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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:51:32 UTC
Update Date2022-03-07 02:55:25 UTC
HMDB IDHMDB0037606
Secondary Accession Numbers
  • HMDB37606
Metabolite Identification
Common Name13-Nor-6-eremophilene-8,11-dione
Description13-Nor-6-eremophilene-8,11-dione belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on 13-Nor-6-eremophilene-8,11-dione.
Structure
Data?1563863059
SynonymsNot Available
Chemical FormulaC14H20O2
Average Molecular Weight220.3074
Monoisotopic Molecular Weight220.146329884
IUPAC Name3-acetyl-4a,5-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one
Traditional Name3-acetyl-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one
CAS Registry Number348119-85-7
SMILES
CC1CCCC2CC(=O)C(=CC12C)C(C)=O
InChI Identifier
InChI=1S/C14H20O2/c1-9-5-4-6-11-7-13(16)12(10(2)15)8-14(9,11)3/h8-9,11H,4-7H2,1-3H3
InChI KeyXNORMQKITMTNGH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.092 g/LALOGPS
logP2.75ALOGPS
logP2.99ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)18.43ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.49 m³·mol⁻¹ChemAxon
Polarizability25.14 ųChemAxon
Number of Rings2ChemAxon
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]+151.17131661259
DarkChem[M-H]-147.74231661259
DeepCCS[M-2H]-186.89530932474
DeepCCS[M+Na]+162.94730932474
AllCCS[M+H]+150.532859911
AllCCS[M+H-H2O]+146.632859911
AllCCS[M+NH4]+154.232859911
AllCCS[M+Na]+155.232859911
AllCCS[M-H]-158.032859911
AllCCS[M+Na-2H]-158.532859911
AllCCS[M+HCOO]-159.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
13-Nor-6-eremophilene-8,11-dioneCC1CCCC2CC(=O)C(=CC12C)C(C)=O2341.4Standard polar33892256
13-Nor-6-eremophilene-8,11-dioneCC1CCCC2CC(=O)C(=CC12C)C(C)=O1638.0Standard non polar33892256
13-Nor-6-eremophilene-8,11-dioneCC1CCCC2CC(=O)C(=CC12C)C(C)=O1746.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #1CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C1991.3Semi standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #1CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C1754.2Standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #2C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O1992.3Semi standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,1TMS,isomer #2C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O1821.5Standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,2TMS,isomer #1C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C2054.6Semi standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,2TMS,isomer #1C=C(O[Si](C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C1914.6Standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #1CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C2232.5Semi standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #1CC(=O)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C1972.2Standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O2237.8Semi standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2CC1=O2066.5Standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C2518.5Semi standard non polar33892256
13-Nor-6-eremophilene-8,11-dione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C1=CC2(C)C(C)CCCC2C=C1O[Si](C)(C)C(C)(C)C2305.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 13-Nor-6-eremophilene-8,11-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-1930000000-2ef2ca251c5d907b79502017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13-Nor-6-eremophilene-8,11-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 13-Nor-6-eremophilene-8,11-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 - 13-Nor-6-eremophilene-8,11-dione 10V, Positive-QTOFsplash10-00di-0290000000-b3313219166b82100f342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Positive-QTOFsplash10-00di-3950000000-703f3cda362bbddf0f962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Positive-QTOFsplash10-05mo-7910000000-456ba727158f6c341e8e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 10V, Negative-QTOFsplash10-014i-0090000000-61a957fdc7b07681d3e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Negative-QTOFsplash10-014i-0190000000-be50c614e08e682057822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Negative-QTOFsplash10-0h03-3920000000-80e43f5bc224bd1418662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 10V, Positive-QTOFsplash10-00di-0190000000-c84fe0fab830470275852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Positive-QTOFsplash10-0a4l-5910000000-92335122ee40e3eeb7f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Positive-QTOFsplash10-0006-9810000000-948ca7f16f6d09a1b7432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 10V, Negative-QTOFsplash10-014i-0090000000-b5ccca7192d7ca1541682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 20V, Negative-QTOFsplash10-014i-0090000000-8bd5034e70e2446446f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 13-Nor-6-eremophilene-8,11-dione 40V, Negative-QTOFsplash10-0i2c-1930000000-ee7c7892d15198f58c1e2021-09-22Wishart 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 IDFDB016719
KNApSAcK IDC00057359
Chemspider ID35014444
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85288059
PDB IDNot Available
ChEBI IDNot Available
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.