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Compound Detail

CHEMBL598279

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COc1ccc(Nc2nc(NCc3ccccc3)c3ccccc3n2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL598279
Phase Preclinical
Structure Type MOL
InChI Key GFDLOQVUVBBATG-UHFFFAOYSA-N
16
Targets
27
Activities
2
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

356.4
MW (Da)
4.99
ALogP
5
HBA
2
HBD
59.1
PSA (Ų)
0.51
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H20N4O
MW 356.43
Aromatic Rings 4
Heavy Atoms 27
NP-Likeness -1.26

Activity Summary

IC50 20 meas. best 7.22
EC50 7 meas. best 6.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 7.22 5.91 60.0 4
Plasmodium falciparum
CHEMBL364
 IC50 7.04 6.865 90.6 2
Plasmodium falciparum
CHEMBL364
 EC50 6.97 6.6125 106.5 4
Plasmodium yoelii
CHEMBL612889
 IC50 6.51 6.51 305.4 1
Trypanosoma cruzi
CHEMBL368
 EC50 6.3 6.3 500.0 1
Schistosoma mansoni
CHEMBL612893
 IC50 6.1 5.835 800.0 2
Leishmania infantum
CHEMBL612848
 IC50 6.0 6.0 1007.0 1
Trypanosoma cruzi
CHEMBL368
 IC50 5.45 5.45 3551.8 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 5.42 5.42 3836.4 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.39 5.39 4028.1 1
Solute carrier family 2, facilitated glucose transporter member 1
CHEMBL2535
 IC50 5.35 5.35 4477.0 1
Hexose transporter 1
CHEMBL4697
 IC50 5.33 5.33 4674.0 1
Glucose transporter
CHEMBL3431938
 IC50 5.31 5.31 4890.0 1
HepG2
CHEMBL395
 EC50 5.07 5.07 8500.0 1
MRC5
CHEMBL614181
 IC50 4.91 4.91 12381.7 1
HT-29
CHEMBL384
 IC50 4.87 4.87 13400.0 1
Trypanosoma brucei brucei
CHEMBL612851
 EC50 4.82 4.82 15100.0 1
DU-145
CHEMBL613508
 IC50 4.67 4.67 21300.0 1
Cruzipain
CHEMBL3563
 IC50 4.28 4.28 52000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 27.0 mL.min-1.g-1 Homo sapiens
CL 123.0 mL.min-1.g-1 Mus musculus
T1/2 1.083 hr Homo sapiens
T1/2 0.2333 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 60.0 nM 7.22 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Plasmodium falciparum IC50 = 90.59 nM 7.04 MMV: IC50 determined against P. falciparum Dd2-luc strain using a Malaria Sybr G... -
Plasmodium falciparum EC50 = 106.5 nM 6.97 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Plasmodium falciparum IC50 = 204.44 nM 6.69 MMV: Growth inhibition of P. falciparum cultures was quantified using a parasite... -
Plasmodium falciparum EC50 = 212.5 nM 6.67 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum EC50 = 264.0 nM 6.58 Antimalarial activity against Plasmodium falciparum 3D7 asexual blood stage infe... 28080063
Plasmodium yoelii IC50 = 305.4 nM 6.51 NOVARTIS: Antimalarial liver stage activity measured as reduction in Plasmodium ... 22096101
Trypanosoma cruzi EC50 = 500.0 nM 6.3 Trypanocidal activity against amastigotes form of Trypanosoma cruzi CA-I/72 infe... 34461718
Plasmodium falciparum EC50 = 589.0 nM 6.23 MMV: Inhibition of Plasmodium falciparum 3D7 (EC50). -
Schistosoma mansoni IC50 = 800.0 nM 6.1 Antischistosomal activity against Schistosoma mansoni Puerto-Rican incubated for... 33479649
Leishmania infantum IC50 = 1007.03 nM 6.0 MMV: Inhibition of Leishmania infantum (MHOM/MA/BE/67) in vitro. -
Unchecked IC50 = 2160.0 nM 5.67 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Schistosoma mansoni IC50 = 2700.0 nM 5.57 Antischistosomal activity against Schistosoma mansoni Liberian NTS incubated for... 33479649
Trypanosoma cruzi IC50 = 3551.85 nM 5.45 MMV: Inhibition of Trypanosoma cruzi (Tulahuen C4 LacZ) (Chagas in vitro). -
Unchecked IC50 = 3700.0 nM 5.43 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Trypanosoma brucei brucei IC50 = 3836.42 nM 5.42 MMV: Inhibition of Trypanosoma brucei brucei (Squib 427) (HAT in vitro). -
Trypanosoma brucei rhodesiense IC50 = 4028.1 nM 5.39 MMV: Inhibition of Trypanosoma brucei rhodesiense (STIB 900) (HAT in vitro). -
Solute carrier family 2, facilitated glucose transporter member 1 IC50 = 4477.0 nM 5.35 ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes... -
Hexose transporter 1 IC50 = 4674.0 nM 5.33 ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes... -
Unchecked IC50 = 4770.0 nM 5.32 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL2363022 Schistosoma mansoni 9
- 10.6019/CHEMBL3301486 Unchecked 8
- 10.6019/CHEMBL3301472 Human immunodeficiency virus 1 7
34461718 10.1021/acs.jmedchem.1c01151 Cruzipain 7
- 10.6019/CHEMBL3301472 NON-PROTEIN TARGET 6
28080063 10.1021/acs.jmedchem.6b01673 Liver 6
- 10.6019/CHEMBL3137381 Onchocerca lienalis 4
- 10.6019/CHEMBL2094260 Mycobacterium tuberculosis 4
- 10.6019/CHEMBL3301464 Unchecked 4
22096101 10.1126/science.1211936 Plasmodium yoelii 3
34461718 10.1021/acs.jmedchem.1c01151 Rhodesain 3
21306907 10.1016/j.bmc.2011.01.023 HT-29 3
33479649 10.1039/D0MD00062K Schistosoma mansoni 3
- 10.6019/CHEMBL3301546 Saccharomyces cerevisiae 3
21306907 10.1016/j.bmc.2011.01.023 DU-145 2
21306907 10.1016/j.bmc.2011.01.023 SK-MEL-2 2
28080063 10.1021/acs.jmedchem.6b01673 No relevant target 2
- 10.6019/CHEMBL3301458 Voltage-gated inwardly rectifying potassium channel KCNH2 2
20485428 10.1038/nature09099 Plasmodium falciparum 2
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2

Data from ChEMBL 36 via Core Engine