CHEBI:66333 - oxygenated xanthohumol

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ChEBI Name oxygenated xanthohumol
ChEBI ID CHEBI:66333
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-methoxy-3-methylbutyl 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 C22H26O7
Net Charge 0
Average Mass 402.43760
Monoisotopic Mass 402.16785
InChI InChI=1S/C22H26O7/c1-22(2,29-4)19(26)11-15-17(25)12-18(28-3)20(21(15)27)16(24)10-7-13-5-8-14(23)9-6-13/h5-10,12,19,23,25-27H,11H2,1-4H3/b10-7+
InChIKey YXGBQKBRCDLZMP-JXMROGBWSA-N
SMILES COc1cc(O)c(CC(O)C(C)(C)OC)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 oxygenated xanthohumol (CHEBI:66333) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
oxygenated xanthohumol (CHEBI:66333) has role metabolite (CHEBI:25212)
oxygenated xanthohumol (CHEBI:66333) is a aromatic ether (CHEBI:35618)
oxygenated xanthohumol (CHEBI:66333) is a chalcones (CHEBI:23086)
oxygenated xanthohumol (CHEBI:66333) is a polyphenol (CHEBI:26195)
oxygenated xanthohumol (CHEBI:66333) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(2E)-1-[2,4-dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonym Source
rac-1-[2,4-dihydroxy-3-(2-hydroxy-3-methoxy-3-methylbutyl)-6-methoxyphenyl]-3-(4-hydroxyphenyl)propenone ChEBI
Registry Number Type Source
10206441 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15679315 PubMed citation Europe PMC
Last Modified
06 February 2018