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Structure Database (LMSD)

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Common Name

15R-PGF2alpha

Systematic Name

9S,11R,15R-trihydroxy-5Z,13E-prostadienoic acid

Synonyms

15R-Prostaglandin F2alpha
15-epi-PGF2alpha
8,15-diepi-15-F2t-IsoP

LM ID

LMFA03010041

Formula

C₂₀H₃₄O₅

Exact Mass

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354.240626

Sum Composition

FA 20:3;O3

Status

Curated

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Classification

Biological Context

15(R)-Prostaglandin F2α (15(R)-PGF2α) is the C-15 epimer of the naturally occurring mammalian autacoid PGF2α. It has only 25% of the potency of PGF2α in hamster antifertility studies, which may be due to reduced affinity for FP receptors.¹ Compared to PGF2α, 15(R)-PGF2α has a binding affinity of 6.7% to ovine luteal cell receptors.² Similarly, the binding affinity to rat vascular smooth muscle cells is negligible as compared to PGF2α.³

This information has been provided by Cayman Chemical

References

1. Miller, W.L., and Sutton, M.J. Relative biological activity of certain prostaglandins and their enantiomers. Prostaglandins 11(1), 77-84 (1976).

2. Hanasaki, K., Kishi, M., and Arita, H. Phorbol ester-induced expression of the common, low-affinity binding site for primary prostanoids in vascular smooth muscle cells. The Journal of Biological Chemisty 265(9), 4871-4875 (1990).

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)

PXGPLTODNUVGFL-CKXCCYAOSA-N

InChi (Click to copy)

InChI=1S/C20H34O5/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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17-,18+,19-/m1/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\CCCC(=O)O