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Compound Detail

CHEMBL3216659

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Cl.Cl.O=C1Nc2cc(Br)ccc2/C1=C1/Nc2ccccc2/C1=N\OCCN1CCNCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3216659
Phase Preclinical
Structure Type MOL
InChI Key CVZJSHRSJMHZLV-BEDCTKBTSA-N
Parent Compound CHEMBL523714
Active Moiety CHEMBL523714
11
Targets
16
Activities
1
Assay Types
0
PK Parameters
16
Publications
0
Known Names

Molecular Properties

468.4
MW (Da)
2.86
ALogP
6
HBA
3
HBD
78.0
PSA (Ų)
0.37
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H24BrCl2N5O2
MW 541.28
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness -0.35

Activity Summary

IC50 16 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Proto-oncogene tyrosine-protein kinase Src
CHEMBL267
 IC50 9.7 9.7 0.2 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 9.06 8.545 0.9 2
Glycogen synthase kinase-3
CHEMBL2095188
 IC50 8.89 7.775 1.3 2
Unchecked
CHEMBL612545
 IC50 8.89 7.82 1.3 2
Aurora kinase A
CHEMBL4722
 IC50 8.15 8.15 7.1 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 7.55 7.1 28.0 2
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 7.3 7.3 50.0 1
Cyclin-dependent kinase 1/cyclin B1
CHEMBL1907602
 IC50 6.7 6.7 200.0 1
KCL-22
CHEMBL4296452
 IC50 6.48 6.425 330.0 2
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 6.22 6.22 600.0 1
SH-SY5Y
CHEMBL614910
 IC50 5.23 5.23 5900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Proto-oncogene tyrosine-protein kinase Src IC50 = 0.2 nM 9.7 Inhibition of recombinant GST-tagged c-Src catalytic domain (unknown origin) usi... 35749986
Tyrosine-protein kinase ABL1 IC50 = 0.87 nM 9.06 Inhibition of recombinant ABL1 (unknown origin) after 120 mins in presence of [3... 27726390
Unchecked IC50 = 1.3 nM 8.89 Inhibition of pig GSK3alpha/beta 18816110
Glycogen synthase kinase-3 IC50 = 1.3 nM 8.89 Inhibition of GSK3 (unknown origin) 34161865
Aurora kinase A IC50 = 7.1 nM 8.15 Inhibition of recombinant Aurora A (unknown origin) after 120 mins in presence o... 27726390
Tyrosine-protein kinase ABL1 IC50 = 9.4 nM 8.03 Inhibition of recombinant ABL1 T315I mutant (unknown origin) after 120 mins in p... 27726390
Tyrosine-protein kinase JAK2 IC50 = 28.0 nM 7.55 Inhibition of recombinant GST-tagged JAK2 catalytic domain (unknown origin) usin... 35749986
Non-receptor tyrosine-protein kinase TYK2 IC50 = 50.0 nM 7.3 Inhibition of recombinant GST-tagged TYK2 catalytic domain (unknown origin) usin... 35749986
Unchecked IC50 = 180.0 nM 6.75 Inhibition of human recombinant CDK5/p25 expressed in Escherichia coli 18816110
Cyclin-dependent kinase 1/cyclin B1 IC50 = 200.0 nM 6.7 Inhibition of CDK1/cyclin B 18816110
Glycogen synthase kinase-3 IC50 = 220.0 nM 6.66 Inhibition of GSK3-mediated beta-casein phosphorylation in human SH-SY5Y cells i... 18816110
Tyrosine-protein kinase JAK2 IC50 = 224.0 nM 6.65 Inhibition of recombinant JAK2 (unknown origin) after 120 mins in presence of [3... 27726390
KCL-22 IC50 = 330.0 nM 6.48 Cytotoxicity against human KCL22 cells assessed as reduction in cell viability a... 27726390
KCL-22 IC50 = 430.0 nM 6.37 Cytotoxicity against human KCL22 cells harboring ABL1 T315I mutant assessed as r... 27726390
Tyrosine-protein kinase JAK1 IC50 = 600.0 nM 6.22 Inhibition of recombinant GST-tagged JAK1 catalytic domain (unknown origin) usin... 35749986
SH-SY5Y IC50 = 5900.0 nM 5.23 Cytotoxicity against human SH-SY5Y cells after 48 hrs by MTS reduction assay 18816110

Literature References

PubMed DOI Target Context # Activities
27726390 10.1021/acs.jnatprod.6b00285 KCL-22 4
18816110 10.1021/jm800648y No relevant target 3
18816110 10.1021/jm800648y Unchecked 2
27726390 10.1021/acs.jnatprod.6b00285 Tyrosine-protein kinase ABL1 2
18816110 10.1021/jm800648y Cyclin-dependent kinase 1/cyclin B1 1
18816110 10.1021/jm800648y SH-SY5Y 1
18816110 10.1021/jm800648y Glycogen synthase kinase-3 1
27726390 10.1021/acs.jnatprod.6b00285 Aurora kinase A 1
27726390 10.1021/acs.jnatprod.6b00285 Proto-oncogene tyrosine-protein kinase Src 1
27726390 10.1021/acs.jnatprod.6b00285 Tyrosine-protein kinase JAK2 1
34161865 10.1016/j.ejmech.2021.113652 Glycogen synthase kinase-3 1
35749986 10.1016/j.ejmech.2022.114551 Tyrosine-protein kinase JAK1 1
35749986 10.1016/j.ejmech.2022.114551 Tyrosine-protein kinase JAK2 1
35749986 10.1016/j.ejmech.2022.114551 Non-receptor tyrosine-protein kinase TYK2 1
35749986 10.1016/j.ejmech.2022.114551 Proto-oncogene tyrosine-protein kinase Src 1
35749986 10.1016/j.ejmech.2022.114551 A2058 1

Data from ChEMBL 36 via Core Engine