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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

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).

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).

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