LIPID MAPS

Structure Database (LMSD)

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Common Name

PGF2alpha-1,11-lactone

Systematic Name

9S,15S-dihydroxy-5Z,13E-prostadienoic acid-1,11R-lactone

Synonyms

Prostaglandin F2alpha-1,11-lactone

LM ID

LMFA03010071

Formula

C₂₀H₃₂O₄

Exact Mass

Calculate m/z

336.23006

Sum Composition

FA 20:4;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Prostaglandin F2α (PGF2α) 1,11-lactone is a lipid-soluble internal ester of PGF2α. Hydrolysis of the lactone by plasma esterases readily produces free PGF2α in rats and monkeys, but not in humans.¹ PGF2α 1,11-lactone is active as an antifertility agent with greatly reduced vasoactivity compared to PGF2α.¹

This information has been provided by Cayman Chemical

References

1. Bundy, G.L., Peterson, D.C., Cornette, J.C., et al. Synthesis and biological activity of prostaglandin lactones. J. Med. Chem. 26(8), 1089-1099 (1983).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Synthesis and biological activity of prostaglandin lactones.,
J Med Chem, 1983

Pubmed ID: 6876076

String Representations

InChiKey (Click to copy)

KBFCVOAVUKWCPS-YNNPMVKQSA-N

InChi (Click to copy)

InChI=1S/C20H32O4/c1-2-3-6-9-15(21)12-13-17-16-10-7-4-5-8-11-20(23)24-19(17)14-18(16)22/h4,7,12-13,15-19,21-22H,2-3,5-6,8-11,14H2,1H3/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCCCC)[C@@H]2OC(=O)CCCC=CC[C@H]1[C@@H](O)C2