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Compound Detail

CHEMBL4440965

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CNC(=O)C[C@@H]1C[C@@H](c2ccc(F)c(F)c2)[C@H](NC(=O)c2cc(-c3c(Cl)cnn3C)c(Cl)o2)CN1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4440965
Phase Preclinical
Structure Type MOL
InChI Key SXDPQGRNHSLZPC-ZJNRKIDTSA-N
13
Targets
14
Activities
1
Assay Types
17
PK Parameters
20
Publications
0
Known Names

Molecular Properties

526.4
MW (Da)
3.65
ALogP
6
HBA
3
HBD
101.2
PSA (Ų)
0.46
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H23Cl2F2N5O3
MW 526.37
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -1.10

Activity Summary

IC50 14 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
RAC-beta serine/threonine-protein kinase
CHEMBL2431
 IC50 9.7 9.31 0.2 2
Unchecked
CHEMBL612545
 IC50 9.52 9.52 0.3 1
RAC-alpha serine/threonine-protein kinase
CHEMBL4282
 IC50 8.86 8.86 1.4 1
RAC-gamma serine/threonine-protein kinase
CHEMBL4816
 IC50 8.77 8.77 1.7 1
Ribosomal protein S6 kinase beta-1
CHEMBL4501
 IC50 8.05 8.05 8.9 1
Serine/threonine-protein kinase AKT
CHEMBL2111353
 IC50 7.36 7.36 44.0 1
LNCaP
CHEMBL612518
 IC50 7.3 7.3 50.0 1
Rho-associated protein kinase 1
CHEMBL3231
 IC50 7.19 7.19 64.0 1
Protein kinase C (PKC)
CHEMBL2093867
 IC50 7.03 7.03 94.0 1
Ribosomal protein S6 kinase alpha-1
CHEMBL2553
 IC50 6.88 6.88 131.0 1
Serine/threonine-protein kinase Sgk1
CHEMBL2343
 IC50 6.84 6.84 145.0 1
OVCAR-8
CHEMBL612555
 IC50 6.1 6.1 800.0 1
HCT-116
CHEMBL394
 IC50 5.96 5.96 1100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3092.2 ng.hr.mL-1 Rattus norvegicus
AUC 2442.2 ng.hr.mL-1 Rattus norvegicus
AUC 21221.5 ng.hr.mL-1 Mus musculus
AUC 21091.9 ng.hr.mL-1 Mus musculus
CL 236.67 mL.min-1.kg-1 Rattus norvegicus
CL 31.67 mL.min-1.kg-1 Mus musculus
Cmax 773.98 nM Rattus norvegicus
Cmax 6877.29 nM Mus musculus
F 48.4 % Mus musculus
MRT 11.4 hr Rattus norvegicus
MRT 5.3 hr Mus musculus
T1/2 6.4 hr Rattus norvegicus
T1/2 3.3 hr Mus musculus
Tmax 1.8 hr Rattus norvegicus
Tmax 1.0 hr Mus musculus
Vd 147.2 L.kg-1 Rattus norvegicus
Vd 9.0 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
RAC-beta serine/threonine-protein kinase IC50 = 0.2 nM 9.7 Inhibition of N-terminal GST-tagged human AKT2 (120 to 481 residues) expressed i... 34375113
Unchecked IC50 = 0.3 nM 9.52 Inhibition of recombinant His-tagged human PKA expressed in Escherichia coli usi... 31298542
RAC-beta serine/threonine-protein kinase IC50 = 1.2 nM 8.92 Inhibition of human Akt2 by mobile shift assay 31298542
RAC-alpha serine/threonine-protein kinase IC50 = 1.37 nM 8.86 Inhibition of human Akt1 expressed in Escherichia coli using STK Substrate 2-bio... 31298542
RAC-gamma serine/threonine-protein kinase IC50 = 1.7 nM 8.77 Inhibition of Akt3 (unknown origin) by mobile shift assay 31298542
Ribosomal protein S6 kinase beta-1 IC50 = 8.9 nM 8.05 Inhibition of human P70S6K by mobility shift assay 31298542
Serine/threonine-protein kinase AKT IC50 = 44.0 nM 7.36 Inhibition of Akt in human LNCaP cells assessed as reduction in PRAS40 phosphory... 31298542
LNCaP IC50 = 50.0 nM 7.3 Antiproliferative activity against human LNCAP cells 31298542
Rho-associated protein kinase 1 IC50 = 64.0 nM 7.19 Inhibition of human ROCK1 by mobile shift assay 31298542
Protein kinase C (PKC) IC50 = 94.0 nM 7.03 Inhibition of PKC (unknown origin) 31298542
Ribosomal protein S6 kinase alpha-1 IC50 = 131.0 nM 6.88 Inhibition of RSK1 (unknown origin) by mobility shift assay 31298542
Serine/threonine-protein kinase Sgk1 IC50 = 145.0 nM 6.84 Inhibition of human SGK by mobility shift assay 31298542
OVCAR-8 IC50 = 800.0 nM 6.1 Antiproliferative activity against human OVCAR8 cells 31298542
HCT-116 IC50 = 1100.0 nM 5.96 Antiproliferative activity against human HCT116 cells after 72 hrs by SRB assay 31298542

Literature References

PubMed DOI Target Context # Activities
31298542 10.1021/acs.jmedchem.9b00891 ADMET 37
31298542 10.1021/acs.jmedchem.9b00891 SK-OV-3 7
31298542 10.1021/acs.jmedchem.9b00891 Serine/threonine-protein kinase AKT 6
31298542 10.1021/acs.jmedchem.9b00891 Mus musculus 4
31298542 10.1021/acs.jmedchem.9b00891 Unchecked 3
31298542 10.1021/acs.jmedchem.9b00891 OVCAR-8 2
31298542 10.1021/acs.jmedchem.9b00891 HUVEC 2
31298542 10.1021/acs.jmedchem.9b00891 Serine/threonine-protein kinase Sgk1 1
31298542 10.1021/acs.jmedchem.9b00891 Serine/threonine-protein kinase haspin 1
31298542 10.1021/acs.jmedchem.9b00891 Casein kinase I isoform epsilon 1
31298542 10.1021/acs.jmedchem.9b00891 ATP-sensitive inward rectifier potassium channel 1 1
31298542 10.1021/acs.jmedchem.9b00891 Inward rectifier potassium channel 2 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium voltage-gated channel subfamily A member 10 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium voltage-gated channel subfamily A member 3 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium voltage-gated channel subfamily A member 4 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium voltage-gated channel subfamily A member 5 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium voltage-gated channel subfamily A member 6 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium voltage-gated channel subfamily A member 7 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 1
31298542 10.1021/acs.jmedchem.9b00891 Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 3 1

Data from ChEMBL 36 via Core Engine