Structure Database (LMSD)
Common Name
19R-hydroxy-PGE2
Systematic Name
9-oxo-11R,15S,19R-trihydroxy-5Z,13E-prostadienoic acid
Synonyms
- 19(R)-hydroxy-Prostaglandin E2
- 19-hydroxy-PGE2
- 19-OH-PGE2
- 19(R)-OH PGE2
LM ID
LMFA03010024
Formula
Exact Mass
Calculate m/z
368.219891
Sum Composition
Status
Curated
3D model of 19R-hydroxy-PGE2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
19(R)-hydroxy Prostaglandin E2 (19(R)-hydroxy PGE2) is found in the semen of primates, including man.1 It is a potent smooth muscle relaxant and a selective agonist for the EP2 receptor.1,2 It has an EC50 value of 200 nM for relaxing cat tracheal rings which express EP2 receptors.2
This information has been provided by Cayman Chemical
References
1. Woodward, D.F., Protzman, C.E., Krauss, A.H.P., et al. Identification of 19(R)-OH prostaglandin E2 as a selective prostanoid EP2-receptor agonist. Prostaglandins 46(4), 371-383 (1993).
2. Kelly, R.W., Taylor, P.L., Hearn, J.P., et al. 19-Hydroxyprostaglandin E1 as a major component of the semen of primates. Nature 260(5551), 544-545 (1976).
References
String Representations
InChiKey (Click to copy)
WTJYDBMHYPQFNJ-ZUVVJKHESA-N
InChi (Click to copy)
InChI=1S/C20H32O6/c1-14(21)7-6-8-15(22)11-12-17-16(18(23)13-19(17)24)9-4-2-3-5-10-20(25)26/h2,4,11-12,14-17,19,21-22,24H,3,5-10,13H2,1H3,(H,25,26)/b4-2-,12-11+/t14-,15+,16-,17-,19-/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCC[C@H](O)C)[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O
Other Databases
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR1713
PubChem CID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
1
Aromatic Rings
0
Rotatable Bonds
12
Van der Waals Molecular Volume
384.38
Topological Polar Surface Area
115.06
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
6
logP
3.08
Molar Refractivity
100.07
Admin
Created at
-
Updated at
20th Feb 2025