compound 49 [PMID: 36529947]   Click here for help

GtoPdb Ligand ID: 12355

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: This compound is an orally bioavailable inhibitor of the immuno-oncology drug target 5'-nucleotidase ecto (NT5E; CD73) [1]. It was designed to block NT5E-mediated generation of immunosuppressive adenosine in the tumour microenvironment, as a mechanism to re-establish immune-mediated antitumour activity.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 15
Hydrogen bond donors 6
Rotatable bonds 9
Topological polar surface area 235.48
Molecular weight 615.15
XLogP -0.24
No. Lipinski's rules broken 2
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Canonical SMILES C#C[C@@]1(O)[C@@H](COC(C(=O)O)(C(=O)O)Cc2ccc(cc2)N2CCCNC2=O)O[C@H]([C@@H]1O)n1cnc2c1nc(Cl)nc2N
Isomeric SMILES Clc1nc(N)c2c(n1)n(cn2)[C@H]1[C@H](O)[C@@](O)(C#C)[C@@H](COC(C(=O)O)(Cc2ccc(N3C(=O)NCCC3)cc2)C(=O)O)O1
InChI InChI=1S/C26H26ClN7O9/c1-2-25(41)15(43-20(17(25)35)34-12-30-16-18(28)31-23(27)32-19(16)34)11-42-26(21(36)37,22(38)39)10-13-4-6-14(7-5-13)33-9-3-8-29-24(33)40/h1,4-7,12,15,17,20,35,41H,3,8-11H2,(H,29,40)(H,36,37)(H,38,39)(H2,28,31,32)/t15-,17+,20-,25-/m1/s1
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-[[(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3-ethynyl-3,4-dihydroxyoxolan-2-yl]methoxy]-2-[[4-(2-oxo-1,3-diazinan-1-yl)phenyl]methyl]propanedioic acid
Database Links Click here for help
BindingDB Ligand 511076
GtoPdb PubChem SID 479821146
PubChem CID 146276619
Search Google for chemical match using the InChIKey ROWSPNRRBJYDCU-IRJNKLFQSA-N
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