EMBL-EBI | Chemical Biology | ChEBI

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

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:
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
antiviral agent  A substance that destroys or inhibits replication of viruses.
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