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Structure Database (LMSD)

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Common Name

11-deoxy-16,16-dimethyl-PGE2

Systematic Name

9-oxo-15R-hydroxy-16,16-dimethyl-5Z,13E-prostadienoic acid

Synonyms

11-deoxy-16,16-dimethyl-Prostaglandin E2

LM ID

LMFA03010062

Formula

C₂₂H₃₆O₄

Exact Mass

Calculate m/z

364.26136

Sum Composition

FA 22:4;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

11-deoxy-16,16-dimethyl Prostaglandin E2 (11-deoxy-16,16-dimethyl PGE2) is a stable synthetic analog of PGE2. It is an agonist for both EP2 and EP3 receptors.¹ It is an effective inhibitor of gastric acid secretion and ulcer formation in the rat, with ED50 values of 1 mg/kg and 0.021 mg/kg respectively.² It is 900 times more potent than PGF2α in the contraction of human respiratory tract smooth muscle in vitro.³

This information has been provided by Cayman Chemical

References

1. Lippmann, W. Inhibition of gastric acid secretion and ulcer formation in the rat by orally-administered 11-deoxyprostaglandin analogues: 15-Hydroxy-16,16-dimethyl-9-oxoprost-5,13-dienoic acids. Prostaglandins 7(3), 231-246 (1974).

2. Karim, S.M.M., Adaikan, P.G., and Kottegoda, S.R. Prostaglandins and human respiratory tract smooth muscle: Structure activity relationship. Adv. Prostaglandin Thromboxane Res. 7, 969-980 (1980).

3. Parrott, R.F., and Vellucci, S.V. Effects of centrally administered prostaglandin EP receptor agonists on febrile and adrenocortical responses in the prepubertal pig. Brain Res. Bull. 41(2), 97-103 (1996).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Inhibition of gastric acid secretion and ulcer formation in the rat by orally-administered 11-deoxyprostaglandin analogues: 15-hydroxy-16,16-dimethyl-9-oxoprost-5,13-dienoic acids.,
Prostaglandins, 1974

Pubmed ID: 4413891

String Representations

InChiKey (Click to copy)

LLVVDFDWPQHXBA-QEJIITRLSA-N

InChi (Click to copy)

InChI=1S/C22H36O4/c1-4-5-16-22(2,3)20(24)15-13-17-12-14-19(23)18(17)10-8-6-7-9-11-21(25)26/h6,8,13,15,17-18,20,24H,4-5,7,9-12,14,16H2,1-3H3,(H,25,26)/b8-6-,15-13+/t17-,18-,20-/m1/s1

SMILES (Click to copy)

[C@H]1(/C=C/[C@@H](O)C(C)(C)CCCC)CCC(=O)[C@@H]1C/C=C\CCCC(=O)O