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Compound Detail

CHEMBL2164802

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COc1ccc2c3c(c4cc(OC)c(OC)cc4c2c1)C[C@H]1CC[C@@H](O)CN1C3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2164802
Phase Preclinical
Structure Type MOL
InChI Key RHTBCPPXWPNYSU-HUUCEWRRSA-N
8
Targets
8
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

393.5
MW (Da)
3.90
ALogP
5
HBA
1
HBD
51.2
PSA (Ų)
0.68
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H27NO4
MW 393.48
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness 0.59

Activity Summary

IC50 7 meas. best 7.67
EC50 1 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 8.52 8.52 3.0 1
Unchecked
CHEMBL612545
 IC50 7.67 7.67 21.3 1
KB
CHEMBL398
 IC50 7.48 7.48 33.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.35 7.35 45.0 1
DU-145
CHEMBL613508
 IC50 7.18 7.18 66.0 1
A549
CHEMBL392
 IC50 7.09 7.09 82.0 1
HepG2 2.2.15
CHEMBL4296438
 IC50 6.59 6.59 258.0 1
SK-BR-3
CHEMBL613834
 IC50 6.46 6.46 348.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 3.0 nM 8.52 Antiviral activity against HCV genotype 1b con1 infected in human Huh-luc/neo-ET... 29317151
Unchecked IC50 = 21.3 nM 7.67 Cytotoxicity against human Huh-luc/neo-ET cells assessed as cell growth inhibiti... 29317151
KB IC50 = 33.0 nM 7.48 Cytotoxicity against human KB cells after 2 hrs by methylene blue staining-based... 22823514
NON-PROTEIN TARGET IC50 = 45.0 nM 7.35 Cytotoxicity against human KBVIN cells overexpressing P-gp after 2 hrs by methyl... 22823514
DU-145 IC50 = 66.0 nM 7.18 Cytotoxicity against human DU145 cells after 2 hrs by methylene blue staining-ba... 22823514
A549 IC50 = 82.0 nM 7.09 Cytotoxicity against human A549 cells after 2 hrs by methylene blue staining-bas... 22823514
HepG2 2.2.15 IC50 = 258.0 nM 6.59 Cytotoxicity against human HepG2(2.2.15) cells assessed as cell growth inhibitio... 29317151
SK-BR-3 IC50 = 348.0 nM 6.46 Cytotoxicity against human SKBR3 cells after 2 hrs by methylene blue staining-ba... 22823514

Literature References

PubMed DOI Target Context # Activities
29317151 10.1016/j.bmc.2017.12.027 Heat shock cognate 71 kDa protein 2
22823514 10.1021/jm3001218 SK-BR-3 1
22823514 10.1021/jm3001218 NON-PROTEIN TARGET 1
22823514 10.1021/jm3001218 KB 1
22823514 10.1021/jm3001218 DU-145 1
22823514 10.1021/jm3001218 A549 1
29317151 10.1016/j.bmc.2017.12.027 Hepatitis C virus 1
29317151 10.1016/j.bmc.2017.12.027 Unchecked 1
29317151 10.1016/j.bmc.2017.12.027 ADMET 1
29317151 10.1016/j.bmc.2017.12.027 Hepatitis B virus 1
29317151 10.1016/j.bmc.2017.12.027 HepG2 2.2.15 1

Data from ChEMBL 36 via Core Engine