dihydroxanthohumol (CHEBI:66332)

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ChEBI Name	dihydroxanthohumol

ChEBI ID	CHEBI:66332

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C21H24O5

Net Charge

Average Mass

356.41230

Monoisotopic Mass

356.16237

InChI

InChI=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

InChIKey

SVTCZHIDEDUTBH-UHFFFAOYSA-N

SMILES

COc1cc(O)c(CC=C(C)C)c(O)c1C(=O)CCc1ccc(O)cc1

Metabolite of Species	Details
Humulus lupulus (NCBI:txid3486)	See: PubMed

Roles Classification
Biological Role(s):	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	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	Sources
4,2',4'-trihydroxy-6'-methoxy-3'-prenyldihydrochalcone	ChEBI
α,β-dihydroxanthohumol	ChEBI

Registry Number	Type	Source
3446881	Reaxys Registry Number	Reaxys

Citation	Type	Source
15679315	PubMed citation	Europe PMC

Last Modified

15 July 2013