compound 25 [PMID: 31260299]   Click here for help

GtoPdb Ligand ID: 10428

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 25 is a potent, selective and reversible inhibitor of Bruton's tyrosine kinase (BTK) [2]. It is built on a 4-aminoquinoline scaffold, and has improved drug-like properties (aqueous solubility, potency and stability) compared to previously reported cinnoline scaffold compounds [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 119.91
Molecular weight 351.11
XLogP 2.77
No. Lipinski's rules broken 0
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Canonical SMILES COc1cc2cn[nH]c2cc1c1ccc(c2c1ncc(c2N)C(=O)N)F
Isomeric SMILES COc1cc2cn[nH]c2cc1c1ccc(c2c1ncc(c2N)C(=O)N)F
InChI InChI=1S/C18H14FN5O2/c1-26-14-4-8-6-23-24-13(8)5-10(14)9-2-3-12(19)15-16(20)11(18(21)25)7-22-17(9)15/h2-7H,1H3,(H2,20,22)(H2,21,25)(H,23,24)
1. Smith CR, Dougan DR, Komandla M, Kanouni T, Knight B, Lawson JD, Sabat M, Taylor ER, Vu P, Wyrick C. (2015)
Fragment-Based Discovery of a Small Molecule Inhibitor of Bruton's Tyrosine Kinase.
J Med Chem, 58 (14): 5437-44. [PMID:26087137]
2. Yao X, Sun X, Jin S, Yang L, Xu H, Rao Y. (2019)
Discovery of 4-Aminoquinoline-3-carboxamide Derivatives as Potent Reversible Bruton's Tyrosine Kinase Inhibitors for the Treatment of Rheumatoid Arthritis.
J Med Chem, 62 (14): 6561-6574. [PMID:31260299]