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Compound Detail

CHEMBL4290597

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COc1cc2c(=O)n([C@@H]3CCCN(C(=O)CC#N)C3)c3c4cc[nH]c4ncc3c2cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4290597
Phase Preclinical
Structure Type MOL
InChI Key NLGZSRKKPYFWHZ-CQSZACIVSA-N
7
Targets
13
Activities
2
Assay Types
1
PK Parameters
14
Publications
0
Known Names

Molecular Properties

445.5
MW (Da)
3.13
ALogP
7
HBA
1
HBD
113.2
PSA (Ų)
0.48
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 C24H23N5O4
MW 445.48
Aromatic Rings 4
Heavy Atoms 33
NP-Likeness -0.72

Activity Summary

IC50 11 meas. best 8.99
Kd 2 meas. best 9.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
BMP-2-inducible protein kinase
CHEMBL4522
 Kd 9.66 9.66 0.2 1
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 8.99 8.955 1.0 2
Mitogen-activated protein kinase kinase kinase 19
CHEMBL6191
 Kd 8.92 8.92 1.2 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 8.59 7.7025 2.5 4
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 8.51 8.51 3.1 2
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 8.36 8.36 4.3 2
Unchecked
CHEMBL612545
 IC50 6.17 6.17 680.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
BMP-2-inducible protein kinase Kd = 0.22 nM 9.66 Binding affinity to DNA-tagged recombinant human BIKE (34 to 329 residues) expre... 30460842
Tyrosine-protein kinase JAK1 IC50 = 1.02 nM 8.99 JAK Inhibition Activity Assays: Reagents used in JAK inhibition assay: Base Reac... -
Tyrosine-protein kinase JAK1 IC50 = 1.2 nM 8.92 Inhibition of JAK1 (unknown origin) preincubated for 20 mins followed by [33P]-A... 30460842
Mitogen-activated protein kinase kinase kinase 19 Kd = 1.2 nM 8.92 Binding affinity to DNA-tagged recombinant human YSK4 (1019 to 1328 residues) ex... 30460842
Tyrosine-protein kinase JAK3 IC50 = 2.55 nM 8.59 Inhibition of JAK3 (unknown origin) preincubated for 20 mins followed by [33P]-A... 30460842
Tyrosine-protein kinase JAK3 IC50 = 2.55 nM 8.59 JAK Inhibition Activity Assays: Reagents used in JAK inhibition assay: Base Reac... -
Tyrosine-protein kinase JAK2 IC50 = 3.12 nM 8.51 Inhibition of JAK2 (unknown origin) preincubated for 20 mins followed by [33P]-A... 30460842
Tyrosine-protein kinase JAK2 IC50 = 3.12 nM 8.51 JAK Inhibition Activity Assays: Reagents used in JAK inhibition assay: Base Reac... -
Non-receptor tyrosine-protein kinase TYK2 IC50 = 4.35 nM 8.36 Inhibition of TYK2 (unknown origin) preincubated for 20 mins followed by [33P]-A... 30460842
Non-receptor tyrosine-protein kinase TYK2 IC50 = 4.35 nM 8.36 JAK Inhibition Activity Assays: Reagents used in JAK inhibition assay: Base Reac... -
Tyrosine-protein kinase JAK3 IC50 = 15.3 nM 7.82 Inhibition of JAK3 in human SZ4 cells assessed as reduction in IL2-stimulated ST... 30460842
Unchecked IC50 = 680.0 nM 6.17 Inhibition of cell proliferation of IL2-activated and CD3 and CD28 antibody-stim... 30460842
Tyrosine-protein kinase JAK3 IC50 = 1550.0 nM 5.81 Inhibition of JAK3 in human SZ4 cells assessed as reduction in IL2-stimulated ST... 30460842

Literature References

PubMed DOI Target Context # Activities
30460842 10.1021/acs.jmedchem.8b00510 Unchecked 6
30460842 10.1021/acs.jmedchem.8b00510 Tyrosine-protein kinase JAK3 3
30460842 10.1021/acs.jmedchem.8b00510 No relevant target 3
30460842 10.1021/acs.jmedchem.8b00510 ADMET 3
30460842 10.1021/acs.jmedchem.8b00510 Receptor-type tyrosine-protein kinase FLT3 2
30460842 10.1021/acs.jmedchem.8b00510 Non-receptor tyrosine-protein kinase TYK2 1
30460842 10.1021/acs.jmedchem.8b00510 Tyrosine-protein kinase JAK2 1
30460842 10.1021/acs.jmedchem.8b00510 Tyrosine-protein kinase JAK1 1
30460842 10.1021/acs.jmedchem.8b00510 DNA topoisomerase 1 1
30460842 10.1021/acs.jmedchem.8b00510 NUAK family SNF1-like kinase 1 1
30460842 10.1021/acs.jmedchem.8b00510 BMP-2-inducible protein kinase 1
30460842 10.1021/acs.jmedchem.8b00510 NUAK family SNF1-like kinase 2 1
30460842 10.1021/acs.jmedchem.8b00510 High affinity nerve growth factor receptor 1
30460842 10.1021/acs.jmedchem.8b00510 Mitogen-activated protein kinase kinase kinase 19 1

Data from ChEMBL 36 via Core Engine