Structure Database (LMSD)

Common Name
11S,12R-EpETrE
Systematic Name
11S,12R-epoxy-5Z,8Z,14Z-eicosatrienoic acid
Synonyms
  • 11S,12R-EET
LM ID
LMFA03080014
Formula
Exact Mass
Calculate m/z
320.235146
Sum Composition
Status
Curated



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

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

CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID

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

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Updated at
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