compound 25 [PMID: 35439007]   Click here for help

GtoPdb Ligand ID: 11971

Compound class: Synthetic organic
Comment: This compound inhibits the N7-methyltransferase RNA capping activity of SARS-CoV-2 nsp14 [1]. It is a dinucleoside mimetic of S-adenosyl-l-methionine (SAM; a.k.a. S-adenosyl methionine) that is the methyl donor for the reaction catalysed by nsp14. Compound 25 is selective for nsp14 compared to human RNA N7-MTase (RNMT: O43148).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 198.09
Molecular weight 489.14
XLogP -0.18
No. Lipinski's rules broken 1
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Canonical SMILES CCN(S(=O)(=O)c1ccc(c(c1)C#N)OC)C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
Isomeric SMILES O[C@@H]1[C@H](O)[C@@H](CN(CC)S(=O)(=O)c2ccc(OC)c(C#N)c2)O[C@H]1n1cnc2c1ncnc2N
InChI InChI=1S/C20H23N7O6S/c1-3-26(34(30,31)12-4-5-13(32-2)11(6-12)7-21)8-14-16(28)17(29)20(33-14)27-10-25-15-18(22)23-9-24-19(15)27/h4-6,9-10,14,16-17,20,28-29H,3,8H2,1-2H3,(H2,22,23,24)/t14-,16-,17-,20-/m1/s1
1. Ahmed-Belkacem R, Hausdorff M, Delpal A, Sutto-Ortiz P, Colmant AMG, Touret F, Ogando NS, Snijder EJ, Canard B, Coutard B et al.. (2022)
Potent Inhibition of SARS-CoV-2 nsp14 N7-Methyltransferase by Sulfonamide-Based Bisubstrate Analogues.
J Med Chem, 65 (8): 6231-6249. [PMID:35439007]