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	ChemicalBook:CB21387988, ZINC000006090922

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