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Record Information
Version3.6
Creation Date2008-09-16 13:20:23 UTC
Update Date2016-02-11 01:18:52 UTC
HMDB IDHMDB10409
Secondary Accession NumbersNone
Metabolite Identification
Common Name11,12-EpETrE
Description11,12-EpETrE or 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid is an epoxyeicosatrienoic acid or an EET derived from arachadonic acid. EETs function as autacrine and paracrine mediators. During inflammation, a large amount of arachidonic acid (AA) is released into the cellular milieu and cyclooxygenase enzymes convert this AA to prostaglandins that in turn sensitize pain pathways. However, AA is also converted to natural epoxyeicosatrienoic acids (EETs) by cytochrome P450 enzymes. Cytochrome P450 (CYP) epoxygenases convert arachidonic acid to four epoxyeicosatrienoic acid (EET) regioisomers, 5,6-, 8,9-, 11,12-, and 14,15-EET. EETs produce vascular relaxation by activating smooth muscle large-conductance Ca2+-activated K+ channels. In particular, 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid has been show to play a role in the recovery of depleted Ca2+ pools in cultured smooth muscle cells (PMID: 9368016 ). In addition, EETs have antiinflammatory effects on blood vessels and in the kidney, promote angiogenesis, and protect ischemic myocardium and brain. EET levels are typically regulated by soluble epoxide hydrolase (sEH), the major enzyme degrading EETs. Specifically, soluble epoxide hydrolase (sEH) converts EETs to dihydroxyeicosatrienoic acids.
Structure
Thumb
Synonyms
ValueSource
(+/-)11(12)-eetHMDB
(+/-)11(12)-epetreHMDB
(+/-)11,12-epetreHMDB
(5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoateHMDB
(5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoic acidHMDB
(5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoateHMDB
(5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoic acidHMDB
11,12-EetHMDB
11,12-Epoxy-5Z,8Z,14Z-eicosatrienoateHMDB
11,12-Epoxy-5Z,8Z,14Z-eicosatrienoic acidHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5E,8Z)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
Traditional Name(5E,8Z)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C\CC1OC1C\C=C/C\C=C\CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6+,12-9+,13-10-
InChI KeyInChIKey=DXOYQVHGIODESM-IQCOFVSKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHepoxilins
Alternative Parents
Substituents
  • Hepoxilin
  • Medium-chain fatty acid
  • Heterocyclic fatty acid
  • Epoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Signaling
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 Solubility0.000327 mg/mLALOGPS
logP6.25ALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity98.36 m3·mol-1ChemAxon
Polarizability38.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000303+/- 0.000023 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.000303 +/- 0.000028 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00102 +/- 0.0014 uMAdult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00001 +/- 0.00002 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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027560
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10409
Metagene LinkHMDB10409
METLIN IDNot Available
PubChem Compound53480479
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Graber MN, Alfonso A, Gill DL: Recovery of Ca2+ pools and growth in Ca2+ pool-depleted cells is mediated by specific epoxyeicosatrienoic acids derived from arachidonic acid. J Biol Chem. 1997 Nov 21;272(47):29546-53. [9368016 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Molecular weight:
59347.31
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 11,12-EpETrE + NADP + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
Gene Name:
EPHX2
Uniprot ID:
P34913
Molecular weight:
62615.22
Reactions
11,12-EpETrE + Water → 11,12-DiHETrEdetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate and palmitate. Shows no activity towards arachidonic acid and prostaglandin A1. Lacks functional activity in the kidney and does not contribute to renal 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis.
Gene Name:
CYP4A22
Uniprot ID:
Q5TCH4
Molecular weight:
59245.28
Reactions
Arachidonic acid + Oxygen + NADPH + Hydrogen Ion → 11,12-EpETrE + NADP + Waterdetails