picrotoxinin (CHEBI:8206)

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ChEBI Name	picrotoxinin

ChEBI ID	CHEBI:8206

Definition	A picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone γ-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C15H16O6

Net Charge

Average Mass

292.285

Monoisotopic Mass

292.09469

InChI

InChI=1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8-,9-,10-,13-,14-,15+/m1/s1

InChIKey

PIMZUZSSNYHVCU-YKWPQBAZSA-N

SMILES

[C@]123[C@]4([C@@]([C@@H]5[C@H](C(C)=C)[C@H]([C@]4(OC1=O)[H])OC5=O)(O)C[C@]2(O3)[H])C

Roles Classification
Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. GABA antagonist A compound that inhibits the action of gamma-aminobutyric acid. serotonergic antagonist Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.

Application(s):	GABA antagonist A compound that inhibits the action of gamma-aminobutyric acid. serotonergic antagonist Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.

ChEBI Ontology
Outgoing	picrotoxinin (CHEBI:8206) has role GABA antagonist (CHEBI:65259) picrotoxinin (CHEBI:8206) has role plant metabolite (CHEBI:76924) picrotoxinin (CHEBI:8206) has role serotonergic antagonist (CHEBI:48279) picrotoxinin (CHEBI:8206) is a γ-lactone (CHEBI:37581) picrotoxinin (CHEBI:8206) is a epoxide (CHEBI:32955) picrotoxinin (CHEBI:8206) is a organic heteropentacyclic compound (CHEBI:38164) picrotoxinin (CHEBI:8206) is a picrotoxane sesquiterpenoid (CHEBI:134174) picrotoxinin (CHEBI:8206) is a tertiary alcohol (CHEBI:26878)

Incoming	picrotin (CHEBI:8205) has functional parent picrotoxinin (CHEBI:8206) picrotoxin (CHEBI:134126) has part picrotoxinin (CHEBI:8206)

IUPAC Name

(1R,3R,5S,8S,9R,12S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^9,12.0^3,5.0^5,13]tetradecane-6,11-dione

Last Modified

14 December 2016