compound 29 [Moslin et al., 2017]   Click here for help

GtoPdb Ligand ID: 9992

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Compound 29 binds to the JH2 pseudokinase domain of the Janus kinase family enzyme, TYK2 [1].
Various cytokines and their receptors mediate intracellular signalling through pairs of Janus kinase family enzymes. TYK2 dimerises with JAK2 to mediate IL-12 and IL-23 signalling (both are p40 subunit containing cytokines), and with JAK1 for the IFNα/β pathway. Both of these TYK2-dependent pathways are validated as druggable targets for the development of pharmaceuticals for the treatment of autoimmune diseases. Displacement of the ATP that binds to the JH2 pseudokinase domain allosterically disrupts TYK2 catalytic activity, in a mechanism that appears to stablise the kinase in an auto-inhibitory conformation. Expolting this domain is being investigated with the aim of identifying inhibitors with improved selectivity compared to traditional orthosteric JH1 domain ATP-competitive inhibitors.
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Ligand Activity Visualisation Charts

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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 CDK toolkit. 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 5
Rotatable bonds 10
Topological polar surface area 133.04
Molecular weight 450.18
XLogP 1.49
No. Lipinski's rules broken 0
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.

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Canonical SMILES COc1c(cc(cc1F)F)Nc1cc(NC)c2n(n1)c(cn2)C(=O)NCCC(CO)(O)C
Isomeric SMILES COc1c(cc(cc1F)F)Nc1cc(NC)c2n(n1)c(cn2)C(=O)NCCC(CO)(O)C
InChI InChI=1S/C20H24F2N6O4/c1-20(31,10-29)4-5-24-19(30)15-9-25-18-14(23-2)8-16(27-28(15)18)26-13-7-11(21)6-12(22)17(13)32-3/h6-9,23,29,31H,4-5,10H2,1-3H3,(H,24,30)(H,26,27)
InChI Key BDYFCJQKSYBTAK-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-[(3,5-difluoro-2-methoxyphenyl)amino]-N-(3,4-dihydroxy-3-methylbutyl)-8-(methylamino)imidazo[1,2-b]pyridazine-3-carboxamide
Database Links Click here for help
GtoPdb PubChem SID 374883879
PubChem CID 134611892
Search Google for chemical match using the InChIKey BDYFCJQKSYBTAK-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BDYFCJQKSYBTAK
UniChem Compound Search for chemical match using the InChIKey BDYFCJQKSYBTAK-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BDYFCJQKSYBTAK-UHFFFAOYSA-N