EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66333 - oxygenated xanthohumol

Default Structure
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:
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 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