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Compound Detail

CHEMBL1822658

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Cc1cc(Nc2nc(Sc3ccc(NC(=O)CN4C[C@H](Oc5ccc(F)cc5)[C@@H](O)C4)cc3)nn3cccc23)n[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1822658
Phase Preclinical
Structure Type MOL
InChI Key MQWHYEKERKXFQY-ZEQRLZLVSA-N
3
Targets
8
Activities
2
Assay Types
5
PK Parameters
9
Publications
0
Known Names

Molecular Properties

574.6
MW (Da)
3.86
ALogP
10
HBA
4
HBD
132.7
PSA (Ų)
0.21
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H27FN8O3S
MW 574.64
Aromatic Rings 5
Heavy Atoms 41
NP-Likeness -1.69

Activity Summary

IC50 4 meas. best 8.3
Kd 4 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 8.3 8.3 5.0 2
Aurora kinase B
CHEMBL2185
 Kd 8.1 8.1 8.0 2
Aurora kinase A
CHEMBL4722
 Kd 7.82 7.82 15.0 2
Aurora kinase B
CHEMBL2185
 IC50 7.36 7.36 44.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 27283.91 ng.hr.mL-1 Mus musculus
AUC 672.33 ng.hr.mL-1 Rattus norvegicus
CL 25.2 mL.min-1.kg-1 Rattus norvegicus
T1/2 3.36 hr Rattus norvegicus
Vd 2.93 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 5.0 nM 8.3 Antiproliferative activity against human HCT116 cells 21802948
HCT-116 IC50 = 5.0 nM 8.3 Antiproliferative activity against human HCT116 cells after 72 hrs by BrdU-based... 22380736
Aurora kinase B Kd = 8.0 nM 8.1 Binding affinity to Aurora B kinase catalytic domain by competitive binding assa... 21802948
Aurora kinase B Kd = 8.0 nM 8.1 Binding affinity to Aurora kinase B catalytic domain by competition binding assa... 22380736
Aurora kinase A Kd = 15.0 nM 7.82 Binding affinity to Aurora A kinase catalytic domain by competitive binding assa... 21802948
Aurora kinase A Kd = 15.0 nM 7.82 Binding affinity to Aurora kinase A catalytic domain by competition binding assa... 22380736
Aurora kinase B IC50 = 44.0 nM 7.36 Inhibition of Aurora B kinase assessed as reduction in histone H3 phosphorylatio... 21802948
Aurora kinase B IC50 = 44.0 nM 7.36 Inhibition of Aurora kinase B-mediated histone H3 Ser10 phosphorylation in human... 22380736

Literature References

PubMed DOI Target Context # Activities
21802948 10.1016/j.bmcl.2011.07.027 Rattus norvegicus 4
21802948 10.1016/j.bmcl.2011.07.027 Mus musculus 2
21802948 10.1016/j.bmcl.2011.07.027 HCT-116 2
21802948 10.1016/j.bmcl.2011.07.027 Aurora kinase B 2
22380736 10.1021/jm201702g Aurora kinase B 2
21802948 10.1016/j.bmcl.2011.07.027 Aurora kinase C 1
21802948 10.1016/j.bmcl.2011.07.027 Aurora kinase A 1
22380736 10.1021/jm201702g HCT-116 1
22380736 10.1021/jm201702g Aurora kinase A 1

Data from ChEMBL 36 via Core Engine