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Compound Detail

CHEMBL3410036

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Cc1c[nH]c2ncnc(-c3ccc(NC(=O)N(CCO)c4ccccc4)cc3)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3410036
Phase Preclinical
Structure Type MOL
InChI Key WQAGVQVBDHOHRD-UHFFFAOYSA-N
6
Targets
12
Activities
1
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

387.4
MW (Da)
3.96
ALogP
4
HBA
3
HBD
94.1
PSA (Ų)
0.48
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H21N5O2
MW 387.44
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -1.16

Activity Summary

IC50 12 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
LIM domain kinase 2
CHEMBL5932
 IC50 7.62 6.5333 24.0 3
LIM domain kinase 1
CHEMBL3836
 IC50 7.37 6.598 43.0 5
LIM domain kinase 1
CHEMBL3407314
 IC50 6.33 6.33 470.0 1
LIM domain kinase 1/2
CHEMBL3885599
 IC50 6.33 6.33 467.7 1
Rho-associated protein kinase 1
CHEMBL3231
 IC50 5.26 5.26 5536.0 1
Rho-associated protein kinase 2
CHEMBL2973
 IC50 5.18 5.18 6565.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3254.5 ng.hr.mL-1 Rattus norvegicus
CL 5.2 mL.min-1.kg-1 Rattus norvegicus
CL 18.0 mL.min-1.g-1 Rattus norvegicus
CL 8.0 mL.min-1.g-1 Homo sapiens
CL 0.0042 mL.min-1.kg-1 Rattus norvegicus
Cmax 7700.0 nM Rattus norvegicus
F 36.0 % Rattus norvegicus
F 36.0 % Rattus norvegicus
T1/2 1.45 hr Homo sapiens
T1/2 0.5 hr Rattus norvegicus
T1/2 2.2 hr Rattus norvegicus
T1/2 2.2 hr Rattus norvegicus
Vd 0.4 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
LIM domain kinase 2 IC50 = 24.0 nM 7.62 Inhibition of LIMK2 (unknown origin) 36136092
LIM domain kinase 1 IC50 = 43.0 nM 7.37 Inhibition of human Limk1 using cofilin substrate, ATP and [gamma33P]ATP 25621531
LIM domain kinase 1 IC50 = 43.0 nM 7.37 Inhibition of LIMK1 (unknown origin) 36136092
LIM domain kinase 1 IC50 = 371.54 nM 6.43 Inhibition of recombinant LIMK1 (330 to 637 residues) (unknown origin) incubated... 36205722
LIM domain kinase 1 IC50 = 470.0 nM 6.33 Inhibition of Limk1 in rat A7r5 cells assessed as reduction in cofilin phosphory... 25621531
LIM domain kinase 1/2 IC50 = 467.74 nM 6.33 Inhibition of LIMK1/LIMK2 in human SH-SY5Y cells assessed as effect on phospho c... 36205722
LIM domain kinase 2 IC50 = 549.54 nM 6.26 Inhibition of recombinant LIMK2(unknown origin) expressed in HEK293 cells using ... 36205722
LIM domain kinase 1 IC50 = 741.31 nM 6.13 Inhibition of recombinant LIMK1(unknown origin) expressed in HEK293 cells using ... 36205722
LIM domain kinase 2 IC50 = 1905.46 nM 5.72 Inhibition of recombinant LIMK2 (347 to 659 residues) (unknown origin) incubated... 36205722
LIM domain kinase 1 IC50 = 2041.74 nM 5.69 Inhibition of PAK mediated recombinant LIMK1 phosphorylation (330 to 637 residue... 36205722
Rho-associated protein kinase 1 IC50 = 5536.0 nM 5.26 Inhibition of human ROCK1 using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK peptide substra... 25621531
Rho-associated protein kinase 2 IC50 = 6565.0 nM 5.18 Inhibition of human ROCK2 using KEAKEKRQEQIAKRRRLSSLRASTSKSGGSQK peptide substra... 25621531

Literature References

PubMed DOI Target Context # Activities
36205722 10.1021/acs.jmedchem.2c00751 ADMET 6
25621531 10.1021/jm501680m Rattus norvegicus 6
25621531 10.1021/jm501680m LIM domain kinase 1 5
25621531 10.1021/jm501680m PC-3 4
36205722 10.1021/acs.jmedchem.2c00751 LIM domain kinase 2 3
36205722 10.1021/acs.jmedchem.2c00751 LIM domain kinase 1 3
25621531 10.1021/jm501680m Receptor-type tyrosine-protein kinase FLT3 2
25621531 10.1021/jm501680m Liver microsome 2
25621531 10.1021/jm501680m Serine/threonine-protein kinase 16 1
25621531 10.1021/jm501680m Aurora kinase A 1
25621531 10.1021/jm501680m Cytochrome P450 3A4 1
25621531 10.1021/jm501680m Proto-oncogene tyrosine-protein kinase receptor Ret 1
25621531 10.1021/jm501680m Cytochrome P450 2D6 1
25621531 10.1021/jm501680m Cytochrome P450 2C9 1
25621531 10.1021/jm501680m Cytochrome P450 1A2 1
36136092 10.1021/acs.jmedchem.2c01106 LIM domain kinase 1 1
36136092 10.1021/acs.jmedchem.2c01106 LIM domain kinase 2 1
25621531 10.1021/jm501680m Mitogen-activated protein kinase 10 1
25621531 10.1021/jm501680m Rho-associated protein kinase 1 1
29908439 10.1016/j.ejmech.2018.06.016 ADMET 1

Data from ChEMBL 36 via Core Engine