Structure Database (LMSD)
Common Name
11-deoxy-11-methylene-PGD2
Systematic Name
9S,15S-dihydroxy-11-methylene-5Z,13E-prostadienoic acid
Synonyms
- 11-deoxy-11-methylene-Prostaglandin D2
LM ID
LMFA03010103
Formula
Exact Mass
Calculate m/z
350.24571
Sum Composition
Status
Curated
3D model of 11-deoxy-11-methylene-PGD2
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Prostaglandin D2 (PGD2) is one of the five primary enzymatic prostaglandins derived directly from PGH2 . PGD2 is produced abundantly in the CSF by the lipocalin-type PGD synthase, and in the periphery by myeloid cells including mast cells and basophils by a second, leukocyte-type PGD synthase.1 PGD2 is chemically unstable, and its use and analysis is complicated by its short in vivo half-life. 11-deoxy-11-methylene PGD2 is a novel, chemically stable, isosteric analog of PGD2 wherein the 11-keto group is replaced by an exocyclic methylene. In the PGE series, the analogous modification leads to a stable, somewhat less potent agonist which embodies the same uterine stimulant and cervical ripening activities as the parent prostaglandin.2 However, 11-deoxy-11-methylene PGD2 has been reported by one group to be essentially without agonist activity on human platelets, a DP1 receptor assay.3 The CRTH2-receptor actions of 11-deoxy-11-methylene PGD2 are not yet reported.
This information has been provided by Cayman Chemical
References
1. Borten, M., DiLeo, L.A., and Friedman, E.A. Low-dose prostaglandin E2 analogue for cervical dilations prior to pregnancy termination. Am. J. Obstet. Gynecol. 150(5 Pt 1), 561-565 (1984).
2. Urade, Y., and Hayaishi, O. Prostaglandin D synthase: Structure and function. Vitam. Horm. 58, 89-120 (2000).
3. Torisawa, Y., Yamaguchi, T., Sakata, S., et al. Synthesis of 11-deoxo-11-methylene-prostaglandin D2 and its derivatives. Chem. Pharm. Bull. (Tokyo) 33(10), 4625-4628 (1985).
String Representations
InChiKey (Click to copy)
ROZAFJXVUNORLT-SFIVEXQWSA-N
InChi (Click to copy)
InChI=1S/C21H34O4/c1-3-4-7-10-17(22)13-14-18-16(2)15-20(23)19(18)11-8-5-6-9-12-21(24)25/h5,8,13-14,17-20,22-23H,2-4,6-7,9-12,15H2,1H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19+,20-/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCCCC)C(=C)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
1
Aromatic Rings
0
Rotatable Bonds
12
Van der Waals Molecular Volume
384.10
Topological Polar Surface Area
77.76
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
4
logP
4.81
Molar Refractivity
102.30
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Updated at
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