Structure Database (LMSD)
Common Name
11S,12R-EpETrE
Systematic Name
11S,12R-epoxy-5Z,8Z,14Z-eicosatrienoic acid
Synonyms
- 11S,12R-EET
3D model of 11S,12R-EpETrE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
(±)11(12)-EET is a fully racemic version of the R/S enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes.1,2,3 A higher proportion of 11R(12S)-EET is produced by the CYP450 isoforms CYP2C23 and CYP2C24 while CYP2B2 produces a higher proportion of 11S(12R)-EET 11(S),12(R)-EET.3 11(12)-EET has been shown, along with 8(9)-EET , to play a role in the recovery of depleted calcium pools in cultured smooth muscle cells.4 It also inhibits basolateral 18-pS potassium channels in the renal cortical collecting duct when used at a concentration of 100 nM.5 11(12)-EET (50 µg/kg per day) increases adhesion of isolated peripheral blood leukocytes in a chamber coated with P-selectin and ICAM-1 but does not affect choroidal neovascularization size following laser photocoagulation.6 It also has anti-inflammatory, angiogenic, and cardioprotective properties.7
This information has been provided by Cayman Chemical
References
1. Spector, A.A. Arachidonic acid cytochrome P450 epoxygenase pathway. J. Lipid Res. 50(Suppl), S52-S56 (2009).
3. Wang, Z., Wei, Y., Falck, J.R., et al. Arachidonic acid inhibits basolateral K channels in the cortical collecting duct via cytochrome P-450 epoxygenase-dependent metabolic pathways. Am. J. Physiol. Renal Physiol. 294(6), F1441-F1447 (2008).
4. Capdevila, J.H., Falck, J.R., and Harris, R.C. Cytochrome P450 and arachidonic acid bioactivation: Molecular and functional properties of the arachidonate monooxygenase. J. Lipid Res. 41(2), 163-181 (2000).
5. Graber, M.N., Alfonso, A., and Gill, D.L. Recovery of Ca2+ pools and growth in Ca2+ pool-depleted cells is mediated by specific epoxyeicosatrienoic acids derived from arachidonic acid. J. Biol. Chem. 272(47), 29546-29553 (1997).
6. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. J. Biol. Chem. 257(7), 3771-3781 (1982).
String Representations
InChiKey (Click to copy)
DXOYQVHGIODESM-LZXKBWHHSA-N
InChi (Click to copy)
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-/t18-,19+/m1/s1
SMILES (Click to copy)
C(/C=C\C/C=C\CCCC(=O)O)[C@@H]1O[C@@H]1C/C=C\CCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
1
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
358.01
Topological Polar Surface Area
49.83
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
3
logP
6.00
Molar Refractivity
96.58
Admin
Created at
-
Updated at
-