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CHEMBL135339

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O=C(C(=O)N1CCN(C(=O)c2ccccc2)CC1)c1c[nH]c2cccc(F)c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL135339
Phase Preclinical
Structure Type MOL
InChI Key XTGGYFJUBIZBKW-UHFFFAOYSA-N
4
Targets
23
Activities
1
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

379.4
MW (Da)
2.47
ALogP
3
HBA
1
HBD
73.5
PSA (Ų)
0.56
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H18FN3O3
MW 379.39
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -1.16

Activity Summary

EC50 23 meas. best 8.91

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 8.91 7.2794 1.2 17
Unchecked
CHEMBL612545
 EC50 8.59 8.305 2.6 4
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.05 7.05 90.0 1
Human immunodeficiency virus 2
CHEMBL380
 EC50 6.07 6.07 850.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 48.0 mL.min-1.kg-1 Rattus norvegicus
CL 2.4 mL.min-1.kg-1 Canis lupus familiaris
CL 3.1 mL.min-1.kg-1 Simiiformes
CL 48.0 mL.min-1.kg-1 Rattus norvegicus
CL 48.0 mL.min-1.kg-1 Rattus norvegicus
CL 48.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 150.0 nM Rattus norvegicus
Cmax 18000.0 nM Canis lupus familiaris
Cmax 34000.0 nM Simiiformes
Cmax 1710.64 nM Rattus norvegicus
Cmax 150.24 nM Rattus norvegicus
Cmax 47.44 nM Rattus norvegicus
Cmax 1476.05 nM Canis lupus familiaris
Cmax 158.15 nM Canis lupus familiaris
Cmax 421.73 nM Canis lupus familiaris
Cmax 1710.64 nM Rattus norvegicus
Cmax 150.24 nM Rattus norvegicus
F 9.4 % Rattus norvegicus
F 100.0 % Canis lupus familiaris
F 100.0 % Primates
F 17.0 % Rattus norvegicus
F 9.0 % Rattus norvegicus
F 4.0 % Rattus norvegicus
F 89.0 % Canis lupus familiaris
F 12.0 % Canis lupus familiaris
F 36.0 % Canis lupus familiaris
F 17.0 % Rattus norvegicus
F 9.0 % Rattus norvegicus
F 9.0 % Rattus norvegicus
F 100.0 % Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 1.24 nM 8.91 Antiviral activity against HIV1 JRFL infected in human HeLa cells expressing CD4... 23200252
Human immunodeficiency virus 1 EC50 = 1.24 nM 8.91 Antiviral activity against HIV1 JRFL pseudotyped virions infected in HeLa CD4 CC... 23200244
Human immunodeficiency virus 1 EC50 = 1.24 nM 8.91 Antiviral activity against HIV1 JRFL pseudotyped virus infected in HeLa CD4+ CCR... 23200249
Human immunodeficiency virus 1 EC50 = 2.39 nM 8.62 Inhibitory activity of compound in MT-2 cells against JRFL (M) Macrophage tropic... 13678401
Human immunodeficiency virus 1 EC50 = 2.59 nM 8.59 Antiviral activity against pseudotype HIV1 JRFL infected in human HeLa67 cells e... 19251416
Human immunodeficiency virus 1 EC50 = 2.6 nM 8.59 Antiviral activity against HIV1 infected human HeLa67 cells coexpressing JRFL-LU... 19632112
Unchecked EC50 = 2.59 nM 8.59 Inhibition of HIV1 gp120 binding to CD4 in human HeLa cells by cell fusion assay 20149491
Unchecked EC50 = 2.57 nM 8.59 Inhibition of HIV1 gp120 binding to CD4 in human HeLa cells by cell fusion assay 20149491
Unchecked EC50 = 2.93 nM 8.53 Inhibitory activity of compound against LAI (T) tropic virus that utilizes the C... 13678401
Human immunodeficiency virus 1 EC50 = 13.6 nM 7.87 Inhibitory activity of compound against TLAV (dual) virus that utilizes both CXR... 13678401
Human immunodeficiency virus 1 EC50 = 18.1 nM 7.74 Inhibitory activity of compound against BAl (M) Macrophage tropic virus that uti... 13678401
Unchecked EC50 = 30.8 nM 7.51 Inhibitory activity of compound against NL4-3 (T) tropic virus that utilizes the... 13678401
Human immunodeficiency virus 1 EC50 = 62.4 nM 7.21 Inhibitory activity of compound against SF-2 (T) tropic virus that utilizes the ... 13678401
NON-PROTEIN TARGET EC50 = 90.0 nM 7.05 Antiviral activity against T-tropic HIV1 BRU virus by cell culture based assay 23200249
Human immunodeficiency virus 1 EC50 = 700.0 nM 6.16 Antiviral activity against M-tropic HIV1 Bal virus by cell culture based assay 23200249
Human immunodeficiency virus 1 EC50 = 850.0 nM 6.07 Antiviral activity against HIV1 TLAV 26116177
Human immunodeficiency virus 1 EC50 = 850.0 nM 6.07 Antiviral activity against HIV1 JRFL 26116177
Human immunodeficiency virus 1 EC50 = 850.0 nM 6.07 Antiviral activity against HIV1 SF162 26116177
Human immunodeficiency virus 1 EC50 = 850.0 nM 6.07 Antiviral activity against HIV1 BAL 26116177
Human immunodeficiency virus 1 EC50 = 850.0 nM 6.07 Antiviral activity against HIV1 NL4-3 26116177

Literature References

PubMed DOI Target Context # Activities
19251416 10.1016/j.bmcl.2009.02.040 Rattus norvegicus 14
19251416 10.1016/j.bmcl.2009.02.040 Canis familiaris 9
13678401 10.1021/jm034082o Human immunodeficiency virus 1 7
13678401 10.1021/jm034082o ADMET 6
26116177 10.1016/j.bmc.2015.06.016 Human immunodeficiency virus 1 6
23200249 10.1016/j.bmcl.2012.10.117 Rattus norvegicus 4
23200249 10.1016/j.bmcl.2012.10.117 Human immunodeficiency virus 1 3
23200252 10.1016/j.bmcl.2012.10.115 Rattus norvegicus 3
13678401 10.1021/jm034082o Canis familiaris 3
13678401 10.1021/jm034082o Rattus norvegicus 3
29271653 10.1021/acs.jmedchem.7b01337 Canis familiaris 2
29271653 10.1021/acs.jmedchem.7b01337 No relevant target 2
19251416 10.1016/j.bmcl.2009.02.040 No relevant target 2
19664921 10.1016/j.bmcl.2009.07.076 Liver microsomes 2
29271653 10.1021/acs.jmedchem.7b01337 Rattus norvegicus 2
20149491 10.1016/j.ejmech.2010.01.011 Unchecked 2
23200252 10.1016/j.bmcl.2012.10.115 No relevant target 2
13678401 10.1021/jm034082o Unchecked 2
19251416 10.1016/j.bmcl.2009.02.040 Caco-2 1
19664921 10.1016/j.bmcl.2009.07.076 Caco-2 1

Data from ChEMBL 36 via Core Engine