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Structure Database (LMSD)

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Common Name

PGE2-dihydroxypropanylamine

Systematic Name

N-(1,3-dihydroxypropan-2-yl)-9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoyl amine

Synonyms

Prostaglandin E2-dihydroxypropanylamine
Prostaglandin E2 serinol amide
PGE2-SA

LM ID

LMFA03010192

Formula

C₂₃H₃₉NO₆

Exact Mass

Calculate m/z

425.277739

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

2-Arachidonyl glycerol (2-AG) exhibits cannabinoid agonist activity at the CB1 receptor, is an important endogenous monoglyceride species, and is thus considered to be the natural ligand for the CB1 receptor.^1,2 2-AG can also be metabolized sequentially by COX-2 and specific prostaglandin (PG) synthases to form PG 2-glyceryl esters.³ PGE2-SA is a stable analog of PGE2 2-glyceryl ester. The biological activity of PGE2-SA has not yet been determined.

This information has been provided by Cayman Chemical

References

1. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J. Biochem. 122(4), 890-895 (1997).

2. Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett. 429(2), 152-156 (1998).

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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Structural determinants for calcium mobilization by prostaglandin E2 and prostaglandin F2alpha glyceryl esters in RAW 264.7 cells and H1819 cells.,
Prostaglandins Other Lipid Mediat, 2010

Pubmed ID: 20152925

String Representations

InChiKey (Click to copy)

QJOORAQHWWTUIP-HIGMCGMBSA-N

InChi (Click to copy)

InChI=1S/C23H39NO6/c1-2-3-6-9-18(27)12-13-20-19(21(28)14-22(20)29)10-7-4-5-8-11-23(30)24-17(15-25)16-26/h4,7,12-13,17-20,22,25-27,29H,2-3,5-6,8-11,14-16H2,1H3,(H,24,30)/b7-4-,13-12+/t18-,19+,20+,22+/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)NC(CO)CO