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

Classification

Biological Context

Prostaglandin D2 (PGD2; Item No. 12010) is one of the five primary enzymatic prostaglandins derived directly from PGH2 (Item No. 17020). 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).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
ChemInform Abstract: Synthesis of 11-Deoxo-11-methylene-prostaglandin D2 and Its Derivatives.,
Chem Pharm Bull, 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

CHEBI ID
LIPIDBANK ID
XPR1773
PubChem CID
Cayman ID

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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Created at
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Updated at
5th Apr 2022