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CHEBI:5769 - humulone

Default Structure
ChEBI IDCHEBI:5769
ChEBI Namehumulone
Stars
DefinitionAn 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.
Last Modified7 February 2018
DownloadsMolfile
FormulaC21H30O5
Net Charge0
Average Mass362.466
Monoisotopic Mass362.20932
SMILESCC(C)=CCC1=C(O)[C@](O)(CC=C(C)C)C(=O)C(C(=O)CC(C)C)=C1O
InChIInChI=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
InChIKeyVMSLCPKYRPDHLN-OAQYLSRUSA-N
Species of MetaboliteComponentSourceComments
Humulus lupulus (ncbitaxon:3486) cone (BTO:0000280) PubMed (22111577) EtOH extract of hop cones
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
antibacterial drug  A drug used to treat or prevent bacterial infections.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
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  Source
(6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienoneChemIDplus
humulonChemIDplus
HumuloneKEGG COMPOUND
α-humulonChemIDplus
Manual XrefsDatabases
C00002697KNApSAcK
C10695KEGG COMPOUND
CN101134719Patent
DE102007028397Patent
US2011021610Patent
WO2009114939Patent
Registry NumbersSources
Reaxys:3221160Reaxys
CAS:23510-81-8KEGG COMPOUND
CAS:26472-41-3ChemIDplus
Citations