CHEBI:73236 - (+)-cis-isohumulone

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ChEBI Name (+)-cis-isohumulone
ChEBI ID CHEBI:73236
ChEBI ASCII Name (+)-cis-isohumulone
Definition A cyclic ketone that is the naturally occurring (4S,5R) enantiomer of the cis-isomer of isohumolone, produced during the brewing process due to thermal isomerism, which converts humulones to isohumulones via an acyloin-type ring contraction.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
Supplier Information
Download Molfile XML SDF
Formula C21H30O5
Net Charge 0
Average Mass 362.45990
Monoisotopic Mass 362.20932
InChI InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3/t15-,21+/m0/s1
InChIKey QARXXMMQVDCYGZ-YCRPNKLZSA-N
SMILES CC(C)CC(=O)C1=C(O)[C@@](O)([C@@H](CC=C(C)C)C1=O)C(=O)CC=C(C)C
Metabolite of Species Details
Humulus lupulus (NCBI:txid3486) Found in cone (BTO:0000280). See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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ChEBI Ontology
Outgoing (+)-cis-isohumulone (CHEBI:73236) has role plant metabolite (CHEBI:76924)
(+)-cis-isohumulone (CHEBI:73236) is a cyclic ketone (CHEBI:3992)
(+)-cis-isohumulone (CHEBI:73236) is a enol (CHEBI:33823)
(+)-cis-isohumulone (CHEBI:73236) is a enone (CHEBI:51689)
(+)-cis-isohumulone (CHEBI:73236) is a tertiary α-hydroxy ketone (CHEBI:139592)
(+)-cis-isohumulone (CHEBI:73236) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(4S,5R)-3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-en-1-yl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
Note: (2013-07-12) For determination of absolute configuration as (4S,5R), see Urban, J., Dahlberg, C.J., Carroll, B.J. and Kaminsky, W. (2013) Absolute configuration of beer's bitter compounds. Angew. Chem. Int. Ed., v52, 1553-1555.
Synonym Source
cis-isohumulone ChEBI
Registry Numbers Types Sources
2062912 Reaxys Registry Number Reaxys
25522-96-7 CAS Registry Number SUBMITTER
Citations Waiting for Citations Types Sources
17624889 PubMed citation Europe PMC
IND20618913 Agricola citation Europe PMC
Last Modified
06 February 2018