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CHEBI:8206 - picrotoxinin

Default Structure
ChEBI IDCHEBI:8206
ChEBI Namepicrotoxinin
Stars
DefinitionA 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.
Last Modified14 December 2016
DownloadsMolfile
FormulaC15H16O6
Net Charge0
Average Mass292.287
Monoisotopic Mass292.09469
SMILES[H][C@@]12C[C@@]3(O)[C@H]4C(=O)O[C@H]([C@H]4C(=C)C)[C@@]4([H])OC(=O)[C@]1(O2)[C@@]34C
InChIInChI=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
InChIKeyPIMZUZSSNYHVCU-YKWPQBAZSA-N
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
serotonergic antagonist  Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
GABA antagonist  A compound that inhibits the action of γ-aminobutyric acid.
Applications:
serotonergic antagonist  Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
GABA antagonist  A compound that inhibits the action of γ-aminobutyric acid.
ChEBI Ontology
Outgoing Relation(s)
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 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)
picrotoxinin (CHEBI:8206) is a γ-lactone (CHEBI:37581)
Incoming Relation(s)
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[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione
Synonyms  Source
(−)-picrotoxininLIPID MAPS
picrotoxinineChemIDplus
Manual XrefsDatabases
C00003350KNApSAcK
C09529KEGG COMPOUND
LMPR0103540001LIPID MAPS
RI5PDBeChem
Registry NumbersSources
Reaxys:42745Reaxys
CAS:17617-45-7KEGG COMPOUND
Citations