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Compound Detail

CHEMBL5422616

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CNc1cc(Nc2cccn(-c3ccccn3)c2=O)nc2c(C(=O)N[C@H]3CC[C@@H]3OC)cnn12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5422616
Phase Preclinical
Structure Type MOL
InChI Key BWINBHTTZLVXGT-RDJZCZTQSA-N
9
Targets
18
Activities
2
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

460.5
MW (Da)
1.97
ALogP
10
HBA
3
HBD
127.5
PSA (Ų)
0.38
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H24N8O3
MW 460.50
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -1.28

Activity Summary

IC50 10 meas. best 8.77
Kd 8 meas. best 10.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Non-receptor tyrosine-protein kinase TYK2
CHEMBL2321619
 Kd 10.17 10.17 0.1 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 Kd 9.22 9.22 0.6 4
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 8.77 8.47 1.7 2
Unchecked
CHEMBL612545
 IC50 8.43 7.5967 3.7 3
Blood
CHEMBL613416
 IC50 7.66 7.66 22.0 1
Blood
CHEMBL613561
 IC50 6.46 6.46 347.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.7 5.39 2000.0 2
Tyrosine-protein kinase JAK1
CHEMBL2835
 Kd 5.3 5.3 4975.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.72 4.72 19000.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 Kd 4.64 4.64 23000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 16.0 mL.min-1.kg-1 Mus musculus
CL 26.0 mL.min-1.kg-1 Rattus norvegicus
CL 7.0 mL.min-1.kg-1 Canis lupus familiaris
CL 7.0 mL.min-1.kg-1 Macaca fascicularis
F 70.0 % Mus musculus
F 37.0 % Rattus norvegicus
F 47.0 % Canis lupus familiaris
F 47.0 % Macaca fascicularis
Fu 0.23 - Homo sapiens
Fu 0.08 - Mus musculus
Fu 0.15 - Rattus norvegicus
Fu 0.23 - Canis lupus familiaris
Fu 0.23 - Macaca fascicularis
T1/2 2.0 hr Mus musculus
T1/2 1.2 hr Rattus norvegicus
T1/2 5.3 hr Canis lupus familiaris
T1/2 3.8 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Non-receptor tyrosine-protein kinase TYK2 Kd = 0.067 nM 10.17 Binding affinity to mouse TYK2 JH2 domain assessed as dissociation constant 37427891
Non-receptor tyrosine-protein kinase TYK2 Kd = 0.6 nM 9.22 TYK2 JH2 Domain Binding Assay: Binding constants for compounds of the present in... -
Non-receptor tyrosine-protein kinase TYK2 Kd = 0.6 nM 9.22 TYK2 JH2 Domain Binding Assay: Binding constants for compounds against the JH2 d... -
Non-receptor tyrosine-protein kinase TYK2 Kd = 0.6 nM 9.22 TYK2 JH2 Domain Binding Assay: Binding constants for compounds of the present in... -
Non-receptor tyrosine-protein kinase TYK2 Kd = 0.6 nM 9.22 TYK2 JH2 Domain Binding Assay: The binding reaction was assembled by combining 1... -
Non-receptor tyrosine-protein kinase TYK2 IC50 = 1.7 nM 8.77 Inhibition of TYK2 dependent IFNalpha-stimulated STAT3 phosphorylation in human ... 37427891
Unchecked IC50 = 3.7 nM 8.43 Inhibition of IL23-induced STAT3 phosphorylation in human CD161+CD3+Th17 cells 37427891
Non-receptor tyrosine-protein kinase TYK2 IC50 = 6.7 nM 8.17 Inhibition of TYK2 in human PBMC cells assessed as IL-12 induced phosphorylation... 37427891
Blood IC50 = 22.0 nM 7.66 In vivo inhibition of JAK/STAT signaling pathway in human assessed as downregula... 37427891
Unchecked IC50 = 48.0 nM 7.32 Inhibition of IL12-IL18-induced IFNgamma production in human whole blood cells 37427891
Unchecked IC50 = 91.0 nM 7.04 Inhibition of TYK2 signaling pathway in rat whole blood assessed as downregulati... 37427891
Blood IC50 = 347.0 nM 6.46 In vivo inhibition of JAK/STAT signaling pathway in mouse assessed as downregula... 37427891
Cytochrome P450 3A4 IC50 = 2000.0 nM 5.7 Inhibition of human CYP3A4 using testosterone as substrate 37427891
Tyrosine-protein kinase JAK1 Kd = 4975.0 nM 5.3 Binding affinity to human JAK1 JH2 domain assessed as dissociation constant 37427891
Cytochrome P450 3A4 IC50 = 8300.0 nM 5.08 Inhibition of human CYP3A4 using midazolam as substrate 37427891
Cytochrome P450 2C19 IC50 = 19000.0 nM 4.72 Inhibition of human CYP2C19 37427891
Tyrosine-protein kinase JAK2 Kd = 23000.0 nM 4.64 Binding affinity to human JAK2 JH2 domain assessed as dissociation constant 37427891

Literature References

PubMed DOI Target Context # Activities
37427891 10.1021/acs.jmedchem.3c00600 ADMET 22
37427891 10.1021/acs.jmedchem.3c00600 Unchecked 7
37427891 10.1021/acs.jmedchem.3c00600 Non-receptor tyrosine-protein kinase TYK2 4
37427891 10.1021/acs.jmedchem.3c00600 JAK2/JAK1 3
37427891 10.1021/acs.jmedchem.3c00600 Janus Kinase (JAK) 2
37427891 10.1021/acs.jmedchem.3c00600 Blood 2
37427891 10.1021/acs.jmedchem.3c00600 Cytochrome P450 3A4 2
37427891 10.1021/acs.jmedchem.3c00600 JAK3/JAK1 2
37427891 10.1021/acs.jmedchem.3c00600 Tyrosine-protein kinase JAK2 2
37427891 10.1021/acs.jmedchem.3c00600 Cytochrome P450 1A2 1
37427891 10.1021/acs.jmedchem.3c00600 Rattus norvegicus 1
37427891 10.1021/acs.jmedchem.3c00600 Tyrosine-protein kinase JAK1 1
37427891 10.1021/acs.jmedchem.3c00600 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37427891 10.1021/acs.jmedchem.3c00600 Phosphatidylinositol 4-phosphate 5-kinase type-1 gamma 1
37427891 10.1021/acs.jmedchem.3c00600 Tyrosine-protein kinase Lck 1
37427891 10.1021/acs.jmedchem.3c00600 Nuclear receptor subfamily 1 group I member 2 1
37427891 10.1021/acs.jmedchem.3c00600 Cytochrome P450 2C19 1
37427891 10.1021/acs.jmedchem.3c00600 Cytochrome P450 2C9 1
37427891 10.1021/acs.jmedchem.3c00600 Cytochrome P450 2D6 1
37427891 10.1021/acs.jmedchem.3c00600 3',5'-cyclic-AMP phosphodiesterase 4D 1

Data from ChEMBL 36 via Core Engine