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Structure Database (LMSD)

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Common Name

PGF2alpha alcohol

Systematic Name

1,9S,11R,15S-tetrahydroxy-5Z,13E-prostadiene

Synonyms

Prostaglandin F2alpha alcohol

LM ID

LMFA03010113

Formula

C₂₀H₃₆O₄

Exact Mass

Calculate m/z

340.26136

Sum Composition

FOH 20:2;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Prostaglandin F2α alcohol (PGF2α-OH) is an analog of PGF2α in which the C-1 carboxyl group has been reduced to a primary alcohol. Biological studies on rat uterus show it to be a weak agonist.¹ The compound is reported to retain ocular hypotensive properties,2 but the nature of the receptors which mediate these effects is disputed.³

This information has been provided by Cayman Chemical

References

1. Woodward, D.F., and Chan, M.F. Preparation of PGF-1 alcohols as ocular hypotensives. 38204, 1-12 (1993).

2. Brambaifa, N. Luteolytic potency of PGD and PGF2α derivatives. Eur. J. Obstet. Gynecol. Reprod. Biol. 27(4), 319-325 (1988).

3. Woodward, D.F., Krauss, A.H.P., Chen, J., et al. Replacement of the carboxylic acid group of prostaglandin F2α with a hydroxyl or methoxy substituent provides biologically unique compounds. Br. J. Pharmacol. 130(8), 1933-1943 (2000).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Replacement of the carboxylic acid group of prostaglandin f(2alpha) with a hydroxyl or methoxy substituent provides biologically unique compounds.,
Br J Pharmacol, 2000

Pubmed ID: 10952685

String Representations

InChiKey (Click to copy)

QYBXRFWLQYXAPC-LFZNYWNYSA-N

InChi (Click to copy)

InChI=1S/C20H36O4/c1-2-3-7-10-16(22)12-13-18-17(19(23)15-20(18)24)11-8-5-4-6-9-14-21/h5,8,12-13,16-24H,2-4,6-7,9-11,14-15H2,1H3/b8-5-,13-12+/t16-,17+,18+,19-,20+/m0/s1

SMILES (Click to copy)

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