TAM16   Click here for help

GtoPdb Ligand ID: 9645

PDB Ligand
Compound class: Synthetic organic
Comment: TAM16 is a benzofuran inhibitor of MTB Pks13 with potent in vitro bactericidal activity against drug-susceptible and drug-resistant clinical isolates of M. tuberculosis. In multiple mouse infection models it showed in vivo efficacy equal to the first-line TB drug isoniazid [1]. There is PDB structure 5V3Y and the compound is example 32 in [2]. Analogues are exemplified with activity data (with some gaps).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 85.94
Molecular weight 380.17
XLogP 3.14
No. Lipinski's rules broken 0
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Canonical SMILES CNC(=O)c1c(oc2c1c(CN1CCCCC1)c(cc2)O)c1ccc(cc1)O
Isomeric SMILES CNC(=O)c1c(oc2c1c(CN1CCCCC1)c(cc2)O)c1ccc(cc1)O
InChI InChI=1S/C22H24N2O4/c1-23-22(27)20-19-16(13-24-11-3-2-4-12-24)17(26)9-10-18(19)28-21(20)14-5-7-15(25)8-6-14/h5-10,25-26H,2-4,11-13H2,1H3,(H,23,27)
1. Aggarwal A, Parai MK, Shetty N, Wallis D, Woolhiser L, Hastings C, Dutta NK, Galaviz S, Dhakal RC, Shrestha R et al.. (2017)
Development of a Novel Lead that Targets M. tuberculosis Polyketide Synthase 13.
Cell, 170 (2): 249-259.e25. [PMID:28669536]
2. Sacchettini, et al.. (2016)
Substituted benzofuran derivatives as novel antimycobacterial agents.
Patent number: WO2016172498. Assignee: Texas A&M University. Priority date: 17/08/2017. Publication date: 27/10/2016.