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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[3-[[(4R)-6,8-dibromo-3,4-dihydro-2H-chromen-4-yl]amino]propylamino]-4H-thieno[3,2-b]pyridin-7-one
Synonyms Click here for help
CRS-3123 | REP-3123 | REP3123
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo CRS3123
Other databases
CAS Registry No. 1013915-71-3 (source: ChemIDplus)
ChEMBL Ligand CHEMBL4297370
DrugBank Ligand DB12262
GtoPdb PubChem SID 405560432
PubChem CID 16744283
RCSB PDB Ligand U81
Search Google for chemical match using the InChIKey NNTYBKTXMKBRFA-CQSZACIVSA-N
Search Google for chemicals with the same backbone NNTYBKTXMKBRFA
UniChem Compound Search for chemical match using the InChIKey NNTYBKTXMKBRFA-CQSZACIVSA-N
UniChem Connectivity Search for chemical match using the InChIKey NNTYBKTXMKBRFA-CQSZACIVSA-N