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CHEBI:73236 - (+)-cis-isohumulone

ChEBI IDCHEBI:73236
ChEBI Name(+)-cis-isohumulone
Stars
ASCII Name(+)-cis-isohumulone
DefinitionA 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.
Last Modified6 February 2018
Submittersjupe
DownloadsMolfile
FormulaC21H30O5
Net Charge0
Average Mass362.466
Monoisotopic Mass362.20932
SMILESCC(C)=CCC(=O)[C@@]1(O)C(O)=C(C(=O)CC(C)C)C(=O)[C@@H]1CC=C(C)C
InChIInChI=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
InChIKeyQARXXMMQVDCYGZ-YCRPNKLZSA-N
Species of MetaboliteComponentSourceComments
Humulus lupulus (ncbitaxon:3486) cone (BTO:0000280) PubMed (17624889)
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
(+)-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 alcohol (CHEBI:26878)
(+)-cis-isohumulone (CHEBI:73236) is a tertiary α-hydroxy ketone (CHEBI:139592)
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
Synonym  Source
cis-isohumuloneChEBI
Registry NumbersSources
Reaxys:2062912Reaxys
CAS:25522-96-7SUBMITTER
Citations