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CHEBI:66335 - xanthohumol D

Default Structure
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:
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)
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
3'-(2-hydroxy-3-methylbutyl-3-enyl)-4,2',4'-trihydroxy-6'-methoxychalconeChEBI
rac-(2E)-1-{2,4-dihydroxy-3-[2-hydroxy-3-methyl-3-but-3-enyl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-oneChEBI
Manual XrefsDatabases
552946ChemSpider
CPD-7129MetaCyc
HMDB0035003HMDB
LMPK12120295LIPID MAPS
Registry NumbersSources
Reaxys:8587407Reaxys
Citations