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CHEBI:66050 - 5-hydroxyzerumbone

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:
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)
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