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Structure Database (LMSD)

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Common Name

16,16-dimethyl-PGE2

Systematic Name

9-oxo-11R,15R-dihydroxy-16,16-dimethyl-5Z,13E-prostadienoic acid

Synonyms

16,16-dimethyl-Prostaglandin E2

LM ID

LMFA03010065

Formula

C₂₂H₃₆O₅

Exact Mass

Calculate m/z

380.256275

Sum Composition

FA 22:4;O3

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

16,16-dimethyl PGE2 is a competitive inhibitor of 15-hydroxy PGDH, but it is not a substrate for the enzyme.¹ Because of its resistance to metabolism by 15-hydroxy PGDH, it has a prolonged half-life in vivo. 16,16-dimethyl PGE2 acts as an agonist on most EP receptor subtypes, and has been used experimentally to induce cervical ripening, uterine contraction, and prevent ulceration of the gastric mucosa in rats and dogs.^2,3 The Kd for activation of isolated EP2 receptors is about 1 nM.³ 16,16-dimethyl PGE2 can be used to preserve the self-renewal properties while preventing the differentiation of hematopoietic stem cells during expansion in culture.^4,5

This information has been provided by Cayman Chemical

References

1. Hagedorn, E.J., Durand, E.M., Fast, E.M., et al. Getting more for your marrow: Boosting hematopoietic stem cell numbers with PGE2. Exp. Cell Res. (2014).

2. Genovese, P., Schiroli, G., Escobar, G., et al. Targeted genome editing in human repopulating haematopoietic stem cells. Nature 510(7504), 235-240 (2014).

3. Ohno, H., Morikawa, Y., and Hirata, F. Studies on 15-hydroxyprostaglandin dehydrogenase with various prostaglandin analogues. J. Biochem. 84(6), 1485-1494 (1978).

4. Coleman, R.A., Smith, W.L., and Narumiya, S. International Union of Pharmacology classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol. Rev. 46(2), 205-229 (1994).

5. Robert, A., Schultz, J.R., Nezamis, J.E., et al. Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16,16-dimethyl PGE2. Intravenous, oral and intrajejunal administration. Gastroenterology 70(3), 359-370 (1976).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16, 16-dimethyl PGE2. Intravenous, oral and intrajejunal administration.,
Gastroenterology, 1976

Pubmed ID: 174967

String Representations

InChiKey (Click to copy)

QAOBBBBDJSWHMU-WMBBNPMCSA-N

InChi (Click to copy)

InChI=1S/C22H36O5/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h6,8,12-13,16-17,19-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)/b8-6-,13-12+/t16-,17-,19-,20-/m1/s1

SMILES (Click to copy)

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