LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

8-iso-PGF2beta

Systematic Name

9R,11R,15S-trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R]

Synonyms

LM ID

LMFA03110006

Formula

C₂₀H₃₄O₅

Exact Mass

Calculate m/z

354.240625

Sum Composition

FA 20:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

8-iso Prostaglandin F2β (8-iso PGF2β) is an isomer of PGF2α with a non-enzymatic, non-cyclooxygenase origin. It is one of 64 possible isomers of PGF2α which can be produced by free radical peroxidation of arachidonic acid. 8-iso PGF2β exhibits very weak contraction of human umbilical vein artery and does not promote aggregation of human whole blood.^1,2 However, 8-iso PGF2β moderately contracts both the canine and porcine pulmonary vein, although the effect is much weaker than that exhibited by other isoprostanes such as 8-iso PGE1, 8-iso PGE2, or 8-iso PGF2α3,4

This information has been provided by Cayman Chemical

References

1. Janssen, L.J., and Tazzeo, T. Involvement of TP and EP3 receptors in vasoconstrictor responses to isoprostanes in pulmonary vasculature. J. Pharmacol. Exp. Ther. 301(3), 1060-1066 (2002).

2. Cranshaw, J.H., Evans, T.W., and Mitchell, J.A. Charcterization of the effects of isoprostanes on platelet aggregation in human whole blood. Br. J. Pharmacol. 132(8), 1699-1706 (2001).

3. Janssen, L.J., Premji, M., Netherton, S., et al. Vasoconstrictor actions of isoprostanes via tyrosine kinase and Rho kinase in human and canine pulmonary vascular smooth muscles. Br. J. Pharmacol. 132(1), 127-134 (2001).

4. Oliveira, L., Stallwood, N.A., and Crankshaw, D.J. Effects of some isoprostanes on the human umbilical artery in vitro. Br. J. Pharmacol. 129(3), 509-514 (2000).

String Representations

InChiKey (Click to copy)

PXGPLTODNUVGFL-HMALSPAFSA-N

InChi (Click to copy)

InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17+,18+,19+/m0/s1

SMILES (Click to copy)

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