LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG SVG

Common Name

15R-PGD2

Systematic Name

9S,15R-dihydroxy-11-oxo-5Z,13E-prostadienoic acid

Synonyms

15R-Prostaglandin D2

LM ID

LMFA03010102

Formula

C₂₀H₃₂O₅

Exact Mass

Calculate m/z

352.224976

Sum Composition

FA 20:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Many of the effects of prostaglandin D2 (PGD2) are transduced via a traditional 7-transmembrane GPCR, the DP1 receptor.¹ However, in certain leukocytes and other immune cells, a second PGD2 receptor referred to as the CRTH2 or DP2 receptor has been cloned and characterized.^2,3 15(R)-15-methyl PGD2 is a surprisingly potent agonist at the DP2 receptor, being about 5 times more potent than PGD2 itself.⁴ 15(R)-PGD2 has the potential to be produced endogenously as a natural ligand for DP2, unlike the synthetic 15-methyl analogs. In preliminary reports, 15(R)-PGD2 has also been reported to be a potent and selective DP2 receptor agonist.^5,6

This information has been provided by Cayman Chemical

References

2. Abe, H., Takeshita, T., Nagata, K., et al. Molecular cloning, chromosome mapping and characterization of the mouse CRTH2 gene, a putative member of the leukocyte chemoattractant receptor family. Gene 227(1), 71-77 (1999).

3. Hirai, H., Tanaka, K., Yoshie, O., et al. Prostaglandin D2 selectivity induces chemotaxis in T helper type 2 cells, eosinophils, and basophils via seven-transmembrane receptor CRTH2. J. Exp. Med. 193(2), 255-261 (2001).

5. Kim, S., Bellone, S., Maxey, K.M., et al. Synthesis of 15R-PGD2: A potential DP2 receptor agonist. Bioorg. Med. Chem. Lett. 15(7), 1873-1876 (2005).

4. Monneret, G., Cossette, C., Gravel, S., et al. 15R-methyl-prostaglandin D2 is a potent and selective CRTH2/DP2 receptor agonist in human eosinophils. J. Pharmacol. Exp. Ther. 304(1), 349-355 (2003).

6. Cossette, C., Walsh, S.E., Kim, S., et al. Agonist and antagonist effects of 15R-prostaglandin (PF) D2 and 11-methylene-PGD2 on human eosinophils and basophils. J. Pharmacol. Exp. Ther. 320(1), 173-179 (2007).

1. Boie, Y., Sawyer, N., Slipetz, D.M., et al. Molecular cloning and characterization of the human prostanoid DP receptor. The Journal of Biological Chemisty 270(32), 18910-18916 (1995).

String Representations

InChiKey (Click to copy)

BHMBVRSPMRCCGG-DFVNJMEGSA-N

InChi (Click to copy)

InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17-,18+/m1/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)O