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CHEBI:66336 - xenovulene A

ChEBI IDCHEBI:66336
ChEBI Namexenovulene A
Stars
DefinitionA sesquiterpenoid based on a humulene skeleton. It is isolated from Sarocladium strictum and has been shown to exhibit inhibitory activity against GABA receptor.
Last Modified15 July 2013
DownloadsMolfile
FormulaC22H30O4
Net Charge0
Average Mass358.478
Monoisotopic Mass358.21441
SMILES[H][C@@]12CC/C(C)=C/CC(C)(C)/C=C/C[C@@]1(C)OC1=C(O)C(=O)[C@@]3([H])CO[C@]2([H])[C@@]13[H]
InChIInChI=1S/C22H30O4/c1-13-6-7-15-19-16-14(12-25-19)17(23)18(24)20(16)26-22(15,4)10-5-9-21(2,3)11-8-13/h5,8-9,14-16,19,24H,6-7,10-12H2,1-4H3/b9-5+,13-8+/t14-,15-,16-,19-,22+/m0/s1
InChIKeyWDFUVZRTUNQXHC-KVPIFFDFSA-N
Species of MetaboliteComponentSourceComments
Sarocladium strictum (ncbitaxon:5046) - PubMed (7649852)
Roles Classification
Biological Roles:
GABA antagonist  A compound that inhibits the action of γ-aminobutyric acid.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
GABA antagonist  A compound that inhibits the action of γ-aminobutyric acid.
ChEBI Ontology
Outgoing Relation(s)
xenovulene A (CHEBI:66336) has role GABA antagonist (CHEBI:65259)
xenovulene A (CHEBI:66336) has role metabolite (CHEBI:25212)
xenovulene A (CHEBI:66336) is a cyclic ether (CHEBI:37407)
xenovulene A (CHEBI:66336) is a enone (CHEBI:51689)
xenovulene A (CHEBI:66336) is a organic heterotetracyclic compound (CHEBI:38163)
xenovulene A (CHEBI:66336) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
(2aR,5aR,11E,14aS,14bS,14cS)-4-hydroxy-5a,9,9,12-tetramethyl-2a,5a,6,9,10,13,14,14a,14b,14c-decahydro-1,5-dioxacyclopenta[cd]cycloundeca[f]inden-3(2)-one
Registry NumbersSources
Reaxys:7310576Reaxys
Citations