Structure Database (LMSD)
Common Name
19R-hydroxy-PGE1
Systematic Name
9-oxo-11R,15S,19R-trihydroxy-13E-prostaenoic acid
Synonyms
- 19(R)-hydroxy-Prostaglandin E1
LM ID
LMFA03010147
Formula
Exact Mass
Calculate m/z
370.23554
Sum Composition
Status
Curated
3D model of 19R-hydroxy-PGE1
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 PGE1 is the major prostaglandin found in the semen of primates, including man. It is an agonist for the EP1 and EP3 receptor subtypes, and exhibits contractile activity on smooth muscle preparations.1,2 It has an EC50 of 320 nM for contracting guinea pig ileum, which express EP1 receptors, and an EC50 of 80 nM for contracting chick ileum, which express EP3 receptors.2
This information has been provided by Cayman Chemical
References
1. 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).
2. 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).
References
String Representations
InChiKey (Click to copy)
QVVXWHIDRKRPMO-VOSXNNSYSA-N
InChi (Click to copy)
InChI=1S/C20H34O6/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/h11-12,14-17,19,21-22,24H,2-10,13H2,1H3,(H,25,26)/b12-11+/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]1CCCCCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
26
Rings
1
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
387.02
Topological Polar Surface Area
115.06
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
6
logP
3.31
Molar Refractivity
100.16
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Updated at
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