LIPID MAPS

Structure Database (LMSD)

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Common Name

15-deoxy-delta-12,14-PGA2

Systematic Name

9-oxo-5Z,10,12Z,14E-prostatetraenoic acid

Synonyms

15d-Prostaglandin A2
15d-PGA2
15-deoxy-PGA2

LM ID

LMFA03010172

Formula

C₂₀H₂₈O₃

Exact Mass

Calculate m/z

316.203845

Sum Composition

FA 20:6;O

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

15-deoxy-Δ12,14-PGA2 is a synthetic analog of PGA2. It shares common structural features with 15-deoxy-Δ12,14-PGJ2, which is a ligand for PPARγ.^1,2 Antimitotic and antitumor activity have been reported for a similar analog,3 but there are no published reports on the biological activity of 15-deoxy-Δ12,14-PGA2 at this time.

This information has been provided by Cayman Chemical

References

1. Kato, T., Fukushima, M., Kurozumi, S., et al. Antitumor activity of Δ7-prostaglandin A1 and Δ12-prostaglandin J2 in vitro and in vivo. Cancer Res. 46(7), 3538-3542 (1986).

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. Kliewer, S.A., Lenhard, J.M., Willson, T.M., et al. A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor γ and promotes adipocyte differentiation. Cell 83(5), 813-819 (1995).

String Representations

InChiKey (Click to copy)

BHHHGDAJJMEHST-NBIYZLHXSA-N

InChi (Click to copy)

InChI=1S/C20H28O3/c1-2-3-4-5-6-9-12-17-15-16-19(21)18(17)13-10-7-8-11-14-20(22)23/h6-7,9-10,12,15-16,18H,2-5,8,11,13-14H2,1H3,(H,22,23)/b9-6+,10-7-,17-12-/t18-/m1/s1

SMILES (Click to copy)

C(CCC/C=C\C[C@@H]1/C(=C\C=C\CCCCC)/C=CC1=O)(=O)O