TBA-354   Click here for help

GtoPdb Ligand ID: 13546

Compound class: Synthetic organic
Comment: TBA-354 is a nitroimidazole-based antibacterial compound derived from pretomanid (PA-824) [1]. It has narrow-spectrum activity, inhibiting Mycobacterium tuberculosis and Mycobacterium bovis but not nontuberculous mycobacteria (NTM) or the Gram-positive and Gram-negative bacteria tested [2]. TBA-354 was under clinical development for the treatment of tuberculosis (TB), by the non-profit organisation TB Alliance (www.tballiance.org.za), but was discontinued in 2016 [3].

TBA-354 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 6
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 98.79
Molecular weight 436.34
XLogP 2.35
No. Lipinski's rules broken 0

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 C1=C(C=NC(=C1)C2=CC=C(C=C2)OC(F)(F)F)CO[C@H]3CN4C=C(N=C4OC3)[N+](=O)[O-]
Isomeric SMILES C1[C@@H](COC2=NC(=CN21)[N+](=O)[O-])OCC3=CN=C(C=C3)C4=CC=C(C=C4)OC(F)(F)F
InChI InChI=1S/C19H15F3N4O5/c20-19(21,22)31-14-4-2-13(3-5-14)16-6-1-12(7-23-16)10-29-15-8-25-9-17(26(27)28)24-18(25)30-11-15/h1-7,9,15H,8,10-11H2/t15-/m0/s1
InChI Key ZXSGSFMORAILEY-HNNXBMFYSA-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-({[(6S)-2-nitro-5H,6H,7H-imidazo[2,1-b][1,3]oxazin-6-yl]oxy}methyl)-2-[4-(trifluoromethoxy)phenyl]pyridine
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo TBA-354
Other databases
ChEMBL Ligand CHEMBL1630563
GtoPdb PubChem SID 500839956
PubChem CID 49836057
Search Google for chemical match using the InChIKey ZXSGSFMORAILEY-HNNXBMFYSA-N
Search Google for chemicals with the same backbone ZXSGSFMORAILEY
UniChem Compound Search for chemical match using the InChIKey ZXSGSFMORAILEY-HNNXBMFYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZXSGSFMORAILEY-HNNXBMFYSA-N

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MedChemExpress
TBA-354 (links to external site)
Cat. No. HY-12485