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Compound Detail

CHEMBL457614

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CC(C)Oc1cc(Nc2nc(N[C@@H](C)c3ccc(F)cn3)ncc2Cl)n[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL457614
Phase Preclinical
Structure Type MOL
InChI Key LBVKEEFIPBQIMD-JTQLQIEISA-N
12
Targets
29
Activities
4
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

391.8
MW (Da)
4.09
ALogP
7
HBA
3
HBD
100.6
PSA (Ų)
0.56
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C17H19ClFN7O
MW 391.84
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.49

Activity Summary

IC50 24 meas. best 9.59
Kd 2 meas. best 9.69
Ki 2 meas. best 9.44
EC50 1 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
High affinity nerve growth factor receptor
CHEMBL2815
 Kd 9.69 9.69 0.2 1
High affinity nerve growth factor receptor
CHEMBL2815
 IC50 9.59 8.72 0.3 9
High affinity nerve growth factor receptor
CHEMBL2815
 Ki 9.44 8.935 0.4 2
BDNF/NT-3 growth factors receptor
CHEMBL4898
 IC50 9.03 8.6 0.9 2
High affinity nerve growth factor receptor
CHEMBL2815
 EC50 9.0 9.0 1.0 1
MCF-10A
CHEMBL614321
 IC50 8.82 7.215 1.5 2
Unchecked
CHEMBL612545
 IC50 8.7 8.7 2.0 1
Tyrosine-protein kinase Yes
CHEMBL2073
 IC50 8.52 7.965 3.0 2
NT-3 growth factor receptor
CHEMBL5608
 IC50 8.14 8.14 7.2 1
BaF3
CHEMBL614524
 IC50 7.7 7.2733 20.0 3
KM12
CHEMBL614709
 IC50 7.68 7.68 21.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.75 5.75 1800.0 1
Aurora kinase A
CHEMBL4722
 Kd 5.72 5.72 1908.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.28 5.28 5200.0 1
RD
CHEMBL614144
 IC50 5.28 5.28 5300.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 17.0 mL.min-1.kg-1 Rattus norvegicus
CL 9.0 mL.min-1.kg-1 Canis lupus familiaris
F 31.0 % Rattus norvegicus
F 60.0 % Canis lupus familiaris
Fu 0.069 - Homo sapiens
Ka 2.51 10'5/M/s Homo sapiens
T1/2 1.4 hr Rattus norvegicus
T1/2 7.5 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
High affinity nerve growth factor receptor Kd = 0.204 nM 9.69 Binding affinity to wild type human biotinylated and N-terminal DYKDDDDK-tagged ... 31610943
High affinity nerve growth factor receptor IC50 = 0.26 nM 9.59 Inhibition of GAL4 fused TrkA (unknown origin) expressed in PC12 cells transfect... 27318978
High affinity nerve growth factor receptor IC50 = 0.26 nM 9.59 Inhibition of GAL4 fused TrkA (unknown origin) expressed in PC12 cells transfect... 27318978
High affinity nerve growth factor receptor IC50 = 0.3 nM 9.52 Inhibition of recombinant human His-tagged TrkA kinase domain (441-796 residues)... 31444087
High affinity nerve growth factor receptor Ki = 0.36 nM 9.44 Inhibition of human active TRKA assessed as decrease in substrate phosphorylatio... 31610943
BDNF/NT-3 growth factors receptor IC50 = 0.93 nM 9.03 Inhibition of wild type human N-terminal GST-fusion tagged TRKB kinase domain (4... 31699609
High affinity nerve growth factor receptor EC50 = 1.0 nM 9.0 Inhibition of TrkA phosphorylation in human MVF10A cells overexpressing TrkA del... 18646745
MCF-10A IC50 = 1.51 nM 8.82 Cytotoxicity against human MCF10A cells overexpressing constitutively active TRK... 24900538
Unchecked IC50 = 2.0 nM 8.7 Inhibition of human TRKA extracellular domain (75 amino acid residues) deletion ... 31077998
High affinity nerve growth factor receptor IC50 = 2.56 nM 8.59 Inhibition of wild type human His-tagged TRKA kinase domain (441 to 796 residues... 31699609
High affinity nerve growth factor receptor IC50 = 2.81 nM 8.55 Inhibition of TRKA E735A mutant (unknown origin) expressed in baculovirus infect... 31699609
Tyrosine-protein kinase Yes IC50 = 3.0 nM 8.52 Inhibition of Yes1 (unknown origin) by [gamma-33P]-ATP radiolabeled enzyme activ... 23787099
High affinity nerve growth factor receptor IC50 = 3.2 nM 8.49 Inhibition of juxtamembrane region containing recombinant human N-terminal His6-... 28159414
High affinity nerve growth factor receptor Ki = 3.7 nM 8.43 Inhibition of human inactive TRKA assessed as decrease in substrate phosphorylat... 31610943
BDNF/NT-3 growth factors receptor IC50 = 6.8 nM 8.17 Inhibition of recombinant human TrkB expressed in DHFR deficient CHO cells asses... 28159414
NT-3 growth factor receptor IC50 = 7.2 nM 8.14 Inhibition of recombinant human TrkC expressed in DHFR deficient CHO cells asses... 28159414
High affinity nerve growth factor receptor IC50 = 8.0 nM 8.1 Inhibition of human TRKA expressed in human MCF10A cells by ELISA 31077998
High affinity nerve growth factor receptor IC50 = 8.9 nM 8.05 Inhibition of juxtamembrane region deficient recombinant human N-terminal His6-t... 28159414
High affinity nerve growth factor receptor IC50 = 9.9 nM 8.0 Inhibition of recombinant human TrkA expressed in DHFR deficient CHO cells asses... 28159414
BaF3 IC50 = 20.0 nM 7.7 Antiproliferative activity against mouse BaF3 cells harboring TRKA F589L mutant ... 35617855

Literature References

PubMed DOI Target Context # Activities
31610943 10.1016/j.bmcl.2019.126680 High affinity nerve growth factor receptor 7
28159414 10.1016/j.bmcl.2017.01.056 High affinity nerve growth factor receptor 4
18646745 10.1021/jm800343j Rattus norvegicus 3
35617855 10.1016/j.ejmech.2022.114451 BaF3 3
31699609 10.1016/j.bmcl.2019.126775 High affinity nerve growth factor receptor 3
- 10.6019/CHEMBL3885741 Aurora kinase A 3
24900538 10.1021/ml300074j MCF-10A 3
18646745 10.1021/jm800343j Canis familiaris 3
23787099 10.1016/j.bmcl.2013.05.072 Tyrosine-protein kinase Yes 2
27318978 10.1016/j.ejmech.2016.06.003 High affinity nerve growth factor receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
23787099 10.1016/j.bmcl.2013.05.072 NON-PROTEIN TARGET 1
23787099 10.1016/j.bmcl.2013.05.072 RD 1
- 10.6019/EOS300108 HepG2 1
28159414 10.1016/j.bmcl.2017.01.056 BDNF/NT-3 growth factors receptor 1
28159414 10.1016/j.bmcl.2017.01.056 NT-3 growth factor receptor 1
18646745 10.1021/jm800343j No relevant target 1
18646745 10.1021/jm800343j High affinity nerve growth factor receptor 1
18646745 10.1021/jm800343j Plasma 1
31699609 10.1016/j.bmcl.2019.126775 Unchecked 1

Data from ChEMBL 36 via Core Engine