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Structure Database (LMSD)

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Common Name

11beta-PGF2alpha-EA

Systematic Name

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

Synonyms

11beta-PGF2alpha-ethanolamine

LM ID

LMFA03010208

Formula

C₂₂H₃₉NO₅

Exact Mass

Calculate m/z

397.282824

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

11β-Prostaglandin F2α ethanolamide (11β-PGF2α-EA) is the theoretical hepatic metabolite of PGD2-EA, produced during COX-2 metabolism of the endogenous cannabinoid AEA which is found in brain, liver, and other mammalian tissues.¹ AEA can be used directly by COX-2 and specific PG synthase to produce ethanolamide congeners of the classical PGs.^2,3 PGD2-EA is formed in activated RAW 264.7 cells treated with AEA.³

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. 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).

String Representations

InChiKey (Click to copy)

XCVCLIRZZCGEMU-WMTHMIERSA-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