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Compound Detail

CHEMBL599883

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COc1nncc(-c2cnnc(SC)n2)n1

Basic Information

ChEMBL ID CHEMBL599883
Phase Preclinical
Structure Type MOL
InChI Key NAHCQBYVFUTQPQ-UHFFFAOYSA-N
8
Targets
20
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

236.3
MW (Da)
0.45
ALogP
8
HBA
0
HBD
86.6
PSA (Ų)
0.71
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 C8H8N6OS
MW 236.26
Aromatic Rings 2
Heavy Atoms 16
NP-Likeness -1.50

Activity Summary

EC50 13 meas. best 6.82
IC50 7 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
EC50 6.82 6.692 150.0 5
Plasmodium falciparum
CHEMBL364
IC50 6.82 6.76 150.0 2
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 5.3 5.3 5000.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
EC50 5.24 5.24 5700.0 2
Leishmania donovani
CHEMBL367
IC50 5.1 5.1 8000.0 1
Leishmania infantum
CHEMBL612848
EC50 5.07 5.07 8600.0 2
Trypanosoma cruzi
CHEMBL368
IC50 4.82 4.82 15000.0 1
Trypanosoma cruzi
CHEMBL368
EC50 4.8 4.8 16000.0 2
HEK293
CHEMBL614818
EC50 4.75 4.75 18000.0 1
Trypanothione reductase
CHEMBL5131
IC50 4.57 4.57 27000.0 1
L6
CHEMBL614793
EC50 4.48 4.48 33000.0 1
L6
CHEMBL614793
IC50 4.48 4.48 33000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 150.0 nM 6.82 Antimalarial activity against Plasmodium falciparum 3D7 infected in human erythr... 20822904
Plasmodium falciparum IC50 = 150.0 nM 6.82 Antimalarial activity against Plasmodium falciparum 3D7 infected HEK293 cells by... 30715882
Plasmodium falciparum EC50 = 180.0 nM 6.75 Antimalarial activity against erythrocytic stage of Plasmodium falciparum 3D7 20584608
Plasmodium falciparum IC50 = 200.0 nM 6.7 Antiplasmodial activity against Plasmodium falciparum 3D7 erythrocytic stage 19364854
Plasmodium falciparum EC50 = 219.1 nM 6.66 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Plasmodium falciparum EC50 = 236.6 nM 6.63 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum EC50 = 250.0 nM 6.6 Antimalarial activity against Plasmodium falciparum Dd2 infected in human erythr... 20822904
Trypanosoma brucei rhodesiense IC50 = 5000.0 nM 5.3 Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB900 bloodst... 19364854
Trypanosoma brucei rhodesiense EC50 = 5700.0 nM 5.24 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei rhodesi... 20584608
Trypanosoma brucei rhodesiense EC50 = 5700.0 nM 5.24 Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB 900 20822904
Leishmania donovani IC50 = 8000.0 nM 5.1 Antiprotozoal activity against Leishmania donovani MHOM/ET/67/L82 amastigotes 19364854
Leishmania infantum EC50 = 8600.0 nM 5.07 Antileishmanial activity against amastigote stage of Leishmania infantum 20584608
Leishmania infantum EC50 = 8600.0 nM 5.07 Antileishmanial activity against Leishmania infantum 20822904
Trypanosoma cruzi IC50 = 15000.0 nM 4.82 Antiprotozoal activity against Trypanosoma cruzi Tulahuen C2C4 amastigotes 19364854
Trypanosoma cruzi EC50 = 16000.0 nM 4.8 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen C2C4 20822904
Trypanosoma cruzi EC50 = 16000.0 nM 4.8 Antitrypanosomal activity against amastigote stage of Trypanosoma cruzi Tulahuen... 20584608
HEK293 EC50 = 18000.0 nM 4.75 Cytotoxicity against HEK293 cells 20822904
Trypanothione reductase IC50 = 27000.0 nM 4.57 Inhibition of Trypanosoma cruzi X10/1 trypanothione reductase assessed as inhibi... 19364854
L6 EC50 = 33000.0 nM 4.48 Cytotoxicity against rat L6 cells 20822904
L6 IC50 = 33000.0 nM 4.48 Cytotoxicity against rat L6 cells 20584608

Literature References

PubMed DOI Target Context # Activities
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
20822904 10.1016/j.bmcl.2010.08.065 Plasmodium falciparum 2
20822904 10.1016/j.bmcl.2010.08.065 Leishmania infantum 1
30715882 10.1021/acs.jmedchem.8b01799 Plasmodium falciparum 1
19364854 10.1128/aac.01568-08 L6 1
19364854 10.1128/aac.01568-08 Trypanosoma brucei rhodesiense 1
19364854 10.1128/aac.01568-08 Trypanosoma cruzi 1
19364854 10.1128/aac.01568-08 Leishmania donovani 1
19364854 10.1128/aac.01568-08 Plasmodium falciparum 1
19364854 10.1128/aac.01568-08 Trypanothione reductase 1
20822904 10.1016/j.bmcl.2010.08.065 L6 1
20822904 10.1016/j.bmcl.2010.08.065 Trypanosoma brucei rhodesiense 1
20822904 10.1016/j.bmcl.2010.08.065 Trypanosoma cruzi 1
18579783 10.1073/pnas.0802982105 Unchecked 1
20822904 10.1016/j.bmcl.2010.08.065 HEK293 1
20584608 10.1016/j.bmcl.2010.06.036 L6 1
20584608 10.1016/j.bmcl.2010.06.036 Trypanosoma brucei rhodesiense 1
20584608 10.1016/j.bmcl.2010.06.036 Trypanosoma cruzi 1
20584608 10.1016/j.bmcl.2010.06.036 Leishmania infantum 1
20584608 10.1016/j.bmcl.2010.06.036 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine