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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:54:49 UTC
Update Date2023-02-21 17:24:31 UTC
HMDB IDHMDB0034979
Secondary Accession Numbers
  • HMDB34979
Metabolite Identification
Common Namegamma-Ionone
Descriptiongamma-Ionone, also known as g-ionon, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on gamma-Ionone.
Structure
Data?1677000271
Synonyms
ValueSource
(3E)-4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-oneChEBI
gamma-IononChEBI
g-IononGenerator
Γ-iononGenerator
g-IononeGenerator
Γ-iononeGenerator
(3E)-4-(2,2-Dimethyl-6-methylidenecyclohexyl)but-3-en-2-oneHMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-oneHMDB
4-(2,2-Dimethyl-6-methylenecyclohexyl)-3-buten-2-one, 9ciHMDB
4-(2-Methylene-6,6-dimethylcyclohexyl)-3-buten-2-oneHMDB
FEMA 3175HMDB
gamma-LononeHMDB
laquo gammaraquo -IononeHMDB
Chemical FormulaC13H20O
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
IUPAC Name(3E)-4-(2,2-dimethyl-6-methylidenecyclohexyl)but-3-en-2-one
Traditional Nameionone
CAS Registry Number79-76-5
SMILES
CC(=O)\C=C\C1C(=C)CCCC1(C)C
InChI Identifier
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8,12H,1,5-6,9H2,2-4H3/b8-7+
InChI KeySFEOKXHPFMOVRM-BQYQJAHWSA-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 Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point267.00 to 268.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility8.83 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.505 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0096 g/LALOGPS
logP3.99ALOGPS
logP3.38ChemAxon
logS-4.3ALOGPS
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
Refractivity61.02 m³·mol⁻¹ChemAxon
Polarizability23.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+150.90730932474
DeepCCS[M-H]-148.54430932474
DeepCCS[M-2H]-182.7230932474
DeepCCS[M+Na]+157.43430932474
AllCCS[M+H]+144.232859911
AllCCS[M+H-H2O]+140.132859911
AllCCS[M+NH4]+147.932859911
AllCCS[M+Na]+149.032859911
AllCCS[M-H]-150.132859911
AllCCS[M+Na-2H]-151.132859911
AllCCS[M+HCOO]-152.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
gamma-IononeCC(=O)\C=C\C1C(=C)CCCC1(C)C1883.7Standard polar33892256
gamma-IononeCC(=O)\C=C\C1C(=C)CCCC1(C)C1410.1Standard non polar33892256
gamma-IononeCC(=O)\C=C\C1C(=C)CCCC1(C)C1409.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
gamma-Ionone,1TMS,isomer #1C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C1590.7Semi standard non polar33892256
gamma-Ionone,1TMS,isomer #1C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C1612.3Standard non polar33892256
gamma-Ionone,1TBDMS,isomer #1C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C1838.0Semi standard non polar33892256
gamma-Ionone,1TBDMS,isomer #1C=C(/C=C/C1C(=C)CCCC1(C)C)O[Si](C)(C)C(C)(C)C1847.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Ionone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ba-4900000000-f9aafc2b2b7c434052c52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Ionone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Ionone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 10V, Positive-QTOFsplash10-002f-0900000000-222c25bb3e7a42ab13212016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 20V, Positive-QTOFsplash10-004u-3900000000-e1117004acdbca234f892016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 40V, Positive-QTOFsplash10-014i-9400000000-3afe7c89edcfe4b080b12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 10V, Negative-QTOFsplash10-0006-0900000000-099fc3506ab6ef6a84d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 20V, Negative-QTOFsplash10-0006-0900000000-2c62147e95b324ad1bbb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 40V, Negative-QTOFsplash10-05ed-2900000000-43f9c40d0da2463f54e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 10V, Positive-QTOFsplash10-006x-0900000000-f7be24804814148e43a52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 20V, Positive-QTOFsplash10-05fu-8900000000-719975180f85f30cd26c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 40V, Positive-QTOFsplash10-052f-9500000000-b246cc8c2e31e4ef83712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 10V, Negative-QTOFsplash10-0006-0900000000-14436e4d9ff8d032db542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 20V, Negative-QTOFsplash10-00di-0900000000-8ba0b873872011e97fa42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Ionone 40V, Negative-QTOFsplash10-00dj-3900000000-01234d354968b8246a212021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDFDB013578
KNApSAcK IDNot Available
Chemspider ID4516050
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5363741
PDB IDNot Available
ChEBI ID49250
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1035361
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.