Record Information
Version3.6
Creation Date2006-08-13 15:33:17 UTC
Update Date2013-02-09 00:13:09 UTC
HMDB IDHMDB04264
Secondary Accession Numbers
  • HMDB11138
Metabolite Identification
Common Name14,15-Epoxy-5,8,11-eicosatrienoic acid
Description14,15-epoxy-5,8,11-eicosatrienoic acid is an epoxyeicosatrienoic acid (EET), a metabolite of arachidonic acid. The P450 eicosanoids epoxyeicosatrienoic acids (EETs) are endogenous lipid mediators produced by P450 epoxygenases and metabolized through multiple pathways including soluble epoxide hydrolase (sEH). The cytochrome P-450 (P450) monooxygenase pathway includes enzymes of the CYP1A, CYP2B, CYP2C, CYP2E, and CYP2J subfamilies that catalyze the formation of four regioisomeric products, 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid. EETs are produced in brain and perform important biological functions, including protection from ischemic injury. Both light flashes and direct glial stimulation produce vasodilatation mediated by EETs. EETs may be involved in the development of hypertension and endothelial dysfunction in DOCA-salt rats, but not in excessive collagen deposition or electrophysiological abnormalities. EETs have vasodilator and natriuretic effect. Blockade of EET formation is associated with salt-sensitive hypertension. Four regioisomeric cis-EET are primary products of arachidonic acid metabolism by cytochrome P450 epoxygenases. Upon hydration by soluble epoxide hydrolase (sEH), EET are metabolized to dihydroxyeicosatrienoic acids (DHET). These hydration products are more stable and less biologically active than EETs. (PMID: 17494091 , 17468203 , 17434916 , 17406062 , 17361113 , 15581597 ).
Structure
Thumb
Synonyms
  1. (+/-)14,15-EpETrE
  2. (5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoate
  3. (5Z,8Z,11Z)-14,15-Epoxyeicosa-5.8.11-trienoic acid
  4. (5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoate
  5. (5Z,8Z,11Z)-14,15-Epoxyicosa-5.8.11-trienoic acid
  6. 14(15)-EpETrE
  7. 14(15)-EpETrE-EA
  8. 14,15-EET
  9. 14,15-EpETrE
  10. 14,15-Epoxy-5Z,8Z,11Z-eicosatrienoate
  11. 14,15-Epoxy-5Z,8Z,11Z-eicosatrienoic acid
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid
Traditional IUPAC Name(5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoic acid
CAS Registry Number81276-03-1
SMILES
CCCCCC1OC1C\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-
InChI KeyJBSCUHKPLGKXKH-ILYOTBPNSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassHeterocyclic Fatty Acids
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Carboxylic Acid
  • Dialkyl Ether
  • Oxirane
Direct ParentEpoxy Fatty Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility3.190E-04 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 area49.83ChemAxon
rotatable bond count14ChemAxon
refractivity98.36ChemAxon
polarizability38.48ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075map00590
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.000134 +/- 0.000053 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.00175 +/- 4.3E-5 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.000135 +/- 0.00006 uMAdult (>18 years old)BothCommentNormal
  • John W. Newm...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023356
KNApSAcK IDNot Available
Chemspider ID4446326
KEGG Compound IDC14771
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04264
Metagene LinkHMDB04264
METLIN IDNot Available
PubChem Compound5283205
PDB IDNot Available
ChEBI ID34157
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Gene Name:
CYP2C18
Uniprot ID:
P33260
Gene Name:
CYP2F1
Uniprot ID:
P24903
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Gene Name:
CYP2B6
Uniprot ID:
P20813
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Gene Name:
CYP3A7
Uniprot ID:
P24462
Gene Name:
CYP4B1
Uniprot ID:
P13584
Gene Name:
CYP4Z1
Uniprot ID:
Q86W10
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
CYP19A1
Uniprot ID:
P11511
Gene Name:
CYP2C8
Uniprot ID:
P10632
Gene Name:
CYP2S1
Uniprot ID:
Q96SQ9
Gene Name:
CYP2J2
Uniprot ID:
P51589
Gene Name:
CYP2A7
Uniprot ID:
P20853
Gene Name:
CYP2A6
Uniprot ID:
P11509
Gene Name:
EPHX2
Uniprot ID:
P34913
Reactions
14,15-Epoxy-5,8,11-eicosatrienoic acid + Water unknown 14,15-DiHETrEdetails
Gene Name:
CYP2D6
Uniprot ID:
Q6NWU0