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Compound Detail

CHEMBL3409588

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O=c1cc(-c2ccnc(NC3CCOCC3)n2)ccn1[C@H](CO)c1ccc(Cl)c(F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3409588
Phase Preclinical
Structure Type MOL
InChI Key PGGLRAWFUJMQBN-HXUWFJFHSA-N
6
Targets
9
Activities
3
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

444.9
MW (Da)
3.27
ALogP
7
HBA
2
HBD
89.3
PSA (Ų)
0.61
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22ClFN4O3
MW 444.89
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.27

Activity Summary

IC50 7 meas. best 8.96
Kd 1 meas. best 7.68
Ki 1 meas. best 9.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase 1
CHEMBL4040
 Ki 9.22 9.22 0.6 1
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 8.96 8.5933 1.1 3
Mitogen-activated protein kinase 3
CHEMBL3385
 IC50 8.57 8.57 2.7 1
Mitogen-activated protein kinase; ERK1/ERK2
CHEMBL1907606
 IC50 7.77 7.77 17.0 1
CDK2/Cyclin A2
CHEMBL3038469
 Kd 7.68 7.68 21.0 1
Unchecked
CHEMBL612545
 IC50 7.31 7.31 49.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.84 4.84 14500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1468.14 ng.hr.mL-1 Macaca fascicularis
AUC 2166.61 ng.hr.mL-1 Canis lupus familiaris
AUC 956.51 ng.hr.mL-1 Rattus norvegicus
AUC 77855.75 ng.hr.mL-1 Mus musculus
AUC 57390.81 ng.hr.mL-1 Mus musculus
AUC 20820.85 ng.hr.mL-1 Mus musculus
AUC 2402.41 ng.hr.mL-1 Mus musculus
AUC 1356.91 ng.hr.mL-1 Mus musculus
CL 12.0 mL.min-1.kg-1 Macaca fascicularis
CL 18.0 mL.min-1.kg-1 Canis lupus familiaris
CL 39.0 mL.min-1.kg-1 Rattus norvegicus
CL 40.0 mL.min-1.kg-1 Mus musculus
CL 33.0 mL.min-1.kg-1 Mus musculus
Cmax 980.0 nM Macaca fascicularis
Cmax 2910.0 nM Canis lupus familiaris
Cmax 1490.0 nM Rattus norvegicus
Cmax 67700.0 nM Mus musculus
Cmax 38900.0 nM Mus musculus
Cmax 20200.0 nM Mus musculus
Cmax 3120.0 nM Mus musculus
F 22.0 % Macaca fascicularis
F 46.0 % Canis lupus familiaris
F 44.0 % Rattus norvegicus
F 127.0 % Mus musculus
F 139.0 % Mus musculus
F 169.0 % Mus musculus
F 139.0 % Mus musculus
F 66.0 % Mus musculus
F 66.0 % Mus musculus
Fu 0.058 - Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase 1 Ki = 0.6 nM 9.22 Inhibition of 6-His tagged human ERK2 expressed in Escherichia coli measured ove... 25603482
Mitogen-activated protein kinase 1 IC50 = 1.1 nM 8.96 Inhibition of ERK2 (unknown origin) 27227380
Mitogen-activated protein kinase 3 IC50 = 2.7 nM 8.57 Inhibition of ERK1 (unknown origin) 27227380
Mitogen-activated protein kinase 1 IC50 = 3.9 nM 8.41 Enzymatic Assay: Compounds were tested in an enzymatic assay using human ERK-2 (... -
Mitogen-activated protein kinase 1 IC50 = 3.9 nM 8.41 ERK-2 Enzymatic Assay: Compounds were tested in an enzymatic assay using human E... -
Mitogen-activated protein kinase; ERK1/ERK2 IC50 = 17.0 nM 7.77 Inhibition of ERK1/2-mediated P90RSK phosphorylation at Ser380 in PMA-stimulated... 25603482
CDK2/Cyclin A2 Kd = 21.0 nM 7.68 Binding affinity to His-tagged recombinant human full length CDK2/Cyclin A after... 25603482
Unchecked IC50 = 49.0 nM 7.31 Inhibition of ERK in PMA-stimulated human HepG2 cells assessed as inhibition of ... 27227380
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 14500.0 nM 4.84 Inhibition of human ERG 25603482

Literature References

PubMed DOI Target Context # Activities
25603482 10.1021/jm501921k Mus musculus 21
27227380 10.1021/acs.jmedchem.6b00389 ADMET 9
25603482 10.1021/jm501921k Rattus norvegicus 5
25603482 10.1021/jm501921k Canis familiaris 5
25603482 10.1021/jm501921k Cynomolgus monkey 5
25603482 10.1021/jm501921k Molecular identity unknown 3
25603482 10.1021/jm501921k Cytochrome P450 2C9 2
27227380 10.1021/acs.jmedchem.6b00389 Unchecked 2
25603482 10.1021/jm501921k MDCK 2
25603482 10.1021/jm501921k Cytochrome P450 1A2 2
25603482 10.1021/jm501921k Cytochrome P450 2C19 2
25603482 10.1021/jm501921k Cytochrome P450 2D6 2
25603482 10.1021/jm501921k Cytochrome P450 3A4 2
27227380 10.1021/acs.jmedchem.6b00389 Mus musculus 2
25603482 10.1021/jm501921k HCT-116 2
25603482 10.1021/jm501921k Mitogen-activated protein kinase 1 2
25603482 10.1021/jm501921k Adenosine receptor A1 1
25603482 10.1021/jm501921k No relevant target 1
25603482 10.1021/jm501921k NON-PROTEIN TARGET 1
25603482 10.1021/jm501921k Unchecked 1

Data from ChEMBL 36 via Core Engine