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Compound Detail

CHEMBL4066176

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C[C@@H]1CN(C2COC2)CCN1c1ccc(Nc2cc(-c3ccnc(N4CCn5c(cc6c5CC(C)(C)C6)C4=O)c3CO)cn(C)c2=O)nc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4066176
Phase Preclinical
Structure Type MOL
InChI Key WNEODWDFDXWOLU-HSZRJFAPSA-N
11
Targets
15
Activities
3
Assay Types
2
PK Parameters
18
Publications
0
Known Names

Molecular Properties

664.8
MW (Da)
3.57
ALogP
11
HBA
2
HBD
121.0
PSA (Ų)
0.31
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C37H44N8O4
MW 664.81
Aromatic Rings 4
Heavy Atoms 49
NP-Likeness -0.68

Activity Summary

Kd 11 meas. best 9.62
IC50 3 meas. best 7.7
Ki 1 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase BTK
CHEMBL5251
 Kd 9.62 9.62 0.2 2
Tyrosine-protein kinase BTK
CHEMBL5251
 Ki 8.74 8.74 1.8 1
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 7.7 7.55 20.0 2
Early activation antigen CD69
CHEMBL3308911
 IC50 7.4 7.4 40.0 1
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 Kd 6.92 6.92 120.0 1
Tyrosine-protein kinase ITK/TSK
CHEMBL2959
 Kd 6.72 6.72 190.0 1
Tyrosine-protein kinase Tec
CHEMBL4246
 Kd 6.68 6.68 210.0 1
Tyrosine-protein kinase TXK
CHEMBL4367
 Kd 5.7 5.7 2000.0 1
Tyrosine-protein kinase Blk
CHEMBL2250
 Kd 5.39 5.39 4100.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 Kd 4.64 4.64 23000.0 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
 Kd 4.52 4.52 30000.0 1
Epidermal growth factor receptor
CHEMBL203
 Kd 4.52 4.52 30000.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 Kd 4.52 4.52 30000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase BTK Kd = 0.24 nM 9.62 Binding affinity to wild-type human full length BTK (M1 to S659 residues) expres... 34734694
Tyrosine-protein kinase BTK Kd = 0.24 nM 9.62 Binding affinity to BTK (unknown origin) assessed as dissociation constant by KI... 35041943
Tyrosine-protein kinase BTK Ki = 1.8 nM 8.74 Inhibition of human recombinant C-terminal polyhistidine tagged BTK (1 to 659 re... 29457982
Tyrosine-protein kinase BTK IC50 = 20.0 nM 7.7 Inhibition of BTK phosphorylation in human whole blood assessed as reduction in ... 34734694
Tyrosine-protein kinase BTK IC50 = 40.0 nM 7.4 Inhibition of BTK in human whole blood-derived CD19+ B cells assessed as suppres... 29457982
Early activation antigen CD69 IC50 = 40.0 nM 7.4 Inhibition of CD69 in human whole blood preincubated for 30 mins followed by ant... 34734694
Cytoplasmic tyrosine-protein kinase BMX Kd = 120.0 nM 6.92 Binding affinity to BMX (unknown origin) assessed as dissociation constant by KI... 35041943
Tyrosine-protein kinase ITK/TSK Kd = 190.0 nM 6.72 Binding affinity to ITK (unknown origin) assessed as dissociation constant by KI... 35041943
Tyrosine-protein kinase Tec Kd = 210.0 nM 6.68 Binding affinity to TEC (unknown origin) assessed as dissociation constant by KI... 35041943
Tyrosine-protein kinase TXK Kd = 2000.0 nM 5.7 Binding affinity to TXK (unknown origin) assessed as dissociation constant by KI... 35041943
Tyrosine-protein kinase Blk Kd = 4100.0 nM 5.39 Binding affinity to BLK (unknown origin) assessed as dissociation constant by KI... 35041943
Tyrosine-protein kinase JAK3 Kd = 23000.0 nM 4.64 Binding affinity to JAK3 (unknown origin) assessed as dissociation constant by K... 35041943
Receptor tyrosine-protein kinase erbB-2 Kd = 30000.0 nM 4.52 Binding affinity to ERBB2 (unknown origin) assessed as dissociation constant by ... 35041943
Receptor tyrosine-protein kinase erbB-4 Kd = 30000.0 nM 4.52 Binding affinity to ERBB4 (unknown origin) assessed as dissociation constant by ... 35041943
Epidermal growth factor receptor Kd = 30000.0 nM 4.52 Binding affinity to EGFR (unknown origin) assessed as dissociation constant by K... 35041943

Literature References

PubMed DOI Target Context # Activities
34734694 10.1021/acs.jmedchem.1c00926 Unchecked 9
34734694 10.1021/acs.jmedchem.1c00926 Tyrosine-protein kinase BTK 3
29457982 10.1021/acs.jmedchem.7b01712 Unchecked 2
29457982 10.1021/acs.jmedchem.7b01712 Tyrosine-protein kinase BTK 2
35041943 10.1016/j.bmcl.2022.128549 Receptor tyrosine-protein kinase erbB-4 1
35041943 10.1016/j.bmcl.2022.128549 Tyrosine-protein kinase TXK 1
35041943 10.1016/j.bmcl.2022.128549 Tyrosine-protein kinase Tec 1
35041943 10.1016/j.bmcl.2022.128549 Tyrosine-protein kinase JAK3 1
35041943 10.1016/j.bmcl.2022.128549 Tyrosine-protein kinase ITK/TSK 1
35041943 10.1016/j.bmcl.2022.128549 Epidermal growth factor receptor 1
35041943 10.1016/j.bmcl.2022.128549 Tyrosine-protein kinase BTK 1
35041943 10.1016/j.bmcl.2022.128549 Cytoplasmic tyrosine-protein kinase BMX 1
35041943 10.1016/j.bmcl.2022.128549 Tyrosine-protein kinase Blk 1
35041943 10.1016/j.bmcl.2022.128549 Receptor tyrosine-protein kinase erbB-2 1
34734694 10.1021/acs.jmedchem.1c00926 Early activation antigen CD69 1
29457982 10.1021/acs.jmedchem.7b01712 ADMET 1
29457982 10.1021/acs.jmedchem.7b01712 Liver 1
29457982 10.1021/acs.jmedchem.7b01712 No relevant target 1

Data from ChEMBL 36 via Core Engine