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CHEBI:66331 - xanthohumol

Default Structure
ChEBI IDCHEBI:66331
ChEBI Namexanthohumol
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 prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.
Last Modified15 May 2024
DownloadsMolfile
FormulaC21H22O5
Net Charge0
Average Mass354.402
Monoisotopic Mass354.14672
SMILESCOc1cc(O)c(CC=C(C)C)c(O)c1C(=O)/C=C/c1ccc(O)cc1
InChIInChI=1S/C21H22O5/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/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+
InChIKeyORXQGKIUCDPEAJ-YRNVUSSQSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Humulus lupulus (ncbitaxon:3486)
- PubMed (15679315)
cone (BTO:0000280) PubMed (22111577) EtOH extract of hop cones
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.
anti-HIV-1 agent  An anti-HIV agent that destroys or inhibits the replication of HIV-1, the more infective and more virulent of the two types of HIV virus.
antiviral agent  A substance that destroys or inhibits replication of viruses.
EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor  An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of diacylglycerol O-acyltransferase (EC 2.3.1.20).
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
xanthohumol (CHEBI:66331) has role anti-HIV-1 agent (CHEBI:64947)
xanthohumol (CHEBI:66331) has role antineoplastic agent (CHEBI:35610)
xanthohumol (CHEBI:66331) has role antiviral agent (CHEBI:22587)
xanthohumol (CHEBI:66331) has role apoptosis inducer (CHEBI:68495)
xanthohumol (CHEBI:66331) has role EC 2.3.1.20 (diacylglycerol O-acyltransferase) inhibitor (CHEBI:64919)
xanthohumol (CHEBI:66331) has role metabolite (CHEBI:25212)
xanthohumol (CHEBI:66331) is a aromatic ether (CHEBI:35618)
xanthohumol (CHEBI:66331) is a chalcones (CHEBI:23086)
xanthohumol (CHEBI:66331) is a polyphenol (CHEBI:26195)
xanthohumol (CHEBI:66331) is conjugate acid of xanthohumol(1−) (CHEBI:134289)
Incoming Relation(s)
xanthohumol(1−) (CHEBI:134289) is conjugate base of xanthohumol (CHEBI:66331)
IUPAC Name 
(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonym  Source
2',4,4'-trihydroxy-6'-methoxy-3'-prenylchalconeChEBI
UniProt Name  Source
xanthohumolUniProt
Manual XrefsDatabases
C00007099KNApSAcK
C16417KEGG COMPOUND
CPD-7119MetaCyc
EP2579862Patent
HMDB0037479HMDB
LMPK12120294LIPID MAPS
WO2009126320Patent
XanthohumolWikipedia
Registry NumbersSources
Reaxys:2226282Reaxys
CAS:6754-58-1ChemIDplus
CAS:6754-58-1KEGG COMPOUND
Citations