| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-16 07:20:23 -0600 |
| Update Date |
2013-05-29 13:45:54 -0600 |
| HMDB ID |
HMDB10409 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
11,12-EpETrE |
| Description |
11,12-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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (+/-)11(12)-EET
- (+/-)11(12)-EpETrE
- (+/-)11,12-EpETrE
- (5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoate
- (5Z,8Z,14Z)-11,12-Epoxyeicosa-5,8,14-trienoic acid
- (5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoate
- (5Z,8Z,14Z)-11,12-Epoxyicosa-5,8,14-trienoic acid
- 11,12-Eet
- 11,12-Epoxy-5Z,8Z,14Z-eicosatrienoate
- 11,12-Epoxy-5Z,8Z,14Z-eicosatrienoic acid
|
| Chemical Formula |
C20H32O3 |
| Average Molecular Weight |
320.4663 |
| Monoisotopic Molecular Weight |
320.23514489 |
| IUPAC Name |
(5E,8Z)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid |
| Traditional IUPAC Name |
(5E,8Z)-10-{3-[(2E)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid |
| CAS Registry Number |
Not 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 Key |
DXOYQVHGIODESM-IQCOFVSKSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Eicosanoids |
| Sub Class |
Hepoxilins |
| Other Descriptors |
- Aliphatic Heteromonocyclic Compounds
- Epoxy Fatty Acids
- Organic Compounds
- Unsaturated Fatty Acids
|
| Substituents |
- Carboxylic Acid
- Dialkyl Ether
- Oxirane
|
| Direct Parent |
Hepoxilins |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
- Signaling
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.000303+/- 0.000023 uM |
Adult (>18 years old) |
Not Specified |
Normal
|
|
| Blood |
Detected and Quantified |
|
0.303 +/- 0.028 uM |
Adult (>18 years old) |
Not Specified |
Normal
|
|
| Blood |
Detected and Quantified |
|
1.02 +/- 1.4 uM |
Adult (>18 years old) |
Not Specified |
Normal
|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.00001 +/- 0.00002 uM |
Adult (>18 years old) |
Both |
Normal
|
|
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB027560 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
Not Available |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB10409 |
| Metagene Link |
HMDB10409 |
| METLIN ID |
Not Available |
| PubChem Compound |
53480479 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- 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.
Pubmed: 9368016
|
Normal
