JNJ-7706621   Click here for help

GtoPdb Ligand ID: 5932

Synonyms: aurora kinase/Cdk inhibitor | JNJ7706621
PDB Ligand
Compound class: Synthetic organic
Comment: JNJ-7706621 was originally identified as a pan-CDK and Aurora A/B kinase inhibitor [5]. JNJ-7706621 binding to the pseudo (JH2) kinase domain of Janus kinase 2 has been reported more recently [7]. This mechanism of JAK inhibition is viewed as offering a potentially novel pharmacological modality as an alternative to targeting the active kinase (JH1) domain and its ATP binding pocket.
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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.

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View interactive charts of activity data across species
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 3
Rotatable bonds 5
Topological polar surface area 154.37
Molecular weight 394.07
XLogP 1.8
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 Fc1cccc(c1C(=O)n1nc(nc1N)Nc1ccc(cc1)S(=O)(=O)N)F
Isomeric SMILES Fc1cccc(c1C(=O)n1nc(nc1N)Nc1ccc(cc1)S(=O)(=O)N)F
InChI InChI=1S/C15H12F2N6O3S/c16-10-2-1-3-11(17)12(10)13(24)23-14(18)21-15(22-23)20-8-4-6-9(7-5-8)27(19,25)26/h1-7H,(H2,19,25,26)(H3,18,20,21,22)
InChI Key KDKUVYLMPJIGKA-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
Note that some bioactivity data for this compound may be associated with the acetonitrile compound (PubChem CID 16760303).
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Janus kinase 2 Hs Inhibitor Binding 6.3 pKd - 6-7
⤷ pKd 6.3 (Kd 4.6x10-7 M) [7]
Description: Binding affinity for JAK2 JH2 pseudokinase domain
pKd 6.3 (Kd 4.56x10-7 M) [6]
Description: Affinity for JAK2 JH2 by competitive fluorescence polarization (FP) assay
cyclin dependent kinase 2 Hs Inhibitor Inhibition 8.7 pIC50 - 5
⤷ pIC50 8.7 (IC50 2x10-9 M) [5]
Description: CDK2 in association with cyclin A
cyclin dependent kinase 1 Hs Inhibitor Inhibition 8.2 pIC50 - 5
⤷ pIC50 8.2 (IC50 6.4x10-9 M) [5]
Description: CDK1 in association with cyclin B
aurora kinase B Hs Inhibitor Inhibition 7.9 pIC50 - 4
⤷ pIC50 7.9 (IC50 1.3x10-8 M) [4]
aurora kinase A Hs Inhibitor Inhibition 7.7 pIC50 - 4
⤷ pIC50 7.7 (IC50 1.8x10-8 M) [4]
Janus kinase 2 Hs Inhibitor Inhibition 7.0 pIC50 - 7
⤷ pIC50 7.0 (IC50 1.06x10-7 M) [7]
Description: Binding to the JH2 pseudo kinase domain of JAK2 was determined using isothermal titration calorimetry (ITC).