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Compound Detail

CHEMBL4062453

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CN(C)CCn1cc(-c2ccn3c(-c4ccc(C(N)=O)c(OCc5cccc(F)c5)c4)cnc3c2)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4062453
Phase Preclinical
Structure Type MOL
InChI Key CGECJCJUHCZZGO-UHFFFAOYSA-N
15
Targets
18
Activities
1
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

498.6
MW (Da)
4.24
ALogP
7
HBA
1
HBD
90.7
PSA (Ų)
0.33
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C28H27FN6O2
MW 498.56
Aromatic Rings 5
Heavy Atoms 37
NP-Likeness -1.70

Activity Summary

IC50 18 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase Nek2
CHEMBL3835
 IC50 9.0 9.0 1.0 1
Ribosomal protein S6 kinase alpha-1
CHEMBL2553
 IC50 8.27 8.27 5.4 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 IC50 8.19 8.19 6.5 1
Tyrosine-protein kinase ABL1
CHEMBL1862
 IC50 7.7 7.7 20.0 1
Serine/threonine-protein kinase Chk1
CHEMBL4630
 IC50 7.24 7.24 57.0 1
Glycogen synthase kinase-3 beta
CHEMBL262
 IC50 7.04 7.04 91.0 1
Cyclin-dependent kinase 2
CHEMBL301
 IC50 6.43 6.43 370.0 1
Cyclin-dependent kinase 4
CHEMBL331
 IC50 6.36 6.36 441.0 1
MGC-803
CHEMBL3706566
 IC50 6.28 6.235 530.0 2
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 IC50 6.22 6.22 608.0 1
HCT-116
CHEMBL394
 IC50 6.16 6.12 700.0 2
Hep 3B2
CHEMBL4296437
 IC50 5.97 5.97 1070.0 1
Aurora kinase A
CHEMBL4722
 IC50 5.28 5.28 5300.0 1
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
CHEMBL4005
 IC50 5.21 5.21 6226.0 1
Bel-7402
CHEMBL614279
 IC50 5.2 5.175 6370.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 495.0 ng.hr.mL-1 Rattus norvegicus
AUC 507.0 ng.hr.mL-1 Rattus norvegicus
CL 33.3 mL.min-1.kg-1 Rattus norvegicus
T1/2 1.72 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase Nek2 IC50 = 1.0 nM 9.0 Inhibition of N-terminal His6-tagged full-length recombinant human NEK2 expresse... 28039836
Ribosomal protein S6 kinase alpha-1 IC50 = 5.4 nM 8.27 Inhibition of RSK1 (unknown origin) 28039836
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 6.5 nM 8.19 Inhibition of DYRK1A (unknown origin) 28039836
Tyrosine-protein kinase ABL1 IC50 = 20.0 nM 7.7 Inhibition of ABL (unknown origin) 28039836
Serine/threonine-protein kinase Chk1 IC50 = 57.0 nM 7.24 Inhibition of CHK1 (unknown origin) 28039836
Glycogen synthase kinase-3 beta IC50 = 91.0 nM 7.04 Inhibition of GSK3beta (unknown origin) 28039836
Cyclin-dependent kinase 2 IC50 = 370.0 nM 6.43 Inhibition of CDK2 (unknown origin) 28039836
Cyclin-dependent kinase 4 IC50 = 441.0 nM 6.36 Inhibition of CDK4 (unknown origin) 28039836
MGC-803 IC50 = 530.0 nM 6.28 Cytotoxicity against human MGC803 cells measured after 72 hrs by MTT assay 28039836
RAC-alpha serine/threonine-protein kinase IC50 = 608.0 nM 6.22 Inhibition of AKT1 (unknown origin) 28039836
MGC-803 IC50 = 650.0 nM 6.19 Antitumor activity against human MGC-803 cells assessed as inhibition of cell pr... 32992252
HCT-116 IC50 = 700.0 nM 6.16 Antitumor activity against human HCT-116 cells assessed as inhibition of cell pr... 32992252
HCT-116 IC50 = 840.0 nM 6.08 Cytotoxicity against human HCT116 cells measured after 72 hrs by MTT assay 28039836
Hep 3B2 IC50 = 1070.0 nM 5.97 Antitumor activity against human Hep3B cells assessed as inhibition of cell prol... 32992252
Aurora kinase A IC50 = 5300.0 nM 5.28 Inhibition of Aurora A (unknown origin) 28039836
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform IC50 = 6226.0 nM 5.21 Inhibition of PI3Kalpha (unknown origin) 28039836
Bel-7402 IC50 = 6370.0 nM 5.2 Antitumor activity against human Bel-7402 cells assessed as inhibition of cell p... 32992252
Bel-7402 IC50 = 7130.0 nM 5.15 Cytotoxicity against human Bel7402 cells measured after 72 hrs by MTT assay 28039836

Literature References

PubMed DOI Target Context # Activities
28039836 10.1016/j.ejmech.2016.12.026 HCT-116 10
28039836 10.1016/j.ejmech.2016.12.026 Rattus norvegicus 6
28039836 10.1016/j.ejmech.2016.12.026 Unchecked 3
28039836 10.1016/j.ejmech.2016.12.026 MAP kinase-activated protein kinase 2 1
32992252 10.1016/j.bmc.2020.115775 HCT-116 1
32992252 10.1016/j.bmc.2020.115775 Hep 3B2 1
32992252 10.1016/j.bmc.2020.115775 MGC-803 1
28039836 10.1016/j.ejmech.2016.12.026 Cyclin-dependent kinase 4 1
28039836 10.1016/j.ejmech.2016.12.026 Cyclin-dependent kinase 2 1
28039836 10.1016/j.ejmech.2016.12.026 Mitogen-activated protein kinase 14 1
28039836 10.1016/j.ejmech.2016.12.026 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 1
28039836 10.1016/j.ejmech.2016.12.026 Glycogen synthase kinase-3 beta 1
28039836 10.1016/j.ejmech.2016.12.026 Serine/threonine-protein kinase Nek2 1
28039836 10.1016/j.ejmech.2016.12.026 Serine/threonine-protein kinase Chk1 1
28039836 10.1016/j.ejmech.2016.12.026 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 1
28039836 10.1016/j.ejmech.2016.12.026 Ribosomal protein S6 kinase alpha-1 1
28039836 10.1016/j.ejmech.2016.12.026 Tyrosine-protein kinase ABL1 1
28039836 10.1016/j.ejmech.2016.12.026 RAC-alpha serine/threonine-protein kinase 1
28039836 10.1016/j.ejmech.2016.12.026 Aurora kinase A 1
28039836 10.1016/j.ejmech.2016.12.026 Bel-7402 1

Data from ChEMBL 36 via Core Engine