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CHEMBL2057918

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CN1CCN(c2ccc(Nc3cc(-c4cccc(-n5ccc6cc(C7CC7)cc(F)c6c5=O)c4CO)cn(C)c3=O)nc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2057918
Phase Preclinical
Structure Type MOL
InChI Key ZTUJNJAKTLHBEX-UHFFFAOYSA-N
10
Targets
23
Activities
1
Assay Types
18
PK Parameters
20
Publications
0
Known Names

Molecular Properties

606.7
MW (Da)
4.76
ALogP
9
HBA
2
HBD
95.6
PSA (Ų)
0.28
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C35H35FN6O3
MW 606.70
Aromatic Rings 5
Heavy Atoms 45
NP-Likeness -0.90

Activity Summary

IC50 23 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 9.52 8.0846 0.3 13
Macrophage
CHEMBL612578
 IC50 8.4 8.4 4.0 1
Tyrosine-protein kinase Tec
CHEMBL4246
 IC50 8.24 7.715 5.7 2
Blood
CHEMBL613416
 IC50 7.77 7.77 17.0 1
Mast cell
CHEMBL613709
 IC50 7.54 7.54 29.2 1
STE20-like serine/threonine-protein kinase
CHEMBL4202
 IC50 7.37 7.37 43.0 1
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 IC50 7.21 7.21 62.0 1
Tyrosine-protein kinase Fgr
CHEMBL4454
 IC50 6.75 6.75 180.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.85 5.85 1400.0 1
Tyrosine-protein kinase Yes
CHEMBL2073
 IC50 5.8 5.8 1592.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 403.9 ng.hr.mL-1 Rattus norvegicus
AUC 402.7 ng.hr.mL-1 Rattus norvegicus
AUC 1053.5 ng.hr.mL-1 Rattus norvegicus
CL 41.17 mL.min-1.kg-1 Rattus norvegicus
CL 84.5 mL.min-1.kg-1 Rattus norvegicus
CL 53.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 363.11 nM Rattus norvegicus
Cmax 57.36 nM Rattus norvegicus
Cmax 221.03 nM Rattus norvegicus
F 49.9 % Rattus norvegicus
MRT 6.56 hr Rattus norvegicus
MRT 9.31 hr Rattus norvegicus
T1/2 14.1 hr Rattus norvegicus
T1/2 11.5 hr Rattus norvegicus
T1/2 4.4 hr Rattus norvegicus
Tmax 4.0 hr Rattus norvegicus
Vd 50.51 L.kg-1 Rattus norvegicus
Vd 86.69 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase BTK IC50 = 0.3 nM 9.52 Competitive inhibition of BTK by TR-FRET based competitive assay 22394077
Tyrosine-protein kinase BTK IC50 = 0.9 nM 9.05 Inhibition of BTK (unknown origin) 33932711
Tyrosine-protein kinase BTK IC50 = 2.25 nM 8.65 Inhibition of human BTK 33932711
Macrophage IC50 = 4.0 nM 8.4 Inhibition of immobilized immune complex-stimulated TNFalpha production in macro... 22394077
Tyrosine-protein kinase BTK IC50 = 4.0 nM 8.4 Inhibition of BTK (unknown origin) 29631132
Tyrosine-protein kinase Tec IC50 = 5.69 nM 8.24 Inhibition of human TEC 33932711
Tyrosine-protein kinase BTK IC50 = 7.0 nM 8.15 Inhibition of BTK (unknown origin) assessed as reduction in TNF production 29631132
Tyrosine-protein kinase BTK IC50 = 13.0 nM 7.89 Inhibition of BTK (unknown origin) using biotin-labeled peptide substrate incuba... 25515957
Tyrosine-protein kinase BTK IC50 = 13.2 nM 7.88 Inhibition of BTK (unknown origin) after 1 hr by TR-FRET analysis 25596757
Tyrosine-protein kinase BTK IC50 = 13.2 nM 7.88 Inhibition of recombinant human His-tagged full length BTK expressed in baculovi... 26169764
Blood IC50 = 17.0 nM 7.77 Inhibition of IgM-stimulated CD69 expression in human whole blood 22394077
Tyrosine-protein kinase BTK IC50 = 26.0 nM 7.58 Inhibition of BTK in human whole blood 33932711
Tyrosine-protein kinase BTK IC50 = 27.0 nM 7.57 Inhibition of BTK in human Ramos cells assessed as reduction in IgM-induced calc... 25515957
Tyrosine-protein kinase BTK IC50 = 27.3 nM 7.56 Inhibition of BTK in human Ramos cells after 20 mins by fluorescence assay 25596757
Tyrosine-protein kinase BTK IC50 = 27.3 nM 7.56 Inhibition of BTK in human Ramos cells assessed as inhibition of anti human IgM-... 26169764
Mast cell IC50 = 29.2 nM 7.54 Inhibition of IgE-Fce cross-linking induced histamine release in mast cells 22394077
Tyrosine-protein kinase BTK IC50 = 39.0 nM 7.41 Inhibition of BTK in human PBMC 33932711
STE20-like serine/threonine-protein kinase IC50 = 43.0 nM 7.37 Inhibition of SLK (unknown origin) 29631132
Cytoplasmic tyrosine-protein kinase BMX IC50 = 62.04 nM 7.21 Inhibition of human BMX 33932711
Tyrosine-protein kinase Tec IC50 = 64.0 nM 7.19 Inhibition of TEC (unknown origin) 29631132

Literature References

PubMed DOI Target Context # Activities
25515957 10.1016/j.bmc.2014.11.006 Rattus norvegicus 14
26169764 10.1016/j.bmc.2015.06.023 Rattus norvegicus 5
- 10.6019/CHEMBL5303304 Fibroblast 4
33932711 10.1016/j.bmc.2021.116163 Tyrosine-protein kinase BTK 4
- 10.6019/CHEMBL5303304 U2OS 4
28025004 10.1016/j.bmcl.2016.11.092 Liver 3
26169764 10.1016/j.bmc.2015.06.023 Tyrosine-protein kinase BTK 2
33932711 10.1016/j.bmc.2021.116163 Voltage-gated inwardly rectifying potassium channel KCNH2 2
33932711 10.1016/j.bmc.2021.116163 ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5303304 HEK-293T 2
29631132 10.1016/j.ejmech.2018.03.062 Tyrosine-protein kinase BTK 2
25596757 10.1016/j.bmc.2014.10.043 Tyrosine-protein kinase BTK 2
25515957 10.1016/j.bmc.2014.11.006 Tyrosine-protein kinase BTK 2
- 10.6019/EOS300108 HepG2 1
29631132 10.1016/j.ejmech.2018.03.062 Tyrosine-protein kinase Tec 1
22394077 10.1021/jm300035p Blood 1
22394077 10.1021/jm300035p Rattus norvegicus 1
22394077 10.1021/jm300035p Mus musculus 1
22394077 10.1021/jm300035p Unchecked 1

Data from ChEMBL 36 via Core Engine