LIPID MAPS

Structure Database (LMSD)

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Common Name

15-deoxy-delta-12,14-PGJ2-d4

Systematic Name

11-oxo-prosta-5Z,9,12E,14E-tetraen-1-oic-3,3,4,4-d4 acid

Synonyms

15-deoxy-delta-12,14-Prostaglandin J2-d4
15-deoxy-PGJ2-d4

LM ID

LMFA03010250

Formula

C₂₀H₂₄D₄O₃

Exact Mass

Calculate m/z

320.228952

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

15-deoxy-Δ12,14-PGJ2-d4 contains four deuterium atoms at the 3, 3', 4, and 4' positions. It is intended for use as an internal standard for the quantification of 15-deoxy-Δ12,14-PGJ2 by GC- or LC-mass spectrometry. 15-deoxy-Δ12,14-Prostaglandin J2 (15-deoxy-Δ12,14-PGJ2) is a metabolite of PGJ2. 15-deoxy-Δ12,14-PGJ2 is formed from PGD2 by the elimination of two molecules of water. It binds selectively to PPARγ with an EC50 of 2 µM in a murine chimera system.^1,2 15-deoxy-Δ12,14-PGJ2 is more potent than PGD2, Δ12-PGJ2, and PGJ2 in stimulating lipogenesis in C3H10T1/2 cells. The EC50 for induction of adipocyte differentiation in cultured fibroblasts is 7 µM.¹

This information has been provided by Cayman Chemical

References

1. 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).

2. 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).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

VHRUMKCAEVRUBK-NSTSLKHFSA-N

InChi (Click to copy)

InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1/i8D2,11D2

SMILES (Click to copy)

C1(=C/C=C/CCCCC)\C(=O)C=C[C@@H]\1C/C=C\C([2H])([2H])C([2H])([2H])CC(=O)O