compound 1 [PMID: 28611375]   Click here for help

GtoPdb Ligand ID: 9673

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: 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.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 69.31
Molecular weight 497.15
XLogP 4.79
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(N1CCN(CC1)Cc1ccccc1)CN(S(=O)(=O)c1ccccc1)c1cccc(c1C)Cl
Isomeric SMILES O=C(N1CCN(CC1)Cc1ccccc1)CN(S(=O)(=O)c1ccccc1)c1cccc(c1C)Cl
InChI InChI=1S/C26H28ClN3O3S/c1-21-24(27)13-8-14-25(21)30(34(32,33)23-11-6-3-7-12-23)20-26(31)29-17-15-28(16-18-29)19-22-9-4-2-5-10-22/h2-14H,15-20H2,1H3
InChI Key QTYHUADZOPIUME-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-(3-chloro-2-methylphenyl)-N-[2-oxo-2-[4-(phenylmethyl)piperazin-1-yl]ethyl]benzenesulfonamide
Database Links Click here for help
GtoPdb PubChem SID 348353632
PubChem CID 2898484
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