Structure Database (LMSD)
Common Name
11-deoxy-PGE1
Systematic Name
9-oxo-15S-hydroxy-13E-prostaenoic acid
Synonyms
- 11-deoxy-Prostaglandin E1
- Doproston
LM ID
LMFA03010054
Formula
Exact Mass
Calculate m/z
338.24571
Sum Composition
Status
Curated
3D model of 11-deoxy-PGE1
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
11-deoxy Prostaglandin E1 (11-deoxy PGE1) is a synthetic analog of PGE1. Early reports show that it is a selective agonist for the EP2 receptor but effective at much higher concentrations than PGE2.1,2 However, later studies show that it is a non-selective agonist of EP receptors and stimulates cAMP release in Jurkat cells with an EC50 of 0.25 µM.3 11-deoxy PGE1 also exhibits vasodepressor and bronchodilator responses in guinea pigs.4 11-deoxy PGE1 exhibits selectively for the mouse EP3 receptor and is essentially equipotent to PGE1 at this receptor subtype. The Ki values for binding to the mouse EP1, EP2, EP3, and EP4 receptors are 600, 45, 1.1, and 23 nM, respectively.5
This information has been provided by Cayman Chemical
References
2. Hall, D.W.R., and Jaitly, K.D. Structure-activity relationships in a series of 11-deoxy prostaglandins. Prostaglandins 11(3), 573-587 (1976).
3. De Vries, G.W., Guarino, P., McLaughlin, A., et al. An EP receptor with a novel pharmacological profile in the T-cell line Jurkat. Br. J. Pharmacol. 115(7), 1231-1234 (1995).
4. Dong, Y.J., Jones, R.L., and Wilson, N.H. Prostaglandin E receptor subtypes in smooth muscle: Agonist activities of stable prostacyclin analogues. Br. J. Pharmacol. 87(1), 97-107 (1986).
5. Chen, J., and Woodward, D.F. Prostanoid-induced relaxation of precontracted cat ciliary muscle is mediated by EP2 and DP receptors. Invest. Ophthalmol. Vis. Sci. 33(11), 3195-3201 (1992).
References
String Representations
InChiKey (Click to copy)
DPNOTBLPQOITGU-LDDQNKHRSA-N
InChi (Click to copy)
InChI=1S/C20H34O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12,14,16-18,21H,2-11,13,15H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)CCC(=O)[C@@H]1CCCCCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
1
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
369.44
Topological Polar Surface Area
74.60
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
4.79
Molar Refractivity
96.36
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Created at
-
Updated at
13th Jan 2021