CRS3123   Click here for help

GtoPdb Ligand ID: 10991

Synonyms: CRS-3123 | REP-3123 | REP3123
PDB Ligand
Compound class: Synthetic organic
Comment: CRS3123 is an orally bioactive, diaryldiamine compound that inhibits bacterial methionyl-tRNA synthetases in Gram-positive bacteria [1]. It has limited antibacterial activity against normal anaerobic gut flora (e.g. Clostridium ramosum, bifidobacteria, lactobacilli of the Lactobacillus casei-rhamnosus-plantarum group) and Gram-negative anaerobes.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 94.39
Molecular weight 510.96
XLogP 6.05
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES Brc1cc(Br)c2c(c1)[C@H](NCCCNc1cc(=O)c3c([nH]1)ccs3)CCO2
Isomeric SMILES Brc1cc(Br)c2c(c1)[C@H](NCCCNc1cc(=O)c3c([nH]1)ccs3)CCO2
InChI InChI=1S/C19H19Br2N3O2S/c20-11-8-12-14(2-6-26-18(12)13(21)9-11)22-4-1-5-23-17-10-16(25)19-15(24-17)3-7-27-19/h3,7-10,14,22H,1-2,4-6H2,(H2,23,24,25)/t14-/m1/s1
InChI Key NNTYBKTXMKBRFA-CQSZACIVSA-N
References
1. Citron DM, Warren YA, Tyrrell KL, Merriam V, Goldstein EJ. (2009)
Comparative in vitro activity of REP3123 against Clostridium difficile and other anaerobic intestinal bacteria.
J Antimicrob Chemother, 63 (5): 972-6. [PMID:19240076]
2. Lomeli BK, Galbraith H, Schettler J, Saviolakis GA, El-Amin W, Osborn B, Ravel J, Hazleton K, Lozupone CA, Evans RJ et al.. (2019)
Multiple-Ascending-Dose Phase 1 Clinical Study of the Safety, Tolerability, and Pharmacokinetics of CRS3123, a Narrow-Spectrum Agent with Minimal Disruption of Normal Gut Microbiota.
Antimicrob Agents Chemother, 64 (1). [PMID:31685472]
3. Nayak SU, Griffiss JM, Blumer J, O'Riordan MA, Gray W, McKenzie R, Jurao RA, An AT, Le M, Bell SJ et al.. (2017)
Safety, Tolerability, Systemic Exposure, and Metabolism of CRS3123, a Methionyl-tRNA Synthetase Inhibitor Developed for Treatment of Clostridium difficile, in a Phase 1 Study.
Antimicrob Agents Chemother, 61 (8). DOI: 10.1128/AAC.02760-16 [PMID:28584140]