Input: The molecule is a carbamate ester. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide and an agrochemical. It derives from a methylcarbamic acid and a 3,4-xylenol.

Output: CNC(=O)OC1=CC=C(C)C(C)=C1


Input: The molecule is a bile acid salt that is the sodium salt of glycochenodeoxycholic acid. It has a role as a human metabolite. It is an organic sodium salt and a bile acid salt. It contains a glycochenodeoxycholate.

Output: C[C@H](CCC(=O)NCC(=O)[O-])[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]3CC[C@]12C;[Na+]


Input: The molecule is a dihydroxy monocarboxylic acid that is tricosanoic acid in which the pro-R hydrogens at positions 3 and 22 are replaced by hydroxy groups. It is a very long-chain fatty acid, an (omega-1)-hydroxy fatty acid, a 3-hydroxy carboxylic acid and a dihydroxy monocarboxylic acid. It is functionally related to a tricosanoic acid.

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


Input: The molecule is an amino hexasaccharide made up of three units of alpha-D-Galp-(1->4)-alpha-D-NeupAc, joined together by glycosidic linkages between position 2 of the N-acetylneuraminyl residues and position 6 of the galactosyl residues.


Input: The molecule is a hydroxyeicosatrienoic acid that consists of 6E,8Z,11Z-eicosatrienoic acid bearing a 5-hydroxy substituent. It has a role as a metabolite. It is functionally related to a (5Z,8Z,11Z)-icosatrienoic acid.

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


Input: The molecule is a hexanone that is hexan-3-one substituted by a hydroxy group at position 4. It is a secondary alcohol, a secondary alpha-hydroxy ketone and a hexanone.

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


Input: The molecule is a 2-hydroxy fatty acid anion that is the conjugate base of 2-hydroxyhexacosanoic acid (2-hydroxycerotic acid), obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a very long-chain fatty acid anion and a 2-hydroxy fatty acid anion 26:0. It is functionally related to a cerotate. It is a conjugate base of a 2-hydroxyhexacosanoic acid.

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


Input: The molecule is an oligosaccharide consisting of deamino-alpha-neuraminyl residues linked (2->8) (degree of polymerisation = 2--7; average degree of polymerisation ~ 3). It derives from a deamino-alpha-neuraminic acid.

Output: O=C(O)[C@@]1(O[C@H](CO)[C@@H](O)[C@@H]2O[C@@](O)(C(=O)O)C[C@H](O)[C@H]2O)C[C@H](O)[C@@H](O)[C@H]([C@H](O)[C@@H](CO)O[C@]2(C(=O)O)C[C@H](O)[C@@H](O)[C@H]([C@H](O)[C@H](O)CO)O2)O1


Input: The molecule is a member of the class of oxazolidinones that is oxazolidin-2-one substituted at positions 3, 4 and 5 by 3-(isoquinolin-4-yl)propanoyl, methyl and 3,5-bis(trifluoromethyl)phenyl groups respectively. An inhibitor of teichoic acid biosynthesis. It has a role as a teichoic acid biosynthesis inhibitor. It is a member of (trifluoromethyl)benzenes, a carbamate ester, a dicarboximide, an oxazolidinone and a member of isoquinolines. It derives from an oxazolidin-2-one.

Output: C[C@H]1[C@@H](C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)OC(=O)N1C(=O)CCC1=CN=CC2=CC=CC=C12


Input: The molecule appears as a colorless to light yellow or brown liquid. Combustible. Toxic by inhalation and by skin absorption. Produces toxic oxides of nitrogen during combustion.

Output: CN1CCCC1C1=CC=CN=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 derives from an androstane.

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


Input: The molecule is a dipeptide formed from two L-asparagine units. It has a role as a Mycoplasma genitalium metabolite. It derives from a L-asparagine.

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


Input: The molecule is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate.

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


Input:
The molecule is found in milk and milk products. Roquefortine is a metabolite of Penicillium roquefortii, Penicillium commune, Penicillium cyclopium, Penicillium farinosum and many other Penicillium species Common constituent of blue cheese

Roquefortine belongs to the family of Pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole.

Output: C=CC(C)(C)[C@@]12C[C@H]3C(=O)N/C(=C\C4=CN=CN4)C(=O)N3[C@@H]1NC1=CC=CC=C12


Input: The molecule is 7-Hydroxyisoflavone with additional hydroxy groups at positions 5 and 4'. It is a phytoestrogenic isoflavone with antioxidant properties. It has a role as an antineoplastic agent, a tyrosine kinase inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, a phytoestrogen and a plant metabolite. It is a conjugate acid of a genistein(1-).

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


Input: The molecule is trianion of 2-cis,6-trans-farnesyl diphosphate arising from deprotonation of the diphosphate OH groups; major species at pH 7.3. It is a conjugate base of a 2-cis,6-trans-farnesyl diphosphate.

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


Input: The molecule is an acylCoA(4-) that is the tetraanion of N-methylanthraniloyl-CoA, arising from deprotonation of the phosphate and diphosphate OH groups. It is a conjugate base of a N-methylanthraniloyl-CoA.

Output: CNC1=CC=CC=C1C(=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 docosanoid anion that is the conjugate base of resolvin T3, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a hydroxy fatty acid anion and a docosanoid anion. It is a conjugate base of a resolvin T3.

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


Input: The molecule is a carbohydrate acid derivative anion in which the anionic species formed by proton loss from the carboxy function of beta-D-galacturonic acid is linked glycosidically to a 3-aminopropyl group. It is a conjugate base of a 3-aminopropyl beta-D-galactopyranosiduronic acid.

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


Input: The molecule is an artemoin in which the two hydroxy groups on the C-30 side-chain are located at positions 19 and 20. It has a role as a mouse metabolite, a plant metabolite and a rat metabolite.


Input: The molecule is under investigation in clinical trial NCT03892499 (A Trial to Evaluate the Effect of Itraconazole (ITZ), a CYP3A4 Inhibitor, on the Pharmacokinetics of the Soluble Guanylate Cyclase Stimulator, Olinciguat (IW-1701), in Healthy Volunteers).

Output: NC(=O)[C@](O)(CNC1=NC(C2=NN(CC3=CC=CC=C3F)C(C3=NOC=C3)=C2)=NC=C1F)C(F)(F)F


Input: The molecule is a 1-benzyl-2-methyl-1,2,3,4-tetrahydroisoquinoline. It is an enantiomer of a (R)-1-benzyl-2-methyl-1,2,3,4-tetrahydroisoquinoline.

Output: CN1CCC2=CC=CC=C2[C@@H]1CC1=CC=CC=C1


Input: The molecule is a triglyceride in which the 1- and 3-acyl groups are palmitoyl while that at position 2 is oleoyl. It derives from an oleic acid and a hexadecanoic acid.

Output: CCCCCCCC/C=C\CCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC


Input: The molecule is an anti-aphthous ulcer drug. Amlexanox inhibits the synthesis and release of inflammatory mediators, including leukotrienes and histamine, from mast cells, neutrophils, and mononuclear cells. Amlexanox also acts as a leukotriene D4 antagonist and a phosphodiesterase inhibitor. Amlexanox decreases the time ulcers take to heal as well as the pain associated with the ulcers.

Output: CC(C)C1=CC=C2OC3=NC(N)=C(C(=O)O)C=C3C(=O)C2=C1


Input: The molecule is an orally bioavailable antagonist of both the immunomodulatory checkpoint molecules adenosine A2A receptor (A2AR; ADORA2A) and A2B receptor (A2BR; ADORA2B), with potential immunomodulating and antineoplastic activities. Upon administration, etrumadenant competes with tumor-released adenosine for binding to A2AR and A2BR expressed on numerous intra-tumoral immune cells, such as dendritic cells (DCs), natural killer (NK) cells, macrophages and T-lymphocytes. The binding of AB928 to A2AR and A2BR inhibits A2AR/A2BR activity and prevents adenosine-A2AR/A2BR-mediated signaling. A2AR/A2BR inhibition activates and enhances the proliferation of various immune cells, abrogates the adenosine-mediated immunosuppression in the tumor microenvironment (TME) and activates the immune system to exert anti-tumor immune responses against cancer cells, which leads to tumor cell killing. A2AR and A2BR, G protein-coupled signaling receptors, are expressed on the cell surfaces of numerous immune cells. Adenosine is often overproduced by tumor cells and plays a key role in immunosuppression and tumor cell proliferation.

Output: CC1=C(C#N)C=CC=C1C1=CC(C2=CN(CC3=CC=CC(C(C)(C)O)=N3)N=N2)=NC(N)=N1


Input: The molecule is a selective serotonin agonist that was used as a weight loss agent. Lorcaserin was in clinical use for eight years when it was withdrawn because of concerns regarding an excess in cancer risk after long term use. In prelicensure studies and while in clinical use, lorcaserin was not found to be associated with serum enzyme elevations during therapy or to instances of clinically apparent liver injury.

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


Input: The molecule is a selective inhibitor of phosphodiesterase-4 (PDE-4) that has unique antiinflammatory activity and is used to treat and prevent exacerbations of chronic obstructive pulmonary disease (COPD). Roflumilast has not been linked to significant serum enzyme elevations during therapy or to instances of clinically apparent acute liver injury.

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


Input: The molecule is an aryloxypyrimidine having a 4,6-diphenoxypyrimidine skeleton in which one of the phenyl rings is cyano-substituted at C-2 and the other carries a 1-carboxy-2-methoxyethenyl substituent, also at C-2. It is a metabolite of the fungicidal agrochemical azoxystrobin. It has a role as a marine xenobiotic metabolite. It is an aromatic ether, an aryloxypyrimidine, an enol ether and a nitrile.

Output: CO/C=C(/C(=O)O)C1=CC=CC=C1OC1=CC(OC2=CC=CC=C2C#N)=NC=N1


Input: The molecule is an indole alkaloid having a ajmalan-type skeleton and characterised by a 17alpha-acetoxy group, a 21beta-methyl group, loss of the 1-methyl group with associated unsaturation at N(1)=C(2), and a 20alpha-hydroxymethyl group in place of the 20beta-ethyl side-chain. It derives from a hydride of an ajmalan.

Output: CC(=O)O[C@@H]1C2[C@H]3C[C@H]4C5=NC6=CC=CC=C6[C@]51C[C@@H]2N4[C@@H](C)[C@@H]3CO


Input: The molecule is a fourteen-membered macrocyclic diterpene consisting of 1,5,9-trimethyl-12-(prop-1-en-2-yl)cyclotetradecane having three endocyclic double bonds located at positions 1, 5 and 9. It has a role as a bacterial metabolite, a coral metabolite and an animal metabolite. It is a cycloalkatriene, a diterpene and a macrocycle. It derives from a hydride of a cembrane.

Output: C=C(C)[C@H]1C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC1


Input: The molecule is a triterpene glycoside obtained from the New Zealand and South Australian sea cucumber Australostichopus mollis. It has a role as a marine metabolite. It is a triterpenoid saponin, a pentacyclic triterpenoid, a tetrasaccharide derivative, an oligosaccharide sulfate, a lactone, a ketone and an olefinic compound. It derives from a hydride of a lanostane.


Input: The molecule is a 1,2-diacyl-sn-glycero-3-phosphoethanolamine in which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl) and 11Z-octadecenoyl respectively. It has a role as a mouse metabolite. It is functionally related to a cis-vaccenic acid and a hexadecanoic acid.

Output: CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN


Input: The molecule is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals.

Output: NCCC1=CC=C(O)C=C1


Input: The molecule is a prostaglandin J derivative comprising prostaglandin J3 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions. An intermediate of specialised proresolving mediators It has a role as a human xenobiotic metabolite and a mouse metabolite. It is a conjugate acid of a 15-deoxy-Delta(12,14)-prostaglandin J3(1-).

Output: CC/C=C\C/C=C/C=C1/C(=O)C=C[C@@H]1C/C=C\CCCC(=O)O


Input: The molecule is a pentacyclic triterpenoid that is olean-18-ene substituted at position 3 by an oxo group and position 28 by a carboxy group. It has a role as a metabolite, an anti-HSV-1 agent and an anti-HIV agent. It derives from a hydride of an oleanane.

Output: CC1(C)C=C2[C@H]3CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@@]2(C(=O)O)CC1


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

Output: CCCCCCCCCCC(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 member of the class of benzoic acids that is benzoic acid substituted by (4,6-dimethoxypyrimidin-2-yl)oxy groups at positions 2 and 6. Its sodium salt is used as a broad spectrum post emergent herbicide for the control of grasses, sedges and broadleaf weeds in rice crops. It has a role as a herbicide. It is an aromatic ether, a member of pyrimidines, a member of benzoic acids and a monocarboxylic acid. It is a conjugate acid of a bispyribac(1-).

Output: COC1=CC(OC)=NC(OC2=CC=CC(OC3=NC(OC)=CC(OC)=N3)=C2C(=O)O)=N1


Input: The molecule is a secondary ammonium ion that is the conjugate acid of aculene A, arising from the protonation of the pyrrolidine nitrogen. Major species at pH 7.3. It is a conjugate acid of an aculene A.

Output: CCC1=CC(=O)[C@]2(C)C1=CC=C(C)C[C@@H]2OC(=O)[C@@H]1CCC[NH2+]1


Input: The molecule is an anionic phospholipid that is the conjugate base of phosphomycoketide C32 obtained by deprotonation of the phosphate OH groups; major species at pH 7.3. It is a conjugate base of a phosphomycoketide C32.

Output: CCCCCCC[C@H](C)CCC[C@H](C)CCC[C@H](C)CCC[C@H](C)CCC[C@H](C)CCCOP(=O)([O-])[O-]


Input: The molecule is under investigation in clinical trial NCT00827190 (Study Evaluating Single Ascending Doses Of ILS-920).


Input: The molecule is an indole alkaloid that is canthin-6-one substituted by a hydroxy group at position 10. Isolated from Simaba multiflora, it exhibits antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is an indole alkaloid and an organic heterotetracyclic compound. It is functionally related to a canthin-6-one.

Output: O=C1C=CC2=C3C(=CC=N2)C2=CC(O)=CC=C2N13


Input: The molecule is a member of the class of tetramic acids that is trichosetin in which the hydrogen attached to the lactam nitrogen has been replaced by a methyl group. It is produced by the filamentous fungus Fusarium heterosporum. It has a role as an antibacterial agent, a quorum sensing inhibitor, a HIV-1 integrase inhibitor and a fungal metabolite. It is an enol, a member of octahydronaphthalenes, a primary alcohol and a member of tetramic acids. It is functionally related to a trichosetin. It is a conjugate acid of an equisetin(1-).

Output: C/C=C/[C@@H]1C=C[C@@H]2C[C@H](C)CC[C@H]2[C@]1(C)/C(O)=C1\C(=O)[C@H](CO)N(C)C1=O


Input: The molecule is an organic heterotricyclic compound that is 9,10-dihydroxy-1H-benzo[g]isochromen-1-one substituted at positions 3 and 7 by methyl and methoxy groups respectively. It has a role as a plant metabolite. It is an organic heterotricyclic compound, a lactone, a member of phenols, an aromatic ether, a polyketide and a naphtho-alpha-pyrone. It is functionally related to a nor-toralactone.

Output: COC1=CC(O)=C2C(O)=C3C(=O)OC(C)=CC3=CC2=C1


Input: The molecule is an orally available inhibitor of maternal embryonic leucine zipper kinase (MELK) with potential antineoplastic activity. Upon administration, OTS167 binds to MELK, which prevents both MELK phosphorylation and activation; thus inhibiting the phosphorylation of downstream MELK substrates. This may lead to an inhibition of both cell proliferation and survival in MELK-expressing tumor cells. MELK, a serine/threonine kinase, is involved in cancer cell survival, invasiveness and cancer-stem cell formation and maintenance; it is highly upregulated in various types of cancer cells and absent in normal, healthy cells.

Output: CC(=O)C1=CN=C2C=CC(C3=CC(Cl)=C(O)C(Cl)=C3)=NC2=C1NC1CCC(CN(C)C)CC1


Input: The molecule is a monohydroxypyridine that is picolinic acid in which the hydrogen at position 3 is replaced by a hydroxy group. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of oligonucleotides. It has a role as a MALDI matrix material. It is a monohydroxypyridine and a monocarboxylic acid.

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


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 is functionally related to 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 a 1,2-diacyl-sn-glycero-3-phosphocholine in which the 1- and 2-acyl groups are specified as heptadecanoyl and oleoyl respectively. It derives from 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 member of the class of 7-hydroxyisoflavones that is 2',2'-dimethyl-2'H,4H-3,6'-bichromen-4-one substituted by hydroxy groups at positions 5, 7 and 8'. It has been isolated from Glycyrrhiza uralensis. It has a role as a plant metabolite and an EC 1.1.1.21 (aldehyde reductase) inhibitor.

Output: CC1(C)C=CC2=CC(C3=COC4=CC(O)=CC(O)=C4C3=O)=CC(O)=C2O1


Input: The molecule is a (R*,R*)-diepoxybutane. It is an enantiomer of a (S,S)-diepoxybutane.

Output: C1O[C@H]1[C@H]1CO1


Input: The molecule is a zwitterionic form of N(6),N(6),N(6)-trimethyl-L-lysinium cation arising from transfer of a proton from the carboxy to the amino group; major species at pH 7.3 It is a tautomer of a N(6),N(6),N(6)-trimethyl-L-lysine.

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


Input: The molecule is a member of the class of hydroxylamines that is L-ornithine in which one of the N(5)-amino hydrogens is replaced by a hydroxy group. It is a L-ornithine derivative, a member of hydroxylamines and a non-proteinogenic alpha-amino acid. It is a tautomer of a N(5)-hydroxy-L-ornithine zwitterion.

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


Input: The molecule is a member of the class of furans that is furan which is substituted by aminomethyl and pyridy-3-yl groups at positions 2 and 5 respectively. It is a member of furans and a member of pyridines.

Output: NCC1=CC=C(C2=CC=CN=C2)O1


Input: The molecule is an inhibitor of neuronal activity used for therapy of painful neuropathy and as an anticonvulsant. Therapy with pregabalin is not associated with serum aminotransferase elevations, and clinically apparent liver injury from pregabalin has been reported but appears to be quite rare.

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


Input: The molecule is a cardiolipin in which all four phosphatidyl acyl groups are specified as linoleoyl. It is functionally related to a linoleic acid. It is a conjugate acid of a tetralinoleoyl cardiolipin(2-).

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


Input: The molecule is a serotonin and norepinephrine reuptake inhibitor widely used as an antidepressant. Venlafaxine therapy can be associated with transient asymptomatic elevations in serum aminotransferase levels and has been linked to rare instances of clinically apparent acute liver injury.

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


Input: The molecule is a member of formamides and a formamidopyrimidine. It is functionally related to a formamide.

Output: O=CNC1=CN=CN=C1


Input: The molecule is an organic radical derived from ethane. It derives from a hydride of an ethane.

Output: CC


Input: The molecule is a fatty acid ester obtained by the formal condensation of (S)-2-methylbutyric acid with egonol. It has been isolated from the fruits of Styrax agrestis. It has a role as a plant metabolite. It is a member of 1-benzofurans, a member of benzodioxoles, a fatty acid ester and an aromatic ether. It derives from a (S)-2-methylbutyric acid and an egonol. It derives from a hydride of a 1-benzofuran.

Output: CC[C@H](C)C(=O)OCCCC1=CC(OC)=C2OC(C3=CC=C4OCOC4=C3)=CC2=C1


Input: The molecule is a retinoid anion that is the conjugate base of all-trans-13,14-dihydroretinoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a retinoid anion and a monocarboxylic acid anion. It is a conjugate base of an all-trans-13,14-dihydroretinoic acid.

Output: CC1=C(/C=C/C(C)=C/C=C/C(C)CC(=O)[O-])C(C)(C)CCC1


Input: The molecule is a 3-hydroxytetracosanoyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of (3S)-hydroxytetracoscanoyl-CoA; major species at pH 7.3. It is a conjugate base of a (3S)-3-hydroxytetracosanoyl-CoA.

Output: CCCCCCCCCCCCCCCCCCCCC[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 an anticonvulsant drug used in the treatment of epilepsy. In particular, in the adult patient population, it can be employed to treat partial seizures (with and without generalization). Alternatively, it is used to treat partial and generalized seizures associated with Lennox-Gastaut syndrome in children. It has a weak inhibitory effect on GABA receptor binding sites.

Output: NC(=O)OCC(COC(N)=O)C1=CC=CC=C1


Input: The molecule is a lipophilic dihydropyridine calcium antagonist with an intrinsically slow onset of activity. Due to its long duration of action, lacidipine does not lead to reflex tachycardia. It displays specificity in the vascular smooth muscle, where it acts as an antihypertensive agent to dilate peripheral arterioles and reduce blood pressure. Compared to other dihydropyridine calcium antagonists, lacidipine exhibits a greater antioxidant activity which may confer potentially beneficial antiatherosclerotic effects. Lacidipine is a highly lipophilic molecule that interacts with the biological membranes. Through radiotracer analysis, it was determined that lacidipine displays a high membrane partition coefficient leading to accumulation of the drug in the membrane and slow rate of membrane washout. When visualized by small-angle X-ray diffraction with angstrom resolution to examine its location within the membranes, lacidipine was found deep within the membrane's hydrocarbon core. These results may explain the long clinical half-life of lacidipine.   In randomised, well-controlled trials, administration of daily single-dose lacidipine ranging from 2-6 mg demonstrated comparable antihypertensive efficacy similar to that of other long-acting dihydropyridine calcium antagonists, thiazide diuretics, atenolol (a beta-blocker) and enalapril (an ACE inhibitor). It is available as once-daily oral tablets containing 2 or 4 mg of the active compound commonly marketed as Lacipil or Motens. It is not currently FDA-approved.

Output: CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1/C=C/C(=O)OC(C)(C)C


Input: The molecule is a dipeptide formed from two L-asparagine units. It has a role as a Mycoplasma genitalium metabolite. It is functionally related to a L-asparagine.

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


Input: The molecule is a methyl-branched fatty acid that is triacontanoic acid (melissic acid) substituted by a methyl group at position 28. It is a branched-chain saturated fatty acid, a methyl-branched fatty acid and an ultra-long-chain fatty acid. It derives from a triacontanoic acid.

Output: CCC(C)CCCCCCCCCCCCCCCCCCCCCCCCCCC(=O)O


Input: The molecule is a monocarboxylic acid anion. It is functionally related to a costunolide.

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


Input: The molecule is a third-generation cephalosporin with antibacterial activity. Cefdaloxime binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Output: COCC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)/C(=N\O)C3=CSC(N)=N3)[C@H]2SC1


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 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 member of the class of cinnolines that is 6,7-methylenedioxycinnolin-4(1H)-one bearing an ethyl group at position 1 and a carboxylic acid group at position 3. An analogue of oxolinic acid, it has similar antibacterial actions. It was formerly used for the treatment of urinary tract infections. It has a role as an antibacterial drug and an antiinfective agent. It is a member of cinnolines, an oxo carboxylic acid and an oxacycle.

Output: CCN1N=C(C(=O)O)C(=O)C2=CC3=C(C=C21)OCO3


Input: The molecule is an isochromene. It is a tautomer of a 1H-isochromene.

Output: C1=C2C=CC=CC2=COC1


Input: The molecule is a 2'-deoxyribonucleoside 5'-diphosphate obtained by deprotonation of the diphosphate OH groups of 2'-deoxycytidine 5'-diphosphate (dCDP). It has a role as a human metabolite and a Saccharomyces cerevisiae metabolite. It is a conjugate base of a dCDP.

Output: NC1=NC(=O)N([C@H]2C[C@H](O)[C@@H](COP(=O)([O-])OP(=O)([O-])[O-])O2)C=C1


Input: The molecule is https://www.chemicalbook.com/ProductChemicalPropertiesCB9738874_EN.htm It has a role as a glycine receptor antagonist.

Output: COC1=CC(=O)OC(/C=C/C2=CC=CC=C2)C1


Input: The molecule is a monohydroxypyridine and a member of methylpyridines. It is functionally related to a cinchomeronic acid. It is a conjugate acid of a 5-hydroxy-6-methylpyridine-3,4-dicarboxylate and a 5-oxido-6-methylpyridinium-3,4-dicarboxylate.

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


Input: The molecule is a 1,2-diacyl-sn-glycero-3-phosphoethanolamine in which the 1- and 2-acyl groups are specified as hexadecanoyl (palmitoyl) and 11Z-octadecenoyl respectively. It has a role as a mouse metabolite. It derives from a cis-vaccenic acid and a hexadecanoic acid.

Output: CCCCCC/C=C\CCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)(O)OCCN


Input: The molecule is a phosphinamidine. It is functionally related to a P,P-diphenylphosphinimidic amide.

Output: C1=CC=C(N=P(NC2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1


Input: The molecule is a transition element with the chemical symbol Cr and atomic number 24 that belongs to Group 6 of the periodic table. It is used in various chemical, industrial and manufacturing applications such as wood preservation and metallurgy. The uses of chromium compounds depend on the valency of chromium, where trivalent Cr (III) compounds are used for dietary Cr supplementation and hexavalent Cr (VI) compounds are used as corrosion inhibitors in commercial settings and are known to be human carcinogens. Humans can be exposed to chromium via ingestion, inhalation, and dermal or ocular exposure. Trivalent chromium (Cr(III)) ion is considered to be an essential dietary trace element as it is involved in metabolism of blood glucose, regulation of insulin resistance and metabolism of lipids. Clinical trials and other studies suggest the evidence of chromium intake improving glucose tolerance in patients with Type I and II diabetes, however its clinical application in the standard management of type II diabetes mellitus is not established. Chromium deficiency has been associated with a diabetic-like state, impaired growth, decreased fertility and increased risk of cardiovascular diseases.  According to the National Institute of Health, the daily dietary reference intake (DRI) of chromium for adult male and non-pregnant female are 35 μg and 25 μg, respectively. Chromium picolinate capsules may be used as nutritional adjuvant in patients with or at risk of type 2 diabetes mellitus (T2DM) to improve blood sugar metabolism and stabilize the levels of serum cholesterol. Chromium chloride is available as an intravenous injection for use as a supplement to intravenous solutions given for total parenteral nutrition (TPN).

Output: [Cr]


Input: The molecule is under investigation in clinical trial NCT02350426 (A Study to Assess Inflammation in Rheumatoid Arthritis Using Molecular Imaging Techniques).

Output: CCN(CC)C(=O)[C@H]1CCCC2=C1C1=C(OC)C=CC=C1N2CCF


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 derives from 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 cyclitol phosphate that is validone carrying a single monophosphate substituent at position 7. It is a cyclitol phosphate, a triol and a hydroxycyclohexanone. It is functionally related to a validone. It is a conjugate acid of a validone 7-phosphate(2-).

Output: O=C1C[C@H](COP(=O)(O)O)[C@@H](O)[C@H](O)[C@H]1O


Input: The molecule is an acetate ester formed by total acetylation of gentiobiose. It is an acetate ester and a disaccharide.

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


Input: The molecule is an organic cation obtained by protonation at position 3 in the oxazole ring of indolmycin. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.). It is a conjugate acid of an indolmycin.

Output: C[NH+]=C1NC(=O)[C@H]([C@H](C)C2=CNC3=CC=CC=C23)O1


Input: The molecule is the amino hexadecasaccharide obtained when four molecules of the repeating tetrasacchride unit from Shigella dysenteriae O-specific polysaccharide are joined via alpha-(1->3) linkages. It has a role as a hapten.


Input: The molecule is a member of the class of indoles that is 6-hydroxyindole in which the phenolic hydrogen has been replaced by a sulfo group. It is an aryl sulfate and a member of indoles. It is a conjugate acid of a 6-hydroxyindole sulfate(1-).

Output: O=S(=O)(O)OC1=CC=C2C=CNC2=C1


Input: The molecule is the (2S,3R)-stereoisomer of 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol. It is an enantiomer of a (2R,3S)-cyproconazole.

Output: C[C@H](C1CC1)[C@@](O)(CN1C=NC=N1)C1=CC=C(Cl)C=C1


Input: The molecule is a dicarboxylate resulting from deprotonation of both carboxy groups of kainic acid, and protonation of its amine group. Major species at pH 7.3. It is a conjugate base of a kainic acid.

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


Input: The molecule is a 2-monoglyceride where the acyl group is dodecanoyl (lauroyl). It is a 2-monoglyceride and a dodecanoate ester.

Output: CCCCCCCCCCCC(=O)OC(CO)CO


Input: The molecule is a purine nucleoside in which guanine is attached to ribofuranose via a beta-N(9)-glycosidic bond. It has a role as a fundamental metabolite. It is a purines D-ribonucleoside and a member of guanosines. It is functionally related to a guanine.

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


Input: The molecule is conjugate base of (R)-beta-alanopine. It is a conjugate base of a (R)-beta-alanopine.

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


Input: The molecule is an organosulfate oxoanion that is the conjugate base of 2-butyloctyl hydrogen sulfate, obtained by deprotonation of the sulfate group. Major microspecies at pH 7.3. It is a conjugate base of a 2-butyloctyl hydrogen sulfate.

Output: CCCCCCC(CCCC)COS(=O)(=O)[O-]


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

Output: CCN(CC)[C@H](C)C(=O)C1=CC=CC=C1


Input: The molecule is an iridoid monoterpenoid that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted by methyl groups at positions 4 and 7 and a hydroxy group at position 1 (the 1R,4aS,7S,7aR-stereoisomer). It has a role as a plant metabolite. It is a lactol and an iridoid monoterpenoid.

Output: CC1=CO[C@@H](O)[C@H]2[C@@H]1CC[C@@H]2C


Input: The molecule is major microspecies at pH 7.3.

Output: C=CC(C)(C)C1=C(/C=C2/N=C([O-])C(=C)NC2=O)C2=CC=CC=C2N1


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 3-methylundecanoic acid. It is a methyl-branched fatty acyl-CoA and a medium-chain fatty acyl-CoA. It is functionally related to a 3-methylundecanoic acid. It is a conjugate acid of a 3-methylundecanoyl-CoA(4-).

Output: CCCCCCCCC(C)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 an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia.

Output: COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4


Input: The molecule is the 2,3-bis-O-(geranylgeranyl)- derivative of sn-glycerol 1-phosphate. It is a conjugate acid of a 2,3-bis-O-(geranylgeranyl)-sn-glycerol 1-phosphate(2-).

Output: CC(C)=CCC/C(C)=C/CC/C(C)=C/CC/C(C)=C/COC[C@@H](COP(=O)(O)O)OC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C


Input: The molecule is major microspecies at pH 7.3.

Output: CC1=CC(O)=CC(O)=C1C(=O)C1=C([O-])C=C(O)C=C1[O-]


Input: The molecule is a L-serine derivative obtained by formal condensation between N-butyl-L-serinamide and (R)-2-hydroxy-2-phenylacetic acid. It is a secondary alcohol, a monocarboxylic acid amide and a L-serine derivative.

Output: CCCCNC(=O)[C@H](CO)NC(=O)[C@H](O)C1=CC=CC=C1


Input: The molecule is an NADP obtained by formal reduction of the 1,2-position in the pyridine ring of beta-NADP. It is a NADP and a NAD(P)H. It is a conjugate acid of a 2-hydro-beta-NADP(4-).

Output: NC(=O)C1=CC=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](N4C=NC5=C(N)N=CN=C54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C1


Input: The molecule is a monounsaturated fatty acid that is (2E)-non-2-enoic acid in which one of the hydrogens at position 9 is replaced by a hydroxy group. It is a straight-chain fatty acid, an alpha,beta-unsaturated monocarboxylic acid, a hydroxy monounsaturated fatty acid and an omega-hydroxy-medium-chain fatty acid.

Output: O=C(O)/C=C/CCCCCCO


Input: The molecule is an octadecenoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (11Z)-octadecenoic acid. It derives from a cis-vaccenic acid. It is a conjugate acid of an (11Z)-octadecenoyl-CoA(4-).

Output: CCCCCC/C=C\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 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol)(1-) obtained by deprotonation of the phosphate group of 1-oleoyl-2-lauroyl-sn-glycero-3-phospho-(1'-sn-glycerol); major species at pH 7.3. It is a conjugate base of a 1-oleoyl-2-lauroyl-sn-glycero-3-phospho-(1'-sn-glycerol).

Output: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)([O-])OC[C@@H](O)CO)OC(=O)CCCCCCCCCCC


Input: The molecule is a 2-hexenal in which the olefinic double bond has Z configuration. It has a role as a plant metabolite.

Output: CCC/C=C\C=O


Input: The molecule is a ten-membered oligopeptide comprising D-arginyl, L-arginyl, L-prolyl, (4R)-4-hydroxy-L-prolyl, glycyl, L-phenylalanyl, L-seryl, D-phenylalanyl, L-phenylalanyl and L-arginine residues joined in sequence. It has a role as a bradykinin receptor antagonist. It derives from a bradykinin.


Input: The molecule is an organic anion obtained by deprotonation of one of the hydroxy groups of (S)-demethyl-4-deoxygadusol. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.). It is a conjugate base of a (S)-demethyl-4-deoxygadusol.

Output: O=C1C[C@@](O)(CO)CC(O)=C1[O-]


Input: The molecule is an inorganic sodium salt having bromate as the counterion. It has a role as an oxidising agent and a nephrotoxin. It is a bromate salt and an inorganic sodium salt.

Output: [Na+];[O-][Br+2]([O-])[O-]


Input: The molecule is a crystalline solid. Used in the spectrofluorimetric determination of aluminum.

Output: NC1=CC(S(=O)(=O)O)=CC(C(=O)O)=C1O


Input: The molecule is a diterpene alkaloid. It is functionally related to an aconitane.

Output: CCN1CC2(COC)CCC(O)C34C5CC6C(OC)CC(O)(C(CC23)C14)C5C6O


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 is functionally related to 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 branched amino tetrasaccharide consisting of the linear sequence beta-D-GalNAc-(1->4)-beta-D-Gal-(1->4)-beta-D-Glc having a Neu5Ac residue attached to the galactose via an alpha-(2->3) linkage. Corresponds to the carbohydrate portion of ganglioside GM2. It has a role as an epitope. It is an amino tetrasaccharide and a glucosamine oligosaccharide.

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 fatty acid-taurine conjugate derived from arachidonic acid. It has a role as a mouse metabolite. It derives from 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 the conjugate acid of benzyl cetraxate; major species at pH 7.3. It is a conjugate acid of a benzyl cetraxate.

Output: [NH3+]CC1CCC(C(=O)OC2=CC=C(CCC(=O)OCC3=CC=CC=C3)C=C2)CC1


Input: The molecule is a ketoaldonic acid. It is functionally related to a L-idonic acid and a L-gulonic acid. It is a conjugate acid of a 2-dehydro-L-idonate.

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


Input: The molecule is a (2S)-2-methylacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (2S)-2-methyltetradecanoic acid. It is a (2R)-2-methylacyl-CoA and a long-chain fatty acyl-CoA. It is a conjugate acid of a (2S)-2-methyltetradecanoyl-CoA(4-).

Output: CCCCCCCCCCCC[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 a hydroxy monocarboxylic acid anion that is the conjugate base of phloretic acid, arising from deprotonation of the carboxy group. It is functionally related to a propionate. It is a conjugate base of a phloretic acid.

Output: O=C([O-])CCC1=CC=C(O)C=C1


Input: The molecule is a selenium oxoanion. It is a conjugate base of a hydrogenselenite.

Output: O=[Se]([O-])[O-]


Input: The molecule is an anionic C5 cyanine-type compound having indoleinine and dihydropyrano[3,2-g]quinolinium substituents at either end. It has a role as a fluorochrome.

Output: CCN1C2=CC3=C(C=C2C(C)=CC1(C)C)/C(=C/C=C/C=C/C1=[N+](CCCS(=O)(=O)[O-])C2=CC=C(S(=O)(=O)[O-])C=C2C1(C)CCCC(=O)O)C=C(C1=CC=CC=C1)O3


Input: The molecule is a sphingomyelin d18:1 in which the ceramide N-acyl group is specified as dodecanoyl (lauroyl). It is a sphingomyelin 30:1 and a sphingomyelin d18:1.

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


Input: The molecule is a quaternary ammonium ion resulting from the methylation of the nitrogen atom of alpha-berbine. It derives from an alpha-berbine.

Output: C[N+]12CCC3=CC=CC=C3[C@@H]1CC1=CC=CC=C1C2


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 derives from 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 a Cytomegalovirus DNA Terminase Complex Inhibitor. The mechanism of action of it is as a DNA Terminase Complex Inhibitor, and Cytochrome P450 3A Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C9 Inducer, and Cytochrome P450 2C19 Inducer.

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 a limonoid that is 20,21,22,23-tetrahydroazadirone substituted by an additional oxo group at position 23. It has been isolated from Azadirachta indica. It has a role as a metabolite and a plant metabolite. It is an acetate ester, a cyclic terpene ketone, a limonoid, a tetracyclic triterpenoid and a butan-4-olide. It derives from an azadirone.

Output: CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@]3(C)C(=CC[C@H]3[C@H]3COC(=O)C3)[C@@]21C


Input: The molecule is an omega-hydroxy fatty acid ascaroside that is bhos#18 in which the hydroxy group at position 4 of the ascarylopyranose moiety has been has been converted to the corresponding 1H-indole-3-carboxylate ester. It is a metabolite of the nematode Caenorhabditis elegans. It has a role as a Caenorhabditis elegans metabolite. It is a 3-hydroxy carboxylic acid, a 4-O-(1H-indol-3-ylcarbonyl)ascaroside, an omega-hydroxy fatty acid ascaroside and a monocarboxylic acid. It is functionally related to a bhos#18 and a (3R)-3,11-dihydroxyundecanoic acid.

Output: C[C@@H]1O[C@@H](OCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)C1=CNC2=CC=CC=C12


Input: The molecule is a very long-chain fatty acid anion that is the conjugate base of keto mycolic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a mycolate, a branched-chain fatty acid anion, a very long-chain fatty acid anion and an oxo fatty acid anion. It is a conjugate base of a keto mycolic acid.


Input: The molecule is the stable isotope of xenon with relative atomic mass 128.904780, 26.4 atom percent natural abundance and nuclear spin 1/2. It is a xenon(0) and a xenon atom.

Output: [Xe]


Input: The molecule is a substituted calixfuran. It derives from a hydride of a calix[5]furan.

Output: CCC1=C2CC3=C(CC)C(CC)=C(CC4=C(CC)C(CC)=C(CC5=C(CC)C(CC)=C(CC6=C(CC)C(CC)=C(CC(=C1CC)O2)O6)O5)O4)O3


Input: The molecule is an apo carotenoid sesquiterpenoid compound arising from oxidative degradation of the beta,beta-carotene skeleton at the 4'- and 15-positions. It is an enal, an apo carotenoid sesquiterpenoid and a dialdehyde.

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


Input: The molecule is a naturally occurring heavy metal found in the environment commonly in trivalent, Cr(III), and hexavalent, Cr(VI), forms. The reduction of Cr(VI) to Cr(III) results in the formation of reactive intermediates that contribute to the cytotoxicity, genotoxicity and carcinogenicity of Cr(VI)-containing compounds. The major non-occupational source of chromium for humans is food such as vegetables, meat, urban air, hip or knee prostheses and cigarettes. Cr(VI) is a widely used in industrial chemicals, extensively used in paints, metal finishes, steel including stainless steel manufacturing, alloy cast irons, chrome and wood treatment. On the contrary, Cr(III) salts such as chromium polynicotinate, chromium chloride and chromium picolinate (CrP) are used as micronutrients and nutritional supplements and have been demonstrated to exhibit a significant number of health benefits in animals and humans. Physiologically, it exists as an ion in the body. Chromium enters the body through the lungs, gastro-intestinal tract and to a lesser extent through skin. Inhalation is the most important route for occupational exposure, whereas non-occupational exposure occurs via ingestion of chromium-containing food and water. Regardless of route of exposure Cr(III) is poorly absorbed whereas Cr(VI) is more readily absorbed. Further, absorption of Cr(VI) is poorer by oral route, it is thus not very toxic when introduced by the oral route. But chromium is very toxic by dermal and inhalation routes and causes lung cancer, nasal irritation, nasal ulcer, hypersensitivity reactions and contact dermatitis. All the ingested Cr(VI) is reduced to Cr(III) before entering in the blood stream. The main routes for the excretion of chromium are via kidney/urine and the bile/feces. Cr(III) is unable to enter into the cells but Cr(VI) enters through membrane anionic transporters. Intracellular Cr(VI) is metabolically reduced to Cr(III). Cr(VI) does not react with macromolecules such as DNA, RNA, proteins and lipids. However, both Cr(III) and the reductional intermediate Cr(V) are capable of co-ordinate, covalent interactions with macromolecules. Chromium is an essential nutrient required by the human body to promote the action of insulin for the utilization of sugars, proteins and fats. CrP has been used as nutritional supplement; it controls blood sugar in diabetes and may reduce cholesterol and blood pressure levels. Chromium increases insulin binding to cells, insulin receptor number and activates insulin receptor kinase leading to increased insulin sensitivity. But high doses of chromium and long term exposure of it can give rise to various, cytotoxic and genotoxic reactions that affect the immune system of the body. However, the mechanism of the Cr(VI)-induced cytotoxicity is not entirely understood. A series of in vitro and in vivo studies have demonstrated that Cr(VI) induces oxidative stress through enhanced production of reactive oxygen species (ROS) leading to genomic DNA damage and oxidative deterioration of lipids and proteins. A cascade of cellular events occur following Cr(VI)-induced oxidative stress including enhanced production of superoxide anion and hydroxyl radicals, increased lipid peroxidation and genomic DNA fragmentation, modulation of intracellular oxidized states, activation of protein kinase C, apoptotic cell death and altered gene expression. Some of the factors in determining the biological outcome of chromium exposure include the bioavailability, solubility of chromium compounds and chemical speciation, intracellular reduction and interaction with DNA. The chromium genotoxicity manifests as several types of DNA lesions, gene mutations and inhibition of macromolecular synthesis. Further, chromium exposure may lead to apoptosis, premature terminal growth arrest or neoplastic transformation. Chromium-induced tumor suppressor gene p53 and oxidative processes are some of the major factors that may determine the cellular outcome. Studies have utilized these approaches to understand the interrelationship between chromium-induced genotoxicity, apoptosis and effects on immune response. (A7701).

Output: [Cr]


Input: The molecule is a hydroxyacyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of [hydroxy(phenyl)methyl]succinic acid.

Output: CC(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)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C(CC(=O)O)C(O)C1=CC=CC=C1


Input: The molecule is a beta-D-glucoside in which a beta-D-glucopyranosyl residue is attached at position 6 of bracteatin via a glycosidic linkage. It derives from a bracteatin.

Output: O=C1/C(=C/C2=CC(O)=C(O)C(O)=C2)OC2=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C12


Input: The molecule is a N-acyl-4-hydroxy-15-methylhexadecasphinganine in which the acyl group has 25 carbons and 0 double bonds and is 2-hydroxylated. It derives from a 15-methylhexadecaphytosphingosine.

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


Input: The molecule is a branched amino pentasacccharide that is D-galactopyranose that has been glycosylated by 2-acetamido-beta-D-galactopyranosyl-beta-D-glucopyranosyl groups at positions 4 and 6.


Input: The molecule is an organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions. It has a role as an antimicrobial agent, an antibacterial drug, a protein synthesis inhibitor, an Escherichia coli metabolite, a Mycoplasma genitalium metabolite and a geroprotector. It is an organochlorine compound, a diol, a C-nitro compound and a carboxamide.

Output: O=C(N[C@H](CO)[C@H](O)C1=CC=C([N+](=O)[O-])C=C1)C(Cl)Cl


Input: The molecule is a 1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) in which the 1- and 2-acyl groups are specified as octadecanoyl (stearoyl) and hexadecanoyl (palmitoyl) respectively. It is a conjugate acid of a 2-hexadecanoyl-1-octadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)(1-).

Output: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCC


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 derives from 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 monocarboxylic acid amide formed by nucleophilic ring cleavage of the beta-lactam ring of amoxicillin by butylamine. It is a monocarboxylic acid amide and a thiazolidinemonocarboxylic acid. It derives from an amoxicillin. It is a conjugate acid of an amoxicilloyl-butylamine(1-).

Output: CCCCNC(=O)[C@@H](NC(=O)[C@H](N)C1=CC=C(O)C=C1)[C@@H]1N[C@@H](C(=O)O)C(C)(C)S1


Input: The molecule is a aldonolactone phosphate that is L-arabino-1,4-lactone carrying a single phospho substituent at position 5. It is a gamma-lactone and an aldonolactone phosphate. It derives from a L-arabinono-1,4-lactone. It is a conjugate acid of a L-arabino-1,4-lactone-5-phosphate(2-).

Output: O=C1O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]1O


Input: The molecule is an orally available cyclin-dependent kinase (CDK) inhibitor targets at cyclin D1/CDK4 and cyclin D3/CDK6 cell cycle pathway, with potential antineoplastic activity. Ribociclib specifically inhibits CDK4 and 6, thereby inhibiting retinoblastoma (Rb) protein phosphorylation. Inhibition of Rb phosphorylation prevents CDK-mediated G1-S phase transition, thereby arresting the cell cycle in the G1 phase, suppressing DNA synthesis and inhibiting cancer cell growth. Overexpression of CDK4/6, as seen in certain types of cancer, causes cell cycle deregulation.

Output: CN(C)C(=O)C1=CC2=CN=C(NC3=CC=C(N4CCNCC4)C=N3)N=C2N1C1CCCC1


Input: The molecule is an oxalate salt obtained by reaction of 5-nonyloxytryptamine with one equivalent of oxalic acid. 5-HT1B selective agonist, several times more potent than sumatriptan and inactive as a 5-HT1A agonist (Ki at 5-HT1B = 1 nM, selectivity over 5-HT1A > 300-fold). It has a role as a serotonergic agonist. It contains a 5-nonyloxytryptaminium(1+).

Output: CCCCCCCCCOC1=CC=C2NC=C(CCN)C2=C1;O=C(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 docosanoid, a long-chain fatty acid and a hydroperoxy polyunsaturated fatty acid. It is functionally related to 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 structurally similar to gamma-aminobutyric acid (GABA) - an inhibitory neurotransmitter. It may be used to manage neuropathic pain, postherpetic neuralgia, and fibromyalgia among other conditions. Although as per the FDA Label the mechanism of action has not been definitively defined, there is evidence that pregabalin exerts its effects by binding to the α2δ subunit of voltage-dependent calcium channels. Pregabalin is marketed by Pfizer under the trade name Lyrica and Lyrica Cr (extended release). It may have dependence liability if misused but the risk appears to be highest in patients with current or past substance use disorders.

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


Input: The molecule is a broad spectrum antimicrobial, anti-leishmanial, phospholipid drug that was originally developed in the 1980s as an anti-cancer agent. It is currently the only recognized oral agent used to treat visceral, cutaneous, and mucosal forms of leishmaniasis, a neglected tropical disease. It can be administered topically or orally and is only indicated in patients aged 12 years or older. The CDC has also recommended it as a first line treatment for free-living amebae (FLA) infections such as primary amebic meningoencephalitis and granulomatous amebic encephalitis.

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


Input: The molecule is a carbohydrazide that is nicotinohydrazide in which the terminal nitrogen has undergone formal condensation with the aldehyde group of 4-oxo-4H-chromene-3-carbaldehyde. It is an inhibitor of STAT5 (Signal Transducer and Activator of Transcription 5) protein. It has a role as a signal transducer and activator of transcription 5 protein inhibitor. It is a carbohydrazide, a member of chromones and a member of pyridines.

Output: O=C(N/N=C/C1=COC2=CC=CC=C2C1=O)C1=CC=CN=C1


Input: The molecule is an organic heterotetracyclic compound that is 3,4-dihydro-2H,12H-pyrano[2,3-a]xanthene substituted by a 3,4-dihydroxyphenyl group at position 2, hydroxy groups at positions 3, 5, 9 and 10 and a 2-methoxy-2-oxoethyl group at position 12 (the 2R,3R,12S stereoisomer). It is isolated from the barks of Trichilia catigua and exhibits antioxidant activity. It has a role as an antioxidant and a plant metabolite. It is an extended flavonoid, an organic heterotetracyclic compound, a polyphenol, a methyl ester and a member of catechols.

Output: COC(=O)C[C@H]1C2=CC(O)=C(O)C=C2OC2=CC(O)=C3C[C@@H](O)[C@@H](C4=CC=C(O)C(O)=C4)OC3=C21


Input: The molecule is a primary ammonium ion obtained by protonation of the primary amino group of carcinine; major species at pH 7.3. It is a conjugate acid of a carcinine.

Output: [NH3+]CCC(=O)NCCC1=CN=CN1


Input: The molecule is a glycosyloxyflavone and a monosaccharide sulfate that is the 8-O-beta-D-glucuronopyranoside-3''-O-sulfate derivative of hypolaetin. It has been isolated from the seeds of Theobroma grandiflorum and has been shown to exhibit antioxidant activity. It has a role as an antioxidant and a plant metabolite. It is a glucosiduronic acid, a glycosyloxyflavone and a monosaccharide sulfate. It is functionally related to a hypolaetin.

Output: O=C(O)[C@H]1O[C@@H](OC2=C(O)C=C(O)C3=C2OC(C2=CC=C(O)C(O)=C2)=CC3=O)[C@H](O)[C@@H](OS(=O)(=O)O)[C@@H]1O


Input: The molecule is an organic sodium salt resulting from the formal condensation of Chrome fast yellow 8GL (acid form) with two equivalents of sodium hydroxide. It has a role as a fluorochrome and a histological dye. It contains a Chrome fast yellow 8GL(2-).

Output: NC1=C(S(=O)(=O)[O-])C=C2C(=O)N(C3=CC=C([O-])C(C(=O)O)=C3)C(=O)C3=C2C1=CC=C3;[Na+];[Na+]


Input: The molecule is an orally bioavailable second-generation inhibitor of the nuclear enzymes poly(ADP-ribose) polymerase (PARP) type 1 (PARP1) and 2 (PARP2) and tankyrase (TNK; TNKS; TANK) 1 and 2, with potential chemo/radiosensitizing and antineoplastic activities. Upon oral administration, nesuparib selectively and simultaneously targets and binds to PARP1/2 and TNK1/2. Inhibiting PARP activity prevents PARP-mediated DNA repair of single-strand DNA breaks via the base-excision repair pathway. This enhances the accumulation of DNA strand breaks and promotes genomic instability and eventually leads to apoptosis. This may enhance the cytotoxicity of DNA-damaging agents. Inhibiting TNK activity blocks the tankyrase-mediated poly(ADP-ribosyl)ation of multiple target proteins including various tumor suppressors. This may include the blockage of the poly(ADP-ribosyl)ation and destabilization of AXIN, a negative regulator of beta-catenin, thereby stabilizing AXIN. This prevents Wnt/beta-catenin signaling and may inhibit the activation of transcription of a wide range of Wnt/beta-catenin target genes. This may suppress proliferation of cancer cells in which Wnt/beta-catenin signaling is overactivated. PARP catalyzes post-translational ADP-ribosylation of nuclear proteins that signal and recruit other proteins to repair damaged DNA and is activated by single-strand DNA breaks. The PARP-mediated repair pathway is dysregulated in a variety of cancer cell types. TNK, a member of the PARP family, plays an important role in the regulation of the Wnt/beta-catenin signaling pathway.

Output: N#CC1=CC=C(N2CCN(CC3=CC=C4C5=C(CCCN5)C(=O)NC4=C3)CC2)N=C1


Input: The molecule is the methyl ester of dicamba. It has a role as an agrochemical, an environmental contaminant, a herbicide and a synthetic auxin. It is a dichlorobenzene, a monomethoxybenzene and a methyl ester. It is functionally related to a dicamba.

Output: COC(=O)C1=C(Cl)C=CC(Cl)=C1OC


Input: The molecule is a UDP-amino sugar having 3-O-(3-hydroxytetradecanoyl)-N-acetyl-beta-glucosamine as the sugar component. It is functionally related to an UDP-alpha-D-glucosamine. It is a conjugate acid of an UDP-3-O-(3-hydroxytetradecanoyl)-N-acetyl-beta-glucosamine(2-).

Output: CCCCCCCCCCCC(O)CC(=O)O[C@H]1[C@H](O)[C@@H](CO)O[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]1NC(C)=O


Input: The molecule is a member of the class of 2-pyranones that is 5,6-dihydro-2H-pyran-2-one substituted by a hydroxy group at position 5 and a 10-(acetyloxy)-2,4,6,8-tetrahydroxypentacosyl group at position 6.It has been isolated from Cryptocarya species It has a role as a metabolite and a plant metabolite. It is a member of 2-pyranones, a pentol and an acetate ester.

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


Input: The molecule is a diterpenoid that is ent-cassa-12,15-diene carrying oxo and hydroxy substituents at positions 2 and 3beta respectively. It has a role as a plant metabolite. It is a cyclic terpene ketone, a diterpenoid, a secondary alcohol and a secondary alpha-hydroxy ketone. It derives from a hydride of an ent-cassa-12,15-diene.

Output: C=CC1=CC[C@@H]2[C@H](CC[C@@H]3C(C)(C)[C@H](O)C(=O)C[C@@]23C)[C@@H]1C


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 is functionally related to 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 microcystin consisting of D-alanyl, L-arginyl, (3S)-3-methyl-D-beta-aspartyl, L-arginyl, (2S,3S,4E,6E,8S,9S)-3-amino-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyldecanoyl, D-gamma-glutamyl, and 2,3-didehydro-N-methylalanyl residues joined into a 25-membered macrocycle. It has a role as a xenobiotic, an environmental contaminant and a bacterial metabolite. It is an organic molecular entity and a microcystin.

Output: C=C1C(=O)N[C@H](C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](C(=O)O)[C@H](C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](/C=C/C(C)=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)[C@H](C)C(=O)N[C@@H](C(=O)O)CCC(=O)N1C


Input: The molecule is a adenosine 5'-phosphate that is the 2'-O-methyl derivative of adenosine 5'-monophosphate. It is an adenosine 5'-phosphate and a purine ribonucleoside 5'-monophosphate. It derives from an adenosine 5'-monophosphate.

Output: CO[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=NC2=C(N)N=CN=C21


Input: The molecule is an organophosphate oxoanion obtained by deprotonation of the phosphate OH groups of D-psicose 6-phosphate; major species at pH 7.3. It derives from a D-psicose. It is a conjugate base of a D-psicose 6-phosphate.

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


Input: The molecule is a member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14alpha demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4) It has a role as an ergosterol biosynthesis inhibitor, an antifungal drug, an EC 1.14.14.154 (sterol 14alpha-demethylase) inhibitor and an antileishmanial agent. It is a member of triazoles, a member of fluorobenzenes, a tertiary alcohol, a member of 1,3-thiazoles and a nitrile.

Output: C[C@@H](C1=NC(C2=CC=C(C#N)C=C2)=CS1)[C@](O)(CN1C=NC=N1)C1=CC=C(F)C=C1F


Input: The molecule is a dihydroxy monocarboxylic acid that is 9-hydroxynonanoic acid in which the pro-R hydrogen beta to the carboxy group is replaced by a hydroxy group. It is a dihydroxy monocarboxylic acid, a (3R)-3-hydroxy fatty acid and an omega-hydroxy-medium-chain fatty acid. It is functionally related to a 9-hydroxynonanoic acid.

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


Input: The molecule is a quassinoid that is picras-3-ene substituted by hydroxy groups at positions 1, 11, 12 and 15, oxo groups at positions 2 and 16 and a beta-D-glucopyranosyloxy residue at position 21. It has been isolated from he ethanol extract of the stem of Brucea mollis. It has a role as a metabolite and a plant metabolite. It is a delta-lactone, an enone, an organic heterotetracyclic compound, a tetrol, a quassinoid, a terpene glycoside, a monosaccharide derivative, a beta-D-glucoside and a secondary alpha-hydroxy ketone. It derives from a hydride of a picrasane.

Output: CC1=CC(=O)[C@@H](O)[C@]2(C)[C@H]3[C@@H](O)[C@H](O)[C@H](CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]4[C@@H](O)C(=O)O[C@H](C[C@@H]12)[C@@]43C


Input: The molecule is a N-acylsphingosine in which the ceramide N-acyl group is specified as eicosanoyl. It has a role as a mouse metabolite. It is a N-acylsphingosine and a Cer(d38:1). It derives from an icosanoic acid.

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


Input: The molecule is a cyclohexadienedicarboxylic acid. It is a conjugate acid of a (3S,4R)-3,4-dihydroxycyclohexa-1,5-diene-1,4-dicarboxylate.

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


Input: The molecule is a popular herbal laxative that is available without prescription. Senna is generally safe and well tolerated, but can cause adverse events including clinically apparent liver injury when used in high doses for longer than recommended periods.

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 non-sulfhydryl angiotensin converting enzyme (ACE) inhibitor with antihypertensive activity. Moexiprilat competitively inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the actions of the potent vasoconstrictor angiotensin II and leads to vasodilatation. This agent also prevents angiotensin II-induced aldosterone secretion by the adrenal cortex, thereby promoting diuresis and natriuresis.

Output: COC1=CC2=C(C=C1OC)CN(C(=O)[C@H](C)N[C@@H](CCC1=CC=CC=C1)C(=O)O)[C@H](C(=O)O)C2


Input: The molecule is an organic dilithium salt having 6-amino-2-[(hydrazinocarbonyl)amino]-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5,8-disulfonate as the counterion. It has a role as a fluorochrome. It contains a lucifer yellow carbohydrazide dye(2-).

Output: NNC(=O)NN1C(=O)C2=C3C(=CC(S(=O)(=O)[O-])=C(N)C3=CC(S(=O)(=O)[O-])=C2)C1=O;[Li+];[Li+]


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

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


Input: The molecule is a hydroxy monocarboxylic acid anion that is the conjugate base of phloretic acid, arising from deprotonation of the carboxy group. It derives from a propionate. It is a conjugate base of a phloretic acid.

Output: O=C([O-])CCC1=CC=C(O)C=C1


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

Output: CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCO


Input: The molecule is a duloxetine. It is an enantiomer of a (R)-duloxetine.

Output: CNCC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1


Input: The molecule is an orally bioavailable, small-molecule focal adhesion kinase (FAK) inhibitor with potential antiangiogenic and antineoplastic activities. Defactinib inhibits FAK, which may prevent the integrin-mediated activation of several downstream signal transduction pathways, including those involving RAS/MEK/ERK and PI3K/Akt, thus inhibiting tumor cell migration, proliferation, survival, and tumor angiogenesis. The tyrosine kinase FAK, a signal transducer for integrins, is normally activated by binding to integrins in the extracellular matrix (ECM) but may be upregulated and constitutively activated in various tumor cell types.

Output: CNC(=O)C1=CC=C(NC2=NC=C(C(F)(F)F)C(NCC3=NC=CN=C3N(C)S(C)(=O)=O)=N2)C=C1


Input: The molecule is a dicarboxylic acid dianion resulting from the removal of a proton from both of the carboxy groups of succinic acid. It has a role as a human metabolite and a Saccharomyces cerevisiae metabolite. It is a C4-dicarboxylate, a dicarboxylic acid dianion and a succinate. It is a conjugate base of a succinate(1-).

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


Input: The molecule is a glycophytoceramide having a 4-O-(cyclobutylmethyl)-alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen. One of a series of an extensive set of 4"-O-alkylated alpha-GalCer analogues evaluated (PMID:30556652) as invariant natural killer T-cell (iNKT) antigens. It derives from an alpha-D-galactose.

Output: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1O[C@H](CO)[C@H](OCC2CCC2)[C@H](O)[C@H]1O)[C@H](O)[C@H](O)CCCCCCCCCCCCCC


Input: The molecule is a phosphatidylcholine O-38:3 in which the alkyl and acyl groups specified at positions 1 and 2 are octadecyl and (8Z,11Z,14Z)-eicosatrienoyl respectively. It is a phosphatidylcholine O-38:3 and a 2-acyl-1-alkyl-sn-glycero-3-phosphocholine. It is functionally related to an all-cis-icosa-8,11,14-trienoic acid.

Output: CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C


Input: The molecule is a monoazo compound consisting of diazene with a 5-nitrothiazol-2-yl group attached to one nitrogen and a substituted 4-aminophenyl group attached to the other; used as a dye standard for the assay of allergy-releasing dyes in textiles. It has a role as a dye, a hapten and an allergen. It is a member of 1,3-thiazoles, a monoazo compound and a tertiary amine.

Output: CCN(CCOC(C)=O)C1=CC=C(N=NC2=NC=C([N+](=O)[O-])S2)C(C)=C1


Input: The molecule is an amino disaccharide consisting of an alpha-L-fucosyl residue attached to N-acetyl-beta-Dglucosamine by a (1->4)-glycosidic linkage. It has a role as an epitope. It is an amino disaccharide and a glucosamine oligosaccharide.

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


Input: The molecule is a polyketide obtained by hydrolysis of the pyranone ring of monacolin J. It has a role as a fungal metabolite. It is a polyketide, a hydroxy monocarboxylic acid and a member of hexahydronaphthalenes. It derives from a monacolin J. It is a conjugate acid of a monacolin J carboxylate.

Output: C[C@H]1C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(=O)O)[C@H]2[C@@H](O)C1


Input: The molecule is a member of the class of benzophenones that is benzophenone substituted by a geranyl group at position 3 and hydroxy groups at positions 2, 4 and 6 respectively. Isolated from Leontonyx and Garcinia vieillardii, it exhibits a significant antileishmanial activity. It has a role as a metabolite and an antileishmanial agent. It is a member of benzophenones and a polyphenol.

Output: CC(C)=CCC/C(C)=C/CC1=C(O)C=C(O)C(C(=O)C2=CC=CC=C2)=C1O


Input: The molecule is one of several known isoflavones. Isoflavones compounds, such as genistein and daidzein, are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Genistein is a natural bioactive compound derived from legumes and has drawn because of its potentially beneficial effects on some human degenerative diseases. It has a weak estrogenic effect and is a well-known non-specific tyrosine kinase inhibitor at pharmacological doses. Epidemiological studies show that genistein intake is inversely associated with the risk of cardiovascular diseases. Data suggests a protective role of genistein in cardiovascular events. However, the mechanisms of the genistein action on vascular protective effects are unclear. Past extensive studies exploring its hypolipidemic effect resulted in contradictory data. Genistein also is a relatively poor antioxidant. However, genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis. Genistein exerts a non-genomic action by targeting on important signaling molecules in vascular endothelial cells (ECs). Genistein rapidly activates endothelial nitric oxide synthase and production of nitric oxide in ECs. This genistein effect is novel since it is independent of its known effects, but mediated by the cyclic adenosine monophosphate/protein kinase A (cAMP/PKA) cascade. Genistein directly stimulates the plasma membrane-associated adenylate cyclases, leading to activation of the cAMP signaling pathway. In addition, genistein activates peroxisome proliferator-activated receptors, ligand-activated nuclear receptors important to normal vascular function. Furthermore, genistein reduces reactive oxygen species (ROS) by attenuating the expression of ROS-producing enzymes. These findings reveal the roles for genistein in the regulation of vascular function and provide a basis for further investigating its therapeutic potential for inflammatory-related vascular disease.  (A3190).

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


Input: The molecule is a hydroxy monocarboxylic acid. It is functionally related to a cyclohexanecarboxylic acid.

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


Input: The molecule is an organic cation obtained by protonation of the free amino group of any N-monoacetylalkane-alpha,omega-diamine; major species at pH 7.3. It is an ammonium ion derivative and an organic cation. It is a conjugate acid of a N-monoacetylalkane-alpha,omega-diamine.

Output: CC(=O)NCCC[NH3+]


Input: The molecule is an alkylglucosinolic acid that consists of 1-thio-beta-D-glucopyranose attached to a N-(sulfooxy)pentanimidoyl group at the anomeric sulfur. It is a conjugate acid of a butylglucosinolate.

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


Input: The molecule is a dihydroxyflavone that is tricin 4'-O-(threo-beta-guaiacylglyceryl) ether in which the phenolic hydrogen at position 7 has been replaced by a beta-D-glucopyranosyl group. It has a role as a plant metabolite. It is a beta-D-glucoside, a dimethoxyflavone, a monosaccharide derivative, a polyphenol, a monohydroxyflavone and a glycosyloxyflavone. It derives from a 3',5'-di-O-methyltricetin and a (+)-(7S,8S)-guaiacylglycerol.

Output: COC1=CC([C@H](O)[C@H](CO)OC2=C(OC)C=C(C3=CC(=O)C4=C(O)C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C=C4O3)C=C2OC)=CC=C1O


Input: The molecule is dianion of red chlorophyll catabolite. It is a conjugate base of a red chlorophyll catabolite.

Output: C=CC1=C([O-])NC(/C=C2\N=C(C3=C(C(=O)OC)C(=O)C4=C3NC(CC3=C(CC)C(C)=C(C=O)N3)=C4C)[C@@H](CCC(=O)[O-])[C@@H]2C)=C1C


Input: The molecule is an organic heterotetracyclic compound that is 1,4,5,6,7,8-hexahydro-2H-3,6-ethanoazonino[5,4-b]indole in which position 5 is substituted by an ethylidene group and position 7S is substituted by a methoxycarbonyl group. It is a methyl ester, a monoterpenoid indole alkaloid, an organic heterotetracyclic compound and a bridged compound. It is a conjugate base of a (16S)-deshydroxymethyl-stemmadenine(1+).

Output: C/C=C1/CN2CCC3=C(NC4=CC=CC=C34)[C@@H](C(=O)OC)[C@H]1CC2


Input: The molecule is a member of the class of benzimidazoles that is 1-methyl-1H-benzimidazole which is substituted at positions 4, 5, and 6 by fluorine, (4-bromo-2-fluorophenyl)nitrilo, and N-(2-hydroxyethoxy)aminocarbonyl groups, respectively. It is a MEK1 and MEK2 inhibitor (IC50= 12 nM). Approved by the FDA for the treatment of patients with unresectable or metastatic melanoma with a BRAF V600E or V600K mutation in combination with encorafenib. It has a role as an EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor, an antineoplastic agent and an apoptosis inducer. It is a member of benzimidazoles, a member of bromobenzenes, a member of monofluorobenzenes, a hydroxamic acid ester and a secondary amino compound.

Output: CN1C=NC2=C(F)C(NC3=CC=C(Br)C=C3F)=C(C(=O)NOCCO)C=C21


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 is functionally related to 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 an analog of fentanyl and is one of the most potent opioids available today. It displays most similarity to carfentanil (4-carbomethoxyfentanyl) and is considered to be slightly more potent than this drug.

Output: CCC(=O)N(C1=CC=CC=C1)[C@@]1(C(=O)OC)CCN(CCC2=CC=CC=C2)C[C@H]1C


Input: The molecule is an organophosphate oxoanion arising from deprotonation of the phosphate and diphosphate OH groups of 2-hydro-beta-NAD; major species at pH 7.3. It is a conjugate base of a 2-hydro-beta-NAD.

Output: NC(=O)C1=CC=CN([C@@H]2O[C@H](COP(=O)([O-])OP(=O)([O-])OC[C@H]3O[C@@H](N4C=NC5=C(N)N=CN=C54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C1


Input: The molecule is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (7R)-7-hydroxyoctanoic acid. It is a metabolite of the nematode Caenorhabditis elegans. It has a role as a Caenorhabditis elegans metabolite. It is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside, a monocarboxylic acid and an (omega-1)-hydroxy fatty acid ascaroside. It derives from an ascr#14 and a (7R)-7-hydroxyoctanoic acid.

Output: C[C@H](CCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)C2=CNC3=CC=CC=C23)C[C@H]1O


Input: The molecule is a phosphatidylcholine O-38:3 in which the alkyl and acyl groups specified at positions 1 and 2 are octadecyl and (8Z,11Z,14Z)-eicosatrienoyl respectively. It is a phosphatidylcholine O-38:3 and a 2-acyl-1-alkyl-sn-glycero-3-phosphocholine. It derives from an all-cis-icosa-8,11,14-trienoic acid.

Output: CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[C@H](COCCCCCCCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C


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 derives from 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 mannosylinositol phosphorylceramide(1-) having a tetracosanoyl group attached to the ceramide nitrogen, hydroxylation at C-4 of the long-chain base, and hydroxylation at C-2 and C-3 of the very-long-chain fatty acid. Major species at pH 7.3. It is a conjugate base of a Man-beta1-2-Ins-1-P-Cer(t18:0/2,3-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]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O)[C@H](O)C(O)CCCCCCCCCCCCCC


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

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


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

Output: [Mn]


Input: The molecule is a dicarboxylic acid monoester resulting from the formal condensation of the carboxy group of nonanedioic acid with the hydroxy group of hexopyranose. It has a role as a plant metabolite. It is a glycoside, an organic hydroxy compound and a dicarboxylic acid monoester. It derives from a nonanedioic acid.

Output: O=C(O)CCCCCCCC(=O)OC1OC(CO)C(O)C(O)C1O


Input: The molecule is dianion of 5-amino-6-(5-phosphoribitylamino)uracil arising from deprotonation of both phosphate OH groups. It has a role as a Saccharomyces cerevisiae metabolite. It is a conjugate base of a 5-amino-6-(5-phospho-D-ribitylamino)uracil.

Output: NC1=C(NC[C@H](O)[C@H](O)[C@H](O)COP(=O)([O-])[O-])NC(=O)NC1=O


Input: The molecule is a phosphatidylcholine 32:0 in which the acyl group specified at positions 1 and 2 are stearoyl and myristoyl respectively. It is a phosphatidylcholine 32:0 and a tetradecanoate ester. It derives from an octadecanoic acid.

Output: CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC


Input: The molecule is a triterpenoid saponin isolated from Sapindus mukorossi and has been shown to exhibit inhibitory activity against platelet aggregation. It has a role as a platelet aggregation inhibitor and a plant metabolite. It is a trisaccharide derivative, a member of oxolanes, a triterpenoid saponin and a tirucallane triterpenoid.


Input: The molecule is a doubly-charged nucleotide-sugar oxoanion arising from deprotonation of the carboxylic acid and phosphate functions of CMP-pseudaminic acid. It derives from a pseudaminate. It is a conjugate base of a CMP-pseudaminic acid.

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


Input: The molecule is an omega-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 8-hydroxyoctanoic acid with ascarylopyranose (the alpha anomer). It is a metabolite of the nematode Caenorhabditis elegans. It has a role as a Caenorhabditis elegans metabolite. It is a monocarboxylic acid and an omega-hydroxy fatty acid ascaroside. It derives from an 8-hydroxyoctanoic acid. It is a conjugate acid of an oscr#14(1-).

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


Input: The molecule is an organophosphate oxoanion obtained by deprotonation of the phosphate and diphosphate functions of 4-O-[(2R)-1-glycerylphosphonato]-N-acetyl-beta-D-mannosaminyl-(1->4)-N-acetyl-alpha-D-glucosaminyl undecaprenyl diphosphate; major species at pH 7.3. It is a conjugate base of a 4-O-[(2R)-1-glycerylphosphono]-N-acetyl-beta-D-mannosaminyl-(1->4)-N-acetyl-alpha-D-glucosaminyl undecaprenyl diphosphate.


Input: The molecule is a selective, very potent, small-molecule Bradykinin B2 receptor antagonist. It is developed for the for the treatment of traumatic brain injury (TBI).

Output: CC1=CC(C)=C2C=CC=C(OCC3=C(Cl)C=CC(S(=O)(=O)N4CCC[C@H]4C(=O)NCCCNC(=O)C4=CC=C(C(=N)N)C=C4)=C3Cl)C2=N1


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 derives from 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 the cartenoid ether that is the methyl ether of 3,4-didehydro-1,2,7',8'-tetrahydro-psi,psi-caroten-1-ol.

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


Input: The molecule is an organic disulfide obtgained by oxidative dimerisation of cysteamine. It has a role as an EC 2.3.2.13 (protein-glutamine gamma-glutamyltransferase) inhibitor. It is an organic disulfide and a primary amino compound. It is functionally related to a cysteamine.

Output: NCCSSCCN


Input: The molecule is a fatty acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate functions of 2-hydroxydodecanoyl-CoA; major species at pH 7.3. It derives from a lauroyl-CoA(4-). It is a conjugate base of a 2-hydroxydodecanoyl-CoA.

Output: CCCCCCCCCCC(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 1,3-diglyceride with both acyl groups specified as oleoyl. It is a 1,3-diglyceride, a dioleoylglycerol and a diacylglycerol (18:1/0:0/18:1). It derives from an oleic acid.

Output: CCCCCCCC/C=C\CCCCCCCC(=O)OCC(O)COC(=O)CCCCCCC/C=C\CCCCCCCC


Input: The molecule is a benzoylurea insecticide that is urea in which a hydrogen attached to one of the nitrogens is replaced by a 4-chlorophenyl group, and a hydrogen attached to the other nitrogen is replaced bgy a 2,6-difluorobenzoyl group. It has a role as an insect sterilant. It is a benzoylurea insecticide and a member of monochlorobenzenes. It is functionally related to a 1,3-difluorobenzene.

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


Input: The molecule is a aldonolactone phosphate that is L-arabino-1,4-lactone carrying a single phospho substituent at position 5. It is a gamma-lactone and an aldonolactone phosphate. It is functionally related to a L-arabinono-1,4-lactone. It is a conjugate acid of a L-arabino-1,4-lactone-5-phosphate(2-).

Output: O=C1O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]1O


Input: The molecule is the cation resulting from the removal of a proton from the N(3) position of methohexital. It is a conjugate base of a methohexital.

Output: C=CCC1(C(C)C#CCC)C(=O)N(C)C(=O)N=C1[O-]


Input: The molecule is a diterpenoid of the class of daphnane-type terpenes. It is isolated from Trigonostemon reidioides and has been shown to exhibit insecticidal activity. It has a role as a metabolite and an insecticide. It is a diterpenoid, an ortho ester, an epoxide and a terpene lactone.

Output: CC(C)CC(=O)O[C@@H]1/C=C\C=C\C(=O)O[C@H]2[C@@H](C)C[C@@H]3[C@]2(O)[C@H](O)[C@@]2(CO)O[C@H]2[C@H]2[C@H]4O[C@]5(C6=CC=CC=C6)O[C@@H]([C@@H](C)[C@@]23O5)[C@@]4(O)[C@](C)(O)C[C@H]2CC[C@H]1[C@H]2C


Input: The molecule is a bisindole alkaloid that is phenol bearing a 3,3-dimethylallyl group at position 4, two methoxy groups at positions 3 and 6, and two indol-3-yl groups at positions 2 and 5. It is a natural product isolated from the sclerotia of Aspergillus orbraceus, with moderate activity against some insects, as well as Gram-positive bacteria. It has a role as an Aspergillus metabolite, an antibacterial agent and an insecticide. It is a bisindole alkaloid, a member of phenols, a dimethoxybenzene, a member of indoles and an olefinic compound.

Output: COC1=C(CC=C(C)C)C(C2=CNC3=CC=CC=C23)=C(OC)C(O)=C1C1=CNC2=CC=CC=C12


Input: The molecule is a monocarboxylic acid that is D-penicillamine in which the amino group has been replaced by a consisting 2-benzyl-1H-imidazol-1-yl moiety. It is a member of imidazoles, a monocarboxylic acid, a thiol and a non-proteinogenic alpha-amino acid. It is functionally related to a D-penicillamine.

Output: CC(C)(S)[C@H](C(=O)O)N1C=CN=C1CC1=CC=CC=C1


Input: The molecule is an orally available inhibitor of spleen tyrosine kinase (Syk), with potential immunomodulating and antineoplastic activities. Upon oral administration, lanraplenib binds to and inhibits the activity of Syk. This inhibits B-cell receptor (BCR) signaling, which leads to the inhibition of B-cell activation, and prevents tumor cell activation, migration, adhesion and proliferation. Syk, a non-receptor cytoplasmic, BCR-associated tyrosine kinase, is expressed in hematopoietic tissues and is often overexpressed in hematopoietic malignancies; it plays a key role in B-cell receptor signaling.

Output: NC1=CN=CC(C2=CN3C=CN=C3C(NC3=CC=C(N4CCN(C5COC5)CC4)C=C3)=N2)=N1


Input: The molecule is an inositol phosphodihydroceramide(1-) in which the N-acyl group is specified as hexanoyl; major species at pH 7.3. It is an inositol phosphodihydroceramide(1-) and an Ins-1-P-Cer-A 34:0(1-). It is functionally related to a N-hexadecanoylsphinganine.

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


Input: The molecule is a synthetic, broad-spectrum fluoroquinolone with antibacterial activity. Norfloxacin inhibits activity of DNA gyrase, thereby blocking bacterial DNA replication. Norfloxacin concentrates in the renal tubules and bladder and is bactericidal against a wide range of aerobic gram-positive and gram-negative organisms.

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


Input: The molecule is an acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of oscr#34. It derives from an oscr#34. It is a conjugate acid of an oscr#34-CoA(4-).

Output: C[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=NC4=C(N)N=CN=C43)[C@H](O)[C@@H]2OP(=O)(O)O)[C@H](O)C[C@H]1O


Input: The molecule is a formate ester of octan-1-ol. It has a role as a metabolite. It is functionally related to an octan-1-ol.

Output: CCCCCCCCOC=O


Input: The molecule is an agent belonging to the glitazone class of antidiabetic agents with antihyperglycemic activity. Besides its activation of peroxisome proliferator-activated receptor (PPAR) gamma, lobeglitazone is also a potent agonist for PPARalpha.

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 meroterpenoid found in Penicillium rubrum and Penicillium species. It has been found to exhibit inhibitory activity against the production of interleukin 1-beta from induced inflammasomes. It has a role as a metabolite, a cysteine protease inhibitor and a Penicillium metabolite. It is an organic heterotetracyclic compound, a terpene lactone, a carboxylic ester, a cyclic terpene ketone, a meroterpenoid, a tertiary alcohol and a tertiary alpha-hydroxy ketone.

Output: C=C1[C@@]2(C)C[C@H]3[C@]4(C)CCC(=O)OC(C)(C)[C@H]4CC[C@]3(C)[C@]1(C(=O)OC)C(=O)[C@@](C)(O)C2=O


Input: The molecule is found in cloves. DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. It was used in some nail polishes; all major producers began eliminating this chemical from nail polishes in the Fall of 2006. Dibutyl phthalate (DBP) is a commonly used plasticizer. It is also used as an additive to adhesives or printing inks. It is soluble in various organic solvents, e.g. in alcohol, ether and benzene. DBP is also used as an ectoparasiticide.

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


Input: The molecule is a citrate salt that is the dihydrogen citrate salt of deptropamine. It has a role as a muscarinic antagonist, a H1-receptor antagonist and a parasympatholytic. It contains a deptropine.

Output: CN1[C@@H]2CC[C@H]1CC(OC1C3=CC=CC=C3CCC3=CC=CC=C31)C2;O=C(O)CC(O)(CC(=O)O)C(=O)O


Input: The molecule is a derivative of vitexin having a alpha-L-rhamnosyl residue attached at the 2''-position of the glucitol moiety and a methyl group attached at the O-7 position of the chromene. It is a dihydroxyflavone, a monomethoxyflavone, a disaccharide derivative and a C-glycosyl compound. It derives from a vitexin. It is a conjugate acid of a 7-O-methylvitexin 2''-O-alpha-L-rhamnoside(1-).

Output: COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O


Input: The molecule is a tellurium oxoanion. It is a conjugate base of a hydrogentellurate.

Output: O=[Te](=O)([O-])[O-]


Input: The molecule is a carboxylic ester resulting from the formal condensation of the carboxy group of isobutyric acid with the 1-hydroxy group of 2,4,4-trimethylpentane-1,3-diol. It has a role as a human urinary metabolite and a plant metabolite. It is a carboxylic ester, a volatile organic compound and a secondary alcohol. It is functionally related to an isobutyric acid.

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


Input: The molecule is a derivative of vitexin having a alpha-L-rhamnosyl residue attached at the 2''-position of the glucitol moiety and a methyl group attached at the O-7 position of the chromene. It is a dihydroxyflavone, a monomethoxyflavone, a disaccharide derivative and a C-glycosyl compound. It is functionally related to a vitexin. It is a conjugate acid of a 7-O-methylvitexin 2''-O-alpha-L-rhamnoside(1-).

Output: COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O


Input: The molecule is a member of the class of quinolines that is 1,2,3,4-tetrahydroquinoline which is substituted at positions 2, 6, and 7 by (isopropylamino)methyl, hydroxymethyl, and nitro groups, respectively. It is a member of quinolines, a C-nitro compound, a secondary amino compound and an aromatic primary alcohol.

Output: CC(C)NCC1CCC2=CC(CO)=C([N+](=O)[O-])C=C2N1


Input: The molecule is an orally bioavailable pyrimidine analogue prodrug with potential antineoplastic activity. Sapacitabine is hydrolyzed by amidases to the deoxycytosine analogue CNDAC (2'-Cyano-2'-deoxyarabinofuranosylcytosine), which is then phosphorylated into the active triphosphate form. As an analogue of deoxycytidine triphosphate, CNDAC triphosphate incorporates into DNA strands during replication, resulting in single-stranded DNA breaks during polymerization due to beta-elimination during the fidelity checkpoint process; cell cycle arrest in the G2 phase and apoptosis ensue. The unmetabolized prodrug may exhibit antineoplastic activity as well.

Output: CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2C#N)C=C1


Input: The molecule is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

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


Input: The molecule appears as a clear colorless liquid with an ammonia-like odor. Flash point 30 °F. Irritates the eyes and respiratory system. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion. Used as a corrosion inhibitor, solvent, flotation agent and in the manufacture of other chemicals.

Output: CCCCCN


Input: The molecule is a lysophosphatidylethanolamine 20:3 in which the acyl group is specified as (5Z,8Z,11Z)-icosatrienoyl and is located at position 2. It has a role as a mouse metabolite. It is a lysophosphatidylethanolamine 20:3 and a 2-acyl-sn-glycero-3-phosphoethanolamine. It is functionally related to a (5Z,8Z,11Z)-icosatrienoic acid.

Output: CCCCCCCC/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](CO)COP(=O)(O)OCCN


Input:
The molecule is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). It is manufactured and marketed by Eli Lilly and Company.
Duloxetine has not yet been FDA approved for stress urinary incontinence or for fibromyalgia.
Duloxetine is a selective SNRI (selective serotonin-norepinephrine reuptake inhibitor). Duloxetine is a systemic drug therapy which affects the body as a whole. Known also under the code name LY248686, it is a potent dual reuptake inhibitor of serotonin (5-hydroxytryptamine, 5-HT) and norepinephrine (NE), possessing comparable affinities in binding to NE- and 5-HT transporter sites. It is a less potent inhibitor of dopamine reuptake.

Output: CNCC[C@H](OC1=CC=CC2=CC=CC=C12)C1=CC=CS1


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

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-tryptophan and L-alanine residues. It has a role as a metabolite. It derives from 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 diterpenoid with a rearranged neo-clerodane skeleton isolated from Salvia leucantha and has been shown exhibit antineoplastic activity. It has a role as a metabolite and an antineoplastic agent. It is a diterpenoid, a gamma-lactone, a member of furans and a bridged compound.

Output: O=C1OC[C@@]23C1=C[C@H]1C[C@@]24C=CC2=C([C@@H](C5=COC=C5)OC2=O)[C@]43C1


Input: The molecule is a lignan isolated from the leaves of Piper sanguineispicum. It has a role as a plant metabolite. It is a lignan, a member of benzodioxoles and a gamma-lactone.

Output: O=C1OC[C@H]([C@H](O)C2=CC=C3OCOC3=C2)[C@H]1C(=O)C1=CC=C2OCOC2=C1


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 derives from 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 is a synthetic organophosphate compound that blocks the activity of enolpyruvylshikimate-3-phosphate (EPSP) synthase and is used as a broad-spectrum pesticide. It is characterized as a volatile, moderately toxic, colorless, odorless crystalline solid or powder, and exposure occurs by inhalation, ingestion, or contact.

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


Input: The molecule is an alkylating agent that binds to the minor groove of DNA. It's association with severe myelotoxicity lead to the end of its development in favour of α-halogenoacrylamide derivatives such as [brostallicin], which have a favourable cytotoxicity/myelotoxicity ratio. Newer generations of DNA minor groove binding agents can more specifically recognize base pair sequences.

Output: CN1C=C(NC(=O)C2=CC(NC(=O)C3=CC(NC(=O)C4=CC=C(N(CCCl)CCCl)C=C4)=CN3C)=CN2C)C=C1C(=O)NCCC(=N)N


Input: The molecule is a dicarboxylic acid dianion resulting from the deprotonation of the two carboxy groups of 2,2-dimethylsuccinic acid; major species at pH 7.3. It is a conjugate base of a 2,2-dimethylsuccinic acid.

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


Input: The molecule is a glycosyloxyflavone that is isorhamnetin substituted at position 4' by a beta-D-glucosyl residue. It has a role as a metabolite. It is a beta-L-glucoside, a glycosyloxyflavone, a monomethoxyflavone, a monosaccharide derivative and a trihydroxyflavone. It is functionally related to a beta-L-glucose and an isorhamnetin.

Output: COC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O


Input: The molecule is a naturally occurring D-hormone that is produced by the kidneys from vitamin D. LR-103 is one of the D-hormones produced from Hectorol. It is developed for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease (CKD). Studies have shown LR-103 has the same potency as calcitriol, but much lower toxicity.

Output: C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)/C=C/[C@@](C)(O)C(C)C)CC[C@@H]23)C[C@@H](O)C[C@@H]1O