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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:46 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002283
Secondary Accession Numbers
  • HMDB02283
Metabolite Identification
Common Name14R,15S-EpETrE
Description14R,15S-EpETrE is the dominant extracellular metabolite of epoxygenase products of arachidonic acid released from human luteinised granulosa cells. Epoxyeicosatrienoic acids (EpETrEs) have been reported recently having vasodilatory effects and a role of P-450-dependent arachidonic acid monooxygenase metabolites is suggested in vasoregulation. The physiological role of this compound has not been totally established, although in other tissues EpETrEs are mainly involved in hormone production and in the vascular and renal systems. Some studies have implicated epoxygenase metabolites of arachidonic acid in the control of steroidogenesis in luteinised granulosa cells. (PMID: 12749593 , 12361727 , 1650001 ).
Structure
Data?1582752241
Synonyms
ValueSource
(14R,15S)-EpETrEChEBI
(14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acidChEBI
(14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoic acidChEBI
14(S),15(R)-EETChEBI
14R,15S-Epoxy-5Z,8Z,11Z-eicosatrienoic acidChEBI
(14R,15S)-Epoxy-(5Z,8Z,11Z)-eicosatrienoateGenerator
(14R,15S)-Epoxy-(5Z,8Z,11Z)-icosatrienoateGenerator
14R,15S-Epoxy-5Z,8Z,11Z-eicosatrienoateGenerator
14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoateHMDB
14(S),15(R)-Epoxy-(5Z,8Z,11Z)-eicosatrienoic acidHMDB
14,15-EETHMDB
14,15-Epoxy-5,8,11-eicosatrienoic acidHMDB
14,15-Epoxy-5,8,11-eicosatrienoic acid, (2alpha(5Z,8Z,11Z),3alpha)-isomerHMDB
14,15-Epoxyeicosatrienoic acidHMDB
14,15-Oxido-5,8,11-eicosatrienoic acidHMDB
14R,15S-EpETrEChEBI
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z)-13-[(2R,3S)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid
Traditional Name14R,15S-EpETrE
CAS Registry Number98103-48-1
SMILES
CCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m0/s1
InChI KeyJBSCUHKPLGKXKH-LLZJRKGESA-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
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.00032 g/LALOGPS
logP6.23ALOGPS
logP5.65ChemAxon
logS-6ALOGPS
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 Count14ChemAxon
Refractivity98.36 m³·mol⁻¹ChemAxon
Polarizability38.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+186.56431661259
DarkChem[M-H]-179.53131661259
DeepCCS[M+H]+188.57230932474
DeepCCS[M-H]-186.21430932474
DeepCCS[M-2H]-219.59130932474
DeepCCS[M+Na]+194.81830932474
AllCCS[M+H]+188.332859911
AllCCS[M+H-H2O]+185.532859911
AllCCS[M+NH4]+191.032859911
AllCCS[M+Na]+191.732859911
AllCCS[M-H]-188.032859911
AllCCS[M+Na-2H]-189.632859911
AllCCS[M+HCOO]-191.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
14R,15S-EpETrECCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O3780.1Standard polar33892256
14R,15S-EpETrECCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O2311.7Standard non polar33892256
14R,15S-EpETrECCCCC[C@@H]1O[C@@H]1C\C=C/C\C=C/C\C=C/CCCC(O)=O2448.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
14R,15S-EpETrE,1TMS,isomer #1CCCCC[C@@H]1O[C@@H]1C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2508.6Semi standard non polar33892256
14R,15S-EpETrE,1TBDMS,isomer #1CCCCC[C@@H]1O[C@@H]1C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2762.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 14R,15S-EpETrE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-7390000000-0a6ea9221818f7ca6b612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14R,15S-EpETrE GC-MS (1 TMS) - 70eV, Positivesplash10-00bj-9152000000-75e265bfced30aca2f552017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 14R,15S-EpETrE 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 - 14R,15S-EpETrE 10V, Positive-QTOFsplash10-0udi-1139000000-d1b1217f1a0ab449ee762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Positive-QTOFsplash10-0f80-9562000000-3a641d61ec600d27001a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Positive-QTOFsplash10-0f77-9610000000-4d2f2f7c7445ce34caa92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Negative-QTOFsplash10-014i-1029000000-03d83d003242098cb3c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Negative-QTOFsplash10-0gb9-4159000000-4a32a74e26b6a89788592017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Negative-QTOFsplash10-052f-9120000000-efc218792d62c8df73a52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Negative-QTOFsplash10-014i-0009000000-fa339ab07ef5a66d93e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Negative-QTOFsplash10-0gb9-2149000000-f932d9bc138901e04dad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Negative-QTOFsplash10-052f-9140000000-91f3f678f570fc1a1ff62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 10V, Positive-QTOFsplash10-0uki-2259000000-adfdaf1e87da0a4fbf5f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 20V, Positive-QTOFsplash10-0udr-9375000000-fdf50048f25a924a6bb22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 14R,15S-EpETrE 40V, Positive-QTOFsplash10-00mo-9200000000-f15fc52cfe999f85655e2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000134 +/- 0.000053 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000135 +/- 0.00008 uMAdult (>18 years old)Both
Normal
    • John W. Newman, U...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022946
KNApSAcK IDNot Available
Chemspider ID4446322
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283201
PDB IDNot Available
ChEBI ID132275
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceEnnis, Michael D.; Baze, Mark E. Asymmetric total synthesis of 14(R),15(S)-, 14(S),15(R)-, 14(R),15(R)-, and 14(S),15(S)-epoxyeicosatrienoic acids. Tetrahedron Letters (1986), 27(50), 6031-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zosmer A, Elder MG, Sullivan MH: The regulation of arachidonic acid metabolism in human first trimester trophoblast by cyclic AMP. Prostaglandins Other Lipid Mediat. 2003 Apr;71(1-2):43-53. [PubMed:12749593 ]
  2. Zosmer A, Elder MG, Sullivan MH: The production of progesterone and 5,6-epoxyeicosatrienoic acid by human granulosa cells. J Steroid Biochem Mol Biol. 2002 Aug;81(4-5):369-76. [PubMed:12361727 ]
  3. Hasunuma K, Terano T, Tamura Y, Yoshida S: Formation of epoxyeicosatrienoic acids from arachidonic acid by cultured rat aortic smooth muscle cell microsomes. Prostaglandins Leukot Essent Fatty Acids. 1991 Mar;42(3):171-5. [PubMed:1650001 ]