Input: The molecule is a member of the class of benzophenones that is benzophenone in which one of the phenyl groups is substituted by a 3,3-dimethylallyl group at position 3 and by hydroxy groups at positions 2 and 6, while the other is substituted by a formyl group at position 2, a 3,3-dimethylallyloxy group at position 3, a methyl group at position 4, and a hydroxy group at position 6. It is an aldehyde, a member of phenols, a member of benzophenones, a member of resorcinols and an arugosin A. It is a tautomer of an arugosin A (lactol form).

Output: CC(C)=CCOC1=C(C)C=C(O)C(C(=O)C2=C(O)C=CC(CC=C(C)C)=C2O)=C1C=O


Input: The molecule is a dipeptide composed of glycine and L-histidine joined by a peptide linkage. It has a role as a metabolite. It derives from a glycine and a L-histidine.

Output: NCC(=O)N[C@@H](CC1=CN=CN1)C(=O)O


Input: The molecule is a medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of decanoic acid. It has a role as an Escherichia coli metabolite and a mouse metabolite. It derives from a decanoic acid and a coenzyme A. It is a conjugate acid of a decanoyl-CoA(4-).

Output: CCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)(O)O


Input: The molecule is a 2-oxo monocarboxylic acid anion that is the conjugate base of 2-oxopentanoic acid, obtained by deprotonation of the carboxy group. It is a 2-oxo monocarboxylic acid anion and a member of oxopentanoates. It is functionally related to a valerate. It is a conjugate base of a 2-oxopentanoic acid.

Output: CCCC(=O)C(=O)[O-]


Input: The molecule is a quaternary ammonium compound that blocks presynaptic potassium channels, and subsequently prolongs the action potential and increases presynaptic calcium concentrations. It was first discovered in Scotland in the 1970s and its clinical effectiveness for neuromuscular disorders, including Lambert–Eaton myasthenic syndrome (LEMS), has been investigated in the 1980s. Amifampridine phosphate is a more stable salt that serves as an active ingredient of EMA-approved Firdapse, which was previously marketed as Zenas. It is currently used as the first-line symptomatic treatment for LEMS in adult patients and is ideally given as oral tablets in divided doses, three or four times a day. Firdapse (amifampridine) was formally approved by the US FDA for the treatment of adults with LEMS as recently as November of 2018.  LEMS is a rare auto-immune disorder of the neuromuscular junction that is characterized by proximal muscle weakness, depressed tendon reflexes, and posttetanic potentiation in addition to autonomic dysfunction. About 50-60% of the patients develop more rapidly progressive LEMS and small cell lung cancer, which influences the prognosis. Patients with LEMS develop serum antibodies against presynaptic P/Q-type voltage-gated calcium channels, leading to decreased presynaptic calcium levels and reduced quantal release of acetylcholine, which is mainly responsible for causing symptoms of LEMS. Reduced acetylcholine release at the neuromuscular junction leads to decreased frequency of miniature endplate potentials of normal amplitude, and insufficient acetylcholine levels for the activation of postsynaptic muscle fibers following a single nerve impulse. This leads to the reduction of the compound muscle action potential (CMAP). Treatment for LEMS include immunotherapy such as conventional immunosuppression or intravenous immunoglobulins, however such treatments are recommended in patients in whom symptomatic treatment would not suffice. Amifampridine is the nonimmune treatment options for LEMS.   In phase III clinical trials of adult patients with LEMS, treatment of amifampridine significantly improved symptoms of LEMS compared to placebo with good tolerance. It was demonstrated in clinical studies involving healthy volunteers that the pharmacokinetics and systemic exposure to amifampridine is affected by the genetic differences in N-acetyl-transferase (NAT) enzymes (acetylator phenotype) and NAT2 genotype, which is subject to genetic variation. Slow acetylators were at higher risk for experiencing drug-associated adverse reactions, such as paresthesias, nausea, and headache.

Output: NC1=CC=NC=C1N


Input: The molecule is an organic cation obtained by protonation of the imidazole groups of daclatasvir. It is a conjugate acid of a daclatasvir.

Output: COC(=O)N[C@H](C(=O)N1CCC[C@H]1C1=NC=C(C2=CC=C(C3=CC=C(C4=CN=C([C@@H]5CCCN5C(=O)[C@@H](NC(=O)OC)C(C)C)N4)C=C3)C=C2)N1)C(C)C;[H+];[H+]


Input: The molecule is a monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position. It has a role as a non-narcotic analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a xenobiotic, an environmental contaminant, a drug allergen and a non-steroidal anti-inflammatory drug. It is a secondary amino compound, an amino acid, a dichlorobenzene, an aromatic amine and a monocarboxylic acid. It derives from a phenylacetic acid and a diphenylamine. It is a conjugate acid of a diclofenac(1-).

Output: O=C(O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl


Input: The molecule is a monocarboxylic acid anion that is the conjugate base of 5,6-epoxyretinoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3. It is a monocarboxylic acid anion and a retinoid anion. It is a conjugate base of a 5,6-epoxyretinoic acid.

Output: CC(/C=C/C12OC1(C)CCCC2(C)C)=C\C=C\C(C)=C\C(=O)[O-]


Input: The molecule is a pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks. It has a role as an EC 5.99.1.2 (DNA topoisomerase) inhibitor and an antineoplastic agent.

Output: CC[C@@]1(O)C(=O)OCC2=C1C=C1C3=NC4=CC=C(O)C(CN(C)C)=C4C=C3CN1C2=O


Input: The molecule is an RNA fragment comprised of three guanosine, two adenosine and four cytidine residues connected by 3'->5' phosphodiester linkages in the sequence G-A-G-A-G-A-C-C-C-A-C.


Input: The molecule is a fatty acid-taurine conjugate derived from arachidonic acid. It has a role as a mouse metabolite. It is functionally related to an arachidonic acid. It is a conjugate acid of a N-arachidonoyltaurine(1-).

Output: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCS(=O)(=O)O


Input: The molecule is a manufactured chemical that does not occur naturally. It is an odorless and oily liquid that is colorless to faint yellow in color. It is slightly soluble in water and does not evaporate easily. Di-n-phtalate is used to make plastics more flexible and is also in carpet backings, paints, glue, insect repellents, hair spray, nail polish, and rocket fuel.

Output: CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC


Input: The molecule is a long-chain fatty acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate OH groups of (R)-2-hydroxyhexadecanoyl-CoA; major species at pH 7.3. It is a conjugate base of a (R)-2-hydroxyhexadecanoyl-CoA.

Output: CCCCCCCCCCCCCC[C@@H](O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]


Input: The molecule is a Rho Kinase Inhibitor. The mechanism of action of it is as a Rho Kinase Inhibitor.

Output: CC1=CC=C(C(=O)OCC2=CC=C([C@@H](CN)C(=O)NC3=CC=C4C=NC=CC4=C3)C=C2)C(C)=C1


Input: The molecule is a 3-hydroxy fatty acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of (3R,7Z,10Z,13Z,16Z)-3-hydroxydocosatetraenoyl-CoA; major species at pH 7.3. It is a (R)-3-hydroxyacyl-CoA(4-), a 3-hydroxy fatty acyl-CoA(4-) and a long-chain fatty acyl-CoA(4-). It is a conjugate base of a (3R,7Z,10Z,13Z,16Z)-3-hydroxydocosatetraenoyl-CoA.

Output: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCC[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]


Input: The molecule is a mineral with formula of Cr. The corresponding IMA (International Mineralogical Association) number is IMA1980-094. The IMA symbol is Cr.

Output: [Cr]


Input: The molecule is the active ingredient in weed killer products such as RoundUp™. Glyphosate products are one of the most widely used weed killers worldwide in farms and in home gardens and lawns. These products typically contain glyphosate in combination with other ingredients that help improve the absorption of the glyphosate into the plant. Glyphosate-based formulations (GBFs) are easily bought in most stores. These products can have different combinations of other ingredients or different concentrations of glyphosate.

Output: O=C(O)CNCP(=O)(O)O


Input: The molecule appears as a colorless liquid with a disagreeable odor. Slightly less dense than water. Irritates skin and eyes. Used to make paints and pharmaceuticals.

Output: C=C1CC(=O)O1


Input:
The molecule is used on soya beans, citrus, tea, vegetables and mushrooms. Also used as an insecticide in feed for poultry and pigs and as a controlled release bolus in cattle

Diflubenzuron belongs to the family of N-Phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of an urea group.

Output: O=C(NC(=O)C1=C(F)C=CC=C1F)NC1=CC=C(Cl)C=C1


Input: The molecule is an organic heterotricyclic compound found in Hypericum chinense. It has a role as a plant metabolite. It is a member of benzodioxoles, an organic heterotricyclic compound, a member of phenols, a monomethoxybenzene and an aromatic ketone.

Output: COC1=C(C)C(O)=C(C(=O)CC(C)C)C2=C1C[C@H]1C[C@@H](C3=CC=C4OCOC4=C3)OC1(C1=CC=C3OCOC3=C1)O2


Input: The molecule is an N-acyl-4-hydroxy-15-methylhexadecasphinganine-1-phosphocholine in which the acyl group has 21 carbons and 0 double bonds and is 2-hydroxylated. It is functionally related to a 15-methylhexadecaphytosphingosine.

Output: CCCCCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)[C@H](O)[C@H](O)CCCCCCCCCCC(C)C


Input: The molecule is an intermediate in heme synthesis. This is the first compound in the porphyrin synthesis pathway. It is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway. Aminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.

Output: NCC(=O)CCC(=O)O


Input: The molecule is a beta-adrenoceptor agonist with potential antidepressant activity. Even though preferentially interacts with beta-adrenergic receptors, flerobuterol may exhibit antidepressant activity. Sustained administration of flerobuterol, similar to other beta-adrenergic agonists, may increase serotonin (5-HT) synthesis, thereby enhance serotonergic neurotransmission, partially through an increased transport of the serotonin precursor (tryptophan) to brain.

Output: CC(C)(C)NCC(O)C1=CC=CC=C1F


Input: The molecule is a fourth-generation cephalosporin antibiotic having (4-carbamoyl-1-azoniabicyclo[2.2.2]octan-1-yl)methyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively. It is a cephalosporin and a member of thiadiazoles.

Output: CO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(C[N+]34CCC(C(N)=O)(CC3)CC4)CS[C@H]12)C1=NSC(N)=N1


Input: The molecule is a sedoheptulose derivative and a ketoheptose phosphate. It has a role as an Escherichia coli metabolite and a mouse metabolite. It derives from a sedoheptulose. It is a conjugate acid of a sedoheptulose 1,7-bisphosphate(4-).

Output: O=C(COP(=O)(O)O)[C@@H](O)[C@H](O)[C@H](O)[C@H](O)COP(=O)(O)O


Input: The molecule is a drug that has been approved by the U.S. Food and Drug Administration (FDA) under the brand name Istodax for the treatment of a certain type of cancer. Romidepsin is also being studied as an investigational drug as part of a strategy to cure HIV infection.As an HIV investigational drug, romidepsin belongs to a group of drugs called latency-reversing agents.

Output: CC=C1NC(=O)C2CSSCCC=CC(CC(=O)NC(C(C)C)C(=O)N2)OC(=O)C(C(C)C)NC1=O


Input: The molecule is a 3-sn-phosphatidyl L-serine in which the phosphatidyl acyl groups are both oleoyl. It has a role as a mouse metabolite. It is functionally related to an oleic acid. It is a conjugate acid of a 1,2-dioleoyl-sn-glycero-3-phospho-L-serine(1-).

Output: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](N)C(=O)O)OC(=O)CCCCCCC/C=C\CCCCCCCC


Input: The molecule is an apo carotenoid sesquiterpenoid and an alpha,beta-unsaturated monocarboxylic acid. It has a role as a metabolite. It is a conjugate acid of a phaseic acid anion.

Output: CC(=C/C(=O)O)/C=C/[C@]1(O)[C@@]2(C)CO[C@]1(C)CC(=O)C2


Input: The molecule is an acyclic diterpene glycoside consisting of a 20-hydroxygeranyllinalool skeleton conjugated to a malonylglucosyl residue at C-20 and a rhamnosyl(malonyl)glucosyl moiety at C-3. It has a role as a metabolite. It is a disaccharide derivative and a diterpene glycoside. It is functionally related to a lyciumoside IV.

Output: C=C[C@](C)(CC/C=C(\C)CC/C=C(\C)CC/C=C(/C)CO[C@@H]1O[C@H](COC(=O)CC(=O)O)[C@@H](O)[C@H](O)[C@H]1O)O[C@@H]1O[C@H](COC(=O)CC(=O)O)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H]1O


Input: The molecule is a 2-(2-hydroxyacyl)sphingosine in which the ceramide N-acyl group is specified as 2-hydroxystearoyl. It is functionally related to a 2-hydroxyoctadecanoic acid.

Output: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)NC(=O)C(O)CCCCCCCCCCCCCCCC


Input: The molecule is a phthalic acid monoester obtained by formal condensation of one of the carboxy groups of phthalic acid with the hydroxy group of isononanol. It has a role as a human xenobiotic metabolite.

Output: CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)O


Input: The molecule is the organophosphate oxoanion that at pH 7.3 is the major microspecies formed from undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-isoglutaminyl-(glycyl)-L-lysyl-D-alanyl-D-alanine, formed by loss of two protons from the diphospho group. It is a conjugate base of an undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-isoglutaminyl-(glycyl)-L-lysyl-D-alanyl-D-alanine.


Input: The molecule is a diacylglycerol 40:0 in which the acyl groups at positions 1 and 2 are octadecanoyl and docosanoyl respectively. It is a diacylglycerol 40:0 and a 1,2-diacyl-sn-glycerol. It is functionally related to an octadecanoic acid and a docosanoic acid.

Output: CCCCCCCCCCCCCCCCCCCCCC(=O)O[C@@H](CO)COC(=O)CCCCCCCCCCCCCCCCC


Input: The molecule is an organochlorine compound that is the 3'-hydroxylated metabolite of diclofenac. It has a role as a drug metabolite and an allergen. It is a dichlorobenzene, a monocarboxylic acid, a member of phenols and a secondary amino compound. It derives from a diclofenac.

Output: O=C(O)CC1=CC=CC=C1NC1=C(Cl)C=CC(O)=C1Cl


Input: The molecule is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).

Output: O=C(O)C1=CC=CC=C1


Input: The molecule is a water soluble, orally bioavailable inhibitor of the serine/threonine protein kinase Akt (protein kinase B) and extracellular signal-regulated kinase (ERK), with potential antineoplastic activity. Upon administration, Akt/ERK inhibitor ONC201 binds to and inhibits the activity of Akt and ERK, which may result in inhibition of the phosphatidylinositol 3-kinase (PI3K)/Akt signal transduction pathway as well as the mitogen-activated protein kinase (MAPK)/ERK-mediated pathway. This may lead to the induction of tumor cell apoptosis mediated by tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL)/TRAIL death receptor type 5 (DR5) signaling in AKT/ERK-overexpressing tumor cells. The PI3K/Akt signaling pathway and MAPK/ERK pathway are upregulated in a variety of tumor cell types and play a key role in tumor cell proliferation, differentiation and survival by inhibiting apoptosis. In addition, ONC201 is able to cross the blood-brain barrier.

Output: CC1=CC=CC=C1CN1C(=O)C2=C(CCN(CC3=CC=CC=C3)C2)N2CCN=C12


Input: The molecule is a non-proteinogenic alpha-amino acid that is homocysteine in which the thiol group has benn oxidised to the corresponding sulfonic acid. It is an amino sulfonic acid, a carboxyalkanesulfonic acid and a non-proteinogenic alpha-amino acid. It is functionally related to a homocysteine.

Output: NC(CCS(=O)(=O)O)C(=O)O


Input: The molecule is an orally available cancer cell stemness kinase inhibitor with potential antineoplastic activity. Even though the exact target has not been fully elucidated, amcasertib targets and inhibits one or more pathways involved in cancer stem cell survival. As a result, cancer stem cell (CSC) growth as well as heterogeneous cancer cell growth is inhibited. CSCs, self-replicating cells able to differentiate into heterogeneous cancer cells, appear to be responsible for both tumor relapse and metastasis.

Output: CCN(CC)CCNC(=O)C1=C(C)NC(/C=C2\C(=O)NC3=CC=C(C4=CSC(C5=CC=CC=C5)=N4)C=C23)=C1C


Input: The molecule is the (S)-enantiomer of dihydrolipoic acid. It is an enantiomer of a (R)-dihydrolipoic acid.

Output: O=C(O)CCCC[C@H](S)CCS


Input: The molecule is an N-acetyl-beta-D-glucosaminide in which the anomeric hydroxy hydrogen is replaced by a 2-nitrophenyl group. It has a role as a chromogenic compound. It is a C-nitro compound and a N-acetyl-beta-D-glucosaminide. It derives from a 2-nitrophenol.

Output: CC(=O)N[C@H]1[C@H](OC2=CC=CC=C2[N+](=O)[O-])O[C@H](CO)[C@@H](O)[C@@H]1O


Input: The molecule is a diacylglycerol 40:0 in which the acyl groups at positions 1 and 2 are octadecanoyl and docosanoyl respectively. It is a diacylglycerol 40:0 and a 1,2-diacyl-sn-glycerol. It derives from an octadecanoic acid and a docosanoic acid.

Output: CCCCCCCCCCCCCCCCCCCCCC(=O)O[C@@H](CO)COC(=O)CCCCCCCCCCCCCCCCC


Input: The molecule is a maltose phosphate having the phosphate group placed at the 6'-position. It has a role as an Escherichia coli metabolite. It is functionally related to a maltose. It is a conjugate acid of an alpha-maltose 6'-phosphate(2-).

Output: O=P(O)(O)OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O


Input: The molecule is a 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose. It is functionally related to an alpha-D-glucosamine.

Output: C[C@@H](O[C@@H]1[C@@H](N)[C@@H](O)O[C@H](CO)[C@H]1O)C(=O)O


Input: The molecule is a phosphatidylinositol 28:0 in which the phosphatidyl acyl groups at positions 1 and 2 are specified as palmitoyl (hexadecanoyl) and lauroyl (dodecanoyl) respectively. It is a phosphatidylinositol 28:0(1-) and a 1-hexadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol(1-). It is a conjugate base of a 1-palmitoyl-2-lauroyl-sn-glycero-3-phospho-1D-myo-inositol.

Output: CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OC1[C@H](O)[C@H](O)C(O)[C@H](O)[C@H]1O)OC(=O)CCCCCCCCCCC


Input: The molecule is a benzochromenone that is 6H-dibenzo[b,d]pyran substituted by an oxo group at position 6. It has a role as a plant metabolite.


Input: The molecule is a nucleotide-sugar oxoanion arising from deprotonation of the free diphosphate OH groups of dTDP-4-dehydro-6-deoxy-beta-D-gulose. It is a conjugate base of a dTDP-4-dehydro-6-deoxy-beta-D-gulose.

Output: CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)([O-])OP(=O)([O-])O[C@@H]3O[C@H](C)C(=O)[C@@H](O)[C@H]3O)O2)C(=O)NC1=O


Input: The molecule is an arsenic oxoanion obtained deprotonation of both arsenite OH groups of methylarsonous acid. It is functionally related to an arsonite(2-). It is a conjugate base of a methylarsonous acid.

Output: C[As]([O-])[O-]


Input: The molecule is a 1,2-diacyl-sn-glycerol in which both acyl groups are specified as linoleoyl. It has a role as a mouse metabolite. It is a 1,2-diacyl-sn-glycerol and a dilinoleoylglycerol. It derives from a linoleic acid. It is an enantiomer of a 2,3-dilinoleoyl-sn-glycerol.

Output: CCCCC/C=C\C/C=C\CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC


Input: The molecule is a 1D-myo-inositol bis(diphosphate) tetrakisphosphate having the two diphospho groups located at positions 1 and 3. It derives from a myo-inositol.

Output: O=P(O)(O)OC1[C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)C(OP(=O)(O)O)[C@H](OP(=O)(O)OP(=O)(O)O)[C@H]1OP(=O)(O)O


Input: The molecule is an organic cation that is the conjugate acid of novapikromycin, obtained by protonation of the tertiary amino group; major species at pH 7.3. It is an ammonium ion derivative and an organic cation. It is a conjugate acid of a novapikromycin.

Output: C[C@H]1C(=O)O[C@H]([C@@H](C)O)[C@@](C)(O)/C=C/C(=O)[C@H](C)C[C@H](C)[C@H](O[C@@H]2O[C@H](C)C[C@H]([NH+](C)C)[C@H]2O)[C@@H](C)C1=O


Input: The molecule is the isomeric form of melphalan, with alkylating activity. Sarcolysin crosslinks DNA, thereby causing an inhibition in DNA replication and eventually a reduction in cellular proliferation.

Output: NC(CC1=CC=C(N(CCCl)CCCl)C=C1)C(=O)O


Input: The molecule is conjugate base of 15-dehydro-prostaglandin D2. It is a conjugate base of a 15-dehydro-prostaglandin D2.

Output: CCCCCC(=O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)[O-]


Input: The molecule is an epoxy(hydroxy)icosatrienoic acid that is (5Z,8Z,14Z)-icosatrienoic acid having the epoxide group across positions 11-12 and the hydroxy substituent located at position 20. It is an epoxy(hydroxy)icosatrienoic acid and an omega-hydroxy-long-chain fatty acid. It is functionally related to an arachidonic acid. It is a conjugate acid of an 11,12-epoxy-20-hydroxy-(5Z,8Z,14Z)-icosatrienoate.

Output: O=C(O)CCC/C=C\C/C=C\CC1OC1C/C=C\CCCCCO


Input: The molecule is a 1-acyl-2-oleoyl-sn-glycero-3-phosphate(2-) in which the 1-acyl substituent is specified as arachidonoyl. It is functionally related to an oleic acid and an arachidonic acid. It is a conjugate acid of a 1-arachidonoyl-2-oleoyl-sn-glycero-3-phosphate(2-).

Output: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OC[C@H](COP(=O)(O)O)OC(=O)CCCCCCC/C=C\CCCCCCCC


Input: The molecule is the monoazo compound formed from arsanilic acid. It is used as an immunologic research tool. It has a role as a hapten and an allergen. It is a monoazo compound and an organoarsonic acid. It derives from an arsanilic acid.

Output: O=[As](O)(O)C1=CC=C(N=NC2=CC=C([As](=O)(O)O)C=C2)C=C1


Input: The molecule is an organonitrogen compound and an organooxygen compound. It is functionally related to a beta-amino acid.

Output: O=C(O)CCNC(=O)C1=CC=CC=C1


Input: The molecule is the acid form of sodium selenite, a form of selenium.  Selenium is an essential trace element and antioxidant. It is a cofactor metabolic enzyme regulation. It also plays an important role in maintaining the general health of tissue and muscle and has antioxidant properties. Selenium is a component of glutathione peroxidase enzyme, which protects cell components from oxidative damage due to peroxides produced during cellular metabolism.  Selenium (Se) has been demonstrated to prevent cancer in numerous animal models when administered selenium at levels exceeding the nutritional requirements. One study showed efficacy in the prevention of malignancy while utilizing a selenium supplement in humans. The reports from such studies have heightened the interest in additional human selenium supplementation studies to validate the results in larger populations.  Interestingly, selenium is being studied as a potential therapy in the prevention or management of atherosclerosis.

Output: O=[Se](O)O


Input: The molecule is a phthalic acid monoester obtained by formal condensation of one of the carboxy groups of phthalic acid with the hydroxy group of hexanol. It is functionally related to a hexan-1-ol.

Output: CCCCCCOC(=O)C1=CC=CC=C1C(=O)O


Input: The molecule is a Standardized Chemical Allergen. The physiologic effect of chromium is by means of Increased Histamine Release, and Cell-mediated Immunity.

Output: [Cr]


Input: The molecule is an alpha-amino-acid cation obtained by deprotonation of the carboxy group and protonation of the amino groups of 4-hydroxy-L-lysine: major species at pH 7.3. It is a conjugate acid of a 4-hydroxy-L-lysine.

Output: [NH3+]CCC(O)C[C@H]([NH3+])C(=O)[O-]


Input: The molecule is an N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2. It is a N-alkylpyrrolidine, a pyridine alkaloid and a pyrrolidine alkaloid.

Output: CN1CCCC1C1=CC=CN=C1


Input: The molecule is a metabolite of the soy isoflavone daidzein by intestinal bacteria in approximately 80-90% of persons. Studies suggest beneficial health effects associated with daidzein-metabolizing phenotypes, and there is some small association between ODMA production and some phenotypes. Few dietary factors are associated with daidzein-metabolizing phenotypes. However, it remains unclear why some, but not all, persons harbor ODMA-producing bacteria. ODMA production is inversely associated with age, height, weight, and body mass index. In addition, Asians are less likely than whites to be ODMA producers, and former smokers were more likely than never smokers to be ODMA producers. Investigators have attempted to identify the bacteria involved in ODMA production, and several candidate bacteria were associated, but not definitely identified. ODMA production is correlated with the abundance of methanogens, indicating that the metabolic fate of daidzein may be related to intestinal H(2) metabolism.  (A3192, A3193).

Output: CC(C(=O)C1=CC=C(O)C=C1O)C1=CC=C(O)C=C1


Input: The molecule is conjugate base of ascr#3 It is a conjugate base of an ascr#3.

Output: C[C@H](CCCC/C=C/C(=O)[O-])O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O


Input: The molecule is a 26-oxo steroid resulting from the oxidation of (25R)-3beta,26-dihydroxycholest-5-en-7-one to the corresponding aldehyde. It is a 7-oxo steroid, a cholestanoid, a 26-oxo steroid, an oxysterol, a 3beta-sterol, a steroid aldehyde and a 3beta-hydroxy-Delta(5)-steroid. It derives from a cholesterol.

Output: C[C@H](CCC[C@@H](C)C=O)[C@H]1CC[C@H]2[C@@H]3C(=O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C


Input: The molecule is a cholesterol ester obtained by the formal condensation of the hydroxy group in cholesterol with the carboxy group of arachidonic acid. It has a role as an antibacterial agent and a mouse metabolite. It is functionally related to an arachidonic acid.

Output: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCCC(C)C)[C@@]4(C)CC[C@@H]32)C1


Input: The molecule is a primary aliphatic amine that is n-pentane in which a hydrogen of one of the methyl groups is replaced by an amino group. A water-soluble liquid with boiling point 104℃, it is a strong irritant.

Output: CCCCCN


Input: The molecule is an orally available, alkyl phospholipid that is used in the treatment of both cutaneous and visceral leishmaniasis. Miltefosine therapy is often accompanied by transient mild-to-moderate serum aminotransferase elevations during the first 1 or 2 weeks of treatment, but has not been implicated in cases of clinically apparent liver injury with jaundice.

Output: CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C


Input: The molecule is often attached to a Cer aglycon.

Output: CC(=O)N[C@H]1[C@H](O[C@@H]2[C@H](O[C@]3(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O3)[C@@H](O)[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)O[C@@H]3CO)O[C@@H]2CO)O[C@H](CO)[C@H](O)[C@@H]1O


Input: The molecule is a sesquiterpene alkaloid that is a macrolide incorporating a substituted pyridine and dihydroagarofuran moieties. Isolated from root barks of Tripterygium hypoglaucum, it exhibits anti-HIV activity. It has a role as an anti-HIV agent and a plant metabolite. It is a dihydroagarofuran sesquiterpenoid, an acetate ester, a 2-furoate ester, a macrolide, a sesquiterpene alkaloid and a pyridine alkaloid.

Output: CC(=O)OC[C@]12[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]3[C@@H](OC(C)=O)[C@@]14O[C@@]3(C)COC(=O)C1=CN=CC=C1C(C)C(C)(O)C(=O)O[C@@H]([C@H](OC(=O)C1=CC=CO1)[C@@H]2OC(C)=O)[C@]4(C)O


Input: The molecule is an aralkylamino compound. It is functionally related to a vanillyl alcohol. It is a conjugate base of a vanillylamine(1+).

Output: COC1=CC(CN)=CC=C1O


Input: The molecule is an organic thiophosphate and an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an agrochemical and an antinematodal drug.

Output: CCCSP(=O)(OCC)SCCC


Input: The molecule is a decaprenyl diphosphate having (Z)-stereochemistry about all but one of the double bonds. It is a conjugate acid of a (2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E)-decaprenyl diphosphate(3-).

Output: CC(C)=CCC/C(C)=C/CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\COP(=O)(O)OP(=O)(O)O


Input: The molecule is a monocarboxylic acid anion that is the conjugate base of glycosmisic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a conjugate base of a (2R,3S)-glycosmisic acid.

Output: COC1=CC([C@@H]2OC3=C(OC)C=C(/C=C/C(=O)[O-])C=C3[C@H]2CO)=CC=C1O


Input: The molecule is a monocarboxylic acid amide and an alpha-CH2-containing aldehyde. It has a role as a human metabolite and a mouse metabolite. It derives from a butanal.

Output: CC(=O)NCCCC=O


Input: The molecule is a member of the class of beta-carbolines that is 2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid in which one of the methylene protons at position 1 has been replaced by a 3-{[4-(2-fluorophenyl)piperazin-1-yl]methyl}-4-methoxyphenyl group. It has a role as a nicotinic acid adenine dinucleotide phosphate receptor antagonist. It is a member of beta-carbolines, an alpha-amino acid, a monomethoxybenzene, a member of monofluorobenzenes and a N-arylpiperazine.

Output: COC1=CC=C([C@H]2N[C@H](C(=O)O)CC3=C2NC2=CC=CC=C32)C=C1CN1CCN(C2=CC=CC=C2F)CC1


Input: The molecule is a dihydroxy-5beta-cholanic acid that is deoxycholic acid with a double bond at position 6. It has a role as a metabolite. It is a bile acid and a dihydroxy-5beta-cholanic acid. It derives from a deoxycholic acid.

Output: C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C=C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C


Input: The molecule is a semisynthetic glycopeptide used for the treatment of acute bacterial skin and skin structure infections caused or suspected to be caused by susceptible isolates of designated Gram-positive microorganisms including MRSA. It has a role as an antibacterial drug and an antimicrobial agent. It is a carbohydrate acid derivative, a monosaccharide derivative, a glycopeptide and a semisynthetic derivative.


Input: The molecule is a carboxyalkyl phosphate that is the 4-phosphate derivative of (R)-pantoic acid. It is functionally related to a (R)-pantoic acid. It is a conjugate acid of a (R)-4-phosphonatopantoate(3-).

Output: CC(C)(COP(=O)(O)O)[C@@H](O)C(=O)O


Input: The molecule is a 3-hydroxy steroid resulting from deoxygenation at position 17 of estradiol or estrone. It has a role as an estrogen. It is a 3-hydroxy steroid, a member of phenols and a phenolic steroid. It derives from a hydride of an estrane.

Output: C[C@@]12CCC[C@H]1[C@@H]1CCC3=CC(O)=CC=C3[C@H]1CC2


Input: The molecule is a farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent. It has a role as a flavouring agent, a cosmetic, a pheromone, a neuroprotective agent, an antifungal agent, an anti-inflammatory agent, an antihypertensive agent, an antioxidant, a volatile oil component, an insect attractant and a herbicide. It is a farnesane sesquiterpenoid, a tertiary allylic alcohol and a volatile organic compound.

Output: C=CC(C)(O)CC/C=C(\C)CCC=C(C)C


Input: The molecule is an amino sulfonic acid that is 4-[(4-methylenecyclohexa-2,5-dien-1-ylidene)amino]benzenesulfonic acid in which the hydrogens of the methylene group are replaced by 4-amino-3-methyl-5-sulfophenyl and 4-[(4-sulfophenyl)amino]phenyl groups. The disodium salt is the biological stain C.I. Acid Blue 22, also known as water blue. It is an organosulfonic acid, a ketimine and an amino sulfonic acid. It is a conjugate acid of a NSC 56820(2-).

Output: CC1=CC(C(=C2C=CC(=NC3=CC=C(S(=O)(=O)O)C=C3)C=C2)C2=CC=C(NC3=CC=C(S(=O)(=O)O)C=C3)C=C2)=CC(S(=O)(=O)O)=C1N


Input: The molecule is a D-mannofuranose in which the carbon bearing the anomeric hydroxy group has alpha configuration. It is an enantiomer of an alpha-L-mannofuranose.

Output: OC[C@@H](O)[C@H]1O[C@H](O)[C@@H](O)[C@H]1O


Input: The molecule is any benzoquinone derived from 2,3-dimethoxy-5-methylbenzoquinone; one of a group of naturally occurring homologues. The redox-active quinoid moiety usually carries a polyprenoid side chain at position 6, the number of isoprenoid units in which is species-specific. Ubiquinones are involved in the control of mitochondrial electron transport, and are also potent anti-oxidants. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a prenylquinone and a member of 1,4-benzoquinones. It derives from a 2,3-dihydroxy-5-methyl-1,4-benzoquinone.

Output: COC1=C(OC)C(=O)C(CC=C(C)C)=C(C)C1=O


Input: The molecule is the triphosphate salt of cordycepin, a purine nucleoside antimetabolite and antibiotic isolated from the fungus Cordyceps militaris with potential antineoplastic, antioxidant, and anti-inflammatory activities. Cordycepin is an inhibitor of polyadenylation, activates AMP-activated protein kinase (AMPK), and reduces mammalian target of rapamycin (mTOR) signaling, which may result in both the induction of tumor cell apoptosis and a decrease in tumor cell proliferation. mTOR, a serine/threonine kinase belonging to the phosphatidylinositol 3-kinase (PI3K)-related kinase (PIKK) family, plays an important role in the PI3K/AKT/mTOR signaling pathway that regulates cell growth and proliferation, and its expression or activity is frequently dysregulated in human cancers.

Output: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)C[C@H]1O


Input: The molecule is an argininium(2+). It is a conjugate acid of a D-argininium(1+). It is an enantiomer of a L-argininium(2+).

Output: NC(N)=[NH+]CCC[C@@H]([NH3+])C(=O)O


Input: The molecule is a cyclodiene organochlorine insecticide that is 3a,4,7,7a-tetrahydro-1H-4,7-methanoindene substituted by chlorine atoms at positions 1, 4, 5, 6, 7, 8 and 8. Formerly used to kill termites, ants and other insects in agricultural and domestic situations. It has a role as a GABA-gated chloride channel antagonist, an agrochemical, an antibacterial agent, a persistent organic pollutant and an antifungal agent. It derives from a hydride of a 1H-indene.

Output: ClC1=C(Cl)C2(Cl)C3C(Cl)C=CC3C1(Cl)C2(Cl)Cl


Input: The molecule is a long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of isomyristic acid. It is a long-chain fatty acyl-CoA, a methyl-branched fatty acyl-CoA and an 11,12-saturated fatty acyl-CoA. It is functionally related to an isomyristic acid. It is a conjugate acid of an isomyristoyl-CoA(4-).

Output: CC(C)CCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)(O)O


Input: The molecule is an amino trisaccharide consisting of alpha-L-fucose, beta-D-galactose and N-acetyl-D-glucosamine residues joined by sequential (1->2)- and (1->4)-linkages. It has a role as an epitope. It is an amino trisaccharide and a glucosamine oligosaccharide.

Output: CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]2O)[C@@H]1O


Input: The molecule is anthraquinone glycosides found in senna plant, usually referring to the sennosides A and B, with laxative activity. Sennosides act on and irritate the lining of the intestine wall, thereby causing increased intestinal muscle contractions leading to vigorous bowel movement.

Output: O=C(O)C1=CC(O)=C2C(=O)C3=C(OC4OC(CO)C(O)C(O)C4O)C=CC=C3C(C3C4=CC(C(=O)O)=CC(O)=C4C(=O)C4=C(OC5OC(CO)C(O)C(O)C5O)C=CC=C43)C2=C1


Input: The molecule is a radiopharmaceutical compound of a small synthetic cyclic peptide containing an RGD-sequence (Arg-Gly-Asp) labeled with the positron-emitting isotope fluorine F 18 that may be used to selectively image tumor cells and tumor vasculature by PET imaging. The RGD motif of fluciclatide F 18 selectively binds to the alphaVbeta3 integrin receptor, commonly upregulated on the surfaces of tumor cells and endothelial cells of tumor vasculature. This agent may be of use in visualizing and quantifying the development of tumor vascularity in response to antiangiogenic agents.


Input: The molecule is an organophosphate oxoanion that is the trianion of ditrans,polycis-tetradecaprenyl diphosphate arising from deprotonation of the diphosphate OH groups; major species at pH 7.3. It is a conjugate base of a ditrans,polycis-tetradecaprenyl diphosphate.

Output: CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\COP(=O)([O-])OP(=O)([O-])[O-]


Input: The molecule is a 1-O-acyl-N-acylsphingosine in which the N- and O-acyl groups are specified as acetyl and palmitoyl (hexadecanoyl) respectively. It is functionally related to a hexadecanoic acid and a N-acetylsphingosine.

Output: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COC(=O)CCCCCCCCCCCCCCC)NC(C)=O


Input: The molecule is as a Cytochrome P450 3A Inducer, and Cytochrome P450 2B6 Inducer, and Cytochrome P450 2C8 Inducer, and Cytochrome P450 2C9 Inducer, and Cytochrome P450 2C19 Inducer, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C9 Inhibitor, and P-Glycoprotein Inducer, and P-Glycoprotein Inhibitor.

Output: CC1=CC=C(NC(=O)C2(C3=CC=C4OC(F)(F)OC4=C3)CC2)N=C1C1=CC=CC(C(=O)O)=C1


Input: The molecule is an amino trisaccharide consisting of D-galactopyranose, 2-acetamido-2-deoxy-D-glucopyranose and 2-acetamido-2-deoxy-D-galactopyranose residues joined in sequence by (1->4) and (1->3) glycosidic bonds. The alpha/beta configuration at position 1 of each of the pyranose rings is not stated. It is a member of acetamides, an amino trisaccharide, a glucosamine oligosaccharide and a partially-defined glycan. It is functionally related to a D-Galp-(1->4)-D-GlcpNAc.

Output: CC(=O)N[C@H]1C(O[C@H]2[C@@H](O)[C@@H](CO)OC(O)[C@@H]2NC(C)=O)O[C@H](CO)[C@@H](OC2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O


Input: The molecule is naturally occurring in the environment. Manganese is essential for normal physiologic functioning in humans and animals, and exposure to low levels of manganese in the diet is considered to be nutritionally essential in humans. Chronic (long-term) exposure to high levels of manganese by inhalation in humans may result in central nervous system (CNS) effects. Visual reaction time, hand steadiness, and eye- hand coordination were affected in chronically-exposed workers. A syndrome named manganism may result from chronic exposure to higher levels; manganism is characterized by feelings of weakness and lethargy, tremors, a mask-like face, and psychological disturbances. Respiratory effects have also been noted in workers chronically exposed to manganese bearing particles by inhalation.

Output: [Mn]


Input: The molecule is tetraanion of 1,5-dihydrocoenzyme F420 arising from deprotonation of acidic OH groups from carboxylic acid and phosphate functions. It is a conjugate base of a 1,5-dihydrocoenzyme F420.

Output: C[C@H](OP(=O)([O-])OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=CC(O)=CC=C2CC2=C1NC(=O)NC2=O)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-])C(=O)[O-]


Input: The molecule is a 17beta-hydroxy steroid that is estrane containing a double bond between positions 4 and 5 and substituted by an ethyl group and a hydroxy group at the 17alpha and 17beta positions, respectively. It is an anabolic steroid that has little androgenic effect and only slight progestational activity. It has been used to promote growth in boys with delayed bone growth. It has a role as an anabolic agent. It is a tertiary alcohol and a 17beta-hydroxy steroid.

Output: CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3CC[C@@]21C


Input: The molecule is a steroid ester that is methyl (5alpha)-cholest-1-en-21-oate substituted by an oxo group at position 3. Isolated from Hainan soft coral Dendronephthya studeri, it exhibits antitumour activity. It has a role as a coral metabolite. It is a cholestanoid, a steroid ester and a 3-oxo-Delta(1) steroid. It derives from a hydride of a 5alpha-cholestane.

Output: COC(=O)[C@H](CCCC(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C


Input: The molecule is an organooxygen compound. It is functionally related to a tetracarboxylic acid.

Output: CC(=O)OCC1=COC(OC(=O)C(OC(C)=O)C(C)C)C2C1=CC(OC(=O)CC(C)C)C21CO1


Input: The molecule is a glycosyloxyflavone that is luteolin with a 6-O-beta-D-arabinopyranosyl-beta-D-glucopyranosyl entity attached at position 7 via a glycosidic linkage. It has a role as a metabolite. It is a glycosyloxyflavone, a trihydroxyflavone and a disaccharide derivative. It is functionally related to a luteolin.

Output: O=C1C=C(C2=CC=C(O)C(O)=C2)OC2=CC(O[C@@H]3O[C@H](CO[C@@H]4OC[C@@H](O)[C@@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C12


Input: The molecule is conjugate base of biotin arising from deprotonation of the carboxy group. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite and a cofactor. It is a monocarboxylic acid anion and a vitamin B7. It is a conjugate base of a biotin.

Output: O=C([O-])CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21


Input: The molecule is a medium chain fatty acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate functions of 2-hydroxy-3-methylnonanoyl-CoA; major species at pH 7.3. It is a medium-chain fatty acyl-CoA(4-) and a methyl-branched fatty acyl-CoA(4-). It is functionally related to a 3-methylnonanoyl-CoA(4-). It is a conjugate base of a 2-hydroxy-3-methylnonanoyl-CoA.

Output: CCCCCCC(C)C(O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]


Input: The molecule is an antidiabetic medication from the thiazolidinedione class of drugs. It primarily functions as an insulin sensitizer by binding and activating Peroxisome Proliferator-Activated Receptors (PPAR) gamma within fat cells. By activating PPAR-gamma and promoting the binding of insulin at fat cells, lobeglitazone thereby has been shown to reduce blood sugar levels, lower hemoglobain A1C (HbA1C) levels, and improve lipid and liver profiles. Unlike [DB01132], which is a dual PPAR agonist at PPAR-alpha and PPAR-gamma, Lobeglitazone is a pure PPAR-alpha agonist.   Lobeglitazone was approved by the Ministry of Food and Drug Safety (South Korea) in 2013, and is being monitored by postmarketing surveillance until 2019. Lobeglitazone is not approved for use by either the Food and Drug Administration (USA), Health Canada, or by the European Medicines Agency for use in the management of diabetes.

Output: COC1=CC=C(OC2=CC(N(C)CCOC3=CC=C(CC4SC(=O)NC4=O)C=C3)=NC=N2)C=C1


Input: The molecule is a potent and highly selective ET[A] receptor blocker and is clinically investigated in diabetic nephropathy. This study was designed to evaluate whether avosentan influences the pharmacokinetics of steroid oral contraceptives.

Output: COC1=CC=CC=C1OC1=C(OC)N=C(C2=CC=NC=C2)N=C1NS(=O)(=O)C1=CC=C(C)C=N1


Input: The molecule is a tripeptide composed of two L-alanyl and an L-aspartic acid residue joined in sequence. It has a role as a metabolite. It derives from a L-alanine and a L-aspartic acid.

Output: C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)O


Input: The molecule is a branched amino pentasaccharide consisting of three alpha-L-rhamnose residues [linked sequentially (1->3) and (1->2); one at the reducing end] and two N-acetyl beta-D-glucosaminyl residues [one linked (1->3) to the reducing-end rhamnose and the other linked (1->3) to the non-reducing-end rhamnose].


Input: The molecule is a very long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-hydroxytetracosanoic acid. It has a role as a human metabolite and a Saccharomyces cerevisiae metabolite. It is a 3-hydroxy fatty acyl-CoA and a very long-chain fatty acyl-CoA. It derives from a 3-hydroxytetracosanoic acid. It is a conjugate acid of a 3-hydroxytetracosanoyl-CoA(4-).

Output: CCCCCCCCCCCCCCCCCCCCCC(O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)(O)O


Input: The molecule is the (3S)-trans-diastereomer of 3-hydroxy-L-proline. It has a role as a metabolite. It is a tautomer of a trans-3-hydroxy-L-proline zwitterion.

Output: O=C(O)[C@H]1NCC[C@@H]1O


Input: The molecule is a naturally occurring element found in rocks, animals, plants, soil, and in volcanic dust and gases. Chromium is present in the environment in several different forms. The most common forms are chromium(0), chromium(III), and chromium(VI). No taste or odor is associated with chromium compounds. Chromium(III) occurs naturally in the environment and is an essential nutrient. Chromium(VI) and chromium(0) are generally produced by industrial processes. The metal chromium, which is the chromium(0) form, is used for making steel. Chromium(VI) and chromium(III) are used for chrome plating, dyes and pigments, leather tanning, and wood preserving.

Output: [Cr]


Input: The molecule is an amino disaccharide consisting of alpha-D-glucofuranosyl and 2-acetamido-2-deoxy-beta-D-glucopyranose residues joined in sequence by a (1->3) glycosidic bond. It is an amino disaccharide and a member of acetamides. It is functionally related to an alpha-D-galactofuranose and a N-acetyl-beta-D-glucosamine.

Output: CC(=O)N[C@@H]1[C@@H](O[C@H]2O[C@@H]([C@H](O)CO)[C@H](O)[C@H]2O)[C@H](O)[C@@H](CO)O[C@H]1O


Input: The molecule is an alpha-amino-acid cation obtained by deprotonation of the carboxy group and protonation of the amino groups of (3S)-3-hydroxy-L-ornithine: major species at pH 7.3. It is a conjugate acid of a (3S)-3-hydroxy-L-ornithine.

Output: [NH3+]CC[C@H](O)[C@H]([NH3+])C(=O)[O-]


Input: The molecule is a phospholipid that is the hexadecyl monoester of phosphocholine. It has a role as an antineoplastic agent, an antiprotozoal drug, an antifungal agent, an immunomodulator, an anti-inflammatory agent, an apoptosis inducer, a protein kinase inhibitor and an anticoronaviral agent. It is a member of phosphocholines and a phospholipid.

Output: CCCCCCCCCCCCCCCCOP(=O)([O-])OCC[N+](C)(C)C


Input: The molecule is the hydrochloride salt of benzphetamine. A sympathomimetic agent with properties similar to dextroamphetamine, it is used in the treatment of obesity. It has a role as an adrenergic uptake inhibitor, an appetite depressant, a dopamine uptake inhibitor and a sympathomimetic agent. It contains a benzphetamine.

Output: C[C@@H](CC1=CC=CC=C1)[NH+](C)CC1=CC=CC=C1;[Cl-]


Input: The molecule is used for the treatment of most tapeworm infections. Helminths (worms) are multicellular organisms that infect very large numbers of humans and cause a broad range of diseases. Over 1 billion people are infected with intestinal nematodes, and many millions are infected with filarial nematodes, flukes, and tapeworms. They are an even greater problem in domestic animals.

Output: O=C(NC1=CC=C([N+](=O)[O-])C=C1Cl)C1=CC(Cl)=CC=C1O


Input: The molecule is a ring assembly composed of fisetinidol and gallocatechin units. Isolated from Acacia mearnsii, it exhibits inhibitory activity against alpha-amylase. It has a role as a metabolite and an EC 3.2.1.1 (alpha-amylase) inhibitor. It is a catechin and a ring assembly. It is functionally related to a fisetinidol and a (+)-gallocatechin.

Output: OC1=CC=C2C(=C1)O[C@H](C1=CC=C(O)C(O)=C1)[C@@H](O)[C@@H]2C1=C(O)C=C2O[C@H](C3=CC(O)=C(O)C(O)=C3)[C@@H](O)CC2=C1O


Input: The molecule are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release.

Output: CN1CCC(=C2C3=CC=CC=C3CCC3=CC=CN=C23)CC1


Input: The molecule is a medication used to treat constipation and empty the large intestine before surgery. The medication is taken by mouth or via the rectum. It typically begins working in minutes when given by rectum and within twelve hours when given by mouth. It is a weaker laxative than bisacodyl or castor oil. Sennoside A, one of the sennosides present in the laxative medication, has recently proven effective in inhibiting the ribonuclease H (RNase H) activity of human immunodeficiency virus (HIV) reverse transcriptase.

Output: O=C(O)C1=CC(O)=C2C(=O)C3=C(OC4OC(CO)C(O)C(O)C4O)C=CC=C3C(C3C4=CC(C(=O)O)=CC(O)=C4C(=O)C4=C(OC5OC(CO)C(O)C(O)C5O)C=CC=C43)C2=C1


Input: The molecule is a leukotriene that is 10,11-dihydroleukotriene B4 in which the three methyl hydrogens at position 20 have been replaced by hydroxy groups. It is a leukotriene, a long-chain fatty acid and a hydroxy polyunsaturated fatty acid. It derives from a leukotriene B4. It is a conjugate acid of a 10,11-dihydro-20,20,20-trihydroxyleukotriene B4(1-).

Output: O=C(O)CCC[C@H](O)/C=C\C=C\CC[C@H](O)C/C=C\CCCCC(O)(O)O


Input: The molecule is a steroid sulfate that is 5alpha-ergostane substituted by sulfate groups at positions 2, 3 and 6 (the (2beta,3alpha,6alpha stereoisomer). It has a role as an anti-HIV-1 agent, an anti-HIV-2 agent and a metabolite. It is a conjugate acid of a halistanol sulfate G(3-). It derives from a hydride of a 5alpha-ergostane.

Output: CC(C)[C@@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@H](OS(=O)(=O)O)[C@H]4C[C@H](OS(=O)(=O)O)[C@@H](OS(=O)(=O)O)C[C@]4(C)[C@H]3CC[C@]12C


Input: The molecule is a Radioactive Diagnostic Agent. The mechanism of action of it is as a Radiopharmaceutical Activity.

Output: [Rb+]


Input: The molecule is an N-methylglycine that is glycine carrying two N-methyl substituents. It has a role as a human metabolite, a Daphnia magna metabolite and a mouse metabolite. It is a N-methyl-amino acid and a member of N-methylglycines. It is a tautomer of a N,N-dimethylglycine zwitterion.

Output: CN(C)CC(=O)O


Input: The molecule is a synthetic antisense oligonucleotide designed to cause skipping of abnormal exons in the synthesis of the dystrophin gene and that is used to treat Duchenne muscular dystrophy. Viltolarsen has not been reported to cause ALT elevations during therapy and has not been linked to instances of acute liver injury with symptoms and jaundice.


Input: The molecule is a leukotriene that is 10,11-dihydroleukotriene B4 in which the three methyl hydrogens at position 20 have been replaced by hydroxy groups. It is a leukotriene, a long-chain fatty acid and a hydroxy polyunsaturated fatty acid. It is functionally related to a leukotriene B4. It is a conjugate acid of a 10,11-dihydro-20,20,20-trihydroxyleukotriene B4(1-).

Output: O=C(O)CCC[C@H](O)/C=C\C=C\CC[C@H](O)C/C=C\CCCCC(O)(O)O


Input: The molecule is a trihydroxyflavone that is flavone substituted by hydroxy groups at positioms 5, 6 and 3' and methoxy groups at positions 3, 7 and 4' respectively. It has a role as a plant metabolite. It is a trihydroxyflavone and a trimethoxyflavone. It is functionally related to a flavone.

Output: COC1=CC=C(C2=C(OC)C(=O)C3=C(O)C(O)=C(OC)C=C3O2)C=C1O


Input: The molecule is a member of the class of 7-hydroxyisoflavones that is 3-phenyl-4H-chromen-4-one which is substituted by a hydroxy group at position 7 and chloro groups at positions 2' and 4'. It is a SIRT1 activator. It is a member of 7-hydroxyisoflavones and a dichlorobenzene.

Output: O=C1C(C2=CC=C(Cl)C=C2Cl)=COC2=CC(O)=CC=C12


Input: The molecule is an orally bioavailable, non-nucleoside, 3,4-dihydroquinazolinyl acetic acid and inhibitor of the pUL56 subunit of the viral terminase complex of cytomegalovirus (CMV), with potential CMV-specific antiviral activity. Upon oral administration, letermovir binds to the pUL56 subunit of the viral terminase complex of CMV and prevents the cleavage of concatemeric DNA into monomeric genome length DNA. As this agent interferes with viral DNA processing and subsequent viral DNA packaging into procapsids, CMV replication is blocked and CMV infection is prevented.

Output: COC1=CC=CC(N2CCN(C3=NC4=C(F)C=CC=C4[C@H](CC(=O)O)N3C3=CC(C(F)(F)F)=CC=C3OC)CC2)=C1


Input: The molecule is the L-enantiomer of lanthionine. It is a lanthionine, a non-proteinogenic L-alpha-amino acid and a L-alanine derivative. It is a tautomer of a L-lanthionine dizwitterion.

Output: N[C@@H](CSC[C@H](N)C(=O)O)C(=O)O


Input: The molecule is a docosanoid that is (4Z,7Z,11Z,13Z,15E,19Z)-docosahexaenoic acid carrying two hydroperoxy substituents at positions 10 and 17. It has a role as a human xenobiotic metabolite. It is a hydroperoxy fatty acid, a lipid hydroperoxide, a docosanoid and a long-chain fatty acid. It derives from an all-cis-docosa-4,7,10,13,16,19-hexaenoic acid. It is a conjugate base of a (4Z,7Z,11Z,13Z,15E,17S,19Z)-10,17-bis(hydroperoxy)docosahexaenoate.

Output: CC/C=C\C[C@@H](/C=C/C=C\C=C/C(C/C=C\C/C=C\CCC(=O)O)OO)OO


Input: The molecule is a Phosphodiesterase 4 Inhibitor. The mechanism of action of it is as a Phosphodiesterase 4 Inhibitor.

Output: N#CC1=CC=C(OC2=CC=C3B(O)OCC3=C2)C=C1


Input: The molecule is a 3-chloroalanine that has S configutation at the chiral centre. It has a role as an EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor. It is a D-alanine derivative and a 3-chloroalanine. It is an enantiomer of a 3-chloro-L-alanine. It is a tautomer of a 3-chloro-D-alanine zwitterion.

Output: N[C@H](CCl)C(=O)O


Input: The molecule is an alicyclic ketone which is 3-oxocyclopent-1-ene substituted by a formamido group at position 1 as well as vinyl and hydroxy groups at position 4. It is isolated from a marine derived fungus Myrothecium sp. and acts as an inhibitor of tyrosinase enzyme (EC 1.14.18.1). It has a role as a metabolite and an EC 1.14.18.1 (tyrosinase) inhibitor. It is a member of formamides, a tertiary alcohol, an alicyclic ketone and a tertiary alpha-hydroxy ketone.

Output: C=C[C@]1(O)CC(NC=O)=CC1=O


Input: The molecule is an epoxy(hydroxy)icosatrienoic acid that is (5Z,8Z,14Z)-icosatrienoic acid having the epoxide group across positions 11-12 and the hydroxy substituent located at position 20. It is an epoxy(hydroxy)icosatrienoic acid and an omega-hydroxy fatty acid. It derives from an arachidonic acid. It is a conjugate acid of an 11,12-epoxy-20-hydroxy-(5Z,8Z,14Z)-icosatrienoate.

Output: O=C(O)CCC/C=C\C/C=C\CC1OC1C/C=C\CCCCCO


Input: The molecule is a dipeptide obtained by formal condensation of the gamma-carboxy group of glutamic acid with the amino group of another glutamic acid. It has a role as a human metabolite. It is functionally related to a L-glutamic acid. It is a conjugate acid of a gamma-Glu-Glu(2-).

Output: N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O


Input: The molecule is an organooxygen compound and an organonitrogen compound. It is functionally related to a beta-amino acid.

Output: COC1=CC=C(CN(C)C[C@@H]2OC3=CC=C(NC(=O)CCN4CCOCC4)C=C3C(=O)N([C@H](C)CO)C[C@H]2C)C=C1


Input: The molecule is an organooxygen compound and an organonitrogen compound. It is functionally related to a gamma-amino acid.

Output: NCCCNCCCC(=O)O


Input: The molecule is an alkaloid isolated from the stem wood of the Chinese tree, Camptotheca acuminata. This compound selectively inhibits the nuclear enzyme DNA topoisomerase, type I. Several semisynthetic analogs of camptothecin have demonstrated antitumor activity.

Output: CC[C@@]1(O)C(=O)OCC2=C1C=C1C3=NC4=CC=CC=C4C=C3CN1C2=O


Input: The molecule is the N-sulfoglucosamine formed by sulfating the amino group of D-glucosamine. It is a conjugate acid of a N-sulfo-D-glucosamine(1-).

Output: O=S(=O)(O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O


Input: The molecule is an imidazolyl carboxylic acid anion that is the conjugate base of dihydrourocanic acid, obtained by deprotonation of the carboxy group. It derives from a propionate. It is a conjugate base of a dihydrourocanic acid.

Output: O=C([O-])CCC1=CN=CN1


Input: The molecule is a Porphyrin Precursor and Optical Imaging Agent. The mechanism of action of it is as a Fluorescence Contrast Activity.

Output: NCC(=O)CCC(=O)O


Input: The molecule is a mannosylinositol phosphorylceramide compound having a tetracosanoyl group amide-linked to a C20 phytosphingosine base, with hydroxylation at C-2 and C-3 of the C24 very-long-chain fatty acid. It is functionally related to an Ins-1-P-Cer(t20:0/2,3-OH-24:0).

Output: CCCCCCCCCCCCCCCCCCCCCC(O)C(O)C(=O)N[C@@H](COP(=O)(O)O[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)[C@H](O)C(O)CCCCCCCCCCCCCCCC


Input: The molecule is a benzo[5,6]cyclohepta[1,2-b]pyridine having a 1-methylpiperidin-4-ylidene group at the 11-position. It has a role as a H1-receptor antagonist and an anti-allergic agent. It is a benzocycloheptapyridine and a tertiary amine.

Output: CN1CCC(=C2C3=CC=CC=C3CCC3=CC=CN=C23)CC1


Input: The molecule is an acyl-CoA(4-) that is the tetraanion of (2S,3S)-3-hydroxy-2-methylbutanoyl-CoA, arising from deprotonation of the phosphate and diphosphate OH groups. It has a role as a human metabolite. It is a conjugate base of a (2S,3S)-3-hydroxy-2-methylbutanoyl-CoA.

Output: C[C@H](O)[C@H](C)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]


Input: The molecule is an amino disaccharide consisting of beta-D-galactose having an N-acetyl-alpha-D-galactosaminyl residue attached at the 2-position. It is an amino disaccharide and a glycosylgalactose derivative.

Output: CC(=O)N[C@H]1[C@@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2O)O[C@H](CO)[C@H](O)[C@@H]1O


Input: The molecule is a member of the class of pyrimidine ribonucleosides that is zebularine in which the double bond between positions 3 and 4 of the pyrimidone ring has been reduced to a single bond. It is a pyrimidone and a member of pyrimidine ribonucleosides. It is functionally related to a zebularine.

Output: O=C1NCC=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O


Input: The molecule is a quinolinemonocarboxylic acid with broad-spectrum antibacterial activity against most gram-negative and gram-positive bacteria. Norfloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase. It has a role as an antibacterial drug, a DNA synthesis inhibitor, a xenobiotic and an environmental contaminant. It is a quinolinemonocarboxylic acid, a N-arylpiperazine, a quinolone, a quinolone antibiotic and a fluoroquinolone antibiotic.

Output: CCN1C=C(C(=O)O)C(=O)C2=CC(F)=C(N3CCNCC3)C=C21


Input: The molecule is the zwitterion resulting from the transfer of a proton from the carboxylic acid group to the amino group of (R)-nipecotic acid. It is a tautomer of a (R)-nipecotic acid.

Output: O=C([O-])[C@@H]1CCC[NH2+]C1


Input: The molecule is a member of the class of pyrazolopyrimidine that is pyrazolo[3,4-d]pyrimidin-4-amine bearing additional tert-butyl and 4-chlorophenyl substituents at positions 1 and 3 respectively. It is a potent ATP-competitive inhibitor of the Src family of protein tyrosine kinases. It has a role as an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor, a beta-adrenergic antagonist and a geroprotector. It is a pyrazolopyrimidine, an aromatic amine and a member of monochlorobenzenes.

Output: CC(C)(C)N1N=C(C2=CC=C(Cl)C=C2)C2=C(N)N=CN=C21


Input: The molecule is a Serotonin-2c Receptor Agonist. The mechanism of action of it is as a Serotonin 2c Receptor Agonist, and Cytochrome P450 2D6 Inhibitor.

Output: C[C@H]1CNCCC2=CC=C(Cl)C=C21


Input: The molecule is a Phosphodiesterase 4 Inhibitor. The mechanism of action of it is as a Phosphodiesterase 4 Inhibitor.

Output: O=C(NC1=C(Cl)C=NC=C1Cl)C1=CC=C(OC(F)F)C(OCC2CC2)=C1


Input: The molecule is a benzazepine that is 2,3,4,5-tetrahydro-1H-2-benzazepine which is substituted by hydroxy groups at positions 7 and 8 and on the nitrogen atom by a 2-(p-chlorophenyl)ethylaminothiocarbonyl group. A synthetic analogue of capsaicin, it was the first reported capsaicin receptor antagonist. It has a role as a capsaicin receptor antagonist. It is a member of catechols, a member of thioureas, a benzazepine and a member of monochlorobenzenes.

Output: OC1=CC2=C(C=C1O)CN(C(=S)NCCC1=CC=C(Cl)C=C1)CCC2


Input: The molecule is a hydroxyisoflavanone that is isoflavanone substituted by hydroxy groups at positions 5, 7 and 4', a methoxy substituent at position 2' and a prenyl group at position 3'. It has a role as an antimicrobial agent, a cyclooxygenase 1 inhibitor and a metabolite. It is a hydroxyisoflavanone and a methoxyisoflavanone.

Output: COC1=C(C2COC3C=C(O)C=C(O)C3C2=O)C=CC(O)=C1CC=C(C)C


Input: The molecule is a monohydroxybenzoic acid that is benzoic acid substituted by a hydroxy group at position 6 and a 2-phenylethenyl group at position 2 which in turn is attached to a beta-D-glucopyranosyloxy group at position 4. It has been isolated from the roots of Scorzonera judaica. It has a role as a metabolite and a plant metabolite. It is a monohydroxybenzoic acid, a monosaccharide derivative and a beta-D-glucoside.

Output: O=C(O)C1=C(O)C=CC=C1/C=C/C1=CC=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C1


Input: The molecule is an olefinic compound. It is functionally related to an acrylic acid.

Output: CCOC(=O)/C=C/I


Input: The molecule is a pyrroledicarboxylic acid that is pyrrole-2,5-dicarboxylic acid in which the hydrogens at positions 3 and 4 have been replaced by indol-3-yl groups. It has a role as a bacterial metabolite. It is a member of indoles and a pyrroledicarboxylic acid. It is a conjugate acid of a chromopyrrolate(2-).

Output: O=C(O)C1=C(C2=CNC3=CC=CC=C23)C(C2=CNC3=CC=CC=C23)=C(C(=O)O)N1


Input: The molecule is a fungistatic and antimicrobial derivative of aspergillic acid. Although the exact mechanism of action remains to be fully elucidated, pyrithione appears to interfere with membrane transport ultimately leading to a loss of metabolic control.

Output: ON1C=CC=CC1=S


Input: The molecule is a 3-oxo monocarboxylic acid anion that is the conjugate base of 3-oxodecanoic acid, obtained by deprotonation of the carboxy group. It is a conjugate base of a 3-oxodecanoic acid.

Output: CCCCCCCC(=O)CC(=O)[O-]


Input: The molecule is a member of the class of dihydroxybenzoic acids that is o-orsellinic acid carrying two additional methyl substituents at positions 3 and 5. It has a role as an Aspergillus metabolite. It is a dihydroxybenzoic acid and a member of resorcinols. It derives from an o-orsellinic acid. It is a conjugate acid of a 3,5-dimethylorsellinate.

Output: CC1=C(C)C(C(=O)O)=C(O)C(C)=C1O


Input: The molecule is a sulfamoylbenzoic acid-based agent and indapamide analog, with diuretic activity. Zidapamide, formerly known as isodapamide, acts in a similar manner as the thiazide-like diuretic indapamide. This agent has never been marketed.

Output: CC1C2=CC=CC=C2CN1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1


Input: The molecule is a cysteine derivative obtained by formal condensation between N-butyl-L-cysteinamide and 2-thienylacetic acid. It is a member of thiophenes, a monocarboxylic acid amide and a L-cysteine derivative.

Output: CCCCNC(=O)[C@H](CS)NC(=O)CC1=CC=CS1


Input: The molecule is a Potassium Channel Blocker. The mechanism of action of it is as a Potassium Channel Antagonist.

Output: NC1=CC=NC=C1N


Input: The molecule is the cis-form of 4-coumaric acid. It is a conjugate acid of a cis-4-coumarate.

Output: O=C(O)/C=C\C1=CC=C(O)C=C1


Input: The molecule is a benzamide obtained by formal condensation of the carboxy group of 5-chloro-2-methoxy-4-(methylamino)benzoic acid with the amino group of 1-benzyl-2-methylpyrrolidin-3-amine. It is a N-alkylpyrrolidine, a member of benzamides, a tertiary amino compound and a member of monochlorobenzenes.

Output: CNC1=CC(OC)=C(C(=O)NC2CCN(CC3=CC=CC=C3)C2C)C=C1Cl


Input: The molecule is a triterpenoid obtained by methylation at position 3 of squalene with concomitant double bond migration from position 2 to position 1. It has a role as a metabolite. It derives from a squalene.

Output: C=C(C)C(C)CC/C(C)=C/CC/C(C)=C/CC/C=C(\C)CC/C=C(\C)CCC=C(C)C


Input: The molecule is a semisynthetic derivative of camptothecin, a cytotoxic, quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata. Topotecan inhibits topoisomerase I activity by stabilizing the topoisomerase I-DNA covalent complexes during S phase of cell cycle, thereby inhibiting religation of topoisomerase I-mediated single-strand DNA breaks and producing potentially lethal double-strand DNA breaks when encountered by the DNA replication machinery.

Output: CC[C@@]1(O)C(=O)OCC2=C1C=C1C3=NC4=CC=C(O)C(CN(C)C)=C4C=C3CN1C2=O


Input: The molecule is a dipeptide formed from L-phenylalanine and L-methionine residues. It has a role as a metabolite. It is a tautomer of a Phe-Met zwitterion.

Output: CSCC[C@H](NC(=O)[C@@H](N)CC1=CC=CC=C1)C(=O)O


Input: The molecule is a member of the class of chromenes that is 2H-chromene substituted by a methoxy group at position 7 and two methyl groups at position 2. It has a role as a member of precocenes and a plant metabolite. It is a member of chromenes and an aromatic ether.

Output: COC1=CC=C2C=CC(C)(C)OC2=C1


Input: The molecule is a 3-hydroxy steroid that is obtained by formal dehydrogenation across positions 7 and 8 of 17beta-estradiol. It has a role as a metabolite. It is a 17beta-hydroxy steroid and a 3-hydroxy steroid. It is functionally related to an androstane.

Output: C[C@]12CC[C@H]3C(=CCC4=CC(O)=CC=C43)[C@@H]1CC[C@@H]2O


Input: The molecule is an organosulfonate oxoanion obtained by deprotonation of the sulfo groups of Congo corinth (acid form). It is a conjugate base of a Congo corinth (acid form).

Output: NC1=C(N=NC2=CC=C(C3=CC=C(N=NC4=CC(S(=O)(=O)[O-])=C5C=CC=CC5=C4O)C=C3)C=C2)C=C(S(=O)(=O)[O-])C2=CC=CC=C12


Input: The molecule is the S-enantiomer of 2-hydroxypalmitate. It is a conjugate base of a (S)-2-hydroxyhexadecanoic acid. It is an enantiomer of a (R)-2-hydroxyhexadecanoate.

Output: CCCCCCCCCCCCCC[C@H](O)C(=O)[O-]


Input: The molecule is a penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido group. It is a penicillin and a penicillin allergen. It derives from an ampicillin.

Output: CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CCC=CC3)C(=O)N2[C@H]1C(=O)O


Input: The molecule is a substituted benzimidazole derivative with activity against rhinoviruses and enteroviruses. Enviroxime is a kinase inhibitor that targets viral protein 3A and 3AB, which are involved in viral RNA replication complex formation, thereby resulting in suppression of viral replication.

Output: CC(C)S(=O)(=O)N1C(N)=NC2=CC=C(/C(=N/O)C3=CC=CC=C3)C=C21


Input: The molecule is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.

Output: CCCC#CC1=CC=C2C(=C1)O[C@@H](CN(C)C(=O)CN(C)C)[C@H](C)CN([C@H](C)CO)S2(=O)=O


Input: The molecule is a D-allofuranose. It is an enantiomer of an alpha-L-allofuranose.

Output: OC[C@@H](O)[C@H]1O[C@H](O)[C@H](O)[C@@H]1O


Input: The molecule is a dinucleotide comprising adenosine and guanosine connected by a 3'->5 linkage and with a phosphoric group at the 5'-terminus; major species at pH 7.3.

Output: NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(=O)([O-])O[C@H]3[C@@H](O)[C@H](N4C=NC5=C(N)N=CN=C54)O[C@@H]3COP(=O)([O-])[O-])[C@@H](O)[C@H]2O)C(=O)N1


Input: The molecule is a parenterally administered alkylating agent used alone and in combination with other antineoplastic agents in the treatment of chronic lymphocytic leukemia and refractory forms of non-Hodgkin lymphoma. Bendamustine therapy is associated with minor transient serum enzyme elevations during treatment and to rare instances of clinically apparent liver injury, with jaundice generally arising as a part of a generalized hypersensitivity syndrome. Bendamustine also has potent immunosuppressive activity and can cause reactivation of chronic hepatitis B that can be severe and even fatal.

Output: CN1C(CCCC(=O)O)=NC2=CC(N(CCCl)CCCl)=CC=C21


Input: The molecule is a hydroxyoctadecanoic acid that is octadecanoic acid (stearic acid) in which one of the hydrogens at position 5 has been replaced by a hydroxy group. It is a conjugate acid of a 5-hydroxyoctadecanoate.

Output: CCCCCCCCCCCCCC(O)CCCC(=O)O


Input: The molecule is a 3-hydroxy fatty acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of (3R,8Z,11Z,14Z,17Z)-3-hydroxyicosatetraenoyl-CoA; major species at pH 7.3. It is a (R)-3-hydroxyacyl-CoA(4-) and a 3-hydroxy fatty acyl-CoA(4-). It is a conjugate base of a (3R,8Z,11Z,14Z,17Z)-3-hydroxyicosatetraenoyl-CoA.

Output: CC/C=C\C/C=C\C/C=C\C/C=C\CCCC[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]


Input: The molecule is a branched-chain fatty acid that is 4-methylpentanoic acid carrying an oxo substituent at C-3. It is a branched-chain fatty acid and a 3-oxo fatty acid. It is functionally related to a valeric acid. It is a conjugate acid of a 4-methyl-3-oxopentanoate.

Output: CC(C)C(=O)CC(=O)O


Input: The molecule is an enoate ester obtained by formal condensation of the carboxy group of 3,3-dimethylacrylic acid with the phenolic hydroxy group of dinoseb. It is a C-nitro compound and an enoate ester. It derives from a dinoseb.

Output: CCC(C)C1=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1OC(=O)C=C(C)C


Input: The molecule is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4' and a prenyl group at position 3'. It has a role as an antibacterial agent, a platelet aggregation inhibitor and a metabolite. It is a polyphenol and a member of chalcones. It is functionally related to a trans-chalcone.

Output: CC(C)=CCC1=C(O)C=CC(C(=O)/C=C/C2=CC=C(O)C=C2)=C1O


Input: The molecule is a Serotonin and Norepinephrine Reuptake Inhibitor. The mechanism of action of it is as a Norepinephrine Uptake Inhibitor, and Serotonin Uptake Inhibitor.

Output: COC1=CC=C(C(CN(C)C)C2(O)CCCCC2)C=C1


Input: The molecule is an amino acid zwitterion arising from transfer of a proton from the carboxy to the amino group of 2-methylserine; major species at pH 7.3 It is a tautomer of a 2-methyl-DL-serine.

Output: CC([NH3+])(CO)C(=O)[O-]


Input: The molecule is an N-(long-chain-acyl)ethanolamine resulting from the formal condensation of the carboxy group of dodecanoic acid (myristic acid) with the amino group of ethanolamine. It is a N-(long-chain-acyl)ethanolamine and a N-(saturated fatty acyl)ethanolamine. It derives from a dodecanoic acid.

Output: CCCCCCCCCCCC(=O)NCCO


Input: The molecule is an alkane comprising of two carbon atoms. It has a role as a refrigerant and a plant metabolite. It is a gas molecular entity and an alkane.

Output: CC


Input: The molecule is a dicarboxylic acid monoester(1-) that is the conjugate base of 6-O-malonyl-trans-rhaponticin, resulting from the deprotonation of the carboxy group. Major microspecies at pH 7.3. It is a conjugate base of a 6-O-malonyl-trans-rhaponticin.

Output: COC1=CC=C(/C=C/C2=CC(O)=CC(O[C@@H]3O[C@H](COC(=O)CC(=O)[O-])[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1O


Input: The molecule is a neolignan isolated from the stems of Sinocalamus affinis. It has a role as a plant metabolite. It is a member of benzofurans, a neolignan, an aldehyde, a primary alcohol, a secondary alcohol and a member of guaiacols.

Output: COC1=CC([C@H](O)[C@@H](CO)OC2=C(OC)C=C([C@@H]3OC4=C(OC)C=C(C=O)C=C4[C@H]3CO)C=C2OC)=CC=C1O


Input: The molecule is an acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate functions of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA; major species at pH 7.3. It is a polyunsaturated fatty acyl-CoA(4-) and a long-chain fatty acyl-CoA(4-). It is a conjugate base of a (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA.

Output: CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]


Input: The molecule is an N-alkylpiperazine that consists of piperazine bearing 2-bis(4-fluorophenyl)methoxy]ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent, competitive inhibitor of dopamine uptake (Ki = 1 nM for inhibition of striatal dopamine uptake). Has > 100-fold lower affinity for the noradrenalin and 5-HT uptake carriers. Also a potent sigma ligand (IC50 = 48 nM). Centrally active following systemic administration. It has a role as a dopamine uptake inhibitor. It is a N-alkylpiperazine, an organofluorine compound, a tertiary amino compound and an ether. It is a conjugate base of a vanoxerine(2+).

Output: FC1=CC=C(C(OCCN2CCN(CCCC3=CC=CC=C3)CC2)C2=CC=C(F)C=C2)C=C1


Input: The molecule is a prostaglandins E. It is functionally related to a prostaglandin E2. It is a conjugate acid of a 15-dehydro-prostaglandin E2(1-).

Output: CCCCCC(=O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O


Input: The molecule is an organonitrogen compound and an organooxygen compound. It is functionally related to a beta-amino acid.

Output: CCOC1=CC=CC=C1CNC(=O)CCNS(=O)(=O)C1=CC=C2NC(=O)OC2=C1


Input: The molecule is a tetrasaccharide derivative with a dimeric structure in which two 2-O-[N-acetyl-alpha-D-glucosaminyl-(1->3)-N-acetyl-alpha-D-glucosaminyl]-D-glyceric acid units are linked via a phosphodiester bridge, the reducing-end GlcNAc residue also being connected at O-6 to a 5-aminopentyl linker via a further phosphodiester linkage. It is a tetrasaccharide derivative and a carbohydrate phosphate. It is functionally related to a D-glyceric acid.


Input: The molecule is a cholestanoid that is 5beta-cholestan-26-al substituted by hydroxy groups at positions 3, 7 and 12 respectively. It has a role as a human metabolite. It is a 3alpha-hydroxy steroid, a 7alpha-hydroxy steroid, a 12alpha-hydroxy steroid, a 26-oxo steroid, a cholestanoid and a steroid aldehyde. It derives from a hydride of a 5beta-cholestane.

Output: CC(C=O)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C


Input: The molecule is a glycodihydroceramide having an alpha-D-glucuronic acid residue at the O-1 position and a tetradecanoyl group attached to the nitrogen. It derives from a D-glucopyranuronic acid.

Output: CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO[C@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O)NC(=O)CCCCCCCCCCCCC


Input: The molecule is a 1-phosphatidyl-1D-myo-inositol in which the phosphatidyl acyl groups at positions 1 and 2 are specified as (13Z,16Z)-docosadienoyl and hexadecanoyl respectively. It has a role as a human metabolite. It is functionally related to a (13Z,16Z)-docosadienoic acid and a hexadecanoic acid.

Output: CCCCC/C=C\C/C=C\CCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC1[C@H](O)[C@H](O)C(O)[C@H](O)[C@H]1O)OC(=O)CCCCCCCCCCCCCCC


Input: The molecule is a triterpenoid. It has a role as a metabolite. It derives from a hydride of a lupane.

Output: C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](OC(=O)/C=C/C6=CC=C(O)C(O)=C6)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12


Input: The molecule is an organic compound derived from pyridine with potassium channel inhibition activity. Amifampridine inhibits potassium channel efflux, increasing the duration of the action potential, which results in an increase in the duration of calcium channel opening and enhanced acetylcholine (ACh) release. Increased ACh availability at the motor end plate allows muscles to contract.

Output: NC1=CC=NC=C1N


Input: The molecule is a docosanoid anion that is the conjugate base of (10R,17S)-dihydroxy-(7Z,11E,13E,15Z,19Z)-docosapentaenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a hydroxy polyunsaturated fatty acid anion and a docosanoid anion. It is a conjugate base of a (10R,17S)-dihydroxy-(7Z,11E,13E,15Z,19Z)-docosapentaenoic acid.

Output: CC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\CCCCCC(=O)[O-]


Input: The molecule is an N-(long-chain-fatty-acyl)-L-glutamic acid in which the acyl group is specified as (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl. It has a role as a marine metabolite. It is functionally related to an all-cis-docosa-4,7,10,13,16,19-hexaenoic acid.

Output: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N[C@@H](CCC(=O)O)C(=O)O


Input: The molecule is a benzopyridoindole derivative with antineoplastic property. Intoplicine inhibits activities of both topoisomerase I and II via intercalating DNA helix, thereby hindering the movements of enzymes along DNA molecules during DNA transcription and replication, respectively. Furthermore, this agent stabilizes DNA-enzyme complexes during unwinding processes by both topoisomerases, leading to double- and single-stranded DNA breaks. Consequently, these effects bring about cell growth inhibition and apoptosis of tumor cells.

Output: CC1=CN=C(NCCCN(C)C)C2=C1NC1=CC=C3C=C(O)C=CC3=C12


Input: The molecule is a dicarboxylic acid dianion resulting from the deprotonation of the two carboxy groups of 5-methyltetrahydrofolic acid; major species at pH 7.3. It is a 5-methyltetrahydrofolate and a dicarboxylic acid dianion. It is functionally related to a 5,6,7,8-tetrahydrofolate(2-). It is a conjugate base of a 5-methyltetrahydrofolic acid.

Output: CN1C2=C(N=C(N)NC2=O)NCC1CNC1=CC=C(C(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-])C=C1


Input: The molecule is a glycosylgalactose consisting of a D-glucopyranose residue and a beta-D-galactopyranose residue joined in sequence by a (1->2) glycosidic bond. It is functionally related to a beta-D-galactose and a D-glucopyranose.

Output: OC[C@H]1O[C@@H](O)[C@H](OC2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H]1O


Input: The molecule is a 2'-deoxyribonucleoside 5'-monophosphate(2-) obtained by deprotonation of the phosphate OH groups of dTMP; major species at pH 7.3. It has a role as a human metabolite. It is a 2'-deoxynucleoside 5'-monophosphate(2-) and a pyrimidine 2'-deoxyribonucleoside 5'-phosphate(2-). It is a conjugate base of a dTMP(-).

Output: CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)([O-])[O-])O2)C(=O)NC1=O


Input: The molecule is dianion of GDP-D-glycero-alpha-D-manno-heptose arising from deprotonation of both free OH groups of the diphosphate. It is a conjugate base of a GDP-D-glycero-alpha-D-manno-heptose.

Output: NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])O[C@H]3O[C@H]([C@H](O)CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1


Input: The molecule is a dual peroxisome proliferator-activated receptor (PPAR) agonist, with hypoglycemic activity. Muraglitazar causes an increase in HDL-C levels, and a decrease in total cholesterol, apolipoprotein B, triglycerides and HbA1c. This agent is associated with an increased risk of adverse cardiovascular events and heart failure.

Output: COC1=CC=C(OC(=O)N(CC(=O)O)CC2=CC=C(OCCC3=C(C)OC(C4=CC=CC=C4)=N3)C=C2)C=C1


Input: The molecule is a cytotoxic anthracycline antibiotic that is produced by Streptomyces peucetius var. carminatus (a biochemical mutant of Streptomyces peucetius var. caesius), and is active against P-388 murine leukemia. It has a role as an antineoplastic agent and a bacterial metabolite. It is an anthracycline antibiotic, an aminoglycoside antibiotic, a member of p-quinones, a member of tetracenequinones and a tertiary alcohol. It is a conjugate base of a 13-deoxycarminomycin(1+). It derives from a hydride of a tetracene.

Output: CC[C@]1(O)CC2=C(O)C3=C(C(=O)C4=C(O)C=CC=C4C3=O)C(O)=C2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1


Input: The molecule is a palladium coordination entity consisting of palladium(II) bound to two chlorine atoms. It has a role as a catalyst.

Output: Cl[Pd]Cl


Input: The molecule is the simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp. It has a role as a photosensitizing agent, an antineoplastic agent, a dermatologic drug, a prodrug, a plant metabolite, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a delta-amino acid and a 4-oxo monocarboxylic acid. It derives from a 4-oxopentanoic acid. It is a conjugate base of a 5-ammoniolevulinic acid. It is a conjugate acid of a 5-aminolevulinate. It is a tautomer of a 5-ammoniolevulinate.

Output: NCC(=O)CCC(=O)O


Input: The molecule is a N-glycosyl-1,2,4-triazine that is 6-azauridine acetylated at positions 2', 3' and 5' on the sugar ring. It is a prodrug for 6-azauridine and is used for treatment of psoriasis. It has a role as an antipsoriatic and a prodrug. It is an acetate ester and a N-glycosyl-1,2,4-triazine. It derives from a 6-azauridine.

Output: CC(=O)OC[C@H]1O[C@@H](N2N=CC(=O)NC2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O


Input: The molecule is a sphingomyelin 36:3 in which the fatty acyl and sphingoid portions are specified as oleoyl and (4E,14Z)-sphingadienine respectively. It is functionally related to an oleic acid and a sphinga-4E,14Z-dienine.

Output: CCC/C=C\CCCCCCCC/C=C/[C@@H](O)[C@H](COP(=O)([O-])OCC[N+](C)(C)C)NC(=O)CCCCCCC/C=C\CCCCCCCC


Input: The molecule is an organic sodium salt that is the disodium salt of 3,3'-azobis(6-hydroxybenzoic acid) (olsalazine). Effective in the treatment of inflammatory bowel disease and ulcerative colitis. Mechanism of action unknown, but appears to be topical It has a role as a non-steroidal anti-inflammatory drug and a prodrug. It contains an olsalazine(2-).

Output: O=C(O)C1=CC(N=NC2=CC=C([O-])C(C(=O)O)=C2)=CC=C1[O-];[Na+];[Na+]


Input: The molecule is a docosanoid anion obtained by deprotonation of the three carboxy groups and protonation of the glutamyl alpha-amino group of (8S)-glutathionyl-(7R,17S)-dihydroxy-(4Z,9,11,13Z,15E,19Z)-docosahexaenoic acid; major species at pH 7.3. It is a docosanoid anion, a peptide anion and a tricarboxylic acid dianion. It is a conjugate base of an (8S)-glutathionyl-(7R,17S)-dihydroxy-(4Z,9,11,13Z,15E,19Z)-docosahexaenoic acid.

Output: CC/C=C\C[C@H](O)/C=C/C=C\C=CC=C[C@H](SC[C@H](NC(=O)CC[C@H]([NH3+])C(=O)[O-])C(=O)NCC(=O)[O-])[C@H](O)C/C=C\CCC(=O)[O-]


Input: The molecule is an orally available inhibitor of extracellular signal-regulated kinase (ERK), with potential antineoplastic activity. Upon oral administration, rineterkib binds to and inhibits ERK, thereby preventing the activation of ERK-mediated signal transduction pathways. This results in the inhibition of ERK-dependent tumor cell proliferation and survival. The mitogen-activated protein kinase (MAPK)/ERK pathway is upregulated in numerous tumor cell types and plays a key role in tumor cell proliferation, differentiation and survival.

Output: CNC[C@@H](NC(=O)C1=CC=C(C2=NC([C@H]3CC[C@H](O)[C@@H](F)C3)=CN=C2N)C=C1F)C1=CC(F)=CC(Br)=C1


Input: The molecule appears as an off-white powdered solid with an aromatic odor. Contact may irritate skin, eyes or mucous membranes. May be toxic by ingestion, inhalation or skin absorption. Used to make other chemicals.

Output: O=S(=O)(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl


Input: The molecule is an (omega-1)-hydroxy fatty acid anion resulting from the deprotonation of the carboxy group of 20-hydroxyhenicosanoic acid. The major species at pH 7.3. It is an (omega-1)-hydroxy fatty acid anion, a long-chain fatty acid anion and a straight-chain saturated fatty acid anion. It derives from a henicosanoate. It is a conjugate base of a 20-hydroxyhenicosanoic acid.

Output: CC(O)CCCCCCCCCCCCCCCCCCC(=O)[O-]


Input: The molecule is any octadecatrienoate having double bonds at positions 9, 11 and 14. It is a conjugate base of a 9,11,14-octadecatrienoic acid.

Output: CCC/C=C/C/C=C/C=C/CCCCCCCC(=O)[O-]


Input: The molecule is an organic anion that is the conjugate base of (4S)-2,3-dehydroleucocyanidin, obtained by deprotonation of the 3-hydroxy group. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.). It is a conjugate base of a (4S)-2,3-dehydroleucocyanidin.

Output: [O-]C1=CC=C(C2=C(O)[C@@H](O)C3=C(O)C=C(O)C=C3O2)C=C1O


Input: The molecule is a purine ribonucleoside 5'-diphosphate having 7-methyl-7,8-dihydroguanine as the nucleobase. It is a conjugate acid of a 7-methyl-7,8-dihydroguanosine-5'-diphosphate(3-).

Output: CN1CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)C2=C1C(=O)NC(N)=N2


Input: The molecule is a phosphatidylcholine O-38:6 in which the alkyl and acyl groups specified at positions 1 and 2 are hexadecyl and (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl respectively. It is a phosphatidylcholine O-38:6 and a 2-acyl-1-alkyl-sn-glycero-3-phosphocholine. It is functionally related to an all-cis-docosa-4,7,10,13,16,19-hexaenoic acid.

Output: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[C@H](COCCCCCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C


Input: The molecule is a hexasaccharide that is verbascose which has an additional unit of alpha-D-galactopyranose attached by a 1->6 glycosidic linkage to the terminal galactosyl residue. It is a hexasaccharide and a raffinose family oligosaccharide. It derives from a verbascose.


Input: The molecule is an N-acyl-D-galactosylsphingosine in which the ceramide N-acyl group is specified as 2-hydroxybehenoyl (2-hydroxydocosanoyl). It is functionally related to a 2-hydroxybehenic acid.

Output: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](COC1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)NC(=O)C(O)CCCCCCCCCCCCCCCCCCCC


Input: The molecule is zwitterionic form of 3-iodo-L-tyrosine having an anionic carboxy group and a protonated amino group; major species at pH 7.3. It is a tautomer of a 3-iodo-L-tyrosine.

Output: [NH3+][C@@H](CC1=CC=C(O)C(I)=C1)C(=O)[O-]


Input: The molecule is a wax ester obtained by the formal condensation of hexadecan-1-ol with oleic acid. It derives from an oleic acid and a hexadecan-1-ol.

Output: CCCCCCCC/C=C\CCCCCCCC(=O)OCCCCCCCCCCCCCCCC


Input: The molecule is the hydroxypolyether that is octaethylene glycol in which one of the hydroxy groups is substituted by dodecyloxy. It is functionally related to an octaethylene glycol.

Output: CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCO


Input: The molecule is a mixture obtained by combining equimolar amounts of hydrogen peroxide and urea. It has a role as an oxidising agent, a reagent and a disinfectant. It contains a hydrogen peroxide and a urea.

Output: NC(N)=O;OO


Input: The molecule is a member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2' and 4', a methoxy group at position 6' and methyl groups at positions 3' and 5'. Isolated from the buds of Cleistocalyx operculatus, it has been shown to exhibit inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2. It has a role as a plant metabolite and an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor. It is a member of chalcones, a monomethoxybenzene and a member of resorcinols. It is functionally related to a trans-chalcone.

Output: COC1=C(C)C(O)=C(C)C(O)=C1C(=O)/C=C/C1=CC=CC=C1


Input: The molecule is a UDP-L-iduronate(2-) in which the anomeric centre of the sugar component has beta-configuration; major species at pH 7.3.

Output: O=C([O-])[C@@H]1O[C@H](OP(=O)([O-])OP(=O)([O-])OC[C@H]2O[C@@H](N3C=CC(=O)NC3=O)[C@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O


Input: The molecule is a primary aliphatic amine that is pentan-3-amine substituted by methyl groups at positions 2 and 4. Metabolite observed in cancer metabolism. It has a role as a human metabolite.

Output: CC(C)C(N)C(C)C


Input: The molecule is zwitterionic form of 6-aminohexanoic acid arising from migration of a proton from the carboxy group to the amino group; major species at pH 7.3. It is a conjugate acid of a 6-aminohexanoate. It is a tautomer of a 6-aminohexanoic acid.

Output: [NH3+]CCCCCC(=O)[O-]


Input: The molecule appears as a clear colorless liquid with a sweet ester odor. Less dense than water. Vapors heavier than air. Eye contact may cause irritation. Frequent or prolonged skin contact may cause irritation and dermatitis. Vapors irritate the eyes and respiratory tract and may cause headaches and dizziness. Vapors are anesthetic and may have other central nervous system effects. Vapors may also cause liver and kidney disorder. Ingestion of the liquid into the respiratory system may cause bronchopneumonia or pulmonary edema.

Output: CC(=O)OCCCCCCC(C)C


Input: The molecule is a 1,2-diacyl-sn-glycero-3-phosphocholine in which the 1- and 2-acyl groups are specified as heptadecanoyl and oleoyl respectively. It is functionally related to an oleic acid and a heptadecanoic acid.

Output: CCCCCCCC/C=C\CCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C


Input: The molecule is a dTDP-sugar having beta-L-daunosamine as the sugar component. It has a role as a bacterial metabolite. It is functionally related to a daunosamine. It is a conjugate acid of a dTDP-beta-L-daunosamine(1-).

Output: CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@@H]3C[C@H](N)[C@H](O)[C@H](C)O3)O2)C(=O)NC1=O


Input: The molecule is a 13-hydroxy-14,15-epoxy-(5Z,8Z,11Z)-icosatrienoate that is the conjugate base of 13(S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-icosatrienoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a conjugate base of a (13S)-hydroxy-(14S,15S)-epoxy-(5Z,8Z,11Z)-icosatrienoic acid.

Output: CCCCC[C@@H]1O[C@H]1[C@@H](O)/C=C\C/C=C\C/C=C\CCCC(=O)[O-]


Input: The molecule is an acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate functions of (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA; major species at pH 7.3. It is a conjugate base of a (4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA.

Output: CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-]


Input: The molecule is an aldehyde that is acetaldehyde substituted by a 5-hydroxyindol-3-yl group. It has a role as a mouse metabolite and a human metabolite. It is a member of hydroxyindoles and an indoleacetaldehyde.

Output: O=CCC1=CNC2=CC=C(O)C=C12


Input: The molecule is a glycerophosphoinositol antigen having a 1-stearoyl-sn-glycero-3-phospho moiety attached at the 6-position of 1D-myo-inositol. It has a role as an antigen. It is a glycerophosphoinositol and a 1-acyl-sn-glycero-3-phospho-D-myo-inositol.

Output: CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)OC1[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]1O


Input: The molecule is a member of the class of leukotrienes that is leukotriene B4 in which the hydroxy group at position 12 has been oxidised to the corresponding ketone and one of the methyl hydrogens at position 20 replaced by a hydroxy group. It is a leukotriene, a long-chain fatty acid, a secondary alcohol, a primary alcohol, an oxo fatty acid and a hydroxy polyunsaturated fatty acid. It derives from a leukotriene B4. It is a conjugate acid of a 12-oxo-20-hydroxyleukotriene B4(1-).

Output: O=C(O)CCC[C@H](O)/C=C\C=C\C=C\C(=O)C/C=C\CCCCCO


Input: The molecule is a C-glycosyl compound that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 6, a methoxy group at position 5 and a beta-D-glucopyranosyl residue at position 1 via a C-glycosyl linkage. It has a role as a plant metabolite. It is a member of xanthones, a C-glycosyl compound, a polyphenol and an aromatic ether.

Output: COC1=C(O)C=CC2=C1OC1=CC(O)=C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(O)=C1C2=O


Input: The molecule is a substituted aniline that is a benzene ring substituted with an amino group at position 1 and a trifluoromethyl group at position 4. It has a role as a metabolite. It is a substituted aniline and a member of (trifluoromethyl)benzenes.

Output: NC1=CC=C(C(F)(F)F)C=C1


Input: The molecule is a nitrogen mustard drug indicated for use in the treatment of chronic lymphocytic leukemia (CLL) and indolent B-cell non-Hodgkin lymphoma (NHL) that has progressed during or within six months of treatment with rituximab or a rituximab-containing regimen.  Bendamustine is a bifunctional mechlorethamine derivative capable of forming electrophilic alkyl groups that covalently bond to other molecules. Through this function as an alkylating agent, bendamustine causes intra- and inter-strand crosslinks between DNA bases resulting in cell death.  It is active against both active and quiescent cells, although the exact mechanism of action is unknown.

Output: CN1C(CCCC(=O)O)=NC2=CC(N(CCCl)CCCl)=CC=C21


Input: The molecule is a dihydroxybenzoate that is the conjugate base of cannabigerolic acid, obtained by deprotonation of the carboxy group. It is functionally related to an olivetolate. It is a conjugate base of a cannabigerolic acid.

Output: CCCCCC1=CC(O)=C(C/C=C(\C)CCC=C(C)C)C([O-])=C1C(=O)O


Input: The molecule is a trihydroxyflavone that is flavone substituted by hydroxy groups at positioms 5, 6 and 3' and methoxy groups at positions 3, 7 and 4' respectively. It has a role as a plant metabolite. It is a trihydroxyflavone and a trimethoxyflavone. It derives from a flavone.

Output: COC1=CC=C(C2=C(OC)C(=O)C3=C(O)C(O)=C(OC)C=C3O2)C=C1O


Input: The molecule is under investigation in clinical trial NCT03425539 (Efficacy and Safety of Lucerastat Oral Monotherapy in Adult Subjects With Fabry Disease).

Output: CCCCN1C[C@H](O)[C@@H](O)[C@@H](O)[C@H]1CO


Input: The molecule is a pyridinium ion obtained by protonation of the ring nitrogen of pyridoxal. It is a pyridinium ion and a vitamin B6. It is a conjugate acid of a pyridoxal.

Output: CC1=[NH+]C=C(CO)C(C=O)=C1O


Input: The molecule is a bile acid anion and a cholanic acid anion. It has a role as a human metabolite. It is a conjugate base of a deoxycholic acid.

Output: C[C@H](CCC(=O)[O-])[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C


Input: The molecule is a dipeptide formed from L-tryptophan and L-alanine residues. It has a role as a metabolite. It is functionally related to a L-tryptophan and a L-alanine.

Output: C[C@H](NC(=O)[C@@H](N)CC1=CNC2=CC=CC=C12)C(=O)O


Input: The molecule is a tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-methoxyphenyl group. It has a role as an antidepressant, a serotonin uptake inhibitor, an adrenergic uptake inhibitor, a dopamine uptake inhibitor, an analgesic, an environmental contaminant and a xenobiotic. It is a member of cyclohexanols, a tertiary alcohol, a tertiary amino compound and a monomethoxybenzene.

Output: COC1=CC=C(C(CN(C)C)C2(O)CCCCC2)C=C1


Input: The molecule is an N-acyl-1-O-beta-D-glucosyl-15-methylhexadecasphing-4-enine in which the acyl group has 24 carbons and 0 double bonds. It derives from a 15-methylhexadecasphing-4-enine.

Output: CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)/C=C/CCCCCCCCCC(C)C


Input: The molecule is the (S)-enantiomer of fluoxytioconazole (thiol). It is an enantiomer of a (R)-fluoxytioconazole (thiol). It is a tautomer of a (S)-fluoxytioconazole (thione).

Output: N#CC1=CC=C(OC2=CC=C(C(F)(F)[C@@](O)(CN3NC=NC3=S)C3=CC=C(F)C=C3F)N=C2)C=C1


Input: The molecule is an alicyclic ketone that is oxocyclopentanone substituted at position 3 by a carboxy group. It is a 4-oxo monocarboxylic acid and an alicyclic ketone. It is a conjugate acid of a 3-oxocyclopentanecarboxylate.

Output: O=C1CCC(C(=O)O)C1


Input: The molecule is a dTDP-sugar having 4-dehydro-6-deoxy-beta-D-gulose as the sugar component. It is a conjugate acid of a dTDP-4-dehydro-6-deoxy-beta-D-gulose(2-).

Output: CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@@H]3O[C@H](C)C(=O)[C@@H](O)[C@H]3O)O2)C(=O)NC1=O


Input: The molecule is a 6-hydroxynicotine. It is functionally related to a (S)-nicotine. It is a conjugate base of a (S)-6-hydroxynicotinium(1+). It is an enantiomer of a (R)-6-hydroxynicotine.

Output: CN1CCC[C@H]1C1=CNC(=O)C=C1


Input: The molecule is an organic cation that is phenothiazin-5-ium substituted by dimethylamino and amino groups at positions 3 and 7 respectively. The chloride salt is the histological dye 'azure B'.

Output: CNC1=CC=C2N=C3C=CC(=[N+](C)C)C=C3SC2=C1


Input: The molecule is a diester. It is functionally related to a trichloroacetic acid and an ethylene glycol.

Output: O=C(OCCOC(=O)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl


Input: The molecule is a tertiary ammonium ion that is the conjugate acid of lanperisone resulting from the protonation of the pyrrolidine nitrogen. Major microspecies at pH 7.3. It is a conjugate acid of a lanperisone.

Output: C[C@H](C[NH+]1CCCC1)C(=O)C1=CC=C(C(F)(F)F)C=C1


Input: The molecule is an omega-hydroxy fatty acid ascaroside that is oscr#34 in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group. It is a metabolite of the nematode Caenorhabditis elegans. It has a role as a Caenorhabditis elegans metabolite. It is an omega-hydroxy fatty acid ascaroside, a 3-hydroxy carboxylic acid and a monocarboxylic acid. It is functionally related to an oscr#34 and a (3R)-3,19-dihydroxynonadecanoic acid. It is a conjugate acid of a bhos#34(1-).

Output: C[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1O


Input: The molecule is a sedoheptulose derivative and a ketoheptose phosphate. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a sedoheptulose. It is a conjugate acid of a sedoheptulose 1,7-bisphosphate(4-).

Output: O=C(COP(=O)(O)O)[C@@H](O)[C@H](O)[C@H](O)[C@H](O)COP(=O)(O)O