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Compound Detail

CHEMBL4471665

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COc1ccc(N(C)C(=O)[C@H](Cc2ccccc2)NC(=O)CN2CCN(S(=O)(=O)c3ccc(N)cc3)CC2=O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4471665
Phase Preclinical
Structure Type MOL
InChI Key REXBCEZWZOLFMN-SANMLTNESA-N
3
Targets
17
Activities
3
Assay Types
25
PK Parameters
18
Publications
0
Known Names

Molecular Properties

579.7
MW (Da)
1.50
ALogP
7
HBA
2
HBD
142.3
PSA (Ų)
0.35
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H33N5O6S
MW 579.68
Aromatic Rings 3
Heavy Atoms 41
NP-Likeness -1.43

Activity Summary

EC50 9 meas. best 7.52
Kd 6 meas. best 6.07
IC50 2 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 IC50 8.05 7.335 9.0 2
Human immunodeficiency virus 2
CHEMBL380
 EC50 7.52 7.52 30.0 2
Human immunodeficiency virus 1
CHEMBL378
 EC50 7.51 6.9814 31.0 7
Structural capsid protein
CHEMBL2366504
 Kd 6.07 5.4283 849.0 6

Pharmacokinetic Data

Parameter Value Units Species
AUC 116.3 ng.hr.mL-1 Rattus norvegicus
AUC 120.6 ng.hr.mL-1 Rattus norvegicus
AUC 505.6 ng.hr.mL-1 Rattus norvegicus
AUC 511.5 ng.hr.mL-1 Rattus norvegicus
CL 342.0 mL.min-1.g-1 Homo sapiens
CL 307.8 mL.min-1.kg-1 Homo sapiens
CL 67.71 mL.min-1.kg-1 Rattus norvegicus
CL 356.0 mL.min-1.kg-1 Homo sapiens
CL 395.6 mL.min-1.g-1 Homo sapiens
CL 343.6 mL.min-1.g-1 Homo sapiens
CL 309.3 mL.min-1.kg-1 Homo sapiens
Cmax 144.56 nM Rattus norvegicus
Cmax 2209.84 nM Rattus norvegicus
F 23.0 % Rattus norvegicus
MRT 1.8 hr Rattus norvegicus
MRT 0.7 hr Rattus norvegicus
T1/2 14.08 hr Homo sapiens
T1/2 0.06833 hr Homo sapiens
T1/2 1.2 hr Rattus norvegicus
T1/2 1.0 hr Rattus norvegicus
T1/2 0.05833 hr Homo sapiens
T1/2 0.06667 hr Homo sapiens
Tmax 0.25 hr Rattus norvegicus
Tmax 0.083 hr Rattus norvegicus
Vd 5.752 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 IC50 = 8.96 nM 8.05 Antiviral activity against HIV1 Env-pseudotyped virus in human U87.CD4.CCR5 targ... 32298111
Human immunodeficiency virus 2 EC50 = 30.0 nM 7.52 Antiviral activity against HIV-2 ROD infected in human MT4 cells assessed as pro... 38054267
Human immunodeficiency virus 2 EC50 = 30.0 nM 7.52 Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as redu... 38054267
Human immunodeficiency virus 1 EC50 = 31.0 nM 7.51 Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as redu... 32298111
Human immunodeficiency virus 1 EC50 = 34.0 nM 7.47 Antiviral activity against wild type HIV-1 ROD infected in human MT4 cells asses... 34592608
Human immunodeficiency virus 1 EC50 = 90.0 nM 7.05 Antiviral activity against HIV1 NL4-3 infected in human TZM-bl cells assessed as... 32298111
Human immunodeficiency virus 1 EC50 = 160.0 nM 6.8 Antiviral activity against wild type HIV-1 IIIB infected in human MT4 cells asse... 34592608
Human immunodeficiency virus 1 EC50 = 210.0 nM 6.68 Antiviral activity against HIV-1 IIIB infected in human MT4 cells assessed as pr... 38054267
Human immunodeficiency virus 1 EC50 = 210.0 nM 6.68 Antiviral activity against HIV1 IIIB infected in human MT4 cells assessed as red... 38054267
Human immunodeficiency virus 1 EC50 = 210.0 nM 6.68 Antiviral activity against HIV1 3B infected in human MT4 cells assessed as reduc... 32298111
Human immunodeficiency virus 1 IC50 = 240.0 nM 6.62 Antiviral activity against HIV1 Env-pseudotyped virus in human U87.CD4.CCR5 targ... 32298111
Structural capsid protein Kd = 849.0 nM 6.07 Binding affinity to HIV-1 NL4.3 monomeric capsid protein assessed as dissociatio... 38054267
Structural capsid protein Kd = 1626.0 nM 5.79 Binding affinity to HIV-1 NL4.3 hexameric capsid protein assessed as dissociatio... 38054267
Structural capsid protein Kd = 2630.0 nM 5.58 Binding affinity to HIV1 NL4-3 capsid protein hexamer by SPR analysis 32298111
Structural capsid protein Kd = 3980.0 nM 5.4 Binding affinity to HIV1 capsid protein hexamer assessed as dissociation constan... 34592608
Structural capsid protein Kd = 13600.0 nM 4.87 Binding affinity to HIV1 NL4-3 capsid protein monomer by SPR analysis 32298111
Structural capsid protein Kd = 13880.0 nM 4.86 Binding affinity to HIV1 capsid protein monomer assessed as dissociation constan... 34592608

Literature References

PubMed DOI Target Context # Activities
32298111 10.1021/acs.jmedchem.0c00015 ADMET 28
32298111 10.1021/acs.jmedchem.0c00015 Human immunodeficiency virus 1 10
34592608 10.1016/j.ejmech.2021.113848 ADMET 8
38054267 10.1021/acs.jmedchem.3c01647 ADMET 8
38054267 10.1021/acs.jmedchem.3c01647 Structural capsid protein 6
32298111 10.1021/acs.jmedchem.0c00015 Structural capsid protein 4
34592608 10.1016/j.ejmech.2021.113848 Human immunodeficiency virus 1 4
38054267 10.1021/acs.jmedchem.3c01647 Human immunodeficiency virus 1 4
32298111 10.1021/acs.jmedchem.0c00015 Unchecked 3
34592608 10.1016/j.ejmech.2021.113848 Structural capsid protein 3
38054267 10.1021/acs.jmedchem.3c01647 Human immunodeficiency virus 2 2
38054267 10.1021/acs.jmedchem.3c01647 MT4 2
34592608 10.1016/j.ejmech.2021.113848 MT4 1
38054267 10.1021/acs.jmedchem.3c01647 Unchecked 1
34592608 10.1016/j.ejmech.2021.113848 Unchecked 1
32298111 10.1021/acs.jmedchem.0c00015 MT4 1
32298111 10.1021/acs.jmedchem.0c00015 Human immunodeficiency virus type 1 reverse transcriptase 1
32298111 10.1021/acs.jmedchem.0c00015 TZM 1

Data from ChEMBL 36 via Core Engine