humulone (CHEBI:5769)

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ChEBI Name	humulone

ChEBI ID	CHEBI:5769

Definition	An optically active cyclic ketone consisting of 3,5,6-trihydroxycyclohexa-2,4-dien-1-one bearing two 3-methylbut-2-en-1-yl substituents at positions 4 and 6 as well as a 3-methylbutanoyl group at the 2-position.

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

Supplier Information

Download	Molfile XML SDF

Formula

C21H30O5

Net Charge

Average Mass

362.45990

Monoisotopic Mass

362.20932

InChI

InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m1/s1

InChIKey

VMSLCPKYRPDHLN-OAQYLSRUSA-N

SMILES

CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@](O)(CC=C(C)C)C1=O

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

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	antibacterial drug A drug used to treat or prevent bacterial infections. cyclooxygenase 2 inhibitor A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

Application(s):	antibacterial drug A drug used to treat or prevent bacterial infections.

ChEBI Ontology
Outgoing	humulone (CHEBI:5769) has role antibacterial drug (CHEBI:36047) humulone (CHEBI:5769) has role antioxidant (CHEBI:22586) humulone (CHEBI:5769) has role cyclooxygenase 2 inhibitor (CHEBI:50629) humulone (CHEBI:5769) has role metabolite (CHEBI:25212) humulone (CHEBI:5769) is a aromatic ketone (CHEBI:76224) humulone (CHEBI:5769) is a cyclic ketone (CHEBI:3992) humulone (CHEBI:5769) is a diketone (CHEBI:46640) humulone (CHEBI:5769) is a tertiary α-hydroxy ketone (CHEBI:139592) humulone (CHEBI:5769) is a triol (CHEBI:27136)

IUPAC Name

(6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one

Synonyms	Sources
(6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone	ChemIDplus
α-humulon	ChemIDplus
humulon	ChemIDplus
Humulone	KEGG COMPOUND

Last Modified

07 February 2018

General Comment
2011-07-26	An antibacterial compound isolated from the hop plant, Humulus lupulus.