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

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Pregnancy interception with a combination of prostaglandins: studies in monkeys.,
Science, 1983
Pubmed ID: 6612350

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

CHEBI ID
LIPIDBANK ID
XPR1741
PubChem CID
Cayman ID

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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