Structure Database (LMSD)

Common Name
5S,6R-EpETrE
Systematic Name
5S,6R-epoxy-8Z,11Z,14Z-eicosatrienoic acid
Synonyms
  • 5S,6R-EET
LM ID
LMFA03080017
Formula
C20H32O3
Exact Mass
Calculate m/z
320.235145
Sum Composition
FA 20:4;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Epoxyeicosatrienoic acids [FA0308]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Epoxy fatty acids [FA0107]

Biological Context

5(6)-EET is a fully racemic version of the enantiomeric forms biosynthesized from arachidonic acid by cytochrome P450 enzymes.1,2 In solution, 5(6)-EET degrades into 5,6-DiHET and 5(6)-δ-lactone, which can be converted to 5(6)-DiHET and quantified by GC-MS.3 In neuroendocrine cells, such as the anterior pituitary and pancreatic islets, 5(6)-EET has been implicated in the mobilization of calcium and hormone secretion.4,5 5(6)-EET is an inhibitor of T-type voltage-gated calcium channels (Cav3) that inhibits isoforms Cav3.1, Cav3.2 (IC50 = 0.54 µM), and Cav3.3 and decreases nifedipine-resistant phenylephrine-induced vasoconstriction in isolated mouse mesenteric arteries via Cav3.2 blockade when used at a concentration of 3 µM.6 In addition, it is a substrate of COX-1 and COX-2, as measured by oxygen consumption and product formation assays when used at a concentration of 50 µM.7 (±)5(6)-EET is provided as a mixture of the free acid and lactone.

This information has been provided by Cayman Chemical

References

1. Falck, J.R., Manna, S., Moltz, J., et al. Epoxyeicosatrienoic acids stimulate glucagon and insulin release from isolated rat pancreatic islets. Biochem. Biophys. Res. Commun. 114(2), 743-749 (1983).
2. Snyder, C., Lattanzio, F., Yadagiri, P., et al. 5,6-Epoxyeicosatrienoic acid mobilizes Ca2+ in anterior pituitary cells. Biochem. Biophys. Res. Commun. 139(3), 1188-1194 (1986).
3. Chacos, N., Falck, J.R., Wixtrom, C., et al. Novel epoxides formed during the liver cytochrome P-450 oxidation of arachidonic acid. Biochem. Biophys. Res. Commun. 104(3), 916-922 (1982).
4. Oliw, E.H., Guengerich, F.P., and Oates, J.A. Oxygenation of arachidonic acid by hepatic monooxygenases. Isolation and metabolism of four epoxide intermediates. The Journal of Biological Chemisty 257(7), 3771-3781 (1982).
5. Rand, A.A., Barnych, B., Morisseau, C., et al. Cyclooxygenase-derived proangiogenic metabolites of epoxyeicosatrienoic acids. Proc. Natl. Acad. Sci. USA 114(17), 4370-4375 (2017).
6. Rashid, M., Manivet, P., Nishio, H., et al. Identification of the binding sites and selectivity of sarpogrelate, a novel 5-HT2 antagonist, to human 5-HT2A, 5-HT2B and 5-HT2C receptor subtypes by molecular modeling. Life Sci. 73(2), 193-207 (2003).
7. Cazade, M., Bidaud, I., Hansen, P.B., et al. 5,6-EET potently inhibits T-type calcium channels: Implication in the regulation of the vascular tone. Pflugers Arch. 466(9), 1759-1768 (2014).

String Representations

InChiKey (Click to copy)
VBQNSZQZRAGRIX-GSKBNKFLSA-N
InChi (Click to copy)
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-/t18-,19+/m1/s1
SMILES (Click to copy)
C(/C=C\C[C@H]1O[C@H]1CCCC(=O)O)/C=C\C/C=C\CCCCC

Other Databases

CHEBI ID
165260
PubChem CID
40490652
Cayman ID
50211

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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