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Structure Database (LMSD)

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Common Name

20-hydroxy-PGE2

Systematic Name

9-oxo-11R,15S,20-trihydroxy-5Z,13E-prostadienoic acid

Synonyms

20-hydroxy-Prostaglandin E2

LM ID

LMFA03010014

Formula

C₂₀H₃₂O₆

Exact Mass

Calculate m/z

368.21989

Sum Composition

FA 20:4;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

20-hydroxy Prostaglandin E2 (PGE2) is a metabolite of 20-HETE and PGE2 .^1,2 It inhibits IFN-γ-induced kynurenine production in THP-1 cells and primary human monocytes (IC50s = 7.4 and 11.2 µM, respectively).³ 20-hydroxy PGE2 (1 µM) induces lipid accumulation and lipid droplet formation in primary human mesenchymal stem cell-derived adipocytes.⁴ Intra-arterial infusion of 20-hydroxy PGE2 increases cortical and medullary blood flow in rat kidneys.⁵ Serum levels of 20-hydroxy PGE2 are decreased in patients with rheumatoid arthritis.⁶

This information has been provided by Cayman Chemical

References

1. Rodríguez-Carrio, J., Coras, R., Alperi-López, M., et al. Profiling of serum oxylipins during the earliest stages of rheumatoid arthritis. Arthritis Rheumatol. 73(3), 401-413 (2021).

2. Oyekan, A.O. Differential effects of 20-hydroxyeicosatetraenoic acid on intrarenal blood flow in the rat. J Pharmacol Exp Ther. 313(3), 1289-1295 (2005).

3. Kim, D.H., Puri, N., Sodhi, K., et al. Cyclooxygenase-2 dependent metabolism of 20-HETE increases adiposity and adipocyte enlargement in mesenchymal stem cell-derived adipocytes. J. Lipid Res. 54(3), 786-793 (2013).

4. Costabile, M., Bassal, N.K., Gerber, J.P., et al. Inhibition of indoleamine 2,3-dioxygenase activity by fatty acids and prostaglandins: A structure function analysis. Prostaglandins Leukot. Essent. Fatty Acids 122, 7-15 (2017).

5. McGiff, J.C., and Quilley, J. 20-HETE and the kidney: Resolution of old problems and new beginnings. Am. J. Physiol. 277(3), R607-R623 (1999).

6. Oliw, E.H., Fahlstadius, P., and Hamberg, M. Isolation and biosynthesis of 20-hydroxyprostaglandins E1 and E2 in ram seminal fluid. J. Biol. Chem. 261, 9216-9221 (1986).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Ovis aries (#9940)

Mammalia (#40674)

Isolation and biosynthesis of 20-hydroxyprostaglandins E1 and E2 in ram seminal fluid.,
J Biol Chem, 1986

Pubmed ID: 3087990

String Representations

InChiKey (Click to copy)

AZIGEYVZEVXWAD-NZGURKHLSA-N

InChi (Click to copy)

InChI=1S/C20H32O6/c21-13-7-3-4-8-15(22)11-12-17-16(18(23)14-19(17)24)9-5-1-2-6-10-20(25)26/h1,5,11-12,15-17,19,21-22,24H,2-4,6-10,13-14H2,(H,25,26)/b5-1-,12-11+/t15-,16+,17+,19+/m0/s1

SMILES (Click to copy)

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