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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:11:48 UTC
Update Date2023-02-21 17:24:43 UTC
HMDB IDHMDB0035245
Secondary Accession Numbers
  • HMDB35245
Metabolite Identification
Common Name1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one
Description1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 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 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one.
Structure
Data?1677000283
Synonyms
ValueSource
(1E)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-oneHMDB
(e)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)pent-1-en-3-oneHMDB
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)pent-1-en-3-oneHMDB
1-(2,6,6-Trimethyl-2-cyclohexene-1-yl)-1-penten-3-oneHMDB
1-2,6,6-Trimethylcyclohex-2-en-1-ylHMDB
1-Methyl-a-iononeHMDB
5-(2,6,6-Trimethyl-2-cyclohexenyl)-4-penten-3-oneHMDB
6-MethyliononeHMDB
alpha-CetoneHMDB
alpha-MethyliononeHMDB
FEMA 2711HMDB
Methyl-iononeHMDB
MethyliononeHMDB, MeSH
N-Methyl-a-iononeHMDB
Pent-1-en-3-oneHMDB
Chemical FormulaC14H22O
Average Molecular Weight206.3239
Monoisotopic Molecular Weight206.167065326
IUPAC Name(1E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)pent-1-en-3-one
Traditional Nameirone
CAS Registry Number127-42-4
SMILES
CCC(=O)\C=C\C1C(C)=CCCC1(C)C
InChI Identifier
InChI=1S/C14H22O/c1-5-12(15)8-9-13-11(2)7-6-10-14(13,3)4/h7-9,13H,5-6,10H2,1-4H3/b9-8+
InChI KeyVPKMGDRERYMTJX-CMDGGOBGSA-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
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point238.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3.33 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.393 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP4.57ALOGPS
logP4.02ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.72 m³·mol⁻¹ChemAxon
Polarizability25.05 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]+154.39930932474
DeepCCS[M-H]-152.00330932474
DeepCCS[M-2H]-185.13730932474
DeepCCS[M+Na]+160.43630932474
AllCCS[M+H]+148.532859911
AllCCS[M+H-H2O]+144.632859911
AllCCS[M+NH4]+152.232859911
AllCCS[M+Na]+153.332859911
AllCCS[M-H]-155.432859911
AllCCS[M+Na-2H]-156.232859911
AllCCS[M+HCOO]-157.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-oneCCC(=O)\C=C\C1C(C)=CCCC1(C)C1905.5Standard polar33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-oneCCC(=O)\C=C\C1C(C)=CCCC1(C)C1501.2Standard non polar33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-oneCCC(=O)\C=C\C1C(C)=CCCC1(C)C1547.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one,1TMS,isomer #1CC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C1761.6Semi standard non polar33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one,1TMS,isomer #1CC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C1720.9Standard non polar33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one,1TBDMS,isomer #1CC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C1995.8Semi standard non polar33892256
1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one,1TBDMS,isomer #1CC=C(/C=C/C1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C1953.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-054w-4900000000-b045f61f4b940110d85e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 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 - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 10V, Positive-QTOFsplash10-0a4i-1790000000-09686e5ff6b3a58b4acf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 20V, Positive-QTOFsplash10-053j-6910000000-fecd50f9bb9d5c4c3c912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 40V, Positive-QTOFsplash10-0ktu-9200000000-785074f4dff70d3ce57b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 10V, Negative-QTOFsplash10-0a4i-0190000000-bad4fe272ecf0676b0f62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 20V, Negative-QTOFsplash10-0a4i-3690000000-4c790dd84825b7f4dda32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 40V, Negative-QTOFsplash10-05ts-4900000000-a18d770da8832df84b3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 10V, Negative-QTOFsplash10-0a4i-0090000000-2d8ac504a1490d38e7ad2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 20V, Negative-QTOFsplash10-00dj-1910000000-5813a9f1a635d15878382021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 40V, Negative-QTOFsplash10-0q2a-8910000000-94c9ddb49918998223f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 10V, Positive-QTOFsplash10-052r-1910000000-52aca7acb363bd0c28c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 20V, Positive-QTOFsplash10-0079-4900000000-0d6be0132d5d641de6d12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one 40V, Positive-QTOFsplash10-066r-9500000000-9bdb96bba0f00804a71e2021-09-22Wishart 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
  • 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 IDFDB013905
KNApSAcK IDNot Available
Chemspider ID4521710
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5371084
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1596201
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamazaki Y, Hayashi Y, Arita M, Hieda T, Mikami Y: Microbial Conversion of alpha-Ionone, alpha-Methylionone, and alpha-Isomethylionone. Appl Environ Microbiol. 1988 Oct;54(10):2354-60. [PubMed:16347747 ]
  2. Politano VT, Lewis EM, Hoberman AM, Christian MS, Diener RM, Api AM: Evaluation of the developmental toxicity of alpha-iso-methylionone in rats. Int J Toxicol. 2007 May-Jun;26(3):271-6. [PubMed:17564909 ]
  3. Lapczynski A, Lalko J, Politano VT, McGinty D, Bhatia S, Letizia CS, Api AM: Fragrance material review on alpha-iso-methylionone. Food Chem Toxicol. 2007;45 Suppl 1:S280-9. Epub 2007 Sep 14. [PubMed:18037210 ]
  4. Politano VT, Lapczynski AA, Ritacco G, Api AM: Ninety-day toxicity study of alpha-iso-methylionone in rats. Int J Toxicol. 2012 Nov-Dec;31(6):595-601. doi: 10.1177/1091581812466116. [PubMed:23283689 ]
  5. Bernaola G, Escayol P, Fernandez E, Fernandez de Corres L: Contact dermatitis from methylionone fragrance. Contact Dermatitis. 1989 Jan;20(1):71-2. [PubMed:2914440 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.