Structure Database (LMSD)
Common Name
15R-PGE2
Systematic Name
9-oxo-11R,15R-dihydroxy-5Z,13E-prostadienoic acid
Synonyms
- 15R-Prostaglandin E2
- 8,15-diepi-15-E2t-IsoP
- 9-oxo-11R,15R-dihydroxy-5Z,13E-prostadienoic acid-cyclo[8R,12R]
LM ID
LMFA03010094
Formula
Exact Mass
Calculate m/z
352.224975
Sum Composition
Status
Curated
3D model of 15R-PGE2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
15(R)-Prostaglandin E2 (15(R)-PGE2) is the C-15 epimer of the naturally occurring 15(S)-PGE2. 15(R)-PGE2 is much less potent than the natural stereoisomer in most biological assays. In hamsters, a dose of 0.20 mg of PGE2 inhibits fertility by 100%, whereas a dose of 1.0 mg of 15(R)-PGE2 inhibits fertility by only 17%.1 15(R)-PGE2 occurs as a minor impurity in some pharmaceutical formulations of PGE2 used in obstetrics.
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).
References
String Representations
InChiKey (Click to copy)
XEYBRNLFEZDVAW-GKEZHNTDSA-N
InChi (Click to copy)
InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16-,17-,19-/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@H](O)CCCCC)[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
0
Rotatable Bonds
12
Van der Waals Molecular Volume
375.59
Topological Polar Surface Area
94.83
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.82
Molar Refractivity
98.17
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Updated at
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