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CHEBI:66502 - zerumboneoxide

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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
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