LIPID MAPS

Structure Database (LMSD)

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Common Name

1(3)-glyceryl-PGF2alpha

Systematic Name

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

Synonyms

PGF2alpha-G
1(3)-glyceryl-Prostaglandin F2alpha

LM ID

LMFA03010181

Formula

C₂₃H₄₀O₇

Exact Mass

Calculate m/z

428.277406

Sum Composition

FA 23:3;O5

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

2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the central cannabinoid 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 PG glyceryl 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 PGF2α-1-glyceryl ester has been investigated, little is known about its intrinsic biological activity.⁴

This information has been provided by Cayman Chemical

References

1. 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).

2. Kozak, K.R., Crews, B.C., Ray, J.L., et al. Metabolism of prostaglandin glycerol esters and prostaglandin ethanolamides in vitro and in vivo. J. Biol. Chem. 276(40), 36993-36998 (2001).

3. 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).

4. 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).

String Representations

InChiKey (Click to copy)

NWKPOVHSHWJQNI-OMVDPNNKSA-N

InChi (Click to copy)

InChI=1S/C23H40O7/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/h4,7,12-13,17-22,24-28H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,18?,19+,20+,21-,22+/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(OCC([H])(O)CO)=O