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Structure Database (LMSD)

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Common Name

bicyclo-PGE2

Systematic Name

9,15-dioxo-5Z-prostaenoic acid-cyclo[11S,16]

Synonyms

bicyclo-Prostaglandin E2

LM ID

LMFA03010034

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

Bicyclo prostaglandin E2 (Bicyclo PGE2) is a stable breakdown product of PGE2 and 13,14-dihydro-15-keto PGE2 . Bicyclo PGE2 is a stable, base-catalyzed transformation product of 13,14-dihydro-15-keto PGE2. 13,14-dihydro-15-keto PGE2 itself is a metabolite of PGE2 found in human plasma at a median level of 20-25 pg/ml.^1,2 Due to the inherent instability of 13,14-dihydro-15-keto PGE2, it is advisable to quantify it as bicyclo PGE2 to estimate PGE2 biosynthesis or metabolism in vivo.^3,4

This information has been provided by Cayman Chemical

References

1. Leonhardt, A., Krauss, M., Gieler, U., et al. In vivo formation of prostaglandin E1 and prostaglandin E2 in atopic dermatitis. Br. J. Dermatol. 136(3), 337-340 (1997).

2. Murphy, R.C., and Fitzgerald, G.A. Current approaches to estimation of eicosanoid formation in vivo. Adv. Prostaglandin Thromboxane Leukot. Res. 22, 341-348 (1994).

3. Granström, E., Hamberg, M., Hansson, G., et al. Chemical instability of 15-keto-13,14-dihydro-PGE2: The reason for low assay reliability. Prostaglandins 19(6), 933-945 (1980).

4. Hamberg, M., and Samuelsson, B. On the metabolism of prostaglandins E1 and E2 in man. J. Biol. Chem. 246(22), 6713-6721 (1971).

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)

CGCZPIJMGKLVTQ-PAJBVNRRSA-N

InChi (Click to copy)

InChI=1S/C20H30O4/c1-2-3-8-16-17-13-19(22)15(14(17)11-12-18(16)21)9-6-4-5-7-10-20(23)24/h4,6,14-17H,2-3,5,7-13H2,1H3,(H,23,24)/b6-4-/t14-,15-,16?,17+/m1/s1

SMILES (Click to copy)

[C@H]12CC(=O)[C@H](C/C=C\CCCC(=O)O)[C@H]1CCC(=O)C2([H])CCCC