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Structure Database (LMSD)

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Common Name

PGE2-EA

Systematic Name

N-(11R,15S-dihydroxy-9-oxo-5Z,13E-prostadienoyl)-ethanolamine

Synonyms

Prostaglandin E2-EA
Prostamide-E2
PME2

LM ID

LMFA03010151

Formula

C₂₂H₃₇NO₅

Exact Mass

Calculate m/z

395.267174

Sum Composition

NAE 20:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Prostaglandin E2 ethanolamide (PGE2-EA) is an analog of PGE2 with improved water solubility and stability. PGE2-EA is formed via COX-2 metabolism of arachidonoyl ethanolamide (AEA) and acts as an agonist at E prostanoid (EP) receptors 1-4 (Kis = 2.45, 0.46, 0.2, and 0.51 μM, respectively).^1,2 It also inhibits indoleamine 2,3-dioxygenase-1 (IDO-1) in THP-1 cells and human monocytes (IC50s = 5.7 and 4.7 μM, respectively).³ PGE2-EA (10 μM) prevents morphological changes and F-actin rearrangement as well as reduces L-homocysteine-induced NLRP3 inflammasome formation and activation in podocytes.⁴ Ex vivo, PGE2-EA reduces luminal damage and lymphocyte infiltration in a human mucosal explant colitis model.⁵

This information has been provided by Cayman Chemical

References

1. Liu, T., Li, R., Pan, T., et al. Intercellular transfer of the cellular prion protein. The Journal of Biological Chemisty 27(49), 47671-47678 (2002).

2. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. The Journal of Biological Chemisty 277(47), 44877-44885 (2002).

3. Costabile, M., Bassal, N.K., Gerber, J.P., et al. Inhibition of indoleamine 2,3-dioxygenase activity by fatty acids and prostaglandins: A structure function analysis. Prostaglandins Leukot. Essent. Fatty Acids 122, 7-15 (2017).

4. Li, G., Xia, M., Abais, J.M., et al. Protective action of anandamide and Its COX-2 metabolite against l-homocysteine-induced NLRP3 inflammasome activation and injury in podocytes. J. Pharmacol. Exp. Ther. 358(1), 61-70 (2016).

5. Nicotra, L.L., vu, M.D., Harvey, B.S., et al. Prostaglandin ethanolamides attenuate damage in a human explant colitis model. Prostaglandins Other Lipid Mediat. 100-101, 22-29 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2.,
J Biol Chem, 1997

Pubmed ID: 9261124

String Representations

InChiKey (Click to copy)

GKKWUSPPIQURFM-IGDGGSTLSA-N

InChi (Click to copy)

InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-19,21,24-25,27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,21+/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)NCCO