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Compound Detail

CHEMBL2375552

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CC1(C)OC2=C(C(=O)c3ccccc3C2=O)C1n1cc(C2CCCCC2)nn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2375552
Phase Preclinical
Structure Type MOL
InChI Key DNRCXULLPXOXGG-UHFFFAOYSA-N
15
Targets
18
Activities
1
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

377.4
MW (Da)
4.01
ALogP
6
HBA
0
HBD
74.1
PSA (Ų)
0.79
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 C22H23N3O3
MW 377.44
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 0.09

Activity Summary

IC50 18 meas. best 5.86

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Leishmania amazonensis
CHEMBL612877
 IC50 5.86 5.66 1390.0 2
Leishmania infantum
CHEMBL612848
 IC50 5.75 5.745 1780.0 2
HL-60
CHEMBL383
 IC50 5.57 5.57 2700.0 1
MDA-MB-435
CHEMBL614697
 IC50 5.56 5.56 2760.0 1
SF-295
CHEMBL614908
 IC50 5.5 5.5 3180.0 1
MX1
CHEMBL613704
 IC50 5.38 5.38 4210.0 1
PC-3
CHEMBL390
 IC50 5.37 5.37 4290.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.3 5.235 4950.0 2
OVCAR-8
CHEMBL612555
 IC50 5.27 5.27 5380.0 1
HCT-116
CHEMBL394
 IC50 5.26 5.26 5510.0 1
DU-145
CHEMBL613508
 IC50 5.26 5.26 5480.0 1
MCF7
CHEMBL387
 IC50 5.24 5.24 5780.0 1
V79
CHEMBL614074
 IC50 5.21 5.21 6120.0 1
L929
CHEMBL612267
 IC50 5.18 5.18 6620.0 1
PBMC
CHEMBL613107
 IC50 5.13 5.13 7360.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Leishmania amazonensis IC50 = 1390.0 nM 5.86 Antileishmanial activity against antimony-resistant Leishmania amazonensis MHOM/... 23535320
Leishmania infantum IC50 = 1780.0 nM 5.75 Antileishmanial activity against antimony-resistant Leishmania infantum MCAN/BR/... 23535320
Leishmania infantum IC50 = 1830.0 nM 5.74 Antileishmanial activity against antimony-sensitive Leishmania infantum MCAN/BR/... 23535320
HL-60 IC50 = 2700.0 nM 5.57 Cytotoxicity against human HL60 cells assessed as cell viability after 72 hrs by... 24530030
MDA-MB-435 IC50 = 2760.0 nM 5.56 Cytotoxicity against human MDA-MB-435 cells assessed as cell viability after 72 ... 24530030
SF-295 IC50 = 3180.0 nM 5.5 Cytotoxicity against human SF295 cells assessed as cell viability after 72 hrs b... 24530030
Leishmania amazonensis IC50 = 3500.0 nM 5.46 Antileishmanial activity against antimony-sensitive Leishmania amazonensis MHOM/... 23535320
MX1 IC50 = 4210.0 nM 5.38 Cytotoxicity against human MX1 cells assessed as cell viability after 72 hrs by ... 24530030
PC-3 IC50 = 4290.0 nM 5.37 Cytotoxicity against human PC3 cells assessed as cell viability after 72 hrs by ... 24530030
NON-PROTEIN TARGET IC50 = 4950.0 nM 5.3 Cytotoxicity against human Hs578T cells assessed as cell viability after 72 hrs ... 24530030
OVCAR-8 IC50 = 5380.0 nM 5.27 Cytotoxicity against human OVCAR8 cells assessed as cell viability after 72 hrs ... 24530030
DU-145 IC50 = 5480.0 nM 5.26 Cytotoxicity against human DU145 cells assessed as cell viability after 72 hrs b... 24530030
HCT-116 IC50 = 5510.0 nM 5.26 Cytotoxicity against human HCT116 cells assessed as cell viability after 72 hrs ... 24530030
MCF7 IC50 = 5780.0 nM 5.24 Cytotoxicity against human MCF7 cells assessed as cell viability after 72 hrs by... 24530030
V79 IC50 = 6120.0 nM 5.21 Cytotoxicity against chinese hamster V79 cells assessed as cell viability after ... 24530030
L929 IC50 = 6620.0 nM 5.18 Cytotoxicity against mouse L929 cells assessed as cell viability after 72 hrs by... 24530030
NON-PROTEIN TARGET IC50 = 6700.0 nM 5.17 Cytotoxicity against human HCT8 cells assessed as cell viability after 72 hrs by... 24530030
PBMC IC50 = 7360.0 nM 5.13 Cytotoxicity against human PBMC assessed as cell viability after 72 hrs by MTT a... 24530030

Literature References

PubMed DOI Target Context # Activities
23535320 10.1016/j.ejmech.2013.02.038 Unchecked 4
23535320 10.1016/j.ejmech.2013.02.038 Leishmania amazonensis 2
23535320 10.1016/j.ejmech.2013.02.038 Leishmania infantum 2
24530030 10.1016/j.bmc.2014.01.033 NON-PROTEIN TARGET 2
24530030 10.1016/j.bmc.2014.01.033 MX1 1
24530030 10.1016/j.bmc.2014.01.033 HL-60 1
24530030 10.1016/j.bmc.2014.01.033 OVCAR-8 1
24530030 10.1016/j.bmc.2014.01.033 MDA-MB-435 1
24530030 10.1016/j.bmc.2014.01.033 SF-295 1
24530030 10.1016/j.bmc.2014.01.033 HCT-116 1
24530030 10.1016/j.bmc.2014.01.033 PC-3 1
24530030 10.1016/j.bmc.2014.01.033 DU-145 1
24530030 10.1016/j.bmc.2014.01.033 MCF7 1
24530030 10.1016/j.bmc.2014.01.033 PBMC 1
24530030 10.1016/j.bmc.2014.01.033 L929 1
24530030 10.1016/j.bmc.2014.01.033 V79 1
24074878 10.1016/j.bmc.2013.08.055 Trypanosoma cruzi 1
23535320 10.1016/j.ejmech.2013.02.038 ADMET 1

Data from ChEMBL 36 via Core Engine