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
SMILES / InChI / InChIKey
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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)
InChI Key PQGCMFVNJWTUFH-UHFFFAOYSA-N
Bioactivity Comments
The minimun inhibitory concentration for growth of MTB in vitro (MIC) was reported as 90 nM.
Selectivity at other protein targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
MTB polyketide synthase Pks13 Primary target of this compound TB Inhibitor Inhibition 6.7 pIC50 - 1
pIC50 6.7 (IC50 1.9x10-7 M) [1]