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CHEMBL238103

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COc1ncc(OC)c2c(C(=O)C(=O)N3CCN(C(=O)c4ccccc4)CC3)c[nH]c12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL238103
Phase Preclinical
Structure Type MOL
InChI Key DBPMWRYLTBNCCE-UHFFFAOYSA-N
5
Targets
37
Activities
3
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

422.4
MW (Da)
1.75
ALogP
6
HBA
1
HBD
104.8
PSA (Ų)
0.50
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H22N4O5
MW 422.44
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.78

Activity Summary

EC50 18 meas. best 9.12
IC50 17 meas. best 8.4
Kd 2 meas. best 7.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus 1
CHEMBL378
 EC50 9.12 8.2544 0.8 16
Unchecked
CHEMBL612545
 EC50 9.06 9.0 0.9 2
Human immunodeficiency virus
CHEMBL613758
 IC50 8.4 7.2718 4.0 11
Envelope glycoprotein gp160
CHEMBL1293311
 Kd 7.72 7.72 19.0 1
Unchecked
CHEMBL612545
 Kd 7.72 7.72 19.1 1
Unchecked
CHEMBL612545
 IC50 7.59 6.7567 25.8 3
Human immunodeficiency virus 1
CHEMBL378
 IC50 7.58 7.58 26.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.52 4.52 30000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6300.0 ng.hr.mL-1 Rattus norvegicus
AUC 21191.0 ng.hr.mL-1 Homo sapiens
AUC 2661.37 ng.hr.mL-1 Rattus norvegicus
AUC 2661.37 ng.hr.mL-1 Rattus norvegicus
AUC 18164.92 ng.hr.mL-1 Canis lupus familiaris
AUC 11828.32 ng.hr.mL-1 Macaca fascicularis
AUC 6336.6 ng.hr.mL-1 Rattus norvegicus
AUC 2661.37 ng.hr.mL-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 2.4 mL.min-1.kg-1 Canis lupus familiaris
CL 4.3 mL.min-1.kg-1 Macaca fascicularis
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 4497.68 nM Rattus norvegicus
Cmax 33000.0 nM Canis lupus familiaris
Cmax 9705.52 nM Homo sapiens
Cmax 1889.0 nM Rattus norvegicus
Cmax 1889.0 nM Rattus norvegicus
F 57.0 % Canis lupus familiaris
F 60.0 % Macaca mulatta
F 55.0 % Rattus norvegicus
F 90.0 % Rattus norvegicus
F 90.0 % Rattus norvegicus
F 90.0 % Rattus norvegicus
F 57.0 % Canis lupus familiaris
F 60.0 % Macaca fascicularis
F 90.0 % Rattus norvegicus
F 90.0 % Rattus norvegicus
F 57.0 % Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human immunodeficiency virus 1 EC50 = 0.75 nM 9.12 Antiviral activity against HIV1 JRFL infected in human HeLa cells expressing CD4... 23200252
Human immunodeficiency virus 1 EC50 = 0.8 nM 9.1 Antiviral activity against HIV1 JRFL infected in human HeLa67 cells after 3 days... 23360431
Unchecked EC50 = 0.88 nM 9.06 Inhibition of HIV1 JRFL gp120/CD4 interaction in human HeLa67 cells assessed as ... 19769332
Human immunodeficiency virus 1 EC50 = 0.88 nM 9.06 Antiviral activity against ENV pseudotyped CCR5-tropic HIV1 JFRL infected in hum... 29920093
Human immunodeficiency virus 1 EC50 = 0.88 nM 9.06 Antiviral activity against HIV-1 JRFL assessed as inhibition of viral growth 35477274
Unchecked EC50 = 1.15 nM 8.94 Inhibition of HIV1 LAI gp120/CD4 interaction in human HeLa67 cells assessed as i... 19769332
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against R5-tropic HIV1 JRFL infected in PM1 cells 23360431
Human immunodeficiency virus 1 EC50 = 3.0 nM 8.52 Antiviral activity against HIV-1 JR-FL infected in human PM1 cells harboring CCR... 29271653
Human immunodeficiency virus 1 EC50 = 3.44 nM 8.46 Antiviral activity against X4-tropic HIV1 LAI infected in MT2 cells 23360431
Human immunodeficiency virus IC50 = 4.0 nM 8.4 Antiviral activity against HIV isolate 584.000 220 by replication assay 19534463
Human immunodeficiency virus 1 EC50 = 4.1 nM 8.39 Antiviral activity against HIV-1 LAI infected in human MT2 cells harboring CXCR4... 29271653
Human immunodeficiency virus 1 EC50 = 4.7 nM 8.33 Antiviral activity against HIV-1 SF-162 infected in human PM1 cells harboring CC... 29271653
Human immunodeficiency virus 1 EC50 = 5.58 nM 8.25 Antiviral activity against X4-tropic HIV1 NL4-3 infected in MT2 cells 23360431
Human immunodeficiency virus 1 EC50 = 8.32 nM 8.08 Antiviral activity against X4-tropic HIV1 MN infected in MT2 cells 23360431
Human immunodeficiency virus IC50 = 11.0 nM 7.96 Antiviral activity against HIV isolate 584.000 066 by replication assay 19534463
Human immunodeficiency virus IC50 = 14.0 nM 7.85 Antiviral activity against HIV isolate 584.000 060 by replication assay 19534463
Human immunodeficiency virus IC50 = 17.0 nM 7.77 Antiviral activity against HIV isolate 584.000 063 by replication assay 19534463
Human immunodeficiency virus 1 EC50 = 17.4 nM 7.76 Antiviral activity against HIV-1 NL4 - 3 infected in human MT2 cells harboring C... 29271653
Envelope glycoprotein gp160 Kd = 19.0 nM 7.72 Inhibition of [3H]BMS-488043 binding to HIV-1 JRFL gp120 after 1 hr by scintilla... 29920093
Unchecked Kd = 19.1 nM 7.72 Inhibition of [3H]BMS-488043 binding to HIV-1 isolate JRFL gp120 after 60 mins b... 29271653

Literature References

PubMed DOI Target Context # Activities
19534463 10.1021/jm900330x Human immunodeficiency virus 12
29271653 10.1021/acs.jmedchem.7b01337 Human immunodeficiency virus 1 11
19769332 10.1021/jm900843g ADMET 10
19769332 10.1021/jm900843g No relevant target 8
29920093 10.1021/acs.jmedchem.8b00759 Human immunodeficiency virus 1 6
35477274 10.1021/acs.jmedchem.2c00444 ADMET 6
23360431 10.1021/jm3016377 Human immunodeficiency virus 1 6
22356441 10.1021/jm201218m No relevant target 5
19769332 10.1021/jm900843g Rattus norvegicus 5
22356441 10.1021/jm201218m Homo sapiens 5
29920093 10.1021/acs.jmedchem.8b00759 Rattus norvegicus 5
23360431 10.1021/jm3016377 Rattus norvegicus 5
29271653 10.1021/acs.jmedchem.7b01337 Unchecked 4
19769332 10.1021/jm900843g Canis familiaris 3
23206859 10.1016/j.bmcl.2012.10.118 Rattus norvegicus 3
29920093 10.1021/acs.jmedchem.8b00759 Canis familiaris 3
29920093 10.1021/acs.jmedchem.8b00759 Cynomolgus monkey 3
29920093 10.1021/acs.jmedchem.8b00759 ADMET 3
19769332 10.1021/jm900843g Unchecked 2
19769332 10.1021/jm900843g Cytochrome P450 3A4 2

Data from ChEMBL 36 via Core Engine