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Compound Detail

CHEMBL3742114

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CCOC(=O)C1=C(CN2CCOCC2)NC(c2nccs2)=NC1c1ccc(F)cc1Br
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3742114
Phase Preclinical
Structure Type MOL
InChI Key SQGRDKSRFFUBBU-UHFFFAOYSA-N
3
Targets
42
Activities
2
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

509.4
MW (Da)
3.29
ALogP
8
HBA
1
HBD
76.0
PSA (Ų)
0.60
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22BrFN4O3S
MW 509.40
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness -1.62

Activity Summary

EC50 38 meas. best 9.0
IC50 4 meas. best 7.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Core antigen
CHEMBL1075091
 EC50 9.0 7.5872 1.0 25
Hepatitis B virus
CHEMBL613497
 EC50 8.2 7.4677 6.3 13
Hepatitis B virus
CHEMBL613497
 IC50 7.92 7.92 12.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 6.07 5.97 860.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 405.0 ng.hr.mL-1 Rattus norvegicus
AUC 90.0 ng.hr.mL-1 Rattus norvegicus
AUC 1472.0 ng.hr.mL-1 Canis lupus familiaris
AUC 1008.0 ng.hr.mL-1 Canis lupus familiaris
AUC 4353.0 ng.hr.mL-1 Canis lupus familiaris
AUC 695.0 ng.hr.mL-1 Canis lupus familiaris
AUC 2761.0 ng.hr.mL-1 Canis lupus familiaris
AUC 8466.0 ng.hr.mL-1 Canis lupus familiaris
AUC 2829.0 ng.hr.mL-1 Canis lupus familiaris
CL 20.0 mL.min-1.kg-1 Homo sapiens
CL 485.0 mL.min-1.kg-1 Mus musculus
CL 202.0 mL.min-1.kg-1 Canis lupus familiaris
CL 82.2 mL.min-1.kg-1 Rattus norvegicus
CL 16.6 mL.min-1.kg-1 Canis lupus familiaris
CL 17.9 mL.min-1.kg-1 Canis lupus familiaris
CL 662.7 mL.min-1.g-1 Homo sapiens
CL 596.4 mL.min-1.kg-1 Homo sapiens
Cmax 2793.48 nM Canis lupus familiaris
Cmax 767.57 nM Canis lupus familiaris
Cmax 136.0 ng/mg Canis lupus familiaris
Cmax 698.0 ng/mg Canis lupus familiaris
Cmax 1181.0 ng/mg Canis lupus familiaris
Cmax 524.0 ng/mg Canis lupus familiaris
F 8.9 % Rattus norvegicus
F 23.8 % Canis lupus familiaris
F 15.6 % Canis lupus familiaris
Fu 0.001 - Homo sapiens
Fu 0.018 - Canis lupus familiaris
T1/2 17.9 hr Canis lupus familiaris
T1/2 11.5 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Core antigen EC50 = 1.0 nM 9.0 Inhibition of hepatitis B virus capsid assembly infected in human HepG2.215 cell... 28082068
Hepatitis B virus EC50 = 6.3 nM 8.2 Antiviral activity against HBV infected in human HepG2.A64 cells containing reve... 32421339
Hepatitis B virus EC50 = 6.6 nM 8.18 Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as re... 32421339
Hepatitis B virus EC50 = 7.0 nM 8.15 Antiviral activity against HBV infected human HePAD38 cells assessed as reductio... 37974964
Core antigen EC50 = 10.0 nM 8.0 Inhibition of reverse transcriptase M204I mutant expressing telbivudine-resistan... 28082068
Core antigen EC50 = 11.0 nM 7.96 Inhibition of reverse transcriptase M204I mutant expressing lamivudine-resistant... 28082068
Hepatitis B virus EC50 = 11.0 nM 7.96 Antiviral activity against Hepatitis B virus infected in human HepaRG cells asse... 33062174
Hepatitis B virus IC50 = 12.0 nM 7.92 Antiviral activity against HBV infected in human HepG2(2.2.15) cells assessed as... 28383274
Core antigen EC50 = 12.0 nM 7.92 Inhibition of telbivudine-resistant wild type hepatitis B virus capsid assembly ... 28082068
Hepatitis B virus IC50 = 12.0 nM 7.92 Inhibition of HBV DNA replication in HepG2 cells by southern blot analysis -
Core antigen EC50 = 12.0 nM 7.92 Inhibition of reverse transcriptase M204I/S202G double mutant expressing entecav... 28082068
Hepatitis B virus EC50 = 12.0 nM 7.92 Antiviral activity against HBV infected in human HepG2.2.15 cells assessed as re... 37974964
Hepatitis B virus EC50 = 13.0 nM 7.89 Antiviral activity against HBV infected in human HepG2.2.15 replicon cells asses... 29381358
Hepatitis B virus EC50 = 13.0 nM 7.89 Antiviral activity against HBV infected in human HepAD38 cells assessed as reduc... 32421339
Core antigen EC50 = 14.49 nM 7.84 Inhibition of wild type hepatitis B virus capsid assembly in human HepG2.215 cel... 28082068
Core antigen EC50 = 15.0 nM 7.82 Inhibition of reverse transcriptase M204I/V173L double mutant expressing lamivud... 28082068
Core antigen EC50 = 17.1 nM 7.77 Inhibition of wild type hepatitis B virus capsid assembly in human HepG2.215 cel... 28082068
Core antigen EC50 = 18.0 nM 7.75 Inhibition of reverse transcriptase M204I/S202G/M250V triple mutant expressing e... 28082068
Core antigen EC50 = 19.0 nM 7.72 Inhibition of reverse transcriptase L180M/M204V double mutant expressing telbivu... 28082068
Core antigen EC50 = 19.0 nM 7.72 Inhibition of reverse transcriptase M204I/VI73L double mutant expressing lamivud... 28082068

Literature References

PubMed DOI Target Context # Activities
28082068 10.1016/j.bmc.2016.12.017 Canis familiaris 29
28082068 10.1016/j.bmc.2016.12.017 Core antigen 28
32421339 10.1021/acs.jmedchem.0c00292 Hepatitis B virus 15
28082068 10.1016/j.bmc.2016.12.017 Mus musculus 9
29381358 10.1021/acs.jmedchem.7b01914 Canis familiaris 9
28082068 10.1016/j.bmc.2016.12.017 ADMET 7
28688280 10.1016/j.ejmech.2017.06.062 Hepatitis B virus 5
37974964 10.1039/d3md00461a ADMET 5
29381358 10.1021/acs.jmedchem.7b01914 Rattus norvegicus 5
37974964 10.1039/d3md00461a Hepatitis B virus 4
28082068 10.1016/j.bmc.2016.12.017 Unchecked 4
29381358 10.1021/acs.jmedchem.7b01914 Liver 3
37974964 10.1039/d3md00461a No relevant target 3
37974964 10.1039/d3md00461a Voltage-gated inwardly rectifying potassium channel KCNH2 3
29381358 10.1021/acs.jmedchem.7b01914 Cytochrome P450 3A4 2
28082068 10.1016/j.bmc.2016.12.017 Cytochrome P450 2E1 2
29381358 10.1021/acs.jmedchem.7b01914 Plasma 2
28688280 10.1016/j.ejmech.2017.06.062 Core antigen 2
28082068 10.1016/j.bmc.2016.12.017 Cytochrome P450 3A4 2
28082068 10.1016/j.bmc.2016.12.017 Bile acid receptor 2

Data from ChEMBL 36 via Core Engine