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benfluorex   Click here for help

GtoPdb Ligand ID: 14184

Synonyms: benfluramate | Mediator®
Approved drug
benfluorex is an approved drug
Compound class: Synthetic organic
Comment: Benfluorex has been reported to act as an hepatocyte nuclear receptor factor 4α (HNF4α) agonist [2].
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 3
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 38.33
Molecular weight 351.36
XLogP 3.3
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 CC(CC1=CC=CC(=C1)C(F)(F)F)NCCOC(=O)C2=CC=CC=C2
Isomeric SMILES CC(CC1=CC(=CC=C1)C(F)(F)F)NCCOC(=O)C2=CC=CC=C2
InChI InChI=1S/C19H20F3NO2/c1-14(12-15-6-5-9-17(13-15)19(20,21)22)23-10-11-25-18(24)16-7-3-2-4-8-16/h2-9,13-14,23H,10-12H2,1H3
InChI Key CJAVTWRYCDNHSM-UHFFFAOYSA-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
Approved drug? Yes.
Withdrawn drug? Yes
IUPAC Name Click here for help
2-[1-[3-(trifluoromethyl)phenyl]propan-2-ylamino]ethyl benzoate
International Nonproprietary Names Click here for help
INN number INN
3054 benfluorex
Synonyms Click here for help
benfluramate | Mediator®
Database Links Click here for help
CAS Registry No. 23602-78-0 (source: WHO INN record)
ChEBI CHEBI:93826
ChEMBL Ligand CHEMBL400599
DrugBank Ligand DB09022
PubChem CID 2318
Search Google for chemical match using the InChIKey CJAVTWRYCDNHSM-UHFFFAOYSA-N
Search Google for chemicals with the same backbone CJAVTWRYCDNHSM
Search PubMed clinical trials benfluorex
Search PubMed titles benfluorex
Search PubMed titles/abstracts benfluorex
UniChem Compound Search for chemical match using the InChIKey CJAVTWRYCDNHSM-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey CJAVTWRYCDNHSM-UHFFFAOYSA-N