compound 23 [PMID: 31398032]   Click here for help

GtoPdb Ligand ID: 10445

Compound class: Synthetic organic
Comment: Compound 23 the most potent inhibitor of the bromodomain-containing enzyme ATAD2 to be identified using a specially designed high-throughput screening and hit qualification process [1]. The compound exhibits a novel binding mode for bromodomain inhibitors that includes displacement of all of the conserved water molecules, and formation of a halogen-bonding interaction, within the active site.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 124.27
Molecular weight 512.07
XLogP 1.69
No. Lipinski's rules broken 0
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Canonical SMILES O=C(CN1C(=O)NC(C1=O)(C)C1CC1)Nc1ccc(c(c1)S(=O)(=O)N1CCCCC1)Br
Isomeric SMILES O=C(CN1C(=O)NC(C1=O)(C)C1CC1)Nc1ccc(c(c1)S(=O)(=O)N1CCCCC1)Br
InChI InChI=1S/C20H25BrN4O5S/c1-20(13-5-6-13)18(27)25(19(28)23-20)12-17(26)22-14-7-8-15(21)16(11-14)31(29,30)24-9-3-2-4-10-24/h7-8,11,13H,2-6,9-10,12H2,1H3,(H,22,26)(H,23,28)
1. Bamborough P, Chung CW, Demont EH, Bridges AM, Craggs PD, Dixon DP, Francis P, Furze RC, Grandi P, Jones EJ et al.. (2019)
A Qualified Success: Discovery of a New Series of ATAD2 Bromodomain Inhibitors with a Novel Binding Mode Using High-Throughput Screening and Hit Qualification.
J Med Chem, 62 (16): 7506-7525. [PMID:31398032]