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Compound Detail

CHEMBL494867

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CN(CCO/N=C1C(=C2/C(=O)Nc3cc(Br)ccc32)/Nc2ccccc2/1)CC(O)CO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL494867
Phase Preclinical
Structure Type MOL
InChI Key RWKFWKPIQLFUQP-OQBIKMBDSA-N
7
Targets
10
Activities
1
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

487.4
MW (Da)
2.24
ALogP
7
HBA
4
HBD
106.4
PSA (Ų)
0.27
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H23BrN4O4
MW 487.35
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness -0.22

Activity Summary

IC50 10 meas. best 8.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 8.14 7.445 7.2 2
Aurora kinase A
CHEMBL4722
 IC50 8.01 8.01 9.7 1
Unchecked
CHEMBL612545
 IC50 7.17 6.895 67.0 2
Cyclin-dependent kinase 1/cyclin B1
CHEMBL1907602
 IC50 6.62 6.62 240.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 6.26 6.26 551.0 1
KCL-22
CHEMBL4296452
 IC50 6.18 6.175 660.0 2
SH-SY5Y
CHEMBL614910
 IC50 5.24 5.24 5800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase ABL1 IC50 = 7.2 nM 8.14 Inhibition of recombinant ABL1 (unknown origin) after 120 mins in presence of [3... 27726390
Aurora kinase A IC50 = 9.7 nM 8.01 Inhibition of recombinant Aurora A (unknown origin) after 120 mins in presence o... 27726390
Unchecked IC50 = 67.0 nM 7.17 Inhibition of pig GSK3alpha/beta 18816110
Tyrosine-protein kinase ABL1 IC50 = 178.0 nM 6.75 Inhibition of recombinant ABL1 T315I mutant (unknown origin) after 120 mins in p... 27726390
Cyclin-dependent kinase 1/cyclin B1 IC50 = 240.0 nM 6.62 Inhibition of CDK1/cyclin B 18816110
Unchecked IC50 = 240.0 nM 6.62 Inhibition of human recombinant CDK5/p25 expressed in Escherichia coli 18816110
Tyrosine-protein kinase JAK2 IC50 = 551.0 nM 6.26 Inhibition of recombinant JAK2 (unknown origin) after 120 mins in presence of [3... 27726390
KCL-22 IC50 = 660.0 nM 6.18 Cytotoxicity against human KCL22 cells harboring ABL1 T315I mutant assessed as r... 27726390
KCL-22 IC50 = 680.0 nM 6.17 Cytotoxicity against human KCL22 cells assessed as reduction in cell viability a... 27726390
SH-SY5Y IC50 = 5800.0 nM 5.24 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 Unchecked 2
24697244 10.1021/jm401740w Polyunsaturated fatty acid 5-lipoxygenase 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
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

Data from ChEMBL 36 via Core Engine