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Compound Detail

CHEMBL3298678

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O=C(N[C@H](CO)c1ccc(Cl)c(F)c1)N1CCc2cnc(NC3CCOCC3)nc2C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3298678
Phase Preclinical
Structure Type MOL
InChI Key OJRJASQFNLOAKZ-LJQANCHMSA-N
7
Targets
10
Activities
4
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

449.9
MW (Da)
2.66
ALogP
6
HBA
3
HBD
99.6
PSA (Ų)
0.65
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 C21H25ClFN5O3
MW 449.91
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness -1.48

Activity Summary

IC50 4 meas. best 8.7
Ki 3 meas. best 9.82
EC50 2 meas. best 6.41
Kd 1 meas. best 8.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase 1
CHEMBL4040
 Ki 9.82 9.52 0.1 2
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 8.7 8.15 2.0 2
CDK2/Cyclin A2
CHEMBL3038469
 Kd 8.39 8.39 4.1 1
Cyclin-dependent kinase 2
CHEMBL301
 IC50 8.0 8.0 10.0 1
Cyclin-dependent kinase 2/cyclin E1
CHEMBL1907605
 Ki 7.8 7.8 16.0 1
Mitogen-activated protein kinase; ERK1/ERK2
CHEMBL1907606
 IC50 7.7 7.7 20.0 1
A-375
CHEMBL613859
 EC50 6.41 6.41 390.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.13 6.13 740.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2164.07 ng.hr.mL-1 Mus musculus
AUC 13497.3 ng.hr.mL-1 Mus musculus
AUC 12012.6 ng.hr.mL-1 Mus musculus
AUC 89.98 ng.hr.mL-1 Rattus norvegicus
AUC 274.45 ng.hr.mL-1 Canis lupus familiaris
AUC 292.44 ng.hr.mL-1 Macaca fascicularis
CL 33.0 mL.min-1.kg-1 Mus musculus
CL 134.0 mL.min-1.kg-1 Mus musculus
CL 104.0 mL.min-1.kg-1 Rattus norvegicus
CL 32.0 mL.min-1.kg-1 Canis lupus familiaris
CL 33.0 mL.min-1.kg-1 Macaca fascicularis
Cmax 3120.0 nM Mus musculus
Cmax 9820.0 nM Mus musculus
Cmax 13900.0 nM Mus musculus
Cmax 90.0 nM Rattus norvegicus
Cmax 590.0 nM Canis lupus familiaris
Cmax 160.0 nM Macaca fascicularis
F 29.0 % Mus musculus
F 58.0 % Mus musculus
F 73.0 % Mus musculus
F 64.0 % Mus musculus
F 11.0 % Rattus norvegicus
F 26.0 % Canis lupus familiaris
F 19.0 % Macaca fascicularis
T1/2 2.4 hr Mus musculus
T1/2 7.5 hr Mus musculus
T1/2 2.7 hr Mus musculus
T1/2 1.7 hr Rattus norvegicus
T1/2 0.6 hr Canis lupus familiaris
T1/2 5.2 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase 1 Ki = 0.15 nM 9.82 Binding affinity to ERK2 (unknown origin) using Ulight-MBP as substrate assessed... 37736184
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 = 2.0 nM 8.7 Inhibition of human recombinant N-terminal 6-His-tagged ERK2 expressed in Escher... 24813737
CDK2/Cyclin A2 Kd = 4.1 nM 8.39 Binding affinity to His-tagged recombinant human full length CDK2/Cyclin A after... 25603482
Cyclin-dependent kinase 2 IC50 = 10.0 nM 8.0 Inhibition of Cdk2 (unknown origin) 24813737
Cyclin-dependent kinase 2/cyclin E1 Ki = 16.0 nM 7.8 Binding affinity to CDK2/Cyclin E1 (unknown origin) using Ulight-MBP as substrat... 37736184
Mitogen-activated protein kinase; ERK1/ERK2 IC50 = 20.0 nM 7.7 Inhibition of ERK1/2-mediated P90RSK phosphorylation at Ser380 in PMA-stimulated... 25603482
Mitogen-activated protein kinase 1 IC50 = 25.0 nM 7.6 Inhibition of ERK2 in human HepG2 cells assessed as P90RSK phosphorylation at Se... 24813737
A-375 EC50 = 390.0 nM 6.41 Antiproliferative activity against human A375 cells expressing B-Raf V600E mutan... 24813737
NON-PROTEIN TARGET EC50 = 740.0 nM 6.13 Antiproliferative activity against human HCT116 cells expressing K-Ras G12D muta... 24813737

Literature References

PubMed DOI Target Context # Activities
24813737 10.1016/j.bmcl.2014.04.068 Mus musculus 23
24813737 10.1016/j.bmcl.2014.04.068 Rattus norvegicus 6
24813737 10.1016/j.bmcl.2014.04.068 Canis familiaris 6
24813737 10.1016/j.bmcl.2014.04.068 Cynomolgus monkey 6
25603482 10.1021/jm501921k Molecular identity unknown 3
24813737 10.1016/j.bmcl.2014.04.068 NON-PROTEIN TARGET 3
24813737 10.1016/j.bmcl.2014.04.068 Mitogen-activated protein kinase 1 3
24813737 10.1016/j.bmcl.2014.04.068 Molecular identity unknown 2
24813737 10.1016/j.bmcl.2014.04.068 Unchecked 2
24813737 10.1016/j.bmcl.2014.04.068 Tyrosine-protein kinase ABL1 1
37736184 10.1021/acsmedchemlett.3c00142 Mitogen-activated protein kinase 1 1
24813737 10.1016/j.bmcl.2014.04.068 Tyrosine-protein kinase receptor UFO 1
24813737 10.1016/j.bmcl.2014.04.068 Aurora kinase B 1
24813737 10.1016/j.bmcl.2014.04.068 Aurora kinase A 1
24813737 10.1016/j.bmcl.2014.04.068 Tyrosine-protein kinase ABL2 1
24813737 10.1016/j.bmcl.2014.04.068 ALK tyrosine kinase receptor 1
24813737 10.1016/j.bmcl.2014.04.068 RAC-beta serine/threonine-protein kinase 1
24813737 10.1016/j.bmcl.2014.04.068 RAC-alpha serine/threonine-protein kinase 1
24813737 10.1016/j.bmcl.2014.04.068 Activin receptor type-1B 1
24813737 10.1016/j.bmcl.2014.04.068 A-375 1

Data from ChEMBL 36 via Core Engine