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Structure Database (LMSD)

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Common Name

PGF2alpha-EA

Systematic Name

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

Synonyms

Prostaglandin F2alpha-EA
Prostamide-F2alpha
PMF2alpha

LM ID

LMFA03010075

Formula

C₂₂H₃₉NO₅

Exact Mass

Calculate m/z

397.282824

Sum Composition

NAE 20:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Prostaglandin F2α ethanolamide (PGF2α-EA) is produced by COX-2 metabolism of the endogenous cannabinoid, arachidonoyl ethanolamide (AEA), found in brain, liver, and other mammalian tissues.¹ AEA can be metabolized directly by the sequential action of COX-2 and specific PG synthases to produce ethanolamide congeners of the classical PGs.^2,3 PGF2α-EA has also been reported to be biosynthesized by this mechanism when AEA was infused into the lung and liver of living mice. PGF2α-EA is a potent dilator (EC50 = 58 nM) of the cat iris sphincter, which is a model system for testing potential intraocular hypotensive agents.⁴

This information has been provided by Cayman Chemical

References

1. Bachur, N.R., Masek, K., Melmon, K.L., et al. Fatty acid amides of ethanolamine in mammalian tissues. The Journal of Biological Chemisty 240, 1019-1024 (1965).

2. Yu, M., Ives, D., and Ramesha, C.S. Synthesis of prostaglandin E2 ethanolamide from anandamide by cyclooxygenase-2. The Journal of Biological Chemisty 272(34), 21181-21186 (1997).

3. Woodward, D.F., Tang-Liu, D.D.S., Madhu, C., et al. Prostaglandin F2α (PGF2α) 1-ethanolamide: A pharmacologically unique local hormone biosynthesized from anandamide. 11th International conference on advances in prostaglandin and leukotriene research: Basic science and new clinical applications 27 (2000).

4. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides.,
J Biol Chem, 2002

Pubmed ID: 12244105

String Representations

InChiKey (Click to copy)

XCVCLIRZZCGEMU-WLOFLUCMSA-N

InChi (Click to copy)

InChI=1S/C22H39NO5/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/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,20-,21+/m0/s1

SMILES (Click to copy)

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