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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:15:58 UTC
Update Date2021-10-13 06:47:38 UTC
HMDB IDHMDB0035306
Secondary Accession Numbers
  • HMDB35306
Metabolite Identification
Common NameEpishyobunone
DescriptionEpishyobunone belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Based on a literature review a small amount of articles have been published on Epishyobunone.
Structure
Data?1563862697
Synonyms
ValueSource
Epi-shyobunoneHMDB
Chemical FormulaC15H24O
Average Molecular Weight220.3505
Monoisotopic Molecular Weight220.18271539
IUPAC Name3-ethenyl-3-methyl-2-(prop-1-en-2-yl)-6-(propan-2-yl)cyclohexan-1-one
Traditional Name3-ethenyl-6-isopropyl-3-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one
CAS Registry Number39020-72-9
SMILES
CC(C)C1CCC(C)(C=C)C(C(C)=C)C1=O
InChI Identifier
InChI=1S/C15H24O/c1-7-15(6)9-8-12(10(2)3)14(16)13(15)11(4)5/h7,10,12-13H,1,4,8-9H2,2-3,5-6H3
InChI KeyGWHRSRIPLDHJHR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentElemane sesquiterpenoids
Alternative Parents
Substituents
  • Elemane sesquiterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point289.00 to 291.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.85 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.869 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0047 g/LALOGPS
logP10(4.26) g/LALOGPS
logP10(4.42) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Acidic)18.83ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity69.14 m³·mol⁻¹ChemAxon
Polarizability26.92 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
DarkChem[M+H]+152.40231661259
DarkChem[M-H]-148.45431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EpishyobunoneCC(C)C1CCC(C)(C=C)C(C(C)=C)C1=O1859.8Standard polar33892256
EpishyobunoneCC(C)C1CCC(C)(C=C)C(C(C)=C)C1=O1500.5Standard non polar33892256
EpishyobunoneCC(C)C1CCC(C)(C=C)C(C(C)=C)C1=O1495.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epishyobunone,1TMS,isomer #1C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C)C1C(=C)C1585.3Semi standard non polar33892256
Epishyobunone,1TMS,isomer #1C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C)C1C(=C)C1590.9Standard non polar33892256
Epishyobunone,1TMS,isomer #2C=CC1(C)CCC(C(C)C)C(O[Si](C)(C)C)=C1C(=C)C1593.0Semi standard non polar33892256
Epishyobunone,1TMS,isomer #2C=CC1(C)CCC(C(C)C)C(O[Si](C)(C)C)=C1C(=C)C1615.2Standard non polar33892256
Epishyobunone,1TBDMS,isomer #1C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1C(=C)C1814.9Semi standard non polar33892256
Epishyobunone,1TBDMS,isomer #1C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1C(=C)C1804.4Standard non polar33892256
Epishyobunone,1TBDMS,isomer #2C=CC1(C)CCC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C(=C)C1822.6Semi standard non polar33892256
Epishyobunone,1TBDMS,isomer #2C=CC1(C)CCC(C(C)C)C(O[Si](C)(C)C(C)(C)C)=C1C(=C)C1870.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epishyobunone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pc0-9410000000-47baddddcebabd25711d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epishyobunone 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 - Epishyobunone 10V, Positive-QTOFsplash10-00di-0390000000-e67371c5e37ca756e3762015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 20V, Positive-QTOFsplash10-0adr-7930000000-756914a4b86869c655a52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 40V, Positive-QTOFsplash10-0pb9-9200000000-9d10a9b639db043248a02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 10V, Negative-QTOFsplash10-014i-0090000000-30460f87bb3aeedb11672015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 20V, Negative-QTOFsplash10-014i-0390000000-785d43269b05824b5b262015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 40V, Negative-QTOFsplash10-01u9-3920000000-2444b3d3fa6e6b4eb6232015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 10V, Positive-QTOFsplash10-00di-0490000000-2acced60149d51d648082021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 20V, Positive-QTOFsplash10-00rl-5920000000-b779bba8e1d65ed5280b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 40V, Positive-QTOFsplash10-05mx-9600000000-2d0693c4788b2f7c5cbf2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 10V, Negative-QTOFsplash10-014i-0090000000-4af4c4ee1c4acef7e18b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 20V, Negative-QTOFsplash10-016r-0790000000-57b7b68504f8e6d39bf32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epishyobunone 40V, Negative-QTOFsplash10-01t9-1920000000-d0c1af37ba9a9d4abf482021-09-25Wishart 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 IDFDB013974
KNApSAcK IDC00012003
Chemspider ID514038
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound591309
PDB IDNot Available
ChEBI ID168444
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1596061
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.