Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:10 UTC
Update Date2022-03-07 02:53:26 UTC
HMDB IDHMDB0032681
Secondary Accession Numbers
  • HMDB32681
Metabolite Identification
Common Name10alpha-4,5-Seco-11-eudesmene-4,5-dione
Description10alpha-4,5-Seco-11-eudesmene-4,5-dione belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a small amount of articles have been published on 10alpha-4,5-Seco-11-eudesmene-4,5-dione.
Structure
Data?1563862292
Synonyms
ValueSource
10a-4,5-Seco-11-eudesmene-4,5-dioneGenerator
10Α-4,5-seco-11-eudesmene-4,5-dioneGenerator
Chemical FormulaC15H24O2
Average Molecular Weight236.3499
Monoisotopic Molecular Weight236.177630012
IUPAC Name2-methyl-2-(4-oxopentyl)-5-(prop-1-en-2-yl)cyclohexan-1-one
Traditional Name2-methyl-2-(4-oxopentyl)-5-(prop-1-en-2-yl)cyclohexan-1-one
CAS Registry Number210106-14-2
SMILES
CC(=O)CCCC1(C)CCC(CC1=O)C(C)=C
InChI Identifier
InChI=1S/C15H24O2/c1-11(2)13-7-9-15(4,14(17)10-13)8-5-6-12(3)16/h13H,1,5-10H2,2-4H3
InChI KeyFCPUGTGXHMJFQH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • 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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP3ALOGPS
logP3.6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.82 m³·mol⁻¹ChemAxon
Polarizability28.11 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]+157.64231661259
DarkChem[M-H]-154.22231661259
DeepCCS[M+H]+158.79830932474
DeepCCS[M-H]-156.4430932474
DeepCCS[M-2H]-190.12930932474
DeepCCS[M+Na]+165.06930932474
AllCCS[M+H]+159.132859911
AllCCS[M+H-H2O]+155.532859911
AllCCS[M+NH4]+162.432859911
AllCCS[M+Na]+163.432859911
AllCCS[M-H]-164.232859911
AllCCS[M+Na-2H]-165.032859911
AllCCS[M+HCOO]-166.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
10alpha-4,5-Seco-11-eudesmene-4,5-dioneCC(=O)CCCC1(C)CCC(CC1=O)C(C)=C2321.2Standard polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dioneCC(=O)CCCC1(C)CCC(CC1=O)C(C)=C1696.9Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dioneCC(=O)CCCC1(C)CCC(CC1=O)C(C)=C1814.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #1C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C)C(=O)C11922.4Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #1C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C)C(=O)C11883.8Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCCC(C)=O)CC11818.2Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCCC(C)=O)CC11798.9Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #3C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C1881.0Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #3C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C1901.4Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C)CC11916.5Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C)CC11914.5Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #2C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C)O[Si](C)(C)C1872.9Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #2C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C)O[Si](C)(C)C1954.5Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #1C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(=O)C12177.7Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #1C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(=O)C12115.9Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCCC(C)=O)CC12062.3Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #2C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCCC(C)=O)CC11943.3Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #3C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C(C)(C)C2132.3Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #3C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C(C)(C)C2128.8Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)CC12426.9Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #1C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)CC12239.6Standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #2C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2358.9Semi standard non polar33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #2C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2252.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9410000000-d965b99e47f46bd79d772017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 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 - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Positive-QTOFsplash10-00kr-1290000000-6c31e3291e760794d6e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Positive-QTOFsplash10-014i-6940000000-dcca84c66429ebb47c1c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Positive-QTOFsplash10-0fr7-9100000000-94889a337c289272bfde2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Negative-QTOFsplash10-000i-0090000000-ac11b5bf352850cba2c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Negative-QTOFsplash10-000i-2290000000-3a314be6ddd7bfeb47232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Negative-QTOFsplash10-0aor-8920000000-c298e4b02ac636d4f2902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Positive-QTOFsplash10-014r-0890000000-5a310ebb42a7a531bfc32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Positive-QTOFsplash10-00kr-5930000000-50205d0d53d6441907fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Positive-QTOFsplash10-052f-9800000000-9aaf2694ce0e54dcda8b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Negative-QTOFsplash10-000i-0090000000-c0031dc201eac6b6350a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Negative-QTOFsplash10-0f7a-1980000000-3c747b90e87c3742cbf62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Negative-QTOFsplash10-0002-1900000000-3b039498ed7b890a14a72021-09-23Wishart 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 IDFDB010637
KNApSAcK IDNot Available
Chemspider ID35013466
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85204671
PDB IDNot Available
ChEBI ID173704
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.