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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:41:47 UTC
Update Date2022-03-07 03:17:52 UTC
HMDB IDHMDB0062288
Secondary Accession Numbers
  • HMDB62288
Metabolite Identification
Common Name12(13)-epoxy-6Z,9Z-octadecadienoic acid
Description12(13)-epoxy-6Z,9Z-octadecadienoic acid is classified as a member of the Long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 12(13)-epoxy-6Z,9Z-octadecadienoic acid is considered to be practically insoluble (in water) and acidic. 12(13)-epoxy-6Z,9Z-octadecadienoic acid is an octadecanoid lipid molecule
Structure
Data?1563866291
Synonyms
ValueSource
g- 12(13)-EpodeGenerator
Γ- 12(13)-epodeGenerator
12(13)-Epoxy-6Z,9Z-octadecadienoateGenerator
Chemical FormulaC18H30O3
Average Molecular Weight294.435
Monoisotopic Molecular Weight294.219494826
IUPAC Name(6Z,9Z)-11-(3-pentyloxiran-2-yl)undeca-6,9-dienoic acid
Traditional Namegamma- 12(13)-EpODE
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC
InChI Identifier
InChI=1S/C18H30O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h4-5,8,11,16-17H,2-3,6-7,9-10,12-15H2,1H3,(H,19,20)/b5-4-,11-8-
InChI KeyTVHXKPMFCYEQTM-YMVJEYMASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Unsaturated fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00086 g/lALOGPS
LogP5.77ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.77ALOGPS
logP5.12ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.92ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity88.04 m³·mol⁻¹ChemAxon
Polarizability35.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.90131661259
DarkChem[M-H]-178.80531661259
DeepCCS[M+H]+177.70430932474
DeepCCS[M-H]-175.34630932474
DeepCCS[M-2H]-209.19130932474
DeepCCS[M+Na]+184.4230932474
AllCCS[M+H]+180.632859911
AllCCS[M+H-H2O]+177.632859911
AllCCS[M+NH4]+183.432859911
AllCCS[M+Na]+184.232859911
AllCCS[M-H]-181.232859911
AllCCS[M+Na-2H]-182.532859911
AllCCS[M+HCOO]-184.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12(13)-epoxy-6Z,9Z-octadecadienoic acid[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC3648.5Standard polar33892256
12(13)-epoxy-6Z,9Z-octadecadienoic acid[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC2122.2Standard non polar33892256
12(13)-epoxy-6Z,9Z-octadecadienoic acid[H]\C(CCCCC(O)=O)=C(/[H])CC([H])=C([H])CC1OC1CCCCC2329.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12(13)-epoxy-6Z,9Z-octadecadienoic acid,1TMS,isomer #1CCCCCC1OC1CC=CC/C=C\CCCCC(=O)O[Si](C)(C)C2295.0Semi standard non polar33892256
12(13)-epoxy-6Z,9Z-octadecadienoic acid,1TBDMS,isomer #1CCCCCC1OC1CC=CC/C=C\CCCCC(=O)O[Si](C)(C)C(C)(C)C2539.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9560000000-91d67664caa2712aeb5c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0pi9-9261000000-9c42141ae849232405492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 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 - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 10V, Positive-QTOFsplash10-004j-0190000000-dde04def7b967130ae182017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Positive-QTOFsplash10-00c9-9850000000-fb7226539be789b12a462017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Positive-QTOFsplash10-052o-9500000000-290c66f25bce77f7bf552017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 10V, Negative-QTOFsplash10-0006-0090000000-cce5355b11c1101b8fa32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Negative-QTOFsplash10-002f-2190000000-946e255f20debfcde94d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Negative-QTOFsplash10-052f-9200000000-d2ad3cbc0a3ec00eb6622017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 10V, Positive-QTOFsplash10-004j-2390000000-33d7311e43dd54a5484c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Positive-QTOFsplash10-0adi-8980000000-73fc9f6813735a3c06062021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Positive-QTOFsplash10-0a7l-9300000000-9c4b0f3686980fcacfdd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 10V, Negative-QTOFsplash10-002f-0090000000-cb47cf94994cf28d8b0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 20V, Negative-QTOFsplash10-0006-0290000000-9c4ee4ff5ad0e38154ec2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(13)-epoxy-6Z,9Z-octadecadienoic acid 40V, Negative-QTOFsplash10-052f-6590000000-6aab057804665cd270572021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061065
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.