LIPID MAPS

Structure Database (LMSD)

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Common Name

8-iso-15-keto-PGF2alpha

Systematic Name

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

Synonyms

LM ID

LMFA03110005

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-15-keto Prostaglandin F2α (8-iso-15-keto PGF2α) is a metabolite of the isoprostane 8-iso PGF2α in rabbits, monkeys, and humans. 8-isoprostane (8-iso PGF2α) is a prostaglandin-like product of non-specific lipid peroxidation.¹ In both humans and monkeys, exogenously infused 8-iso PGF2α is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation.² A similar pattern is observed when tritiated 8-iso PGF2α is infused into rabbits.³ Early in the infusion (within 1-2 minutes) 8-iso -15-keto PGF2α was a major component of the metabolite profile, which was comprised mostly of unmetabolized 8-iso PGF2α. 8-iso -15-keto PGF2α is a vasoconstrictor when tested on the rat isolated thoracic aorta, acting via the TP (thromboxane) receptor.⁴

This information has been provided by Cayman Chemical

References

1. Cracowski, J.L., Camus, L., Durand, T., et al. Response of rat thoracic aorta to F2-isoprostane metabolites. J. Cardiovasc. Pharmacol. 39(3), 396-403 (2002).

2. Basu, S. Metabolism of 8-iso-prostaglandin F2α. FEBS Lett. 428(112), 32-36 (1998).

3. Chiabrando, C., Valagussa, A., Rivalta, C., et al. Identification and measurement of endogenous β-oxidation metabolites of 8-epi-prostaglandin F2α. J. Biol. Chem. 274(3), 1313-1319 (1999).

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).

String Representations

InChiKey (Click to copy)

LOLJEILMPWPILA-RLXHZABYSA-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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,18-,19+/m0/s1

SMILES (Click to copy)

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