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Compound Detail

CHEMBL571882

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COc1ccc2c(c1)OCC/C=C\CCCCN(C[C@@H](O)[C@H](Cc1ccccc1)NC(=O)O[C@H]1CO[C@H]3OCC[C@H]31)S2(=O)=O

Basic Information

ChEMBL ID CHEMBL571882
Phase Preclinical
Structure Type MOL
InChI Key ZQJBDIZBNGQJDT-ZMJCUMBHSA-N
4
Targets
22
Activities
3
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

630.8
MW (Da)
3.65
ALogP
9
HBA
2
HBD
132.9
PSA (Ų)
0.42
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C32H42N2O9S
MW 630.76
Aromatic Rings 2
Heavy Atoms 44
NP-Likeness 0.36

Activity Summary

EC50 18 meas. best 8.7
IC50 2 meas. best 8.34
Ki 2 meas. best 10.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protease
CHEMBL2366517
Ki 10.92 10.92 0.0 1
Unchecked
CHEMBL612545
Ki 10.92 10.92 0.0 1
Human immunodeficiency virus 1
CHEMBL378
EC50 8.7 7.5256 2.0 16
Human immunodeficiency virus 1
CHEMBL378
IC50 8.34 8.34 4.6 1
Unchecked
CHEMBL612545
IC50 8.34 8.34 4.6 1
Human immunodeficiency virus 2
CHEMBL380
EC50 8.0 7.885 10.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.012 nM 10.92 Inhibition of HIV protease 21381769
Protease Ki = 0.012 nM 10.92 Inhibition of HIV1 protease 19746963
Human immunodeficiency virus 1 EC50 = 2.0 nM 8.7 Antiviral activity against HIV1 LAI infected in human MT2 cells by MTT assay 20439612
Unchecked IC50 = 4.6 nM 8.34 Inhibition of HIV protease 21381769
Human immunodeficiency virus 1 IC50 = 4.6 nM 8.34 Antiviral activity against HIV1 LAI infected in human MT2 cells by MTT assay 19746963
Human immunodeficiency virus 1 EC50 = 5.0 nM 8.3 Antiviral activity against wild type HIV1 NL4-3 infected in human MT4 cells by M... 20439612
Human immunodeficiency virus 1 EC50 = 5.0 nM 8.3 Antiviral activity against wild type HIV1 ERS104 containing protease L36P mutant... 20439612
Human immunodeficiency virus 2 EC50 = 10.0 nM 8.0 Antiviral activity against HIV2 EHO infected in human MT2 cells by MTT assay 20439612
Human immunodeficiency virus 2 EC50 = 17.0 nM 7.77 Antiviral activity against HIV2 ROD infected in human MT2 cells by MTT assay 20439612
Human immunodeficiency virus 1 EC50 = 20.0 nM 7.7 Antiviral activity against HIV1 expressing protease L10I/G48V/I54V/A71V/I84V/L90... 20439612
Human immunodeficiency virus 1 EC50 = 23.0 nM 7.64 Antiviral activity against HIV1 expressing protease L23I/E34Q/K43I/M46I/I50L/G51... 20439612
Human immunodeficiency virus 1 EC50 = 27.0 nM 7.57 Antiviral activity against multidrug-resistant HIV1 isolate TM containing L10I, ... 20439612
Human immunodeficiency virus 1 EC50 = 33.0 nM 7.48 Antiviral activity against multidrug-resistant HIV1 isolate MM containing L10I, ... 20439612
Human immunodeficiency virus 1 EC50 = 35.0 nM 7.46 Antiviral activity against HIV1 expressing protease L10F/M46I/I54V/V82A mutant i... 20439612
Human immunodeficiency virus 1 EC50 = 37.0 nM 7.43 Antiviral activity against multidrug-resistant HIV1 isolate B containing proteas... 20439612
Human immunodeficiency virus 1 EC50 = 40.0 nM 7.4 Antiviral activity against HIV1 expressing protease L10F/D30N/K45I/A71V/T74S mut... 20439612
Human immunodeficiency virus 1 EC50 = 44.0 nM 7.36 Antiviral activity against multidrug-resistant HIV1 isolate C containing proteas... 20439612
Human immunodeficiency virus 1 EC50 = 57.0 nM 7.24 Antiviral activity against multidrug-resistant HIV1 isolate G containing L10I, V... 20439612
Human immunodeficiency virus 1 EC50 = 73.0 nM 7.14 Antiviral activity against multidrug-resistant HIV1 isolate JSL containing L10I,... 20439612
Human immunodeficiency virus 1 EC50 = 73.0 nM 7.14 Antiviral activity against HIV1 expressing protease L10F/M46M,I/Q61Q mutant infe... 20439612

Literature References

PubMed DOI Target Context # Activities
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 1 25
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 2 2
20439612 10.1128/aac.01766-09 Unchecked 2
20439612 10.1128/aac.01766-09 Human immunodeficiency virus type 1 protease 2
21381769 10.1021/jm1012374 Unchecked 2
19746963 10.1021/jm900695w Human immunodeficiency virus 1 1
19746963 10.1021/jm900695w Protease 1
20439612 10.1128/aac.01766-09 MT2 1
20439612 10.1128/aac.01766-09 ADMET 1
20439612 10.1128/aac.01766-09 Protease 1

Data from ChEMBL 36 via Core Engine