lupulone (CHEBI:6574)

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ChEBI Name	lupulone

ChEBI ID	CHEBI:6574

Definition	A β-bitter acid in which the acyl group is specified as 3-methylbutanoyl.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C26H38O4

Net Charge

Average Mass

414.579

Monoisotopic Mass

414.27701

InChI

InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28-29H,10,13-15H2,1-8H3

InChIKey

LSDULPZJLTZEFD-UHFFFAOYSA-N

SMILES

C=1(C(C(C(C(CC(C)C)=O)=C(C1CC=C(C)C)O)=O)(CC=C(C)C)CC=C(C)C)O

Metabolite of Species	Details
Humulus lupulus (NCBI:txid3486)	See: PubMed

Roles Classification
Biological Role(s):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. (via beta-bitter acid )

Application(s):	angiogenesis inhibitor An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	lupulone (CHEBI:6574) has role angiogenesis inhibitor (CHEBI:48422) lupulone (CHEBI:6574) has role antimicrobial agent (CHEBI:33281) lupulone (CHEBI:6574) has role antineoplastic agent (CHEBI:35610) lupulone (CHEBI:6574) has role apoptosis inducer (CHEBI:68495) lupulone (CHEBI:6574) is a β-bitter acid (CHEBI:136848) lupulone (CHEBI:6574) is conjugate acid of lupulone(1−) (CHEBI:134343)

Incoming	lupulone(1−) (CHEBI:134343) is conjugate base of lupulone (CHEBI:6574)

IUPAC Name

3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one

Last Modified

18 April 2017