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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:10 UTC
Update Date2020-02-26 21:44:14 UTC
HMDB IDHMDB0029704
Secondary Accession Numbers
  • HMDB29704
Metabolite Identification
Common Name1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one
Description1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one, also known as allyl alpha-ionone or cetone V, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753454
Synonyms
ValueSource
Allyl alpha-iononeHMDB
Allyl iononeHMDB
Allyl-a-iononeHMDB
Cetone VHMDB
FEMA 2033HMDB
HexalonHMDB
PolyoneHMDB
Chemical FormulaC16H24O
Average Molecular Weight232.3612
Monoisotopic Molecular Weight232.18271539
IUPAC Name(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)hepta-1,6-dien-3-one
Traditional Name(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)hepta-1,6-dien-3-one
CAS Registry Number79-78-7
SMILES
CC1=CCCC(C)(C)C1\C=C\C(=O)CCC=C
InChI Identifier
InChI=1S/C16H24O/c1-5-6-9-14(17)10-11-15-13(2)8-7-12-16(15,3)4/h5,8,10-11,15H,1,6-7,9,12H2,2-4H3/b11-10+
InChI KeyFXCYGAGBPZQRJE-ZHACJKMWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cyclofarsesane sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Sesquiterpenoid
  • Ionone derivative
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0046 g/LALOGPS
logP4.79ALOGPS
logP4.6ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.96 m³·mol⁻¹ChemAxon
Polarizability28.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05p6-5940000000-beba5be45477f5c3ad42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1390000000-ea4eff05669679da083aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05q3-5920000000-d87dbb8ca107ff9e9bdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvl-9410000000-5c6850c33ae570944880Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0190000000-20c3289c174a5d0de509Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5890000000-15fe54067e90dcd90f37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00a6-4900000000-d80e4de9b081588ebb05Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB000898
KNApSAcK IDNot Available
Chemspider ID4517909
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5365976
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.