LIPID MAPS

Structure Database (LMSD)

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Common Name

8,12-iso-iPF2alpha-VI

Systematic Name

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

Synonyms

5(R,S)-5-F2c-IsoP

LM ID

LMFA03110354

Formula

C₂₀H₃₄O₅

Exact Mass

Calculate m/z

354.240626

Sum Composition

FA 20:3;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

8,12-iso-iPF2α-VI is an isoprostane produced by non-enzymatic, free radical-induced peroxidative damage to membrane lipids. It is the most abundant isoprostane product that is formed during lipid peroxidation and is used as a biomarker for oxidative stress.¹ 8,12-iso-iPF2α-VI is detected after CCl4-induced oxidative damage to hepatic tissue and has been found elevated in the urine, blood, and cerebrospinal fluid of patients with Alzheimer’s disease.^2,3,4

This information has been provided by Cayman Chemical

References

1. 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).

2. Sicilia, T., Mally, A., Schauer, U., et al. LC-MS/MS methods for the detection of isoprostanes (iPF2α-III and 8,12-iso-iPF2α-VI) as biomarkers of CCI4-induced oxidative damage to hepatic tissue. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 861(1), 48-55 (2008).

3. Praticò, D., Clark, C.M., Liun, F., et al. Increase of brain oxidative stress in mild cognitive impairment. A possible predictor of Alzheimer disease. Arch. Neurol. 59, 972-976 (2002).

4. Shaw, L.M., Korecka, M., Clark, C.M., et al. Biomarkers of neurodegeneration for diagnosis and monitoring therapeutics. Nat. Rev. Drug Discov. 6, 295-303 (2007).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Quantitative high performance liquid chromatography/tandem mass spectrometric analysis of the four classes of F(2)-isoprostanes in human urine.,
Proc Natl Acad Sci U S A, 1999

Pubmed ID: 10557329

String Representations

InChiKey (Click to copy)

RZCPXIZGLPAGEV-DCOIXEBESA-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-/m0/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