xanthohumol (CHEBI:66331)

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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

Average Mass

354.39640

Monoisotopic Mass

354.14672

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:txid3486)	Found in cone (BTO:0000280). EtOH extract of hop cones See: PubMed
Humulus lupulus (NCBI:txid3486)	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.

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) xanthohumol (CHEBI:66331) is conjugate acid of xanthohumol(1−) (CHEBI:134289)

Incoming	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'-prenylchalcone	ChEBI

Last Modified

26 January 2017