Structure Database (LMSD)

Common Name
(+/-) 5-iPF2alpha-VI-(d11)
Systematic Name
5,9S,11R-trihydroxy-6E,14Z-prostadienoic acid-cyclo[8S,12R]-(d11)
Synonyms
LM ID
LMFA03110012
Formula
Exact Mass
Calculate m/z
365.309672
Status
Curated

Classification

Biological Context

(±)5-iPF2α-VI-d11 contains 11 deuterium atoms at the 16, 16, 17, 17, 18, 18, 19, 19, 20, 20, and 20 positions. It is intended for use as an internal standard for the quantification of (±)5-iPF2α-VI by GC- or LC-mass spectrometry. Isoprostanes are prostaglandin-like products of free-radical induced lipid peroxidation.1 Although the isoprostanes derived from arachidonic acid are the best characterized, many other polyunsaturated fatty acids can form isoprostanes.2 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).3,4 However, 8-isoprostane is a minor isoprostane constituent when compared to some of the other isomers which form in natural conditions of oxidative stress,5 including iPF2α-VI of the type-VI 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 facilitate their extraction and purification from biological samples.5,6,7,8

This information has been provided by Cayman Chemical

References

2. 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).
3. 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).
5. 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).
6. Parchmann, S., and Mueller, M.J. Evidence for the formation of dinor isoprostanes E1 from α-linolenic acid in plants. The Journal of Biological Chemisty 273, 32650-32655 (1998).
8. 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

Comments
Synthetic deuterated standard

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
RZCPXIZGLPAGEV-AOORLBIGSA-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/i1D3,2D2,3D2,4D2,5D2
SMILES (Click to copy)
C(CCCC(O)/C=C/[C@@H]1[C@@H](O)C[C@@H](O)[C@@H]1C/C=C\C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])(=O)O

Other Databases

PubChem CID
Cayman ID

Admin

Created at
-
Updated at
29th Jan 2021