LIPID MAPS

Structure Database (LMSD)

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Common Name

PGF1alpha

Systematic Name

9S,11R,15S-trihydroxy-13E-prostaenoic acid

Synonyms

Prostaglandin F1alpha

LM ID

LMFA03010137

Formula

C₂₀H₃₆O₅

Exact Mass

Calculate m/z

356.256276

Sum Composition

FA 20:2;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

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Classification

Biological Context

Prostaglandin F1α (PGF1α) is the putative metabolite of dihomo-γ-linolenic acid (DGLA) via the cyclooxygenase (COX) pathway. Both PGF1α and PGF2α have been shown to act as priming pheromones for male Atlantic salmon with a threshold concentration of 10−11 M.¹ PGF1α binds to the ovine corpus luteum FP receptor at only 8% of the relative potency of PGF2α.² It is only half as active as PGF2α in inducing human respiratory smooth muscle contractions in vitro.³

This information has been provided by Cayman Chemical

References

1. Moore, A., and Waring, C.P. Electrophysiological and endocrinological evidence that F-series prostaglandins function as priming pheromones in mature male Atlantic salmon (Salmo salar) PARR. J. Exp. Biol. 199(Pt 10), 2307-2316 (1996).

2. Karim, S.M.M., Adaikan, P.G., and Kottegoda, S.R. Prostaglandins and human respiratory tract smooth muscle: Structure activity relationship. Adv. Prostaglandin Thromboxane Res. 7, 969-980 (1980).

3. Balapure, A.K., Rexroad, C.E., Jr., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochem. Pharmacol. 38(14), 2375-2381 (1989).

String Representations

InChiKey (Click to copy)

DZUXGQBLFALXCR-CDIPTNKSSA-N

InChi (Click to copy)

InChI=1S/C20H36O5/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/h12-13,15-19,21-23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-,19+/m0/s1

SMILES (Click to copy)

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