PSB-6426   Click here for help

GtoPdb Ligand ID: 9033

Synonyms: compound 19a [PMID: 18630897]
Compound class: Synthetic organic
Comment: PSB-6426 is a tool compound which inhibits ectonucleoside triphosphate diphosphohydrolase 2 (ENTPD2, CD39L1) [1]. Structurally it is a uridine derivative, and it was the most potent compound discovered in a series designed to find novel structures with potential cardioprotective action.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 5
Rotatable bonds 13
Topological polar surface area 208.09
Molecular weight 540.16
XLogP -0.25
No. Lipinski's rules broken 2
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Canonical SMILES CCOP(=O)(Cc1ccc(cc1)NC(=O)CNC(=O)C1OC(C(C1O)O)n1ccc(=O)[nH]c1=O)OCC
Isomeric SMILES CCOP(=O)(Cc1ccc(cc1)NC(=O)CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(=O)[nH]c1=O)OCC
InChI InChI=1S/C22H29N4O10P/c1-3-34-37(33,35-4-2)12-13-5-7-14(8-6-13)24-16(28)11-23-20(31)19-17(29)18(30)21(36-19)26-10-9-15(27)25-22(26)32/h5-10,17-19,21,29-30H,3-4,11-12H2,1-2H3,(H,23,31)(H,24,28)(H,25,27,32)/t17-,18+,19-,21+/m0/s1
1. Brunschweiger A, Iqbal J, Umbach F, Scheiff AB, Munkonda MN, Sévigny J, Knowles AF, Müller CE. (2008)
Selective nucleoside triphosphate diphosphohydrolase-2 (NTPDase2) inhibitors: nucleotide mimetics derived from uridine-5'-carboxamide.
J Med Chem, 51 (15): 4518-28. [PMID:18630897]