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Compound Detail

CHEMBL3589662

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O=C(O)c1nc2ccccc2c2[nH]c3c(I)cccc3c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3589662
Phase Preclinical
Structure Type MOL
InChI Key SDRAETFVRBBLOB-UHFFFAOYSA-N
9
Targets
19
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

388.2
MW (Da)
4.17
ALogP
2
HBA
2
HBD
66.0
PSA (Ų)
0.48
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H9IN2O2
MW 388.16
Aromatic Rings 4
Heavy Atoms 21
NP-Likeness -0.26

Activity Summary

IC50 16 meas. best 8.64
Kd 3 meas. best 8.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 IC50 8.64 7.5167 2.3 6
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 Kd 8.62 8.62 2.4 1
Dual specificity protein kinase CLK1
CHEMBL4224
 Kd 8.21 8.21 6.2 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1B
CHEMBL5543
 IC50 8.11 6.5633 7.7 3
Dual specificity protein kinase CLK1
CHEMBL4224
 IC50 7.84 6.64 14.6 2
Dual specificity protein kinase CLK4
CHEMBL1075283
 IC50 6.68 6.68 210.0 1
Dual specificity protein kinase CLK4
CHEMBL4203
 IC50 6.5 6.5 316.0 1
Glycogen synthase kinase-3 beta
CHEMBL262
 Kd 6.32 6.32 474.6 1
Dual specificity protein kinase CLK1
CHEMBL1075280
 IC50 6.3 6.3 500.0 1
Dual specificity protein kinase CLK2
CHEMBL4225
 IC50 5.29 5.29 5140.0 1
Dual specificity protein kinase CLK2
CHEMBL1075281
 IC50 5.26 5.26 5500.0 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 = 2.3 nM 8.64 Inhibition of recombinant human DYRK1A expressed in Escherichia coli using DYRKt... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A Kd = 2.385 nM 8.62 Binding affinity to human DYRK1A assessed as equilibrium dissociation constant m... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 6.0 nM 8.22 Inhibition of human recombinant DYRK1A expressed in Escherichia coli using RS pe... 25730262
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 6.0 nM 8.22 Inhibition of DYRK1A (unknown origin) using KKISGRLSPIMTEQ as substrate incubate... 34954592
Dual specificity protein kinase CLK1 Kd = 6.22 nM 8.21 Binding affinity to human CLK1 assessed as equilibrium dissociation constant mea... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B IC50 = 7.7 nM 8.11 Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells using DYRKt... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 9.2 nM 8.04 Inhibition of recombinant human DYRK1A expressed in Sf9 insect cells incubated f... 36876904
Dual specificity protein kinase CLK1 IC50 = 14.6 nM 7.84 Inhibition of recombinant human CLK1 expressed in Sf9 insect cells using myelin ... 36876904
Dual specificity protein kinase CLK4 IC50 = 210.0 nM 6.68 Inhibition of mouse recombinant CLK4 expressed in Escherichia coli using RS pept... 25730262
Dual specificity protein kinase CLK4 IC50 = 316.0 nM 6.5 Inhibition of recombinant human CLK4 expressed in Sf9 insect cells incubated for... 36876904
Glycogen synthase kinase-3 beta Kd = 474.59 nM 6.32 Binding affinity to human GSK-3beta assessed as equilibrium dissociation constan... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 500.0 nM 6.3 Inhibition of DYRK1A in HEK293 cells assessed as inhibition of tau phosphorylati... 25730262
Dual specificity protein kinase CLK1 IC50 = 500.0 nM 6.3 Inhibition of mouse recombinant CLK1 expressed in Escherichia coli using RS pept... 25730262
Dual specificity tyrosine-phosphorylation-regulated kinase 1B IC50 = 600.0 nM 6.22 Inhibition of human recombinant DYRK1B expressed in Escherichia coli using RS pe... 25730262
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 2100.0 nM 5.68 Inhibition of DYRK1A in human HeLa cells assessed as reduction of SF3B1 phosphor... 25730262
Dual specificity protein kinase CLK1 IC50 = 3610.0 nM 5.44 Inhibition of recombinant human CLK1 expressed in Sf9 insect cells incubated for... 36876904
Dual specificity tyrosine-phosphorylation-regulated kinase 1B IC50 = 4406.0 nM 5.36 Inhibition of recombinant human DYRK1B expressed in Sf9 insect cells incubated f... 36876904
Dual specificity protein kinase CLK2 IC50 = 5140.0 nM 5.29 Inhibition of recombinant human CLK2 expressed in Sf9 insect cells incubated for... 36876904
Dual specificity protein kinase CLK2 IC50 = 5500.0 nM 5.26 Inhibition of mouse recombinant CLK2 expressed in Escherichia coli using RS pept... 25730262

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058564 U2OS 6
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 5
36876904 10.1021/acs.jmedchem.2c02068 Unchecked 5
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity protein kinase CLK1 4
25730262 10.1021/jm501994d Dual specificity tyrosine-phosphorylation-regulated kinase 1A 4
- 10.6019/CHEMBL5058564 HEK-293T 4
36876904 10.1021/acs.jmedchem.2c02068 Glycogen synthase kinase-3 beta 3
25730262 10.1021/jm501994d Unchecked 3
36876904 10.1021/acs.jmedchem.2c02068 Dual specificity tyrosine-phosphorylation-regulated kinase 1B 2
- 10.6019/CHEMBL5058564 Fibroblast 2
25730262 10.1021/jm501994d Dual specificity tyrosine-phosphorylation-regulated kinase 2 1
- 10.6019/CHEMBL5060014 Peregrin 1
- 10.6019/CHEMBL5060014 Bromodomain-containing protein 4 1
36876904 10.1021/acs.jmedchem.2c02068 HT-22 1
25730262 10.1021/jm501994d Dual specificity tyrosine-phosphorylation-regulated kinase 3 1
25730262 10.1021/jm501994d Dual specificity protein kinase CLK4 1
25730262 10.1021/jm501994d Dual specificity protein kinase CLK3 1
25730262 10.1021/jm501994d Dual specificity protein kinase CLK1 1
25730262 10.1021/jm501994d Cyclin-dependent kinase 9 1
25730262 10.1021/jm501994d Cyclin-dependent kinase 5 1

Data from ChEMBL 36 via Core Engine