LIPID MAPS

Structure Database (LMSD)

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Common Name

(+/-) 5-iPF2alpha-VI

Systematic Name

5,9S,11R-trihydroxy-6E,14Z-prostadienoic acid-cyclo[8S,12R]

Synonyms

Isoprostane F2alpha-I
iPF2alpha-I
5-iso-PGF2a VI
5(R,S)-5-F2t-IsoP

LM ID

LMFA03110011

Formula

C₂₀H₃₄O₅

Exact Mass

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354.240626

Sum Composition

FA 20:3;O3

Status

Curated

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Classification

Biological Context

(±)5-iPF2α-VI is one of dozens of possible stereo- and regioisomeric isoprostanes which can be formed from arachidonic acid. To date, the most extensively studied of these is 8-isoprostane (8-epi-PGF2α, iPF2α-III).^1,2 However, 8-isoprostane is a minor isoprostane constituent when compared to some of the other isomers which form in natural conditions of oxidative stress.³ (±)5-iPF2α-VI is an isoprostane from the unique Type VI class of isoprostanes. This class has been shown to be one of the major isoprostane products, in contrast to 8-isoprostane. In addition to being produced in greater abundance than 8-isoprostane, Type VI isoprostanes form internal lactones, which facilitates their extraction and purification from biological samples.^3,4,5,6

This information has been provided by Cayman Chemical

References

1. Delanty, N., Reilly, M., Pratico, D., et al. 8-Epi PGF2α: Specific analysis of an isoeicosanoid as an index of oxidant stress in vivo. Br. J. Clin. Pharmacol. 42, 15-19 (1996).

2. Reilly, M.P., Barry, P., Lawson, J.A., et al. Urinary 8-epi PGF2α: An index of oxidant stress in vivo. Fibrinolysis & Proteolysis 11, 81-84 (1997).

3. Praticò, D., Barry, O.P., Lawson, J.A., et al. IPF2α-I: An index of lipid peroxidation in humans. Proc. Natl. Acad. Sci. USA 95, 3449-3454 (1998).

4. Lawson, J.A., Li, H., Rokach, J., et al. Identification of two major F2 isoprostanes, 8,12-iso- and 5-epi-8,12-iso-isoprostane F2α-VI, in human urine. The Journal of Biological Chemisty 273(45), 29295-29301 (1998).

5. Reilly, M.P., Pratico, D., Delanty, N., et al. Increased formation of distinct F2 isoprostanes in hypercholesterolemia. Circulation 98, 2822-2828 (1998).

6. Li, H., Lawson, J.A., Reilly, M., et al. Quantitative high performance liquid chromatography/tandem mass spectrometric analysis of the four classes of F2-isoprostanes in human urine. Proc. Natl. Acad. Sci. USA 96(23), 13381-13386 (1999).

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)

RZCPXIZGLPAGEV-SUHLLOIRSA-N

InChi (Click to copy)

InChI=1S/C20H34O5/c1-2-3-4-5-6-7-10-16-17(19(23)14-18(16)22)13-12-15(21)9-8-11-20(24)25/h6-7,12-13,15-19,21-23H,2-5,8-11,14H2,1H3,(H,24,25)/b7-6-,13-12+/t15?,16-,17+,18-,19+/m1/s1

SMILES (Click to copy)

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