LIPID MAPS

Structure Database (LMSD)

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Common Name

8-iso-PGE2

Systematic Name

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

Synonyms

LM ID

LMFA03110003

Formula

C₂₀H₃₂O₅

Exact Mass

Calculate m/z

352.224975

Sum Composition

FA 20:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

8-iso Prostaglandin E2 (8-iso PGE2) is one of several isoprostanes produced from arachidonic acid during lipid peroxidation.¹ It is a potent renal vasoconstrictor in the rat.^1,2 8-iso PGE2 inhibits U-46619 or I-BOP-induced platelet aggregation with IC50 values of 0.5 and 5 µM, respectively.³ When infused into the renal artery of the rat at a concentration of 4 µg/kg/min, 8-iso PGE2 decreases the GFR and renal plasma flow by 80% without affecting blood pressure.¹

This information has been provided by Cayman Chemical

References

1. Hoffman, S.W., Moore, S., and Ellis, E.F. Isoprostanes: Free radical-generated prostaglandins with constrictor effects on cerebral arterioles. Stroke 28(4), 844-884 (1997).

2. Morrow, J.D., Minton, T.A., Mukundan, C.R., et al. Free radical-induced generation of isoprostanes in vivo. Evidence for the formation of D-ring and E-ring isoprostanes. J. Biol. Chem. 269(6), 4317-4326 (1994).

3. Longmire, A.W., Roberts, L.J., and Morrow, J.D. Actions of the E2-isoprostane, 8-iso-PGE2, on the platelet thromboxane/endoperoxide receptor in humans and rats: Additional evidence for the existence of a unique isoprostane receptor. Prostaglandins 48(4), 247-256 (1994).

String Representations

InChiKey (Click to copy)

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

SMILES (Click to copy)

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