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Compound Detail

CHEMBL4093614

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Cc1[nH]c(/C=C2\C(=O)Nc3ccc(F)cc32)c(C)c1NC(=O)[C@H]1CCCN1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4093614
Phase Preclinical
Structure Type MOL
InChI Key NBVFGQHCNIZKKI-SKFKWQMISA-N
Parent Compound CHEMBL4116634
Active Moiety CHEMBL4116634
17
Targets
18
Activities
1
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

368.4
MW (Da)
2.95
ALogP
3
HBA
4
HBD
86.0
PSA (Ų)
0.63
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H22ClFN4O2
MW 404.87
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -0.70

Activity Summary

IC50 18 meas. best 9.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 9.15 9.15 0.7 1
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 8.57 8.425 2.7 2
MOLM-13
CHEMBL3706572
 IC50 7.63 7.63 23.6 1
MV4-11
CHEMBL613835
 IC50 7.61 7.61 24.8 1
Platelet-derived growth factor receptor alpha
CHEMBL2007
 IC50 6.76 6.76 174.6 1
Mast/stem cell growth factor receptor Kit
CHEMBL1936
 IC50 6.64 6.64 227.0 1
Kasumi 1
CHEMBL613988
 IC50 6.6 6.6 250.5 1
LC-2-ad
CHEMBL2366260
 IC50 6.21 6.21 621.4 1
NCI-H2228
CHEMBL1075536
 IC50 5.46 5.46 3438.2 1
Jurkat
CHEMBL397
 IC50 5.38 5.38 4179.6 1
HL-60
CHEMBL383
 IC50 5.19 5.19 6469.9 1
COLO 205
CHEMBL614561
 IC50 5.18 5.18 6603.9 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.17 5.17 6730.0 1
HUVEC
CHEMBL613979
 IC50 4.95 4.95 11322.3 1
786-0
CHEMBL613102
 IC50 4.91 4.91 12237.8 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.75 4.75 17730.0 1
KG-1
CHEMBL612264
 IC50 4.61 4.61 24483.8 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3071.0 ng.hr.mL-1 Mus musculus
Cmax 1924.49 nM Mus musculus
F 59.0 % Mus musculus
T1/2 1.6 hr Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.7 nM 9.15 Inhibition of human FLT3 ITD mutant 28038328
Receptor-type tyrosine-protein kinase FLT3 IC50 = 2.7 nM 8.57 Inhibition of human FLT3 D835Y mutant 28038328
Receptor-type tyrosine-protein kinase FLT3 IC50 = 5.3 nM 8.28 Inhibition of human FLT3 28038328
MOLM-13 IC50 = 23.6 nM 7.63 Antiproliferative activity against human MOLM13 cells harboring FLT3 ITD mutant ... 28038328
MV4-11 IC50 = 24.8 nM 7.61 Antiproliferative activity against human MV4-11 cells harboring FLT3 ITD mutant ... 28038328
Platelet-derived growth factor receptor alpha IC50 = 174.6 nM 6.76 Inhibition of human PDGFRalpha 28038328
Mast/stem cell growth factor receptor Kit IC50 = 227.0 nM 6.64 Inhibition of human KIT 28038328
Kasumi 1 IC50 = 250.5 nM 6.6 Antiproliferative activity against human Kasumi-1 cells harboring RET after 72 h... 28038328
LC-2-ad IC50 = 621.4 nM 6.21 Antiproliferative activity against human LC2/ad cells harboring RET after 72 hrs... 28038328
NCI-H2228 IC50 = 3438.2 nM 5.46 Antiproliferative activity against human NCI-H2228 cells harboring ALK after 72 ... 28038328
Jurkat IC50 = 4179.6 nM 5.38 Antiproliferative activity against FLT3 negative human Jurkat cells after 72 hrs... 28038328
HL-60 IC50 = 6469.9 nM 5.19 Antiproliferative activity against FLT3 negative human HL60 cells after 72 hrs b... 28038328
COLO 205 IC50 = 6603.9 nM 5.18 Antiproliferative activity against human COLO205 cells harboring B-Raf after 72 ... 28038328
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6730.0 nM 5.17 Inhibition of human ERG expressed in CHO cells by Qpatch assay 28038328
HUVEC IC50 = 11322.3 nM 4.95 Antiproliferative activity against HUVEC after 72 hrs by MTS assay 28038328
786-0 IC50 = 12237.8 nM 4.91 Antiproliferative activity against human 786-O cells harboring VHL after 72 hrs ... 28038328
Cytochrome P450 1A2 IC50 = 17730.0 nM 4.75 Inhibition of microsomal CYP1A2 (unknown origin) using phenacetin as substrate p... 28038328
KG-1 IC50 = 24483.8 nM 4.61 Antiproliferative activity against human KG1 cells harboring wild type FLT3 afte... 28038328

Literature References

PubMed DOI Target Context # Activities
28038328 10.1016/j.ejmech.2016.12.038 Mus musculus 7
28038328 10.1016/j.ejmech.2016.12.038 MV4-11 6
28038328 10.1016/j.ejmech.2016.12.038 Receptor-type tyrosine-protein kinase FLT3 5
28038328 10.1016/j.ejmech.2016.12.038 Platelet-derived growth factor receptor alpha 5
28038328 10.1016/j.ejmech.2016.12.038 Unchecked 3
28038328 10.1016/j.ejmech.2016.12.038 Mast/stem cell growth factor receptor Kit 3
28038328 10.1016/j.ejmech.2016.12.038 Cytochrome P450 3A4 2
28038328 10.1016/j.ejmech.2016.12.038 Proto-oncogene tyrosine-protein kinase receptor Ret 1
28038328 10.1016/j.ejmech.2016.12.038 ALK tyrosine kinase receptor 1
28038328 10.1016/j.ejmech.2016.12.038 Tyrosine-protein kinase ABL1 1
28038328 10.1016/j.ejmech.2016.12.038 Voltage-gated inwardly rectifying potassium channel KCNH2 1
28038328 10.1016/j.ejmech.2016.12.038 Serine/threonine-protein kinase PLK1 1
28038328 10.1016/j.ejmech.2016.12.038 RAF proto-oncogene serine/threonine-protein kinase 1
28038328 10.1016/j.ejmech.2016.12.038 Serine/threonine-protein kinase B-raf 1
28038328 10.1016/j.ejmech.2016.12.038 Vascular endothelial growth factor receptor 2 1
28038328 10.1016/j.ejmech.2016.12.038 Hepatocyte growth factor receptor 1
28038328 10.1016/j.ejmech.2016.12.038 Fibroblast growth factor receptor 1 1
28038328 10.1016/j.ejmech.2016.12.038 Epidermal growth factor receptor 1
28038328 10.1016/j.ejmech.2016.12.038 Platelet-derived growth factor receptor beta 1
28038328 10.1016/j.ejmech.2016.12.038 Vascular endothelial growth factor receptor 1 1

Data from ChEMBL 36 via Core Engine