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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:08 UTC
Update Date2021-09-14 15:44:19 UTC
HMDB IDHMDB0010212
Secondary Accession Numbers
  • HMDB10212
Metabolite Identification
Common Name17,18-EpETE
Description17,18-EpETE, also known as 17,18-eeq or 17R,18S-epete, 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. Thus, 17,18-epete is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 17,18-EpETE.
Structure
Data?1582752797
Synonyms
ValueSource
17(18)-Epoxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidChEBI
17,18-EEQChEBI
17,18-EETeTrChEBI
17,18-Epoxyeicosatetraenoic acidChEBI
17,18-Epoxyicosatetraenoic acidChEBI
17(18)-Epoxy-5Z,8Z,11Z,14Z-eicosatetraenoateGenerator
17,18-EpoxyeicosatetraenoateGenerator
17,18-EpoxyicosatetraenoateGenerator
(5E,8E,11E,14E)-16-(3-Ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoateHMDB
(5E,8E,11E,14E)-16-(3-Ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acidHMDB
(5Z,8Z,11Z,14Z)-(17R,18S)-17,18-Epoxyicosa-5,8,11,14-tetraenoateHMDB
(5Z,8Z,11Z,14Z)-(17R,18S)-17,18-Epoxyicosa-5,8,11,14-tetraenoic acidHMDB
17,18-Epoxy-5,8,11,14-eicosatetraenoateHMDB
17,18-Epoxy-5,8,11,14-eicosatetraenoic acidHMDB
17R,18S-EpETEHMDB
17R,18S-Epoxy-5Z,8Z,11Z,14Z-eicosatetraenoateHMDB
17R,18S-Epoxy-5Z,8Z,11Z,14Z-eicosatetraenoic acidHMDB
17R,18S-Epoxy-5Z,8Z,11Z,14Z-icosatetraenoateHMDB
17R,18S-Epoxy-5Z,8Z,11Z,14Z-icosatetraenoic acidHMDB
17,18-EpETEMeSH
Chemical FormulaC20H30O3
Average Molecular Weight318.4504
Monoisotopic Molecular Weight318.219494826
IUPAC Name(5Z,8Z,11Z,14Z)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid
Traditional Name(5Z,8Z,11Z,14Z)-16-(3-ethyloxiran-2-yl)hexadeca-5,8,11,14-tetraenoic acid
CAS Registry Number131339-23-6
SMILES
CCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-18-19(23-18)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-20(21)22/h3,5-6,8-9,11-12,14,18-19H,2,4,7,10,13,15-17H2,1H3,(H,21,22)/b5-3-,8-6-,11-9-,14-12-
InChI KeyGPQVVJQEBXAKBJ-JPURVOHMSA-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
Disposition

Biological location

Source

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 Solubility0.00054 g/LALOGPS
logP5.8ALOGPS
logP5.29ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity99.47 m³·mol⁻¹ChemAxon
Polarizability37.08 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]+184.15931661259
DarkChem[M-H]-184.60431661259
DeepCCS[M+H]+183.44130932474
DeepCCS[M-H]-181.08330932474
DeepCCS[M-2H]-213.9730932474
DeepCCS[M+Na]+189.53530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
17,18-EpETECCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O3741.0Standard polar33892256
17,18-EpETECCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O2269.6Standard non polar33892256
17,18-EpETECCC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O2507.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
17,18-EpETE,1TMS,isomer #1CCC1OC1C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2461.8Semi standard non polar33892256
17,18-EpETE,1TBDMS,isomer #1CCC1OC1C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2717.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 17,18-EpETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6390000000-d18e27b44e7a49b3e4ce2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17,18-EpETE GC-MS (1 TMS) - 70eV, Positivesplash10-00bc-9154000000-c2f4f6ce4606242675e32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 17,18-EpETE 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 - 17,18-EpETE 10V, Positive-QTOFsplash10-0udi-1049000000-ae6f07715e6dcd0b814d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 20V, Positive-QTOFsplash10-0uel-4292000000-a75a4e58b49cb4e60c6e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 40V, Positive-QTOFsplash10-0f76-9640000000-6f31e736197cf906a1e42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 10V, Negative-QTOFsplash10-014i-0059000000-4eb6574ac2eababaa84d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 20V, Negative-QTOFsplash10-01ba-3094000000-c495a1a93b12a813b7eb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 40V, Negative-QTOFsplash10-052f-9020000000-6eca2b0aedb19788dd2b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 10V, Positive-QTOFsplash10-0gb9-5579000000-6c6d49a8631fa5113a762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 20V, Positive-QTOFsplash10-0kur-6893000000-2bc0e61e26753b5c136e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 40V, Positive-QTOFsplash10-014l-9700000000-1bd6ac94e569471691072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 10V, Negative-QTOFsplash10-014i-0059000000-a96f76898aca40cfd5652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 20V, Negative-QTOFsplash10-014j-2094000000-80e6f67909c091363ec12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 17,18-EpETE 40V, Negative-QTOFsplash10-0a4l-9160000000-7753dd905140438a026c2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000111 +/- 0.000031 uMAdult (>18 years old)Not Specified
Normal
details
BloodDetected and Quantified0.0000733 +/- 0.000095 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 IDFDB027367
KNApSAcK IDNot Available
Chemspider ID17220772
KEGG Compound IDC13843
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061089
PDB IDNot Available
ChEBI ID72853
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. Oliw EH: Biosynthesis of 18(RD)-hydroxyeicosatetraenoic acid from arachidonic acid by microsomes of monkey seminal vesicles. Some properties of a novel fatty acid omega 3-hydroxylase and omega 3-epoxygenase. J Biol Chem. 1989 Oct 25;264(30):17845-53. [PubMed:2509448 ]