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Compound Detail

CHEMBL300891

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Cc1ccccc1CNC(=O)[C@H]1N(C(=O)[C@@H](O)[C@H](Cc2ccccc2)NC(=O)c2cccc(O)c2C)CSC1(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL300891
Phase Preclinical
Structure Type MOL
InChI Key CUFQBQOBLVLKRF-RZDMPUFOSA-N
6
Targets
15
Activities
3
Assay Types
22
PK Parameters
20
Publications
0
Known Names

Molecular Properties

575.7
MW (Da)
3.71
ALogP
6
HBA
4
HBD
119.0
PSA (Ų)
0.31
QED
1
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C32H37N3O5S
MW 575.73
Aromatic Rings 3
Heavy Atoms 41
NP-Likeness -0.05

Activity Summary

EC50 8 meas. best 7.58
Ki 5 meas. best 10.51
IC50 2 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protease
CHEMBL2366517
 Ki 10.51 10.485 0.0 2
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 9.48 9.48 0.3 2
CEM-SS
CHEMBL614548
 IC50 8.15 8.15 7.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.58 7.2457 26.0 7
Plasmepsin II
CHEMBL4414
 IC50 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
 Ki 6.96 6.96 110.0 1
Protease
CHEMBL2366517
 EC50 5.56 5.56 2730.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 29696.15 ng.hr.mL-1 Canis lupus familiaris
AUC 9683.78 ng.hr.mL-1 Canis lupus familiaris
AUC 11025.23 ng.hr.mL-1 Canis lupus familiaris
AUC 3742.24 ng.hr.mL-1 Canis lupus familiaris
CL 14.67 mL.min-1.kg-1 Canis lupus familiaris
CL 15.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 700.0 nM Rattus norvegicus
Cmax 4020.0 nM Canis lupus familiaris
Cmax 5300.0 nM Canis lupus familiaris
Cmax 3100.0 nM Canis lupus familiaris
F 41.0 % Rattus norvegicus
F 32.6 % Canis lupus familiaris
F 37.1 % Canis lupus familiaris
F 25.0 % Canis lupus familiaris
F 33.0 % Rattus norvegicus
F 33.0 % Rattus norvegicus
T1/2 1.55 hr Rattus norvegicus
Tmax 1.0 hr Rattus norvegicus
Tmax 1.5 hr Canis lupus familiaris
Tmax 1.0 hr Canis lupus familiaris
Tmax 0.5 hr Canis lupus familiaris
Tmax 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protease Ki = 0.031 nM 10.51 Inhibition of HIV1 recombinant protease after 15 mins by fluorescence assay 19954246
Protease Ki = 0.035 nM 10.46 Inhibition of HIV1 protease 17981045
Human immunodeficiency virus type 1 protease Ki = 0.33 nM 9.48 Inhibition of recombinant HIV-1 protease (NY-5) 10346931
Human immunodeficiency virus type 1 protease Ki = 0.33 nM 9.48 Inhibition of HIV1 protease 36096342
CEM-SS IC50 = 7.0 nM 8.15 Antiviral activity was determined based on inhibition of HIV-1 IIIB induced cyto... 10346931
Human immunodeficiency virus 1 EC50 = 26.0 nM 7.58 Antiviral activity against HIV1 3B 17981045
Plasmepsin II IC50 = 30.0 nM 7.52 Inhibition of Plasmodium falciparum plasmepsin-2 19635672
Human immunodeficiency virus 1 EC50 = 33.0 nM 7.48 Antiviral activity against HIV1 3B infected in human MT4 cells assessed as inhib... 19954246
Human immunodeficiency virus 1 EC50 = 52.0 nM 7.28 Antiviral activity against HIV1 3B in presence of 50% human serum 17981045
Human immunodeficiency virus 1 EC50 = 60.0 nM 7.22 Antiviral activity against HIV1 pNL4-3 infected in human MT4 cells assessed as i... 19954246
Human immunodeficiency virus 1 EC50 = 60.0 nM 7.22 Antiviral activity against wild-type HIV1 pNL4-3 infected in human MT4 cells ass... 29852069
Human immunodeficiency virus 1 EC50 = 100.0 nM 7.0 Antiviral activity against indinavir-resistant HIV1 harboring L10R/M46I/L63P/V82... 19954246
Unchecked Ki = 110.0 nM 6.96 Inhibition of Plasmodium malariae plasmepsin-4 19635672
Human immunodeficiency virus 1 EC50 = 114.0 nM 6.94 Antiviral activity against wild-type HIV1 3B infected in human MT4 cells assesse... 29852069
Protease EC50 = 2730.0 nM 5.56 Inhibition of protease L10F/V32I/M46I/I47V/Q58E/I84V mutant in HIV1 A17 infected... 29852069

Literature References

PubMed DOI Target Context # Activities
10346931 10.1021/jm980637h Canis familiaris 10
17981045 10.1016/j.bmc.2007.10.062 Liver microsomes 8
17981045 10.1016/j.bmc.2007.10.062 Canis familiaris 7
17981045 10.1016/j.bmc.2007.10.062 Liver 5
36096342 10.1016/j.bmcl.2022.128983 ADMET 4
19954246 10.1021/jm9005115 Human immunodeficiency virus 1 4
10346931 10.1021/jm980637h Rattus norvegicus 3
10346931 10.1021/jm980637h ADMET 3
29852069 10.1021/acs.jmedchem.7b01709 Human immunodeficiency virus 1 3
19954246 10.1021/jm9005115 Protease 3
10346931 10.1021/jm980637h CEM-SS 2
29852069 10.1021/acs.jmedchem.7b01709 Protease 2
17981045 10.1016/j.bmc.2007.10.062 Human immunodeficiency virus 1 2
10346931 10.1021/jm980637h Human immunodeficiency virus type 1 protease 2
19635672 10.1016/j.bmc.2009.06.065 Unchecked 1
19635672 10.1016/j.bmc.2009.06.065 Plasmepsin II 1
17981045 10.1016/j.bmc.2007.10.062 Protease 1
29852069 10.1021/acs.jmedchem.7b01709 Unchecked 1
29852069 10.1021/acs.jmedchem.7b01709 MT4 1
36096342 10.1016/j.bmcl.2022.128983 Human immunodeficiency virus type 1 protease 1

Data from ChEMBL 36 via Core Engine