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Compound Detail

CHEMBL4292553

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Oc1ccc(-c2cnc3[nH]cc(-c4ccc(F)cc4)c3c2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4292553
Phase Preclinical
Structure Type MOL
InChI Key IRJDHVRCNAUAOH-UHFFFAOYSA-N
8
Targets
15
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

320.3
MW (Da)
4.45
ALogP
3
HBA
3
HBD
69.1
PSA (Ų)
0.48
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H13FN2O2
MW 320.32
Aromatic Rings 4
Heavy Atoms 24
NP-Likeness -0.26

Activity Summary

IC50 13 meas. best 8.03
Kd 2 meas. best 7.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 IC50 8.03 7.675 9.4 2
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL5508
 IC50 7.7 7.6867 20.0 3
Dual specificity tyrosine-phosphorylation-regulated kinase 1B
CHEMBL5543
 IC50 7.25 7.22 56.8 2
Dual specificity protein kinase CLK1
CHEMBL4224
 Kd 7.15 7.15 70.8 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 Kd 7.0 7.0 100.2 1
Dual specificity protein kinase CLK1
CHEMBL4224
 IC50 6.75 6.495 179.7 2
Dual specificity protein kinase CLK4
CHEMBL4203
 IC50 6.05 6.05 890.4 1
Dual specificity protein kinase CLK2
CHEMBL4225
 IC50 5.7 5.7 1993.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 2
CHEMBL4376
 IC50 5.47 5.47 3347.0 1
HT-22
CHEMBL614316
 IC50 5.05 5.05 9000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 9.4 nM 8.03 Inhibition of recombinant human DYRK1A expressed in Sf9 insect cells incubated f... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 20.0 nM 7.7 Inhibition of recombinant 6His-tagged rat DYRK1A (1 to 502 residues) expressed i... 38171148
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 20.7 nM 7.68 Inhibition of rat recombinant 6His-tagged DYRK1A (1 to 502 residues) catalytic d... 29985601
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 20.7 nM 7.68 Inhibition of 6xHis-tagged rat DYRK1A (1 to 502 residues) expressed in Escherich... 34954592
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 47.8 nM 7.32 Inhibition of recombinant human DYRK1A expressed in Escherichia coli using DYRKt... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B IC50 = 56.8 nM 7.25 Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells incubated f... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B IC50 = 64.4 nM 7.19 Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells using DYRKt... 36876904
Dual specificity protein kinase CLK1 Kd = 70.8 nM 7.15 Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A Kd = 100.21 nM 7.0 Binding affinity to human DYRK1A assessed as equilibrium dissociation constant m... 36876904
Dual specificity protein kinase CLK1 IC50 = 179.7 nM 6.75 Inhibition of recombinant human CLK1 expressed in Sf9 insect cells using myelin ... 36876904
Dual specificity protein kinase CLK1 IC50 = 570.3 nM 6.24 Inhibition of recombinant human CLK1 expressed in Sf9 insect cells incubated for... 36876904
Dual specificity protein kinase CLK4 IC50 = 890.4 nM 6.05 Inhibition of recombinant human CLK4 expressed in Sf9 insect cells incubated for... 36876904
Dual specificity protein kinase CLK2 IC50 = 1993.0 nM 5.7 Inhibition of recombinant human CLK2 expressed in Sf9 insect cells incubated for... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 2 IC50 = 3347.0 nM 5.47 Inhibition of recombinant human DYRK2 expressed in Sf9 insect cells incubated fo... 36876904
HT-22 IC50 = 9000.0 nM 5.05 Cytotoxicity against mouse HT-22 cells assessed as reduction in cell viability i... 36876904

Literature References

PubMed DOI Target Context # Activities
36876904 10.1021/acs.jmedchem.2c02068 Unchecked 5
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity protein kinase CLK1 4
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 4
36876904 10.1021/acs.jmedchem.2c02068 Glycogen synthase kinase-3 beta 3
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 1B 2
38171148 10.1016/j.ejmech.2023.116098 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 1
29985601 10.1021/acs.jmedchem.8b00185 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 1
36876904 10.1021/acs.jmedchem.2c02068 HT-22 1
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 4 1
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 3 1
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 2 1
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity protein kinase CLK4 1
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity protein kinase CLK3 1
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity protein kinase CLK2 1
36876904 10.1021/acs.jmedchem.2c02068 Casein kinase I isoform epsilon 1
36876904 10.1021/acs.jmedchem.2c02068 Cyclin-dependent kinase 5/CDK5 activator 1 1
34954592 10.1016/j.ejmech.2021.114062 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 1

Data from ChEMBL 36 via Core Engine