ethionamide   Click here for help

GtoPdb Ligand ID: 12954

Synonyms: 1314 TH | Bayer 5312 | Trecator®
Approved drug PDB Ligand
ethionamide is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Ethionamide is a thioamide compound with potent antibacterial activity against mycobacteria. It is a prodrug that requires intracellular activation, by the monooxygenase EthA, in Mycobacterium tuberculosis [1]. Ethionamide is used in the treatment of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB).
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 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 70.47
Molecular weight 166.24
XLogP -0.23
No. Lipinski's rules broken 0
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 CCC1=CC(=CC=N1)C(=S)N
Isomeric SMILES CCC1=NC=CC(=C1)C(=S)N
InChI InChI=1S/C8H10N2S/c1-2-7-5-6(8(9)11)3-4-10-7/h3-5H,2H2,1H3,(H2,9,11)
InChI Key AEOCXXJPGCBFJA-UHFFFAOYSA-N
References
1. Fraaije MW, Kamerbeek NM, Heidekamp AJ, Fortin R, Janssen DB. (2004)
The prodrug activator EtaA from Mycobacterium tuberculosis is a Baeyer-Villiger monooxygenase.
J Biol Chem, 279 (5): 3354-60. [PMID:14610090]
2. Rastogi N, Labrousse V, Goh KS. (1996)
In vitro activities of fourteen antimicrobial agents against drug susceptible and resistant clinical isolates of Mycobacterium tuberculosis and comparative intracellular activities against the virulent H37Rv strain in human macrophages.
Curr Microbiol, 33 (3): 167-75. [PMID:8672093]