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Structure Database (LMSD)

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Common Name

16,16-dimethyl-PGA2

Systematic Name

9oxo-15R-hydroxy-16,16-dimethyl-5Z,10Z,13E-prostatrienoic acid

Synonyms

16,16-dimethyl-Prostaglandin A2

LM ID

LMFA03010086

Formula

C₂₂H₃₄O₄

Exact Mass

Calculate m/z

362.24571

Sum Composition

FA 22:5;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

16,16-dimethyl PGA2 is a metabolism-resistant analog of PGA2 with a prolonged in vivo half-life. It inhibits the proliferation of Sendai virus in cultured African green monkey kidney cells by >90% at a concentration of 4 µg/ml.¹ Daily infusion of 10 µg of 16,16-dimethyl PGA2 methyl ester into mice infected with influenza A virus increased survival by 40%.² Similar treatment of mice inoculated with erythroleukemia cells delayed tumor growth and increased survival time.³

This information has been provided by Cayman Chemical

References

1. Santoro, M.G., Favalli, C., Mastino, A., et al. Antiviral activity of a synthetic analog of prostaglandin A in mice infected with influenza A virus. Arch. Virol. 99, 89-100 (1988).

2. Marini, S., Palamara, A.T., Garaci, E., et al. Growth inhibition of friend erythroleukaemia cell tumours in vivo by a synthetic analogue of prostaglandin A: An action independent of natural killer-activity. Br. J. Cancer 61, 394-399 (1990).

3. Santoro, M.G., Benedetto, A., Carruba, G., et al. Prostaglandin A compounds as antiviral agents. Science 209, 1032-1034 (1980).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Antiviral activity of a synthetic analog of prostaglandin A in mice infected with influenza A virus.,
Arch Virol, 1988

Pubmed ID: 3355375

String Representations

InChiKey (Click to copy)

MOTPSJUHMGPRFZ-QEJIITRLSA-N

InChi (Click to copy)

InChI=1S/C22H34O4/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/h6,8,12-15,17-18,20,24H,4-5,7,9-11,16H2,1-3H3,(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)C=CC(=O)[C@@H]1C/C=C\CCCC(=O)O