balinatunfib   Click here for help

GtoPdb Ligand ID: 13583

Synonyms: SAR-441566 | SAR441566
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: SAR441566 is a small molecule that binds to TNF and disrupts signalling [2]. The chemical structure is claimed in UCB Biopharma/Sanofi patent WO2016050975A1 [1] and is a match for the INN balinatunfib (from INN proposed list 131, Aug. 2024). Mechanistically, balinatunfib/SAR441566 stabilises the TNF trimer in an inactive conformation [2]. It has been proposed as an orally available alternative to deliver the same therapeutic outcome as anti-TNF biologics in chronic autoimmune diseases.

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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 8
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 95.88
Molecular weight 502.52
XLogP 0.95
No. Lipinski's rules broken 1

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 CN1[C@@H]2C[C@H](C3=C(C=CC=C3C1=O)OC(F)F)N4C5=C(C=CC(=C5)C6=CN=C(C7(CCC7)N)N=C6)N=C24
Isomeric SMILES CN1[C@@H]2C[C@H](C3=C(C1=O)C=CC=C3OC(F)F)N4C2=NC5=C4C=C(C=C5)C6=CN=C(N=C6)C7(CCC7)N
InChI InChI=1S/C27H24F2N6O2/c1-34-20-11-19(22-16(24(34)36)4-2-5-21(22)37-26(28)29)35-18-10-14(6-7-17(18)33-23(20)35)15-12-31-25(32-13-15)27(30)8-3-9-27/h2,4-7,10,12-13,19-20,26H,3,8-9,11,30H2,1H3/t19-,20-/m1/s1
InChI Key UROFXMLQPAUCGV-WOJBJXKFSA-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/)
Selectivity at ligand targets
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
tumour necrosis factor shed form Hs Inhibitor Binding 7.8 pKd - 2
⤷ pKd 7.8 (Kd 1.51x10-8 M) [2]
Description: Binding affinity for immobilised hTNF determined by SPR