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CHEBI:66333 - oxygenated xanthohumol

ChEBI IDCHEBI:66333
ChEBI Nameoxygenated xanthohumol
Stars
DefinitionA 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.
Last Modified6 February 2018
DownloadsMolfile
FormulaC22H26O7
Net Charge0
Average Mass402.443
Monoisotopic Mass402.16785
SMILESCOc1cc(O)c(CC(O)C(C)(C)OC)c(O)c1C(=O)/C=C/c1ccc(O)cc1
InChIInChI=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+
InChIKeyYXGBQKBRCDLZMP-JXMROGBWSA-N
Species of MetaboliteComponentSourceComments
Humulus lupulus (ncbitaxon:3486) - PubMed (15679315)
Roles Classification
Biological Roles:
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 Relation(s)
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)propenoneChEBI
Registry NumbersSources
Reaxys:10206441Reaxys
Citations