LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

15-deoxy-delta-12,14-PGD2

Systematic Name

9S-hydroxy-11-oxo-5Z,12E,14E-prostatrienoic acid

Synonyms

15-deoxy-delta-12,14-Prostaglandin D2
15-deoxy-PGD2

LM ID

LMFA03010051

Formula

C₂₀H₃₀O₄

Exact Mass

Calculate m/z

334.21441

Sum Composition

FA 20:5;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15-deoxy-Δ12,14-PGD2 is a metabolite of PGD2 .¹ It is an agonist of PGD2 receptor 2 (DP2) that binds DP2 (Ki = 50 nM for the mouse receptor expressed in HEK293 cell membranes) and induces activation of eosinophils (EC50 = 8 nM).^2,3 It also stimulates the recruitment of steroid receptor coactivator-1 (SRC-1) to peroxisome proliferator-activated receptor γ (PPARγ) and induces PPARγ-mediated transcription in a reporter assay when used at a concentration of 5 µM.¹ 15-deoxy-Δ12,14-PGD2 is cytotoxic to L1210 murine leukemia cells (IC50 = 0.3 µg/ml).⁴ It inhibits ADP-induced platelet aggregation (IC50 = 320 ng/ml) less potently than PGD2.5

This information has been provided by Cayman Chemical

References

1. Bundy, G.L., Morton, D.R., Peterson, D.C., et al. Synthesis and platelet aggregation inhibiting activity of prostaglandin D analogues. J. Med. Chem. 26(6), 790-799 (1983).

2. Forman, B.M., Tontonoz, P., Chen, J., et al. 15-Deoxy-Δ12,14-prostaglandin J2 is a ligand for the adipocyte determination factor PPARγ. Cell 83(5), 803-812 (1995).

3. Monneret, G., Li, H., Vasilescu, J., et al. 15-Deoxy-Δ12,14-prostaglandins D2 and J2 are potent activators of human eosinophils. J. Immunol. 168(7), 3563-3569 (2002).

4. Hata, A.N., Zent, R., Breyer, M.D., et al. Expression and molecular pharmacology of the mouse CRTH2 receptor. J. Pharmacol. Exp. Ther. 306(2), 463-470 (2003).

5. Söderström, M., Wigren, J., Surapureddi, S., et al. Novel prostaglandin D2-derived activators of peroxisome proliferator-activated receptor-γ are formed in macrophage cell cultures. Biochim. Biophys. Acta 1631(1), 35-41 (2003).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

QUGBPWLPAUHDTI-PLGLXCLHSA-N

InChi (Click to copy)

InChI=1S/C20H30O4/c1-2-3-4-5-6-9-12-16-17(19(22)15-18(16)21)13-10-7-8-11-14-20(23)24/h6-7,9-10,12,17,19,22H,2-5,8,11,13-15H2,1H3,(H,23,24)/b9-6+,10-7-,16-12+/t17-,19+/m1/s1

SMILES (Click to copy)

C1(=C/C=C/CCCCC)\C(=O)C[C@H](O)[C@@H]\1C/C=C\CCCC(=O)O