ataluren   

GtoPdb Ligand ID: 7341

Synonyms: PTC124
ataluren is an approved drug (EMA (2014))
Compound class: Synthetic organic
Comment: Ataluren is a compound in an emerging class of chemicals which induce ribosomal readthrough. This developing pharmaceutical intervention has been termed 'readthrough strategy'. Clinically, this type of compound has potential benefit in the treatment of genetic disorders associated with loss of functional protein due to nonsense or PTC mutations, such as certain types of muscular dystrophy, cystic fibrosis and many cancers [1,4].
2D Structure

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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Click here for structure editor
Physico-chemical Properties

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 3
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 76.22
Molecular weight 284.06
XLogP 3.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey

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 Fc1ccccc1c1onc(n1)c1cccc(c1)C(=O)O
Isomeric SMILES Fc1ccccc1c1onc(n1)c1cccc(c1)C(=O)O
InChI InChI=1S/C15H9FN2O3/c16-12-7-2-1-6-11(12)14-17-13(18-21-14)9-4-3-5-10(8-9)15(19)20/h1-8H,(H,19,20)
InChI Key OOUGLTULBSNHNF-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (EMA (2014))
IUPAC Name
3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic acid
International Nonproprietary Names
INN number INN
8956 ataluren
Synonyms
PTC124
Database Links
CAS Registry No. 775304-57-9 (source: SciFinder)
ChEMBL Ligand CHEMBL256997
DrugCentral Ligand 4872
GtoPdb PubChem SID 178103913
PubChem CID 11219835
Search Google for chemical match using the InChIKey OOUGLTULBSNHNF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OOUGLTULBSNHNF
Search PubMed clinical trials ataluren
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Search UniChem for chemical match using the InChIKey OOUGLTULBSNHNF-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone OOUGLTULBSNHNF
Wikipedia Ataluren