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Compound Detail

CHEMBL587104

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COc1cc(-c2nc(-c3ccccc3)c(-c3ccccc3)[nH]2)cc(OC)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL587104
Phase Preclinical
Structure Type MOL
InChI Key GWQSXPMDIQADHQ-UHFFFAOYSA-N
8
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

372.4
MW (Da)
5.13
ALogP
4
HBA
2
HBD
67.4
PSA (Ų)
0.51
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H20N2O3
MW 372.42
Aromatic Rings 4
Heavy Atoms 28
NP-Likeness -0.27

Activity Summary

IC50 16 meas. best 7.7
EC50 1 meas. best 5.93

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sphingomyelin phosphodiesterase 3
CHEMBL4523470
 IC50 7.7 7.7 20.0 1
NADPH oxidase 1
CHEMBL1287628
 IC50 6.29 6.17 516.9 2
Plasmodium falciparum
CHEMBL364
 EC50 5.93 5.93 1180.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.89 5.8067 1300.0 3
Unchecked
CHEMBL612545
 IC50 5.48 5.028 3340.0 5
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 5.01 5.01 9752.1 1
Trypanosoma brucei brucei
CHEMBL612851
 IC50 4.93 4.93 11852.9 1
Leishmania infantum
CHEMBL612848
 IC50 4.59 4.59 25398.4 1
Trypanosoma cruzi
CHEMBL368
 IC50 4.55 4.55 28315.7 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sphingomyelin phosphodiesterase 3 IC50 = 20.0 nM 7.7 Inhibition of human recombinant nSMase expressed in HEK293 cells using sphingomy... 30921693
NADPH oxidase 1 IC50 = 516.9 nM 6.29 PUBCHEM_BIOASSAY: Late-stage luminescence-based cell-based dose response assay t... -
NADPH oxidase 1 IC50 = 900.0 nM 6.05 PUBCHEM_BIOASSAY: Late stage results from the probe development effort to identi... -
Plasmodium falciparum EC50 = 1180.0 nM 5.93 MMV: Inhibition of Plasmodium falciparum 3D7 (EC50). -
Plasmodium falciparum IC50 = 1300.0 nM 5.89 Antimalarial activity against chloroquine-sensitive asexual erythrocyte stage of... 28197312
Plasmodium falciparum IC50 = 1544.0 nM 5.81 MMV: IC50 determined against P. falciparum Dd2-luc strain using a Malaria Sybr G... -
Plasmodium falciparum IC50 = 1900.0 nM 5.72 Antimalarial activity against chloroquine-resistant asexual erythrocyte stage of... 28197312
Unchecked IC50 = 3340.0 nM 5.48 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Unchecked IC50 = 8030.0 nM 5.09 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Trypanosoma brucei rhodesiense IC50 = 9752.11 nM 5.01 MMV: Inhibition of Trypanosoma brucei rhodesiense (STIB 900) (HAT in vitro). -
Unchecked IC50 = 10200.0 nM 4.99 Inhibition of beta-hematin formation incubated for 5 to 6 hrs by NP40 detergent-... 28197312
Trypanosoma brucei brucei IC50 = 11852.87 nM 4.93 MMV: Inhibition of Trypanosoma brucei brucei (Squib 427) (HAT in vitro). -
Unchecked IC50 = 11950.0 nM 4.92 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Unchecked IC50 = 21730.0 nM 4.66 MMV: Anti-babesial activity assay. Parasite pRBCs at 1% parasitemia were cultiva... -
Leishmania infantum IC50 = 25398.42 nM 4.59 MMV: Inhibition of Leishmania infantum (MHOM/MA/BE/67) in vitro. -
Trypanosoma cruzi IC50 = 28315.68 nM 4.55 MMV: Inhibition of Trypanosoma cruzi (Tulahuen C4 LacZ) (Chagas in vitro). -

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
20485427 10.1038/nature09107 Plasmodium falciparum 4
- 10.6019/CHEMBL2363022 Schistosoma mansoni 3
- 10.6019/CHEMBL3301546 Saccharomyces cerevisiae 3
30921693 10.1016/j.ejmech.2019.03.015 Unchecked 3
30921693 10.1016/j.ejmech.2019.03.015 ADMET 2
- 10.6019/CHEMBL2094260 Mycobacterium tuberculosis 2
- 10.6019/CHEMBL3433997 Glucose transporter 2
28197312 10.1021/acsmedchemlett.6b00416 Plasmodium falciparum 2
- 10.6019/CHEMBL3433997 Solute carrier family 2, facilitated glucose transporter member 1 2
- 10.6019/CHEMBL2028040 Plasmodium falciparum 2
- 10.6019/CHEMBL3433997 Hexose transporter 1 2
- 10.6019/CHEMBL3301451 Plasmodium falciparum 2
- 10.6019/CHEMBL3301458 Voltage-gated inwardly rectifying potassium channel KCNH2 2
28197312 10.1021/acsmedchemlett.6b00416 Unchecked 2
- 10.6019/CHEMBL2448809 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine