AX-024   Click here for help

GtoPdb Ligand ID: 11253

Synonyms: AX-24 [2] | AX024
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AX-024 is a novel T cell modulator, that acts by disrupting the protein-protein interaction between CD3ε (a subunit in the T-cell receptor, TCR) and Nck, which causes a conformational change that prevents TCR activation [1-2]. It was developed by Artax Biopharma and seems to be a predecessor of their autoimmune clinical lead AX-158 (structure not disclosed).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 21.7
Molecular weight 339.16
XLogP 4.04
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES COc1ccc2c(c1)C(=C(CO2)CN1CCCC1)c1ccc(cc1)F
Isomeric SMILES COc1ccc2c(c1)C(=C(CO2)CN1CCCC1)c1ccc(cc1)F
InChI InChI=1S/C21H22FNO2/c1-24-18-8-9-20-19(12-18)21(15-4-6-17(22)7-5-15)16(14-25-20)13-23-10-2-3-11-23/h4-9,12H,2-3,10-11,13-14H2,1H3
1. Borroto A, Reyes-Garau D, Jiménez MA, Carrasco E, Moreno B, Martínez-Pasamar S, Cortés JR, Perona A, Abia D, Blanco S et al.. (2016)
First-in-class inhibitor of the T cell receptor for the treatment of autoimmune diseases.
Sci Transl Med, 8 (370): 370ra184. [PMID:28003549]
2. Gagete Mateos A, Castro Palomino J, Clauzel LM, Tormo Carulla D. (2015)
Chromene derivatives substituted by alkoxide as inhibitors of the tcr-nck interaction.
Patent number: WO2015056085A1. Assignee: rtax Biopharma Inc. Priority date: 18/10/2013. Publication date: 23/04/2015.