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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:46:29 UTC
Update Date2019-07-23 06:19:26 UTC
HMDB IDHMDB0035753
Secondary Accession Numbers
  • HMDB35753
Metabolite Identification
Common Name(R)-(E)-4,7-Megastigmadien-9-one
Description(R)-(E)-4,7-Megastigmadien-9-one, also known as (R)-alpha-ionone or parmone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (R)-(E)-4,7-Megastigmadien-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862766
Synonyms
ValueSource
(+)-(6R)-alpha-IononeHMDB
(+)-alpha-IononeHMDB
(R)-(+)-alpha-IononeHMDB
(R)-alpha-IononeHMDB
(R-(e))-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-oneHMDB
3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (R)-(+)- (8ci)HMDB
4-[(1R)-2,6,6-Trimethyl-2-cyclohexen-1-yl]-(3E)-3-buten-2-oneHMDB
ParmoneHMDB
Chemical FormulaC13H20O
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
IUPAC Name(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
Traditional Name(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
CAS Registry Number24190-29-2
SMILES
CC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C
InChI Identifier
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+/t12-/m0/s1
InChI KeyUZFLPKAIBPNNCA-GUOLPTJISA-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

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP4.14ALOGPS
logP3.32ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.83ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.09 m³·mol⁻¹ChemAxon
Polarizability23.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9600000000-f52514927b7c7e5bd79aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9600000000-93c21f85616fb52a6763Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0076-6900000000-0d604eb8b56437636516Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9600000000-f52514927b7c7e5bd79aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9600000000-93c21f85616fb52a6763Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0076-6900000000-0d604eb8b56437636516Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fia-4900000000-9e9a8dc88676517f4055Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0900000000-0d1ee7a07c25e0eb379aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004u-3900000000-122599cd5a3606da3858Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9400000000-5525adff7c75947a3830Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-86ad4191ecec06d667ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-81ca79f706995e1f2313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aed-2900000000-e754146e5b21f942f91eSpectrum
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
FoodDB IDFDB014487
KNApSAcK IDNot Available
Chemspider ID4594306
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5498521
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.