Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:16 UTC
Update Date2021-09-14 15:48:05 UTC
HMDB IDHMDB0010220
Secondary Accession Numbers
  • HMDB10220
Metabolite Identification
Common Name9(10)-EpODE
Description9(10)-EpODE is an epoxy fatty acid where linolenic acid has been epoxidized at the 9-10 positions through the action of cytochrome P450 epoxygenases. Epoxy fatty acids are termed 'leukotoxins' (the term includes a range of diverse compounds), because they produce their primary toxic effects against leukocytes. At high dosages, they have toxic cardiovascular effects, which can even result in death.
Structure
Data?1582752798
Synonyms
ValueSource
9(10)-Epoxy-12Z,15Z-octadecadienoateHMDB
9(10)-Epoxy-12Z,15Z-octadecadienoic acidHMDB
a-9(10)-EpODEHMDB
alpha-9(10)-EpODEHMDB
Α-9(10)-epodeHMDB
9,10-Epoxy-12,15-octadecadienoateHMDB
Chemical FormulaC18H30O3
Average Molecular Weight294.429
Monoisotopic Molecular Weight294.219494826
IUPAC Name8-{3-[(2Z,5Z)-octa-2,5-dien-1-yl]oxiran-2-yl}octanoic acid
Traditional Name8-{3-[(2Z,5Z)-octa-2,5-dien-1-yl]oxiran-2-yl}octanoic acid
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/CC1OC1CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H30O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h3-4,7,10,16-17H,2,5-6,8-9,11-15H2,1H3,(H,19,20)/b4-3-,10-7-
InChI KeyJTEGNNHWOIJBJZ-ZJSQCTGTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
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 Solubility0.0009 g/LALOGPS
logP10(5.73) g/LALOGPS
logP10(5.12) g/LChemAxon
logS10(-5.5) g/LALOGPS
pKa (Strongest Acidic)4.62ChemAxon
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
Polarizability36.16 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]+176.40231661259
DarkChem[M-H]-174.59931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9(10)-EpODECC\C=C/C\C=C/CC1OC1CCCCCCCC(O)=O3512.0Standard polar33892256
9(10)-EpODECC\C=C/C\C=C/CC1OC1CCCCCCCC(O)=O2133.1Standard non polar33892256
9(10)-EpODECC\C=C/C\C=C/CC1OC1CCCCCCCC(O)=O2304.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9(10)-EpODE,1TMS,isomer #1CC/C=C\C/C=C\CC1OC1CCCCCCCC(=O)O[Si](C)(C)C2300.7Semi standard non polar33892256
9(10)-EpODE,1TBDMS,isomer #1CC/C=C\C/C=C\CC1OC1CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2548.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9(10)-EpODE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abc-3940000000-1f0f4a62242b0f623dca2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9(10)-EpODE GC-MS (1 TMS) - 70eV, Positivesplash10-0fki-8971000000-2334dde501a14afab8912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9(10)-EpODE 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 - 9(10)-EpODE 10V, Positive-QTOFsplash10-002b-0190000000-1f4bcf7cecd464a4cef52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 20V, Positive-QTOFsplash10-05bb-7940000000-d4d3aecfb5a46c29b87e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 40V, Positive-QTOFsplash10-05o4-9200000000-92b2236bed3dcd93ab752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 10V, Negative-QTOFsplash10-0006-0390000000-99a0826addea664893772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 20V, Negative-QTOFsplash10-0007-1590000000-099addac82e049ad553f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 40V, Negative-QTOFsplash10-052f-9700000000-e91acdd1a795f26748142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 10V, Positive-QTOFsplash10-056s-4390000000-f6f3268fdbcae05455782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 20V, Positive-QTOFsplash10-0a59-9420000000-898456a641f0a16fa57c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 40V, Positive-QTOFsplash10-05po-9200000000-22e67b7cc636db8ab7312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 10V, Negative-QTOFsplash10-0006-0090000000-faa7c22929287494d9602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 20V, Negative-QTOFsplash10-0006-0390000000-f07cb340ea044ce1762d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9(10)-EpODE 40V, Negative-QTOFsplash10-002f-9630000000-da8e5c466b54002eddfa2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00208 +/- 0.000075 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.00208 +/- 0.000075 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00165 +/- 0.0023 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003106
KNApSAcK IDNot Available
Chemspider ID17220743
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061060
PDB IDNot Available
ChEBI ID88441
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 ReferencesNot Available