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CHEBI:66335 - xanthohumol D

ChEBI IDCHEBI:66335
ChEBI Namexanthohumol D
Stars
DefinitionA member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and a 2-hydroxy-3-methylbut-3-en-1-yl group at position 3'. It has been isolated as a racemate from Humulus lupulus and has been shown to exhibit inhibitory activity against NO production.
Last Modified15 July 2013
DownloadsMolfile
FormulaC21H22O6
Net Charge0
Average Mass370.401
Monoisotopic Mass370.14164
SMILESC=C(C)C(O)Cc1c(O)cc(OC)c(C(=O)/C=C/c2ccc(O)cc2)c1O
InChIInChI=1S/C21H22O6/c1-12(2)17(24)10-15-18(25)11-19(27-3)20(21(15)26)16(23)9-6-13-4-7-14(22)8-5-13/h4-9,11,17,22,24-26H,1,10H2,2-3H3/b9-6+
InChIKeyIIWLGOCXDBSFCM-RMKNXTFCSA-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)
xanthohumol D (CHEBI:66335) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
xanthohumol D (CHEBI:66335) has role metabolite (CHEBI:25212)
xanthohumol D (CHEBI:66335) is a aromatic ether (CHEBI:35618)
xanthohumol D (CHEBI:66335) is a chalcones (CHEBI:23086)
xanthohumol D (CHEBI:66335) is a polyphenol (CHEBI:26195)
xanthohumol D (CHEBI:66335) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methylbut-3-en-1-yl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms  Source
rac-(2E)-1-{2,4-dihydroxy-3-[2-hydroxy-3-methyl-3-but-3-enyl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-oneChEBI
3'-(2-hydroxy-3-methylbutyl-3-enyl)-4,2',4'-trihydroxy-6'-methoxychalconeChEBI
Manual XrefsDatabases
552946ChemSpider
CPD-7129MetaCyc
LMPK12120295LIPID MAPS
HMDB0035003HMDB
Registry NumbersSources
Reaxys:8587407Reaxys
Citations