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Compound Detail

CHEMBL577560

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COc1ccc2c(c1)OCCC/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 CHEMBL577560
Phase Preclinical
Structure Type MOL
InChI Key PAUIHFDXSPYWNF-SSJVAFASSA-N
3
Targets
20
Activities
3
Assay Types
0
PK Parameters
7
Publications
0
Known Names

Molecular Properties

644.8
MW (Da)
4.04
ALogP
9
HBA
2
HBD
132.9
PSA (Ų)
0.41
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 C33H44N2O9S
MW 644.79
Aromatic Rings 2
Heavy Atoms 45
NP-Likeness 0.31

Activity Summary

EC50 18 meas. best 8.4
IC50 1 meas. best 8.54
Ki 1 meas. best 9.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protease
CHEMBL2366517
Ki 9.05 9.05 0.9 1
Human immunodeficiency virus 1
CHEMBL378
IC50 8.54 8.54 2.9 1
Human immunodeficiency virus 1
CHEMBL378
EC50 8.4 7.2706 4.0 16
Human immunodeficiency virus 2
CHEMBL380
EC50 7.75 7.675 18.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protease Ki = 0.9 nM 9.05 Inhibition of HIV1 protease 19746963
Human immunodeficiency virus 1 IC50 = 2.9 nM 8.54 Antiviral activity against HIV1 LAI infected in human MT2 cells by MTT assay 19746963
Human immunodeficiency virus 1 EC50 = 4.0 nM 8.4 Antiviral activity against HIV1 LAI infected in human MT2 cells by MTT assay 20439612
Human immunodeficiency virus 1 EC50 = 7.0 nM 8.15 Antiviral activity against wild type HIV1 ERS104 containing protease L36P mutant... 20439612
Human immunodeficiency virus 1 EC50 = 9.0 nM 8.05 Antiviral activity against wild type HIV1 NL4-3 infected in human MT4 cells by M... 20439612
Human immunodeficiency virus 2 EC50 = 18.0 nM 7.75 Antiviral activity against HIV2 EHO infected in human MT2 cells by MTT assay 20439612
Human immunodeficiency virus 2 EC50 = 25.0 nM 7.6 Antiviral activity against HIV2 ROD infected in human MT2 cells by MTT assay 20439612
Human immunodeficiency virus 1 EC50 = 28.0 nM 7.55 Antiviral activity against multidrug-resistant HIV1 isolate G containing L10I, V... 20439612
Human immunodeficiency virus 1 EC50 = 29.0 nM 7.54 Antiviral activity against multidrug-resistant HIV1 isolate C containing proteas... 20439612
Human immunodeficiency virus 1 EC50 = 30.0 nM 7.52 Antiviral activity against HIV1 expressing protease L23I/E34Q/K43I/M46I/I50L/G51... 20439612
Human immunodeficiency virus 1 EC50 = 41.0 nM 7.39 Antiviral activity against HIV1 expressing protease L10F/D30N/K45I/A71V/T74S mut... 20439612
Human immunodeficiency virus 1 EC50 = 46.0 nM 7.34 Antiviral activity against HIV1 expressing protease L10I/G48V/I54V/A71V/I84V/L90... 20439612
Human immunodeficiency virus 1 EC50 = 55.0 nM 7.26 Antiviral activity against multidrug-resistant HIV1 isolate MM containing L10I, ... 20439612
Human immunodeficiency virus 1 EC50 = 72.0 nM 7.14 Antiviral activity against multidrug-resistant HIV1 isolate TM containing L10I, ... 20439612
Human immunodeficiency virus 1 EC50 = 89.0 nM 7.05 Antiviral activity against multidrug-resistant HIV1 isolate B containing proteas... 20439612
Human immunodeficiency virus 1 EC50 = 190.0 nM 6.72 Antiviral activity against HIV1 expressing protease L10I/L24I/M46I/V82I/I84V mut... 20439612
Human immunodeficiency virus 1 EC50 = 210.0 nM 6.68 Antiviral activity against multidrug-resistant HIV1 isolate JSL containing L10I,... 20439612
Human immunodeficiency virus 1 EC50 = 250.0 nM 6.6 Antiviral activity against HIV1 expressing protease L10F/M46M,I/Q61Q mutant infe... 20439612
Human immunodeficiency virus 1 EC50 = 330.0 nM 6.48 Antiviral activity against HIV1 expressing protease L10F/M46I/T91S mutant infect... 20439612
Human immunodeficiency virus 1 EC50 = 350.0 nM 6.46 Antiviral activity against HIV1 expressing protease L10F/M46I/I54V/V82A mutant i... 20439612

Literature References

PubMed DOI Target Context # Activities
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 1 28
20439612 10.1128/aac.01766-09 Human immunodeficiency virus 2 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