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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:07 UTC
Update Date2023-02-21 17:21:17 UTC
HMDB IDHMDB0031737
Secondary Accession Numbers
  • HMDB31737
Metabolite Identification
Common Namedelta-Methylionone
Descriptiondelta-Methylionone, also known as δ-methylionone, 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 delta-Methylionone.
Structure
Data?1677000077
Synonyms
ValueSource
Δ-methyliononeGenerator
3-Methyl-b-iononeHMDB
4-(2,6, 6-Trimethyl-1-cyclohexenyl)-3-methyl-3-buten-2-oneHMDB
4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-methyl-3-buten-2-oneHMDB
b-iso-MethyliononeHMDB
D-MethyliononeHMDB
delta-IraldeineHMDB
FEMA 2713HMDB
Isomethyl-beta-iononeHMDB
Methyl-delta-iononeHMDB
Chemical FormulaC14H22O
Average Molecular Weight206.3239
Monoisotopic Molecular Weight206.167065326
IUPAC Name(3E)-3-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
Traditional Name(3E)-3-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
CAS Registry Number79-89-0
SMILES
CC(=O)C(\C)=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h9H,6-8H2,1-5H3/b11-9+
InChI KeyNSSHGPBKKVJJMM-PKNBQFBNSA-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-branched alpha,beta-unsaturated-ketone
  • 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 Point62.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point301.28 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.31 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.008 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP4.49ALOGPS
logP3.67ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)19.58ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.18 m³·mol⁻¹ChemAxon
Polarizability25.38 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]+159.66130932474
DeepCCS[M-H]-157.30330932474
DeepCCS[M-2H]-190.29730932474
DeepCCS[M+Na]+165.75430932474
AllCCS[M+H]+147.332859911
AllCCS[M+H-H2O]+143.432859911
AllCCS[M+NH4]+150.932859911
AllCCS[M+Na]+152.032859911
AllCCS[M-H]-155.232859911
AllCCS[M+Na-2H]-156.232859911
AllCCS[M+HCOO]-157.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
delta-MethyliononeCC(=O)C(\C)=C\C1=C(C)CCCC1(C)C1820.4Standard polar33892256
delta-MethyliononeCC(=O)C(\C)=C\C1=C(C)CCCC1(C)C1538.9Standard non polar33892256
delta-MethyliononeCC(=O)C(\C)=C\C1=C(C)CCCC1(C)C1506.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
delta-Methylionone,1TMS,isomer #1C=C(O[Si](C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C1644.1Semi standard non polar33892256
delta-Methylionone,1TMS,isomer #1C=C(O[Si](C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C1681.4Standard non polar33892256
delta-Methylionone,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C1860.3Semi standard non polar33892256
delta-Methylionone,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C1906.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - delta-Methylionone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-2900000000-591f5c40bdcd447ac6eb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - delta-Methylionone 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 - delta-Methylionone 10V, Positive-QTOFsplash10-0a4i-3980000000-03e8a62eda77589e1b8e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 20V, Positive-QTOFsplash10-05n0-6910000000-036ff3133945a2d001592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 40V, Positive-QTOFsplash10-1003-9300000000-8d04eebaeb88fb42999f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 10V, Negative-QTOFsplash10-0a4i-0190000000-ceafb1926e4e5978a7462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 20V, Negative-QTOFsplash10-0bt9-2890000000-bf7cbeb1e62dc5ec9d752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 40V, Negative-QTOFsplash10-02ga-4900000000-f7957e4beda95b1799092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 10V, Positive-QTOFsplash10-000i-1910000000-728c239e8cf3697cabff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 20V, Positive-QTOFsplash10-0600-7900000000-66cbf6ef9b7f29e5928e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 40V, Positive-QTOFsplash10-0006-9300000000-52196c794798dcaf64672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 10V, Negative-QTOFsplash10-0a4i-0490000000-626a1896cc5089dca3582021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 20V, Negative-QTOFsplash10-0a4i-0790000000-56276d7995cc937849ef2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - delta-Methylionone 40V, Negative-QTOFsplash10-0kuf-7910000000-32dfec568909b74046282021-09-23Wishart 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 IDFDB008405
KNApSAcK IDNot Available
Chemspider ID4522526
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5372195
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1045331
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.