LIPID MAPS

Structure Database (LMSD)

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Common Name

13,14-dihydro-15-keto-PGE2-d4

Systematic Name

9,15-dioxo-11R-hydroxy-5Z-prostenoic 3,3,4,4-d4 acid

Synonyms

13,14-dihydro-15-keto-Prostaglandin E2-d4
9,15-dioxo-11alpha-hydroxy-prost-5Z-en-1-oic-3,3,4,4-d4 acid

LM ID

LMFA03010249

Formula

C₂₀H₂₈D₄O₅

Exact Mass

Calculate m/z

356.250082

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

13,14-dihydro-15-keto Prostaglandin E2-d4 (13,14-dihydro-15-keto PGE2-d4) is intended for use as an internal standard for the quantification of 13,14-dihydro-15-keto PGE2 by GC- or LC-MS. 13,14-dihydro-15-keto PGE2 is a metabolite of PGE2 and the primary PGE2 metabolite in plasma.^1,2 It is formed from PGE2 via a 15-keto PGE2 intermediate by 15-oxo-PG Δ13 reductase.² Unlike PGE2, 13,14-dihydro-15-keto PGE2 does not bind effectively to the PGE2 receptors EP2 and EP4 expressed in CHO cells (Kis = 12 and 57 µM, respectively) or induce adenylate cyclase activity in the same cells (EC50s = >18 and >38 µM, respectively). Levels of 13,14-dihydro-15-keto PGE2 are increased in the plasma of women in the third trimester of pregnancy and in women during and immediately after labor and delivery.³ Levels of 13,14-dihydro-15-keto PGE2 levels are decreased in tumor tissue compared to adjacent non-cancerous tissue isolated from patients with non-small cell lung cancer (NSCLC).⁴

This information has been provided by Cayman Chemical

References

1. Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E1 and E2 in man. The Journal of Biological Chemisty 246(22), 6713-6721 (1971).

2. Nishigaki, N., Negishi, M., and Ichikawa, A. Two Gs-coupled prostaglandin E receptor subtypes, EP2 and EP4, differ in desensitization and sensitivity to the metabolic inactivation of the agonist. Mol. Pharmacol. 50(4), 1031-1037 (1996).

3. Husslein, P., and Sinzinger, H. Concentration of 13,14-dihydro-15-keto-prostaglandin E2 in the maternal peripheral plasma during labour of spontaneous onset. Br. J. Obstet. Gynaecol. 91(3), 228-231 (1984).

4. Hughes, D., Otani, T., Yang, P., et al. NAD+-dependent 15-hydroxyprostaglandin dehydrogenase regulates levels of bioactive lipids in non-small cell lung cancer. Cancer Prev. Res. (Phila.) 1(4), 241-249 (2008).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthetic deuterated standard

String Representations

InChiKey (Click to copy)

CUJMXIQZWPZMNQ-BQWYWOLISA-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/h4,7,16-17,19,23H,2-3,5-6,8-14H2,1H3,(H,24,25)/b7-4-/t16-,17-,19-/m1/s1/i5D2,8D2

SMILES (Click to copy)

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