ezutromid   Click here for help

GtoPdb Ligand ID: 11110

Synonyms: 5-ethylsulfonyl-NBO | SMT C1100 | SMTC 1100 | SMTC1100
Compound class: Synthetic organic
Comment: Ezutromid (SMT C1100) is a clinical stage compound that was developed for its ability to increase expression of utrophin (UTRN; P46939), as a substitute for missing the dystrophin (DMD; P11532) in Duchenne muscular dystrophy (DMD) patients [1]. It is orally active. The aryl hydrocarbon receptor (AhR) has been reported as a molecular target for ezutromid, with ezutromid behaving as an AhR antagonist [2]. Ezutromid and other AhR antagonists up-regulate utrophin, adding to the proposition that this pathway offers disease-modifying potential for DMD.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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 3
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 68.55
Molecular weight 337.08
XLogP 4.3
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 CCS(=O)(=O)c1ccc2c(c1)nc(o2)c1ccc2c(c1)cccc2
Isomeric SMILES CCS(=O)(=O)c1ccc2c(c1)nc(o2)c1ccc2c(c1)cccc2
InChI InChI=1S/C19H15NO3S/c1-2-24(21,22)16-9-10-18-17(12-16)20-19(23-18)15-8-7-13-5-3-4-6-14(13)11-15/h3-12H,2H2,1H3
InChI Key KSGCNXAZROJSNW-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-ethylsulfonyl-2-naphthalen-2-yl-1,3-benzoxazole
International Nonproprietary Names Click here for help
INN number INN
10163 ezutromid
Synonyms Click here for help
5-ethylsulfonyl-NBO | SMT C1100 | SMTC 1100 | SMTC1100
Database Links Click here for help
CAS Registry No. 945531-77-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL1773683
DrugBank Ligand DB12888
GtoPdb PubChem SID 434122170
PubChem CID 25109292
Search Google for chemical match using the InChIKey KSGCNXAZROJSNW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KSGCNXAZROJSNW
Search PubMed clinical trials ezutromid
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Search PubMed titles/abstracts ezutromid
UniChem Compound Search for chemical match using the InChIKey KSGCNXAZROJSNW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KSGCNXAZROJSNW-UHFFFAOYSA-N