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CHEMBL489586

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N#Cc1cc(Cl)cc(Oc2cc(OCc3n[nH]c4nc(N)ccc34)ccc2Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL489586
Phase Preclinical
Structure Type MOL
InChI Key KXDIHAQCVNNLIB-UHFFFAOYSA-N
4
Targets
50
Activities
2
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

426.3
MW (Da)
5.09
ALogP
6
HBA
2
HBD
109.8
PSA (Ų)
0.46
QED
1
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 C20H13Cl2N5O2
MW 426.26
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -1.27

Activity Summary

IC50 42 meas. best 9.7
Ki 8 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 IC50 9.7 8.9878 0.2 9
Unchecked
CHEMBL612545
 Ki 9.7 9.7 0.2 3
Human immunodeficiency virus type 1 reverse transcriptase
CHEMBL247
 Ki 9.41 9.408 0.4 5
Human immunodeficiency virus 1
CHEMBL378
 IC50 9.15 8.1588 0.7 17
Human immunodeficiency virus
CHEMBL613758
 IC50 8.89 7.9475 1.3 16

Pharmacokinetic Data

Parameter Value Units Species
AUC 9676.1 ng.hr.mL-1 Rattus norvegicus
AUC 13341.94 ng.hr.mL-1 Canis lupus familiaris
AUC 127.88 ng.hr.mL-1 Macaca mulatta
AUC 23.0 uM Rattus norvegicus
AUC 0.3 uM Macaca mulatta
AUC 31.0 uM Canis lupus familiaris
CL 9.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.8 mL.min-1.kg-1 Canis lupus familiaris
CL 15.8 mL.min-1.kg-1 Macaca mulatta
CL 5.8 mL.min-1.kg-1 Canis lupus familiaris
CL 9.0 mL.min-1.kg-1 Rattus norvegicus
CL 16.0 mL.min-1.kg-1 Macaca mulatta
CL 9.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.8 mL.min-1.kg-1 Canis lupus familiaris
CL 9.0 mL.min-1.kg-1 Rattus norvegicus
F 52.0 % Rattus norvegicus
F 47.0 % Canis lupus familiaris
F 1.0 % Macaca mulatta
F 1.0 % Macaca mulatta
F 47.0 % Canis lupus familiaris
F 52.0 % Rattus norvegicus
F 52.0 % Rattus norvegicus
F 47.0 % Canis lupus familiaris
T1/2 3.5 hr Rattus norvegicus
T1/2 3.9 hr Canis lupus familiaris
T1/2 2.1 hr Macaca mulatta
T1/2 2.1 hr Macaca mulatta
T1/2 3.5 hr Rattus norvegicus
T1/2 3.9 hr Canis lupus familiaris
T1/2 3.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.2 nM 9.7 Inhibition of RNA-dependent DNA polymerase activity of wild type HIV reverse tra... 19883100
Unchecked Ki = 0.2 nM 9.7 Inhibition of Human immunodeficiency virus wild type reverse transcriptase by SP... 22071300
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 0.2 nM 9.7 Inhibition of wild type HIV1 RT polymerase by SPA 18826204
Unchecked Ki = 0.2 nM 9.7 Inhibition of Human immunodeficiency virus reverse transcriptase by SPA assay 21985673
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 0.23 nM 9.64 Inhibition of HIV1 isolate R8 reverse transcriptase after 90 mins 19289522
Human immunodeficiency virus type 1 reverse transcriptase Ki = 0.39 nM 9.41 Inhibition of Human immunodeficiency virus reverse transcriptase Y181C mutant by... 21985673
Human immunodeficiency virus type 1 reverse transcriptase Ki = 0.39 nM 9.41 Inhibition of Human immunodeficiency virus reverse transcriptase Y181C mutant by... 22071300
Human immunodeficiency virus type 1 reverse transcriptase Ki = 0.39 nM 9.41 Inhibition of Human immunodeficiency virus reverse transcriptase K103N mutant by... 22071300
Human immunodeficiency virus type 1 reverse transcriptase Ki = 0.39 nM 9.41 Inhibition of Human immunodeficiency virus reverse transcriptase K103N mutant by... 21985673
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 0.39 nM 9.41 Inhibition of HIV1 isolate R8 reverse transcriptase Y181C mutant after 90 mins b... 19289522
Human immunodeficiency virus type 1 reverse transcriptase Ki = 0.4 nM 9.4 Inhibition of RNA-dependent DNA polymerase activity of recombinant HIV reverse t... 19883100
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 0.4 nM 9.4 Inhibition of HIV1 RT polymerase Y181C mutant by SPA 18826204
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 0.4 nM 9.4 Inhibition of HIV1 isolate R8 reverse transcriptase K103N mutant after 90 mins b... 19289522
Human immunodeficiency virus type 1 reverse transcriptase IC50 = 0.5 nM 9.3 Inhibition of HIV1 RT polymerase K103N mutant by SPA 18826204
Human immunodeficiency virus 1 IC50 = 0.7 nM 9.15 Antiviral activity against HIV1 with reverse transcriptase F227L mutant in prese... 18826204
Human immunodeficiency virus 1 IC50 = 1.2 nM 8.92 Antiviral activity against HIV1 with reverse transcriptase K103N/P225H mutant in... 18826204
Human immunodeficiency virus IC50 = 1.3 nM 8.89 Antiviral activity against HIV with reverse transcriptase L100I mutant assessed ... 19883100
Human immunodeficiency virus 1 IC50 = 1.35 nM 8.87 Antiviral activity against wild type HIV1 in presence of 40% normal human serum 18826204
Human immunodeficiency virus IC50 = 1.4 nM 8.85 Antiviral activity against HIV with reverse transcriptase CNDO mutant assessed a... 19883100
Human immunodeficiency virus 1 IC50 = 1.5 nM 8.82 Antiviral activity against HIV1 with reverse transcriptase G190A mutant in prese... 18826204

Literature References

PubMed DOI Target Context # Activities
19883100 10.1021/jm901230r Human immunodeficiency virus 39
19289522 10.1128/aac.01559-08 Human immunodeficiency virus 1 32
18826204 10.1021/jm800856c Human immunodeficiency virus 1 22
21985673 10.1021/jm2010173 Human immunodeficiency virus 18
22071300 10.1016/j.bmcl.2011.10.027 Human immunodeficiency virus 8
18826204 10.1021/jm800856c Canis familiaris 8
19289522 10.1128/aac.01559-08 ADMET 7
19883100 10.1021/jm901230r Canis familiaris 5
21985673 10.1021/jm2010173 Canis familiaris 5
21985673 10.1021/jm2010173 Rattus norvegicus 5
19883100 10.1021/jm901230r Rhesus monkey 5
19883100 10.1021/jm901230r Rattus norvegicus 5
18826204 10.1021/jm800856c Rhesus monkey 5
18826204 10.1021/jm800856c Rattus norvegicus 5
24900529 10.1021/ml300146q Human immunodeficiency virus type 1 reverse transcriptase 4
18826204 10.1021/jm800856c Human immunodeficiency virus type 1 reverse transcriptase 3
19289522 10.1128/aac.01559-08 Human immunodeficiency virus type 1 reverse transcriptase 3
22071300 10.1016/j.bmcl.2011.10.027 Rattus norvegicus 3
22071300 10.1016/j.bmcl.2011.10.027 MT4 2
19289522 10.1128/aac.01559-08 Unchecked 2

Data from ChEMBL 36 via Core Engine