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CHEBI:5769 - humulone

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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial drug  A drug used to treat or prevent bacterial infections.
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
HumuloneKEGG COMPOUND
(6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienoneChemIDplus
α-humulonChemIDplus
humulonChemIDplus
Manual XrefsDatabases
C10695KEGG COMPOUND
US2011021610Patent
WO2009114939Patent
DE102007028397Patent
CN101134719Patent
C00002697KNApSAcK
Registry NumbersSources
Reaxys:3221160Reaxys
CAS:23510-81-8KEGG COMPOUND
CAS:26472-41-3ChemIDplus
Citations