LIPID MAPS

Structure Database (LMSD)

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Common Name

PGE1-EA

Systematic Name

N-(9-oxo-11R,15S-dihydroxy-13E-prostenoyl)-ethanolamine

Synonyms

PGE1-ethanolamine

LM ID

LMFA03010209

Formula

C₂₂H₃₉NO₅

Exact Mass

Calculate m/z

397.282824

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Biological Context

Prostaglandin E1 ethanolamide (PGE1-EA) is the ethanolamine-amide analog of PGE1. Conversion of AEA, the ethanolamide of arachidonic acid, to PGE2-EA has been demonstrated in vitro.^1,2 It is not established whether this conversion occurs in whole animals, nor has the pharmacology of the resultant prostaglandin ethanolamides been rigorously studied.

This information has been provided by Cayman Chemical

References

1. 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).

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).

String Representations

InChiKey (Click to copy)

HLQFDRCTTQBTCE-RCDOCOITSA-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/h12-13,17-19,21,24-25,27H,2-11,14-16H2,1H3,(H,23,28)/b13-12+/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]1CCCCCCC(=O)NCCO