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CHEBI:66332 - dihydroxanthohumol

ChEBI IDCHEBI:66332
ChEBI Namedihydroxanthohumol
Stars
DefinitionA member of the class of dihydrochalcones that is the α,β-dihydro derivative of xanthohumol. Isolated from Humulus lupulus, it exhibits inhibition of NO production.
Last Modified15 July 2013
DownloadsMolfile
FormulaC21H24O5
Net Charge0
Average Mass356.418
Monoisotopic Mass356.16237
SMILESCOc1cc(O)c(CC=C(C)C)c(O)c1C(=O)CCc1ccc(O)cc1
InChIInChI=1S/C21H24O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-6,8-9,12,22,24-25H,7,10-11H2,1-3H3
InChIKeySVTCZHIDEDUTBH-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Humulus lupulus (ncbitaxon:3486) - PubMed (15679315)
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)
dihydroxanthohumol (CHEBI:66332) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
dihydroxanthohumol (CHEBI:66332) has role metabolite (CHEBI:25212)
dihydroxanthohumol (CHEBI:66332) is a aromatic ether (CHEBI:35618)
dihydroxanthohumol (CHEBI:66332) is a dihydrochalcones (CHEBI:71230)
dihydroxanthohumol (CHEBI:66332) is a polyphenol (CHEBI:26195)
IUPAC Name 
1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
Synonyms  Source
α,β-dihydroxanthohumolChEBI
4,2',4'-trihydroxy-6'-methoxy-3'-prenyldihydrochalconeChEBI
Manual XrefsDatabases
LMPK12120536LIPID MAPS
HMDB0035440HMDB
Registry NumbersSources
Reaxys:3446881Reaxys
Citations