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zecontimod   Click here for help

GtoPdb Ligand ID: 14370

Synonyms: compound I-33 [US20220081429]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: The chemical structure for this compound was obtained from WHO INN proposed list 134 (Feb 2026) in which it is desribed as an immunomodulator. The structure is claimed in patent US20220081429 (Artax Biopharma) as an inhibitor of the protein-protein interaction between the CD3 component of the T cell receptor (TCR) and non-catalytic (SH3.1) region of tyrosine kinase adaptor protein (Nck; NCK1, NCK2) [1]. This mechanism is proposed to modulate TCR activation driven by weak avidity self antigens in autoimmune diseases [2]. Artax Biopharma's only disclosed candidate in this class is AX-158, so we surmise that zecontimod is the INN match for AX-158.
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 5
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 59
Molecular weight 397.44
XLogP 1.82
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 C1CCN(C1)CC2=C(C3=CC=C(C=C3)F)C4=C(C=CC(=C4)OCCC(=O)O)OC2
Isomeric SMILES FC1=CC=C(C=C1)C2=C(COC3=C2C=C(C=C3)OCCC(=O)O)CN4CCCC4
InChI InChI=1S/C23H24FNO4/c24-18-5-3-16(4-6-18)23-17(14-25-10-1-2-11-25)15-29-21-8-7-19(13-20(21)23)28-12-9-22(26)27/h3-8,13H,1-2,9-12,14-15H2,(H,26,27)
InChI Key XXARLKNSPVBUSQ-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/)
Bioactivity Comments
Zecontimod competitively inhibits the CD3F-Nck1 interaction in vitro, in a biosensor based assay [1].