LIPID MAPS

Structure Database (LMSD)

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Common Name

Delta17, 6-keto PGF1a

Systematic Name

6-oxo-9S,11R,15S-trihydroxy-13E,17Z-prostadienoic acid

Synonyms

Delta17, 6-keto Prostaglandin F1a

LM ID

LMFA03010149

Formula

C₂₀H₃₂O₆

Exact Mass

Calculate m/z

368.219891

Sum Composition

FA 20:4;O4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Δ17-6-keto Prostaglandin F1α (Δ17-6-keto PGF1α) is a cyclooxygenase (COX) product of eicosapentaenoic acid (EPA) in various tissues such as seminal vesicles, lung, Polymorphonuclear leukocytes, and ocular tissues.^1,2 Δ17-6-keto PGF1α and other 3-series COX products from EPA, such as PGF3α, PGE3, and thromboxane B3, may be involved in the reduced incidence of glaucoma in patients on a marine-rich (EPA-rich) diet.

This information has been provided by Cayman Chemical

References

1. Kulkarni, P.S., and Srinivasan, B.D. Eicosapentaenoic acid metabolism in human and rabbit anterior uvea. Prostaglandins 31(6), 1159-1164 (1986).

2. Kulkarni, P.S., Kaufman, P.L., and Srinivasan, B.D. Eicosapentaenoic acid metabolism in cynomolgus and rhesus conjunctiva and eyelid. J. Ocul. Pharmacol. 3(4), 349-356 (1987).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Prostaglandin I3 is formed in vivo in man after dietary eicosapentaenoic acid.,
Nature, 1984

Pubmed ID: 6318123

Ovis aries (#9940)

Mammalia (#40674)

Preparation and biochemical properties of PGH3.,
Prostaglandins, 1979

Pubmed ID: 531219

String Representations

InChiKey (Click to copy)

HFKNJQYMAGMXTR-CAPHXMBKSA-N

InChi (Click to copy)

InChI=1S/C20H32O6/c1-2-3-4-7-14(21)10-11-16-17(19(24)13-18(16)23)12-15(22)8-5-6-9-20(25)26/h3-4,10-11,14,16-19,21,23-24H,2,5-9,12-13H2,1H3,(H,25,26)/b4-3-,11-10+/t14-,16+,17+,18+,19-/m0/s1

SMILES (Click to copy)

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