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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:17 UTC
Update Date2022-03-07 02:52:24 UTC
HMDB IDHMDB0030026
Secondary Accession Numbers
  • HMDB30026
Metabolite Identification
Common NameIsohumulone A
DescriptionIsohumulone A, also known as photoisohumulone, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Based on a literature review a small amount of articles have been published on Isohumulone A.
Structure
Thumb
Synonyms
ValueSource
Isohumulone a2HMDB
PhotoisohumuloneHMDB
IsohumuloneHMDB
3,4-Dihydroxy-2-(3-methylbutanoyl)-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopenten-1-oneHMDB
Chemical FormulaC21H30O5
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
IUPAC Name3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
Traditional Nameisohumulone
CAS Registry Number467-72-1
SMILES
CC(C)CC(=O)C1=C(O)C(O)(C(CC=C(C)C)C1=O)C(=O)CC=C(C)C
InChI Identifier
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
InChI KeyQARXXMMQVDCYGZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMonocyclic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Vinylogous acid
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Enol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point62 - 63 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001322
KNApSAcK IDC00050939
Chemspider ID84039
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound93090
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.