Input: The molecule is an L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy to the amino group of anticapsin; major species at pH 7.3. It has a role as an EC 2.6.1.16 (glutamine--fructose-6-phosphate transaminase (isomerizing)) inhibitor, an antimicrobial agent, a bacterial metabolite and an antimetabolite. It is a tautomer of an anticapsin.

Output: [NH3+][C@@H](C[C@@H]1CCC(=O)[C@@H]2O[C@H]12)C(=O)[O-]


Input: The molecule is conjugate base of (R)-piperazine-2-carboxylic acid. It is a conjugate base of a (R)-piperazine-2-carboxylic acid and a (R)-piperazine-2-carboxylic acid zwitterion. It is an enantiomer of a (S)-piperazine-2-carboxylate.

Output: O=C([O-])[C@H]1CNCCN1


Input: The molecule is an anthocyanidin cation that is flavylium bearing five hydroxy substituents at positions 3, 3', 4', 5 and 7 as well as a methoxy substituent at position 5'. It has a role as a plant metabolite. It is a conjugate acid of a petunidin(1-).

Output: COC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O)=CC(O)=C1O


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 is functionally related to a cytosine.

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


Input: The molecule is an arsenic oxoanion. It is a conjugate base of an arsonous acid. It is a conjugate acid of an arsonite(2-).

Output: [O-][AsH]O


Input: The molecule is an orally available potassium channel blocker that increases acetylcholine in synaptic clefts of peripheral nerve endings and is used to treat the Lambert-Eaton myasthenic syndrome. Amifampridine is associated with a low rate of transient serum enzyme elevations during therapy but has not been linked with instances of clinically apparent acute liver injury.

Output: NC1=CC=NC=C1N


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

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


Input: The molecule is the meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase. It has a role as an antineoplastic agent, a lipoxygenase inhibitor, a hypoglycemic agent and a metabolite.

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 a member of the class of cyclohexenones that is (1R,5S,6R)-4-amino-5-hydroxy-1-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one in which one of the amino hydrogens is replaced by an acetyl group. It has a role as a bacterial metabolite. It is an acetamide, an epoxide, a member of cyclohexenones, an enone, an oxabicycloalkane, a primary alcohol and a tertiary alcohol.

Output: CC(=O)NC1=CC(=O)[C@]2(CO)O[C@@H]2[C@H]1O


Input: The molecule is 1-acyl-2-arachidonoyl-sn-glycero-3-phospho-D-myo-inositol in which the 1-acyl group is specified as oleoyl. It has a role as a human metabolite. It is functionally related to an oleic acid and an arachidonic acid. It is a conjugate acid of a 1-oleoyl-2-arachidonoyl-sn-glycero-3-phospho-1D-myo-inositol(1-).

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


Input: The molecule is an N-acylglycine in which the acyl group is specified as benzoyl. It has a role as a uremic toxin and a human blood serum metabolite. It is a conjugate acid of a N-benzoylglycinate.

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


Input: The molecule is a dipeptide composed of glutamic acid and threonine joined by a peptide linkage. It has a role as a human metabolite. It is functionally related to a glutamic acid and a threonine.

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


Input: The molecule is the formate ester of isoamylol. It is functionally related to an isoamylol.

Output: CC(C)CCOC=O


Input: The molecule is the ammonium ion resulting from deprotonation 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 highly selective phosphodiesterase-4 (PDE4) inhibitor first approved in the EU in April 2010 for the management of chronic obstructive pulmonary disease. PDE4 is a major cyclic-3',5′-adenosinemonophosphate (cyclic AMP, cAMP)-metabolizing enzyme expressed on nearly all immune and pro-inflammatory cells, in addition to structural cells like those of the smooth muscle or epithelium. The resultant increase in intracellular cAMP induced by roflumilast's inhibition of PDE4 is thought to mediate its disease-modifying effects, although its precise mechanism of action has yet to be elucidated.

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


Input: The molecule is a phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid. It has a role as an apoptosis inhibitor, an androstane receptor agonist and a plasticiser. It is a phthalate ester and a diester.

Output: CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC


Input: The molecule is an organophosphate oxoanion resulting from the deprotonation of all four phosphate OH groups from D-ribose 5-triphosphate; major species at pH 7.3. It is a conjugate base of a D-ribose 5-triphosphate.

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


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

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


Input: The molecule is 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 derives from 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 monocarboxylic acid anion that is the is conjugate base of 4-O-beta-D-glucosyl-4-coumaric acid. It derives from a 4-coumarate. It is a conjugate base of a 4-O-beta-D-glucosyl-4-coumaric acid.

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


Input: The molecule is a docosanoid that is (7Z,10Z,12E,16Z,19Z)-docosapentaenoic acid carrying a hydroperoxy substituent at position 14. It is a docosanoid, a hydroperoxy fatty acid and a long-chain fatty acid. It derives from a (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid. It is a conjugate acid of a (7Z,10Z,12E,16Z,19Z)-14-hydroperoxydocosapentaenoate.

Output: CC/C=C\C/C=C\CC(/C=C/C=C\C/C=C\CCCCCC(=O)O)OO


Input: The molecule is a carbobicyclic compound and sesquiterpene that is 1,2,3,4,5,6,7,8-octahydroazulene which is substituted by methyl groups at positions 1 and 4 and by a (prop-1-en-2-yl group at position 7 (the 1S,4S,7R enantiomer). It has a role as a volatile oil component and a plant metabolite. It is a carbobicyclic compound and a sesquiterpene.

Output: C=C(C)[C@@H]1CC[C@H](C)C2=C(C1)[C@@H](C)CC2


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

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


Input: The molecule is an adrenergic agonist with vasoconstrictive activity. Etilefrine selectively binds to and activates alpha-1-adrenergic receptors of the arteriolar and venous vasculature. This causes smooth muscle contraction and leads to a decrease in venous pooling and increase in blood pressure. This agent may also stimulate beta-1 adrenergic receptors, leading to positive chronotropic and inotropic effects.

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


Input: The molecule is an epoxy(hydroxy)icosatrienoate that is the conjugate base of 5,6-epoxy-20-hydroxy-(8Z,11Z,14Z)-eicosatrienoic acid arising from deprotonation of the carboxylic acid function; major species at pH 7.3. It is an icosanoid anion, a polyunsaturated fatty acid anion, an epoxy fatty acid anion and an omega-hydroxy-long-chain fatty acid anion. It is functionally related to a 5,6-EET(1-). It is a conjugate base of a 5,6-epoxy-20-hydroxy-(8Z,11Z,14Z)-icosatrienoic acid.

Output: O=C([O-])CCCC1OC1C/C=C\C/C=C\C/C=C\CCCCCO


Input: The molecule is a norepinephrine reuptake inhibitor of the tetracyclic antidepressant family that is related to maprotiline. This drug was never marketed. Oxaprotiline is a racemic mixture of the isomers levoprotiline and dextroprotiline. Levoprotiline is the R or levo isomer of oxaprotiline (CGP-12,103-A). Dextroprotiline is the S or dextro isomer of oxaprotiline (CGP-12,104-A). Both enantiomers have antidepressant effects but levoprotiline also is an antihistamine and dextroprotiline has many other pharmacological actions.

Output: CNCC(O)CC12CCC(C3=CC=CC=C31)C1=CC=CC=C12


Input: The molecule is a pyridine alkaloid that is 2,2'-bipyridine substituted by a hydroxy group at position 4 and an (acetylamino)methyl group at position 6. Isolated from the marine-derived actinomycete Actinoalloteichus cyanogriseus, it exhibits antineoplastic activity. It has a role as an antineoplastic agent, a bacterial metabolite and a marine metabolite. It is a member of bipyridines, a monohydroxypyridine, a pyridine alkaloid and a member of acetamides. It derives from a hydride of a 2,2'-bipyridine.

Output: CC(=O)NCC1=CC(=O)C=C(C2=CC=CC=N2)N1


Input: The molecule is the conjugate base of methoxymycolic acid type-3 (IX). A class of mycolic acids characterized by the presence of a proximal cis C=C double bond and a distal (CH-CH3)-(CHO-CH3) fragment of (S,S) stereochemistry in the meromycolic chain.

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