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Compound Detail

CHEMBL4077064

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C=CC(=O)N1CCc2ccc(-n3c(=O)ccc4cnc5ccc(-c6cnn(C)c6)cc5c43)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4077064
Phase Preclinical
Structure Type MOL
InChI Key RTRNJQOBEOISFQ-UHFFFAOYSA-N
8
Targets
22
Activities
3
Assay Types
1
PK Parameters
18
Publications
0
Known Names

Molecular Properties

447.5
MW (Da)
4.01
ALogP
6
HBA
0
HBD
73.0
PSA (Ų)
0.31
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H21N5O2
MW 447.50
Aromatic Rings 5
Heavy Atoms 34
NP-Likeness -1.15

Activity Summary

IC50 18 meas. best 8.18
EC50 2 meas. best 6.5
Ki 2 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 8.18 8.11 6.6 5
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 IC50 8.17 7.94 6.7 4
Tyrosine-protein kinase BTK
CHEMBL5251
 Ki 7.85 7.85 14.2 2
Tyrosine-protein kinase Tec
CHEMBL4246
 IC50 6.71 6.71 195.0 1
Tyrosine-protein kinase BTK
CHEMBL5251
 EC50 6.5 6.41 318.0 2
Tyrosine-protein kinase Blk
CHEMBL2250
 IC50 6.44 6.44 366.0 2
Unchecked
CHEMBL612545
 IC50 6.16 6.16 690.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 6.06 6.06 874.0 1
Serine/threonine-protein kinase mTOR
CHEMBL2842
 IC50 5.92 5.92 1200.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 5.48 5.3533 3336.0 3

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.02 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Tyrosine-protein kinase BTK IC50 = 6.59 nM 8.18 Inhibition of recombinant full length His-tagged human BTK expressed in baculovi... 28628824
Cytoplasmic tyrosine-protein kinase BMX IC50 = 6.73 nM 8.17 Inhibition of recombinant full length His-tagged human BMX expressed in baculovi... 28628824
Cytoplasmic tyrosine-protein kinase BMX IC50 = 6.73 nM 8.17 In vitro Kinase Assay: Purified BMX was mixed with substrate (FAK or Bmxtides), ... -
Tyrosine-protein kinase BTK IC50 = 7.0 nM 8.15 Inhibition of BTK (unknown origin) 30077608
Tyrosine-protein kinase BTK IC50 = 7.0 nM 8.15 Inhibition of BTK (unknown origin) 28986130
Tyrosine-protein kinase BTK IC50 = 7.0 nM 8.15 Binding Assay: DiscoverX binding assays were performed according to published me... -
Cytoplasmic tyrosine-protein kinase BMX IC50 = 7.0 nM 8.15 Binding Assay: DiscoverX binding assays were performed according to published me... -
Tyrosine-protein kinase BTK IC50 = 12.0 nM 7.92 Inhibition of full length recombinant human N-terminal His tagged BKT expressed ... 28315597
Tyrosine-protein kinase BTK Ki = 14.2 nM 7.85 Irreversible inhibition of recombinant full length His-tagged human BTK expresse... 28628824
Tyrosine-protein kinase BTK Ki = 14.2 nM 7.85 Reversible inhibition of full length recombinant human N-terminal His tagged BKT... 28315597
Cytoplasmic tyrosine-protein kinase BMX IC50 = 54.0 nM 7.27 Inhibition of full length recombinant human N-terminal GST-tagged BMX expressed ... 28315597
Tyrosine-protein kinase Tec IC50 = 195.0 nM 6.71 Binding Assay: DiscoverX binding assays were performed according to published me... -
Tyrosine-protein kinase BTK EC50 = 318.0 nM 6.5 Inhibition of BTK in human Ramos cells assessed as reduction in PLCgamma2 phosph... 28986130
Tyrosine-protein kinase Blk IC50 = 366.0 nM 6.44 Inhibition of recombinant full length His-tagged human BLK expressed in baculovi... 28628824
Tyrosine-protein kinase Blk IC50 = 366.0 nM 6.44 Binding Assay: DiscoverX binding assays were performed according to published me... -
Tyrosine-protein kinase BTK EC50 = 475.0 nM 6.32 Inhibition of 3x-FLAG-tagged BTK (unknown origin) expressed in HEK293T cells ass... 28986130
Unchecked IC50 = 690.0 nM 6.16 Inhibition of PI3K (unknown origin) 30077608
Epidermal growth factor receptor IC50 = 874.0 nM 6.06 Inhibition of recombinant human N-terminal GST-tagged wild-type EGFR (695 to end... 28315597
Serine/threonine-protein kinase mTOR IC50 = 1200.0 nM 5.92 Binding Assay: DiscoverX binding assays were performed according to published me... -
Tyrosine-protein kinase JAK3 IC50 = 3336.0 nM 5.48 Inhibition of recombinant human N-terminal GST-tagged JAK3 (781 to end residues)... 28315597

Literature References

PubMed DOI Target Context # Activities
28337328 10.1021/acsmedchemlett.7b00008 dengue virus type 2 5
28315597 10.1016/j.ejmech.2017.03.001 Tyrosine-protein kinase BTK 4
28628824 10.1016/j.ejmech.2017.06.016 Tyrosine-protein kinase BTK 4
28986130 10.1016/j.ejmech.2017.09.024 Tyrosine-protein kinase BTK 3
28337328 10.1021/acsmedchemlett.7b00008 Unchecked 2
28337328 10.1021/acsmedchemlett.7b00008 ADMET 1
32352776 10.1021/acs.jmedchem.0c00093 Tyrosine-protein kinase BTK 1
30077608 10.1016/j.bmc.2018.07.047 Unchecked 1
30077608 10.1016/j.bmc.2018.07.047 Tyrosine-protein kinase BTK 1
28628824 10.1016/j.ejmech.2017.06.016 Tyrosine-protein kinase JAK3 1
28628824 10.1016/j.ejmech.2017.06.016 Tyrosine-protein kinase Blk 1
28628824 10.1016/j.ejmech.2017.06.016 Cytoplasmic tyrosine-protein kinase BMX 1
28337328 10.1021/acsmedchemlett.7b00008 Vesicular stomatitis Indiana virus 1
28337328 10.1021/acsmedchemlett.7b00008 Enterovirus C 1
28337328 10.1021/acsmedchemlett.7b00008 Huh-7 1
28315597 10.1016/j.ejmech.2017.03.001 Cytoplasmic tyrosine-protein kinase BMX 1
28315597 10.1016/j.ejmech.2017.03.001 Tyrosine-protein kinase JAK3 1
28315597 10.1016/j.ejmech.2017.03.001 Epidermal growth factor receptor 1

Data from ChEMBL 36 via Core Engine