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Structure Database (LMSD)

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Common Name

PGD2-EA

Systematic Name

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

Synonyms

Prostaglandin D2-EA
Prostamide-D2
PMD2

LM ID

LMFA03010152

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

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Classification

Biological Context

Prostaglandin D2 ethanolamide (PGD2-EA) is a bioactive lipid produced by the sequential metabolism of anandamide (arachidonoyl ethanolamide) by cyclooxygenase (COX) enzymes, in particular by COX-2, and PGD synthase.^1,2,3 The biosynthesis of PGD2-EA from anandamide can also be increased when anandamide metabolism is diminished by deletion of fatty acid amide hydrolase.⁴ PGD2-EA is inactive against recombinant prostanoid receptors, including the D prostanoid receptor.⁵ It increases the frequency of miniature inhibitory postsynaptic currents in primary cultured hippocampal neurons, an effect which is the opposite of that induced by anandamide.3. PGD2-EA also induces apoptosis in colorectal carcinoma cell lines.²

This information has been provided by Cayman Chemical

References

1. Sang, N., Zhang, J., and Chen, C. PGE2 glycerol ester, a COX-2 oxidative metabolite of 2-arachidonoyl glycerol, modulates inhibitory synaptic transmission in mouse hippocampal neurons. J. Physiol. 572(Pt 3), 735-745 (2006).

2. Patsos, H.A., Hicks, D.J., Dobson, R.R.H., et al. The endogenous cannabinoid, anandamide, induces cell death in colorectal carcinoma cells: A possible role for cyclooxygenase 2. Gut 54(12), 1741-1750 (2005).

3. Matias, I., Chen, J., De Petrocellis, L., et al. Prostaglandin ethanolamides (prostamides): In vitro pharmacology and metabolism. J. Pharmacol. Exp. Ther. 309(2), 745-757 (2004).

4. Weber, A., Ni, J., Ling, K.H.J., et al. Formation of prostamides from anandamide in FAAH knockout mice analyzed by HPLC with tandem mass spectrometry. J. Lipid. Res. 45(4), 757-763 (2004).

5. 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. J. Biol. Chem. 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)

KEYDJKSQFDUAGF-YIRKRNQHSA-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/h4,7,12-13,17-20,24-26H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,20-/m0/s1

SMILES (Click to copy)

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