Compound ID | 2704

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Compound with N-[2-(2-chlorophenoxy)ethyl]aniline core

Class: Small molecule antibacterial agent

Spectrum of activity: Gram-positive
Details of activity: Active against Staphylococcus aureus; dissipates proton motive force
Propensity to select resistant mutants: Yes, low (10^-8 frequency after 30 days)
Description: A result of deep-learning model prediction of structural class with selective antibiotic activity (deep learning approach); >8-fold selectivity (human cell IC50 vs MIC); compound 1 - link to structure (1); compound 2 - link to structure (2)
Institute where first reported: Infectious Disease and Microbiome Program, Broad Institute of MIT and Harvard, Cambridge, MA, USA; Department of Biochemistry and Biomedical Sciences, Michael G. DeGroote Institute for Infectious Disease Research and David Braley Centre for Antibiotic Discovery, McMaster University, Hamilton, Ontario, Canada
Year first mentioned: 2023
Development status: Experimental
Chemical structure(s):
5-Bromo-2-[2-(2,4-dichloro-phenoxy)-acetylamino]-benzoic acid Compound 2
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Molecular weight: 419.05
Iso. SMILES: C1=CC(=C(C=C1Cl)Cl)OCC(=O)NC2=C(C=C(C=C2)Br)C(=O)O
InChI Key: ANWNQBQGJVQITO-UHFFFAOYSA-N
Can. SMILES: C1=C(C=C(C(=C1)NC(=O)COC2=CC=C(C=C2Cl)Cl)C(=O)O)Br
InChI: InChI=1S/C15H10BrCl2NO4/c16-8-1-3-12(10(5-8)15(21)22)19-14(20)7-23-13-4-2-9(17)6-11(13)18/h1-6H,7H2,(H,19,20)(H,21,22)
4-Chloro-2-{[(2,4-dichlorophenoxy)acetyl]amino}benzoic acid Compound 1
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Molecular weight: 374.6
Iso. SMILES: C1=CC(=C(C=C1Cl)NC(=O)COC2=C(C=C(C=C2)Cl)Cl)C(=O)O
InChI Key: KKKPLTVKYNLFCJ-UHFFFAOYSA-N
Can. SMILES: C1=C(C=C(C(=C1)C(=O)O)NC(=O)COC2=CC=C(C=C2Cl)Cl)Cl
InChI: InChI=1S/C15H10Cl3NO4/c16-8-2-4-13(11(18)5-8)23-7-14(20)19-12-6-9(17)1-3-10(12)15(21)22/h1-6H,7H2,(H,19,20)(H,21,22)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/1314498
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/2942818
Citation: https://www.nature.com/articles/s41586-023-06887-8#Sec10

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