EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:8206 - picrotoxinin

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:
serotonergic antagonist  Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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 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
C09529KEGG COMPOUND
C00003350KNApSAcK
RI5PDBeChem
LMPR0103540001LIPID MAPS
Registry NumbersSources
Reaxys:42745Reaxys
CAS:17617-45-7KEGG COMPOUND
Citations