TBAJ-587   Click here for help

GtoPdb Ligand ID: 13060

Synonyms: compound 8 [PMID: 30803745]
PDB Ligand
Compound class: Synthetic organic
Comment: TBAJ-587, an analogue of bedaquiline, was discovered at the University of Auckland following a lead optimization programme to identify novel members of the diarylquinolines class of antibacterial compounds [2]. TBAJ-587 has a more favourable ADME profile, lower risk of QT prolongation, and more potent antimycobacterial activity than bedaquiline [2].
See also our entry for TBAJ-876 that was identified in the same study.

TBAJ-587 is commercially available from our sponsors

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 8
Hydrogen bond donors 1
Rotatable bonds 11
Topological polar surface area 85.11
Molecular weight 614.5
XLogP 1.55
No. Lipinski's rules broken 2

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=CC=CC(=C2F)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=C(C(=CC=C2)OC)F)C3=C(N=C4C=CC(=CC4=C3)Br)OC)O
InChI InChI=1S/C30H33BrFN3O5/c1-35(2)13-12-30(36,19-16-25(38-4)34-26(17-19)39-5)27(21-8-7-9-24(37-3)28(21)32)22-15-18-14-20(31)10-11-23(18)33-29(22)40-6/h7-11,14-17,27,36H,12-13H2,1-6H3/t27-,30-/m1/s1
InChI Key JJEGOJPMKLRSPJ-POURPWNDSA-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/)
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel