LIPID MAPS

Structure Database (LMSD)

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Common Name

PGA3

Systematic Name

9-oxo-15S-hydroxy-5Z,10Z,13E,17Z-prostatetraenoic acid

Synonyms

Prostaglandin A3

LM ID

LMFA03010140

Formula

C₂₀H₂₈O₄

Exact Mass

Calculate m/z

332.19876

Sum Composition

FA 20:6;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Cyclooxygenase metabolism of EPA to produce Prostaglandin E3 (PGE3) has been reported in biosynthetic preparations of ovine seminal vesicles1 and in the ocular tissues of primates.² Prostaglandin A3 (PGA3) is an expected non-enzymatic dehydration product of this PGE3. PGA3 exhibits good affinity for the canine EP2 and EP4 receptors with IC50 values of 120 nM and 20 nM, respectively, in a radioligand binding assay.^3,4 PGA3 has weak affinity for human PPARγ, with a Ki value of 188 µM.⁵

This information has been provided by Cayman Chemical

References

1. Castleberry, T.A., Lu, B., Smock, S.L., et al. Molecular cloning and functional charcterization of the canine prostaglandin E2 receptor EP4 subtype. Prostaglandins Other Lipid Mediat. 65(4), 167-187 (2001).

2. Hibbs, T.A., Lu, B., Smock, S.L., et al. Molecular cloning and charcterization of the canine prostaglandin E receptor EP2 subtype. Prostaglandins Other Lipid Mediat. 57(2-3), 133-147 (1999).

3. Ferry, G., Bruneau, V., Beauverger, P., et al. Binding of prostaglandins to human PPARγ: Tool assessment and new natural ligands. Eur. J. Pharmacol. 417(1-2), 77-89 (2001).

4. Kulkarni, P.S., Kaufman, P.L., and Srinivasan, B.D. Eicosapentaenoic acid metabolism in cynomolgus and rhesus conjunctiva and eyelid. J. Ocul. Pharmacol. 3(4), 349-356 (1987).

5. Lohmus, M., Vahemets, A., Järving, I., et al. Preparative separation of natural prostaglandins E. Preparative Chromatography 1(3), 279-300 (1991).

String Representations

InChiKey (Click to copy)

KSIRMUMXJFWKAC-FHJHOUOTSA-N

InChi (Click to copy)

InChI=1S/C20H28O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h3-4,6-7,12-18,21H,2,5,8-11H2,1H3,(H,23,24)/b6-3-,7-4-,14-12+/t16-,17-,18+/m0/s1

SMILES (Click to copy)

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