GNF2133   Click here for help

GtoPdb Ligand ID: 10687

Synonyms: compound 13g [PMID: 32077280] | GNF-2133
PDB Ligand
Compound class: Synthetic organic
Comment: GNF2133 is a potent, selective and orally bioavailable inhibitor of dual specificity tyrosine phosphorylation regulated kinase 1A (DYRK1A) [3]. It was designed and reported by the Genomics Institute of the Novartis Research Foundation (GNF). Inhibition of DYRK1A is being examined as a mechanism to promote β-cell proliferation as a novel therapy for type I diabetes. GNF2133 is active in relevant in vivo models. Significantly, GNF2133 is devoid of glycogen synthase kinase-3β (GSK3β) inhibitory activity, which is considered to be a potential long-term treatment liability of pre-exisitng dual DYRK1A/GSK3β inhibitors [1].
See also compound 2-2c [PMID: 32003560], which is a selective DYRK1A inhibitor with a different chemical scaffold [2].
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 75.52
Molecular weight 434.24
XLogP 2.02
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
Click here for help

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/)

✖
Canonical SMILES CCN1CCN(CC1)C(=O)Nc1nccc(c1)c1cn(c2c1ccnc2)C1CCOCC1
Isomeric SMILES CCN1CCN(CC1)C(=O)Nc1nccc(c1)c1cn(c2c1ccnc2)C1CCOCC1
InChI InChI=1S/C24H30N6O2/c1-2-28-9-11-29(12-10-28)24(31)27-23-15-18(3-8-26-23)21-17-30(19-5-13-32-14-6-19)22-16-25-7-4-20(21)22/h3-4,7-8,15-17,19H,2,5-6,9-14H2,1H3,(H,26,27,31)
InChI Key SAZIAQSVBIWIDU-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
4-Ethyl-N-(4-(1-(tetrahydro-2H-pyran-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)pyridin-2-yl)piperazine-1-carboxamide
Synonyms Click here for help
compound 13g [PMID: 32077280] | GNF-2133
Database Links Click here for help
GtoPdb PubChem SID 404859134
PubChem CID 145994392
RCSB PDB Ligand Q8J
Search Google for chemical match using the InChIKey SAZIAQSVBIWIDU-UHFFFAOYSA-N
Search Google for chemicals with the same backbone SAZIAQSVBIWIDU
UniChem Compound Search for chemical match using the InChIKey SAZIAQSVBIWIDU-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey SAZIAQSVBIWIDU-UHFFFAOYSA-N