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Compound Detail

CHEMBL4094163

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Cc1cc(/C=C/C#N)cc(C)c1Oc1nc(NC2CCN(Cc3ccc(S(N)(=O)=O)cc3)CC2)nc2ccsc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4094163
Phase Preclinical
Structure Type MOL
InChI Key GVCHBMCBPBRORW-ONEGZZNKSA-N
8
Targets
36
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

574.7
MW (Da)
5.36
ALogP
9
HBA
2
HBD
134.2
PSA (Ų)
0.27
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H30N6O3S2
MW 574.73
Aromatic Rings 4
Heavy Atoms 40
NP-Likeness -1.38

Activity Summary

EC50 19 meas. best 9.02
IC50 17 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 EC50 9.02 8.5143 1.0 7
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.02 8.1642 1.0 12
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 7.0 6.83 99.0 9
Unchecked
CHEMBL612545
 IC50 6.8 6.8 160.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 6.75 6.7367 180.0 3
Cytochrome P450 3A4
CHEMBL340
 IC50 5.23 5.23 5920.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.88 4.88 13200.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.82 4.82 15200.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.67 4.67 21200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2316.8 ng.hr.mL-1 Rattus norvegicus
AUC 2692.2 ng.hr.mL-1 Rattus norvegicus
AUC 1367.3 ng.hr.mL-1 Rattus norvegicus
AUC 1386.0 ng.hr.mL-1 Rattus norvegicus
CL 847.3 mL.min-1.g-1 Homo sapiens
Cmax 962.02 nM Rattus norvegicus
Cmax 3857.46 nM Rattus norvegicus
F 16.19 % Rattus norvegicus
MRT 5.54 hr Rattus norvegicus
MRT 1.69 hr Rattus norvegicus
T1/2 3.93 hr Rattus norvegicus
T1/2 1.34 hr Rattus norvegicus
T1/2 0.02667 hr Homo sapiens
Tmax 1.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.96 nM 9.02 Antiviral activity against HIV1 expressing RT K103N mutant infected in human MT4... 32293182
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 0.958 nM 9.02 Inhibition of HIV1 3B reverse transcriptase K103N mutant infected in human MT4 c... 28481112
Human immunodeficiency virus 1 EC50 = 1.22 nM 8.91 Antiviral activity against wild type HIV1 3B harboring reverse transcriptase inf... 28481112
Human immunodeficiency virus 1 EC50 = 1.22 nM 8.91 Antiviral activity against HIV1 3B infected in human MT4 cells assessed as prote... 32293182
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 1.34 nM 8.87 Inhibition of HIV1 3B reverse transcriptase L100I mutant infected in human MT4 c... 28481112
Human immunodeficiency virus 1 EC50 = 1.34 nM 8.87 Antiviral activity against HIV1 expressing RT L100I mutant infected in human MT4... 32293182
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 2.7 nM 8.57 Inhibition of HIV1 3B reverse transcriptase F227L/V106A double mutant infected i... 28481112
Human immunodeficiency virus 1 EC50 = 2.7 nM 8.57 Antiviral activity against HIV1 expressing RT F227L + V106A mutant infected in h... 32293182
Human immunodeficiency virus 1 EC50 = 2.7 nM 8.57 Antiviral activity against HIV1 3B infected in human MT4 cells grown under 30 pa... 32293182
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 4.74 nM 8.32 Inhibition of HIV1 3B reverse transcriptase E138K mutant infected in human MT4 c... 28481112
Human immunodeficiency virus 1 EC50 = 4.74 nM 8.32 Antiviral activity against HIV1 expressing RT E138K mutant infected in human MT4... 32293182
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 5.0 nM 8.3 Inhibition of HIV1 3B reverse transcriptase Y181C mutant infected in human MT4 c... 28481112
Human immunodeficiency virus 1 EC50 = 5.0 nM 8.3 Antiviral activity against HIV1 expressing RT Y181C mutant infected in human MT4... 32293182
Human immunodeficiency virus 1 EC50 = 5.5 nM 8.26 Antiviral activity against HIV1 RES056 infected in human MT4 cells assessed as p... 32293182
Human immunodeficiency virus 1 EC50 = 5.45 nM 8.26 Antiviral activity against HIV1 expressing RT Y188L mutant infected in human MT4... 32293182
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 5.5 nM 8.26 Inhibition of HIV1 RES056 reverse transcriptase K103N/Y181C double mutant infect... 28481112
Human immunodeficiency virus type 1 reverse transcriptase EC50 = 5.45 nM 8.26 Inhibition of HIV1 3B reverse transcriptase Y188L mutant infected in human MT4 c... 28481112
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 101.0 nM 7.0 Inhibition of HIV1 RT in presence of reconstituted template and viral nucleotide... 32293182
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 99.0 nM 7.0 Inhibition of HIV1 RT L100I mutant in presence of reconstituted template and vir... 32293182
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 101.0 nM 7.0 Inhibition of wild type HIV1 reverse transcriptase assessed as reduction in biot... 34432448

Literature References

PubMed DOI Target Context # Activities
28481112 10.1021/acs.jmedchem.7b00332 Rattus norvegicus 22
32293182 10.1021/acs.jmedchem.0c00117 Human immunodeficiency virus 1 21
28481112 10.1021/acs.jmedchem.7b00332 Human immunodeficiency virus type 1 reverse transcriptase 16
28481112 10.1021/acs.jmedchem.7b00332 Unchecked 11
32293182 10.1021/acs.jmedchem.0c00117 Human immunodeficiency virus type 1 reverse transcriptase 8
32293182 10.1021/acs.jmedchem.0c00117 Unchecked 8
34432448 10.1021/acs.jmedchem.1c01015 ADMET 3
33567378 10.1016/j.ejmech.2021.113204 No relevant target 3
32293182 10.1021/acs.jmedchem.0c00117 No relevant target 3
28481112 10.1021/acs.jmedchem.7b00332 Mus musculus 2
28481112 10.1021/acs.jmedchem.7b00332 Human immunodeficiency virus 1 2
32293182 10.1021/acs.jmedchem.0c00117 Cytochrome P450 2C9 1
34432448 10.1021/acs.jmedchem.1c01015 Voltage-gated inwardly rectifying potassium channel KCNH2 1
32293182 10.1021/acs.jmedchem.0c00117 Cytochrome P450 3A4 1
32293182 10.1021/acs.jmedchem.0c00117 MT4 1
32293182 10.1021/acs.jmedchem.0c00117 Cytochrome P450 1A2 1
32293182 10.1021/acs.jmedchem.0c00117 Cytochrome P450 2C19 1
32293182 10.1021/acs.jmedchem.0c00117 Cytochrome P450 2D6 1
28481112 10.1021/acs.jmedchem.7b00332 Voltage-gated inwardly rectifying potassium channel KCNH2 1
28481112 10.1021/acs.jmedchem.7b00332 MT4 1

Data from ChEMBL 36 via Core Engine