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Compound Detail

CHEMBL1232930

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COc1ccc(S(=O)(=O)N(CC(C)C)C[C@@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CO[C@H]3O[C@@H]4OCC[C@@H]4[C@H]32)cc1

Basic Information

ChEMBL ID CHEMBL1232930
Phase Preclinical
Structure Type MOL
InChI Key QWMNYFXRFHGYGS-DDGGWZRMSA-N
3
Targets
20
Activities
3
Assay Types
0
PK Parameters
10
Publications
0
Known Names

Molecular Properties

604.7
MW (Da)
2.77
ALogP
9
HBA
2
HBD
132.9
PSA (Ų)
0.38
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C30H40N2O9S
MW 604.72
Aromatic Rings 2
Heavy Atoms 42
NP-Likeness 0.10

Activity Summary

EC50 9 meas. best 9.22
Ki 8 meas. best 9.3
IC50 3 meas. best 8.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protease
CHEMBL2366517
Ki 9.3 9.3 0.5 1
Human immunodeficiency virus 1
CHEMBL378
EC50 9.22 8.5589 0.6 9
Human immunodeficiency virus type 1 protease
CHEMBL243
Ki 8.92 8.286 1.2 5
Human immunodeficiency virus type 1 protease
CHEMBL243
IC50 8.74 8.74 1.8 1
Human immunodeficiency virus 1
CHEMBL378
IC50 8.74 8.74 1.8 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protease Ki = 0.5 nM 9.3 Inhibition of HIV-1 wildtype protease using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-... 23298236
Human immunodeficiency virus 1 EC50 = 0.6 nM 9.22 Antiviral activity against wild type HIV1 ERS104pre infected in human PBMC cells... 26799988
Human immunodeficiency virus 1 EC50 = 0.8 nM 9.1 Antiviral activity against multidrug-resistant HIV1-C infected in phytohemagglut... 26799988
Human immunodeficiency virus type 1 protease Ki = 1.2 nM 8.92 Inhibition of HIV-1 protease R8Q mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Ar... 23298236
Human immunodeficiency virus 1 IC50 = 1.8 nM 8.74 Antiviral activity against HIV1 LAV 23947685
Human immunodeficiency virus 1 IC50 = 1.8 nM 8.74 Antiviral activity against HIV1 LAV assessed as inhibition of virus-induced cyto... 26799988
Human immunodeficiency virus type 1 protease IC50 = 1.8 nM 8.74 Inhibition of HIV-1 protease 34213340
Human immunodeficiency virus 1 EC50 = 2.1 nM 8.68 Antiviral activity against multidrug-resistant HIV1-TM infected in phytohemagglu... 26799988
Human immunodeficiency virus 1 EC50 = 2.5 nM 8.6 Antiviral activity against multidrug-resistant HIV1-JSL infected in phytohemaggl... 26799988
Human immunodeficiency virus 1 EC50 = 2.5 nM 8.6 Antiviral activity against multidrug-resistant HIV1-MM infected in phytohemagglu... 26799988
Human immunodeficiency virus 1 EC50 = 2.6 nM 8.59 Antiviral activity against multidrug-resistant HIV1-G infected in phytohemagglut... 26799988
Human immunodeficiency virus type 1 protease Ki = 3.2 nM 8.49 Inhibition of HIV-1 protease V82A mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-A... 23298236
Human immunodeficiency virus 1 EC50 = 3.4 nM 8.47 Antiviral activity against multidrug-resistant HIV1-B infected in phytohemagglut... 26799988
Human immunodeficiency virus type 1 protease Ki = 3.5 nM 8.46 Inhibition of HIV-1 protease I54M mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-A... 23298236
Human immunodeficiency virus 1 EC50 = 5.6 nM 8.25 Antiviral activity against darunavir-resistant HIV1 10P infected in phytohemaggl... 26799988
Human immunodeficiency virus type 1 protease Ki = 8.9 nM 8.05 Inhibition of HIV-1 protease D30N mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-A... 23298236
Human immunodeficiency virus 1 EC50 = 30.0 nM 7.52 Antiviral activity against darunavir-resistant HIV1 20P infected in phytohemaggl... 26799988
Human immunodeficiency virus type 1 protease Ki = 30.9 nM 7.51 Inhibition of HIV-1 protease I50V mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-A... 23298236

Literature References

PubMed DOI Target Context # Activities
26799988 10.1021/acs.jmedchem.5b01697 Human immunodeficiency virus 1 18
23298236 10.1021/jm301519z Human immunodeficiency virus type 1 protease 5
23298236 10.1021/jm301519z Unchecked 5
23590295 10.1021/jm400231v Human immunodeficiency virus type 1 protease 4
23298236 10.1021/jm301519z Protease 1
23590295 10.1021/jm400231v Protease 1
23947685 10.1021/jm400768f Protease 1
23947685 10.1021/jm400768f Human immunodeficiency virus 1 1
34213340 10.1021/acs.jmedchem.1c00790 Human immunodeficiency virus type 1 protease 1
26799988 10.1021/acs.jmedchem.5b01697 Human immunodeficiency virus type 1 protease 1

Data from ChEMBL 36 via Core Engine