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Compound Detail

CHEMBL2164803

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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 CHEMBL2164803
Phase Preclinical
Structure Type MOL
InChI Key RHTBCPPXWPNYSU-CABCVRRESA-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 5.8
EC50 1 meas. best 6.61

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 6.61 6.61 246.1 1
HepG2 2.2.15
CHEMBL4296438
 IC50 5.8 5.8 1600.0 1
KB
CHEMBL398
 IC50 5.65 5.65 2250.0 1
DU-145
CHEMBL613508
 IC50 5.65 5.65 2250.0 1
A549
CHEMBL392
 IC50 5.6 5.6 2510.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.51 5.51 3070.0 1
Unchecked
CHEMBL612545
 IC50 5.43 5.43 3750.0 1
SK-BR-3
CHEMBL613834
 IC50 5.19 5.19 6440.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 246.1 nM 6.61 Antiviral activity against HCV genotype 1b con1 infected in human Huh-luc/neo-ET... 29317151
HepG2 2.2.15 IC50 = 1600.0 nM 5.8 Cytotoxicity against human HepG2(2.2.15) cells assessed as cell growth inhibitio... 29317151
KB IC50 = 2250.0 nM 5.65 Cytotoxicity against human KB cells after 2 hrs by methylene blue staining-based... 22823514
DU-145 IC50 = 2250.0 nM 5.65 Cytotoxicity against human DU145 cells after 2 hrs by methylene blue staining-ba... 22823514
A549 IC50 = 2510.0 nM 5.6 Cytotoxicity against human A549 cells after 2 hrs by methylene blue staining-bas... 22823514
NON-PROTEIN TARGET IC50 = 3070.0 nM 5.51 Cytotoxicity against human KBVIN cells overexpressing P-gp after 2 hrs by methyl... 22823514
Unchecked IC50 = 3750.0 nM 5.43 Cytotoxicity against human Huh-luc/neo-ET cells assessed as cell growth inhibiti... 29317151
SK-BR-3 IC50 = 6440.0 nM 5.19 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