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Compound Detail

CHEMBL104264

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O=S(=O)(NCCNC/C=C/c1ccc(Br)cc1)c1cccc2cnccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL104264
Phase Preclinical
Structure Type MOL
InChI Key ZKZXNDJNWUTGDK-NSCUHMNNSA-N
22
Targets
63
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

446.4
MW (Da)
3.58
ALogP
4
HBA
2
HBD
71.1
PSA (Ų)
0.52
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H20BrN3O2S
MW 446.37
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.06

Activity Summary

IC50 49 meas. best 7.14
Ki 12 meas. best 7.32
Kd 2 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Kd 7.77 7.77 17.0 1
Rho-associated protein kinase 2
CHEMBL2973
 Kd 7.62 7.62 24.0 1
Unchecked
CHEMBL612545
 Ki 7.32 6.0467 48.0 3
cAMP-dependent protein kinase (PKA)
CHEMBL2094138
 IC50 7.14 5.47 73.0 8
Ribosomal protein S6 kinase beta-1
CHEMBL4501
 IC50 7.1 7.1 80.0 1
Ribosomal protein S6 kinase alpha-5
CHEMBL4237
 IC50 6.92 6.92 120.0 1
Unchecked
CHEMBL612545
 IC50 6.87 5.7517 135.0 6
RAC-gamma serine/threonine-protein kinase
CHEMBL4816
 IC50 6.7 6.7 200.0 1
Rho-associated protein kinase 2
CHEMBL5490
 IC50 6.57 6.57 270.0 1
Rho-associated protein kinase 2
CHEMBL2973
 IC50 6.57 6.005 270.0 2
RAC-beta serine/threonine-protein kinase
CHEMBL2431
 IC50 6.52 6.3025 300.0 4
cAMP-dependent protein kinase A
CHEMBL2111446
 Ki 6.32 6.32 480.0 1
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 IC50 5.8 5.6983 1600.0 6
Plasmodium falciparum
CHEMBL364
 IC50 5.68 5.1222 2100.0 9
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 Ki 5.35 5.35 4500.0 1
OVCAR-8
CHEMBL612555
 IC50 4.98 4.98 10500.0 2
HL-60
CHEMBL383
 IC50 4.94 4.94 11400.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.82 4.7967 15000.0 3
Glycogen synthase kinase-3 beta
CHEMBL262
 IC50 4.82 4.82 15000.0 1
HCT-116
CHEMBL394
 IC50 4.8 4.8 15700.0 2
Myosin light chain kinase, smooth muscle
CHEMBL3062
 Ki 4.55 4.55 28300.0 1
Myosin light chain kinase, smooth muscle
CHEMBL2428
 Ki 4.55 4.55 28300.0 1
Calcium/calmodulin-dependent protein kinase kinase 2
CHEMBL5284
 Ki 4.53 4.53 29700.0 1
Protein kinase C (PKC)
CHEMBL2093867
 Ki 4.5 4.5 31700.0 1
Casein kinase I isoform alpha
CHEMBL2793
 Ki 4.42 4.42 38300.0 1
Casein kinase I
CHEMBL2111458
 Ki 4.42 4.42 38300.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Kd = 17.0 nM 7.77 Displacement of fluorescent-ARC-1063 from recombinant bovine PKAc by luminescenc... 22521647
Rho-associated protein kinase 2 Kd = 24.0 nM 7.62 Displacement of fluorescent-ARC-1063 from His6-tagged recombinant human ROCK2 by... 22521647
Unchecked Ki = 48.0 nM 7.32 Binding affinity at PKA 18077363
cAMP-dependent protein kinase (PKA) IC50 = 73.0 nM 7.14 Inhibition of PKA by radiometric filter binding assay 17451235
Ribosomal protein S6 kinase beta-1 IC50 = 80.0 nM 7.1 Inhibition of His-tagged human S6K1 expressed in Escherichia coli 10998351
Ribosomal protein S6 kinase alpha-5 IC50 = 120.0 nM 6.92 Inhibition of His-tagged human MSK1 expressed in Sf9 cells 10998351
Unchecked IC50 = 135.0 nM 6.87 Inhibition of bovine heart PKA 10998351
Unchecked IC50 = 135.0 nM 6.87 Inhibition of cAMP dependent Protein kinase A (PKA) catalytic subunit from bovin... 12941328
RAC-gamma serine/threonine-protein kinase IC50 = 200.0 nM 6.7 Inhibition of AKT3 by FRET based assay 19604696
Rho-associated protein kinase 2 IC50 = 270.0 nM 6.57 Inhibition of ROCK2 18077363
Rho-associated protein kinase 2 IC50 = 270.0 nM 6.57 Inhibition of rat ROCK2 expressed in Sf9 cells 10998351
RAC-beta serine/threonine-protein kinase IC50 = 300.0 nM 6.52 Inhibition of AKT2 by FRET based assay 19604696
Unchecked Ki = 480.0 nM 6.32 Inhibitory constant against cGPK (PKG) 8824261
cAMP-dependent protein kinase A Ki = 480.0 nM 6.32 Inhibitory constant against bovine cAPK (PKA) 8824261
RAC-beta serine/threonine-protein kinase IC50 = 590.0 nM 6.23 Inhibition of PKBbeta by radiometric filter binding assay 20151677
RAC-beta serine/threonine-protein kinase IC50 = 590.0 nM 6.23 Inhibition of PKBbeta recombinant by radiometric filter binding assay 18345609
RAC-beta serine/threonine-protein kinase IC50 = 590.0 nM 6.23 Inhibition of PKBbeta by radiometric filter binding assay 17451235
Unchecked IC50 = 940.0 nM 6.03 Inhibition of PKA 18346896
cAMP-dependent protein kinase (PKA) IC50 = 1200.0 nM 5.92 Inhibition of PKA-mediated phosphorylation of kemptide at 100 uM 16890431
RAC-alpha serine/threonine-protein kinase IC50 = 1600.0 nM 5.8 Inhibition of AKT1 by FRET based assay 19604696

Literature References

PubMed DOI Target Context # Activities
26254279 10.18632/oncotarget.4214 cAMP-dependent protein kinase (PKA) 9
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
10998351 10.1042/0264-6021:3510095 Unchecked 6
23398362 10.1042/bj20121418 Cyclin-dependent kinase 5/CDK5 activator 1 4
23398362 10.1042/bj20121418 Insulin-like growth factor 1 receptor 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23398362 10.1042/bj20121418 Tyrosine-protein kinase HCK 4
23398362 10.1042/bj20121418 Insulin receptor 4
23398362 10.1042/bj20121418 Protein kinase C beta type 4
23398362 10.1042/bj20121418 cGMP-dependent protein kinase 1 4
23398362 10.1042/bj20121418 Tyrosine-protein kinase Lck 4
23398362 10.1042/bj20121418 Serine/threonine-protein kinase mTOR 4
19604696 10.1016/j.bmcl.2009.06.078 RAC-beta serine/threonine-protein kinase 3
22521647 10.1016/j.bmcl.2012.03.101 Unchecked 3
18077363 10.1073/pnas.0708800104 Calcium/calmodulin-dependent protein kinase kinase 2 2
22607683 10.1016/j.bmcl.2012.04.082 Unchecked 2
23398362 10.1042/bj20121418 Serine/threonine-protein kinase Nek7 2
23398362 10.1042/bj20121418 Serine/threonine-protein kinase MARK1 2
22521647 10.1016/j.bmcl.2012.03.101 Rho-associated protein kinase 2 2
23398362 10.1042/bj20121418 Serine/threonine-protein kinase Nek6 2

Data from ChEMBL 36 via Core Engine