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Compound Detail

CHEMBL1224755

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O=C1/C(=C/c2ccncc2)CCC/C1=C\c1ccncc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1224755
Phase Preclinical
Structure Type MOL
InChI Key CYVVJSKZRBZHAV-UNZYHPAISA-N
15
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

276.3
MW (Da)
3.70
ALogP
3
HBA
0
HBD
42.9
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 C18H16N2O
MW 276.34
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.44

Activity Summary

IC50 13 meas. best 7.52
EC50 4 meas. best 6.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei brucei
CHEMBL612851
 IC50 7.52 7.52 30.0 1
SK-BR-3
CHEMBL613834
 IC50 6.7 6.7 200.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.57 6.47 270.0 2
BJ
CHEMBL614358
 EC50 6.32 6.32 474.0 1
MDA-MB-231
CHEMBL400
 EC50 5.96 5.96 1100.0 1
Leishmania amazonensis
CHEMBL612877
 IC50 5.92 5.92 1200.0 1
MDA-MB-468
CHEMBL614335
 EC50 5.72 5.72 1900.0 1
MRC5
CHEMBL614181
 IC50 5.71 5.71 1940.0 1
PC-3
CHEMBL390
 IC50 5.67 5.67 2120.0 1
PANC-1
CHEMBL614139
 IC50 5.66 5.66 2180.0 1
HT-29
CHEMBL384
 IC50 5.63 5.63 2350.0 1
Unchecked
CHEMBL612545
 IC50 5.6 5.6 2500.0 1
X-box-binding protein 1
CHEMBL1741176
 IC50 5.0 5.0 10000.0 1
DNA damage-inducible transcript 3 protein
CHEMBL2146304
 IC50 5.0 5.0 10000.0 1
Unchecked
CHEMBL612545
 EC50 5.0 5.0 10100.0 1
Trypanothione reductase
CHEMBL5131
 IC50 4.83 4.83 14700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei brucei IC50 = 30.0 nM 7.52 DNDI: Inhibition of Human African Trypanosomiasis (HAT), STIB 795, in vitro -
SK-BR-3 IC50 = 200.0 nM 6.7 Cytotoxicity against human SKBR3 cells after 72 hrs by SRB assay 20728364
NON-PROTEIN TARGET IC50 = 270.0 nM 6.57 Cytotoxicity against human NB4 cells assessed as reduction in cell viability aft... 24960549
NON-PROTEIN TARGET IC50 = 430.0 nM 6.37 Cytotoxicity against human NB4-R1 cells assessed as reduction in cell viability ... 24960549
BJ EC50 = 474.0 nM 6.32 PUBCHEM_BIOASSAY: Fluorescence Cell-Based Dose Response to Characterize Compound... -
MDA-MB-231 EC50 = 1100.0 nM 5.96 Cytotoxicity against human MDA-MB-231 cells after 72 hrs by SRB assay 20728364
Leishmania amazonensis IC50 = 1200.0 nM 5.92 Antileishmanial activity against Leishmania amazonensis IFLA/BR/1967/PH-8 promas... 24321832
MDA-MB-468 EC50 = 1900.0 nM 5.72 Cytotoxicity against human MDA-MB-468 cells after 72 hrs by SRB assay 20728364
MRC5 IC50 = 1940.0 nM 5.71 DNDI: Cytotoxicity against human MRC-5 lung fibroblast cells. -
PC-3 IC50 = 2120.0 nM 5.67 Cytotoxicity against human PC3 cells after 72 hrs by MTT assay 22551677
PANC-1 IC50 = 2180.0 nM 5.66 Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay 22551677
HT-29 IC50 = 2350.0 nM 5.63 Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay 22551677
Unchecked IC50 = 2500.0 nM 5.6 Inhibition of NF-kappaB activation in human K562 cells 20728364
Unchecked EC50 = 10100.0 nM 5.0 PUBCHEM_BIOASSAY: Dose response confirmation of uHTS hits that enhance the survi... -
X-box-binding protein 1 IC50 = 10000.0 nM 5.0 PUBCHEM_BIOASSAY: XBP1 DR counterscreen for CHOP. (Class of assay: confirmatory)... -
DNA damage-inducible transcript 3 protein IC50 = 10000.0 nM 5.0 PUBCHEM_BIOASSAY: CHOP dose-response primary assay. (Class of assay: confirmator... -
Trypanothione reductase IC50 = 14700.0 nM 4.83 Inhibition of Trypanosoma cruzi trypanothione reductase expressed in Escherichia... 24321832

Literature References

PubMed DOI Target Context # Activities
20728364 10.1016/j.bmc.2010.07.063 MDA-MB-231 3
37473689 10.1016/j.ejmech.2023.115623 Unchecked 2
24960549 10.1021/jm401352a NON-PROTEIN TARGET 2
24321832 10.1016/j.ejmech.2013.11.011 Cruzipain 2
24321832 10.1016/j.ejmech.2013.11.011 Trypanothione reductase 2
37473689 10.1016/j.ejmech.2023.115623 Human immunodeficiency virus 1 1
20728364 10.1016/j.bmc.2010.07.063 Unchecked 1
37473689 10.1016/j.ejmech.2023.115623 SUP-T1 1
24321832 10.1016/j.ejmech.2013.11.011 Trypanosoma cruzi 1
24321832 10.1016/j.ejmech.2013.11.011 Leishmania amazonensis 1
24321832 10.1016/j.ejmech.2013.11.011 ADMET 1
24321832 10.1016/j.ejmech.2013.11.011 Unchecked 1
24321832 10.1016/j.ejmech.2013.11.011 Glutathione reductase, mitochondrial 1
- 10.6019/CHEMBL2094269 MRC5 1
- 10.6019/CHEMBL2094269 Trypanosoma brucei brucei 1
22551677 10.1016/j.ejmech.2012.04.005 HT-29 1
22551677 10.1016/j.ejmech.2012.04.005 PANC-1 1
22551677 10.1016/j.ejmech.2012.04.005 PC-3 1
20728364 10.1016/j.bmc.2010.07.063 SK-BR-3 1
20728364 10.1016/j.bmc.2010.07.063 MDA-MB-468 1

Data from ChEMBL 36 via Core Engine