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Compound Detail

CHEMBL4128181

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CN(C)C(=O)C(C#N)=Cc1ccc(-c2nc3cnc4[nH]ccc4c3n2C2CCCCC2)o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4128181
Phase Preclinical
Structure Type MOL
InChI Key GJMZWYLOARVASY-UHFFFAOYSA-N
4
Targets
11
Activities
2
Assay Types
1
PK Parameters
12
Publications
0
Known Names

Molecular Properties

428.5
MW (Da)
4.67
ALogP
6
HBA
1
HBD
103.7
PSA (Ų)
0.38
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 C24H24N6O2
MW 428.50
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -1.04

Activity Summary

IC50 10 meas. best 9.89
EC50 1 meas. best 6.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 9.89 8.6725 0.1 4
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 7.28 6.725 52.0 2
Tyrosine-protein kinase JAK3
CHEMBL2148
 EC50 6.62 6.62 237.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 6.46 5.96 346.0 2
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 6.34 5.635 459.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 3.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase JAK3 IC50 = 0.13 nM 9.89 Inhibition of human JAK3 using GEEEEYFELVKKKK as substrate in presence of 10 uM ... 29852068
Tyrosine-protein kinase JAK3 IC50 = 2.0 nM 8.7 Inhibition of human JAK3 using GEEEEYFELVKKKK as substrate in presence of 200 uM... 29852068
Tyrosine-protein kinase JAK3 IC50 = 9.0 nM 8.05 Inhibition of recombinant human JAK3 (781 to 1124 residues) expressed in baculov... 29852068
Tyrosine-protein kinase JAK3 IC50 = 9.0 nM 8.05 Inhibition of JAK3 (unknown origin) incubated for 1 hr in presence of ATP and su... 34670167
Tyrosine-protein kinase JAK1 IC50 = 52.0 nM 7.28 Inhibition of human JAK1 using poly[Glu:Tyr] (4:1) as substrate in presence of 1... 29852068
Tyrosine-protein kinase JAK3 EC50 = 237.0 nM 6.62 Inhibition of kinase tracer-05 binding to C-terminal NanoLuc tagged full length ... 29852068
Tyrosine-protein kinase JAK2 IC50 = 346.0 nM 6.46 Inhibition of human JAK2 using poly[Glu:Tyr] (4:1) as substrate in presence of 1... 29852068
Non-receptor tyrosine-protein kinase TYK2 IC50 = 459.0 nM 6.34 Inhibition of human TYK2 using KKSRGDYMTMQIG as substrate in presence of 10 uM [... 29852068
Tyrosine-protein kinase JAK1 IC50 = 668.0 nM 6.17 Inhibition of human JAK1 using poly[Glu:Tyr] (4:1) as substrate in presence of 2... 29852068
Tyrosine-protein kinase JAK2 IC50 = 3460.0 nM 5.46 Inhibition of human JAK2 using poly[Glu:Tyr] (4:1) as substrate in presence of 2... 29852068
Non-receptor tyrosine-protein kinase TYK2 IC50 = 11800.0 nM 4.93 Inhibition of human TYK2 using KKSRGDYMTMQIG as substrate in presence of 200 uM ... 29852068

Literature References

PubMed DOI Target Context # Activities
29852068 10.1021/acs.jmedchem.8b00571 Tyrosine-protein kinase JAK3 4
29852068 10.1021/acs.jmedchem.8b00571 Unchecked 4
29852068 10.1021/acs.jmedchem.8b00571 Tyrosine-protein kinase JAK1 3
29852068 10.1021/acs.jmedchem.8b00571 Tyrosine-protein kinase JAK2 3
29852068 10.1021/acs.jmedchem.8b00571 ADMET 3
29852068 10.1021/acs.jmedchem.8b00571 Non-receptor tyrosine-protein kinase TYK2 2
29852068 10.1021/acs.jmedchem.8b00571 JAK3/JAK1 2
29852068 10.1021/acs.jmedchem.8b00571 Tyrosine-protein kinase BTK 1
29852068 10.1021/acs.jmedchem.8b00571 JAK1/JAK2/TYK2 1
29852068 10.1021/acs.jmedchem.8b00571 JAK1/TYK2 1
29852068 10.1021/acs.jmedchem.8b00571 No relevant target 1
34670167 10.1016/j.bmc.2021.116457 Tyrosine-protein kinase JAK3 1

Data from ChEMBL 36 via Core Engine