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Compound Detail

CHEMBL4114929

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COc1cc(C(=O)Nc2cc(C(F)(F)F)ccn2)ccc1-c1nc([C@@H]2CC[C@H]3CCC(=O)N3C2)n2ccnc(N)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4114929
Phase Preclinical
Structure Type MOL
InChI Key OMIQRSKHABIPRH-AEFFLSMTSA-N
16
Targets
20
Activities
1
Assay Types
12
PK Parameters
19
Publications
0
Known Names

Molecular Properties

565.6
MW (Da)
4.52
ALogP
8
HBA
2
HBD
127.7
PSA (Ų)
0.36
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H26F3N7O3
MW 565.56
Aromatic Rings 4
Heavy Atoms 41
NP-Likeness -0.98

Activity Summary

IC50 20 meas. best 9.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 9.72 8.87 0.2 5
Tyrosine-protein kinase Srms
CHEMBL5703
 IC50 7.8 7.8 16.0 1
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 IC50 7.72 7.72 19.0 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 7.58 7.58 26.0 1
Tyrosine-protein kinase Yes
CHEMBL2073
 IC50 7.27 7.27 54.0 1
Tyrosine-protein kinase Fgr
CHEMBL4454
 IC50 7.19 7.19 64.0 1
Tyrosine-protein kinase Tec
CHEMBL4246
 IC50 7.17 7.17 67.0 1
Proto-oncogene tyrosine-protein kinase Src
CHEMBL267
 IC50 7.15 7.15 71.0 1
Protein-tyrosine kinase 6
CHEMBL4601
 IC50 7.08 7.08 84.0 1
Tyrosine-protein kinase Blk
CHEMBL2250
 IC50 7.0 7.0 101.0 1
Tyrosine-protein kinase TXK
CHEMBL4367
 IC50 6.99 6.99 102.0 1
Tyrosine-protein kinase FRK
CHEMBL4223
 IC50 6.81 6.81 154.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 6.8 6.8 160.0 1
Tyrosine-protein kinase Lyn
CHEMBL3905
 IC50 6.79 6.79 162.0 1
Tyrosine-protein kinase CSK
CHEMBL2634
 IC50 6.64 6.64 227.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
 IC50 5.91 5.91 1230.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 622.12 ng.hr.mL-1 Rattus norvegicus
AUC 904.9 ng.hr.mL-1 Canis lupus familiaris
CL 53.0 mL.min-1.kg-1 Rattus norvegicus
CL 20.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 50.0 nM Rattus norvegicus
Cmax 1100.0 nM Canis lupus familiaris
F 9.5 % Rattus norvegicus
F 108.0 % Canis lupus familiaris
T1/2 3.0 hr Rattus norvegicus
T1/2 3.4 hr Canis lupus familiaris
Tmax 2.1 hr Rattus norvegicus
Tmax 1.5 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase BTK IC50 = 0.19 nM 9.72 LANCE (Lanthanide Chelate Excite) TR-FRET (Time-resolved fluorescence resonance ... -
Tyrosine-protein kinase BTK IC50 = 0.21 nM 9.68 Inhibition of recombinant full length BTK (unknown origin) expressed in baculovi... 32738973
Tyrosine-protein kinase BTK IC50 = 0.22 nM 9.66 LANCE (Lanthanide Chelate Excite) TR-FRET (Time-resolved fluorescence resonance ... -
Tyrosine-protein kinase Srms IC50 = 16.0 nM 7.8 Inhibition of SRMS (unknown origin) 32738973
Tyrosine-protein kinase BTK IC50 = 17.0 nM 7.77 Inhibition of BTK in human PBMC assessed as reduction in cell surface CD69 expre... 32738973
Cytoplasmic tyrosine-protein kinase BMX IC50 = 19.0 nM 7.72 Inhibition of BMX (unknown origin) 32738973
Tyrosine-protein kinase Lck IC50 = 26.0 nM 7.58 Inhibition of LCK (unknown origin) 32738973
Tyrosine-protein kinase BTK IC50 = 30.0 nM 7.52 Inhibition of BTK in human whole blood assessed as reduction in cell surface CD6... 32738973
Tyrosine-protein kinase Yes IC50 = 54.0 nM 7.27 Inhibition of YES1 (unknown origin) 32738973
Tyrosine-protein kinase Fgr IC50 = 64.0 nM 7.19 Inhibition of FGR (unknown origin) 32738973
Tyrosine-protein kinase Tec IC50 = 67.0 nM 7.17 Inhibition of TEC (unknown origin) 32738973
Proto-oncogene tyrosine-protein kinase Src IC50 = 71.0 nM 7.15 Inhibition of SRC (unknown origin) 32738973
Protein-tyrosine kinase 6 IC50 = 84.0 nM 7.08 Inhibition of PTK6 (unknown origin) 32738973
Tyrosine-protein kinase Blk IC50 = 101.0 nM 7.0 Inhibition of BLK (unknown origin) 32738973
Tyrosine-protein kinase TXK IC50 = 102.0 nM 6.99 Inhibition of TXK (unknown origin) 32738973
Tyrosine-protein kinase FRK IC50 = 154.0 nM 6.81 Inhibition of FRK (unknown origin) 32738973
Receptor tyrosine-protein kinase erbB-4 IC50 = 160.0 nM 6.8 Inhibition of ERBB4 (unknown origin) 32738973
Tyrosine-protein kinase Lyn IC50 = 162.0 nM 6.79 Inhibition of LYNB (unknown origin) 32738973
Tyrosine-protein kinase CSK IC50 = 227.0 nM 6.64 Inhibition of CSK (unknown origin) 32738973
Tyrosine-protein kinase Fyn IC50 = 1230.0 nM 5.91 Inhibition of FYN (unknown origin) 32738973

Literature References

PubMed DOI Target Context # Activities
32738973 10.1016/j.bmcl.2020.127390 Unchecked 15
32738973 10.1016/j.bmcl.2020.127390 ADMET 14
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase BTK 3
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Lyn 1
32738973 10.1016/j.bmcl.2020.127390 Rattus norvegicus 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Yes 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase TXK 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Tec 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Srms 1
32738973 10.1016/j.bmcl.2020.127390 Proto-oncogene tyrosine-protein kinase Src 1
32738973 10.1016/j.bmcl.2020.127390 Protein-tyrosine kinase 6 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Lck 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Fyn 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase FRK 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Fgr 1
32738973 10.1016/j.bmcl.2020.127390 Receptor tyrosine-protein kinase erbB-4 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase CSK 1
32738973 10.1016/j.bmcl.2020.127390 Cytoplasmic tyrosine-protein kinase BMX 1
32738973 10.1016/j.bmcl.2020.127390 Tyrosine-protein kinase Blk 1

Data from ChEMBL 36 via Core Engine