xanthohumol B (CHEBI:66334)

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ChEBI Name	xanthohumol B

ChEBI ID	CHEBI:66334

Definition	A member of the class of chalcones that is (2E)-1-(3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one substituted by hydroxy groups at position 3 and 5, a methoxy group at position 7 and geminal methyl groups at position 2. It has been isolated as a racemate from Humulus lupulus and has been shown to exhibit inhibitory activity against nitric oxide production.

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

Supplier Information

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Formula

C21H22O6

Net Charge

Average Mass

370.39580

Monoisotopic Mass

370.14164

InChI

InChI=1S/C21H22O6/c1-21(2)18(24)10-14-16(27-21)11-17(26-3)19(20(14)25)15(23)9-6-12-4-7-13(22)8-5-12/h4-9,11,18,22,24-25H,10H2,1-3H3/b9-6+

InChIKey

GUQGMEWOCKDLDE-RMKNXTFCSA-N

SMILES

COc1cc2OC(C)(C)C(O)Cc2c(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.

ChEBI Ontology
Outgoing	xanthohumol B (CHEBI:66334) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908) xanthohumol B (CHEBI:66334) has role metabolite (CHEBI:25212) xanthohumol B (CHEBI:66334) is a aromatic ether (CHEBI:35618) xanthohumol B (CHEBI:66334) is a chalcones (CHEBI:23086) xanthohumol B (CHEBI:66334) is a polyphenol (CHEBI:26195)

IUPAC Name

(2E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Synonyms	Sources
Dehydrocycloxanthohumol hydrate	LIPID MAPS
rac-(E)-1-(3,5-dihydroxy-7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one	ChEBI
rac-6'',6''-dimethyl-5''-hydroxy-4'',5''-dihydropyrano[2'',3'':4',3']-4,2'-dihydroxy-6'-methoxychalcone	ChEBI
rac-6-[3,4-dihydro-3,5-dihydroxy-7-methoxy-2,2-dimethyl-2H-benzo[b]pyrano]-3-(4-hydroxyphenyl)-2-propen-1-one	ChEBI

Registry Number	Type	Source
7828262	Reaxys Registry Number	Reaxys

Last Modified

15 July 2013