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Compound Detail

CHEMBL4203293

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COc1cc(NC(C(=O)c2c[nH]c3ccccc23)c2ccccc2)cc(OCCO)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4203293
Phase Preclinical
Structure Type MOL
InChI Key CDQMJQBQACODEJ-UHFFFAOYSA-N
6
Targets
10
Activities
2
Assay Types
10
PK Parameters
18
Publications
0
Known Names

Molecular Properties

416.5
MW (Da)
4.58
ALogP
5
HBA
3
HBD
83.6
PSA (Ų)
0.35
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H24N2O4
MW 416.48
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -0.48

Activity Summary

EC50 8 meas. best 7.92
IC50 2 meas. best 5.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
dengue virus type 2
CHEMBL613966
 EC50 7.92 7.26 12.0 5
dengue virus type 1
CHEMBL613360
 EC50 6.75 6.75 180.0 1
dengue virus type 3
CHEMBL612717
 EC50 6.0 6.0 1000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.51 5.51 3100.0 1
dengue virus type 4
CHEMBL613728
 EC50 5.41 5.41 3900.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 5.36 5.36 4400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3049.88 ng.hr.mL-1 Rattus norvegicus
CL 35.0 mL.min-1.kg-1 Rattus norvegicus
CL 8.0 mL.min-1.g-1 Homo sapiens
CL 37.0 mL.min-1.g-1 Rattus norvegicus
CL 201.0 mL.min-1.g-1 Mus musculus
CL 34.7 mL.min-1.kg-1 Rattus norvegicus
CL 54.0 mL.min-1.kg-1 Mus musculus
Cmax 706.0 nM Rattus norvegicus
F 64.0 % Rattus norvegicus
T1/2 2.4 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
dengue virus type 2 EC50 = 12.0 nM 7.92 Antiviral activity against Dengue virus 2 Rega infected in African green monkey ... 30149709
dengue virus type 2 EC50 = 32.0 nM 7.5 Antiviral activity against DENV-2 16681 infected in african green monkey Vero ce... 37389813
dengue virus type 2 EC50 = 49.0 nM 7.31 Antiviral activity against DENV-2 16681 expressing eGFP infected in african gree... 37389813
dengue virus type 2 EC50 = 59.0 nM 7.23 Antiviral activity against Dengue virus 2 Rega infected in African green monkey ... 30149709
dengue virus type 1 EC50 = 180.0 nM 6.75 Antiviral activity against DENV-1 TC974#666 infected in african green monkey Ver... 37389813
dengue virus type 2 EC50 = 456.0 nM 6.34 Antiviral activity against Dengue virus 2 Rega infected in African green monkey ... 30149709
dengue virus type 3 EC50 = 1000.0 nM 6.0 Antiviral activity against DENV-3 H87 infected in african green monkey Vero cell... 37389813
Cytochrome P450 2C9 IC50 = 3100.0 nM 5.51 Inhibition of CYP2C9 (unknown origin) 30149709
dengue virus type 4 EC50 = 3900.0 nM 5.41 Antiviral activity against DENV-4 H241 infected in african green monkey Vero cel... 37389813
Cytochrome P450 2C19 IC50 = 4400.0 nM 5.36 Inhibition of CYP2C19 (unknown origin) 30149709

Literature References

PubMed DOI Target Context # Activities
30149709 10.1021/acs.jmedchem.8b00913 ADMET 10
30149709 10.1021/acs.jmedchem.8b00913 Rattus norvegicus 6
37389813 10.1021/acs.jmedchem.3c00403 ADMET 5
37389813 10.1021/acs.jmedchem.3c00403 No relevant target 4
30149709 10.1021/acs.jmedchem.8b00913 Vero 3
30149709 10.1021/acs.jmedchem.8b00913 No relevant target 3
30149709 10.1021/acs.jmedchem.8b00913 dengue virus type 2 3
37389813 10.1021/acs.jmedchem.3c00403 dengue virus type 2 2
30149709 10.1021/acs.jmedchem.8b00913 Cytochrome P450 1A2 1
30149709 10.1021/acs.jmedchem.8b00913 Cytochrome P450 2C19 1
30149709 10.1021/acs.jmedchem.8b00913 Cytochrome P450 2C9 1
30149709 10.1021/acs.jmedchem.8b00913 Cytochrome P450 2D6 1
30149709 10.1021/acs.jmedchem.8b00913 Cytochrome P450 3A4 1
30149709 10.1021/acs.jmedchem.8b00913 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37389813 10.1021/acs.jmedchem.3c00403 Vero 1
37389813 10.1021/acs.jmedchem.3c00403 dengue virus type 1 1
37389813 10.1021/acs.jmedchem.3c00403 dengue virus type 3 1
37389813 10.1021/acs.jmedchem.3c00403 dengue virus type 4 1

Data from ChEMBL 36 via Core Engine