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CHEBI:66331 - xanthohumol

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ChEBI Name xanthohumol
ChEBI ID CHEBI:66331
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 prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H22O5
Net Charge 0
Average Mass 354.39640
Monoisotopic Mass 354.147
InChI InChI=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+
InChIKey ORXQGKIUCDPEAJ-YRNVUSSQSA-N
SMILES COc1cc(O)c(CC=C(C)C)c(O)c1C(=O)\C=C\c1ccc(O)cc1
Metabolite of Species Details
Humulus lupulus (NCBI:3486) Found in cone (BTO:0000280). EtOH extract of hop cones See: PubMed
Humulus lupulus (NCBI:3486) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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).
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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)
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'-prenylchalcone ChEBI
Database Links Databases
C00007099 KNApSAcK
C16417 KEGG COMPOUND
CPD-7119 MetaCyc
EP2579862 Patent
HMDB37479 HMDB
LMPK12120294 LIPID MAPS
WO2009126320 Patent
Xanthohumol Wikipedia
View more database links
Registry Numbers Types Sources
2226282 Reaxys Registry Number Reaxys
6754-58-1 CAS Registry Number KEGG COMPOUND
6754-58-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14670594 PubMed citation Europe PMC
15550272 PubMed citation Europe PMC
15679315 PubMed citation Europe PMC
15723722 PubMed citation Europe PMC
19634869 PubMed citation Europe PMC
22111577 PubMed citation Europe PMC
Last Modified
28 July 2014