Structure Database (LMSD)
Common Name
9-deoxy-9-methylene-16,16-dimethyl -PGE2
Systematic Name
9-methylene-11R,15S-dihydroxy-16,16-dimethyl-5Z,13E-prostadienoic acid
Synonyms
- 9-deoxy-9-methylene-16,16-dimethyl -Prostaglandin E2
LM ID
LMFA03010059
Formula
Exact Mass
Calculate m/z
378.27701
Sum Composition
Status
Curated
3D model of 9-deoxy-9-methylene-16,16-dimethyl -PGE2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
9-deoxy-9-methylene-16,16-dimethyl Prostaglandin E2 (Meteneprost) is a potent analog of prostaglandin E2 (PGE2) with an extended half-life in vivo. In combination with various other prostaglandin derivatives, it results in the termination of first trimester pregnancy in monkeys. A single intramuscular injection containing 0.5 mg of meteneprost and 7.5 mg of 17-phenyl trinor PGF1α is very effective in terminating early pregnancy.1 This prostaglandin mixture is ineffective on monkeys in their third trimester of pregnancy.1 Meteneprost, when compared to PGE2 and PGF1α, in monkey and rat, does not result in unwanted side effects such as fever or gastrointestinal problems.1,2
This information has been provided by Cayman Chemical
References
1. Bundy, G.L., Kimball, F.A., Robert, A., et al. Synthesis and biological activity of 9-deoxo-9-methylene and related prostaglandins. Adv. Prostaglandin Thromboxane Res. 6, 355-363 (1980).
References
String Representations
InChiKey (Click to copy)
WMLGLMGSFIXSGO-KTXJXPLISA-N
InChi (Click to copy)
InChI=1S/C23H38O4/c1-5-6-15-23(3,4)21(25)14-13-19-18(17(2)16-20(19)24)11-9-7-8-10-12-22(26)27/h7,9,13-14,18-21,24-25H,2,5-6,8,10-12,15-16H2,1,3-4H3,(H,26,27)/b9-7-,14-13+/t18-,19+,20+,21+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)C(C)(C)CCCC)[C@H](O)CC(=C)[C@@H]1C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
1
Aromatic Rings
0
Rotatable Bonds
12
Van der Waals Molecular Volume
418.70
Topological Polar Surface Area
77.76
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
5.45
Molar Refractivity
111.46
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Updated at
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