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Compound Detail

CHEMBL256155

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O=C1C=C(Oc2ccccc2)C(=O)c2ccccc21

Basic Information

ChEMBL ID CHEMBL256155
Phase Preclinical
Structure Type MOL
InChI Key UCWKLNZSXHXPMB-UHFFFAOYSA-N
10
Targets
21
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

250.2
MW (Da)
3.03
ALogP
3
HBA
0
HBD
43.4
PSA (Ų)
0.82
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H10O3
MW 250.25
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness 0.61

Activity Summary

IC50 21 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma cruzi
CHEMBL368
IC50 7.3 6.3667 50.0 3
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 7.1 7.1 80.0 3
Glyceraldehyde-3-phosphate dehydrogenase
CHEMBL2284
IC50 6.23 6.23 590.0 1
Leishmania donovani
CHEMBL367
IC50 6.13 5.9767 740.0 3
IGROV-1
CHEMBL613984
IC50 5.46 5.46 3430.0 1
HT-29
CHEMBL384
IC50 5.36 5.36 4400.0 1
Unchecked
CHEMBL612545
IC50 5.33 5.0075 4690.0 4
L6
CHEMBL614793
IC50 5.23 5.23 5910.0 3
ADMET
CHEMBL612558
IC50 5.01 5.01 9840.0 1
J774
CHEMBL614123
IC50 4.9 4.9 12500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma cruzi IC50 = 50.0 nM 7.3 Trypanocidal activity against Trypanosoma cruzi Y epimastigotes infected in mous... 25008454
Trypanosoma brucei rhodesiense IC50 = 80.0 nM 7.1 Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB900 trypoma... 18353643
Trypanosoma brucei rhodesiense IC50 = 80.0 nM 7.1 Antitrypanosomal activity against Trypanosoma brucei rhodesiense 19606868
Trypanosoma brucei rhodesiense IC50 = 80.0 nM 7.1 Antitrypanosomal activity against trypomastigote form of Trypanosoma brucei rhod... 23153330
Glyceraldehyde-3-phosphate dehydrogenase IC50 = 590.0 nM 6.23 Inhibition of recombinant human GAPDH assessed as oxidative phosphorylation of D... 26237241
Leishmania donovani IC50 = 740.0 nM 6.13 Antitrypanosomal activity against promastigote form of Leishmania donovani MHOM/... 23153330
Trypanosoma cruzi IC50 = 1260.0 nM 5.9 Antitrypanosomal activity against Trypanosoma cruzi Tulahuen C4 amastigotes by m... 18353643
Leishmania donovani IC50 = 1260.0 nM 5.9 Antileishmanial activity against Leishmania donovani MHOM-ET-67/L82 amastigotes ... 18353643
Leishmania donovani IC50 = 1260.0 nM 5.9 Antitrypanosomal activity against axenic amastigote form of Leishmania donovani ... 23153330
Trypanosoma cruzi IC50 = 1260.0 nM 5.9 Antitrypanosomal activity against intracellular amastigote form of Trypanosoma c... 23153330
IGROV-1 IC50 = 3430.0 nM 5.46 Cytotoxicity against human IGROV1 cells after 24 hrs by MTT assay 26237241
HT-29 IC50 = 4400.0 nM 5.36 Cytotoxicity against human HT-29 cells after 24 hrs by MTT assay 26237241
Unchecked IC50 = 4700.0 nM 5.33 Selectivity index, ratio of IC50 for rat L6 cells to IC50 for Trypanosoma cruzi ... 18353643
Unchecked IC50 = 4690.0 nM 5.33 Selectivity index, ratio of IC50 for rat L6 cells to IC50 for Leishmania donovan... 18353643
Unchecked IC50 = 5730.0 nM 5.24 Inhibition of recombinant Trypanosoma brucei GAPDH assessed as oxidative phospho... 26237241
L6 IC50 = 5920.0 nM 5.23 Cytotoxicity against rat L6 cells 18353643
L6 IC50 = 5920.0 nM 5.23 Cytotoxicity against rat L6 cells assessed as growth inhibition after 72 hrs by ... 23153330
L6 IC50 = 5910.0 nM 5.23 Cytotoxicity against rat L6 cells after 72 hrs by alamar blue assay 26237241
ADMET IC50 = 9840.0 nM 5.01 Cytotoxicity against HDF after 24 hrs by MTT assay 26237241
J774 IC50 = 12500.0 nM 4.9 Cytotoxicity against mouse J774 cells assessed as cell viability after 48 hrs by... 25008454

Literature References

PubMed DOI Target Context # Activities
26237241 10.1021/acs.jmedchem.5b00748 Unchecked 4
23153330 10.1021/jm301112z Unchecked 4
18353643 10.1016/j.bmcl.2008.03.009 Unchecked 3
23153330 10.1021/jm301112z Leishmania donovani 2
26237241 10.1021/acs.jmedchem.5b00748 IGROV-1 2
26237241 10.1021/acs.jmedchem.5b00748 HT-29 2
25008454 10.1016/j.bmcl.2014.06.044 Trypanosoma cruzi 2
29031061 10.1016/j.ejmech.2017.10.005 Trypanothione reductase 2
23153330 10.1021/jm301112z Trypanothione reductase 1
23153330 10.1021/jm301112z L6 1
18353643 10.1016/j.bmcl.2008.03.009 Trypanosoma brucei rhodesiense 1
23153330 10.1021/jm301112z Trypanosoma cruzi 1
23153330 10.1021/jm301112z Trypanosoma brucei rhodesiense 1
25008454 10.1016/j.bmcl.2014.06.044 Unchecked 1
19606868 10.1021/jm9004835 NON-PROTEIN TARGET 1
19606868 10.1021/jm9004835 Trypanosoma brucei rhodesiense 1
- 10.1039/C4MD00069B Trypanosoma brucei rhodesiense 1
- 10.1039/C4MD00069B Unchecked 1
18353643 10.1016/j.bmcl.2008.03.009 L6 1
38310976 10.1016/j.bmcl.2024.129642 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine