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Compound Detail

CHEMBL469086

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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]3OCC[C@H]32)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL469086
Phase Preclinical
Structure Type MOL
InChI Key BINXAIIXOUQUKC-UIPNDDLNSA-N
4
Targets
24
Activities
3
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

562.7
MW (Da)
2.80
ALogP
8
HBA
2
HBD
123.6
PSA (Ų)
0.40
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C28H38N2O8S
MW 562.69
Aromatic Rings 2
Heavy Atoms 39
NP-Likeness 0.08

Activity Summary

EC50 10 meas. best 9.46
Ki 9 meas. best 11.0
IC50 5 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protease
CHEMBL2366517
 Ki 11.0 10.88 0.0 5
Unchecked
CHEMBL612545
 Ki 10.85 10.85 0.0 1
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.52 9.165 0.3 4
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.46 8.737 0.3 10
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 8.96 8.96 1.1 1
Protease
CHEMBL2366517
 IC50 8.85 8.85 1.4 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2695.0 ng.hr.mL-1 Canis lupus familiaris
Cmax 2098.85 nM Canis lupus familiaris
T1/2 1.474 hr Canis lupus familiaris
Tmax 0.6 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protease Ki = 0.01 nM 11.0 Inhibition of HIV1 protease dimerization in MT2 cells 17635930
Unchecked Ki = 0.014 nM 10.85 Inhibition of wild-type HIV-1 protease 28958624
Protease Ki = 0.014 nM 10.85 Inhibition of HIV1 protease 19746963
Protease Ki = 0.014 nM 10.85 Inhibition of HIV1 protease 19323561
Protease Ki = 0.014 nM 10.85 Inhibition of HIV1 protease 18783203
Protease Ki = 0.014 nM 10.85 Inhibition of HIV1 protease 17900913
Human immunodeficiency virus 1 IC50 = 0.3 nM 9.52 Antiviral activity against HIV1 LAI in MT2 cells 17635930
Human immunodeficiency virus 1 EC50 = 0.35 nM 9.46 Antiviral activity against wild type HIV1 3B infected in human MT2 cells assesse... -
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Effective concentration against human immunodeficiency virus type 1 strains; (0.... 15743172
Human immunodeficiency virus 1 IC50 = 0.5 nM 9.3 Antiviral activity against protease inhibitor resistant HIV1 isolates 19323561
Human immunodeficiency virus 1 EC50 = 0.5 nM 9.3 Antiviral activity against HIV1 Lai infected in human MT2 cells 28418652
Human immunodeficiency virus 1 EC50 = 0.5888 nM 9.23 Effective concentration of against HIV Wild Type (IIIB) strain 15771427
Human immunodeficiency virus type 1 protease Ki = 1.1 nM 8.96 Inhibitory activity against HIV-1 protease 9871583
Human immunodeficiency virus 1 IC50 = 1.2 nM 8.92 Antiviral activity against HIV1 LAI infected in human MT2 cells by MTT assay 19746963
Human immunodeficiency virus 1 IC50 = 1.2 nM 8.92 Antiviral activity against HIV-1 harboring protease I50V mutant 28958624
Protease IC50 = 1.4 nM 8.85 Inhibition of HIV1 protease 19323561
Human immunodeficiency virus 1 EC50 = 2.239 nM 8.65 Effective concentration against PI-Resistant HIV strain (M3) 15771427
Human immunodeficiency virus 1 EC50 = 2.884 nM 8.54 Effective concentration against PI-Resistant HIV strain (M5) 15771427
Human immunodeficiency virus 1 EC50 = 4.467 nM 8.35 Effective concentration as average activity on mutant HIV panel (AVMUT) 15771427
Human immunodeficiency virus 1 EC50 = 4.677 nM 8.33 Effective concentration against PI-Resistant HIV strain (M4) 15771427

Literature References

PubMed DOI Target Context # Activities
15771427 10.1021/jm049560p ADMET 7
15771427 10.1021/jm049560p Human immunodeficiency virus 1 7
- 10.1039/C1MD00147G Human immunodeficiency virus 1 7
17635930 10.1074/jbc.m703938200 Protease 2
19323561 10.1021/jm900064c Protease 2
18783203 10.1021/jm8004543 Human immunodeficiency virus 1 1
28418652 10.1021/acs.jmedchem.7b00172 Unchecked 1
28418652 10.1021/acs.jmedchem.7b00172 Human immunodeficiency virus 1 1
28958624 10.1016/j.bmcl.2017.09.003 Human immunodeficiency virus 1 1
28958624 10.1016/j.bmcl.2017.09.003 Unchecked 1
- 10.1039/C1MD00147G Protease 1
19746963 10.1021/jm900695w Human immunodeficiency virus 1 1
19746963 10.1021/jm900695w Protease 1
19323561 10.1021/jm900064c Human immunodeficiency virus 1 1
9871583 10.1016/s0960-894x(98)00098-5 Human immunodeficiency virus type 1 protease 1
18783203 10.1021/jm8004543 Protease 1
17635930 10.1074/jbc.m703938200 Human immunodeficiency virus 1 1
17900913 10.1016/j.bmc.2007.09.010 Protease 1
17900913 10.1016/j.bmc.2007.09.010 Human immunodeficiency virus 1 1
15743172 10.1021/jm040158k Human immunodeficiency virus 1 1

Data from ChEMBL 36 via Core Engine