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Structure Database (LMSD)

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Common Name

15-methyl-15R-PGD2

Systematic Name

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

Synonyms

15-methyl-15R-Prostaglandin D2

LM ID

LMFA03010105

Formula

C₂₁H₃₄O₅

Exact Mass

Calculate m/z

366.240626

Sum Composition

FA 21:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15(R)-15-methyl Prostaglandin D2 (15(R)-15-methyl PGD2) is a metabolically stable synthetic analog of PGD2 . The physiological actions of PGD2 include regulation of sleep, lowering of body temperature, inhibition of platelet aggregation and relaxation of vascular smooth muscle.^1,2,3 PGD2 mediates its effects by 2 distinct G-protein-coupled receptors, DP1and CRTH2/DP2.4,5,6 15(R)-15-methyl PGD2 is a potent, selective agonist for the CRTH2/DP2 receptor.⁷ The EC50 values for eosinophil CD11b expression, actin polymerization, and chemotaxis are 1.4, 3.8, and 1.7 nM, respectively, each of which is approximately 3-5 fold lower than those for PGD2. In contrast the EC50 for the DP1-mediated increase in platelet cAMP by 15(R)-15-methyl PGD2 is >10 µM.⁷

This information has been provided by Cayman Chemical

References

3. Onoe, H., Ueno, R., Fujita, I., et al. Prostaglandin D2, a cerebral sleep-inducing substance in monkeys. Proc. Natl. Acad. Sci. USA 85(11), 4082-4086 (1988).

1. Hayaishi, O. Sleep-wake regulation by prostaglandins D2 and E2. The Journal of Biological Chemisty 263(29), 14593-14596 (1988).

2. Giles, H., and Leff, P. The biology and pharmacology of PGD2. Prostaglandins 35(2), 277-300 (1988).

4. 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).

5. 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).

6. Monneret, G., Gravel, S., Diamond, M., et al. Prostaglandin D2 is a potent chemoattractant for human eosinophils that acts via a novel DP receptor. Blood 98(6), 1942-1948 (2001).

7. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

15R-methyl-prostaglandin D2 is a potent and selective CRTH2/DP2 receptor agonist in human eosinophils.,
J Pharmacol Exp Ther, 2003

Pubmed ID: 12490611

String Representations

InChiKey (Click to copy)

CTXLUMAOXBULOZ-BKVRKCTKSA-N

InChi (Click to copy)

InChI=1S/C21H34O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-18,22,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,21-/m1/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@](C)(O)CCCCC)C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O