TBAJ-876   Click here for help

GtoPdb Ligand ID: 13132

Synonyms: compound 46 [PMID: 30803745]
PDB Ligand
Compound class: Synthetic organic
Comment: TBAJ-876, an analogue of bedaquiline, was discovered at the University of Auckland following a lead optimization project to identify novel members of the diarylquinolines class of antibacterial compounds [3]. TBAJ-876 has a more favourable ADME profile, lower risk of QT prolongation, and more potent antimycobacterial activity than bedaquiline [3].
See also our entry for TBAJ-587 that was identified in the same study.
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 11
Hydrogen bond donors 1
Rotatable bonds 13
Topological polar surface area 115.93
Molecular weight 657.55
XLogP 0.94
No. Lipinski's rules broken 3

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 CN(C)CC[C@@](C1=CC(=NC(=C1)OC)OC)([C@H](C2=C(C(=NC(=C2)OC)OC)OC)C3=C(N=C4C=CC(=CC4=C3)Br)OC)O
Isomeric SMILES CN(C)CC[C@@](C1=CC(=NC(=C1)OC)OC)([C@H](C2=CC(=NC(=C2OC)OC)OC)C3=C(N=C4C=CC(=CC4=C3)Br)OC)O
InChI InChI=1S/C31H37BrN4O7/c1-36(2)12-11-31(37,19-15-24(38-3)34-25(16-19)39-4)27(21-17-26(40-5)35-30(43-8)28(21)41-6)22-14-18-13-20(32)9-10-23(18)33-29(22)42-7/h9-10,13-17,27,37H,11-12H2,1-8H3/t27-,31-/m1/s1
InChI Key HHDDKDPLFXIPBX-DLFZDVPBSA-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
(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-2-(2,6-dimethoxypyridin-4-yl)-4-(dimethylamino)-1-(2,3,6-trimethoxypyridin-4-yl)butan-2-ol
Synonyms Click here for help
compound 46 [PMID: 30803745]
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo TBAJ-876
Other databases
BindingDB Ligand 50537234
CAS Registry No. 2332841-25-3 (source: Scifinder)
ChEMBL Ligand CHEMBL4553146
GtoPdb PubChem SID 491299914
PubChem CID 155510360
RCSB PDB Ligand YGR
Search Google for chemical match using the InChIKey HHDDKDPLFXIPBX-DLFZDVPBSA-N
Search Google for chemicals with the same backbone HHDDKDPLFXIPBX
UniChem Compound Search for chemical match using the InChIKey HHDDKDPLFXIPBX-DLFZDVPBSA-N
UniChem Connectivity Search for chemical match using the InChIKey HHDDKDPLFXIPBX-DLFZDVPBSA-N