Input: The molecule is a methyl-branched fatty acid that is octacosanoic acid (montanic acid) substituted by a methyl group at position 26. It is a branched-chain saturated fatty acid, a methyl-branched fatty acid and an ultra-long-chain fatty acid. It is functionally related to an octacosanoic acid.

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


Input: The molecule is an orally bioavailable small-molecule inhibitor of MEK1 and MEK2 (MEK1/2) with potential antineoplastic activity. Pimasertib selectively binds to and inhibits the activity of MEK1/2, preventing the activation of MEK1/2-dependent effector proteins and transcription factors, which may result in the inhibition of growth factor-mediated cell signaling and tumor cell proliferation. MEK1/2 (MAP2K1/K2) are dual-specificity threonine/tyrosine kinases that play key roles in the activation of the RAS/RAF/MEK/ERK pathway and are often upregulated in a variety of tumor cell types.

Output: O=C(NC[C@H](O)CO)C1=CC=NC=C1NC1=CC=C(I)C=C1F


Input: The molecule is an antidepressant and a serotonin and norepinephrine reuptake inhibitor (SNRI). Its active metabolite, [desvenlafaxine], works by blocking the reuptake of serotonin and norepinephrine, which are key neurotransmitters in mood regulation. Venlafaxine is officially approved to treat major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder, and panic disorder in adults. The immediate formulation of the drug, marketed as Effexor, was first approved by the FDA in 1993 and the extended-release formulation, Effexor XR, was later introduced in 1997.  Venlafaxine has been used as a first-line treatment for MDD, GAD, social anxiety disorder, and panic disorder in Canada for many years. It was also considered a second-line treatment for obsessive-compulsive disorder (OCD). Venlafaxine was also investigated in off-label uses for the prophylaxis of migraine headaches, for reduction of vasomotor symptoms associated with menopause, and for the management of neuropathic pain (although there is only minimal evidence of efficacy for this condition).

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


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

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


Input: The molecule is the (R)-enantiomer of lipoic acid. A vitamin-like, C8 thia fatty acid with anti-oxidant properties. It has a role as a prosthetic group, a nutraceutical and a cofactor. It is a lipoic acid, a member of dithiolanes, a heterocyclic fatty acid and a thia fatty acid. It is functionally related to an octanoic acid. It is a conjugate acid of a (R)-lipoate. It is an enantiomer of a (S)-lipoic acid.

Output: O=C(O)CCCC[C@@H]1CCSS1


Input: The molecule is a first generation antihistamine. However, it rapidly permeates the brain and so often causes drowsiness as a side effect. It has been found in over-the-counter combination products for colds and menstrual symptoms, but is considered to be an unapproved prescription medication used for cough, cold, or allergic conditions.

Output: COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1


Input: The molecule is an aromatic amide obtained by formal condensation of the carboxy group of 3-(difluoromethyl)-1-methylpyrazole-4-carboxylic acid with the amino group of 3',4',5'-trifluorobiphenyl-2-amine. Used to control a number of cereal fungal pathogens including those belonging to the Ascomycetes, Basidiomycetes and Zygomycetes families. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is an aromatic amide, a member of biphenyls, a member of pyrazoles, a trifluorobenzene and an anilide fungicide.

Output: CN1C=C(C(=O)NC2=CC=CC=C2C2=CC(F)=C(F)C(F)=C2)C(C(F)F)=N1


Input: The molecule is an organic cation obtained by protonation of the secondary amino group of cobimetinib. It is an ammonium ion derivative and an organic cation. It is a conjugate acid of a cobimetinib.

Output: O=C(C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F)N1CC(O)([C@@H]2CCCC[NH2+]2)C1


Input: The molecule is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane.

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


Input: The molecule is a 2-deoxy-2-fluorohexopyranose. It is functionally related to a D-galactopyranose.

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


Input: The molecule is a non-proteinogenic alpha-amino acid. It is functionally related to a dopa.

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


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

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


Input: The molecule is a phosphatidylglycerol in which the phosphatidyl acyl groups are both lauroyl. It is a phosphatidylglycerol and a dodecanoate ester. It derives from a dodecanoic acid.

Output: CCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO)OC(=O)CCCCCCCCCCC


Input: The molecule is a gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. It has a role as an anticonvulsant and a calcium channel blocker. It derives from a gamma-aminobutyric acid.

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


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

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


Input: The molecule is a secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections. It has a role as a piscicide, a molluscicide, an antiparasitic agent, an anticoronaviral agent, an anthelminthic drug, an apoptosis inducer and a STAT3 inhibitor. It is a member of monochlorobenzenes, a member of salicylanilides, a C-nitro compound, a secondary carboxamide and a member of benzamides. It is functionally related to a 5-chlorosalicylic acid.

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


Input: The molecule is an organophosphate oxoanion arising from deprotonation of both free diphosphate OH groups of beta-D-Gal-(1->3)-alpha-D-GalNAc-(1->3)-alpha-D-GalNAc-diphospho-ditrans,octacis-undecaprenol. It is a conjugate base of a beta-D-Gal-(1->3)-alpha-D-GalNAc-(1->3)-alpha-D-GalNAc-diphospho-ditrans,octacis-undecaprenol.


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 is functionally related to 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 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 derives from a cysteamine.

Output: NCCSSCCN


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 is functionally related to an oleic acid.

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


Input: The molecule is a dipeptide formed from L-alanyl and L-histidine residues. It has a role as a metabolite. It is a tautomer of an Ala-His zwitterion.

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


Input: The molecule is a dihydroxyanthraquinone having the two hydroxy substituents at the 1- and 4-positions; formally derived from anthraquinone by replacement of two hydrogen atoms by hydroxy groups It has a role as a dye.

Output: O=C1C2=CC=CC=C2C(=O)C2=C(O)C=CC(O)=C12


Input: The molecule is a steroidal acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate OH groups of any 3alpha-hydroxy bile acid; major species at pH 7.3.

Output: C[C@H](CCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)([O-])OP(=O)([O-])OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1OP(=O)([O-])[O-])[C@H]1CCC2C3CCC4C[C@H](O)CC[C@]4(C)C3CC[C@@]21C


Input: The molecule is an ethylenediamine derivative that is ethylenediamine in which one of the amino nitrogens is substituted by two methyl groups and the remaining amino nitrogen is substituted by a 4-methoxybenzyl and a pyridin-2-yl group. It has a role as a H1-receptor antagonist. It is an ethylenediamine derivative and an aromatic ether.

Output: COC1=CC=C(CN(CCN(C)C)C2=CC=CC=N2)C=C1


Input: The molecule is a fine white to creamy white powder. A synthetic steroid. Used in combination with progestogen as an oral contraceptive.

Output: C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C


Input: The molecule is a carboxylic ester. It is functionally related to a benzyl alcohol.

Output: C[C@H]1C[C@@H](OC(=O)C(OC(=O)C2=CC=CN=C2)C2=CC=CC=C2)CC(C)(C)C1


Input: The molecule is the (S)-enantiomer of azetidine-2-carboxylic acid. It is an enantiomer of a (R)-azetidine-2-carboxylic acid.

Output: O=C(O)[C@@H]1CCN1


Input: The molecule is a steroid glucuronide anion that is the conjugate base of 17beta-estradiol 3-O-(beta-D-glucuronide) 17-sulfate arising from deprotonation of the carboxylic and sulfate groups; major species at pH 7.3.

Output: C[C@]12CC[C@@H]3C4=CC=C(O[C@@H]5O[C@H](C(=O)[O-])[C@@H](O)[C@H](O)[C@H]5O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2OS(=O)(=O)[O-]


Input: The molecule is an abietane diterpenoid that is abieta-8,11,13-trien-20-al substituted by a hydroxy group at position 12. It has been isolated from the stem bark of Fraxinus sieboldiana. It has a role as a plant metabolite. It is an abietane diterpenoid, an aldehyde, a member of phenols and a tricyclic diterpenoid.

Output: CC(C)C1=CC2=C(C=C1O)[C@@]1(C=O)CCCC(C)(C)[C@@H]1CC2


Input: The molecule is a chlorinated organic chemical due to environmental exposure, that can be detected in breast milk. The free species of phenols and chlorinated organic appear to be most prevalent in milk (A11269).

Output: OC1=CC=C(Cl)C=C1Cl


Input: The molecule is an N-acyl-4-hydroxy-15-methylhexadecasphinganine-1-phosphocholine in which the acyl group has 22 carbons and 0 double bonds. It is functionally related to a 15-methylhexadecaphytosphingosine.

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


Input: The molecule is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts by inducing the release of catecholamine. An important characteristic of this product is its impediment to cross the blood-brain barrier which restrains its side effects to only nonpsychoactive peripheral sympathomimetic effects. There have been reports of hypertensive crisis in patients ingesting tyramine-rich diet in conjunction with monoamine oxidase inhibitors (MAOIs).

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


Input: The molecule is a trihydroxyflavone that is apigenin substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a trihydroxyflavone and a monomethoxyflavone. It derives from an apigenin.

Output: COC1=C(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C1=O


Input: The molecule is a synthetic carbamate ester compound, derived from a methylcarbamic acid and a 3,4-xylenol, and a acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as a white solid, and exposure occurs by inhalation, ingestion, or contact.

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


Input: The molecule is the dianion resulting from the removal of two protons from the phosphate group of pyridoxal 5'-phosphate. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite and a cofactor. It is a conjugate base of a pyridoxal 5'-phosphate.

Output: CC1=NC=C(COP(=O)([O-])[O-])C(C=O)=C1O


Input: The molecule is a pyrimidine nucleoside in which cytosine is attached to ribofuranose via a beta-N(1)-glycosidic bond. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a cytosine.

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


Input: The molecule is a heparin hexasaccharide consisting of 4-deoxy-2-O-sulfo-alpha-L-threo-hex-4-enopyranuronosyl, 2-deoxy-6-O-sulfo-2-(sulfoamino)-alpha-D-glucopyranosyl, alpha-L-idopyranuronosyl, 2-acetamido-2-deoxy-6-O-sulfo-alpha-D-glucopyranosyl, beta-D-glucopyranuronosyl, and 2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-alpha-D-glucopyranose units joined in sequence by 1->4 linkages. Sequence: DUA2S-GlcNS6S-IdoA-GlcNAc6S-GlcA-GlcNS3S6S. It is a heparin hexasaccharide, an amino hexasaccharide and an oligosaccharide sulfate.


Input: The molecule is a butanone that is the 2-methylbutanoyl derivative of phloroglucinol. It has a role as a metabolite. It is a benzenetriol and a butanone. It derives from a phloroglucinol.

Output: CC[C@H](C)C(=O)C1=C(O)C=C(O)C=C1O


Input: The molecule is a propanediol compound with anticonvulsant and antiepileptic properties. Although the exact mechanism of action is unknown, Felbamate may be an antagonist at the strychnine-insensitive glycine-recognition site of the N-methyl-D-aspartate (NMDA) receptor-ionophore complex, thereby blocking the effects of the excitatory amino acids, suppressing neuronal firing, and preventing seizure activity. Felbamate also has weak inhibitory effects on gamma-aminobutyric acid (GABA) receptor binding sites which may contribute to its inhibitory effect on neuronal excitatory.

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


Input: The molecule is one of a family of organophosphorus pesticides. It is combustible though it may require some effort to ignite. It is very toxic by skin absorption and inhalation. It may or may not be water soluble.

Output: CCCSP(=O)(OCC)SCCC


Input: The molecule is an aminonaphthalenesulfonic acid that is 2-naphthalenesulfonic acid substituted by an amino group at position 7 and a hydroxy group at position 4 respectively. It has a role as a metabolite. It is an aminonaphthalenesulfonic acid and a member of naphthols.

Output: NC1=CC=C2C(O)=CC(S(=O)(=O)O)=CC2=C1


Input: The molecule is a metal oxide with formula CeO2. It is used for polishing glass, in coatings for infra-red filters to prevent reflection, and as an oxidant and catalyst in organic synthesis. It is a cerium molecular entity and a metal oxide.

Output: O=[Ce]=O


Input: The molecule is conjugate base of (2S)-2-hydroxyphytanic acid. It is a (2S)-2-hydroxy monocarboxylic acid anion, an isoprenoid and a long-chain fatty acid anion. It is functionally related to a hexadecanoic acid and a hexadecanoate. It is a conjugate base of a (2S)-2-hydroxyphytanic acid.

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


Input: The molecule is a fatty amide obtained by formal condensation of the carboxy group of octadec-9-enoic acid with the amino group of 2-aminopropan-1-ol. It is functionally related to an octadec-9-enoic acid.

Output: CCCCCCCCC=CCCCCCCCC(=O)NC(C)CO


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

Output: O=C(O)C1CSC(C(=O)O)N1


Input: The molecule is an amino hexasaccharide in which an alpha-L-fucosyl residue is linked (1->2) to the mannosyl residue furthest from the reducing end of an alpha-D-GalNAc-(1->3)-beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-beta-D-GlcNAc linear pentasaccharide. It has a role as an epitope. It is a glucosamine oligosaccharide, a galactosamine oligosaccharide and an amino hexasaccharide.


Input: The molecule is an antiallergic drug, clinically effective for atopic diseases, especially allergic asthma and rhinitis. Amlexanox as a topical paste is a well tolerated treatment of recurrent aphthous ulcers. Recurrent aphthous ulcer (RAU) is the most prevalent oral mucosal disease in humans, estimated to affect between 5% and 50% of the general population.

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


Input: The molecule is a member of acridines. It is functionally related to an acridone.

Output: C=C(CCl)C1CC2=C(C=C(O)C3=C2N(C)C2=CC=CC=C2C3=O)O1


Input: The molecule is an epoxy(hydroxy)icosatrienoate that is the conjugate base of (8R)-hydroxy-(11R,12R)-epoxyicosa-(5Z,9E,14Z)-trienoic acid, obtained by deprotonation of the carboxy group. It is a conjugate base of an (8R)-hydroxy-(11R,12R)-epoxyicosa-(5Z,9E,14Z)-trienoic acid.

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


Input: The molecule is a drug used in combination with [DB08820] as the fixed dose combination product Orkambi for the management of Cystic Fibrosis (CF) in patients aged 6 years and older. Cystic Fibrosis is an autosomal recessive disorder caused by one of several different mutations in the gene for the Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) protein, a transmembrane ion channel involved in the transport of chloride and sodium ions across cell membranes of the lungs, pancreas, and other organs. Mutations in the CFTR gene result in altered production, misfolding, or function of the CFTR protein and consequently abnormal fluid and ion transport across cell membranes. As a result, CF patients produce thick, sticky mucus that clogs the ducts of organs where it is produced making patients more susceptible to infections, lung damage, pancreatic insufficiency, and malnutrition. Lumacaftor improves CF symptoms and underlying disease pathology by aiding the conformational stability of F508del-mutated CFTR proteins, preventing misfolding and resulting in increased processing and trafficking of mature protein to the cell surface.   Results from clinical trials indicated that treatment with Orkambi (lumacaftor/ivacaftor) results in improved lung function, reduced chance of experiencing a pulmonary exacerbation, increased weight gain, and improvements in CF symptoms. This data has been heavily scrutinized, however, with clinical trials showing only modest improvements despite a hefty yearly cost of $259,000 for Orkambi. Improvements in lung function (ppFEV1) were found to be statistically significant, but minimal, with only a 2.6-3.0% change from baseline with more than 70% of patients failing to achieve an absolute improvement of at least 5%.  A wide variety of CFTR mutations correlate to the Cystic Fibrosis phenotype and are associated with differing levels of disease severity. The most common mutation, affecting approximately 70% of patients with CF worldwide, is known as F508del-CFTR, or delta-F508 (ΔF508), in which a deletion in the amino acid phenylalanine at position 508 results in impaired production of the CFTR protein, thereby causing a significant reduction in the amount of ion transporter present on cell membranes. When used in combination with [DB08820] as the fixed dose combination product Orkambi, lumacaftor is specific for the management of CF in patients with delta-F508 mutations as it acts as a protein-folding chaperone, aiding the conformational stability of the mutated CFTR protein. Consequently, lumacaftor increases successful production of CFTR ion channels and the total number of receptors available for use at the cell membrane for fluid and ion transport. The next most common mutation, G551D, affecting 4-5% of CF patients worldwide, is characterized as a missense mutation, whereby there is sufficient amount of protein at the cell surface, but opening and closing mechanisms of the channel are altered. Treatment of patients with G551D and other rarer missense mutations is usually managed with [DB08820] (Kalydeco), as it aids with altered gating mechanisms by potentiating channel opening probability of CFTR protein.  Prior to the development of lumacaftor and [DB08820] (Kalydeco), management of CF primarily involved therapies for the control of infections, nutritional support, clearance of mucus, and management of symptoms rather than improvements in the underlying disease process. Approved for use by the Food and Drug Administration in July 2015 and by Health Canada in January 2016, Orkambi was the first combination product approved for the management of Cystic Fibrosis with delta-F508 mutations.  Ivacaftor is manufactured and distributed by Vertex Pharmaceuticals.

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


Input: The molecule is a purine ribonucleoside 5'-triphosphate. It has a role as an antimetabolite, an antifungal agent, an antineoplastic agent and an antiviral agent. It is functionally related to a cordycepin.

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


Input: The molecule is a naturally occurring antioxidant dicatechol originally derived from the creosote bush Larrea divaricatta with antipromoter, anti-inflammatory, and antineoplastic activities. Masoprocol directly inhibits activation of two receptor tyrosine kinases (RTKs), the insulin-like growth factor receptor (IGF-1R) and the c-erbB2/HER2/neu receptor, resulting in decreased proliferation of susceptible tumor cell populations. This agent may induce apoptosis in susceptible tumor cell populations as a result of disruption of the actin cytoskeleton in association with the activation of stress activated protein kinases (SAPKs). In addition, masoprocol inhibits arachidonic acid 5-lipoxygenase (5LOX), resulting in diminished synthesis of inflammatory mediators such as prostaglandins and leukotrienes. It may prevent leukocyte infiltration into tissues and the release of reactive oxygen species.

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


Input: The molecule is under investigation in clinical trial NCT02048709 (Indoleamine 2,3-Dioxygenase (IDO) Inhibitor in Advanced Solid Tumors).

Output: OC1CCC([C@H](O)C[C@H]2C3=C(F)C=CC=C3C3=CN=CN32)CC1


Input: The molecule is a beta-hydroxyketone that is 3-hydroxycyclopentanone in which a hydrogen at position 4 is replaced by a (1E)-4-hydroxy-4-methyloct-1-en-1-yl group and a hydrogen at position 5 is replaced by a 7-methoxy-7-oxoheptyl group. It is a tertiary alcohol, a secondary alcohol, a beta-hydroxy ketone, a cyclic ketone and a methyl ester.

Output: CCCCC(C)(O)C/C=C/C1C(O)CC(=O)C1CCCCCCC(=O)OC


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

Output: CC(=O)C(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 3-hydroxy steroid resulting from deoxygenation at position 17 of estradiol or estrone. It has a role as an estrogen. It is a 3-hydroxy steroid and a member of phenols. It derives from a hydride of an estrane.

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


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

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


Input: The molecule is a methyl ketone that is tridecane in which the methylene hydrogens at position 2 are replaced by an oxo group. It has a role as a plant metabolite and a flavouring agent. It derives from a hydride of a tridecane.

Output: CCCCCCCCCCCC(C)=O


Input: The molecule is a phosphate monoester dianion obtained by deprotonation of the phosphate OH groups of mannose-1D-myo-inositol 1-phosphate; major species at pH 7.3. It is a conjugate base of a mannose-1D-myo-inositol 1-phosphate.

Output: O=P([O-])([O-])O[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O


Input: The molecule is a diterpenoid isolated from the aerial parts of Ajuga bracteosa. It has a role as a plant metabolite and an antifeedant. It is a furofuran, an acetate ester, a diterpenoid, a spiro-epoxide and a cyclic acetal.

Output: CC(=O)OC[C@@]12[C@@H](OC(C)=O)C[C@@H](C)[C@](C)([C@@H]3C[C@H]4CCO[C@H]4O3)[C@H]1C[C@@H](O)[C@H](OC(=O)C(C)C)[C@]21CO1


Input: The molecule is an antiviral agent which targets the DNA terminal transferase complex of the cytomegalovirus (CMV) and which is used to prevent CMV reactivation in immunocompromised patients. Letermovir has been associated with mild-to-moderate serum aminotransferase elevations during therapy but has not been linked to cases of clinically apparent acute liver injury.

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


Input: The molecule is the 3,4-didehydro derivative of D-glucose.

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


Input: The molecule is an orally available prodrug of PSI-6130 which is a selective cytidine nucleoside analogue and non-cytotoxic hepatitis C virus (HCV) polymerase inhibitor. After intracellular uptake, mericitabine is phosphorylated into two active triphosphate metabolites, which disable HCV RNA-dependent RNA polymerase (non-structural protein 5B; NS5B) upon binding. This results in the blockage of viral HCV RNA production and thus viral replication. This agent has a high barrier to resistance, however, a substitution mutation (S282T) on HCV NS5B impairs mericitabine's activity significantly.

Output: CC(C)C(=O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@](C)(F)[C@@H]1OC(=O)C(C)C


Input: The molecule is conjugate base of ascr#31 It is a conjugate base of an ascr#31.

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


Input: The molecule is a member of the class of 7-hydroxyisoflavones that is isoflavone substituted by hydroxy groups at positions 5, 7 and 4' and a prenyl group at position 6. It has been isolated from Ficus mucuso. It has a role as a plant metabolite and an antifungal agent. It derives from an isoflavone.

Output: CC(C)=CCC1=C(O)C=C2OC=C(C3=CC=C(O)C=C3)C(=O)C2=C1O


Input: The molecule is a cyanine dye and an organic potassium salt. It has a role as a fluorochrome. It contains a NIR-2(2-).

Output: CCN1/C(=C\C=C\C=C\C2=[N+](CCCCS(=O)(=O)[O-])C3=CC=C(C(=O)O)C=C3C2(C)C)C(C)(C)C2=C1C=CC1=C(S(=O)(=O)[O-])C=C(S(=O)(=O)[O-])C=C21;[K+];[K+]


Input: The molecule is an acyl-CoA oxoanion that is the tetraanion formed from acetyl-2'-(5"-phosphoribosyl)-3'-dephospho-CoA by global deprotonation of the phosphate and diphosphate groups. Major species at pH 7.3. It is a conjugate base of an acetyl-2'-(5''-phosphoribosyl)-3'-dephospho-CoA.

Output: 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]2O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]2O)[C@@H]1O


Input: The molecule is a ent-kaurane diterpenoid that is ent-kaurane-19-oic acid substituted by hydroxy groups at positions 16 and 17 (the 16beta stereoisomer). It is isolated from Helianthus sp. and Annona squamosa and exhibits anti-HIV activity. It has a role as a metabolite and an anti-HIV agent. It is an ent-kaurane diterpenoid, a hydroxy monocarboxylic acid, a diol, a tertiary alcohol, a primary alcohol and a bridged compound.

Output: C[C@@]12CCC[C@@](C)(C(=O)O)[C@H]1CC[C@@]13C[C@@H](CC[C@H]12)[C@](O)(CO)C3


Input: The molecule is an acyl-CoA(4-) obtained by deprotonation of the phosphate and diphosphate groups of oscr#36-CoA; major species at pH 7.3. It is a conjugate base of an oscr#36-CoA.

Output: C[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCCCCCC(=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 an organic cation obtained by protonation of the imidazole group of (S)-isoconazole. It is a conjugate acid of a (S)-isoconazole. It is an enantiomer of a (R)-isoconazole(1+).

Output: ClC1=CC=C([C@@H](CN2C=CN=C2)OCC2=C(Cl)C=CC=C2Cl)C(Cl)=C1;[H+]


Input: The molecule is a dicarboximide that is 3a,4,7,7a-tetrahydrophthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethyl group. A non-systemic fungicide introduced in the 1950s, it is widely used for the control of fungal diseases in fruits, vegetables, and ornamental crops. It has a role as an antifungal agrochemical. It is a member of isoindoles, an organochlorine compound, an organosulfur compound and a phthalimide fungicide.

Output: O=C1C2CC=CCC2C(=O)N1SC(Cl)(Cl)Cl


Input: The molecule is a member of the class of tetracenequinones that is tetracene-5,12-dione in which the hydrogens at positions 1, 3, 8, 10, and 11 have been replaced by hydroxy groups. Isolated from Paecilomyces. It has a role as an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an antineoplastic agent, a fungal metabolite and an intercalator.

Output: O=C1C2=CC(O)=CC(O)=C2C(=O)C2=C1C=C1C=C(O)C=C(O)C1=C2O


Input: The molecule is the ionic polymer obtained by global deprotonation of the carboxy groups of alginic acid; major species at pH 7.3. It is a carbohydrate acid anion and an ionic polymer. It is a conjugate base of an alginic acid.

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


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

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


Input: The molecule is a phosphatidylcholine O-34:1 in which the alkenyl group at position 1 is (9Z)-octadecenyl and the acyl group at position 2 is hexadecanoyl. It has a role as a mouse metabolite. It is functionally related to a hexadecanoic acid.

Output: CCCCCCCC/C=C\CCCCCCCCOC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC


Input: The molecule is a polyprenylhydroquinone in which the polyprenyl substituent is hexaprenyl at C-2; an additional methoxy group is also present at C-6. It is a 2-methoxy-6-all-trans-polyprenylhydroquinone and a member of hydroquinones.

Output: COC1=CC(O)=CC(C/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CC/C=C(\C)CCC=C(C)C)=C1O


Input: The molecule is a pyrimidine nucleoside comprised of a cytosine bound to ribose via a beta-N1-glycosidic bond. Cytidine is a precursor for uridine. Both cytidine and uridine are utilized in RNA synthesis.

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


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

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


Input: The molecule is an N-acyl-15-methylhexadecasphing-4-enine-1-phosphocholine in which the acyl group has 20 carbons and 0 double bonds. It is functionally related to a 15-methylhexadecasphing-4-enine.

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


Input: The molecule is a Kinase Inhibitor. The mechanism of action of it is as a Kinase Inhibitor, and Cytochrome P450 3A Inhibitor.

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


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 derives from 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 piperidine compound having a (2-thienyl)ethyl substituent at the 1-position, a methyl group at the 3-position and an N-phenylpropanamido group at the 4-position. It has a role as an opioid analgesic. It is a member of piperidines, a member of thiophenes, an anilide and a monocarboxylic acid amide.

Output: CCC(=O)N(C1=CC=CC=C1)C1CCN(CCC2=CC=CS2)CC1C


Input: The molecule is a biphenyl matrix metalloproteinase (MMP) inhibitor (MMPI) with potential antineoplastic activity. Tanomastat inhibits MMP-2, MMP-3, and MMP-9, inhibiting extracellular matrix degradation and potentially inhibiting angiogenesis, tumor growth and invasion, and metastasis. MMPs consist of at least 18 zinc-containing endo-proteinases that are capable of degrading collagen and proteoglycan.

Output: O=C(C[C@H](CSC1=CC=CC=C1)C(=O)O)C1=CC=C(C2=CC=C(Cl)C=C2)C=C1


Input: The molecule is an alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of 5-bromotryptophan; major species at pH 7.3. It is a tautomer of a 5-bromotryptophan.

Output: [NH3+]C(CC1=CNC2=CC=C(Br)C=C12)C(=O)[O-]


Input: The molecule is a contrast agent composed of hyperpolarized xenon Xe 129 gas (HP129Xe), with potential usage in diagnostic nuclear magnetic resonance (NMR)-based imaging (MRI). Upon inhalation, the hyperpolarized xenon 129 gas is distributed throughout the lungs. MRI, immediately following HP129Xe administration, allows for the visualization of lung structures based on the distribution pattern of the gas. This may aid in the diagnosis of certain lung abnormalities. Hyperpolarization of Xe 129 enhances NMR signals and thus improves imaging and assessment of lung function.

Output: [Xe]


Input: The molecule is a dicarboximide that is 4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione in which the nitrogen has been substituted by a 5-(but-3-yn-2-yloxy)-4-chloro-2-fluorophenyl group. It is a dicarboximide, a terminal acetylenic compound, an aromatic ether, a member of monofluorobenzenes, a member of monochlorobenzenes and a pyrroline.

Output: C#CC(C)OC1=CC(N2C(=O)C3=C(CCCC3)C2=O)=C(F)C=C1Cl


Input: The molecule is a long-chain fatty acid that is stearic (octadecanoic) acid substituted at position 2 by a hydroxy group. It has a role as a human metabolite. It is a 2-hydroxy fatty acid and a hydroxyoctadecanoic acid. It is a conjugate acid of a 2-hydroxyoctadecanoate.

Output: CCCCCCCCCCCCCCCCC(O)C(=O)O


Input: The molecule is a member of the class of xanthones that is the 5-O-methyl derivative of bellidifolin. Isolated from Centaurium erythraea and Swertia chirayita, it exhibits hypoglycemic activity. It has a role as a hypoglycemic agent and a metabolite. It is a member of xanthones, an aromatic ether and a member of phenols. It is functionally related to a bellidifolin.

Output: COC1=CC(O)=C2C(=O)C3=C(O)C=CC(OC)=C3OC2=C1


Input: The molecule is an organic anion that is the conjugate base of hispidin resulting from the deprotonation of the 4-hydroxy group; major species at pH 7.3. It is a conjugate base of a hispidin.

Output: O=C1C=C(O)C=C(/C=C/C2=CC=C([O-])C(O)=C2)O1


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

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


Input: The molecule is under investigation in clinical trial NCT01515384 (A Trial of 18F-AV-133 Positron Emission Tomography (PET)).

Output: COC1=CC2=C(C=C1OCCCF)CCN1C[C@@H](CC(C)C)[C@H](O)C[C@H]21


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

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


Input: The molecule is a steroid. It derives from a hydride of a pregnane.

Output: CC(=O)OCC(=O)[C@@]1(O)[C@H](C)C[C@H]2[C@@H]3C=C(C)C4=CC5=C(C=NN5C5=CC=CC=C5)C[C@]4(C)[C@H]3[C@@H](O)C[C@@]21C


Input: The molecule is an acetate ester that is propyl acetate substituted by an ethoxy group at position 3. It is an acetate ester and an ether.

Output: CCOCCCOC(C)=O


Input: The molecule is a phenolate anion obtained by deprotonation of the 2-hydroxy group of (S)-averantin. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.). It has a role as a fungal metabolite. It is a conjugate base of a (S)-averantin.

Output: CCCCC[C@H](O)C1=C(O)C=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1[O-]


Input: The molecule is the organophosphate oxoanion of overall charge -4 formed from undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine at pH 7.3. It is a conjugate base of an undecaprenyldiphospho-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine.


Input: The molecule is a nucleoside 5'-monophosphate(2-) that results from the removal of two protons from the phosphate group of N(6)-methyl-AMP. It derives from an adenosine 5'-monophosphate(2-). It is a conjugate base of a N(6)-methyl-AMP.

Output: CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]1O


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

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


Input: The molecule is a colorless to off-white crystalline solid. Starts turning brown at approximately 329 °F; is blackish-brown at melting point.

Output: C=C1C/C(=C/C)C(=O)O[C@@H]2CCN3CC=C(COC(=O)[C@@]1(O)CO)[C@H]23


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 is functionally related to 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 diterpenoid. It derives from a hydride of an atisane.

Output: CC1(O)CC23C=CC1CC2C1(C)CCC(=O)C(C)(C)C1CC3


Input: The molecule is a docosanoid anion that is the conjugate base of (8E,10Z,13Z,16Z,19Z)-7-oxodocosapentaenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a docosanoid anion, a long-chain fatty acid anion, an oxo fatty acid anion and a polyunsaturated fatty acid anion. It is a conjugate base of an (8E,10Z,13Z,16Z,19Z)-7-oxodocosapentaenoic acid.

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


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

Output: COC1=C(N2CCN[C@H](C)C2)C(F)=CC2=C1N(C1CC1)C=C(C(=O)O)C2=O


Input: The molecule is a member of the class of formamides that is formamide in which one of the amino hydrogens is replaced by a phenyl group. It is a member of formamides and an aromatic amide. It is functionally related to a formamide.

Output: O=CNC1=CC=CC=C1


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

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


Input: The molecule is the stereoconfiguration is based on CHEBI:134612, pmid:20810662 It is functionally related to a staphyloferrin B(2-).

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


Input: The molecule is a ketoaldonic acid. It derives from 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 an oxo monocarboxylic acid anion that is the conjugate base of 5-hydroxy-3-[(3aS,4S,5R,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is an oxo monocarboxylic acid anion, a hydroxy monocarboxylic acid anion and a carbocyclic fatty acid anion. It is a conjugate base of a 3-[(3aS,4S,5R,7aS)-5-hydroxy-7a-methyl-1-oxo-octahydroinden-4-yl]propanoic acid.

Output: C[C@]12CC[C@@H](O)[C@@H](CCC(=O)[O-])[C@@H]1CCC2=O


Input: The molecule is a steroidal acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3-oxochola-4,22-dien-24-oic acid. It is a conjugate acid of a 3-oxochola-4,22-dien-24-oyl-CoA(4-).

Output: C[C@H](/C=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)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C


Input: The molecule is a bifunctional mechlorethamine derivative with alkylating and antimetabolite activities. Although the exact mechanism of action of bendamustine is unknown, this agent appears to alkylate and crosslink macromolecules, resulting in DNA, RNA and protein synthesis inhibition, and eventually the induction of apoptosis.

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


Input: The molecule is the L-alpha-amino acid zwitterion formed from L-4-hydroxyglutamic semialdehyde by transfer of a proton from the carboxy to the amine group; it is the principal microspecies at pH 7.3. It is a tautomer of a L-4-hydroxyglutamic semialdehyde.

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


Input: The molecule is a disaccharide that is alpha-D-arabinopyranose in which the hydroxy group at position 2 has been converted into the corresponding beta-D-glucoside. It is a beta-D-glucoside and a glycosylarabinose. It is functionally related to an alpha-L-arabinopyranose.

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


Input: The molecule is a 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration. It has a role as a xenoestrogen. It is a 17-hydroxy steroid, a terminal acetylenic compound and a 3-hydroxy steroid. It is functionally related to a 17beta-estradiol and an estradiol.

Output: C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C


Input: The molecule is a 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol in which the 2-acyl group is specified as (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl (arachidonoyl). It has a role as a mouse metabolite. It is a 1-octadecanoyl-2-acyl-sn-glycero-3-phospho-1D-myo-inositol and a phosphatidylinositol(18:0/20:4). It derives from an octadecanoic acid and an arachidonic acid. It is a conjugate acid of a 1-octadecanoyl-2-arachidonoyl-sn-glycero-3-phospho-D-myo-inositol(1-).

Output: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)COP(=O)(O)OC1[C@H](O)[C@H](O)C(O)[C@H](O)[C@H]1O


Input: The molecule is the D-enantiomer of pinitol. It has a role as a geroprotector and a member of compatible osmolytes. It is functionally related to a 1D-chiro-inositol. It is an enantiomer of a L-pinitol.

Output: COC1[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]1O


Input: The molecule is a vinca alkaloid compound and semi-synthetic vincristine derivative with antineoplastic activity. Vinepidine binds to and stabilizes tubulin, thereby preventing tubulin polymerization and depolymerization, which result in microtubule assembly and disassembly, respectively. Treated cells are unable to complete mitosis process and are arrested in the metaphase, thereby leading to an inhibition of cell growth.

Output: CC[C@H]1C[C@@H]2CN(CCC3=C(NC4=CC=CC=C34)[C@@](C(=O)OC)(C3=CC4=C(C=C3OC)N(C=O)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1


Input: The molecule is an adenosine bisphosphate having monophosphate groups at the 2'- and 5'-positions and a sulfo group attached to the phosphate at position 5'. It is functionally related to an adenosine 2',5'-bisphosphate and a 5'-adenylyl sulfate.

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


Input: The molecule is the (S)-enantiomer of N-(butan-2-yl)-6-chloro-N'-ethyl-1,3,5-triazine-2,4-diamine.

Output: CCNC1=NC(Cl)=NC(N[C@@H](C)CC)=N1


Input: The molecule is an Alkylating Drug. The mechanism of action of it is as an Alkylating Activity.

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


Input: The molecule is a steroid sulfate that is lithocholic acid in which the hydroxy hydrogen at position 3 has been replaced by a sulfo group. It derives from a lithocholic acid. It is a conjugate acid of a lithocholate sulfate(2-).

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


Input: The molecule is a single-stranded DNA polynucleotide consisting of a repeating sequence of one thymidine residue and two deoxycytidine residues, with all residues connected by 3'->5' phosphodiester linkages.

Output: CC1=CN([C@H]2C[C@H](OP(=O)(O)OC[C@H]3O[C@@H](N4C=CC(N)=NC4=O)C[C@@H]3OP(=O)(O)OC[C@H]3O[C@@H](N4C=CC(N)=NC4=O)C[C@@H]3O)[C@@H](COP(=O)(O)O)O2)C(=O)NC1=O


Input: The molecule is a pyridoisoquinoline consisting of emetine having a fully aromatised isoquinoline. It is functionally related to an emetine.

Output: CC[C@H]1CN2CCC3=CC(OC)=C(OC)C=C3[C@@H]2C[C@@H]1CC1=NC=CC2=CC(OC)=C(OC)C=C12


Input: The molecule is a 1,2-diacyl-sn-glycerol 3-phosphate in which the acyl substituents at positions 1 and 2 are specified as linoleoyl and oleoyl respectively. It derives from an oleic acid and a linoleic acid. It is a conjugate acid of a 1-linoleoyl-2-oleoyl-sn-glycero-3-phosphate(2-).

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


Input: The molecule is a 4-(1-hydroxy-2-{[4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl)phenol in which the carbon bearing the hydroxy group has R configuration while the remaining stereocentre has S configuration. It is an enantiomer of a 4-[(1S)-1-hydroxy-2-{[(2R)-4-(4-hydroxyphenyl)butan-2-yl]amino}ethyl]phenol.

Output: C[C@@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C1=CC=C(O)C=C1


Input: The molecule is a N-glycosyl compound, a ribose monophosphate, a member of imidazoles and a monocarboxylic acid. It is a conjugate acid of a [1-(5-phosphonatoribosyl)imidazol-4-yl]acetate(3-).

Output: O=C(O)CC1=CN(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=N1


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

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


Input: The molecule is an orally available, long-acting inhibitor of phosphodiesterase (PDE) type 4 (PDE4), with anti-inflammatory and potential antineoplastic activities. Upon administration, roflumilast and its active metabolite roflumilast N-oxide selectively and competitively bind to and inhibit PDE4, which leads to an increase of both intracellular levels of cyclic-3',5'-adenosine monophosphate (cAMP) and cAMP-mediated signaling. cAMP prevents phosphorylation of spleen tyrosine kinase (SYK) and abrogates activation of the PI3K/AKT/mTOR signaling pathway, which may result in the induction of apoptosis. PDE4, a member of the PDE superfamily that hydrolyses cAMP and 3',5'-cyclic guanosine monophosphate (cGMP) to their inactive 5' monophosphates, is upregulated in a variety of cancers and may contribute to chemoresistance; it also plays a key role in inflammation, especially in inflammatory airway diseases.

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


Input: The molecule is a carboxy-2-hydroxymuconate semialdehyde having the carboxy group at the 4-position and the aldehyde functijon at the 6-position. It is a conjugate acid of a 4-carboxy-2-hydroxy-cis,cis-muconate 6-semialdehyde(2-).

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


Input: The molecule is a tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and a prenyl group at position 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant activities. It has a role as a metabolite, an anti-inflammatory agent, an antibacterial agent and a radical scavenger. It is a tetrahydroxyflavanone and a member of 4'-hydroxyflavanones. It is functionally related to a (2S)-flavanone.

Output: CC(C)=CCC1=CC([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O


Input: The molecule is a gamma-amino acid that is gamma-aminobutyric acid (GABA) carrying an isobutyl substitutent at the beta-position (the S-enantiomer). Binds with high affinity to the alpha2-delta site (an auxiliary subunit of voltage-gated calcium channels) in central nervous system tissues. It has a role as an anticonvulsant and a calcium channel blocker. It is functionally related to a gamma-aminobutyric acid.

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


Input: The molecule is a tetrahydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' and a prenyl group at position 5'. Isolated from Erythrina sigmoidea, it exhibits anti-inflammatory and antioxidant activities. It has a role as a metabolite, an anti-inflammatory agent, an antibacterial agent and a radical scavenger. It is a tetrahydroxyflavanone and a member of 4'-hydroxyflavanones. It derives from a (2S)-flavanone.

Output: CC(C)=CCC1=CC([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O


Input: The molecule is an oxo monocarboxylic acid anion that is the conjugate base of 5-hydroxy-3-[(3aS,4S,5R,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is an oxo monocarboxylic acid anion and a hydroxy monocarboxylic acid anion. It is a conjugate base of a 3-[(3aS,4S,5R,7aS)-5-hydroxy-7a-methyl-1,5-dioxo-octahydroinden-4-yl]propanoic acid.

Output: C[C@]12CC[C@@H](O)[C@@H](CCC(=O)[O-])[C@@H]1CCC2=O


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

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


Input: The molecule is an organic cation that is the conjugate acid of trypanothione, arising from deprotonation of the carboxy groups and protonation of the primary and secondary amino groups; major species at pH 7.3. It is a conjugate acid of a trypanothione.

Output: [NH3+][C@@H](CCC(=O)N[C@@H](CS)C(=O)NCC(=O)NCCCC[NH2+]CCCNC(=O)CNC(=O)[C@H](CS)NC(=O)CC[C@H]([NH3+])C(=O)[O-])C(=O)[O-]


Input: The molecule appears as a colorless or slightly yellow fuming liquid with a pungent and irritating odor resembling that of hydrochloric acid. Causes severe burns to skin, eyes and mucous membranes. Very toxic by inhalation, ingestion and skin absorption. Reacts with water to evolve hydrochloric acid, an irritating and corrosive gas apparent as white fumes. Used during electrodeposition of metal on rubber and for making pesticides, surfactants, gasoline additives, plasticizers, dyestuffs, textile finishing agents, germicides, medicinal products, and other chemicals.

Output: ClP(Cl)Cl


Input: The molecule is an orally available, compact macrocyclic structure-based inhibitor of the receptor tyrosine kinase (RTK) anaplastic lymphoma kinase (ALK), with potential antineoplastic activity. Upon oral administration, ALK inhibitor TPX-0131 binds within the ATP binding boundary and inhibits ALK wild-type tyrosine kinase, ALK fusion proteins and numerous ALK point mutations, including acquired resistance mutations, such as the solvent front mutation (SFM) G1202R and compound mutations L1196M/G1202R, L1198F/G1202R, L1196M/L1198F, and C1156Y/G1202R. Inhibition of ALK leads to the disruption of ALK-mediated signaling and the inhibition of cell growth in ALK-expressing tumor cells. ALK belongs to the insulin receptor superfamily and plays an important role in nervous system development. ALK is not expressed in healthy adult human tissue but ALK dysregulation and gene rearrangements are associated with a variety of tumor cell types. Compared to other ALK inhibitors, TPX-0131 is able to inhibit ALK resistance mutations associated with acquired resistance to other ALK inhibitors.

Output: CC1(C)COC2=CC=C(F)C=C2CN2C3=NC4=C(C=NN4C=C3OC[C@H]2C(F)F)C(=O)N1


Input: The molecule is an indolylmethylglucosinolate that is the conjugate base of neoglucobrassicin, obtained by deprotonation of the sulfo group. It is a conjugate base of a neoglucobrassicin.

Output: CON1C=C(C/C(=N/OS(=O)(=O)[O-])S[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C21


Input: The molecule is a tetrapeptide composed of L-alanine, glycine, L-alanine, and glycine residues joined in sequence by peptide linkages. It is functionally related to a L-alanine and a glycine.

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


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

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


Input: The molecule is under investigation in clinical trial NCT01378377 (Combination Trial of Pimasertib (MSC1936369B) With Temsirolimus).

Output: O=C(NC[C@H](O)CO)C1=CC=NC=C1NC1=CC=C(I)C=C1F


Input: The molecule is a 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one that has (R)-configuration (the racemate is warfarin, an anticoagulant drug and rodenticide). It is a conjugate acid of a (R)-warfarin(1-). It is an enantiomer of a (S)-warfarin.

Output: CC(=O)C[C@H](C1=CC=CC=C1)C1=C(O)C2=CC=CC=C2OC1=O


Input: The molecule is a polyunsaturated fatty acyl-CoA(4-) arising from deprotonation of the phosphate and diphosphate functions of (19Z,22Z,25Z,28Z)-tetratriacontatetraenoyl-CoA. It is a polyunsaturated fatty acyl-CoA(4-), a very long-chain acyl-CoA(4-) and a 3-substituted propionyl-CoA(4-). It is a conjugate base of a (19Z,22Z,25Z,28Z)-tetratriacontatetraenoyl-CoA.

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


Input: The molecule is the streptothricin acid obtained by hydrolysis of the lactam group of streptothricin D. It is a conjugate base of a streptothricin D acid (pH 7.3).

Output: NCCC[C@H](N)CC(=O)NCCC[C@H](N)CC(=O)NCCC[C@H](N)CC(=O)N[C@@H]1[C@H](O)[C@@H](OC(N)=O)[C@@H](CO)O[C@H]1NC1=N[C@H](C(=O)O)[C@@H]([C@H](O)CN)N1


Input: The molecule is made by reacting chlorine gas with a substance called camphene. The resulting product (toxaphene) is a mixture of hundreds of different chlorinated camphenes and related chemicals.

Output: C=C1C(CCl)(CCl)C2(Cl)C(Cl)C(Cl)C1(Cl)C2(Cl)Cl


Input: The molecule is dianion of dTDP-D-fucose arising from deprotonation of the diphosphate OH groups; major species at pH 7.3. It is a conjugate base of a dTDP-D-fucose.

Output: CC1=CN([C@H]2C[C@H](O)[C@@H](COP(=O)([O-])OP(=O)([O-])OC3O[C@H](C)[C@H](O)[C@H](O)[C@H]3O)O2)C(=O)NC1=O


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 derives from a D-penicillamine.

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


Input: The molecule is a HPETE anion. It is a conjugate base of a 9-HPETE.

Output: CCCCC/C=C\C/C=C\CC(/C=C/C=C\CCCC(=O)[O-])OO


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 derives from 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 a cyanoamino acid that is the 3-cyano-derivative of L-alanine. It has a role as an Escherichia coli metabolite, a human metabolite and a mouse metabolite. It is a cyanoamino acid and a non-proteinogenic L-alpha-amino acid. It is a conjugate acid of a 3-cyano-L-alaninate. It is a tautomer of a 3-cyano-L-alanine zwitterion.

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


Input: The molecule is an analog of paclitaxel with antineoplastic activity.  10-Deacetyltaxol binds to and stabilizes the resulting microtubules, thereby inhibiting microtubule disassembly which results in cell- cycle arrest at the G2/M phase and apoptosis.

Output: CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)C4=CC=CC=C4)C4=CC=CC=C4)C[C@@](O)([C@@H](OC(=O)C4=CC=CC=C4)[C@H]21)C3(C)C


Input: The molecule is an organophosphate oxoanion. It is functionally related to an adenosine 5'-monophosphate.

Output: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OC(=O)[C@@H](N)CC2=CNC3=CC=CC=C23)[C@@H](O)[C@H]1O


Input: The molecule is a hydroxy fatty acid that is octadecanoic acid carrying a hydroxy group at position 10. It has a role as a bacterial xenobiotic metabolite. It is a hydroxy fatty acid and a long-chain fatty acid. It derives from an octadecanoic acid. It is a conjugate acid of a 10-hydroxyoctadecanoate.

Output: CCCCCCCCC(O)CCCCCCCCC(=O)O


Input: The molecule is a dipeptide composed of L-asparagine and L-aspartic acid joined by a peptide linkage. It has a role as a metabolite. It is functionally related to a L-asparagine and a L-aspartic acid.

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


Input: The molecule is the prednisolone ester of chlorambucil and nitrogen mustard alkylating agent with antineoplastic activity. Prednimustine itself is not cytotoxic, however, it becomes cytotoxic upon hydrolysis by serum esterases to chlorambucil. Therefore, the increased potency of prednimustine is linked to the prolonged availability of free chlorambucil.

Output: C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1


Input: The molecule is guanosine substituted at the purine 8-position by a hydroxy group. It is used as a biomarker of oxidative DNA damage. It has a role as a biomarker.

Output: NC1=NC2=C(NC(=O)N2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1


Input: The molecule is a C3 cyanine dye having 1-ethyl-3,3-dimethylindoleinine units at each end. It has a role as a fluorochrome. It is a cyanine dye and an organic iodide salt. It contains a C3-indocyanine cation.

Output: CCN1/C(=C/C=C/C2=[N+](CC)C3=CC=CC=C3C2(C)C)C(C)(C)C2=CC=CC=C21;[I-]


Input: The molecule is a pyridinethione that is pyridine-2(1H)-thione in which the hydrogen attached to the nitrogen is replaced by a hydroxy group. It is a Zn(2+) ionophore; the zinc salt is used as an antifungal and antibacterial agent. It has a role as an ionophore. It is a pyridinethione and a monohydroxypyridine. It is a tautomer of a pyridine-2-thiol N-oxide.

Output: ON1C=CC=CC1=S


Input: The molecule is a trihydroxyflavanone that is hesperetin substituted by a prenyl group at position 8. Isolated from Macaranga conifera, it exhibits inhibitory activity against breast cancer resistance protein. It has a role as a metabolite and a breast cancer resistance protein inhibitor. It is a trihydroxyflavanone, a monomethoxyflavanone, a member of 3'-hydroxyflavanones and a member of 4'-methoxyflavanones. It derives from a hesperetin.

Output: COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C(CC=C(C)C)=C3O2)C=C1O


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-beta1-6-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 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 derives from a nor-toralactone.

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


Input: The molecule is a secondary amino compound consisting of two molecules of tacrine that are linked together through their exocyclic amino groups by a heptane-1,7-diyl chain. Bis(7)-tacrine is an acetylcholinesterase (AChE)inhibitor (IC50 0.40 nM, >1,000 times more potent than tacrine). It has also been found to protect against H2O2 -induced apoptosis in rat pheochromocytoma cells. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a neuroprotective agent, an EC 1.14.13.39 (nitric oxide synthase) inhibitor and an apoptosis inhibitor. It derives from a tacrine.

Output: C1=CC=C2C(NCCCCCCCNC3=C4CCCCC4=NC4=CC=CC=C34)=C3CCCCC3=NC2=C1


Input: The molecule appears as a colorless liquid. Less dense than water. Flash point of 170 °F. Very irritating to skin and eyes, and may be toxic by ingestion. Used to make soaps, dyes, and pharmaceuticals.

Output: NCCCNCCCN


Input: The molecule is a non-proteinogenic alpha-amino acid that is the sulfoximine derivative of methionine. It is a methionine derivative, a sulfoximide and a non-proteinogenic alpha-amino acid.

Output: CS(=N)(=O)CCC(N)C(=O)O


Input: The molecule is a disaccharide phosphate. It has a role as an Escherichia coli metabolite. It derives from a sucrose. It is a conjugate acid of a sucrose 6(F)-phosphate(2-).

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


Input: The molecule is a polymer composed of PEG-ylated sorbitan, where the total number of poly(ethylene glycol) units is 20 (w + x + y + z = 20) and a single terminal is capped by an oleoyl group. It has a role as a nonionic surfactant.

Output: CCCCCCCC/C=C\CCCCCCCC(=O)OCCOCC(OCCO)[C@H]1OCC(OCCO)[C@H]1OCCO


Input: The molecule is a ketohexose monophosphate. It is a conjugate acid of a D-arabino-hex-3-ulose 6-phosphate(2-).

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


Input: The molecule is a broad spectrum antibiotic introduced into clinical practice in 1948, but which was subsequently shown to cause serious and fatal aplastic anemia and is now used rarely and reserved for severe, life-threatening infections for which other antibiotics are not available. Chloramphenicol has also been linked to cases of acute, clinically apparent liver injury with jaundice, largely in association with aplastic anemia.

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 branched-chain fatty acid that is 4-methylpentanoic acid carrying an oxo substituent at C-3. It is a branched-chain fatty acid and a 3-oxo fatty acid. It derives from a valeric acid. It is a conjugate acid of a 4-methyl-3-oxopentanoate.

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


Input: The molecule is a fatty amide obtained by formal condensation of the carboxy group of octadec-9-enoic acid with the amino group of 2-aminopropan-1-ol. It derives from an octadec-9-enoic acid.

Output: CCCCCCCCC=CCCCCCCCC(=O)NC(C)CO


Input: The molecule is an organophosphate oxoanion obtained by deprotonation of the phosphate and diphosphate OH groups of alpha-NADPH; major species at pH 7.3. It is a conjugate base of an alpha-NADPH.

Output: NC(=O)C1=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)C=CC1


Input: The molecule is the D-enantiomer of pinitol. It has a role as a member of compatible osmolytes. It derives from a 1D-chiro-inositol. It is an enantiomer of a L-pinitol.

Output: COC1[C@@H](O)[C@@H](O)C(O)[C@H](O)[C@H]1O


Input: The molecule is a C-glycosyl compound that is isovitexin substituted at positions 4 and 7 by beta-glucosyl 6-O-sinapoylglucosyl residues respectively It has a role as a metabolite. It is a C-glycosyl compound, a monohydroxyflavone, a cinnamate ester, a glycosyloxyflavone and a beta-D-glucoside. It is functionally related to a trans-sinapic acid and an isovitexin.

Output: COC1=CC(/C=C/C(=O)OC[C@H]2OC(OC3=CC4=C(C(O)=C3[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)C=C(C3=CC=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C=C3)O4)[C@H](O)[C@@H](O)[C@@H]2O)=CC(OC)=C1O


Input: The molecule is a member of the class of resorcinols carrying an additional 2-phenylethyl substituent at position 5. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a member of resorcinols and a diphenylethane.

Output: OC1=CC(O)=CC(CCC2=CC=CC=C2)=C1


Input: The molecule is a Photinus luciferin. It has a role as a member of oxidized luciferins. It is a conjugate acid of an oxidized Photinus luciferin(1-).

Output: O=C1CSC(C2=NC3=CC=C(O)C=C3S2)=N1


Input: The molecule is a monocarboxylic acid anion that is the conjugate base of N-[(15S)-hydroperoxy-(5Z,8Z,11Z,13E)-icosatetraenoyl]-gamma-aminobutanoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3. It is a monocarboxylic acid anion, a N-acyl-gamma-aminobutyrate and an oxidized N-(fatty acyl)-gamma-aminobutyrate(1-). It is a conjugate base of a N-[(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-icosatetraenoyl]-gamma-aminobutyric acid.

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


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 derives from a tricosanoic acid.

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


Input: The molecule is a tirucallane triterpenoid that is (13alpha,14beta,17alpha,20S)-lanosta-2,7-dien-1-one substituted by an oxo group at position 1. It has been isolated from the stem and stem barks of Cornus walteri. It has a role as a plant metabolite. It is a tirucallane triterpenoid, a cyclic terpene ketone and an enone.

Output: CC(C)CCC[C@H](C)[C@@H]1CC[C@]2(C)C3=CC[C@H]4C(C)(C)C=CC(=O)[C@]4(C)[C@H]3CC[C@@]12C


Input: The molecule is a nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical development for the treatment of acute myeloid leukemia (AML). It has a role as an antimetabolite, an antineoplastic agent, a prodrug and a DNA synthesis inhibitor. It is a nucleoside analogue, a nitrile and a secondary carboxamide. It derives from a hexadecanoic acid and a CNDAC.

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


Input: The molecule is a 26-hydroxy steroid and a 20-hydroxy steroid. It is functionally related to an ecdysone.

Output: CC(O)(CO)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C


Input: The molecule is an orally available dual kinase inhibitor of the receptor tyrosine kinase anaplastic lymphoma kinase (ALK) and focal adhesion kinase (FAK), with potential antineoplastic activity. Upon administration, ALK-FAK inhibitor CEP-37440 selectively binds to and inhibits ALK kinase and FAK kinase. The inhibition leads to disruption of ALK- and FAK-mediated signal transduction pathways and eventually inhibits tumor cell growth in ALK- and FAK-overexpressing tumor cells. ALK belongs to the insulin receptor superfamily and plays an important role in nervous system development; its dysregulation and gene rearrangements are associated with a variety of tumors. The cytoplasmic tyrosine kinase FAK, a signal transducer for integrins, is upregulated and constitutively activated in various tumor types; it plays a key role in tumor cell migration, proliferation, survival, and tumor angiogenesis.

Output: CNC(=O)C1=CC=CC=C1NC1=NC(NC2=CC=C3C[C@@H](N4CCN(CCO)CC4)CCCC3=C2OC)=NC=C1Cl


Input: The molecule is a bile acid glycine conjugate that is glycodeoxycholic acid in which the hydroxy hydrogen at position 3 has been replaced by a sulfo group. It is a bile acid glycine conjugate, a 12alpha-hydroxy steroid and a steroid sulfate. It derives from a glycodeoxycholic acid.

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


Input: The molecule is a pyrazine that is substituted by an acetyl group at position 2. It has been identified as one of the volatile flavor constituents in popcorn, bread crust, vinegar, and potato snacks. It has a role as a flavouring agent. It is an aromatic ketone and a member of pyrazines.

Output: CC(=O)C1=CN=CC=N1


Input: The molecule is a highly selective dopamine transporter antagonist. It was synthesized in the late 1970s and developed as a potential treatment for depression. Vanoxerine was later evaluated as a potential treatment for cocaine addiction due to its ability to block dopamine reuptake with a slower dissociation rate than cocaine. Although several studies have suggested that the profile of vanoxerine is safer than that of cocaine, other studies have found that vanoxerine has at least moderate potential to be abused by humans. More recently, vanoxerine was tested as a potential anti-arrhythmic and anti-atrial fibrillatory agent due to its ability to block the hKV11.1 (hERG) cardiac potassium channel. Vanoxerine is an investigational drug and has not been approved for therapeutic use.

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


Input: The molecule is a polyazaalkane. It has a role as an algal metabolite and a plant metabolite. It is a conjugate base of a bis(3-azaniumylpropyl)azanium.

Output: NCCCNCCCN


Input: The molecule is a tetrapeptide composed of L-alanine, L-phenylalanine, L-threonine, and L-serine joined in sequence by peptide linkages. It has a role as a metabolite. It is functionally related to a L-alanine, a L-phenylalanine, a L-threonine and a L-serine.

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


Input: The molecule is an orally available inhibitor of indoleamine 2,3-dioxygenase 1 (IDO1), with potential immunomodulating and antineoplastic activities. Upon administration, navoximod targets and binds to IDO1, a cytosolic enzyme responsible for the oxidation of the essential amino acid tryptophan into kynurenine. By inhibiting IDO1 and decreasing kynurenine in tumor cells, this agent increases tryptophan levels, restores the proliferation and activation of various immune cells, including dendritic cells (DCs), natural killer (NK) cells, and T-lymphocytes, and causes a reduction in tumor-associated regulatory T-cells (Tregs). Activation of the immune system, which is suppressed in many cancers, may induce a cytotoxic T-lymphocyte (CTL) response against the IDO1-expressing tumor cells. IDO1 is overexpressed by a variety of tumor cell types and plays an important role in immunosuppression. Tryptophan depletion is associated with immunosuppression caused by T-cell suppression.

Output: OC1CCC([C@H](O)C[C@H]2C3=C(F)C=CC=C3C3=CN=CN32)CC1


Input: The molecule is an astatine molecular entity, a hydrogen halide and a mononuclear parent hydride. It is a conjugate acid of an astatide.

Output: [AtH]


Input: The molecule is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone with additional hydroxy groups at positions 5, 3' and 4' and a prenyl group at position 2'. Isolated from the roots of Psorothamnus arborescens, it exhibits antileishmanial activity. It has a role as a metabolite and an antileishmanial agent.

Output: CC(C)=CCC1=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=CC(O)=C1O


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 is functionally related to 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 zwitterionic form of E64, a compound isolated from Aspergillus japonicus, resulting from transfer of a proton from the carboxy to the guanidino group; major species at pH 7.3. It is a tautomer of an E64.

Output: CC(C)C[C@H](NC(=O)[C@H]1O[C@@H]1C(=O)[O-])C(=O)NCCCC[NH+]=C(N)N


Input: The molecule is a 2'-deoxycytidine phosphate having cytosine as the nucleobase. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a 2'-deoxycytidine phosphate and a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate. It is a conjugate acid of a dCTP(3-).

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


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 derives from a (5Z,8Z,11Z)-icosatrienoic acid.

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


Input: The molecule is dianion of hydroxypyruvaldehyde phosphate arising from deprotonation of both of the phosphate OH groups. It is a conjugate base of a hydroxypyruvaldehyde phosphate.

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


Input: The molecule is the anion obtained from global deprotonation of the phosphate OH groups of myo-inositol 1,3,4,5,6-pentakisphosphate; major species at pH 7.3. It has a role as a human metabolite and a Saccharomyces cerevisiae metabolite. It is a conjugate base of a myo-inositol 1,3,4,5,6-pentakisphosphate.

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


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

Output: CC1=CC=CC(N2C[C@H](CO)OC2=O)=C1


Input: The molecule is an organophosphate oxoanion. It is functionally related to an adenosine 5'-monophosphate and a trans-4-coumarate.

Output: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OC(=O)/C=C/C2=CC=C(O)C=C2)[C@@H](O)[C@H]1O


Input: The molecule is an organochlorine compound comprising 2'-deoxyguanosine having a chloro substituent at position 8 of the guanine ring system. It is a member of guanosines and an organochlorine compound.

Output: NC1=NC2=C(N=C(Cl)N2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1


Input: The molecule is an imidazopyridine having norleucine and ornithine residues attached via their side-chains at the 4- and 2-positions respectively. It has a role as a cross-linking reagent and a biomarker. It is an imidazopyridine and a non-proteinogenic L-alpha-amino acid.

Output: N[C@@H](CCCCN1C=CC=C2N=C(NCCC[C@H](N)C(=O)O)N=C21)C(=O)O


Input: The molecule is a member of the family of dapdiamides consisting of 3-aminoalanylvaline, in which the N-terminus is acylated by a 3-carbamoyloxirane-2-carbonyl group. NB Although the relative configuration of the epoxide moiety has been assigned as trans, it has not yet been established whether the absolute configuration is R,R (as drawn) or S,S. It is a dapdiamide and an epoxide. It is a tautomer of a dapdiamide E zwitterion.

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


Input: The molecule is a fifteen-membered glycopeptide comprising glycyl, 3-(1,3-thiazol-4-yl)alanyl, alanyl, glycyl, 4-pyridylalanyl, (5R)-5-(beta-D-galactopyranosyloxy)lysyl, glycyl. alpha-glutamyl, glutaminyl, glycyl, prolyl, lysyl, glycyl, alpha-glutamyl and threonine residues coupled in sequence.


Input: The molecule is a heme that consists of sirohaem lacking the two carboxy groups at positions 12 and 18. It has a role as a bacterial metabolite. It is a conjugate acid of a 12,18-didecarboxysiroheme(6-).

Output: CC1=C(CCC(=O)O)C2=CC3=C(CCC(=O)O)C(C)=C(C=C4N=C(C=C5[N-]C(=CC1=N2)[C@@H](CCC(=O)O)[C@]5(C)CC(=O)O)[C@@H](CCC(=O)O)[C@]4(C)CC(=O)O)[N-]3;[Fe]


Input: The molecule is a glycosylarabinose consisting of D-mannopyranose and D-arabinofuranose joined in sequence by a (1->5) glycosidic bond. It is a glycosylarabinose and a partially-defined glycan. It is functionally related to a D-mannopyranose and a D-arabinofuranose.

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


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

Output: [Xe]


Input: The molecule is a branched amino hexasaccharide, which is a constituent of human breast milk. It is an amino hexasaccharide and a glucosamine oligosaccharide.


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 is functionally related to an icosanoic acid.

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


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

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


Input: The molecule is a carotenoid ether that is spirilloxanthin substituted at position 2 by a hydroxy group. It is a carotenoid ether and a carotenol. It is functionally related to a spirilloxanthin.

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)/C=C/C=C(C)/C=C/C(O)C(C)(C)OC


Input: The molecule is an organic heterotetracyclic compound resulting from cyclocondensation of the 4- and 5-hydroxy groups of (2R,4S)-2-(4-methoxyphenyl)-6,8-dimethyl-3,4-dihydro-2H-chromene-4,5,7-triol across the 1- and 2-positions of beta-D-glucopyranose. It is a natural product extracted from the fern plant, Pronephrium penangianum and exerts antiproliferative and antifibrotic activity. It has a role as an antioxidant and a plant metabolite. It is an organic heterotetracyclic compound, a polycyclic ether, a member of methoxybenzenes, a monosaccharide derivative and a hydroxyflavan. It is functionally related to a beta-D-glucose.

Output: CCC1OC2OC3=C(C)C(O)=C(C)C4=C3C(C[C@H](C3=CC=C(OC)C=C3)O4)OC2C(O)C1O


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 is functionally related to 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 primarily available as the sodium salt.

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


Input: The molecule is a nucleobase analogue that is cytosine in which the hydrogen at position 5 is replaced by a hydroxymethyl group. It has a role as a human metabolite and a mouse metabolite. It is an aminopyrimidine, a nucleobase analogue, a pyrimidone and an aromatic primary alcohol. It derives from a cytosine.

Output: NC1=C(CO)C=NC(=O)N1


Input: The molecule is the simplest of the sulfamic acids consisting of a single sulfur atom covalently bound by single bonds to two amino groups and by double bonds to two oxygen atoms.

Output: NS(N)(=O)=O


Input: The molecule is under investigation in clinical trial NCT03394027 (ONC201 in Recurrent/Refractory Metastatic Breast Cancer and Advanced Endometrial Carcinoma).

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


Input: The molecule is a member of the class of benzoxaboroles that is 5-hydroxy-1,3-dihydro-2,1-benzoxaborole in which the phenolic hydrogen has been replaced by a 4-cyanophenyl group. A phosphodiesterase 4 inhibitor that is used for treatment of mild to moderate atopic dermatitis in children and adults. It has a role as a phosphodiesterase IV inhibitor, an antipsoriatic and a non-steroidal anti-inflammatory drug. It is a benzoxaborole, an aromatic ether and a nitrile.

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


Input: The molecule is a selective cyclin-dependent kinase inhibitor, a class of drugs that help slow the progression of cancer by inhibiting two proteins called cyclin-dependent kinase 4 and 6 (CDK4/6). These proteins, when over-activated, can enable cancer cells to grow and divide too quickly. Targeting CDK4/6 with enhanced precision may play a role in ensuring that cancer cells do not continue to replicate uncontrollably. Ribociclib was approved by the U.S. FDA in March, 2017 as Kisqali.

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


Input: The molecule is an alkane-alpha,omega-diammonium(2+) that is the dication of 2-hydroxyputrescine arising from protonation of both primary amino groups; major species at pH 7.3. It is functionally related to a 1,4-butanediammonium. It is a conjugate acid of a 2-hydroxyputrescine.

Output: [NH3+]CCC(O)C[NH3+]


Input: The molecule is a steroid. It derives from a hydride of an estrane.

Output: C[C@@]12C=CC[C@H]1[C@@H]1CCC3=CC(OC(=O)C4=CC=CC=C4)=CC=C3[C@H]1CC2


Input: The molecule is a new agent under investigation for the treatment of patients with type 2 diabetes. It belongs to a novel class of drugs that target the peroxisome proliferator-activated receptors, both alpha and gamma subtypes. In addition to improvements in blood glucose and hemoglobin A1c (HbA1c), muraglitazar treatment is associated with a substantial reduction in triglycerides (TGs), an increase in HDL-C, and a modest decrease in LDL-C levels.

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


Input: The molecule is a radioisotope of xenon, an element with 54 protons, having gamma emissions and a physical half-life of 5.27 days. Xenon-133 is used in the study of pulmonary function and organ blood flow.

Output: [Xe]


Input: The molecule is a purine ribonucleoside 5'-triphosphate. It has a role as an antimetabolite, an antifungal agent, an antineoplastic agent and an antiviral agent. It derives from a cordycepin.

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


Input: The molecule is a spermidine alkaloid that is isolated from Maytenus heterophylla and Maytenus senegalensis. It has a role as a plant metabolite. It is a spermidine alkaloid, a lactam, an enamide, a secondary carboxamide and a tertiary carboxamide.

Output: O=C1C[C@@H](C2=CC=CC=C2)NCCCCN(C(=O)/C=C/C2=CC=CC=C2)CCCN1


Input: The molecule is an orally bioavailable stimulator of soluble guanylate cyclase (sGC), with potential anti-inflammatory and vasodilating activities.  Upon oral administration, olinciguat targets, allosterically binds to and enhances the nitric oxide (NO)-dependent catalytic activity of sGC. This enhances NO-sGC signaling and increases the formation of the intracellular second messenger cyclic guanosine monophosphate (cGMP), which is derived from guanosine triphosphate (GTP). This enhances NO/cGMP-mediated muscle relaxation, suppresses leukocyte-endothelial interactions and promotes vascular anti-inflammatory effects. The NO/sGC/cGMP signaling pathway plays an important role in vasodilation, blood flow and inflammatory processes. sGC, a heme-containing cytoplasmic signaling enzyme, catalyzes the formation of cGMP from GTP in response to NO binding to heme.

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 an orally available, C-4 methyl carbonate analog of paclitaxel with potential antineoplastic activity. Like paclitaxel, BMS-275183 binds to tubulin and stabilizes microtubules, thereby inhibiting microtubule disassembly which results in cell-cycle arrest at the G2/M phase and an induction of apoptosis.

Output: COC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H](OC(C)=O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C[C@@](O)([C@@H](OC(=O)C4=CC=CC=C4)[C@H]21)C3(C)C


Input: The molecule is an enoate ester resulting from the formal condensation of the carboxy group of (2E)-4-{(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2E,4R,5S)-5-hydroxy-4-methylhex-2-en-1-yl]oxan-2-yl}-3-methylbut-2-enoic acid with the alcoholic hydroxy group of 8-hydroxyoctanoic acid. It is a monocarboxylic acid, an enoate ester, an enol, a member of oxanes, a secondary allylic alcohol and a homoallylic alcohol. It is a conjugate acid of a marinolate C.

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


Input: The molecule is trianion of N(6)-(UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl)-D-lysine; major species at pH 7.3. It is a nucleotide-sugar oxoanion and a dicarboxylic acid anion. It is a conjugate base of a N(6)-(UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-D-gamma-glutamyl)-D-lysine.


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

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


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

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


Input: The molecule is a lathyrane diterpenoid isolated from the roots of Euphorbia micractina. It is a lathyrane diterpenoid and an acetate ester.

Output: CC(=O)O[C@H]1[C@@H](C)C[C@]2(OC(C)=O)C(=O)/C(C)=C/[C@@H]3[C@H](CC/C(C)=C/[C@@H]12)C3(C)C


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

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


Input: The molecule is a lignan that consists of tetrahydrofuran-2-ol substituted by a 1,3-benzodioxol-5-ylmethyl group at positions 3 and a 3,4-dimethoxybenzyl group at position 4 (the 3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibts histamine release inhibitory activity. It has a role as a histamine antagonist and a plant metabolite. It is a member of benzodioxoles, a cyclic acetal, a lactol, a lignan and a secondary alcohol.

Output: COC1=CC=C(C[C@H]2COC(O)[C@@H]2CC2=CC=C3OCOC3=C2)C=C1OC


Input: The molecule is a doubly-charged alpha-amino-acid anion arising from deprotonation of the carboxy and phosphate groups of N-adenylyl-L-phenylalanine; major species at pH 7.3. It is an organophosphate oxoanion and an alpha-amino-acid anion. It is a conjugate base of a N-adenylyl-L-phenylalanine.

Output: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])N[C@@H](CC2=CC=CC=C2)C(=O)[O-])[C@@H](O)[C@H]1O


Input: The molecule is a phenylacetic acid derivative and non-steroidal anti-inflammatory drug (NSAID). NSAIDs inhibit cyclooxygenase (COX)-1 and-2 which are the enzyme responsible for producing prostaglandins (PGs). PGs contribute to inflammation and pain signalling. Diclofenac, like other NSAIDs, is often used as first line therapy for acute and chronic pain and inflammation from a variety of causes. Diclofenac was the product of rational drug design based on the structures of [phenylbutazone], [mefenamic acid], and [indomethacin]. The addition of two chlorine groups in the ortho position of the phenyl ring locks the ring in maximal torsion which appears to be related to increased potency. It is often used in combination with [misoprostol] to prevent NSAID-induced gastric ulcers. Diclofenac was first approved by the FDA in July 1988 under the trade name Voltaren, marketed by Novartis (previously Ciba-Geigy).

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


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 2-amino-5-oxocyclohex-1-enecarboxylic acid. It derives from a coenzyme A. It is a conjugate acid of a 2-amino-5-oxocyclohex-1-enecarbonyl-CoA(4-).

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)C1=C(N)CCC(=O)C1


Input: The molecule is an acyl-CoA(4-) that is the tetraanion of anthraniloyl-CoA arising from deprotonation of phosphate and diphosphate functions. It is a conjugate base of an anthraniloyl-CoA.

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)C1=CC=CC=C1N


Input: The molecule is a cholestanoid that is cholest-4-ene substituted by hydroxy groups at positions 20 and 25 and an oxo group at position 3. Isolated from Stachyurus himalaicus, it exhibits cytotoxic activity against human Hela cell lines. It has a role as a metabolite and an antineoplastic agent. It is a cholestanoid, a 20-hydroxy steroid, a 25-hydroxy steroid and a 3-oxo-Delta(4) steroid.

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


Input: The molecule is a disaccharide phosphate. It has a role as an Escherichia coli metabolite. It is functionally related to a sucrose. It is a conjugate acid of a sucrose 6(F)-phosphate(2-).

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


Input: The molecule is a depsipeptide isolated from Jaspis splendens. It has a role as an antineoplastic agent, an animal metabolite and a marine metabolite. It is a depsipeptide, a member of indoles, an organobromine compound, a member of catechols and a carboxylic ester.

Output: C/C(=C\[C@H](C)C[C@H](C)OC(=O)CC(=O)C1=CC=C(O)C(O)=C1)C[C@H](C)C(=O)N[C@@H](C)C(=O)N(C)[C@H](CC1=C(Br)NC2=CC=CC=C12)C(N)=O


Input: The molecule is a carotenoid ether that is spirilloxanthin substituted at position 2 by a hydroxy group. It is a carotenoid ether and a carotenol. It derives from a spirilloxanthin.

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)/C=C/C=C(C)/C=C/C(O)C(C)(C)OC


Input: The molecule is a member of the class of prostaglandins Falpha that is 15-oxo-prostaglandin F2alpha in which the methyl group has been oxidised to the corresponding carboxylic acid and in which the double bond at positions 13-14 has been reduced to a single bond. It has a role as a metabolite. It is a prostaglandins Falpha, an oxo dicarboxylic acid and a ketone. It is functionally related to a 15-oxoprostaglandin F2alpha.

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


Input: The molecule is a (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which both chiral centres have S configuration. It is an enantiomer of a (3R,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid.

Output: CC(C)N1C(/C=C/[C@@H](O)C[C@H](O)CC(=O)O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C21


Input: The molecule appears as a white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses.

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


Input: The molecule is a colorless crystalline solid with a medicinal odor. Melting point 45 °C. Sinks in water. Strong irritant to tissues; toxic by ingestion.

Output: OC1=CC=C(Cl)C=C1Cl


Input: The molecule is a chromium group element atom that has atomic number 24. It has a role as a micronutrient. It is a chromium group element atom and a metal allergen.

Output: [Cr]


Input: The molecule is conjugate base of N-acetyl-4-O-acetylneuraminic acid. It is a conjugate base of a N-acetyl-4-O-acetylneuraminic acid.

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


Input: The molecule is a 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one that has R configuration. It is an enantiomer of a (S)-flurtamone.

Output: CNC1=C(C2=CC=CC(C(F)(F)F)=C2)C(=O)[C@@H](C2=CC=CC=C2)O1


Input: The molecule is an imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish. It has a role as a carcinogenic agent and a mutagen. It is an imidazopyridine and a primary amino compound.

Output: CN1C(N)=NC2=NC=C(C3=CC=CC=C3)C=C21


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 is functionally related to 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 Serotonin and Norepinephrine Reuptake Inhibitor. The mechanism of action of it is as a Norepinephrine Uptake Inhibitor, and Serotonin Uptake Inhibitor.

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


Input: The molecule is an N-alkylpiperazine that is 1-(3-chlorophenyl)piperazine carrying a 3,3-diphenyl-2-hydroxyprop-1-yl group at position 4. A selective h5-HT1D antagonist, displaying 60-fold selectivity over h5-HT1B, and exhibiting little or no affinity for a range of other receptor types. It has a role as a serotonergic antagonist. It is a N-alkylpiperazine, a N-arylpiperazine, a secondary alcohol and a member of monochlorobenzenes. It is a conjugate base of a 4-(3-chlorophenyl)-1-(2-hydroxy-3,3-diphenylpropyl)piperazin-1-ium(1+).

Output: OC(CN1CCN(C2=CC=CC(Cl)=C2)CC1)C(C1=CC=CC=C1)C1=CC=CC=C1


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

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


Input: The molecule is a hydroperoxy fatty acid anion resulting from the deprotonation of the carboxy group of 10-hydroperoxy-8E-octadecenoic acid. The major species at pH 7.3. It is a hydroperoxy fatty acid anion and a hydroperoxyoctadecenoate. It is a conjugate base of a 10-hydroperoxy-8E-octadecenoic acid.

Output: CCCCCCCCC(/C=C/CCCCCCC(=O)[O-])OO


Input: The molecule is a C-glycosyl compound that is isovitexin substituted at positions 4 and 7 by beta-glucosyl 6-O-sinapoylglucosyl residues respectively It has a role as a metabolite. It is a C-glycosyl compound, a monohydroxyflavone, a cinnamate ester, a glycosyloxyflavone and a beta-D-glucoside. It derives from a trans-sinapic acid and an isovitexin.

Output: COC1=CC(/C=C/C(=O)OC[C@H]2OC(OC3=CC4=C(C(O)=C3[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)C=C(C3=CC=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C=C3)O4)[C@H](O)[C@@H](O)[C@@H]2O)=CC(OC)=C1O


Input: The molecule is an organic molecular entity. It is a conjugate base of a N-Acetyldemethylphosphinothricin.

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


Input: The molecule is a primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position. It has a role as a human metabolite. It is a primary alcohol and a pyrimidone. It derives from a uracil.

Output: O=C1NC=C(CO)C(=O)N1


Input: The molecule is a phosphonic acid consisting of 1-cyclopentyluracil having a phosphomethoxy group at position 2 on the cyclopentyl ring with (1R,2R)-trans-stereochemistry. It derives from a uracil and a phosphonic acid.

Output: O=C1C=CN([C@@H]2CCC[C@H]2OCP(=O)(O)O)C(=O)N1


Input: The molecule is the ammonium ion resulting from protonation of all three amino groups of bis(3-aminopropyl)amine; major species at pH 7.3. It is a conjugate acid of a bis(3-aminopropyl)amine.

Output: [NH3+]CCC[NH2+]CCC[NH3+]


Input: The molecule is a colorless odorless gas with an ether-like odor. It is shipped as a liquefied gas under its own vapor pressure. It is noncombustible. It can asphyxiate by the displacement of air. Contact with the liquid can cause frostbite. Exposure of the container to prolonged heat or fire may cause it to rupture violently and rocket.

Output: FC(F)(F)C(F)(F)Cl


Input: The molecule is a taxifolin that has (2S,3R)-configuration. It has a role as a metabolite. It is a conjugate acid of a (+)-epitaxifolin(1-). It is an enantiomer of a (-)-epitaxifolin.

Output: O=C1C2=C(O)C=C(O)C=C2O[C@@H](C2=CC=C(O)C(O)=C2)[C@H]1O