LIPID MAPS

Structure Database (LMSD)

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Common Name

8-isoPGF2alpha

Systematic Name

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

Synonyms

(9S,11R,15S)-15-F2-IsoP[8S,12R]
15-F2t-IsoP
8-iso Prostaglandin F2alpha
15-F1t-dihomo-PhytoP-DGLA

LM ID

LMFA03110001

Formula

C₂₀H₃₄O₅

Exact Mass

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354.240626

Sum Composition

FA 20:3;O3

Status

Computationally Generated

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Classification

Biological Context

8-iso PGF2α is an isoprostane produced by the non-enzymatic peroxidation of arachidonic acid in membrane phospholipids.^1,2,3 It is present in human plasma in two distinct forms - esterified in phospholipids and as the free acid. The ratio of these two forms is approximately 2:1, with a total plasma 8-iso PGF2α level of about 150 pg/ml in normal volunteers. In normal human urine, 8-iso PGF2α levels are about 180-200 pg/mg of creatinine.^1,2 8-iso PGF2α is a weak TP receptor agonist in vascular smooth muscle.⁴ Conversely, 8-iso PGF2α inhibits platelet aggregation induced by U-46619 (10−6 M) and I-BOP (3 x 10−7 M) with IC50 values of 1.6 x 10−6 M and 1.8 x 10−6 M, respectively.³

This information has been provided by Cayman Chemical

References

1. Kiriyama, M., Ushikubi, F., Kobayashi, T., et al. Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. Br. J. Pharmacol. 122(2), 217-224 (1997).

2. Morrow, J.D., Minton, T.A., and Roberts, L.J., II The F2-isoprostane, 8-epi-prostaglandin F2α, a potent agonist of the vascular thromboxane/endoperoxide receptor, is a platelet thromboxane/endoperoxide receptor antagonist. Prostaglandins 44(2), 155-163 (1992).

3. Morrow, J.D., Harris, T.M., and Roberts, L.J., II Noncyclooxygenase oxidative formation of a series of novel prostaglandins: Analytical ramifications for measurement of eicosanoids. Anal. Biochem. 184(1), 1-10 (1990).

4. Morrow, J.D., Hill, K.E., Burk, R.F., et al. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc. Natl. Acad. Sci. USA 87(23), 9383-9387 (1990).

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)

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