LIPID MAPS

Structure Database (LMSD)

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Common Name

8-iso-PGE1

Systematic Name

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

Synonyms

LM ID

LMFA03110002

Formula

C₂₀H₃₄O₅

Exact Mass

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354.240625

Sum Composition

FA 20:3;O3

Status

Curated

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Classification

Biological Context

Isoprostanes are a family of prostanoid molecules of non-cyclooxygenase origin.¹ 8-iso Prostaglandin E1 (8-iso PGE1) is an isoprostane which is found in human semen at levels of 7 µg/ml.² It is a pulmonary vasoconstrictor in anesthetized dogs with a potency similar to PGF2α.³

This information has been provided by Cayman Chemical

References

1. 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).

2. Taylor, P.L. The 8-isoprostaglandins: Evidence for eight compounds in human semen. Prostaglandins 17(2), 259-267 (1979).

3. Nakano, J., and Kessinger, J.M. Effects of 8-isoprostaglandin E1 on the systemic and pulmonary circulations in dogs. Proc. Soc. Exp. Biol. Med. 133(4), 1314-1317 (1970).

String Representations

InChiKey (Click to copy)

GMVPRGQOIOIIMI-JCPCGATGSA-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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17+,19+/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@H](O)CC(=O)[C@H]1CCCCCCC(=O)O