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Structure Database (LMSD)

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Common Name

1(3)-glyceryl-PGE2

Systematic Name

9-oxo-11R,15S-dihydroxy-5Z,13E-prostadienoic acid 1(3)-glyceryl ester

Synonyms

PGE2-G
1(3)-glyceryl-Prostaglandin E2

LM ID

LMFA03010186

Formula

C₂₃H₃₈O₇

Exact Mass

Calculate m/z

426.261755

Sum Composition

FA 23:4;O5

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.^1,2 Incubation of 2-AG with cyclooxygenase-2 and specific prostaglandin H2 (PGH2) isomerases in cell cultures and isolated enzyme preparations results in prostaglandin glycerol ester formation.³ The biosynthesis of PGH, PGD, PGE, PGF, and Thromboxane A-2-glyceryl ester compounds have all been documented. The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 2:1-glyceryl ester mixture in typical aqueous media. While the stability and metabolism of these prostaglandin products has been investigated, little is known about their intrinsic biological activity.⁴

This information has been provided by Cayman Chemical

References

1. Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem. Biophys. Res. Commun. 229(1), 58-64 (1996).

2. 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).

3. Kozak, K.R., Crews, B.C., Ray, J.L., et al. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. The Journal of Biological Chemisty 276(40), 36993-36998 (2001).

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).

String Representations

InChiKey (Click to copy)

RJXVYMMSQBYEHN-LVXZDWGESA-N

InChi (Click to copy)

InChI=1S/C23H38O7/c1-2-3-6-9-17(25)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-16-18(26)15-24/h4,7,12-13,17-20,22,24-26,28H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,18?,19+,20+,22+/m0/s1

SMILES (Click to copy)

OCC([H])(O)COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCCCC