EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66332 - dihydroxanthohumol

Default Structure
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:
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)
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
4,2',4'-trihydroxy-6'-methoxy-3'-prenyldihydrochalconeChEBI
α,β-dihydroxanthohumolChEBI
Manual XrefsDatabases
HMDB0035440HMDB
LMPK12120536LIPID MAPS
Registry NumbersSources
Reaxys:3446881Reaxys
Citations