compound 5 [Stecula et al., 2020]   Click here for help

GtoPdb Ligand ID: 11155

Synonyms: MCULE-2879769428
Compound class: Synthetic organic
Comment: Compound 5 was reported as a low-molecular-weight inhibitor of the Helicobacter pylori protein flavodoxin, with antibacterial activity against this pathogen, in 2013 [1]. A 2020 report by Stecula et al. found that compound 5 inhibits the novel disease target aspartate N-acetyltransferase (ANAT; NAT8L), and that 5 offers a tool compound, with a suitably drug-like scaffold, for studying ANAT inhibition as a therapeutic approach in Canavan disease [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 136.34
Molecular weight 412.96
XLogP 6.23
No. Lipinski's rules broken 1
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Canonical SMILES Clc1ccc(c(c1)Cl)C(=O)OCCSc1ccc(c2c1non2)N(=O)=O
Isomeric SMILES Clc1ccc(c(c1)Cl)C(=O)OCCSc1ccc(c2c1non2)N(=O)=O
InChI InChI=1S/C15H9Cl2N3O5S/c16-8-1-2-9(10(17)7-8)15(21)24-5-6-26-12-4-3-11(20(22)23)13-14(12)19-25-18-13/h1-4,7H,5-6H2
1. Galano JJ, Alías M, Pérez R, Velázquez-Campoy A, Hoffman PS, Sancho J. (2013)
Improved flavodoxin inhibitors with potential therapeutic effects against Helicobacter pylori infection.
J Med Chem, 56 (15): 6248-58. [PMID:23841482]
2. Stecula A, Hussain MS, Viola RE. (2020)
Discovery of Novel Inhibitors of a Critical Brain Enzyme Using a Homology Model and a Deep Convolutional Neural Network.
Journal of Medicinal Chemistry, [Epub ahead of print]. DOI: 10.1021/acs.jmedchem.0c00473