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Compound Detail

CHEMBL4443342

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COc1cc(Nc2ccnc3ccc(Br)cc23)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4443342
Phase Preclinical
Structure Type MOL
InChI Key AUOSKLDNVNGKRR-UHFFFAOYSA-N
13
Targets
36
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

389.2
MW (Da)
4.77
ALogP
5
HBA
1
HBD
52.6
PSA (Ų)
0.68
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C18H17BrN2O3
MW 389.25
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -0.74

Activity Summary

Kd 19 meas. best 8.72
IC50 11 meas. best 7.32
Ki 4 meas. best 8.51
EC50 2 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cyclin-G-associated kinase
CHEMBL4355
 Kd 8.72 8.5067 1.9 6
Cyclin-G-associated kinase
CHEMBL4355
 Ki 8.51 8.51 3.1 2
Cyclin-G-associated kinase
CHEMBL4355
 IC50 7.32 6.9917 48.0 6
dengue virus type 2
CHEMBL613966
 EC50 7.1 7.005 80.0 2
Receptor-interacting serine/threonine-protein kinase 2
CHEMBL5014
 Kd 6.96 6.96 110.0 3
CWR22R
CHEMBL612657
 IC50 6.77 6.77 170.0 1
Atypical kinase COQ8A, mitochondrial
CHEMBL5550
 Kd 6.72 6.6733 190.0 3
Receptor-interacting serine/threonine-protein kinase 2
CHEMBL5014
 IC50 6.44 6.44 360.0 2
Serine/threonine-protein kinase NLK
CHEMBL5364
 Kd 6.28 6.28 520.0 3
LNCaP
CHEMBL612518
 IC50 6.19 6.19 650.0 1
Ephrin type-B receptor 6
CHEMBL5836
 Kd 6.15 6.15 710.0 1
Activin receptor type-1
CHEMBL5903
 Kd 6.01 6.005 980.0 2
Tyrosine-protein kinase ABL1
CHEMBL1862
 Kd 5.92 5.92 1200.0 1
Unchecked
CHEMBL612545
 IC50 4.96 4.96 11000.0 1
Serine/threonine-protein kinase 16
CHEMBL3938
 Ki 4.29 4.29 51000.0 1
AP2-associated protein kinase 1
CHEMBL3830
 Ki 4.28 4.28 53000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cyclin-G-associated kinase Kd = 1.9 nM 8.72 Affinity Biochemical interaction (Competition binding assay (DiscoverX)) EUB0000... -
Cyclin-G-associated kinase Kd = 1.9 nM 8.72 Binding affinity to biotinylated human GAK (13 to 338 residues) expressed in Esc... 30768268
Cyclin-G-associated kinase Kd = 3.1 nM 8.51 Binding affinity to GAK (unknown origin) assessed as dissociation constant 33970631
Cyclin-G-associated kinase Ki = 3.1 nM 8.51 Selectivity interaction (Enzymatic assay) EUB0000207b GAK -
Cyclin-G-associated kinase Ki = 3.1 nM 8.51 Binding affinity to C-terminal AVI-tagged GAK (unknown origin) (12 to 347 residu... 30768268
Cyclin-G-associated kinase Kd = 4.1 nM 8.39 Binding affinity to human wild type partial length GAK (G13 to Y338 residues) ex... 31129055
Cyclin-G-associated kinase Kd = 4.5 nM 8.35 Binding affinity to GAK (unknown origin) by ITC assay 30768268
Cyclin-G-associated kinase Kd = 4.5 nM 8.35 Selectivity interaction (ITC) EUB0000207b GAK -
Cyclin-G-associated kinase IC50 = 48.0 nM 7.32 Inhibition of tracer 5 binding to human N-terminal nano luciferase-fused GAK exp... 30973735
Cyclin-G-associated kinase IC50 = 48.0 nM 7.32 Inhibition of NanoBRET tracer 5 binding to NL-fused GAK (unknown origin) express... 33497888
dengue virus type 2 EC50 = 80.0 nM 7.1 Antiviral activity against DENV2 New Guinea C strain infected in Huh7 cells afte... 32631507
Receptor-interacting serine/threonine-protein kinase 2 Kd = 110.0 nM 6.96 Binding affinity to biotinylated human RIPK2 (1 to 310 residues) expressed in Es... 30768268
Receptor-interacting serine/threonine-protein kinase 2 Kd = 110.0 nM 6.96 Binding affinity to wild-type human partial length RIPK2 (M1 to K310 residues) e... 31129055
Receptor-interacting serine/threonine-protein kinase 2 Kd = 110.0 nM 6.96 Selectivity interaction (KinomeScan (DiscoverX, competition-binding assay)) EUB0... -
Cyclin-G-associated kinase IC50 = 120.0 nM 6.92 Affinity On-target Cellular interaction (NanoBRET assay (HEK293T cells)) EUB0000... -
Cyclin-G-associated kinase IC50 = 120.0 nM 6.92 Displacement of fluorescent tracer from N-terminus of human GAK expressed in HEK... 30768268
dengue virus type 2 EC50 = 122.0 nM 6.91 Antiviral activity against DENV2 New Guinea C strain infected in Huh7 cells afte... 32631507
CWR22R IC50 = 170.0 nM 6.77 Cytotoxicity against human 22Rv1 cells after 72 hrs by MTS assay 30768268
Cyclin-G-associated kinase IC50 = 170.0 nM 6.77 Affinity Phenotypic Cellular interaction (Cell viability assay (CellTiter-Glo as... -
Atypical kinase COQ8A, mitochondrial Kd = 190.0 nM 6.72 Binding affinity to biotinylated full length human ADCK3 expressed in Escherichi... 30768268

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 U2OS 262
- 10.6019/CHEMBL4689842 HEK-293T 260
- 10.6019/CHEMBL4689842 Fibroblast 260
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724696 U2OS 8
30768268 10.1021/acs.jmedchem.8b01213 Cyclin-G-associated kinase 7
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
31378571 10.1016/j.bmcl.2019.07.012 Mycobacterium tuberculosis 5
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
30768268 10.1021/acs.jmedchem.8b01213 Receptor-interacting serine/threonine-protein kinase 2 3
32631507 10.1016/j.bmcl.2020.127284 dengue virus type 2 3
30768268 10.1021/acs.jmedchem.8b01213 CWR22R 3
30973735 10.1021/acs.jmedchem.9b00350 Unchecked 3
- 10.6019/CHEMBL5212743 Cyclin-G-associated kinase 3
30768268 10.1021/acs.jmedchem.8b01213 Unchecked 2
- 10.6019/CHEMBL5212743 Receptor-interacting serine/threonine-protein kinase 2 2
30768268 10.1021/acs.jmedchem.8b01213 LNCaP 2
30973735 10.1021/acs.jmedchem.9b00350 Epidermal growth factor receptor 2
31129055 10.1016/j.bmcl.2019.05.025 Cyclin-G-associated kinase 2

Data from ChEMBL 36 via Core Engine