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Compound Detail

CHEMBL4448806

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COc1cccc([C@@H](C)NC(=O)c2ccc(-c3ccncc3)cc2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4448806
Phase Preclinical
Structure Type MOL
InChI Key JRVSFZKYQCETAH-OAHLLOKOSA-N
8
Targets
13
Activities
1
Assay Types
30
PK Parameters
16
Publications
0
Known Names

Molecular Properties

332.4
MW (Da)
4.25
ALogP
3
HBA
1
HBD
51.2
PSA (Ų)
0.76
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H20N2O2
MW 332.40
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.07

Activity Summary

IC50 13 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rho-associated protein kinase 2
CHEMBL2973
 IC50 9.0 8.9 1.0 3
Rho-associated protein kinase 1
CHEMBL3231
 IC50 9.0 8.385 1.0 2
cGMP-dependent protein kinase 1
CHEMBL4273
 IC50 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 IC50 8.05 7.3333 9.0 3
Rho-associated protein kinase
CHEMBL2111459
 IC50 7.92 7.92 12.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 7.1 7.1 80.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.19 6.19 640.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.44 5.44 3620.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2190.0 ng.hr.mL-1 Rattus norvegicus
AUC 1800.0 ng.hr.mL-1 Rattus norvegicus
AUC 2630.0 ng.hr.mL-1 Rattus norvegicus
AUC 850.0 ng.hr.mL-1 Rattus norvegicus
AUC 2080.0 ng.hr.mL-1 Mus musculus
AUC 1420.0 ng.hr.mL-1 Mus musculus
AUC 1780.0 ng.hr.mL-1 Mus musculus
CL 25.0 mL.min-1.kg-1 Rattus norvegicus
CL 176.0 mL.min-1.kg-1 Mus musculus
Cmax 3098.68 nM Rattus norvegicus
Cmax 5776.17 nM Rattus norvegicus
Cmax 1263.54 nM Rattus norvegicus
Cmax 4993.98 nM Mus musculus
Cmax 2527.08 nM Mus musculus
Cmax 2978.34 nM Mus musculus
F 82.0 % Rattus norvegicus
F 39.0 % Rattus norvegicus
Fu 0.831 - Not specified
T1/2 1.5 hr Rattus norvegicus
T1/2 0.8 hr Rattus norvegicus
T1/2 1.2 hr Rattus norvegicus
T1/2 1.1 hr Rattus norvegicus
T1/2 1.5 hr Mus musculus
T1/2 2.0 hr Mus musculus
T1/2 1.8 hr Mus musculus
Tmax 0.25 hr Rattus norvegicus
Tmax 0.25 hr Rattus norvegicus
Tmax 0.67 hr Rattus norvegicus
Tmax 0.42 hr Mus musculus
Tmax 0.33 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rho-associated protein kinase 1 IC50 = 1.0 nM 9.0 Inhibition of ROCK1 (unknown origin) incubated for 2 hrs by AbbVie kinase panel ... 30384606
Rho-associated protein kinase 2 IC50 = 1.0 nM 9.0 Inhibition of ROCK2 (unknown origin) incubated for 2 hrs by AbbVie kinase panel ... 30384606
cGMP-dependent protein kinase 1 IC50 = 1.0 nM 9.0 Inhibition of PKG1A (unknown origin) incubated for 2 hrs by AbbVie kinase panel ... 30384606
Rho-associated protein kinase 2 IC50 = 1.0 nM 9.0 Inhibition of recombinant N-terminal GST-tagged human ROCK2 (5 to 554 residues) ... 35816678
Rho-associated protein kinase 2 IC50 = 2.0 nM 8.7 Inhibition of GST-fused human recombinant ROCK2 (11 to 552 residues) expressed i... 30384606
Unchecked IC50 = 9.0 nM 8.05 Inhibition of ROCK in rat A7R5 cells assessed as cofilin serine 3 phosphorylatio... 35816678
Rho-associated protein kinase IC50 = 12.0 nM 7.92 Inhibition of ROCK1/2 in human PANC1 cells assessed as reduction in MYPT1 phosph... 30384606
Rho-associated protein kinase 1 IC50 = 17.0 nM 7.77 Inhibition of human GST-tagged catalytic ROCK1 expressed in baculovirus system u... 30384606
Unchecked IC50 = 47.0 nM 7.33 Inhibition of PKA (unknown origin) incubated for 2 hrs by AbbVie kinase panel as... 30384606
Cytochrome P450 3A4 IC50 = 80.0 nM 7.1 Inhibition of C-terminal 4His-tagged CYP3A4 (unknown origin) expressed in Escher... 30384606
Unchecked IC50 = 240.0 nM 6.62 Inhibition of PKA (unknown origin) 30384606
Cytochrome P450 2C9 IC50 = 640.0 nM 6.19 Inhibition of C-terminal 4His-tagged CYP2C9 (unknown origin) expressed in Escher... 30384606
Cytochrome P450 2D6 IC50 = 3620.0 nM 5.44 Inhibition of C-terminal 4His-tagged CYP2D6 (unknown origin) expressed in Escher... 30384606

Literature References

PubMed DOI Target Context # Activities
30384606 10.1021/acs.jmedchem.8b01098 ADMET 31
35816678 10.1021/acs.jmedchem.2c00474 ADMET 3
30384606 10.1021/acs.jmedchem.8b01098 Rho-associated protein kinase 1 2
30384606 10.1021/acs.jmedchem.8b01098 Rho-associated protein kinase 2 2
30384606 10.1021/acs.jmedchem.8b01098 Unchecked 2
30384606 10.1021/acs.jmedchem.8b01098 No relevant target 2
30384606 10.1021/acs.jmedchem.8b01098 Cytochrome P450 2C9 1
30384606 10.1021/acs.jmedchem.8b01098 Cytochrome P450 2D6 1
30384606 10.1021/acs.jmedchem.8b01098 Cytochrome P450 3A4 1
30384606 10.1021/acs.jmedchem.8b01098 Rho-associated protein kinase 1
30384606 10.1021/acs.jmedchem.8b01098 Rattus norvegicus 1
30384606 10.1021/acs.jmedchem.8b01098 cGMP-dependent protein kinase 1 1
35816678 10.1021/acs.jmedchem.2c00474 Rho-associated protein kinase 2 1
35816678 10.1021/acs.jmedchem.2c00474 Unchecked 1
35816678 10.1021/acs.jmedchem.2c00474 No relevant target 1
35816678 10.1021/acs.jmedchem.2c00474 cGMP-dependent protein kinase 1 1

Data from ChEMBL 36 via Core Engine