zerumboneoxide (CHEBI:66502)

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ChEBI Name	zerumboneoxide

ChEBI ID	CHEBI:66502

Definition	A sesquiterpenoid that is the 2, 3-epoxy derivative of zerumbone. Isolated from Zingiber zerumbet, it exhibits inhibitory activity against nitric oxide synthase.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C15H22O2

Net Charge

Average Mass

234.33400

Monoisotopic Mass

234.16198

InChI

InChI=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

InChIKey

UXYYOHOTPOQJPD-QNKGIFIZSA-N

SMILES

[H][C@]12CC(C)(C)\C=C\C(=O)\C(C)=C\CC[C@@]1(C)O2

Metabolite of Species	Details
Zingiber zerumbet (NCBI:txid311405)	Found in rhizome (BTO:0001181). See: PubMed

Roles Classification
Biological Role(s):	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	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

Registry Number	Type	Source
1620548	Reaxys Registry Number	Reaxys

Citation	Type	Source
15997145	PubMed citation	Europe PMC

Last Modified

12 July 2013