CHEBI:66335 - xanthohumol D

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ChEBI Name xanthohumol D
ChEBI ID CHEBI:66335
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C21H22O6
Net Charge 0
Average Mass 370.39580
Monoisotopic Mass 370.14164
InChI InChI=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+
InChIKey IIWLGOCXDBSFCM-RMKNXTFCSA-N
SMILES COc1cc(O)c(CC(O)C(C)=C)c(O)c1C(=O)\C=C\c1ccc(O)cc1
Metabolite of Species Details
Humulus lupulus (NCBI:txid3486) See: PubMed
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
3'-(2-hydroxy-3-methylbutyl-3-enyl)-4,2',4'-trihydroxy-6'-methoxychalcone ChEBI
rac-(2E)-1-{2,4-dihydroxy-3-[2-hydroxy-3-methyl-3-but-3-enyl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)-2-propen-1-one ChEBI
Manual Xrefs Databases
552946 ChemSpider
CPD-7129 MetaCyc
HMDB0035003 HMDB
LMPK12120295 LIPID MAPS
View more database links
Registry Number Type Source
8587407 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15679315 PubMed citation Europe PMC
Last Modified
15 July 2013