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CHEBI:66050 - 5-hydroxyzerumbone

Default Structure
ChEBI IDCHEBI:66050
ChEBI Name5-hydroxyzerumbone
Stars
DefinitionA 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.
Last Modified24 April 2013
DownloadsMolfile
FormulaC15H22O2
Net Charge0
Average Mass234.339
Monoisotopic Mass234.16198
SMILESC/C1=C\CC(C)(C)/C=C/C(=O)/C(C)=C/C(O)C1
InChIInChI=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+
InChIKeyNBVYFPSAUFQMAK-HNNGZUARSA-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)
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-oneChEBI
Registry NumbersSources
Reaxys:10169836Reaxys
Citations