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Compound Detail

CHEMBL261297

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COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(OC(C)=O)c(OC)c2)ccc1OC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL261297
Phase Preclinical
Structure Type MOL
InChI Key GQRYDKSIXWXTSH-NXZHAISVSA-N
6
Targets
9
Activities
2
Assay Types
0
PK Parameters
13
Publications
0
Known Names

Molecular Properties

452.5
MW (Da)
3.81
ALogP
8
HBA
0
HBD
105.2
PSA (Ų)
0.23
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H24O8
MW 452.46
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness 0.51

Activity Summary

EC50 6 meas. best 5.92
IC50 3 meas. best 5.63

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei brucei
CHEMBL612851
 EC50 5.92 5.7933 1200.0 3
Plasmodium falciparum
CHEMBL364
 IC50 5.63 5.615 2340.0 2
Leishmania mexicana
CHEMBL612880
 EC50 4.47 4.47 34000.0 1
Unchecked
CHEMBL612545
 IC50 4.22 4.22 60000.0 1
Leishmania major
CHEMBL612879
 EC50 4.14 4.14 73000.0 1
HEK293
CHEMBL614818
 EC50 4.1 4.1 80000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei brucei EC50 = 1200.0 nM 5.92 Antitrypanosomal activity against multidrug-resistant Trypanosoma brucei brucei ... 20004045
Trypanosoma brucei brucei EC50 = 1600.0 nM 5.8 Antitrypanosomal activity against Trypanosoma brucei brucei 427 after 48 hrs by ... 20004045
Trypanosoma brucei brucei EC50 = 2200.0 nM 5.66 Antitrypanosomal activity against diminazene-resistant Trypanosoma brucei brucei... 20004045
Plasmodium falciparum IC50 = 2340.0 nM 5.63 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum FCK2 18194869
Plasmodium falciparum IC50 = 2510.0 nM 5.6 Antimalarial activity against chloroquine-resistant Plasmodium falciparum MP14 18194869
Leishmania mexicana EC50 = 34000.0 nM 4.47 Antileishmanial activity against Leishmania mexicana MNYC/BZ/62/M379 amastigotes... 20004045
Unchecked IC50 = 60000.0 nM 4.22 Inhibition of goat brain tubulin polymerization assessed as turbidity by UV spec... 21830815
Leishmania major EC50 = 73000.0 nM 4.14 Antileishmanial activity against Leishmania major Friedlin promastigotes after 4... 20004045
HEK293 EC50 = 80000.0 nM 4.1 Cytotoxicity against HEK293 cells after 16 hrs by alamar blue assay 20004045

Literature References

PubMed DOI Target Context # Activities
27521589 10.1016/j.ejmech.2016.07.017 NON-PROTEIN TARGET 10
18194869 10.1016/j.bmc.2007.12.054 Plasmodium falciparum 4
20004045 10.1016/j.ejmech.2009.11.035 Trypanosoma brucei brucei 3
27521589 10.1016/j.ejmech.2016.07.017 No relevant target 3
27521589 10.1016/j.ejmech.2016.07.017 CHO 2
27521589 10.1016/j.ejmech.2016.07.017 Caco-2 2
27521589 10.1016/j.ejmech.2016.07.017 HT-29 2
27521589 10.1016/j.ejmech.2016.07.017 EA.hy 926 2
20004045 10.1016/j.ejmech.2009.11.035 Leishmania major 1
20004045 10.1016/j.ejmech.2009.11.035 Leishmania mexicana 1
20004045 10.1016/j.ejmech.2009.11.035 HEK293 1
20691508 10.1016/j.ejmech.2010.07.003 Mycobacterium tuberculosis 1
21830815 10.1021/jm2004046 Unchecked 1

Data from ChEMBL 36 via Core Engine