5-hydroxyzerumbone (CHEBI:66050)

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ChEBI Name	5-hydroxyzerumbone

ChEBI ID	CHEBI:66050

Definition	A sesquiterpenoid that is zerumbone substituted by a hydroxy group at position 5. Isolated from the rhizomes Zingiber zerumbet, it has been found to inhibit lipopolysaccharide-induced nitric oxide production.

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

Supplier Information

Download	Molfile XML SDF

Formula

C15H22O2

Net Charge

Average Mass

234.33400

Monoisotopic Mass

234.16198

InChI

InChI=1S/C15H22O2/c1-11-5-7-15(3,4)8-6-14(17)12(2)10-13(16)9-11/h5-6,8,10,13,16H,7,9H2,1-4H3/b8-6+,11-5+,12-10+

InChIKey

NBVYFPSAUFQMAK-HNNGZUARSA-N

SMILES

C\C1=C/CC(C)(C)\C=C\C(=O)\C(C)=C\C(O)C1

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

Roles Classification
Biological Role(s):	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	5-hydroxyzerumbone (CHEBI:66050) has functional parent zerumbone (CHEBI:63892) 5-hydroxyzerumbone (CHEBI:66050) has parent hydride humulane (CHEBI:36523) 5-hydroxyzerumbone (CHEBI:66050) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) 5-hydroxyzerumbone (CHEBI:66050) has role metabolite (CHEBI:25212) 5-hydroxyzerumbone (CHEBI:66050) is a cyclic ketone (CHEBI:3992) 5-hydroxyzerumbone (CHEBI:66050) is a secondary alcohol (CHEBI:35681) 5-hydroxyzerumbone (CHEBI:66050) is a sesquiterpenoid (CHEBI:26658)

IUPAC Name

(2E,6E,10E)-4-hydroxy-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one

Synonym	Source
5-hydroxy-2E,6E,9E-humulatrien-8-one	ChEBI

Registry Number	Type	Source
10169836	Reaxys Registry Number	Reaxys

Last Modified

24 April 2013