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Compound Detail

CHEMBL2397317

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COc1ccc(-c2c(C)nn3c(NCCN4CCOCC4)cc(C)nc23)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2397317
Phase Preclinical
Structure Type MOL
InChI Key RITGMCAEZVMEQO-UHFFFAOYSA-N
11
Targets
21
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

411.5
MW (Da)
2.77
ALogP
8
HBA
1
HBD
73.2
PSA (Ų)
0.64
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H29N5O3
MW 411.51
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.65

Activity Summary

EC50 14 meas. best 6.7
IC50 7 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Phosphatidylinositol 4-kinase beta
CHEMBL3268
 IC50 8.1 6.97 8.0 4
Unchecked
CHEMBL612545
 IC50 7.22 6.0567 60.0 3
Human rhinovirus sp.
CHEMBL612470
 EC50 6.7 6.15 200.0 2
rhinovirus A16
CHEMBL613769
 EC50 6.6 6.175 250.0 2
rhinovirus B14
CHEMBL613759
 EC50 6.23 5.935 590.0 2
Coxsackievirus B4
CHEMBL612320
 EC50 6.14 6.14 720.0 1
Enterovirus A71
CHEMBL612436
 EC50 6.14 5.75 730.0 2
Echovirus
CHEMBL612353
 EC50 6.07 6.07 860.0 1
Hepatitis C virus
CHEMBL379
 EC50 5.99 5.99 1030.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.92 5.92 1200.0 1
Coxsackievirus B3
CHEMBL613554
 EC50 5.47 5.39 3380.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 126333.57 ng.hr.mL-1 Mus musculus
AUC 18517.95 ng.hr.mL-1 Mus musculus
AUC 1481.44 ng.hr.mL-1 Mus musculus
AUC 4115.1 ng.hr.mL-1 Rattus norvegicus
CL - - Mus musculus
CL 18.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 52000.0 nM Mus musculus
Cmax 15000.0 nM Mus musculus
Cmax 1900.0 nM Mus musculus
Cmax 2000.0 nM Rattus norvegicus
F 91.0 % Rattus norvegicus
T1/2 2.8 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Phosphatidylinositol 4-kinase beta IC50 = 8.0 nM 8.1 Inhibition of recombinant human full length GST-tagged PI4K3beta expressed in ba... 29952567
Unchecked IC50 = 60.0 nM 7.22 Inhibition of PI4K3beta (unknown origin) by select screen kinase profiling assay 28122178
Phosphatidylinositol 4-kinase beta IC50 = 60.0 nM 7.22 Inhibition of PI4K3beta (unknown origin) 24900715
Phosphatidylinositol 4-kinase beta IC50 = 137.0 nM 6.86 Inhibition of PI4K3beta (unknown origin) 23726345
Unchecked IC50 = 150.0 nM 6.82 Inhibition of PI4K3beta (unknown origin) assessed as hydrolysis of ATP for 60 mi... 25897704
Human rhinovirus sp. EC50 = 200.0 nM 6.7 Antiviral activity against Human rhinovirus C15 assessed as inhibition of viral ... 23726345
rhinovirus A16 EC50 = 250.0 nM 6.6 Antiviral activity against Human rhinovirus A16 assessed as inhibition of viral ... 23726345
rhinovirus B14 EC50 = 590.0 nM 6.23 Antiviral activity against Human rhinovirus B14 assessed as inhibition of viral ... 23726345
Enterovirus A71 EC50 = 730.0 nM 6.14 Antiviral activity against Enterovirus 71 infected in RD cells assessed as reduc... 28122178
Coxsackievirus B4 EC50 = 720.0 nM 6.14 Antiviral activity against Human coxsackievirus B4 assessed as protection agains... 23726345
Echovirus EC50 = 860.0 nM 6.07 Antiviral activity against Echovirus assessed as protection against virus-induce... 23726345
Hepatitis C virus EC50 = 1030.0 nM 5.99 Antiviral activity in HCV 1b infected in HUH 7-lunet cells after 3 days by Dual-... 25897704
NON-PROTEIN TARGET EC50 = 1200.0 nM 5.92 Antiviral activity against Poliovirus assessed as protection against virus-induc... 23726345
rhinovirus A16 EC50 = 1800.0 nM 5.75 Antiviral activity against Human rhinovirus 16 assessed as protection against vi... 23726345
Phosphatidylinositol 4-kinase beta IC50 = 2000.0 nM 5.7 Inhibition of PI4K3beta in human PBMC assessed as reduction in mitomycin-C treat... 29952567
rhinovirus B14 EC50 = 2300.0 nM 5.64 Antiviral activity against Human rhinovirus 14 assessed as protection against vi... 23726345
Human rhinovirus sp. EC50 = 2500.0 nM 5.6 Antirhinovirus activity in HRVM infected in H1-HeLa cells assessed as inhibition... 25897704
Coxsackievirus B3 EC50 = 3380.0 nM 5.47 Anticoxsackie activity in CVB3 strain Nancy infected in human HeLa cells assesse... 25897704
Enterovirus A71 EC50 = 4400.0 nM 5.36 Antiviral activity against Human enterovirus 71 assessed as protection against v... 23726345
Coxsackievirus B3 EC50 = 4900.0 nM 5.31 Antiviral activity against Human coxsackievirus B3 assessed as protection agains... 23726345

Literature References

PubMed DOI Target Context # Activities
23726345 10.1016/j.bmcl.2013.04.077 Mus musculus 7
23726345 10.1016/j.bmcl.2013.04.077 Rattus norvegicus 5
23726345 10.1016/j.bmcl.2013.04.077 No relevant target 3
25897704 10.1021/acs.jmedchem.5b00499 Unchecked 2
25897704 10.1021/acs.jmedchem.5b00499 Hepatitis C virus 2
29952567 10.1021/acs.jmedchem.8b00521 Phosphatidylinositol 4-kinase beta 2
23726345 10.1016/j.bmcl.2013.04.077 rhinovirus A16 2
23726345 10.1016/j.bmcl.2013.04.077 rhinovirus B14 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
23726345 10.1016/j.bmcl.2013.04.077 Unchecked 1
25897704 10.1021/acs.jmedchem.5b00499 Human rhinovirus sp. 1
24900715 10.1021/ml400095m Phosphatidylinositol 4-kinase beta 1
23726345 10.1016/j.bmcl.2013.04.077 Liver microsomes 1
23726345 10.1016/j.bmcl.2013.04.077 Cytochrome P450 3A4 1
23726345 10.1016/j.bmcl.2013.04.077 Phosphatidylinositol 4-kinase beta 1
23726345 10.1016/j.bmcl.2013.04.077 Human rhinovirus sp. 1
23726345 10.1016/j.bmcl.2013.04.077 Enterovirus A71 1
23726345 10.1016/j.bmcl.2013.04.077 Echovirus 1
23726345 10.1016/j.bmcl.2013.04.077 NON-PROTEIN TARGET 1
23726345 10.1016/j.bmcl.2013.04.077 Coxsackievirus B4 1

Data from ChEMBL 36 via Core Engine