45cf-a461-0ac009204819",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1cc(C(=O)NCC(C)C)ccc1NC(=O)C[NH+]1CCC(C(=O)NCC(=O)Nc2cccc(C(=O)Nc3ccc(F)cc3)c2)CC1 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C(=O)NCC(C)C)ccc1NC(=O)C[NH+]1CCC(C(=O)NCC(=O)Nc2cccc(C(=O)Nc3ccc(F)cc3)c2)CC1",
"ref_smiles": "Cc1cc(C(=O)NCC(C)C)ccc1NC(=O)C[NH+]1CCC(C(=O)NCC(=O)Nc2cccc(C(=O)Nc3ccc(C#N)cc3)c2)CC1",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "744328b6-3bce-4998-801a-ac0e2ef8cc3a",
"task": "delete",
"question": "Please remove a halo from the molecule O=C(Nc1cccc(I)c1)c1ccc2c(=O)n3c(nc2c1)CCCCC3.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(Nc1cccc(I)c1)c1ccc2c(=O)n3c(nc2c1)CCCCC3.",
"ref_smiles": "O=C(Nc1ccccc1)c1ccc2c(=O)n3c(nc2c1)CCCCC3",
"add_group": null,
"remove_group": "halo"
},
{
"id": "20a4b1c7-81f5-4700-a860-2543bf3ea88d",
"task": "add",
"question": "Please add a hydroxyl to the molecule O=C(C=Cc1cccc(Cl)c1Cl)c1ccc(Nc2nc(Nc3ccc(F)cc3)nc(Nc3ccc(F)cc3)n2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(C=Cc1cccc(Cl)c1Cl)c1ccc(Nc2nc(Nc3ccc(F)cc3)nc(Nc3ccc(F)cc3)n2)cc1.",
"ref_smiles": "O=C(C=Cc1cc(O)cc(Cl)c1Cl)c1ccc(Nc2nc(Nc3ccc(F)cc3)nc(Nc3ccc(F)cc3)n2)cc1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "6d3e448f-1377-4357-ae52-3e8f2c0523ad",
"task": "sub",
"question": "Modify the molecule Cc1c(CO)sc2ncnn12 by substituting a hydroxyl with a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(CO)sc2ncnn12",
"ref_smiles": "Cc1c(CF)sc2ncnn12",
"add_group": "halo",
"remove_group": "hydroxyl"
},
{
"id": "4f010653-7d7f-4a20-b746-c795bd79d6bd",
"task": "delete",
"question": "Please remove a benzene ring from the molecule COc1ccc([N+](=O)[O-])cc1NC(=O)NCC[NH+](C)C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc([N+](=O)[O-])cc1NC(=O)NCC[NH+](C)C.",
"ref_smiles": "CON(C(=O)NCC[NH+](C)C)[N+](=O)[O-]",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "7d84a4db-e4c6-4b14-b89e-481ad4af83c4",
"task": "delete",
"question": "Modify the molecule CC([NH2+]CC(=O)Nc1ccc2c(c1)OCO2)c1ccc(S(N)(=O)=O)cc1 by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC([NH2+]CC(=O)Nc1ccc2c(c1)OCO2)c1ccc(S(N)(=O)=O)cc1",
"ref_smiles": "CC([NH2+]c1ccc2c(c1)OCO2)c1ccc(S(N)(=O)=O)cc1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "2b20a800-6e71-4100-b7c1-2bbb531bbeda",
"task": "delete",
"question": "Modify the molecule CCC1CCC(O)(CNC(=O)C2CNC(=O)C[NH2+]2)CC1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC1CCC(O)(CNC(=O)C2CNC(=O)C[NH2+]2)CC1",
"ref_smiles": "CCC1CCC(CNC(=O)C2CNC(=O)C[NH2+]2)CC1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "dc8de655-a350-485c-91d5-f94ec399e956",
"task": "delete",
"question": "Modify the molecule COc1cccc2oc(-c3nc4ccccc4c(=O)n3N=Cc3cc(Cl)ccc3O)cc12 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cccc2oc(-c3nc4ccccc4c(=O)n3N=Cc3cc(Cl)ccc3O)cc12",
"ref_smiles": "COc1cccc2oc(-c3nc4ccccc4c(=O)n3N=COCl)cc12",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "5baf7d9b-4bb8-47a5-8f7c-d3363e25a26f",
"task": "delete",
"question": "Please remove a nitrile from the molecule N#CC(N1CCCC(c2ccnc3[nH]nc4nccc-4c23)C1)S(=O)[O-].\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "N#CC(N1CCCC(c2ccnc3[nH]nc4nccc-4c23)C1)S(=O)[O-].",
"ref_smiles": "O=S([O-])CN1CCCC(c2ccnc3[nH]nc4nccc-4c23)C1",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "d3996550-f689-42f2-b46a-8b376b85b86b",
"task": "delete",
"question": "Please remove a nitrile from the molecule Cc1ccccc1COc1nn(Cc2ccccc2C)c(N)c1C#N.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccccc1COc1nn(Cc2ccccc2C)c(N)c1C#N.",
"ref_smiles": "Cc1ccccc1COc1cc(N)n(Cc2ccccc2C)n1",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "ca0be832-0e15-47c1-adcf-0911ed1ced7c",
"task": "sub",
"question": "Please substitute a halo in the molecule CN(Cc1nc(-c2ccc(Cl)cc2)no1)C(=O)C(c1ccccc1)N(C)S(C)(=O)=O with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(Cc1nc(-c2ccc(Cl)cc2)no1)C(=O)C(c1ccccc1)N(C)S(C)(=O)=O",
"ref_smiles": "CN(Cc1nc(-c2ccc(C(=O)[OH])cc2)no1)C(=O)C(c1ccccc1)N(C)S(C)(=O)=O",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "403dc799-2731-405d-9751-5c6b4db2afcb",
"task": "add",
"question": "Modify the molecule CC(=O)NC1C(CCO)OC(COCc2ccccc2)C(OCc2ccccc2)C1OCc1ccccc1 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)NC1C(CCO)OC(COCc2ccccc2)C(OCc2ccccc2)C1OCc1ccccc1",
"ref_smiles": "CC(=O)NC1C(CCO)OC(COCc2ccccc2)C(OCc2ccccc2N)C1OCc1ccccc1",
"add_group": "amine",
"remove_group": null
},
{
"id": "0550d210-a4f6-4582-b331-e74228557968",
"task": "add",
"question": "Modify the molecule CN(c1ccccc1-c1ccc2c(c1)Nc1cc(C(=O)NCCCN3CCCC3=O)ccc1NC2=O)S(C)(=O)=O by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(c1ccccc1-c1ccc2c(c1)Nc1cc(C(=O)NCCCN3CCCC3=O)ccc1NC2=O)S(C)(=O)=O",
"ref_smiles": "CN(c1ccccc1-c1ccc2c(c1)Nc1cc(C(=O)NCCC(c3ccccc3)N3CCCC3=O)ccc1NC2=O)S(C)(=O)=O",
"add_group": "benzene",
"remove_group": null
},
{
"id": "cb50fa5c-0953-4598-8bed-c7c48d7c8cfc",
"task": "delete",
"question": "Modify the molecule CCCC1=CC(=O)OC2C1=CC(C)(C)C1=C2C(C(=O)C(C)C(O)CC)C(=O)CO1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCC1=CC(=O)OC2C1=CC(C)(C)C1=C2C(C(=O)C(C)C(O)CC)C(=O)CO1",
"ref_smiles": "CCCC1=CC(=O)OC2C1=CC(C)(C)C1=C2C(C(=O)C(C)CCC)C(=O)CO1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "4fddf8f3-0256-4945-bc2b-e28209d41c32",
"task": "add",
"question": "Modify the molecule Cc1ccc2noc(CCC(=O)[O-])c2c1 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc2noc(CCC(=O)[O-])c2c1",
"ref_smiles": "Cc1cc(N)c2noc(CCC(=O)[O-])c2c1",
"add_group": "amine",
"remove_group": null
},
{
"id": "5723baa8-5c91-4b50-b810-8a7e831eb529",
"task": "sub",
"question": "Modify the molecule C=C(C)c1c(C)c(F)c2ccc(Br)cc2c1OC(=O)OC(C)(C)C by substituting a halo with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=C(C)c1c(C)c(F)c2ccc(Br)cc2c1OC(=O)OC(C)(C)C",
"ref_smiles": "C=C(C)c1c(C)c(C#N)c2ccc(Br)cc2c1OC(=O)OC(C)(C)C",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "df2602b8-f4bd-44c8-8792-a6d8ca25d012",
"task": "delete",
"question": "Please remove a halo from the molecule Cc1cccc(C)c1NS(=O)(=O)c1ccc(NC(=O)Cc2ccc(Cl)nc2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cccc(C)c1NS(=O)(=O)c1ccc(NC(=O)Cc2ccc(Cl)nc2)cc1.",
"ref_smiles": "Cc1cccc(C)c1NS(=O)(=O)c1ccc(NC(=O)Cc2cccnc2)cc1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "de4edfcf-d816-46cc-a97f-51eb897b421d",
"task": "add",
"question": "Please add a hydroxyl to the molecule COc1ccccc1C=CCN(CC[NH+]1CCN(C(=O)c2ccc(F)cc2)CC1)C(=O)CC(C)(C)C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccccc1C=CCN(CC[NH+]1CCN(C(=O)c2ccc(F)cc2)CC1)C(=O)CC(C)(C)C.",
"ref_smiles": "CC(C)(C)CC(=O)N(CC=Cc1ccccc1O)CC[NH+]1CCN(C(=O)c2ccc(F)cc2)CC1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "f4b068f7-0c5c-4eb2-8fdb-e0e688f6e586",
"task": "add",
"question": "Please add a benzene ring to the molecule CC(CNC=S)c1ccc(C(C)CNC=S)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(CNC=S)c1ccc(C(C)CNC=S)cc1.",
"ref_smiles": "CC(CNC=S)c1ccc(C(C)C(NC=S)c2ccccc2)cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "20812e45-58ff-40b3-8989-79d101854a5a",
"task": "delete",
"question": "Modify the molecule N#Cc1ccc2nnc(C3CCC(F)(F)C3)n2c1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "N#Cc1ccc2nnc(C3CCC(F)(F)C3)n2c1",
"ref_smiles": "N#Cc1ccc2nnc(C3CCC(F)C3)n2c1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "b4fbac32-e31d-4def-90dd-ed319a6b423b",
"task": "add",
"question": "Please add a benzene ring to the molecule CC[NH+]=C(NC1C2CCOC2C12CCCC2)N1CCC2(CCC2)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC[NH+]=C(NC1C2CCOC2C12CCCC2)N1CCC2(CCC2)C1.",
"ref_smiles": "CC[NH+]=C(NC1C2CCOC2C12CCC(c1ccccc1)C2)N1CCC2(CCC2)C1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "2833b051-0873-412a-bf52-0f35722f8973",
"task": "sub",
"question": "Please substitute a halo in the molecule [NH3+]CC(=O)NCC#Cc1cccc(Cl)c1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "[NH3+]CC(=O)NCC#Cc1cccc(Cl)c1",
"ref_smiles": "CC(=O)c1cccc(C#CCNC(=O)C[NH3+])c1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "f04dc3ee-98b6-49d2-8927-356f8ec67aa2",
"task": "add",
"question": "Please add a amine to the molecule CC(C)(C)[NH2+]Cc1ccsc1Cl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)[NH2+]Cc1ccsc1Cl.",
"ref_smiles": "CC(C)(CN)[NH2+]Cc1ccsc1Cl",
"add_group": "amine",
"remove_group": null
},
{
"id": "afceadcf-5543-4fff-91c4-c3159632d3c3",
"task": "add",
"question": "Please add a carboxyl to the molecule CCCn1nc(C(=O)Nc2ncc[nH]2)ccc1=O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCn1nc(C(=O)Nc2ncc[nH]2)ccc1=O.",
"ref_smiles": "CCCn1nc(C(=O)Nc2nc(C(=O)O)c[nH]2)ccc1=O",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "ee7fbcc4-8c86-4554-b720-100245fb457f",
"task": "sub",
"question": "Please substitute a halo in the molecule CCCN(c1ccc(CC[NH3+])c(C(F)(F)F)c1)C1CC1 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCN(c1ccc(CC[NH3+])c(C(F)(F)F)c1)C1CC1",
"ref_smiles": "CCCN(c1ccc(CC[NH3+])c(C(F)(F)C(=O)O)c1)C1CC1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "d73c0836-efcc-4933-90a3-701e2a2a1532",
"task": "sub",
"question": "Modify the molecule CC(C)(C)c1nnsc1C(O)Cc1cncs1 by substituting a hydroxyl with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)c1nnsc1C(O)Cc1cncs1",
"ref_smiles": "CC(C)(C)c1nnsc1C(C#N)Cc1cncs1",
"add_group": "nitrile",
"remove_group": "hydroxyl"
},
{
"id": "555cb38e-b1fc-4ba2-a934-341308885bd0",
"task": "add",
"question": "Modify the molecule Cc1ccc(NC(=O)CN(c2ccccc2Cl)S(C)(=O)=O)cc1C by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(NC(=O)CN(c2ccccc2Cl)S(C)(=O)=O)cc1C",
"ref_smiles": "Cc1ccc(NC(=O)CN(c2ccccc2Cl)S(C)(=O)=O)cc1CO",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "b4e363b5-f0fa-49b7-b684-2243c1128836",
"task": "add",
"question": "Please add a hydroxyl to the molecule Cc1nn(C)c2cc(-c3noc(C4CCN(C(=O)CC5C[NH+](C(O)OC(C)(C)C)C5)CC4)n3)ccc12.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nn(C)c2cc(-c3noc(C4CCN(C(=O)CC5C[NH+](C(O)OC(C)(C)C)C5)CC4)n3)ccc12.",
"ref_smiles": "Cc1nn(C)c2cc(-c3noc(C4CCN(C(=O)CC5(O)C[NH+](C(O)OC(C)(C)C)C5)CC4)n3)ccc12",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "cb901d2f-b3c7-4065-9296-c56aa47d761c",
"task": "delete",
"question": "Modify the molecule Cc1ccc(S(=O)(=O)N2CC(c3ccccc3)C(CCOC(=O)C(C)(C)C)=C2c2ccccc2)cc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(S(=O)(=O)N2CC(c3ccccc3)C(CCOC(=O)C(C)(C)C)=C2c2ccccc2)cc1",
"ref_smiles": "Cc1ccc(S(=O)(=O)N2C=C(CCOC(=O)C(C)(C)C)C(c3ccccc3)C2)cc1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "4a52d345-5722-41ce-8d32-10c96cc03b62",
"task": "add",
"question": "Modify the molecule OC(C[NH2+]Cc1ccccc1)COc1ccc(C23CC4CC(CC(C4)C2)C3)cc1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "OC(C[NH2+]Cc1ccccc1)COc1ccc(C23CC4CC(CC(C4)C2)C3)cc1",
"ref_smiles": "OC(COc1ccc(C23CC4CC(CC(C4)C2)C3)cc1)C([NH2+]Cc1ccccc1)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "3ecfa6fd-52c7-44a6-8595-8ad031885900",
"task": "add",
"question": "Modify the molecule COc1ccc(CC(=O)N2CCN(c3ncnc4c3nnn4-c3ccc(F)cc3)CC2)cc1OC by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(CC(=O)N2CCN(c3ncnc4c3nnn4-c3ccc(F)cc3)CC2)cc1OC",
"ref_smiles": "COc1ccc(CC(=O)N2CCN(c3ncnc4c3nnn4-c3ccc(F)cc3)CC2)c(O)c1OC",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "ec8859ea-b266-413a-8bd1-b7b2a2bff5f4",
"task": "delete",
"question": "Modify the molecule Cc1cccc(NC(=O)CSCc2cc(=O)n3ccsc3n2)c1C by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cccc(NC(=O)CSCc2cc(=O)n3ccsc3n2)c1C",
"ref_smiles": "CN(C)C(=O)CSCc1cc(=O)n2ccsc2n1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "21f9f34e-54a6-48cb-accc-949b586f44a7",
"task": "delete",
"question": "Modify the molecule CCOC(=O)c1ccc(Oc2ccc(C(N)=O)nn2)cc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(=O)c1ccc(Oc2ccc(C(N)=O)nn2)cc1",
"ref_smiles": "CCOC(=O)Oc1ccc(C(N)=O)nn1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "51aed955-cf5d-4b7f-9adf-e81724b7f1c6",
"task": "delete",
"question": "Please remove a amide from the molecule Cc1nc(C=CC(=O)NCCc2ccc(OCc3ccccc3)cc2)cs1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nc(C=CC(=O)NCCc2ccc(OCc3ccccc3)cc2)cs1.",
"ref_smiles": "Cc1nc(CCCc2ccc(OCc3ccccc3)cc2)cs1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "1a809800-bc4c-4cfc-9f2a-46f7f837c7e0",
"task": "add",
"question": "Modify the molecule CC(C)(C)NC(=O)c1ccccc1NC(=O)c1ccc(NS(C)(=O)=O)cc1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)NC(=O)c1ccccc1NC(=O)c1ccc(NS(C)(=O)=O)cc1",
"ref_smiles": "CC(C)(C)NC(=O)c1cc(-c2ccccc2)ccc1NC(=O)c1ccc(NS(C)(=O)=O)cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "0e741ca4-10ab-494d-9e0a-500c0882bfbf",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(NCC(=O)N(Cc1c(F)cccc1Cl)C1CC1)c1cccc(F)c1 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCC(=O)N(Cc1c(F)cccc1Cl)C1CC1)c1cccc(F)c1",
"ref_smiles": "N#Cc1cccc(Cl)c1CN(C(=O)CNC(=O)c1cccc(F)c1)C1CC1",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "346b066a-3130-485b-9710-421f3aebdcd8",
"task": "sub",
"question": "Modify the molecule COC(=O)C(c1ccccc1)S(=O)Cc1ccc(Br)cc1F by substituting a halo with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)C(c1ccccc1)S(=O)Cc1ccc(Br)cc1F",
"ref_smiles": "COC(=O)C(c1ccccc1)S(=O)Cc1ccc(S)cc1F",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "8a50c828-f62e-42ec-9095-06a67f4c7d23",
"task": "delete",
"question": "Please remove a benzene ring from the molecule Cc1ccc2c(n1)oc1c(-c3ncccc3-c3cccc(C(C)C)c3)c(C)ccc12.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc2c(n1)oc1c(-c3ncccc3-c3cccc(C(C)C)c3)c(C)ccc12.",
"ref_smiles": "Cc1ccc2c(n1)oc1c(-c3ncccc3C(C)C)c(C)ccc12",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "e62d23f7-9fe8-40f9-88a9-66bd8077fb23",
"task": "sub",
"question": "Please substitute a halo in the molecule COC(=O)c1cc(Cl)c(OC)c(C)c1O with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)c1cc(Cl)c(OC)c(C)c1O",
"ref_smiles": "COC(=O)c1cc(S)c(OC)c(C)c1O",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "c2687a05-f2fa-4190-baca-f5aaccd58cc3",
"task": "delete",
"question": "Please remove a amine from the molecule C[NH+]=C(NCC(C)Cn1nc(C)cc1C)N1CC(C)(C)C1(C)C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH+]=C(NCC(C)Cn1nc(C)cc1C)N1CC(C)(C)C1(C)C.",
"ref_smiles": "C[NH+]=C(CC(C)Cn1nc(C)cc1C)N1CC(C)(C)C1(C)C",
"add_group": null,
"remove_group": "amine"
},
{
"id": "6536cf01-960d-402c-accd-1643e48fe2f9",
"task": "sub",
"question": "Please substitute a halo in the molecule CCc1ccc(NC(=O)c2sc(COc3ccc(Cl)c(C)c3)nc2C)cc1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1ccc(NC(=O)c2sc(COc3ccc(Cl)c(C)c3)nc2C)cc1",
"ref_smiles": "CCc1ccc(NC(=O)c2sc(COc3ccc(C=O)c3)nc2C)cc1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "144257b3-f819-4cfd-a072-9f6a9ee337a9",
"task": "add",
"question": "Please add a amine to the molecule C[N+](C)(C)CC(=O)N=NC=C1C=C(N([O-])[O-])C=CC1=O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[N+](C)(C)CC(=O)N=NC=C1C=C(N([O-])[O-])C=CC1=O.",
"ref_smiles": "C[N+](C)(C)CC(=O)N=NC=C1C=C(N([O-])[O-])C(N)=CC1=O",
"add_group": "amine",
"remove_group": null
},
{
"id": "36c15a6e-e447-4c12-8c8a-faf0f0dc0bf7",
"task": "sub",
"question": "Modify the molecule Cc1ccc(CNC(=O)COC(=O)c2csc(-c3cccc(Cl)c3)n2)cc1 by substituting a halo with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(CNC(=O)COC(=O)c2csc(-c3cccc(Cl)c3)n2)cc1",
"ref_smiles": "CC(=O)c1cccc(-c2nc(C(=O)OCC(=O)NCc3ccc(C)cc3)cs2)c1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "7d7c8873-a310-4708-8caf-97f08ff41167",
"task": "add",
"question": "Please add a hydroxyl to the molecule CC([NH2+]CC(C)(C)c1ccccc1)c1cc(F)ccc1O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC([NH2+]CC(C)(C)c1ccccc1)c1cc(F)ccc1O.",
"ref_smiles": "CC(C)(C[NH2+]C(CO)c1cc(F)ccc1O)c1ccccc1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "d1f296c1-9be6-475a-b9ae-936472dde6dc",
"task": "add",
"question": "Modify the molecule COC(=O)C1([NH2+]C(C)C)CCC(Sc2cc(C)nn2C)C1 by adding a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)C1([NH2+]C(C)C)CCC(Sc2cc(C)nn2C)C1",
"ref_smiles": "COC(=O)C1([NH2+]C(C)CC#N)CCC(Sc2cc(C)nn2C)C1",
"add_group": "nitrile",
"remove_group": null
},
{
"id": "b5d97183-a292-4870-993f-05266a1d9e27",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1ccc(C(=O)Nc2ccc(F)cc2F)cc1NC(=O)C(C)[NH+]1CCC(C(=O)Nc2cccc(C(=O)NCC(C)C)c2C)CC1 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(C(=O)Nc2ccc(F)cc2F)cc1NC(=O)C(C)[NH+]1CCC(C(=O)Nc2cccc(C(=O)NCC(C)C)c2C)CC1",
"ref_smiles": "Cc1ccc(C(=O)Nc2ccc(C(=O)[OH])cc2F)cc1NC(=O)C(C)[NH+]1CCC(C(=O)Nc2cccc(C(=O)NCC(C)C)c2C)CC1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "bd890b40-3d5a-41ea-ab36-b103b26ca7a0",
"task": "delete",
"question": "Modify the molecule CCC(=O)CCc1cccc(-c2ccc(O)c3c2CC2CC4C([NH+](C)C)C(=O)C(C(N)=O)=C([O-])C4(O)C(=O)C2=C3[O-])c1 by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(=O)CCc1cccc(-c2ccc(O)c3c2CC2CC4C([NH+](C)C)C(=O)C(C(N)=O)=C([O-])C4(O)C(=O)C2=C3[O-])c1",
"ref_smiles": "CCC(=O)CCc1cccc(-c2ccc(O)c3c2CC2CC4C([NH+](C)C)C(=O)C([O-])C4(O)C(=O)C2=C3[O-])c1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "126df536-1e4a-404b-be21-cd214f0fadee",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule Cc1cc(Br)ccc1C[NH2+]CCO with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(Br)ccc1C[NH2+]CCO",
"ref_smiles": "Cc1cc(Br)ccc1C[NH2+]CCC(=O)[OH]",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "f1601a64-a004-4794-9d09-095fad02fffb",
"task": "sub",
"question": "Please substitute a thiol in the molecule CC(C)CC(NC(=O)C([NH3+])CC(=O)[O-])C(=O)N1CCCC1C(=O)NCC(=O)NC(CS)C(=O)[O-] with a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)CC(NC(=O)C([NH3+])CC(=O)[O-])C(=O)N1CCCC1C(=O)NCC(=O)NC(CS)C(=O)[O-]",
"ref_smiles": "CC(C)CC(NC(=O)C([NH3+])CC(=O)[O-])C(=O)N1CCCC1C(=O)NCC(=O)NC(CF)C(=O)[O-]",
"add_group": "halo",
"remove_group": "thiol"
},
{
"id": "9c56d350-60d4-4950-8fcd-a0a46212f03a",
"task": "sub",
"question": "Please substitute a halo in the molecule CCCC(C)C1CCC(C(=NN=Cc2ccc(F)c(F)c2)c2ccccc2)CC1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCC(C)C1CCC(C(=NN=Cc2ccc(F)c(F)c2)c2ccccc2)CC1",
"ref_smiles": "CCCC(C)C1CCC(C(=NN=Cc2ccc(C=O)cc2)c2ccccc2)CC1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "7dd7625a-854b-4e05-839f-ba1f55259ff1",
"task": "add",
"question": "Please add a benzene ring to the molecule CC1CN(C(C[NH3+])c2cc(F)ccc2Br)CCCO1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1CN(C(C[NH3+])c2cc(F)ccc2Br)CCCO1.",
"ref_smiles": "CC1(c2ccccc2)CN(C(C[NH3+])c2cc(F)ccc2Br)CCCO1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "3a57a319-792a-4b59-b174-7662cb41888e",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CCOc1ccc(S(=O)(=O)Nc2ccc(Nc3cc(-n4ccnc4)ncn3)cc2)cc1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOc1ccc(S(=O)(=O)Nc2ccc(Nc3cc(-n4ccnc4)ncn3)cc2)cc1C.",
"ref_smiles": "CCOc1ccc(S(=O)(=O)NNc2cc(-n3ccnc3)ncn2)cc1C",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "1a84d80b-4bbc-404d-8145-d25bc10ac1ec",
"task": "add",
"question": "Modify the molecule CC1(C)OC2OC(C3CCCC(=O)N3Cc3ccccc3)C(OCc3ccccc3)C2O1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(C)OC2OC(C3CCCC(=O)N3Cc3ccccc3)C(OCc3ccccc3)C2O1",
"ref_smiles": "CC1(C)OC2OC(C3CCCC(=O)N3Cc3ccccc3)C(OCc3ccccc3)C2(O)O1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "e6f0cecf-bff6-4dd3-9675-43d77ff27126",
"task": "add",
"question": "Please add a hydroxyl to the molecule Cc1nn(C)cc1S(=O)(=O)NCC1CCCC[NH+]1C1CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nn(C)cc1S(=O)(=O)NCC1CCCC[NH+]1C1CC1.",
"ref_smiles": "Cc1nn(C)cc1S(=O)(=O)NCC1C(O)CCC[NH+]1C1CC1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "3f8c82b9-6713-418c-bdda-cfcab0688fd3",
"task": "add",
"question": "Please add a benzene ring to the molecule O=C(NCc1csc2ncnn12)C1CN(c2cc(-n3cccn3)ncn2)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCc1csc2ncnn12)C1CN(c2cc(-n3cccn3)ncn2)C1.",
"ref_smiles": "O=C(NCc1csc2ncnn12)C1CN(c2cc(-n3cc(-c4ccccc4)cn3)ncn2)C1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "188c5739-437b-4169-9e1c-91606252bb71",
"task": "add",
"question": "Modify the molecule O=S(=O)(c1c(F)cc(F)cc1F)N1CCCC(CBr)C1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=S(=O)(c1c(F)cc(F)cc1F)N1CCCC(CBr)C1",
"ref_smiles": "O=S(=O)(c1c(F)cc(F)c(-c2ccccc2)c1F)N1CCCC(CBr)C1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "fa9c30e5-29f6-4b67-b1b2-fe07550cdf66",
"task": "sub",
"question": "Modify the molecule Cc1ccc(CNC(=O)Nc2cc(Cl)ccc2C(=O)[O-])s1 by substituting a halo with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(CNC(=O)Nc2cc(Cl)ccc2C(=O)[O-])s1",
"ref_smiles": "Cc1ccc(CNC(=O)Nc2cc(S)ccc2C(=O)[O-])s1",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "485a37af-bee3-4492-8fc3-c9ce65be1b32",
"task": "add",
"question": "Please add a hydroxyl to the molecule COc1cc(OC)c(S(=O)(=O)N(C)CC(O)CO)cc1-c1ccnn1-c1ccccc1Cl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cc(OC)c(S(=O)(=O)N(C)CC(O)CO)cc1-c1ccnn1-c1ccccc1Cl.",
"ref_smiles": "COc1cc(OC)c(S(=O)(=O)N(C)CC(O)CO)cc1-c1cc(O)nn1-c1ccccc1Cl",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "dda66cea-fcbb-4c6e-bf8f-ea95d0148948",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CC(=O)c1cccc(C(=O)Oc2nc(OC(=O)c3ccccc3)ccc2Cl)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)c1cccc(C(=O)Oc2nc(OC(=O)c3ccccc3)ccc2Cl)c1.",
"ref_smiles": "CC(=O)c1cccc(C(=O)Oc2nc(OC=O)ccc2Cl)c1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "ca04013b-62e6-44b0-8bf2-3f9748403d52",
"task": "sub",
"question": "Please substitute a halo in the molecule CC(O)(C[NH+]=C(N)Nc1ccc(OC(F)(F)F)cc1)c1cccs1 with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(O)(C[NH+]=C(N)Nc1ccc(OC(F)(F)F)cc1)c1cccs1",
"ref_smiles": "CC(O)(C[NH+]=C(N)Nc1ccc(OC(O)(F)F)cc1)c1cccs1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "dc60e855-3cf5-4a19-9cbb-f1521f287a04",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule C[NH2+]C1C2CCC(CO)(O2)C(O)C1O with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH2+]C1C2CCC(CO)(O2)C(O)C1O",
"ref_smiles": "C[NH2+]C1C2CCC(CC(=O)[OH])(O2)C(O)C1O",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "c115ffe9-b224-4a70-8a51-b905be6cc368",
"task": "delete",
"question": "Modify the molecule CCN1c2cc(C(F)(F)F)ccc2CC1CC(C)O by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN1c2cc(C(F)(F)F)ccc2CC1CC(C)O",
"ref_smiles": "CCN1c2cc(C(F)F)ccc2CC1CC(C)O",
"add_group": null,
"remove_group": "halo"
},
{
"id": "fcd02df4-ae36-4e99-875d-7c2b72112777",
"task": "sub",
"question": "Modify the molecule CCCC(O)Cn1ccnc1C by substituting a hydroxyl with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCC(O)Cn1ccnc1C",
"ref_smiles": "CCCC(Cn1ccnc1C)C(=O)O",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "5b293157-11f3-491a-9503-83f7719fb9bd",
"task": "add",
"question": "Please add a hydroxyl to the molecule CSc1nc(N)cc(N2CCCc3ccccc3C2)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CSc1nc(N)cc(N2CCCc3ccccc3C2)n1.",
"ref_smiles": "CSc1nc(N)cc(N2CCC(O)c3ccccc3C2)n1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "d8c205a5-1fbf-4b79-844f-7d6799003efd",
"task": "sub",
"question": "Please substitute a nitrile in the molecule Cc1cc(C)c(C#N)c(N2CC(C)[NH2+]CC2C)n1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C)c(C#N)c(N2CC(C)[NH2+]CC2C)n1",
"ref_smiles": "CC(=O)c1c(C)cc(C)nc1N1CC(C)[NH2+]CC1C",
"add_group": "aldehyde",
"remove_group": "nitrile"
},
{
"id": "22cbe031-a507-4cc1-9b16-d37cf9325ad4",
"task": "delete",
"question": "Please remove a amide from the molecule CC(=O)N(CC(=O)Nc1cc(C)cc(C)c1)c1ccc(N2CCCC2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)N(CC(=O)Nc1cc(C)cc(C)c1)c1ccc(N2CCCC2)cc1.",
"ref_smiles": "Cc1cc(C)cc(NC(=O)Cc2ccc(N3CCCC3)cc2)c1",
"add_group": null,
"remove_group": "amide"
},
{
"id": "6ad2e6fc-1425-40f9-ba53-2ca6440beb6c",
"task": "delete",
"question": "Modify the molecule CCc1ccc(-c2nccn2S(C)(=O)=O)cc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1ccc(-c2nccn2S(C)(=O)=O)cc1",
"ref_smiles": "CCc1nccn1S(C)(=O)=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "21f40456-ab16-49a9-b053-ec211118f868",
"task": "delete",
"question": "Please remove a halo from the molecule CC(C)C(C)Nc1ccc(Br)nc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)C(C)Nc1ccc(Br)nc1.",
"ref_smiles": "CC(C)C(C)Nc1cccnc1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "f97bfcc2-0ce0-4d24-8153-ff1b2affd7da",
"task": "add",
"question": "Please add a benzene ring to the molecule CC1CC[NH+](CCNC(=O)c2cc(C3CC3)n(C(C)(C)C)n2)CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1CC[NH+](CCNC(=O)c2cc(C3CC3)n(C(C)(C)C)n2)CC1.",
"ref_smiles": "CC1CC[NH+](C(CNC(=O)c2cc(C3CC3)n(C(C)(C)C)n2)c2ccccc2)CC1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "cba2de45-c05b-4b84-8bec-1ff126d1a3d2",
"task": "delete",
"question": "Modify the molecule Cc1cc(N2CCC(Nc3cc(CO)ccc3[N+](=O)[O-])CC2)nc(C)n1 by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(N2CCC(Nc3cc(CO)ccc3[N+](=O)[O-])CC2)nc(C)n1",
"ref_smiles": "Cc1cc(N2CCC(c3cc(CO)ccc3[N+](=O)[O-])CC2)nc(C)n1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "7667bdda-fbfd-44bf-a505-47cc464ae2a9",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CN1C(=O)CCC1(O)CC#C[Si](C)(C)C with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN1C(=O)CCC1(O)CC#C[Si](C)(C)C",
"ref_smiles": "CN1C(=O)CCC1(S)CC#C[Si](C)(C)C",
"add_group": "thiol",
"remove_group": "hydroxyl"
},
{
"id": "c2bdde61-7744-4bf0-8651-f9644bbe3b25",
"task": "add",
"question": "Modify the molecule CC(C)(C)OC(=O)N1CCC(Nc2cccc(C(N)=O)c2)C1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cccc(C(N)=O)c2)C1",
"ref_smiles": "CC(C)(C)OC(=O)N1CCC(Nc2cccc(C(N)=O)c2)(c2ccccc2)C1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "d364eac4-764a-4f18-8cb2-6711829e9498",
"task": "add",
"question": "Modify the molecule Cn1cnnc1C[NH2+]Cc1ccccc1-n1cccn1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cn1cnnc1C[NH2+]Cc1ccccc1-n1cccn1",
"ref_smiles": "Cn1cnnc1C[NH2+]Cc1ccccc1-n1nccc1O",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "4cda2005-0e42-4fbc-a202-db06c0feeacc",
"task": "add",
"question": "Modify the molecule Nc1ccc(CNC(=O)C(Cc2cccc3ccccc23)NC(=O)C2CCCC[NH2+]2)cn1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Nc1ccc(CNC(=O)C(Cc2cccc3ccccc23)NC(=O)C2CCCC[NH2+]2)cn1",
"ref_smiles": "Nc1ccc(CNC(=O)C(Cc2cccc3ccccc23)NC(=O)C2CCCC[NH2+]2)c(-c2ccccc2)n1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "9b394ce5-348b-46cf-b66d-0281f695503f",
"task": "sub",
"question": "Please substitute a halo in the molecule CNC(=O)c1ccc(NC(=O)C(C)NC(=O)C2CC[NH+](C(C)C(=O)Nc3cc(C(=O)Nc4ccccc4)ccc3C)CC2)cc1Cl with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CNC(=O)c1ccc(NC(=O)C(C)NC(=O)C2CC[NH+](C(C)C(=O)Nc3cc(C(=O)Nc4ccccc4)ccc3C)CC2)cc1Cl",
"ref_smiles": "CNC(=O)c1ccc(NC(=O)C(C)NC(=O)C2CC[NH+](C(C)C(=O)Nc3cc(C(=O)Nc4ccccc4)ccc3C)CC2)cc1O",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "6ddef6d3-f1ef-406a-8a80-3478a601fd77",
"task": "sub",
"question": "Please substitute a halo in the molecule CC=C(C#CCN1CCS(=O)CC1)[NH+]=C1C(=C(C)C)[NH2+]CCN1Cc1c(C)ccc(F)c1O with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC=C(C#CCN1CCS(=O)CC1)[NH+]=C1C(=C(C)C)[NH2+]CCN1Cc1c(C)ccc(F)c1O",
"ref_smiles": "CC(=O)c1ccc(C)c(CN2CC[NH2+]C(=C(C)C)C2=[NH+]C(C#CCN2CCS(=O)CC2)=CC)c1O",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "05dc9fdf-fb8e-4d9b-b4d0-ff0953a508c1",
"task": "sub",
"question": "Please substitute a halo in the molecule CC1CCC(CCN2CCNCC(C(F)(F)F)C2)CC1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1CCC(CCN2CCNCC(C(F)(F)F)C2)CC1",
"ref_smiles": "CC(=O)C(F)(F)C1CNCCN(CCC2CCC(C)CC2)C1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "bde6bde0-ff87-4b3d-b872-d0e18e889185",
"task": "delete",
"question": "Please remove a halo from the molecule CC(c1ccc(Cl)cc1)[NH+](C)CC(=O)C(C)(C)C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(c1ccc(Cl)cc1)[NH+](C)CC(=O)C(C)(C)C.",
"ref_smiles": "CC(c1ccccc1)[NH+](C)CC(=O)C(C)(C)C",
"add_group": null,
"remove_group": "halo"
},
{
"id": "356f97c7-9e19-4ca7-8e32-014f6c47c384",
"task": "sub",
"question": "Modify the molecule BrN1C=CCn2c1nc1c3ccccc3[nH]c12 by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "BrN1C=CCn2c1nc1c3ccccc3[nH]c12",
"ref_smiles": "ON1C=CCn2c1nc1c3ccccc3[nH]c12",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "b2c921e9-a53a-4712-b9b6-130aea337b63",
"task": "add",
"question": "Please add a benzene ring to the molecule CCNC(C)(C#N)CCCCn1ncc(Cl)c1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCNC(C)(C#N)CCCCn1ncc(Cl)c1C.",
"ref_smiles": "CCNC(C)(C#N)CCCCn1ncc(Cl)c1Cc1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "938f531d-1d62-413b-bc73-6fd7015584e0",
"task": "add",
"question": "Modify the molecule Cc1onc(-c2ccccc2)c1-c1cn2cc(-n3cccc3)ccc2[nH+]1 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1onc(-c2ccccc2)c1-c1cn2cc(-n3cccc3)ccc2[nH+]1",
"ref_smiles": "Cc1onc(-c2cccc(C(=O)O)c2)c1-c1cn2cc(-n3cccc3)ccc2[nH+]1",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "de559119-a685-46dd-827e-5a9ffb31a508",
"task": "delete",
"question": "Please remove a amide from the molecule CC(CCO)NC(=O)c1n[nH]c(C2CC2)c1N.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(CCO)NC(=O)c1n[nH]c(C2CC2)c1N.",
"ref_smiles": "CC(CCO)n1[nH]c(C2CC2)c-1N",
"add_group": null,
"remove_group": "amide"
},
{
"id": "ead7e92e-2e41-4ea3-88a5-309fead20d3e",
"task": "sub",
"question": "Please substitute a halo in the molecule COc1cc(C)nc(CBr)c1C(F)F with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cc(C)nc(CBr)c1C(F)F",
"ref_smiles": "CC(=O)Cc1nc(C)cc(OC)c1C(F)F",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "d4b7fd03-865f-432e-8366-184ad509ae7f",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1c(F)cccc1NC(=O)CSc1nc(N)c(C#N)c(-c2cccs2)c1C#N with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(F)cccc1NC(=O)CSc1nc(N)c(C#N)c(-c2cccs2)c1C#N",
"ref_smiles": "Cc1c(C#N)cccc1NC(=O)CSc1nc(N)c(C#N)c(-c2cccs2)c1C#N",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "63f4868b-ac17-4d3a-bd40-1a3936ba67b0",
"task": "delete",
"question": "Modify the molecule O=C(NCC(=O)N1CCCC1)Nc1ccc(N2CCSCC2)c(Cl)c1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCC(=O)N1CCCC1)Nc1ccc(N2CCSCC2)c(Cl)c1",
"ref_smiles": "O=C(CNC(=O)N(Cl)N1CCSCC1)N1CCCC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "aed478c1-1170-41c1-9c7d-468a41fa3851",
"task": "sub",
"question": "Please substitute a halo in the molecule CN(C)c1cc(C(F)(F)F)nc(NCc2cnn(-c3ccccc3)c2)n1 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(C)c1cc(C(F)(F)F)nc(NCc2cnn(-c3ccccc3)c2)n1",
"ref_smiles": "CN(C)c1cc(C(F)(F)C(=O)O)nc(NCc2cnn(-c3ccccc3)c2)n1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "29389218-1691-42c3-ab57-18a615092bc5",
"task": "add",
"question": "Please add a benzene ring to the molecule COC(=O)Nc1ccc(C(=O)NC(CC(C)(C)OC)C(=O)N2CCCC3(C2)OC(=O)Nc2ccc(Cl)c(F)c23)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)Nc1ccc(C(=O)NC(CC(C)(C)OC)C(=O)N2CCCC3(C2)OC(=O)Nc2ccc(Cl)c(F)c23)cc1.",
"ref_smiles": "COC(=O)Nc1ccc(C(=O)NC(CC(C)(C)OC)C(=O)N2CC(c3ccccc3)CC3(C2)OC(=O)Nc2ccc(Cl)c(F)c23)cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "f10cd33c-0394-4bfd-93ad-2d863f0e721f",
"task": "delete",
"question": "Please remove a halo from the molecule COc1ccc(NC(=O)N(C)CCOc2ccccc2F)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(NC(=O)N(C)CCOc2ccccc2F)cc1.",
"ref_smiles": "COc1ccc(NC(=O)N(C)CCOc2ccccc2)cc1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "3353939f-e01c-43b8-a1f5-ee31e80e73bd",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(Nc1c2c(cc3c1OCC3)OCC2)c1ccc(Cl)cc1 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(Nc1c2c(cc3c1OCC3)OCC2)c1ccc(Cl)cc1",
"ref_smiles": "N#Cc1ccc(C(=O)Nc2c3c(cc4c2OCC4)OCC3)cc1",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "7f1e5f43-906d-49f6-afa7-565d0f71970c",
"task": "delete",
"question": "Modify the molecule CCN1CC[NH+](Cc2ccc(NC(=O)Nc3ccc(Cl)c(Oc4ncnc5c4OCCN5)c3)cc2C(F)(F)F)CC1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCN1CC[NH+](Cc2ccc(NC(=O)Nc3ccc(Cl)c(Oc4ncnc5c4OCCN5)c3)cc2C(F)(F)F)CC1",
"ref_smiles": "CCN1CC[NH+](CN(C(=O)Nc2ccc(Cl)c(Oc3ncnc4c3OCCN4)c2)C(F)(F)F)CC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "8e9238f1-6d18-4732-8e1c-fceb93d05859",
"task": "delete",
"question": "Modify the molecule Cc1nc(C)c(C#N)c(SCC(=O)NC(C)C)n1 by removing a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nc(C)c(C#N)c(SCC(=O)NC(C)C)n1",
"ref_smiles": "Cc1cc(SCC(=O)NC(C)C)nc(C)n1",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "1432fc96-8dbb-4710-bdaa-793f0a4f1f66",
"task": "sub",
"question": "Please substitute a halo in the molecule COc1cc(-c2nc(=O)n(-c3c(Cl)cccc3Cl)[nH]2)ccc1I with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cc(-c2nc(=O)n(-c3c(Cl)cccc3Cl)[nH]2)ccc1I",
"ref_smiles": "COc1cc(-c2nc(=O)n(-c3c(Cl)cccc3CHO)[nH]2)ccc1I",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "22c221ca-4547-4414-be0b-abd0411ee878",
"task": "add",
"question": "Modify the molecule C#CC(OC1CCCCO1)C(C)(C)CCOCCOCCC(C)(C)CO[Si](C)(C)C(C)(C)C by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C#CC(OC1CCCCO1)C(C)(C)CCOCCOCCC(C)(C)CO[Si](C)(C)C(C)(C)C",
"ref_smiles": "C#CC(OC1CCCCO1)C(C)(C)CCOCCOCCC(C)(CO)CO[Si](C)(C)C(C)(C)C",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "0dbf981f-128c-4fc0-b72f-6f705825ad8b",
"task": "delete",
"question": "Please remove a amide from the molecule CCC(COC)NC(=O)Cc1ccccc1O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(COC)NC(=O)Cc1ccccc1O.",
"ref_smiles": "CCC(COC)c1ccccc1O",
"add_group": null,
"remove_group": "amide"
},
{
"id": "336ef415-6e21-4daf-927d-bf5f28bb3637",
"task": "add",
"question": "Please add a hydroxyl to the molecule Clc1ccnc2c1ccc1ncncc12.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Clc1ccnc2c1ccc1ncncc12.",
"ref_smiles": "Oc1cc2ncncc2c2nccc(Cl)c12",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "6f8cce8a-44f8-45d0-b0c5-c0f7cd921141",
"task": "add",
"question": "Please add a aldehyde to the molecule C#CC(CC)NC(=O)C1(C[NH3+])CCCC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C#CC(CC)NC(=O)C1(C[NH3+])CCCC1.",
"ref_smiles": "C#CC(NC(=O)C1(C[NH3+])CCCC1)C(C)CC=O",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "c1f30bc4-d803-4577-b0fa-35b50aaea6cd",
"task": "delete",
"question": "Modify the molecule COc1ccc(F)c2[nH]c(C(=O)NCC3(O)C4C5CC6C7C5CC4C7C63)cc12 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(F)c2[nH]c(C(=O)NCC3(O)C4C5CC6C7C5CC4C7C63)cc12",
"ref_smiles": "COc1ccc(F)c2[nH]c(C(=O)NCC3C4C5CC6C7C5CC4C7C36)cc12",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "ef02bc88-6c0b-41bb-b309-3e49acd8fab3",
"task": "add",
"question": "Modify the molecule CC(C)Oc1ccccc1C1C[NH2+]CCC1C by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)Oc1ccccc1C1C[NH2+]CCC1C",
"ref_smiles": "CC(C)Oc1ccccc1C1(c2ccccc2)C[NH2+]CCC1C",
"add_group": "benzene",
"remove_group": null
},
{
"id": "93a0c520-8ccb-45bb-91cd-9cf15bead5bc",
"task": "add",
"question": "Please add a amine to the molecule O=C1C(Cc2ccccc2)CCC2C=CN(c3ccccc3)N1C2.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C1C(Cc2ccccc2)CCC2C=CN(c3ccccc3)N1C2.",
"ref_smiles": "Nc1ccccc1CC1CCC2C=CN(c3ccccc3)N(C2)C1=O",
"add_group": "amine",
"remove_group": null
},
{
"id": "be8f5383-a521-4984-9771-e48bdd48c062",
"task": "add",
"question": "Please add a benzene ring to the molecule CCCCCCCCCCOc1ccc(-c2ccc(OC(=O)c3c(F)c(F)c(F)c(F)c3F)cc2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCCCCCCOc1ccc(-c2ccc(OC(=O)c3c(F)c(F)c(F)c(F)c3F)cc2)cc1.",
"ref_smiles": "CCCCCCCCCCOc1ccc(-c2ccc(OC(=O)c3c(F)c(F)c(F)c(F)c3F)cc2-c2ccccc2)cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "1e4c12c3-0695-45e9-8b3f-af7d3a7c52c2",
"task": "delete",
"question": "Please remove a nitrile from the molecule CC(C)C(C)(C)[Si](C)(C)OCN1C=CC(c2ccccc2)C(C#N)=C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)C(C)(C)[Si](C)(C)OCN1C=CC(c2ccccc2)C(C#N)=C1.",
"ref_smiles": "CC(C)C(C)(C)[Si](C)(C)OCN1C=CC(c2ccccc2)C=C1",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "09413341-29d7-42ac-9ab6-644b020b3c0f",
"task": "delete",
"question": "Please remove a amine from the molecule CC1(C)CCC(Nc2nc(C(C)(C)C)ns2)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(C)CCC(Nc2nc(C(C)(C)C)ns2)C1.",
"ref_smiles": "CC1(C)CCC(c2nc(C(C)(C)C)ns2)C1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "0e9c96b7-a474-4fe4-ad51-244ddc772306",
"task": "add",
"question": "Please add a hydroxyl to the molecule Cc1cccc(CC2CC(C(C)(C)C)CCC2C[NH3+])c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cccc(CC2CC(C(C)(C)C)CCC2C[NH3+])c1.",
"ref_smiles": "Cc1cc(O)cc(CC2CC(C(C)(C)C)CCC2C[NH3+])c1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "f7f61887-8511-40f9-a674-45c2746d944b",
"task": "delete",
"question": "Please remove a hydroxyl from the molecule C=C(C)C(=O)OCC(O)CC(F)(F)C(F)(F)C(F)(C(F)(F)F)C(F)(F)F.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=C(C)C(=O)OCC(O)CC(F)(F)C(F)(F)C(F)(C(F)(F)F)C(F)(F)F.",
"ref_smiles": "C=C(C)C(=O)OCCCC(F)(F)C(F)(F)C(F)(C(F)(F)F)C(F)(F)F",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "85c28c2b-75db-4c7c-b620-82cf7d5a417e",
"task": "add",
"question": "Modify the molecule COc1ccccc1C[NH+](C)CC1(C[NH3+])CCCC(C)C1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccccc1C[NH+](C)CC1(C[NH3+])CCCC(C)C1",
"ref_smiles": "COc1ccccc1C(c1ccccc1)[NH+](C)CC1(C[NH3+])CCCC(C)C1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "3005e1e4-838d-4ef4-bf22-ac523c6ff5c8",
"task": "delete",
"question": "Modify the molecule O=C([O-])CCCNC(=O)NC1CCOc2ccc(Br)cc21 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C([O-])CCCNC(=O)NC1CCOc2ccc(Br)cc21",
"ref_smiles": "O=C([O-])CCCNC(=O)NC1CCOc2ccccc21",
"add_group": null,
"remove_group": "halo"
},
{
"id": "28e6f22f-1672-4663-92ab-8383fd4bf2ea",
"task": "delete",
"question": "Modify the molecule CC(CO)C(C)Nc1ccc(S(C)(=O)=O)cc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(CO)C(C)Nc1ccc(S(C)(=O)=O)cc1",
"ref_smiles": "CC(CO)C(C)NS(C)(=O)=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "72339bd9-0769-419f-aebb-3a5028f190cb",
"task": "add",
"question": "Please add a benzene ring to the molecule O=c1cc(CSc2ccc(Cl)cc2)[nH]c(N2CCN(c3ccccn3)CC2)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=c1cc(CSc2ccc(Cl)cc2)[nH]c(N2CCN(c3ccccn3)CC2)n1.",
"ref_smiles": "O=c1cc(CSc2ccc(Cl)c(-c3ccccc3)c2)[nH]c(N2CCN(c3ccccn3)CC2)n1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "e16724d1-413e-47b7-8a48-5e4d44714e90",
"task": "sub",
"question": "Modify the molecule CCc1ccc(F)cc1-n1c(C=C(C)C)c(C(=O)N2CC[NH2+]CC2)cc(-c2nc(-c3ccc(C(F)(F)F)nc3)cs2)c1=O by substituting a halo with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1ccc(F)cc1-n1c(C=C(C)C)c(C(=O)N2CC[NH2+]CC2)cc(-c2nc(-c3ccc(C(F)(F)F)nc3)cs2)c1=O",
"ref_smiles": "CCc1ccc(C#N)cc1-n1c(C=C(C)C)c(C(=O)N2CC[NH2+]CC2)cc(-c2nc(-c3ccc(C(F)(F)F)nc3)cs2)c1=O",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "59c6198c-ceaf-452d-aa18-1af23aa5f470",
"task": "sub",
"question": "Please substitute a halo in the molecule COc1c(C#N)cc(F)c(S(C)(=O)=O)c1OC with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1c(C#N)cc(F)c(S(C)(=O)=O)c1OC",
"ref_smiles": "COc1c(C#N)cc([N+](=O)[O-])c(S(C)(=O)=O)c1OC",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "d79ac474-42e9-41c4-8b17-a413b68e40df",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule COc1ccc(C(CCCCC(=O)NO)C2=C(C)C(=O)c3ccccc3C2=O)cc1 with a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(C(CCCCC(=O)NO)C2=C(C)C(=O)c3ccccc3C2=O)cc1",
"ref_smiles": "COc1ccc(C(CCCCC(=O)NCl)C2=C(C)C(=O)c3ccccc3C2=O)cc1",
"add_group": "halo",
"remove_group": "hydroxyl"
},
{
"id": "fc419e80-4226-4177-a896-0bf05518630e",
"task": "sub",
"question": "Please substitute a halo in the molecule CNc1nc(N(C)Cc2ccccc2OC)c(Cl)cc1Cl with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CNc1nc(N(C)Cc2ccccc2OC)c(Cl)cc1Cl",
"ref_smiles": "CNc1nc(N(C)Cc2ccccc2OC)c(C#N)cc1Cl",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "268c02ac-fb8e-4556-ae4f-b883924dade1",
"task": "sub",
"question": "Please substitute a halo in the molecule CCCC(C)(C[NH3+])Cc1c(Cl)c(C)nn1C with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCC(C)(C[NH3+])Cc1c(Cl)c(C)nn1C",
"ref_smiles": "CCCC(C)(C[NH3+])Cc1c(O)c(C)nn1C",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "95e3262a-80e4-4db0-971b-b7d2db5694a3",
"task": "delete",
"question": "Please remove a amide from the molecule CN1C(=O)CC(C(=O)NCC[NH+]2CCOC(C)(C)C2)C1c1ccnn1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN1C(=O)CC(C(=O)NCC[NH+]2CCOC(C)(C)C2)C1c1ccnn1C.",
"ref_smiles": "CN1C(=O)CC1(CC[NH+]1CCOC(C)(C)C1)c1ccnn1C",
"add_group": null,
"remove_group": "amide"
},
{
"id": "6ef36ddc-fc72-462b-989c-bff7a7542052",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CCCCOC1C(OCC(C)C)OC(COC(=O)NCCC)C(OC(=O)Nc2ccc(C(F)(F)F)cc2)C1OCCC.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCOC1C(OCC(C)C)OC(COC(=O)NCCC)C(OC(=O)Nc2ccc(C(F)(F)F)cc2)C1OCCC.",
"ref_smiles": "CCCCOC1C(OCC(C)C)OC(COC(=O)NCCC)C(OC(=O)NC(F)(F)F)C1OCCC",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "adf7b772-280a-4b8a-ac45-536318b923aa",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CCCCOC(=O)P(C(=O)OCC)c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCOC(=O)P(C(=O)OCC)c1ccccc1.",
"ref_smiles": "CCCCOC(=O)PC(=O)OCC",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "e764b341-a0a5-4a35-88c1-0205f084f232",
"task": "sub",
"question": "Please substitute a halo in the molecule CCc1csc(C2CCCN(c3ncnc(N)c3Cl)C2)n1 with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1csc(C2CCCN(c3ncnc(N)c3Cl)C2)n1",
"ref_smiles": "CCc1csc(C2CCCN(c3ncnc(N)c3NO)C2)n1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "89a86e22-90d9-4c3a-889b-e83eeb99eebb",
"task": "delete",
"question": "Please remove a amine from the molecule CC(C#N)NC(C)c1ccc(Br)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C#N)NC(C)c1ccc(Br)cc1.",
"ref_smiles": "CC(C#N)C(C)c1ccc(Br)cc1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "3de6116f-49b3-4b2c-a477-877b4aa51aeb",
"task": "add",
"question": "Please add a aldehyde to the molecule C=C(NNC(=O)CN(c1ccc(C)cc1)S(=O)(=O)c1ccccc1)c1ccc(OC)c(OC)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=C(NNC(=O)CN(c1ccc(C)cc1)S(=O)(=O)c1ccccc1)c1ccc(OC)c(OC)c1.",
"ref_smiles": "C=C(NNC(=O)CN(c1ccc(C)c(CC=O)c1)S(=O)(=O)c1ccccc1)c1ccc(OC)c(OC)c1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "fe0104f4-3fe9-4975-883f-604cbe083c1e",
"task": "sub",
"question": "Please substitute a halo in the molecule CC(C)CCCNC(=O)NCc1cccc(OCC(F)F)c1 with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)CCCNC(=O)NCc1cccc(OCC(F)F)c1",
"ref_smiles": "CC(C)CCCNC(=O)NCc1cccc(OCC(O)F)c1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "bdbee59d-a1a9-4f12-9176-1298c94d3903",
"task": "add",
"question": "Modify the molecule Cc1ccc(-c2noc(C3CC[NH2+]CC3)n2)cc1Br by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(-c2noc(C3CC[NH2+]CC3)n2)cc1Br",
"ref_smiles": "Cc1ccc(-c2noc(C3CC[NH2+]C(c4ccccc4)C3)n2)cc1Br",
"add_group": "benzene",
"remove_group": null
},
{
"id": "d338a93a-64a2-4c6a-8747-89dc7e49d513",
"task": "add",
"question": "Modify the molecule CCOC1(C(=O)Nc2ccc(OC)c(C(F)(F)F)c2)CCCCCC1 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC1(C(=O)Nc2ccc(OC)c(C(F)(F)F)c2)CCCCCC1",
"ref_smiles": "CCOC1(C(=O)Nc2ccc(OC)c(C(F)(F)F)c2)CCCCCC1N",
"add_group": "amine",
"remove_group": null
},
{
"id": "0a98e866-d5e6-4a0c-acbf-5470487163f0",
"task": "add",
"question": "Please add a hydroxyl to the molecule N=C1C=NC2=CN=C[N+]2([NH3+])C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "N=C1C=NC2=CN=C[N+]2([NH3+])C1.",
"ref_smiles": "N=C1C=NC2=CN=C(O)[N+]2([NH3+])C1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "e3b06d58-4ec5-4ab8-ba7b-a5efd08b258b",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CCO[P+]([O-])(OCC)C(NC1C(O)OC(CO)C(O)C1O)c1ccc(CC)cc1 with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCO[P+]([O-])(OCC)C(NC1C(O)OC(CO)C(O)C1O)c1ccc(CC)cc1",
"ref_smiles": "CCO[P+]([O-])(OCC)C(NC1C(S)OC(CO)C(O)C1O)c1ccc(CC)cc1",
"add_group": "thiol",
"remove_group": "hydroxyl"
},
{
"id": "ebe71287-5d90-45c9-98e5-488282f7ddd7",
"task": "add",
"question": "Please add a benzene ring to the molecule CC[NH+]1CCN(C(=O)C(C)(C)C(=O)N2CCN(c3ncccn3)CC2)CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC[NH+]1CCN(C(=O)C(C)(C)C(=O)N2CCN(c3ncccn3)CC2)CC1.",
"ref_smiles": "CC[NH+]1CCN(C(=O)C(C)(C)C(=O)N2CCN(c3ncccn3)CC2)CC1c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "86c1fc39-9ad2-4d08-8ba3-d86e2540479e",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1ncccc1Oc1ccc(C=O)cc1F with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ncccc1Oc1ccc(C=O)cc1F",
"ref_smiles": "Cc1ncccc1Oc1ccc(C=O)cc1S",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "d8892824-0c22-40e5-adf2-c81da77d803b",
"task": "delete",
"question": "Please remove a benzene ring from the molecule COC(=O)c1cc(C(=O)OC)n(-c2ccc(OC)cc2)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)c1cc(C(=O)OC)n(-c2ccc(OC)cc2)n1.",
"ref_smiles": "COC(=O)c1cc(C(=O)OC)n(OC)n1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "04176db3-1b4c-4026-bc4f-d71932fa92c3",
"task": "add",
"question": "Modify the molecule CCC1CC1Nc1nc2c(cc1C#N)CCCC2 by adding a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC1CC1Nc1nc2c(cc1C#N)CCCC2",
"ref_smiles": "CCC1CC1Nc1nc2c(cc1C#N)CC(C#N)CC2",
"add_group": "nitrile",
"remove_group": null
},
{
"id": "d6e8d741-5a10-466c-8710-afb576bfedaf",
"task": "delete",
"question": "Modify the molecule COCc1noc(C[NH+]2CCN(c3nc4c(cc3C#N)CCCC4)CC2)n1 by removing a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCc1noc(C[NH+]2CCN(c3nc4c(cc3C#N)CCCC4)CC2)n1",
"ref_smiles": "COCc1noc(C[NH+]2CCN(c3ccc4c(n3)CCCC4)CC2)n1",
"add_group": null,
"remove_group": "nitrile"
},
{
"id": "88fb0c75-3aa5-4b69-b9f1-563cf7868c5a",
"task": "delete",
"question": "Modify the molecule C[NH+](C)Cc1cc(CC2CC([NH2+]Cc3ccccc3O)C2(C)C)no1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH+](C)Cc1cc(CC2CC([NH2+]Cc3ccccc3O)C2(C)C)no1",
"ref_smiles": "C[NH+](C)Cc1cc(CC2CC([NH2+]CO)C2(C)C)no1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "2e8938dc-fed2-4494-8227-d78527701f6f",
"task": "delete",
"question": "Modify the molecule Cc1c(C(=O)Nc2c(C)n(C)n(C3CCCCC3)c2=O)noc1CCC(C)(C)C by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1c(C(=O)Nc2c(C)n(C)n(C3CCCCC3)c2=O)noc1CCC(C)(C)C",
"ref_smiles": "Cc1c(CCC(C)(C)C)on-1-c1c(C)n(C)n(C2CCCCC2)c1=O",
"add_group": null,
"remove_group": "amide"
},
{
"id": "5e601ae9-8dd1-4ad5-88e3-86e8a5aefb1e",
"task": "add",
"question": "Modify the molecule Cc1ccc(Br)c(C)c1 by adding a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(Br)c(C)c1",
"ref_smiles": "Cc1ccc(Br)c(CCC=O)c1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "7f45a3c3-2de5-43ca-8815-48be87b145f1",
"task": "add",
"question": "Please add a aldehyde to the molecule CC(C)Oc1cccc(C([O-])=C2C(=O)C(=O)N(c3ccc(N(C)C)cc3)C2c2cccc(Oc3ccccc3)c2)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)Oc1cccc(C([O-])=C2C(=O)C(=O)N(c3ccc(N(C)C)cc3)C2c2cccc(Oc3ccccc3)c2)c1.",
"ref_smiles": "CC(C)Oc1cccc(C([O-])=C2C(=O)C(=O)N(c3ccc(N(C)C)cc3)C2c2cccc(Oc3ccc(C=O)cc3)c2)c1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "1147c84a-a43d-4e20-8e9c-c5ab5b378e3a",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(NCc1ccc(Br)cc1)c1cc(Br)sc1Br with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCc1ccc(Br)cc1)c1cc(Br)sc1Br",
"ref_smiles": "ONc1ccc(CNC(=O)c2cc(Br)sc2Br)cc1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "86b3c941-c527-49be-b572-54b820b538f9",
"task": "delete",
"question": "Modify the molecule Cc1nn(C)cc1CNC(=O)C(C)C(C)C(=O)[O-] by removing a amide.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1nn(C)cc1CNC(=O)C(C)C(C)C(=O)[O-]",
"ref_smiles": "Cc1nn(C)cc1CC(C)(C)C(=O)[O-]",
"add_group": null,
"remove_group": "amide"
},
{
"id": "fb938603-35ee-48f8-a23a-f2378e3124bc",
"task": "add",
"question": "Please add a benzene ring to the molecule CCCCCCCCCCC(CCCCCCCC)C(=O)OCCCCCCCC.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCCCCCCC(CCCCCCCC)C(=O)OCCCCCCCC.",
"ref_smiles": "CCCCCCCCCCC(CCC(CCCCC)c1ccccc1)C(=O)OCCCCCCCC",
"add_group": "benzene",
"remove_group": null
},
{
"id": "7754fdb1-4a19-4a98-ba0e-6a111068ced2",
"task": "add",
"question": "Modify the molecule CN(C(=O)c1ccccc1)c1ccc2c(c1)nc(NC(=O)c1ccc3cc[nH]c3c1)n2CCCN1CCCC1=O by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(C(=O)c1ccccc1)c1ccc2c(c1)nc(NC(=O)c1ccc3cc[nH]c3c1)n2CCCN1CCCC1=O",
"ref_smiles": "CN(C(=O)c1ccccc1)c1ccc2c(c1)nc(NC(=O)c1ccc3cc[nH]c3c1)n2C(CCN1CCCC1=O)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "e819cf55-e87f-4daa-8203-e8dba1a87bc3",
"task": "sub",
"question": "Modify the molecule C=[N+](CCCCCCCCCCCCCCCCCC)CC(=O)OC(CCCCC)C(O)CC=CCC(=O)OC(COC(=O)CC=CCC(O)C(CCCCC)OC(C)=O)COC(=O)CC=CCC(O)C(CCCCC)OC(=O)C[N+](C)(C)CCCCCCCCCCCCCCCCCC by substituting a hydroxyl with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=[N+](CCCCCCCCCCCCCCCCCC)CC(=O)OC(CCCCC)C(O)CC=CCC(=O)OC(COC(=O)CC=CCC(O)C(CCCCC)OC(C)=O)COC(=O)CC=CCC(O)C(CCCCC)OC(=O)C[N+](C)(C)CCCCCCCCCCCCCCCCCC",
"ref_smiles": "C=[N+](CCCCCCCCCCCCCCCCCC)CC(=O)OC(CCCCC)C(S)CC=CCC(=O)OC(COC(=O)CC=CCC(O)C(CCCCC)OC(C)=O)COC(=O)CC=CCC(O)C(CCCCC)OC(=O)C[N+](C)(C)CCCCCCCCCCCCCCCCCC",
"add_group": "thiol",
"remove_group": "hydroxyl"
},
{
"id": "4cce6313-7a7b-42bd-b273-37e43558f265",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule C=CC(=O)NCC(OC(CNC(=O)C=C)c1cc(C)cc(C(C)(C)C)c1O)c1cc(C)cc(C(C)(C)C)c1O with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CC(=O)NCC(OC(CNC(=O)C=C)c1cc(C)cc(C(C)(C)C)c1O)c1cc(C)cc(C(C)(C)C)c1O",
"ref_smiles": "C=CC(=O)NCC(OC(CNC(=O)C=C)c1cc(C=O)cc(C(C)(C)C)c1)c1cc(C)cc(C(C)(C)C)c1",
"add_group": "aldehyde",
"remove_group": "hydroxyl"
},
{
"id": "6ac495c0-1c2d-45ba-a762-288871c125cd",
"task": "delete",
"question": "Modify the molecule Cn1ccnc1S(=O)(=O)Nc1scnc1C(=O)[O-] by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cn1ccnc1S(=O)(=O)Nc1scnc1C(=O)[O-]",
"ref_smiles": "Cn1ccnc1S(=O)(=O)c1scnc1C(=O)[O-]",
"add_group": null,
"remove_group": "amine"
},
{
"id": "8ad9895e-fda2-4dc3-beb8-02657ccd1ff5",
"task": "sub",
"question": "Please substitute a halo in the molecule CN(C)C(=O)c1cccc(Nc2c(NC(c3cccc(C(F)(F)F)c3)C(C)(C)C)c(=O)c2=O)c1O with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(C)C(=O)c1cccc(Nc2c(NC(c3cccc(C(F)(F)F)c3)C(C)(C)C)c(=O)c2=O)c1O",
"ref_smiles": "CN(C)C(=O)c1cccc(Nc2c(NC(c3c(C=O)cccc(C)c3)C(C)(C)C)c(=O)c2=O)c1O",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "3e50b5b4-25c4-4b50-9459-4ae8ecea3896",
"task": "delete",
"question": "Please remove a halo from the molecule CCCCCC1CCC(C2CCC(CCc3c(C)cc(C4CO4)c(C(F)(F)F)c3C(F)(F)F)CC2)CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCC1CCC(C2CCC(CCc3c(C)cc(C4CO4)c(C(F)(F)F)c3C(F)(F)F)CC2)CC1.",
"ref_smiles": "CCCCCC1CCC(C2CCC(CCc3c(C)cc(C4CO4)c(C(F)(F)F)c3C(F)F)CC2)CC1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "db99b629-b771-42cb-b2f6-b855ab34c557",
"task": "add",
"question": "Modify the molecule COC(=O)C1C(CCN=[N+]=[N-])OC(=O)N1C(=O)OC(C)(C)C by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)C1C(CCN=[N+]=[N-])OC(=O)N1C(=O)OC(C)(C)C",
"ref_smiles": "COC(=O)C1C(CC(N=[N+]=[N-])c2ccccc2)OC(=O)N1C(=O)OC(C)(C)C",
"add_group": "benzene",
"remove_group": null
},
{
"id": "c0511ab4-2f50-4820-a3d2-fb594b627a5d",
"task": "sub",
"question": "Modify the molecule N#CC(=CNc1ncn[nH]1)C(=O)NCCCl by substituting a halo with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "N#CC(=CNc1ncn[nH]1)C(=O)NCCCl",
"ref_smiles": "N#CC(=CNc1ncn[nH]1)C(=O)NCCC(=O)[OH]",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "534bf69e-7f7d-49f7-8bcd-fd8c3b98ba58",
"task": "add",
"question": "Modify the molecule CCC(C)(C)C1CCc2c(sc(NC(=O)c3ccncc3)c2C#N)C1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC(C)(C)C1CCc2c(sc(NC(=O)c3ccncc3)c2C#N)C1",
"ref_smiles": "CCC(C)(C)C1CCc2c(sc(NC(=O)c3ccnc(O)c3)c2C#N)C1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "f8875fa0-4ff4-4418-bc2e-b3a24d58a039",
"task": "sub",
"question": "Modify the molecule C[NH+]=C(NCCOc1cccnc1)NCCc1cccc(F)c1 by substituting a halo with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH+]=C(NCCOc1cccnc1)NCCc1cccc(F)c1",
"ref_smiles": "C[NH+]=C(NCCOc1cccnc1)NCCc1cccc(NO)c1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "b95d3039-1401-4e14-92cd-9de1a11723f4",
"task": "delete",
"question": "Please remove a amide from the molecule CC(C)CC(C)OCCC(=O)NCC(=O)[O-].\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)CC(C)OCCC(=O)NCC(=O)[O-].",
"ref_smiles": "CC(C)CC(C)OCCC(=O)[O-]",
"add_group": null,
"remove_group": "amide"
},
{
"id": "ad235cc1-8dc8-42b0-9034-9228b9922d82",
"task": "add",
"question": "Modify the molecule Cc1cc(C)c(S(=O)(=O)NCC(=O)NCCC2=CCCCC2)c(C)c1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C)c(S(=O)(=O)NCC(=O)NCCC2=CCCCC2)c(C)c1",
"ref_smiles": "Cc1cc(C)c(S(=O)(=O)NCC(=O)NCCC2=CCCCC2)c(CO)c1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "1d2274fc-ec23-4ac7-9e3a-7b87a9c6648f",
"task": "sub",
"question": "Modify the molecule CC(C)(C(=O)N1CCN(C(=O)c2ccc(Cl)cc2)CC1)S(=O)(=O)C1CC1 by substituting a halo with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C(=O)N1CCN(C(=O)c2ccc(Cl)cc2)CC1)S(=O)(=O)C1CC1",
"ref_smiles": "CC(C)(C(=O)N1CCN(C(=O)c2ccc(S)cc2)CC1)S(=O)(=O)C1CC1",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "359cbe52-a39a-4747-9ca3-f86d28296c94",
"task": "add",
"question": "Modify the molecule COc1ccc(N2CCOCC2)c2sc(C(=O)NCc3cccnc3)nc12 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(N2CCOCC2)c2sc(C(=O)NCc3cccnc3)nc12",
"ref_smiles": "COc1ccc(N2CCOC(N)C2)c2sc(C(=O)NCc3cccnc3)nc12",
"add_group": "amine",
"remove_group": null
},
{
"id": "7d7b607f-19b4-4c2c-9f43-f18faf219d31",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C1C2C(c3ccc(Cl)cc3)[NH2+]C(Cc3ccccc3)(C(=O)[O-])C2C(=O)N1c1ccc(Cl)cc1Cl with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C1C2C(c3ccc(Cl)cc3)[NH2+]C(Cc3ccccc3)(C(=O)[O-])C2C(=O)N1c1ccc(Cl)cc1Cl",
"ref_smiles": "N#Cc1ccc(C2[NH2+]C(Cc3ccccc3)(C(=O)[O-])C3C(=O)N(c4ccc(Cl)cc4Cl)C(=O)C23)cc1",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "cf15ec60-ea4a-4093-af62-3e638285ba02",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CC(C)(C)OC(=O)N1CC(=O)OC(c2ccccc2)C1c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)OC(=O)N1CC(=O)OC(c2ccccc2)C1c1ccccc1.",
"ref_smiles": "CC(C)(C)OC(=O)N1CC(=O)OC(c2ccccc2)C1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "c1875650-4f7b-4dee-9f77-b630fd41df56",
"task": "add",
"question": "Please add a nitrile to the molecule CC(C)[NH2+]CC(Cc1ccn(C)n1)c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)[NH2+]CC(Cc1ccn(C)n1)c1ccccc1.",
"ref_smiles": "CC(C)[NH2+]CC(Cc1nn(C)cc1C#N)c1ccccc1",
"add_group": "nitrile",
"remove_group": null
},
{
"id": "b6b6c7f0-1f27-414b-803e-74d0b1fde4eb",
"task": "delete",
"question": "Modify the molecule COc1ccc(CC(C(=O)[O-])C(=O)[O-])cc1CCOC(=O)Nc1ccc(Cl)cc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(CC(C(=O)[O-])C(=O)[O-])cc1CCOC(=O)Nc1ccc(Cl)cc1",
"ref_smiles": "COc1ccc(CC(C(=O)[O-])C(=O)[O-])cc1CCOC(=O)NCl",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "b9f5970d-9516-4c97-bf93-1ca3004b5eef",
"task": "delete",
"question": "Modify the molecule CCCCCNC(=O)Nc1cc(-c2ccc(Cl)c(Cl)c2)sc1C(=O)[O-] by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCNC(=O)Nc1cc(-c2ccc(Cl)c(Cl)c2)sc1C(=O)[O-]",
"ref_smiles": "CCCCCNC(=O)Nc1cc(-c2ccc(Cl)cc2)sc1C(=O)[O-]",
"add_group": null,
"remove_group": "halo"
},
{
"id": "61d7758f-a5f3-4672-8b70-ebd685c3e60b",
"task": "add",
"question": "Please add a thiol to the molecule CN(CCCC(=O)OC12CCCCC1CCCC2)c1ccc(C2=C(O)C(=C3C=CC(=[N+](C)CCCC(=O)OC45CCCCC4CCCC5)C=C3)C2=O)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(CCCC(=O)OC12CCCCC1CCCC2)c1ccc(C2=C(O)C(=C3C=CC(=[N+](C)CCCC(=O)OC45CCCCC4CCCC5)C=C3)C2=O)cc1.",
"ref_smiles": "CN(CCCC(=O)OC12CCCCC1CCCC2)c1ccc(C2=C(O)C(=C3C=CC(=[N+](C)CCCC(=O)OC45CCCCC4CCCC5)C(S)=C3)C2=O)cc1",
"add_group": "thiol",
"remove_group": null
},
{
"id": "2e36010a-cbd1-4986-ad0e-34840c467473",
"task": "add",
"question": "Modify the molecule CCOC(=O)C(OC(=O)c1cccc(OC)c1OC)c1ccc(Br)cc1F by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(=O)C(OC(=O)c1cccc(OC)c1OC)c1ccc(Br)cc1F",
"ref_smiles": "COc1cccc(C(=O)OC(C(=O)OC(C)c2ccccc2)c2ccc(Br)cc2F)c1OC",
"add_group": "benzene",
"remove_group": null
},
{
"id": "7c077930-7fe3-47ba-8d22-6ab944a9a548",
"task": "delete",
"question": "Modify the molecule Cc1cc(C(=O)N2CCCC(C)C2)ccc1NC(=O)CCNC(=O)C1CC[NH+](C(C)C(=O)Nc2cccc(C(=O)N3CCCC(C)C3)c2C)CC1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cc(C(=O)N2CCCC(C)C2)ccc1NC(=O)CCNC(=O)C1CC[NH+](C(C)C(=O)Nc2cccc(C(=O)N3CCCC(C)C3)c2C)CC1",
"ref_smiles": "Cc1c(NC(=O)C(C)[NH+]2CCC(C(=O)NCCC(=O)N(C)C(=O)N3CCCC(C)C3)CC2)cccc1C(=O)N1CCCC(C)C1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "3baf0461-ff56-4ecb-a507-87ce77bbc14d",
"task": "sub",
"question": "Modify the molecule C[N+](C)(Cc1ccc(NC(=O)C2=Cc3c(Cl)cc(Cl)cc3OC2)cc1)C1CCOCC1 by substituting a halo with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[N+](C)(Cc1ccc(NC(=O)C2=Cc3c(Cl)cc(Cl)cc3OC2)cc1)C1CCOCC1",
"ref_smiles": "C[N+](C)(Cc1ccc(NC(=O)C2=Cc3c(cc(Cl)cc3C(=O)O)OC2)cc1)C1CCOCC1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "ad5b35c2-fcbc-481c-b299-432384ef9022",
"task": "sub",
"question": "Please substitute a halo in the molecule COCC(C)CC1CCC(C)C1Sc1cc(C(=O)Nc2cc(F)c(F)c(F)c2)ccc1N(C)C with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCC(C)CC1CCC(C)C1Sc1cc(C(=O)Nc2cc(F)c(F)c(F)c2)ccc1N(C)C",
"ref_smiles": "COCC(C)CC1CCC(C)C1Sc1cc(C(=O)Nc2cc(O)c(F)c(F)c2)ccc1N(C)C",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "f480b87b-f285-4ca6-a128-898edf02c880",
"task": "sub",
"question": "Please substitute a halo in the molecule CN(c1cc(Br)nc(N)n1)C1CCC1 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(c1cc(Br)nc(N)n1)C1CCC1",
"ref_smiles": "CN(c1cc(C#N)nc(N)n1)C1CCC1",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "580e4ab4-7991-446c-adac-c61f5f9c881a",
"task": "sub",
"question": "Please substitute a halo in the molecule CC(C)CCCC(C)NC(=O)C1CCN(S(=O)(=O)c2ccc(F)c(Cl)c2)CC1 with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)CCCC(C)NC(=O)C1CCN(S(=O)(=O)c2ccc(F)c(Cl)c2)CC1",
"ref_smiles": "CC(C)CCCC(C)NC(=O)C1CCN(S(=O)(=O)c2ccc(O)c(Cl)c2)CC1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "80d5469a-cf6c-44d7-8979-c50090a58fad",
"task": "add",
"question": "Modify the molecule CCSCC([NH3+])C(=O)NC(CO)C(=O)NCC(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(C(=O)NC(=O)NC(C(=O)NC(CC(C)C)C(=O)NC(C(=O)NC(C(C)=O)C(C)CC)C(C)SC)C(C)SC)C(C)C by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCSCC([NH3+])C(=O)NC(CO)C(=O)NCC(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(C(=O)NC(=O)NC(C(=O)NC(CC(C)C)C(=O)NC(C(=O)NC(C(C)=O)C(C)CC)C(C)SC)C(C)SC)C(C)C",
"ref_smiles": "CCSCC([NH3+])C(=O)NC(CO)C(=O)NCC(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(C(=O)NC(=O)NC(C(=O)NC(CC(C)C)C(=O)NC(C(=O)NC(C(C)=O)C(C)C(C)c1ccccc1)C(C)SC)C(C)SC)C(C)C",
"add_group": "benzene",
"remove_group": null
},
{
"id": "b5e3b034-5783-493f-a5ce-09ae15b97977",
"task": "sub",
"question": "Modify the molecule CC(C)C([NH2+]C1CC(c2ccc(F)cc2)C1)C(N)=O by substituting a halo with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)C([NH2+]C1CC(c2ccc(F)cc2)C1)C(N)=O",
"ref_smiles": "CC(C)C([NH2+]C1CC(c2ccc(C(=O)O)cc2)C1)C(N)=O",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "ab2cd0ca-81b3-40f8-8ea6-2baa20e0af59",
"task": "add",
"question": "Modify the molecule N#CC1(c2ccc(-c3cn4c(C(F)(F)F)nnc4cn3)cc2)CC1 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "N#CC1(c2ccc(-c3cn4c(C(F)(F)F)nnc4cn3)cc2)CC1",
"ref_smiles": "N#CC1(c2ccc(-c3cn4c(C(F)(F)F)nnc4cn3)cc2)CC1C(=O)O",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "4e9a997a-dfd4-430d-81fb-b0e4b5f5acba",
"task": "add",
"question": "Please add a benzene ring to the molecule O=C(c1ccccc1Cl)N1CCCC(c2[nH+]ccn2CC2CC2)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(c1ccccc1Cl)N1CCCC(c2[nH+]ccn2CC2CC2)C1.",
"ref_smiles": "O=C(c1cccc(-c2ccccc2)c1Cl)N1CCCC(c2[nH+]ccn2CC2CC2)C1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "944a94ba-6ec9-4a3f-9f90-7f72a2933e81",
"task": "add",
"question": "Please add a benzene ring to the molecule O=C(COC(=O)c1cccc(CSc2ccc(Cl)cc2)c1)NC(=O)NC1CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(COC(=O)c1cccc(CSc2ccc(Cl)cc2)c1)NC(=O)NC1CC1.",
"ref_smiles": "O=C(COC(=O)c1cccc(CSc2ccc(Cl)cc2)c1)NC(=O)NC1(c2ccccc2)CC1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "8c860147-250d-4df1-95d7-ac6136cfe875",
"task": "add",
"question": "Modify the molecule COc1ccc(-c2nc(NCc3ccccc3Cl)n(C(=O)c3ccccc3OC)n2)cc1 by adding a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(-c2nc(NCc3ccccc3Cl)n(C(=O)c3ccccc3OC)n2)cc1",
"ref_smiles": "COc1ccccc1C(=O)n1nc(-c2ccc(OCC(=O)O)cc2)nc1NCc1ccccc1Cl",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "1898778a-382e-407b-9f51-6c6868f5f39b",
"task": "add",
"question": "Please add a benzene ring to the molecule COC1CCC2NC(=O)C3SC=CC3C2C1c1ccc(CC[NH3+])cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC1CCC2NC(=O)C3SC=CC3C2C1c1ccc(CC[NH3+])cc1.",
"ref_smiles": "COC1CC(c2ccccc2)C2NC(=O)C3SC=CC3C2C1c1ccc(CC[NH3+])cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "eb53fa20-2dc9-443a-9337-c614f1536d2f",
"task": "sub",
"question": "Please substitute a halo in the molecule CS(=O)(=O)CCNCCOc1ccccc1OC(F)(F)F with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CS(=O)(=O)CCNCCOc1ccccc1OC(F)(F)F",
"ref_smiles": "CS(=O)(=O)CCNCCOc1ccccc1OC(F)(F)C#N",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "29e8e657-843c-451f-9b64-ba123bd5402c",
"task": "sub",
"question": "Modify the molecule CC1(C)CCC(C[NH+]2CCN(c3ccc(C(=O)[O-])c(Oc4cc5cc[nH]c5c(F)c4F)c3)CC2)=C(c2ccc(Cl)cc2)C1 by substituting a halo with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(C)CCC(C[NH+]2CCN(c3ccc(C(=O)[O-])c(Oc4cc5cc[nH]c5c(F)c4F)c3)CC2)=C(c2ccc(Cl)cc2)C1",
"ref_smiles": "CC1(C)CCC(C[NH+]2CCN(c3ccc(C(=O)[O-])c(Oc4cc5cc[nH]c5c(F)c4F)c3)CC2)=C(c2ccc(C=O)cc2)C1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "70c415d4-c484-4954-b011-18f88f40acbb",
"task": "add",
"question": "Please add a nitrile to the molecule O=C([O-])Cn1[nH]cc2c3ccc(Cl)cc3nc-2c1=O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C([O-])Cn1[nH]cc2c3ccc(Cl)cc3nc-2c1=O.",
"ref_smiles": "N#CC(C(=O)[O-])n1[nH]cc2c3ccc(Cl)cc3nc-2c1=O",
"add_group": "nitrile",
"remove_group": null
},
{
"id": "ee0f6412-fd35-4ba7-9d41-b7f9f7d5a38e",
"task": "delete",
"question": "Modify the molecule CC(C)(C)[Si](C)(C)OC1CC(=O)CC(O)C1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)[Si](C)(C)OC1CC(=O)CC(O)C1",
"ref_smiles": "CC(C)(C)[Si](C)(C)OC1CCCC(=O)C1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "86d1c2af-b396-402c-96a5-688b5d942d77",
"task": "delete",
"question": "Please remove a halo from the molecule CCCCCNC(=O)CSc1nc(Cl)cc(N2CCN(C(=O)c3ccccc3F)C(C)C2)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCNC(=O)CSc1nc(Cl)cc(N2CCN(C(=O)c3ccccc3F)C(C)C2)n1.",
"ref_smiles": "CCCCCNC(=O)CSc1nccc(N2CCN(C(=O)c3ccccc3F)C(C)C2)n1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "199cf409-234d-4353-b49d-40036285b529",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1ccc(-c2csc3nc(Cl)nc(N4CCCCC4)c23)cc1 with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(-c2csc3nc(Cl)nc(N4CCCCC4)c23)cc1",
"ref_smiles": "Cc1ccc(-c2csc3nc(O)nc(N4CCCCC4)c23)cc1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "20dd681f-9a87-4f8c-b47e-7f39f2953080",
"task": "sub",
"question": "Please substitute a nitrile in the molecule N#CC1CN(c2c(F)cc(C=CC(=O)[O-])cc2F)CCO1 with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "N#CC1CN(c2c(F)cc(C=CC(=O)[O-])cc2F)CCO1",
"ref_smiles": "O=C([O-])C=Cc1cc(F)c(N2CCOC(S)C2)c(F)c1",
"add_group": "thiol",
"remove_group": "nitrile"
},
{
"id": "f796290b-f149-4f4c-a60f-7cc1df8322c3",
"task": "delete",
"question": "Please remove a halo from the molecule CC1CC=C(Cl)c2c([nH]c[n+]2C)-c2cc(Cl)ccc21.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1CC=C(Cl)c2c([nH]c[n+]2C)-c2cc(Cl)ccc21.",
"ref_smiles": "CC1CC=Cc2c([nH]c[n+]2C)-c2cc(Cl)ccc21",
"add_group": null,
"remove_group": "halo"
},
{
"id": "b8e35ddc-c9bb-47f0-bad7-ce37d93e6f5f",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CC(C)c1ccc(C[NH2+]C(C)C2(C)CC2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)c1ccc(C[NH2+]C(C)C2(C)CC2)cc1.",
"ref_smiles": "CC(C)C[NH2+]C(C)C1(C)CC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "632461c2-5d6b-47b5-a352-a42be038703c",
"task": "sub",
"question": "Modify the molecule C[NH2+]CCC1(c2ccc(Br)cc2)OCCO1 by substituting a halo with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH2+]CCC1(c2ccc(Br)cc2)OCCO1",
"ref_smiles": "CC(=O)c1ccc(C2(CC[NH2+]C)OCCO2)cc1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "72e6f507-f088-4750-a7e9-9a6b55584304",
"task": "delete",
"question": "Please remove a benzene ring from the molecule C[NH+](Cc1ccccc1)Cc1ccc(Cl)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH+](Cc1ccccc1)Cc1ccc(Cl)cc1.",
"ref_smiles": "C[NH+](C)Cc1ccc(Cl)cc1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "2d26ff57-2222-4a16-b120-e981f663b84b",
"task": "add",
"question": "Modify the molecule ClCCc1cnn(-c2ccccc2)c1 by adding a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "ClCCc1cnn(-c2ccccc2)c1",
"ref_smiles": "O=CCc1c(CCCl)cnn1-c1ccccc1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "796dbdd6-8345-416f-8f38-7d4710e11b79",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CNC(=O)CNc1nc2c(c(=O)n(C)c(=O)n2C)n1CC(O)COc1ccccc1C with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CNC(=O)CNc1nc2c(c(=O)n(C)c(=O)n2C)n1CC(O)COc1ccccc1C",
"ref_smiles": "CC(=O)C(COc1ccccc1C)Cn1c(NCC(=O)NC)nc2c1c(=O)n(C)c(=O)n2C",
"add_group": "aldehyde",
"remove_group": "hydroxyl"
},
{
"id": "79daec91-3a61-440b-9d3e-72ac23c9538a",
"task": "sub",
"question": "Modify the molecule O=S1(=O)CCCC(Cl)C1 by substituting a halo with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=S1(=O)CCCC(Cl)C1",
"ref_smiles": "ONC1CCCS(=O)(=O)C1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "d8791e47-cf88-4047-8c62-f374073db0d8",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CCCCCCC(CCCCCC)CCCc1ccc(O)cc1 with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCCC(CCCCCC)CCCc1ccc(O)cc1",
"ref_smiles": "CCCCCCC(CCCCCC)CCCc1ccc(S)cc1",
"add_group": "thiol",
"remove_group": "hydroxyl"
},
{
"id": "557f14c8-5a22-4ca0-851e-d928afbaacfe",
"task": "delete",
"question": "Modify the molecule C[NH2+]C(c1cnn(C)c1)C(C)(C)c1ccccc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C[NH2+]C(c1cnn(C)c1)C(C)(C)c1ccccc1",
"ref_smiles": "C[NH2+]C(c1cnn(C)c1)C(C)C",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "6174717a-bb89-4006-a004-c3617cb18593",
"task": "delete",
"question": "Modify the molecule C=CCN(CCO)C(=O)CNC(=O)c1ccc(C)s1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CCN(CCO)C(=O)CNC(=O)c1ccc(C)s1",
"ref_smiles": "C=CCN(CC)C(=O)CNC(=O)c1ccc(C)s1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "9f197c70-e4bd-426f-a204-2cf040cc6d39",
"task": "delete",
"question": "Modify the molecule CC(C)Oc1cccc(C[NH2+]C(C)(C)C(N)=O)c1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)Oc1cccc(C[NH2+]C(C)(C)C(N)=O)c1",
"ref_smiles": "CC(C)OC[NH2+]C(C)(C)C(N)=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "3fc302af-a6ac-4924-98e0-d661c39afb96",
"task": "add",
"question": "Please add a amine to the molecule CCCCC(OC1CC2CCC(C1)[NH+]2CCCC)c1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCC(OC1CC2CCC(C1)[NH+]2CCCC)c1ccccc1.",
"ref_smiles": "CCCCC(OC1CC2CCC(C1)[NH+]2CCC(C)N)c1ccccc1",
"add_group": "amine",
"remove_group": null
},
{
"id": "32610b74-9ac4-45fd-b775-8db72834a428",
"task": "delete",
"question": "Modify the molecule O=C(C=Cc1cccc(Cl)c1)OCc1cc(=O)oc2ccc3ccccc3c12 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(C=Cc1cccc(Cl)c1)OCc1cc(=O)oc2ccc3ccccc3c12",
"ref_smiles": "O=C(C=CCl)OCc1cc(=O)oc2ccc3ccccc3c12",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "de9c3dc1-5ab4-41b2-9d3b-7846bb7945c3",
"task": "sub",
"question": "Modify the molecule Cc1ccc(C(O)c2ccc(Cl)c(Cl)c2)cc1C by substituting a hydroxyl with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(C(O)c2ccc(Cl)c(Cl)c2)cc1C",
"ref_smiles": "Cc1ccc(C(NO)c2ccc(Cl)c(Cl)c2)cc1C",
"add_group": "nitro",
"remove_group": "hydroxyl"
},
{
"id": "7a7b9e4c-7d9d-4089-afc0-1fa8e7fb1cf6",
"task": "delete",
"question": "Modify the molecule [NH3+]C1C(Cl)=C(C(=O)[O-])N=CC1(Cl)Cl by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "[NH3+]C1C(Cl)=C(C(=O)[O-])N=CC1(Cl)Cl",
"ref_smiles": "[NH3+]C1C=C(C(=O)[O-])N=CC1(Cl)Cl",
"add_group": null,
"remove_group": "halo"
},
{
"id": "f818da98-ce8b-4852-901c-dd276d7f62e7",
"task": "add",
"question": "Modify the molecule CCNC(NC(C)c1ccc(F)cc1F)=[NH+]Cc1csc(CC)n1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCNC(NC(C)c1ccc(F)cc1F)=[NH+]Cc1csc(CC)n1",
"ref_smiles": "CCNC(NC(C)c1ccc(F)cc1F)=[NH+]Cc1nc(CC)sc1O",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "5f9b144b-5ee2-493a-bda9-0c67a22f42e7",
"task": "delete",
"question": "Modify the molecule CCOc1ccc(OCC)c(NC(N)=NCC(c2ccccc2)[NH+]2CCCC2)c1 by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOc1ccc(OCC)c(NC(N)=NCC(c2ccccc2)[NH+]2CCCC2)c1",
"ref_smiles": "CCOc1ccc(OCC)c(C(N)=NCC(c2ccccc2)[NH+]2CCCC2)c1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "0e693464-5be0-45d1-8275-0fdf67ab1b6e",
"task": "add",
"question": "Modify the molecule CNc1nc(C)cc(OCCOc2ccccc2)n1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CNc1nc(C)cc(OCCOc2ccccc2)n1",
"ref_smiles": "CNc1nc(C)cc(OCC(O)Oc2ccccc2)n1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "cc8d5bde-8673-4e21-ae68-745e97f2102c",
"task": "delete",
"question": "Please remove a halo from the molecule COc1ncc(OC(F)(F)F)c(S(=O)(=O)Cl)c1N.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ncc(OC(F)(F)F)c(S(=O)(=O)Cl)c1N.",
"ref_smiles": "COc1ncc(OC(F)(F)F)c([SH](=O)=O)c1N",
"add_group": null,
"remove_group": "halo"
},
{
"id": "d359d051-11f7-41e0-a5c6-7a99be67c1c2",
"task": "delete",
"question": "Please remove a hydroxyl from the molecule O=[N+]([O-])CC(O)c1c[nH+]c(-c2nc3ccccc3n2CCO)[nH]1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=[N+]([O-])CC(O)c1c[nH+]c(-c2nc3ccccc3n2CCO)[nH]1.",
"ref_smiles": "CCn1c(-c2[nH]c(C(O)C[N+](=O)[O-])c[nH+]2)nc2ccccc21",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "e75a16fb-4ad0-463b-9c2a-bd1534499a44",
"task": "delete",
"question": "Modify the molecule CC(=NS(C)(=O)=O)[NH+]=C(Nc1ccccc1)N1CCOCC1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=NS(C)(=O)=O)[NH+]=C(Nc1ccccc1)N1CCOCC1",
"ref_smiles": "CC(=NS(C)(=O)=O)[NH+]=C(N)N1CCOCC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "893aba2f-33e2-4203-8e5d-33c691df843e",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(CCSc1nc2ccccc2c(=O)n1-c1ccccc1)Nc1cc(C(=O)[O-])ccc1Cl with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(CCSc1nc2ccccc2c(=O)n1-c1ccccc1)Nc1cc(C(=O)[O-])ccc1Cl",
"ref_smiles": "N#Cc1ccc(C(=O)[O-])cc1NC(=O)CCSc1nc2ccccc2c(=O)n1-c1ccccc1",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "72fb8233-a3c5-4e4a-b7ff-63d944e1a748",
"task": "sub",
"question": "Please substitute a halo in the molecule CC1(c2ccccc2Cl)NC(=O)N(CC(=O)NC(c2ccccc2)c2cccs2)C1=O with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1(c2ccccc2Cl)NC(=O)N(CC(=O)NC(c2ccccc2)c2cccs2)C1=O",
"ref_smiles": "CC1(c2ccccc2O)NC(=O)N(CC(=O)NC(c2ccccc2)c2cccs2)C1=O",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "45baf0b2-c611-4c77-b4d8-78f2cddac74b",
"task": "add",
"question": "Modify the molecule COCCOCCOC(=O)SC by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCCOCCOC(=O)SC",
"ref_smiles": "COCC(O)OCCOC(=O)SC",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "93dafd0f-e696-4d37-b53d-fd78f1893c0d",
"task": "delete",
"question": "Modify the molecule COC(=O)C(Nc1ccccc1)(c1ccccc1)C1(O)C(=O)N(C)c2ccc([N+](=O)[O-])cc21 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)C(Nc1ccccc1)(c1ccccc1)C1(O)C(=O)N(C)c2ccc([N+](=O)[O-])cc21",
"ref_smiles": "COC(=O)C(Nc1ccccc1)(c1ccccc1)C1C(=O)N(C)c2ccc([N+](=O)[O-])cc21",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "151d410d-3cbc-497d-b2ca-8c9158bb5bac",
"task": "sub",
"question": "Please substitute a halo in the molecule CC(C)NS(=O)(=O)CCCOc1ccc2c(c1)C(C1(c3ccc(Cl)cc3)CCC1)[NH2+]CC2 with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)NS(=O)(=O)CCCOc1ccc2c(c1)C(C1(c3ccc(Cl)cc3)CCC1)[NH2+]CC2",
"ref_smiles": "CC(C)NS(=O)(=O)CCCOc1ccc2c(c1)C(C1(c3ccc(S)cc3)CCC1)[NH2+]CC2",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "36a7bf90-5831-4a95-8f64-db1b69071675",
"task": "add",
"question": "Please add a hydroxyl to the molecule CCCC(O)C1(O)C(O)=C(O)C1O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCC(O)C1(O)C(O)=C(O)C1O.",
"ref_smiles": "CCC(O)C(O)C1(O)C(O)=C(O)C1O",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "92d92657-3963-47ca-a65e-a4084a39f519",
"task": "add",
"question": "Modify the molecule Cn1c(NC(=O)c2cc([N+](=O)[O-])ccc2Cl)nc2ccccc21 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cn1c(NC(=O)c2cc([N+](=O)[O-])ccc2Cl)nc2ccccc21",
"ref_smiles": "Cn1c(NC(=O)c2cc([N+](=O)[O-])ccc2Cl)nc2cccc(-c3ccccc3)c21",
"add_group": "benzene",
"remove_group": null
},
{
"id": "9c49969e-f125-4bed-8be5-7c7383f721e2",
"task": "delete",
"question": "Modify the molecule CCC1(C(=O)[O-])CCC[NH+]1Cc1nnsc1Cl by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC1(C(=O)[O-])CCC[NH+]1Cc1nnsc1Cl",
"ref_smiles": "CCC1(C(=O)[O-])CCC[NH+]1Cc1csnn1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "cdf9887c-7f0f-4ba1-8179-5ba2ba09ff31",
"task": "delete",
"question": "Please remove a halo from the molecule OCC[NH+]1CCN(c2cc(-c3ccc(F)cc3)nc(-c3cccnc3)n2)CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "OCC[NH+]1CCN(c2cc(-c3ccc(F)cc3)nc(-c3cccnc3)n2)CC1.",
"ref_smiles": "OCC[NH+]1CCN(c2cc(-c3ccccc3)nc(-c3cccnc3)n2)CC1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "82de600e-d3ef-42cb-a5c0-d21da404f3a1",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CCc1ccccc1N(CCCC(=O)NCCOc1ccc(C(C)(C)C)cc1)S(C)(=O)=O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1ccccc1N(CCCC(=O)NCCOc1ccc(C(C)(C)C)cc1)S(C)(=O)=O.",
"ref_smiles": "CCN(CCCC(=O)NCCOc1ccc(C(C)(C)C)cc1)S(C)(=O)=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "5bf7e5a5-ac2e-4de3-933d-c471582fd8bc",
"task": "sub",
"question": "Modify the molecule CC(C)C(O)CCNC(=O)c1cccc2cc[nH]c12 by substituting a hydroxyl with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)C(O)CCNC(=O)c1cccc2cc[nH]c12",
"ref_smiles": "CC(C)C(CCNC(=O)c1cccc2cc[nH]c12)C(=O)O",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "124ae598-fa23-4c0a-9c38-8ded1153ff0e",
"task": "add",
"question": "Please add a carboxyl to the molecule COc1ccccc1N1CCN(C(=O)C(=O)Nc2cccc(O)c2)CC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccccc1N1CCN(C(=O)C(=O)Nc2cccc(O)c2)CC1.",
"ref_smiles": "COc1ccc(C(=O)O)cc1N1CCN(C(=O)C(=O)Nc2cccc(O)c2)CC1",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "402b5969-1940-4a8c-9150-0c801b10c956",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(Cn1c(=O)c2cccn2c2ccc(F)cc21)NCCc1ccccc1 with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(Cn1c(=O)c2cccn2c2ccc(F)cc21)NCCc1ccccc1",
"ref_smiles": "O=C(Cn1c(=O)c2cccn2c2ccc(S)cc21)NCCc1ccccc1",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "87f956c0-0cc2-480c-9a22-8dbe5eac90bb",
"task": "sub",
"question": "Please substitute a hydroxyl in the molecule CCC([NH3+])C(CO)N(C)C(C)CC with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC([NH3+])C(CO)N(C)C(C)CC",
"ref_smiles": "CCC([NH3+])C(CC(=O)[OH])N(C)C(C)CC",
"add_group": "carboxyl",
"remove_group": "hydroxyl"
},
{
"id": "1e3cfd3e-ba0d-4c6f-9a12-99013f4ea19f",
"task": "delete",
"question": "Modify the molecule COc1ccc([N+](=O)[O-])cc1CC1CC(c2ccc(OC)c(OC3CCCC3)c2)COC1=O by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc([N+](=O)[O-])cc1CC1CC(c2ccc(OC)c(OC3CCCC3)c2)COC1=O",
"ref_smiles": "COc1ccc([N+](=O)[O-])cc1CC1CC(OC)(OC2CCCC2)COC1=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "9fa02d7c-d7f5-4da1-84b8-96081b2d876a",
"task": "sub",
"question": "Modify the molecule O=C1CC(N(C(=O)CCc2ccc(Cl)s2)C2CC2)C(=O)N1 by substituting a halo with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C1CC(N(C(=O)CCc2ccc(Cl)s2)C2CC2)C(=O)N1",
"ref_smiles": "O=C1CC(N(C(=O)CCc2ccc(O)s2)C2CC2)C(=O)N1",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "9291ca6d-d3e5-40fb-89bd-8a55fe5b999e",
"task": "add",
"question": "Modify the molecule C=CCn1c(CC)nc(-c2ccc(C(C)(C)C)cc2)c1N by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CCn1c(CC)nc(-c2ccc(C(C)(C)C)cc2)c1N",
"ref_smiles": "C=CCn1c(CC)nc(-c2ccc(C(C)(C)C)cc2-c2ccccc2)c1N",
"add_group": "benzene",
"remove_group": null
},
{
"id": "ced16ab2-e501-4b9e-9354-96ed64523b4d",
"task": "delete",
"question": "Modify the molecule CCCC(C)(O)CNC(=O)NC1CCC(C(=O)[O-])CC1 by removing a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCC(C)(O)CNC(=O)NC1CCC(C(=O)[O-])CC1",
"ref_smiles": "CCCC(C)CNC(=O)NC1CCC(C(=O)[O-])CC1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "af0e79e2-a565-44e7-b042-a7fa8057901e",
"task": "add",
"question": "Please add a benzene ring to the molecule CCC#CCCC(=O)OCC.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCC#CCCC(=O)OCC.",
"ref_smiles": "CCC#CCCC(=O)OC(C)c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "18edf2a9-35d8-496b-9bc3-544fc1273174",
"task": "delete",
"question": "Modify the molecule CCCCCCC1CN=C(c2ccccc2)O1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCCCCC1CN=C(c2ccccc2)O1",
"ref_smiles": "CCCCCCC1CN=CO1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "e0d3112f-6000-4d54-b8bf-2b3a4db0d6bf",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CC[NH+](CC)CCN(C(=O)c1ccc(S(=O)(=O)N2CCOCC2)cc1)c1nc2ccc(SC)cc2s1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC[NH+](CC)CCN(C(=O)c1ccc(S(=O)(=O)N2CCOCC2)cc1)c1nc2ccc(SC)cc2s1.",
"ref_smiles": "CC[NH+](CC)CCN(C(=O)S(=O)(=O)N1CCOCC1)c1nc2ccc(SC)cc2s1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "a7aa3c54-d682-4ec8-82c3-0806843c2728",
"task": "add",
"question": "Please add a benzene ring to the molecule COc1ccc(CN(C(=[NH+]C(=O)c2ccnc(Cl)c2)SC)c2ccc(F)c(C(F)(F)F)c2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(CN(C(=[NH+]C(=O)c2ccnc(Cl)c2)SC)c2ccc(F)c(C(F)(F)F)c2)cc1.",
"ref_smiles": "COc1ccc(CN(C(=[NH+]C(=O)c2ccnc(Cl)c2)SC)c2cc(-c3ccccc3)c(F)c(C(F)(F)F)c2)cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "22b673a2-1873-4f61-b07c-78706652408b",
"task": "add",
"question": "Please add a aldehyde to the molecule [NH3+]C1(C(=O)N2CCN(C(=O)c3ccc(C4Nc5ccccc5S4)cc3)CC2)CCC1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "[NH3+]C1(C(=O)N2CCN(C(=O)c3ccc(C4Nc5ccccc5S4)cc3)CC2)CCC1.",
"ref_smiles": "[NH3+]C1(C(=O)N2CCN(C(=O)c3ccc(C4Nc5ccccc5S4)cc3)CC2CC=O)CCC1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "cd24bb3f-2b18-4b97-97de-0d9d9fe2afce",
"task": "delete",
"question": "Please remove a benzene ring from the molecule O=C(CN1C(=O)C2C3CCC(O3)C2C1=O)NC1CCCN(c2ccccc2)C1=O.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(CN1C(=O)C2C3CCC(O3)C2C1=O)NC1CCCN(c2ccccc2)C1=O.",
"ref_smiles": "O=C(CN1C(=O)C2C3CCC(O3)C2C1=O)NC1CCCNC1=O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "9f96ed16-809e-461f-a7d8-068a7d071e5c",
"task": "delete",
"question": "Please remove a hydroxyl from the molecule Cc1ccc(C(=O)N2CCC(O)C(C)(C)C2)o1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(C(=O)N2CCC(O)C(C)(C)C2)o1.",
"ref_smiles": "Cc1ccc(C(=O)N2CCCC(C)(C)C2)o1",
"add_group": null,
"remove_group": "hydroxyl"
},
{
"id": "4154ac71-7926-4fd4-8aad-962a9037f23e",
"task": "delete",
"question": "Modify the molecule O=c1oc2ccccc2c([O-])c1-c1c(-c2ccccc2)[nH]c2c(=O)oc3ccccc3c12 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=c1oc2ccccc2c([O-])c1-c1c(-c2ccccc2)[nH]c2c(=O)oc3ccccc3c12",
"ref_smiles": "O=c1oc2ccccc2c([O-])c1-c1c[nH]c2c(=O)oc3ccccc3c12",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "468136d8-bd6c-45e4-a948-f0e87f4e1b79",
"task": "add",
"question": "Modify the molecule Nc1cccc(C#Cc2cncc(NC(=O)[O-])c2)c1 by adding a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Nc1cccc(C#Cc2cncc(NC(=O)[O-])c2)c1",
"ref_smiles": "Nc1cc(N)cc(C#Cc2cncc(NC(=O)[O-])c2)c1",
"add_group": "amine",
"remove_group": null
},
{
"id": "ee0fbbe6-b595-4496-9180-acc2d5973633",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1sc2nc(COc3ccc(Cl)cc3Cl)nc(N)c2c1C with a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1sc2nc(COc3ccc(Cl)cc3Cl)nc(N)c2c1C",
"ref_smiles": "Cc1sc2nc(COc3ccc(O)cc3Cl)nc(N)c2c1C",
"add_group": "hydroxyl",
"remove_group": "halo"
},
{
"id": "aab939f5-fe92-4e96-b5cf-72977d3b5afe",
"task": "add",
"question": "Please add a hydroxyl to the molecule CC(O)Cc1cc(C[NH3+])c(CC(C)O)c(C[NH3+])c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(O)Cc1cc(C[NH3+])c(CC(C)O)c(C[NH3+])c1.",
"ref_smiles": "CC(O)Cc1c(C[NH3+])cc(CC(O)CO)cc1C[NH3+]",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "bb75ba5f-8c43-4a6c-baaa-3d0e8608a11c",
"task": "sub",
"question": "Please substitute a halo in the molecule CC(C)(C)N1Cc2sc(-c3ccc(S(C)(=O)=O)cc3)c(Br)c2S1(=O)=O with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)(C)N1Cc2sc(-c3ccc(S(C)(=O)=O)cc3)c(Br)c2S1(=O)=O",
"ref_smiles": "CC(C)(C)N1Cc2sc(-c3ccc(S(C)(=O)=O)cc3)c(S)c2S1(=O)=O",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "561997d2-7910-47f3-b679-1edfb96abd76",
"task": "sub",
"question": "Modify the molecule [NH3+]CC(CO)c1nc2ccccc2s1 by substituting a hydroxyl with a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "[NH3+]CC(CO)c1nc2ccccc2s1",
"ref_smiles": "[NH3+]CC(CI)c1nc2ccccc2s1",
"add_group": "halo",
"remove_group": "hydroxyl"
},
{
"id": "1bc8288a-a75d-44a9-89df-357f335c8a01",
"task": "add",
"question": "Modify the molecule Cc1ccc(N(c2ccc(-c3c4ccccc4c(N(c4ccc(C)cc4)C4C=Cc5cc(Br)ccc5C4)c4ccccc34)cc2)c2ccc3cc(C)ccc3c2)cc1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(N(c2ccc(-c3c4ccccc4c(N(c4ccc(C)cc4)C4C=Cc5cc(Br)ccc5C4)c4ccccc34)cc2)c2ccc3cc(C)ccc3c2)cc1",
"ref_smiles": "Cc1ccc(N(c2ccc(-c3c4ccccc4c(N(c4ccc(C)cc4)C4C=Cc5cc(Br)ccc5C4)c4ccccc34)cc2)c2cc3ccc(C)cc3cc2-c2ccccc2)cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "770d5ced-deab-4188-b35d-50bb5233d5f5",
"task": "delete",
"question": "Modify the molecule COC(=O)C(Cc1cccc(C(N)[NH3+])c1)NC(=O)CNS(=O)(=O)c1ccc(C)cc1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC(=O)C(Cc1cccc(C(N)[NH3+])c1)NC(=O)CNS(=O)(=O)c1ccc(C)cc1",
"ref_smiles": "COC(=O)C(CC(N)[NH3+])NC(=O)CNS(=O)(=O)c1ccc(C)cc1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "87e8e6c3-db7d-443e-bb42-7bea8cc9d1ce",
"task": "delete",
"question": "Please remove a benzene ring from the molecule COC1(OC)C(=O)C2=C1C1=C(CCCC1)C1CC(c3ccccc3)(c3ccccc3)C21.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COC1(OC)C(=O)C2=C1C1=C(CCCC1)C1CC(c3ccccc3)(c3ccccc3)C21.",
"ref_smiles": "COC1(OC)C(=O)C2=C1C1=C(CCCC1)C1CC(c3ccccc3)C21",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "9ad5e471-021f-4f94-aa77-e216b681d2c7",
"task": "delete",
"question": "Modify the molecule Brc1cccc(-c2nc3nc4ccccc4nc3n2-c2ccccc2)c1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Brc1cccc(-c2nc3nc4ccccc4nc3n2-c2ccccc2)c1",
"ref_smiles": "Brc1nc2nc3ccccc3nc2n1-c1ccccc1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "273c93a6-9af9-4d84-acd7-c8b325946c8d",
"task": "add",
"question": "Modify the molecule CN(CC(=O)N1CCSCC1c1cnn(C)c1)C1CCS(=O)(=O)C1 by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(CC(=O)N1CCSCC1c1cnn(C)c1)C1CCS(=O)(=O)C1",
"ref_smiles": "CN(CC(=O)N1CCSCC1c1cnn(C)c1)C1CS(=O)(=O)CC1c1ccccc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "8ce722c0-8f95-4ecd-ab51-259980e7f7f7",
"task": "sub",
"question": "Please substitute a halo in the molecule N#Cc1ncn(C(F)F)c1C#N with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "N#Cc1ncn(C(F)F)c1C#N",
"ref_smiles": "N#Cc1ncn(C(F)S)c1C#N",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "fdc3e797-6e3d-4622-9b11-952e4d1f1a81",
"task": "add",
"question": "Modify the molecule Nc1cccc(Nc2[nH]cnc(=O)c2Cl)c1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Nc1cccc(Nc2[nH]cnc(=O)c2Cl)c1",
"ref_smiles": "Nc1cc(Nc2[nH]cnc(=O)c2Cl)ccc1O",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "137c2ffd-72d6-4eee-8821-d8d9cbefeab8",
"task": "add",
"question": "Modify the molecule CN(C(=O)C(Cc1ccccc1)NC(=O)NS(=O)(=O)c1ccccc1-c1cccnc1)c1ccc2c(c1)CCO2 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CN(C(=O)C(Cc1ccccc1)NC(=O)NS(=O)(=O)c1ccccc1-c1cccnc1)c1ccc2c(c1)CCO2",
"ref_smiles": "CN(C(=O)C(Cc1ccccc1)NC(=O)NS(=O)(=O)c1ccccc1-c1cncc(O)c1)c1ccc2c(c1)CCO2",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "2947d5d5-a3e4-4ca6-9877-5a2df5e9ede2",
"task": "delete",
"question": "Modify the molecule O=C(NCCc1ccccc1F)c1cc(COc2ccc3ncccc3c2)on1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NCCc1ccccc1F)c1cc(COc2ccc3ncccc3c2)on1",
"ref_smiles": "O=C(NCCF)c1cc(COc2ccc3ncccc3c2)on1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "f6157466-77b9-41ce-85cf-b1d9d1263371",
"task": "delete",
"question": "Please remove a amine from the molecule CNc1cc(Sc2n[nH]c(=O)n2C)nc(SC)n1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CNc1cc(Sc2n[nH]c(=O)n2C)nc(SC)n1.",
"ref_smiles": "CSc1nc(C)cc(Sc2n[nH]c(=O)n2C)n1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "503534a7-26eb-4b9d-9a1b-31a60060eb7e",
"task": "add",
"question": "Modify the molecule Cn1nc(-c2ccc(C[NH+]3CCC(NC(=O)COc4cccc(Cl)c4)CC3)s2)cc1C(F)(F)F by adding a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cn1nc(-c2ccc(C[NH+]3CCC(NC(=O)COc4cccc(Cl)c4)CC3)s2)cc1C(F)(F)F",
"ref_smiles": "Cn1nc(-c2cc(C#N)c(C[NH+]3CCC(NC(=O)COc4cccc(Cl)c4)CC3)s2)cc1C(F)(F)F",
"add_group": "nitrile",
"remove_group": null
},
{
"id": "4ec4a6da-4e32-478d-a2c6-1fb7bc58b195",
"task": "delete",
"question": "Modify the molecule Cc1ccccc1CC(C)C(=O)N1CCC(c2n[nH]c(=O)o2)CC1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccccc1CC(C)C(=O)N1CCC(c2n[nH]c(=O)o2)CC1",
"ref_smiles": "CCC(C)C(=O)N1CCC(c2n[nH]c(=O)o2)CC1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "e6c494db-2794-40f5-9c96-b0541bc0546f",
"task": "delete",
"question": "Modify the molecule CCc1ccc(C2Cc3ccc(C)c(C)c3N2)s1 by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCc1ccc(C2Cc3ccc(C)c(C)c3N2)s1",
"ref_smiles": "CCc1ccc(C2Cc3ccc(C)c(C)c32)s1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "1f362a3f-9424-4612-9584-54eeddeb3d3c",
"task": "sub",
"question": "Please substitute a halo in the molecule COc1cnc([N+]2=NC(C(F)(F)F)C=C2)c2[nH]cc(C(=O)C(=O)N3CCc4c(cccc4-c4ccccn4)C3)c12 with a nitrile.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1cnc([N+]2=NC(C(F)(F)F)C=C2)c2[nH]cc(C(=O)C(=O)N3CCc4c(cccc4-c4ccccn4)C3)c12",
"ref_smiles": "COc1cnc([N+]2=NC(C(F)(F)C#N)C=C2)c2[nH]cc(C(=O)C(=O)N3CCc4c(cccc4-c4ccccn4)C3)c12",
"add_group": "nitrile",
"remove_group": "halo"
},
{
"id": "8fbb8944-f220-4102-be49-e5b5ceac0b0c",
"task": "add",
"question": "Please add a hydroxyl to the molecule COc1ccccc1C[NH+](C)C(C)C(=O)Nc1cc(S(=O)(=O)N(C)C)ccc1C.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccccc1C[NH+](C)C(C)C(=O)Nc1cc(S(=O)(=O)N(C)C)ccc1C.",
"ref_smiles": "Oc1ccccc1C[NH+](C)C(C)C(=O)Nc1cc(S(=O)(=O)N(C)C)ccc1C",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "310728f2-b304-4476-8337-cc5070ae2022",
"task": "add",
"question": "Modify the molecule C1C[NH+](Cc2nnnn2C2CC2)CC2(CC2)CO1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C1C[NH+](Cc2nnnn2C2CC2)CC2(CC2)CO1",
"ref_smiles": "OC1CC12COCC[NH+](Cc1nnnn1C1CC1)C2",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "c63a2710-5322-4609-9d5d-f91eb878220d",
"task": "delete",
"question": "Modify the molecule CC(=O)N1CCN(C(=O)c2ccoc2Cl)CC1 by removing a halo.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)N1CCN(C(=O)c2ccoc2Cl)CC1",
"ref_smiles": "CC(=O)N1CCN(C(=O)c2ccoc2)CC1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "01f18cb2-1235-45fc-974c-0b3593c796a2",
"task": "sub",
"question": "Modify the molecule CC1COC(c2ccc(Oc3ccc(Cl)cc3)cc2Cl)(C(C)[NH+]2CN=CN2)O1 by substituting a halo with a nitro.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC1COC(c2ccc(Oc3ccc(Cl)cc3)cc2Cl)(C(C)[NH+]2CN=CN2)O1",
"ref_smiles": "CC1COC(c2ccc(Oc3ccc(NO)cc3)cc2Cl)(C(C)[NH+]2CN=CN2)O1",
"add_group": "nitro",
"remove_group": "halo"
},
{
"id": "ea429b2a-101b-4479-8614-b4136091388f",
"task": "delete",
"question": "Please remove a amine from the molecule CCOP(=O)(OCC)C1C=CCNN1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOP(=O)(OCC)C1C=CCNN1.",
"ref_smiles": "CCOP(=O)(OCC)C1C=CCN1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "7c90ab4c-7bec-4f4b-b5b1-305f1d81bd8f",
"task": "sub",
"question": "Please substitute a halo in the molecule O=C(NN=Cc1cc(Br)c(OCc2ccc(Cl)cc2Cl)c(Br)c1)c1ccc(F)cc1 with a carboxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=C(NN=Cc1cc(Br)c(OCc2ccc(Cl)cc2Cl)c(Br)c1)c1ccc(F)cc1",
"ref_smiles": "O=C(NN=Cc1cc(Br)c(OCc2ccc(Cl)cc2Cl)c(C(=O)[OH])c1)c1ccc(F)cc1",
"add_group": "carboxyl",
"remove_group": "halo"
},
{
"id": "93431b1d-cc2d-4ef0-9e66-d7d7fba12603",
"task": "delete",
"question": "Please remove a benzene ring from the molecule CCNC(=O)C1(Cc2ccccc2-c2ccccc2)CCN(C(=O)C2NNC(CC)C2C)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCNC(=O)C1(Cc2ccccc2-c2ccccc2)CCN(C(=O)C2NNC(CC)C2C)C1.",
"ref_smiles": "CCNC(=O)C1(Cc2ccccc2)CCN(C(=O)C2NNC(CC)C2C)C1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "ccb85d45-f283-42c6-9e51-2de7624b6640",
"task": "add",
"question": "Please add a benzene ring to the molecule COc1ccc(C(=C[NH+](C)C)C(=O)c2ccc(OC)cc2OB(F)F)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(C(=C[NH+](C)C)C(=O)c2ccc(OC)cc2OB(F)F)cc1.",
"ref_smiles": "COc1ccc(C(=C[NH+](C)C)C(=O)c2ccc(OC)c(-c3ccccc3)c2OB(F)F)cc1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "773ff13e-4bdb-49d4-841c-6acc7266785d",
"task": "sub",
"question": "Modify the molecule CCCN(Cc1ccccc1)C(=O)Nc1ccc(Cl)c(F)c1 by substituting a halo with a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCCN(Cc1ccccc1)C(=O)Nc1ccc(Cl)c(F)c1",
"ref_smiles": "CCCN(Cc1ccccc1)C(=O)Nc1ccc(S)c(F)c1",
"add_group": "thiol",
"remove_group": "halo"
},
{
"id": "c9d2df1d-c413-4d8d-a22e-b926425b538d",
"task": "delete",
"question": "Please remove a benzene ring from the molecule C=CCc1cc(C=NCCCCCC)c(O)c(-c2ccc(O)c(CC=C)c2)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "C=CCc1cc(C=NCCCCCC)c(O)c(-c2ccc(O)c(CC=C)c2)c1.",
"ref_smiles": "C=CCc1cc(C(C=C)C(O)=NCCCCCC)ccc1O",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "833df3e9-06a6-4029-af78-653f023803de",
"task": "delete",
"question": "Modify the molecule CC(=O)Nc1ccc(C2=C(Nc3ccc(OC(C)C)cc3)C(=O)N(CCOC(C)C)C2=O)cc1 by removing a amine.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(=O)Nc1ccc(C2=C(Nc3ccc(OC(C)C)cc3)C(=O)N(CCOC(C)C)C2=O)cc1",
"ref_smiles": "CC(=O)Nc1ccc(C2=C(c3ccc(OC(C)C)cc3)C(=O)N(CCOC(C)C)C2=O)cc1",
"add_group": null,
"remove_group": "amine"
},
{
"id": "b6ce9040-f439-475f-892f-36f0a166c5fb",
"task": "add",
"question": "Modify the molecule Cc1cnn(CCNC(=O)CC[NH3+])c1 by adding a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1cnn(CCNC(=O)CC[NH3+])c1",
"ref_smiles": "[NH3+]CCC(=O)NCCn1cc(CCC=O)cn1",
"add_group": "aldehyde",
"remove_group": null
},
{
"id": "096118dc-cd31-42ea-9d9c-c6f5d94bca94",
"task": "add",
"question": "Please add a benzene ring to the molecule O=S(=O)(Nc1cccc(F)c1F)c1ccc(Br)c(Cl)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=S(=O)(Nc1cccc(F)c1F)c1ccc(Br)c(Cl)c1.",
"ref_smiles": "O=S(=O)(Nc1cccc(F)c1F)c1cc(Cl)c(Br)c(-c2ccccc2)c1",
"add_group": "benzene",
"remove_group": null
},
{
"id": "be5290b1-34f8-44a3-8bd0-6551274f6cfa",
"task": "add",
"question": "Modify the molecule CCNC(C#N)c1ccccc1COC by adding a thiol.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCNC(C#N)c1ccccc1COC",
"ref_smiles": "CCNC(C#N)c1ccc(S)cc1COC",
"add_group": "thiol",
"remove_group": null
},
{
"id": "588cf2ca-c5c9-4782-91f0-a5f534fba558",
"task": "sub",
"question": "Please substitute a halo in the molecule Cc1ccc(-c2cnc(Br)cc2Cl)cc1 with a aldehyde.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccc(-c2cnc(Br)cc2Cl)cc1",
"ref_smiles": "CC(=O)c1cc(Cl)c(-c2ccc(C)cc2)cn1",
"add_group": "aldehyde",
"remove_group": "halo"
},
{
"id": "4cb50abb-bfd2-4dde-a1f5-ff4d29132721",
"task": "add",
"question": "Please add a hydroxyl to the molecule O=[N+]([O-])c1ccccc1N=c1scc(-c2cc3ccccc3o2)n1N=Cc1ccc(-c2ccccc2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=[N+]([O-])c1ccccc1N=c1scc(-c2cc3ccccc3o2)n1N=Cc1ccc(-c2ccccc2)cc1.",
"ref_smiles": "O=[N+]([O-])c1c(O)cccc1N=c1scc(-c2cc3ccccc3o2)n1N=Cc1ccc(-c2ccccc2)cc1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "4bb12e7d-d302-446c-b577-19211714588f",
"task": "add",
"question": "Please add a hydroxyl to the molecule CC(C)C(CC(=O)C1(O[Si](C)(C)C)CC2CCC1(C)C2(C)C)NC(=O)OCc1ccccc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CC(C)C(CC(=O)C1(O[Si](C)(C)C)CC2CCC1(C)C2(C)C)NC(=O)OCc1ccccc1.",
"ref_smiles": "CC(C)C(CC(=O)C1(O[Si](C)(C)C)CC2CCC1(C)C2(C)C)NC(=O)OCc1cccc(O)c1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "3a2a0a7b-8672-4d8e-8d54-2b156e861a25",
"task": "add",
"question": "Please add a carboxyl to the molecule COc1ccc(S(=O)(=O)NS(=O)(=O)c2ccc(OC)cc2)cc1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccc(S(=O)(=O)NS(=O)(=O)c2ccc(OC)cc2)cc1.",
"ref_smiles": "COc1ccc(S(=O)(=O)NS(=O)(=O)c2ccc(OC)c(C(=O)O)c2)cc1",
"add_group": "carboxyl",
"remove_group": null
},
{
"id": "7a6fbeba-0cca-4781-bdd5-641530785df2",
"task": "delete",
"question": "Please remove a halo from the molecule CCOC(=O)c1cnn(Cc2cc(Br)ccc2F)c1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "CCOC(=O)c1cnn(Cc2cc(Br)ccc2F)c1.",
"ref_smiles": "CCOC(=O)c1cnn(Cc2ccccc2F)c1",
"add_group": null,
"remove_group": "halo"
},
{
"id": "3ffe439f-99b0-4cc7-9668-d5b4d74bf817",
"task": "delete",
"question": "Modify the molecule COc1ccccc1CC(=O)OCC(=O)Nc1cccc(C(C)C)c1 by removing a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COc1ccccc1CC(=O)OCC(=O)Nc1cccc(C(C)C)c1",
"ref_smiles": "COc1ccccc1CC(=O)OCC(=O)NC(C)C",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "268baf80-d860-4796-acf0-ddb55ee4f631",
"task": "delete",
"question": "Please remove a benzene ring from the molecule O=S1(=O)CCC(CNC(NC2CCOCC2)=[NH+]Cc2cccc(Cl)c2)C1.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "O=S1(=O)CCC(CNC(NC2CCOCC2)=[NH+]Cc2cccc(Cl)c2)C1.",
"ref_smiles": "O=S1(=O)CCC(CNC(NC2CCOCC2)=[NH+]CCl)C1",
"add_group": null,
"remove_group": "benzene"
},
{
"id": "43850857-7b74-4f2b-85f2-14a99d6bbf02",
"task": "add",
"question": "Modify the molecule Cc1ccccc1C(C(=O)[O-])[NH+](C)Cc1cc(-c2ccncc2)no1 by adding a hydroxyl.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "Cc1ccccc1C(C(=O)[O-])[NH+](C)Cc1cc(-c2ccncc2)no1",
"ref_smiles": "Cc1ccccc1C(C(=O)[O-])[NH+](CO)Cc1cc(-c2ccncc2)no1",
"add_group": "hydroxyl",
"remove_group": null
},
{
"id": "9c69fb12-48ee-4956-a33e-4a5aeb46d962",
"task": "add",
"question": "Modify the molecule COCC([NH3+])CN(C)C(=O)Cc1ccccc1F by adding a benzene ring.\nPlease wrap the final SMILES in <smiles>...</smiles>.",
"src_smiles": "COCC([NH3+])CN(C)C(=O)Cc1ccccc1F",
"ref_smiles": "COCC([NH3+])CN(C)C(=O)Cc1ccc(-c2ccccc2)cc1F",
"add_group": "benzene",
"remove_group": null
}
]