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CHEBI:66502 - zerumboneoxide

Default Structure
ChEBI IDCHEBI:66502
ChEBI Namezerumboneoxide
Stars
DefinitionA sesquiterpenoid that is the 2, 3-epoxy derivative of zerumbone. Isolated from Zingiber zerumbet, it exhibits inhibitory activity against nitric oxide synthase.
Last Modified12 July 2013
DownloadsMolfile
FormulaC15H22O2
Net Charge0
Average Mass234.339
Monoisotopic Mass234.16198
SMILES[H][C@]12CC(C)(C)/C=C/C(=O)/C(C)=C/CC[C@@]1(C)O2
InChIInChI=1S/C15H22O2/c1-11-6-5-8-15(4)13(17-15)10-14(2,3)9-7-12(11)16/h6-7,9,13H,5,8,10H2,1-4H3/b9-7+,11-6+/t13-,15+/m0/s1
InChIKeyUXYYOHOTPOQJPD-QNKGIFIZSA-N
Species of MetaboliteComponentSourceComments
Zingiber zerumbet (ncbitaxon:311405) rhizome (BTO:0001181) PubMed (15997145)
Roles Classification
Biological Roles:
EC 1.14.13.39 (nitric oxide synthase) inhibitor  An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
zerumboneoxide (CHEBI:66502) has functional parent zerumbone (CHEBI:63892)
zerumboneoxide (CHEBI:66502) has parent hydride α-humulene (CHEBI:49311)
zerumboneoxide (CHEBI:66502) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
zerumboneoxide (CHEBI:66502) has role metabolite (CHEBI:25212)
zerumboneoxide (CHEBI:66502) is a cyclic ketone (CHEBI:3992)
zerumboneoxide (CHEBI:66502) is a enone (CHEBI:51689)
zerumboneoxide (CHEBI:66502) is a epoxide (CHEBI:32955)
zerumboneoxide (CHEBI:66502) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
(1R,4E,7E,11S)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one
Synonyms  Source
(2R,3R)-epoxy-6E,9E-humulatrien-8-oneChEBI
zerumbone epoxideChEBI
Registry NumbersSources
Reaxys:1620548Reaxys
Citations