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Compound Detail

CHEMBL6741

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CC1(C)N=C(N)N=C(N)N1c1ccc(Br)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL6741
Phase Preclinical
Structure Type MOL
InChI Key LLRTYNPSGQWCLZ-UHFFFAOYSA-N
8
Targets
14
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

296.2
MW (Da)
1.63
ALogP
5
HBA
2
HBD
80.0
PSA (Ų)
0.83
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C11H14BrN5
MW 296.17
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -0.45

Activity Summary

EC50 7 meas. best 6.8
Ki 5 meas. best 8.96
IC50 2 meas. best 7.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.96 7.8633 1.1 3
Plasmodium falciparum
CHEMBL364
 IC50 7.51 6.535 31.0 2
Dihydrofolate reductase
CHEMBL2575
 Ki 7.12 7.12 75.9 1
Respiratory syncytial virus
CHEMBL612679
 EC50 6.8 6.8 160.0 1
Unchecked
CHEMBL612545
 EC50 6.0 5.0433 1000.0 3
Influenza B virus
CHEMBL613129
 EC50 5.54 5.54 2900.0 1
Influenza A virus
CHEMBL613740
 EC50 5.14 4.91 7300.0 2
Dihydrofolate reductase
CHEMBL2902
 Ki 4.57 4.57 26915.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.1 nM 8.96 Evaluated for inhibition constant (Ki wt) against Wild-type dihydrofolate reduct... 10893311
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.2 nM 8.92 Inhibition constant against Plasmodium falciparum dihydrofolate reductase 15293997
Plasmodium falciparum IC50 = 31.0 nM 7.51 Growth inhibition (IC50) against Plasmodium falciparum wild-type TM4/8.2 10893311
Dihydrofolate reductase Ki = 75.86 nM 7.12 Inhibitory activity against isolated chicken liver dihydrofolate reductase (DHFR... 6420569
Respiratory syncytial virus EC50 = 160.0 nM 6.8 Antiviral activity against Respiratory syncytial virus infected in human HeLa ce... 28477572
Unchecked EC50 = 1000.0 nM 6.0 Antiviral activity against Influenza B virus B/Ned/537/05 infected in MDCK cells... 28477572
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1947.0 nM 5.71 Inhibition constant (Ki mut) against A16V+S108T Mutant DHFRs of Plasmodium falci... 10893311
Plasmodium falciparum IC50 = 2759.0 nM 5.56 Inhibition of Plasmodium falciparum T9/94 mutant 10893311
Influenza B virus EC50 = 2900.0 nM 5.54 Antiviral activity against Influenza B virus B/Ned/537/05 infected in MDCK cells... 28477572
Influenza A virus EC50 = 7300.0 nM 5.14 Antiviral activity against Influenza A virus A/Ned/378/05(H1N1) infected in MDCK... 28477572
Unchecked EC50 = 19000.0 nM 4.72 Antiviral activity against Influenza A virus A/Virginia/ATCC3/2009(H1N1) infecte... 28477572
Influenza A virus EC50 = 21000.0 nM 4.68 Antiviral activity against Influenza A virus A/Ned/378/05(H1N1) infected in MDCK... 28477572
Dihydrofolate reductase Ki = 26915.35 nM 4.57 Inhibitory activity against Lactobacillus casei dihydrofolate reductase (DHFR) 6420569
Unchecked EC50 = 39000.0 nM 4.41 Antiviral activity against Influenza A virus A/Virginia/ATCC3/2009(H1N1) infecte... 28477572

Literature References

PubMed DOI Target Context # Activities
10893311 10.1021/jm0009181 Bifunctional dihydrofolate reductase-thymidylate synthase 6
28477572 10.1016/j.ejmech.2017.04.070 Unchecked 3
28477572 10.1016/j.ejmech.2017.04.070 Influenza A virus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
28477572 10.1016/j.ejmech.2017.04.070 Coxsackievirus B4 2
28477572 10.1016/j.ejmech.2017.04.070 MDCK 2
6420569 10.1021/jm00368a006 Dihydrofolate reductase 2
6699880 10.1021/jm00369a019 Dihydrofolate reductase 2
10893311 10.1021/jm0009181 Plasmodium falciparum 2
7241512 10.1021/jm00137a013 Dihydrofolate reductase 2
15293997 10.1021/jm040769c Bifunctional dihydrofolate reductase-thymidylate synthase 1
6694162 10.1021/jm00368a007 Dihydrofolate reductase 1
28477572 10.1016/j.ejmech.2017.04.070 Influenza B virus 1
28477572 10.1016/j.ejmech.2017.04.070 Vesicular stomatitis virus 1
6864738 10.1021/jm00361a012 Dihydrofolate reductase 1
28477572 10.1016/j.ejmech.2017.04.070 HeLa 1
28477572 10.1016/j.ejmech.2017.04.070 Human respirovirus 3 1
28477572 10.1016/j.ejmech.2017.04.070 Mammalian orthoreovirus 1 1
28477572 10.1016/j.ejmech.2017.04.070 Sindbis virus 1
28477572 10.1016/j.ejmech.2017.04.070 Punta Toro virus 1

Data from ChEMBL 36 via Core Engine