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Compound Detail

CHEMBL337301

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COc1ccnc2[nH]cc(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)C[C@H]3C)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL337301
Phase Preclinical
Structure Type MOL
InChI Key OKGPFTLYBPQBIX-CQSZACIVSA-N
5
Targets
47
Activities
2
Assay Types
19
PK Parameters
20
Publications
0
Known Names

Molecular Properties

406.4
MW (Da)
2.13
ALogP
5
HBA
1
HBD
95.6
PSA (Ų)
0.53
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22N4O4
MW 406.44
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -0.99

Activity Summary

IC50 33 meas. best 9.07
EC50 14 meas. best 9.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.07 8.05 0.8 9
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.07 8.054 0.8 5
Unchecked
CHEMBL612545
 EC50 8.83 8.3 1.5 5
Human immunodeficiency virus
CHEMBL613758
 IC50 8.4 7.0426 4.0 23
Unchecked
CHEMBL612545
 IC50 7.0 6.03 100.0 3
Envelope glycoprotein gp160
CHEMBL1293311
 IC50 5.06 5.06 8700.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.01 5.01 9700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 500.0 ng.hr.mL-1 Rattus norvegicus
AUC 528.37 ng.hr.mL-1 Rattus norvegicus
CL 32.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.2 mL.min-1.kg-1 Canis lupus familiaris
CL 10.0 mL.min-1.kg-1 Simiiformes
CL 32.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 220.0 nM Rattus norvegicus
Cmax 7400.0 nM Canis lupus familiaris
Cmax 510.0 nM Simiiformes
Cmax 221.43 nM Rattus norvegicus
F 19.0 % Rattus norvegicus
F 77.0 % Canis lupus familiaris
F 24.0 % Primates
F 77.0 % Canis lupus familiaris
F 24.0 % Macaca mulatta
F 19.0 % Rattus norvegicus
F 19.0 % Rattus norvegicus
T1/2 37.0 hr Homo sapiens
T1/2 0.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 IC50 = 0.85 nM 9.07 Antiviral activity against HIV1 19112024
Human immunodeficiency virus 1 EC50 = 0.85 nM 9.07 Inhibitory activity of compound against TLAV (dual) virus that utilizes both CXR... 13678401
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 JR-FL in human HeLa cells expressing CD4, CCR5 a... 23200254
Human immunodeficiency virus 1 EC50 = 1.47 nM 8.83 Inhibitory activity of compound against JRFL (M) Macrophage tropic virus that ut... 13678401
Unchecked EC50 = 1.47 nM 8.83 Inhibition of HIV1 JRFL gp120/CD4 interaction in human HeLa67 cells assessed as ... 19769332
Human immunodeficiency virus 1 EC50 = 1.47 nM 8.83 Antiviral activity against HIV1 26116177
Unchecked EC50 = 2.68 nM 8.57 Inhibitory activity of compound against LAI (T) tropic virus that utilizes the C... 13678401
Unchecked EC50 = 2.68 nM 8.57 Inhibition of HIV1 LAI gp120/CD4 interaction in human HeLa67 cells assessed as i... 19769332
Unchecked EC50 = 2.94 nM 8.53 Inhibitory activity of compound against NL4-3 (T) tropic virus that utilizes the... 13678401
Human immunodeficiency virus 1 EC50 = 3.46 nM 8.46 Inhibitory activity of compound against SF-162 (M) Macrophage tropic virus that ... 13678401
Human immunodeficiency virus IC50 = 4.0 nM 8.4 Antiviral activity against HIV 584.000220 by viral replication assay 18052117
Human immunodeficiency virus IC50 = 5.0 nM 8.3 Antiviral activity against HIV isolate 584.000 220 by replication assay 19534463
Human immunodeficiency virus IC50 = 6.0 nM 8.22 Antiviral activity against HIV 589.000049 by viral replication assay 18052117
Human immunodeficiency virus 1 IC50 = 8.0 nM 8.1 Antiviral activity against HIV1 pseudovirus in U87 cells expressing CD4 and CCR5... 18052117
Human immunodeficiency virus 1 IC50 = 8.0 nM 8.1 Antiviral activity against HIV1 expressed in 293T cells assessed as protection a... 19534463
Human immunodeficiency virus IC50 = 14.0 nM 7.85 Antiviral activity against HIV 584.000088 by viral replication assay 18052117
Human immunodeficiency virus 1 EC50 = 15.5 nM 7.81 Inhibitory activity of compound against BAl (M) Macrophage tropic virus that uti... 13678401
Human immunodeficiency virus IC50 = 24.0 nM 7.62 Antiviral activity against HIV isolate 584.000 060 by replication assay 19534463
Human immunodeficiency virus 1 EC50 = 26.5 nM 7.58 Inhibitory activity of compound against SF-2 (T) tropic virus that utilizes the ... 13678401
Human immunodeficiency virus IC50 = 27.0 nM 7.57 Antiviral activity against HIV isolate 589.000 033 by replication assay 19534463

Literature References

PubMed DOI Target Context # Activities
18052117 10.1021/jm070650e Human immunodeficiency virus 12
19534463 10.1021/jm900330x Human immunodeficiency virus 12
13678401 10.1021/jm034082o Human immunodeficiency virus 1 7
13678401 10.1021/jm034082o ADMET 6
19769332 10.1021/jm900843g No relevant target 4
19769332 10.1021/jm900843g Rattus norvegicus 4
13678401 10.1021/jm034082o Rattus norvegicus 3
13678401 10.1021/jm034082o Canis familiaris 3
23200254 10.1016/j.bmcl.2012.10.120 Rattus norvegicus 3
26985308 10.1021/acsmedchemlett.5b00339 Unchecked 3
19769332 10.1021/jm900843g Cytochrome P450 3A4 2
13678401 10.1021/jm034082o Unchecked 2
29271653 10.1021/acs.jmedchem.7b01337 No relevant target 2
19769332 10.1021/jm900843g Unchecked 2
17954689 10.1128/aac.00737-07 Envelope glycoprotein gp160 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
28266845 10.1021/acs.jmedchem.7b00179 Human immunodeficiency virus 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
34992041 10.1016/j.ejmech.2021.114078 Human immunodeficiency virus 1 1

Data from ChEMBL 36 via Core Engine