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Compound Detail

CHEMBL4227082

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Cc1cn2c(-c3cn[nH]c3)cnc2c(Nc2cc(Cc3ccccn3)ns2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4227082
Phase Preclinical
Structure Type MOL
InChI Key NNQHKTWARZSGTQ-UHFFFAOYSA-N
7
Targets
8
Activities
3
Assay Types
25
PK Parameters
20
Publications
0
Known Names

Molecular Properties

388.5
MW (Da)
3.61
ALogP
8
HBA
2
HBD
96.7
PSA (Ų)
0.48
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H16N8S
MW 388.46
Aromatic Rings 5
Heavy Atoms 28
NP-Likeness -1.79

Activity Summary

IC50 5 meas. best 7.85
Kd 2 meas. best 11.0
EC50 1 meas. best 6.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aurora kinase A
CHEMBL4722
 Kd 11.0 11.0 0.0 1
Aurora kinase B
CHEMBL2185
 Kd 10.0 10.0 0.1 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 7.85 7.85 14.0 1
Aurora kinase B
CHEMBL2185
 EC50 6.93 6.93 117.0 1
Ribosomal protein S6 kinase alpha-3
CHEMBL2345
 IC50 6.58 6.58 260.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 6.57 6.57 271.0 1
Serine/threonine-protein kinase Chk1
CHEMBL4630
 IC50 6.44 6.44 360.0 1
Ephrin type-B receptor 4
CHEMBL5147
 IC50 6.41 6.41 390.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6875.74 ng.hr.mL-1 Rattus norvegicus
AUC 427.31 ng.hr.mL-1 Mus musculus
AUC 5477.29 ng.hr.mL-1 Mus musculus
AUC 1087.69 ng.hr.mL-1 Rattus norvegicus
AUC 310.77 ng.hr.mL-1 Rattus norvegicus
AUC 3573.83 ng.hr.mL-1 Canis lupus familiaris
AUC 1592.69 ng.hr.mL-1 Canis lupus familiaris
AUC 660.38 ng.hr.mL-1 Macaca mulatta
AUC - ng.hr.mL-1 Macaca mulatta
CL 118.0 mL.min-1.kg-1 Mus musculus
CL 15.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.0 mL.min-1.kg-1 Canis lupus familiaris
CL 28.0 mL.min-1.kg-1 Macaca mulatta
F 77.0 % Mus musculus
F 10.0 % Rattus norvegicus
F 15.0 % Canis lupus familiaris
F - % Macaca mulatta
T1/2 0.2 hr Mus musculus
T1/2 0.7 hr Rattus norvegicus
T1/2 0.8 hr Canis lupus familiaris
T1/2 0.5 hr Macaca mulatta
Vd 1.6 L.kg-1 Mus musculus
Vd 0.7 L.kg-1 Rattus norvegicus
Vd 0.2 L.kg-1 Canis lupus familiaris
Vd 1.0 L.kg-1 Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aurora kinase A Kd = 0.01 nM 11.0 Binding affinity to Aurora A (unknown origin) after 45 mins by fluorescence-base... 29545102
Aurora kinase B Kd = 0.1 nM 10.0 Binding affinity to Aurora B (unknown origin) after 45 mins by fluorescence-base... 29545102
Receptor-type tyrosine-protein kinase FLT3 IC50 = 14.0 nM 7.85 Inhibition of FLT3 (unknown origin) 29545102
Aurora kinase B EC50 = 117.0 nM 6.93 Inhibition of Aurora B in human HCT116 cells assessed as reduction in phosphoryl... 29545102
Ribosomal protein S6 kinase alpha-3 IC50 = 260.0 nM 6.58 Inhibition of RSK2 (unknown origin) 29545102
Tyrosine-protein kinase Lck IC50 = 271.0 nM 6.57 Inhibition of LCK (unknown origin) 29545102
Serine/threonine-protein kinase Chk1 IC50 = 360.0 nM 6.44 Inhibition of CHK1 (unknown origin) 29545102
Ephrin type-B receptor 4 IC50 = 390.0 nM 6.41 Inhibition of EPHB4 (unknown origin) 29545102

Literature References

PubMed DOI Target Context # Activities
29545102 10.1016/j.bmcl.2018.02.037 Rattus norvegicus 7
29545102 10.1016/j.bmcl.2018.02.037 Mus musculus 6
29545102 10.1016/j.bmcl.2018.02.037 Canis familiaris 6
29545102 10.1016/j.bmcl.2018.02.037 Rhesus monkey 6
29545102 10.1016/j.bmcl.2018.02.037 ADMET 4
29545102 10.1016/j.bmcl.2018.02.037 Aurora kinase B 3
29545102 10.1016/j.bmcl.2018.02.037 Aurora kinase A 2
29545102 10.1016/j.bmcl.2018.02.037 Receptor-type tyrosine-protein kinase FLT3 1
29545102 10.1016/j.bmcl.2018.02.037 Tyrosine-protein kinase Lck 1
29545102 10.1016/j.bmcl.2018.02.037 Ribosomal protein S6 kinase alpha-3 1
29545102 10.1016/j.bmcl.2018.02.037 No relevant target 1
29545102 10.1016/j.bmcl.2018.02.037 Calcium/calmodulin-dependent protein kinase type IV 1
29545102 10.1016/j.bmcl.2018.02.037 Cyclin-dependent kinase 2 1
29545102 10.1016/j.bmcl.2018.02.037 Casein kinase I isoform delta 1
29545102 10.1016/j.bmcl.2018.02.037 Epidermal growth factor receptor 1
29545102 10.1016/j.bmcl.2018.02.037 Mitogen-activated protein kinase 1 1
29545102 10.1016/j.bmcl.2018.02.037 Glycogen synthase kinase-3 beta 1
29545102 10.1016/j.bmcl.2018.02.037 Ephrin type-B receptor 4 1
29545102 10.1016/j.bmcl.2018.02.037 Inhibitor of nuclear factor kappa-B kinase subunit beta 1
29545102 10.1016/j.bmcl.2018.02.037 Tyrosine-protein kinase JAK2 1

Data from ChEMBL 36 via Core Engine