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Compound Detail

CHEMBL3329684

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COc1ccc(C(=O)NC(=O)Nc2ccc3c(c2)NC(=O)/C3=C\c2[nH]c(C)c(C(=O)NCCN3CCCC3)c2C)c(F)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3329684
Phase Preclinical
Structure Type MOL
InChI Key NKKNQMFHKZEGQU-KQWNVCNZSA-N
10
Targets
11
Activities
1
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

588.6
MW (Da)
4.06
ALogP
6
HBA
5
HBD
144.7
PSA (Ų)
0.25
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C31H33FN6O5
MW 588.64
Aromatic Rings 3
Heavy Atoms 43
NP-Likeness -1.39

Activity Summary

IC50 11 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aurora kinase B
CHEMBL2185
 IC50 9.4 9.4 0.4 1
Aurora kinase A
CHEMBL4722
 IC50 9.4 9.4 0.4 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 9.3 9.3 0.5 2
MOLM-13
CHEMBL3706572
 IC50 9.15 9.15 0.7 1
Tyrosine-protein kinase Lck
CHEMBL258
 IC50 8.64 8.64 2.3 1
MV4-11
CHEMBL613835
 IC50 8.62 8.62 2.4 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.55 8.55 2.8 1
Mast/stem cell growth factor receptor Kit
CHEMBL1936
 IC50 7.85 7.85 14.0 1
THP-1
CHEMBL614245
 IC50 7.31 7.31 48.9 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.01 5.01 9670.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1965.0 ng.hr.mL-1 Mus musculus
AUC 252.1 ng.hr.mL-1 Mus musculus
CL 8.333 mL.min-1.kg-1 Mus musculus
Cmax 1110.19 nM Mus musculus
Cmax 35.51 nM Mus musculus
F 2.6 % Mus musculus
T1/2 27.6 hr Mus musculus
T1/2 8.6 hr Mus musculus
Tmax 0.1 hr Mus musculus
Tmax 1.7 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aurora kinase B IC50 = 0.4 nM 9.4 Inhibition of Aurora B (unknown origin) using HLRRASLG substrate 25089810
Aurora kinase A IC50 = 0.4 nM 9.4 Inhibition of Aurora-A (unknown origin) by kinase-glo luminescent assay 32659083
Receptor-type tyrosine-protein kinase FLT3 IC50 = 0.5 nM 9.3 Inhibition of FLT3 (unknown origin) using EAIYAAPFAKKK substrate 25089810
Receptor-type tyrosine-protein kinase FLT3 IC50 = 0.5 nM 9.3 Inhibition of FLT3-ITD mutant (unknown origin) 32659083
MOLM-13 IC50 = 0.7 nM 9.15 Cytotoxicity against human MOLM13 cells assessed as cell viability after 48 hrs ... 25089810
Tyrosine-protein kinase Lck IC50 = 2.3 nM 8.64 Inhibition of Lck (unknown origin) 25089810
MV4-11 IC50 = 2.4 nM 8.62 Cytotoxicity against human MV4-11 cells assessed as cell viability after 48 hrs ... 25089810
NON-PROTEIN TARGET IC50 = 2.8 nM 8.55 Cytotoxicity against human HL60 cells assessed as cell viability after 48 hrs by... 25089810
Mast/stem cell growth factor receptor Kit IC50 = 14.0 nM 7.85 Inhibition of c-Kit (unknown origin) 25089810
THP-1 IC50 = 48.9 nM 7.31 Cytotoxicity against human THP1 cells assessed as cell viability after 48 hrs by... 25089810
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 9670.0 nM 5.01 Inhibition of human ERG channel after 3 hrs by fluorescence assay 25089810

Literature References

PubMed DOI Target Context # Activities
25089810 10.1016/j.ejmech.2014.07.108 Mus musculus 13
25089810 10.1016/j.ejmech.2014.07.108 MOLM-13 7
25089810 10.1016/j.ejmech.2014.07.108 Receptor-type tyrosine-protein kinase FLT3 3
25089810 10.1016/j.ejmech.2014.07.108 THP-1 3
25089810 10.1016/j.ejmech.2014.07.108 Tyrosine-protein kinase Lck 2
25089810 10.1016/j.ejmech.2014.07.108 Mast/stem cell growth factor receptor Kit 2
25089810 10.1016/j.ejmech.2014.07.108 ADMET 2
25089810 10.1016/j.ejmech.2014.07.108 Tyrosine-protein kinase ABL1 1
25089810 10.1016/j.ejmech.2014.07.108 RAC-alpha serine/threonine-protein kinase 1
25089810 10.1016/j.ejmech.2014.07.108 Aurora kinase A 1
25089810 10.1016/j.ejmech.2014.07.108 Aurora kinase C 1
25089810 10.1016/j.ejmech.2014.07.108 Serine/threonine-protein kinase B-raf 1
25089810 10.1016/j.ejmech.2014.07.108 NON-PROTEIN TARGET 1
25089810 10.1016/j.ejmech.2014.07.108 Hepatocyte growth factor receptor 1
25089810 10.1016/j.ejmech.2014.07.108 Proto-oncogene tyrosine-protein kinase Src 1
25089810 10.1016/j.ejmech.2014.07.108 Serine/threonine-protein kinase Chk1 1
32659083 10.1021/acs.jmedchem.0c00696 Aurora kinase A 1
25089810 10.1016/j.ejmech.2014.07.108 Receptor tyrosine-protein kinase erbB-2 1
25089810 10.1016/j.ejmech.2014.07.108 Fibroblast growth factor receptor 1 1
25089810 10.1016/j.ejmech.2014.07.108 MV4-11 1

Data from ChEMBL 36 via Core Engine