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Structure Database (LMSD)

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Common Name

17-phenyl-trinor-PGE2

Systematic Name

9-oxo-11R,15S-dihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoic acid

Synonyms

17-phenyl-trinor-Prostaglandin E2

LM ID

LMFA03010067

Formula

C₂₃H₃₀O₅

Exact Mass

Calculate m/z

386.209325

Sum Composition

FA 23:8;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

17-phenyl trinor Prostaglandin E2 (17-phenyl trinor PGE2) is a synthetic analog of PGE2. It is an EP1 and EP3 receptor agonist.^1,2 17-phenyl trinor PGE2 causes contraction of the guinea pig ileum at a concentration of 11 µM.¹ It is slightly less potent than PGE2 in stimulating gerbil colon and rat uterus.² With an ED50 value of 350 µg/kg, 17-phenyl trinor PGE2 is 4.4 times more potent than PGE2 as an antifertility agent in hamsters.²

This information has been provided by Cayman Chemical

References

1. Miller, W.L., Weeks, J.R., Lauderdale, J.W., et al. Biological activities of 17-phenyl-18,19,20-trinorprostaglandins. Prostaglandins 9(1), 9-18 (1975).

2. Lawrence, R.A., Jones, R.L., and Wilson, N.H. Characterization of receptors involved in the direct and indirect actions of prostaglandins E and I on the guinea-pig ileum. Br. J. Pharmacol. 105(2), 271-278 (1992).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Biological activities of 17-phenyl-18,19,20-trinorprostaglandins.,
Prostaglandins, 1975

Pubmed ID: 806103

String Representations

InChiKey (Click to copy)

FOBVMYJQWZOGGJ-XYRJXBATSA-N

InChi (Click to copy)

InChI=1S/C23H30O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-20,22,24,26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,22+/m0/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)CCC2C=CC=CC=2)[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O