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Compound Detail

CHEMBL406821

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Cc1cncc2cccc(S(=O)(=O)N3CCCNC[C@@H]3C)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL406821
Phase Preclinical
Structure Type MOL
InChI Key AWDORCFLUJZUQS-ZDUSSCGKSA-N
7
Targets
20
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

319.4
MW (Da)
1.92
ALogP
4
HBA
1
HBD
62.3
PSA (Ų)
0.92
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H21N3O2S
MW 319.43
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.90

Activity Summary

IC50 12 meas. best 8.3
Ki 8 meas. best 8.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rho-associated protein kinase 2
CHEMBL2973
 Ki 8.8 8.8 1.6 1
Unchecked
CHEMBL612545
 Ki 8.8 6.6767 1.6 3
Rho-associated protein kinase 2
CHEMBL2973
 IC50 8.3 7.8725 5.0 4
Rho-associated protein kinase 1
CHEMBL3231
 IC50 8.3 8.3 5.0 1
Rho-associated protein kinase 1
CHEMBL3231
 Ki 8.22 8.22 6.0 2
Leucine-rich repeat serine/threonine-protein kinase 2
CHEMBL1075104
 IC50 6.98 6.5 104.0 5
cAMP-dependent protein kinase (PKA)
CHEMBL2094138
 Ki 6.47 6.47 340.0 1
NT2
CHEMBL614205
 IC50 5.6 5.6 2500.0 1
Unchecked
CHEMBL612545
 IC50 5.52 5.52 3030.0 1
Myosin light chain kinase, smooth muscle
CHEMBL2428
 Ki 5.0 5.0 10100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rho-associated protein kinase 2 Ki = 1.6 nM 8.8 Inhibition of ROCK2 (unknown origin) assessed as inhibition constant 26486225
Unchecked Ki = 1.6 nM 8.8 Binding affinity at ROCK 18077363
Rho-associated protein kinase 2 IC50 = 5.0 nM 8.3 Inhibition of human recombinant ROCK-2 using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK as... 25248678
Rho-associated protein kinase 1 IC50 = 5.0 nM 8.3 Inhibition of ROCK-1 (unknown origin) 25248678
Rho-associated protein kinase 1 Ki = 6.0 nM 8.22 Inhibition of human ROCK1 by homogenous luciferase assay 20000469
Rho-associated protein kinase 1 Ki = 6.0 nM 8.22 Inhibitory constant against ROCK1 16249185
Rho-associated protein kinase 2 IC50 = 12.0 nM 7.92 Inhibition of human ROCK2 by homogenous luciferase assay 20000469
Rho-associated protein kinase 2 IC50 = 12.0 nM 7.92 Inhibition of human ROCK-2 using S6 peptide as substrate after 5 mins in presenc... 27080184
Rho-associated protein kinase 2 IC50 = 45.0 nM 7.35 Inhibition of His6-tagged ROCK2 (2 to 543 residues) (unknown origin) using pepti... 19740074
Leucine-rich repeat serine/threonine-protein kinase 2 IC50 = 104.0 nM 6.98 Inhibition of GST-tagged LRRK2 G2019S mutant (1326 to 2527 residues) (unknown or... 19740074
Leucine-rich repeat serine/threonine-protein kinase 2 IC50 = 150.0 nM 6.82 Inhibition of GST-tagged LRRK2 G2019S mutant (1326 to 2527 residues) (unknown or... 19740074
Leucine-rich repeat serine/threonine-protein kinase 2 IC50 = 244.0 nM 6.61 Inhibition of GST-tagged LRRK2 (1326 to 2527 residues) (unknown origin) using pe... 19740074
Leucine-rich repeat serine/threonine-protein kinase 2 IC50 = 244.0 nM 6.61 Inhibition of human N-terminal GST-tagged LRRK2 after 1 hr by TR-FRET assay 23721803
cAMP-dependent protein kinase (PKA) Ki = 340.0 nM 6.47 Inhibitory constant against PKA 16249185
Unchecked Ki = 630.0 nM 6.2 Binding affinity at PKA 18077363
NT2 IC50 = 2500.0 nM 5.6 Inhibition of lysophosphatidic acid-induced MARCKS phosphorylation in human NT2 ... 18077363
Unchecked IC50 = 3030.0 nM 5.52 Inhibition of PKA (unknown origin) using cyclic AMP response element binding pro... 27080184
Leucine-rich repeat serine/threonine-protein kinase 2 IC50 = 3300.0 nM 5.48 Inhibition of GST-tagged LRRK2 G2019S/A2016T mutant (1326 to 2527 residues) (unk... 19740074
Unchecked Ki = 9270.0 nM 5.03 Binding affinity at PKC 18077363
Myosin light chain kinase, smooth muscle Ki = 10100.0 nM 5.0 Binding affinity at MLCK 18077363

Literature References

PubMed DOI Target Context # Activities
19740074 10.1042/bj20091035 Leucine-rich repeat serine/threonine-protein kinase 2 10
19740074 10.1042/bj20091035 Unchecked 5
19740074 10.1042/bj20091035 Rho-associated protein kinase 2 4
18077363 10.1073/pnas.0708800104 Unchecked 3
25248678 10.1016/j.bmcl.2014.09.002 Rattus norvegicus 2
18077363 10.1073/pnas.0708800104 Serine/threonine-protein kinase 26 2
19740074 10.1042/bj20091035 cAMP-dependent protein kinase (PKA) 2
19740074 10.1042/bj20091035 Aurora kinase B 2
19740074 10.1042/bj20091035 Serine/threonine-protein kinase BRSK2 2
18077363 10.1073/pnas.0708800104 Ribosomal protein S6 kinase alpha-3 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
17850214 10.1042/bj20070797 Unchecked 2
17850214 10.1042/bj20070797 3-phosphoinositide-dependent protein kinase 1 1
17850214 10.1042/bj20070797 Serine/threonine-protein kinase pim-2 1
17850214 10.1042/bj20070797 Serine/threonine-protein kinase pim-1 1
17850214 10.1042/bj20070797 Serine/threonine-protein kinase PAK 5 1
17850214 10.1042/bj20070797 Serine/threonine-protein kinase PAK 4 1
17850214 10.1042/bj20070797 Mitogen-activated protein kinase 13 1
17850214 10.1042/bj20070797 Mitogen-activated protein kinase 11 1
19740074 10.1042/bj20091035 Ephrin type-B receptor 3 1

Data from ChEMBL 36 via Core Engine