compound 17 [PMID: 23642479]   Click here for help

GtoPdb Ligand ID: 8161

Compound class: Synthetic organic
Comment: Compound 17 is one analogue of a medicinal chemistry set designed to identify novel small-molecule inhibitors of the cdc2-like (CLK) and dual specificity tyrosine phosphorylation-regulated (DYRK) kinases [1]. This set of analogues also includes ML315.
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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 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 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 56.27
Molecular weight 373.04
XLogP 4.58
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 Clc1cc(CNc2nccc(n2)c2ccc3c(c2)OCO3)cc(c1)Cl
Isomeric SMILES Clc1cc(CNc2nccc(n2)c2ccc3c(c2)OCO3)cc(c1)Cl
InChI InChI=1S/C18H13Cl2N3O2/c19-13-5-11(6-14(20)8-13)9-22-18-21-4-3-15(23-18)12-1-2-16-17(7-12)25-10-24-16/h1-8H,9-10H2,(H,21,22,23)
InChI Key FFJGYBJUQCZAAY-UHFFFAOYSA-N
Bioactivity Comments
Compound 17 has similar potency across CLK1, -2, and -4, and DYRK1A and -1B. It has no inhibitory effect on CLK3 [1]. We tag CLK1 as primary target for data metrics purposes, and this is not intended to indicate 'sole' target activity in this case.
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CDC like kinase 1 Primary target of this compound Hs Inhibitor Inhibition 8.7 pIC50 - 1
⤷ pIC50 8.7 (IC50 2x10-9 M) [1]
CDC like kinase 4 Hs Inhibitor Inhibition 8.4 pIC50 - 1
⤷ pIC50 8.4 (IC50 4x10-9 M) [1]
dual specificity tyrosine phosphorylation regulated kinase 1A Hs Inhibitor Inhibition 8.4 pIC50 - 1
⤷ pIC50 8.4 (IC50 4x10-9 M) [1]
dual specificity tyrosine phosphorylation regulated kinase 1B Hs Inhibitor Inhibition 8.1 pIC50 - 1
⤷ pIC50 8.1 (IC50 7x10-9 M) [1]
CDC like kinase 2 Hs Inhibitor Inhibition 7.6 pIC50 - 1
⤷ pIC50 7.6 (IC50 2.3x10-8 M) [1]