compound 1 [PMID: 28611375]

Ligand id: 9673

Name: compound 1 [PMID: 28611375]

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 69.31
Molecular weight 497.15
XLogP 6.13
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
N-(3-chloro-2-methylphenyl)-N-[2-oxo-2-[4-(phenylmethyl)piperazin-1-yl]ethyl]benzenesulfonamide
Database Links
GtoPdb PubChem SID 348353632
PubChem CID 2898484
Search Google for chemical match using the InChIKey QTYHUADZOPIUME-UHFFFAOYSA-N
Search Google for chemicals with the same backbone QTYHUADZOPIUME
Search UniChem for chemical match using the InChIKey QTYHUADZOPIUME-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone QTYHUADZOPIUME
Comments
Compound 1 is reported as a direct inhibitor of the protein-protein interaction between TNFα and both of its receptors (TNFRI and TNFRII) [1]. The compound is orally active, which is in contrast to the TNFα biologics that are already in clinical use e.g. infliximab, adalimumab and etanercept. Compound 1 interacts with TNFα in a two-site binding mode with a high affinity site (nM) and a low affinity site (μM) detected [1]. This mechanism interferes with TNFα homotrimer (bioactive cytokine) formation, and thereby inhibits TNF receptor activation. The physicochemical properties of compound 1 are not optimal (especially wrt solubility), so some medicinal chemistry effort would need to be applied to create a more efficient drug-like molecule.