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Structure Database (LMSD)

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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

352.224975

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

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).

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).

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).

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).

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).

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