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Compound Detail

CHEMBL585966

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COc1cc(C(=O)ON=C(N)Cc2cccc3ccccc23)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL585966
Phase Preclinical
Structure Type MOL
InChI Key ADZFTCMTEDATTQ-UHFFFAOYSA-N
6
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

394.4
MW (Da)
3.54
ALogP
6
HBA
1
HBD
92.4
PSA (Ų)
0.29
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22N2O5
MW 394.43
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.55

Activity Summary

IC50 10 meas. best 5.94
EC50 4 meas. best 6.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 EC50 6.77 6.425 171.1 4
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.94 5.94 1152.5 1
Trypanosoma cruzi
CHEMBL368
 IC50 5.58 5.58 2621.2 1
Plasmodium falciparum
CHEMBL364
 IC50 5.4 5.395 3945.0 2
Trypanosoma brucei brucei
CHEMBL612851
 IC50 5.39 5.39 4086.7 1
Unchecked
CHEMBL612545
 IC50 5.28 5.015 5300.0 4
MRC5
CHEMBL614181
 IC50 5.25 5.25 5656.9 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum EC50 = 171.1 nM 6.77 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Plasmodium falciparum EC50 = 279.6 nM 6.55 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum EC50 = 540.0 nM 6.27 MMV: Inhibition of Plasmodium falciparum K1 (EC50). -
Plasmodium falciparum EC50 = 782.0 nM 6.11 MMV: Inhibition of Plasmodium falciparum 3D7 (EC50). -
Trypanosoma brucei rhodesiense IC50 = 1152.54 nM 5.94 MMV: Inhibition of Trypanosoma brucei rhodesiense (STIB 900) (HAT in vitro). -
Trypanosoma cruzi IC50 = 2621.23 nM 5.58 MMV: Inhibition of Trypanosoma cruzi (Tulahuen C4 LacZ) (Chagas in vitro). -
Plasmodium falciparum IC50 = 3945.0 nM 5.4 MMV: IC50 determined against P. falciparum Dd2-luc strain using a Malaria Sybr G... -
Trypanosoma brucei brucei IC50 = 4086.68 nM 5.39 MMV: Inhibition of Trypanosoma brucei brucei (Squib 427) (HAT in vitro). -
Plasmodium falciparum IC50 = 4037.43 nM 5.39 MMV: Measure of pLDH activity as indication of parasite viability. Gametocytogen... -
Unchecked IC50 = 5300.0 nM 5.28 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
MRC5 IC50 = 5656.85 nM 5.25 MMV: Cytotoxicity against human fibroblasts (MRC-5) cells. -
Unchecked IC50 = 10110.0 nM 5.0 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Unchecked IC50 = 12490.0 nM 4.9 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Unchecked IC50 = 13260.0 nM 4.88 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3301486 Unchecked 8
- 10.6019/CHEMBL3301472 Human immunodeficiency virus 1 7
- 10.6019/CHEMBL3301472 NON-PROTEIN TARGET 6
- 10.6019/CHEMBL3301464 Unchecked 4
- 10.6019/CHEMBL3137381 Onchocerca lienalis 4
- 10.6019/CHEMBL2028040 Plasmodium falciparum 3
- 10.6019/CHEMBL3301546 Saccharomyces cerevisiae 3
- 10.6019/CHEMBL2363022 Schistosoma mansoni 3
- 10.6019/CHEMBL2094260 Mycobacterium tuberculosis 2
- 10.6019/CHEMBL3301458 Voltage-gated inwardly rectifying potassium channel KCNH2 2
- 10.6019/CHEMBL3301451 Plasmodium falciparum 2
31284086 10.1016/j.ejmech.2019.06.062 Cruzipain 2
31284086 10.1016/j.ejmech.2019.06.062 Rhodesain 2
- 10.6019/CHEMBL3301555 Plasmodium falciparum 2
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
- 10.6019/CHEMBL2448809 Plasmodium falciparum 1
- 10.6019/CHEMBL2028040 Trypanosoma brucei brucei 1
- 10.6019/CHEMBL2028040 MRC5 1
- 10.6019/CHEMBL2028040 Leishmania infantum 1
- 10.6019/CHEMBL2028040 Trypanosoma brucei rhodesiense 1

Data from ChEMBL 36 via Core Engine