LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

11-deoxy-PGF1a

Systematic Name

9S,15S-dihydroxy-13E-prostaenoic acid

Synonyms

11-deoxy-Prostaglandin F1a

LM ID

LMFA03010068

Formula

C₂₀H₃₆O₄

Exact Mass

Calculate m/z

340.261361

Sum Composition

FA 20:2;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

11-deoxy Prostaglandin F1α (11-deoxy PGF1α) is a synthetic analog of PGF1α. In whole animal studies, a dose of 32 mg/kg inhibited gastric acid secretion by 35%.¹ 11-deoxy PGF1α is also known to cause rat uterine contractions at a dose 0.3 times that of PGF1α.² It also exhibits vasopressor and bronchoconstrictor activities at about half the potency of PGF2α in guinea pigs.³

This information has been provided by Cayman Chemical

References

1. Hall, D.W.R., and Jaitly, K.D. Structure-activity relationships in a series of 11-deoxy prostaglandins. Prostaglandins 11(3), 573-587 (1976).

2. Broughton, B.J., Caton, M.P.L., Christmas, A.J., et al. Uterine stimulant action of some ω-chain modified (±)-11-deoxyprostaglandins. Prostaglandins 22(1), 53-64 (1981).

3. Lippmann, W. Inhibition of gastric acid secretion in the rat by synthetic prostaglandins. J. Pharm. Pharmacol. 21(5), 335-336 (1969).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Structure-activity relationships in a series of 11-deoxy prostaglandins.,
Prostaglandins, 1976

Pubmed ID: 948628

String Representations

InChiKey (Click to copy)

HYBPXYQCXNOTFK-DUSCRHDRSA-N

InChi (Click to copy)

InChI=1S/C20H36O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12,14,16-19,21-22H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+,19-/m0/s1

SMILES (Click to copy)

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