TBI-166   Click here for help

GtoPdb Ligand ID: 12961

Synonyms: pyrifazimine
Compound class: Synthetic organic
Comment: TBI-166 is a riminophenazine class antimycobacterial compound and an analogue of clofazimine [1]. TBI-166 has advanced to clinical evaluation for the treatment of tuberculosis.
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 8
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 80.04
Molecular weight 589.61
XLogP 4.83
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 COC1CCC(CC1)N=C2C=C3C(=NC4=C(C=CC=C4)N3C5=CC=C(C=C5)OC(F)(F)F)C=C2NC6=CC=CN=C6OC
Isomeric SMILES COC1CCC(CC1)N=C2C=C3C(=NC4=CC=CC=C4N3C5=CC=C(C=C5)OC(F)(F)F)C=C2NC6=C(N=CC=C6)OC
InChI InChI=1S/C32H30F3N5O3/c1-41-22-13-9-20(10-14-22)37-27-19-30-28(18-26(27)39-25-7-5-17-36-31(25)42-2)38-24-6-3-4-8-29(24)40(30)21-11-15-23(16-12-21)43-32(33,34)35/h3-8,11-12,15-20,22,39H,9-10,13-14H2,1-2H3
InChI Key GUSGYHIQYWRCQO-UHFFFAOYSA-N
Bioactivity Comments
The MIC for antimycobacterial activity in vitro is 0.016 μg/ml against Mycobacterium tuberculosis H37Rv and 0.027-0.095 μg/ml against a panel of drug-resistant M. tuberculosis clinical isolates [1]. In vivo testing in mice has shown that the drug causes less skin discoloration than clofazimine [2].