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Compound Detail

CHEMBL556074

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COc1cc(OC)c2c(c1)O[C@@]1(c3ccc(Br)cc3)[C@H](c3ccccc3)C[C@@H](O)[C@@]21O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL556074
Phase Preclinical
Structure Type MOL
InChI Key ACIXIVSDWSWVDW-MCWSDJLFSA-N
12
Targets
18
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

483.4
MW (Da)
4.49
ALogP
5
HBA
2
HBD
68.2
PSA (Ų)
0.57
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H23BrO5
MW 483.36
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness 1.46

Activity Summary

IC50 18 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 9.0 9.0 1.0 1
HCT-15
CHEMBL612263
 IC50 9.0 9.0 1.0 1
KB
CHEMBL398
 IC50 8.62 8.22 2.4 2
HL-60
CHEMBL383
 IC50 8.42 8.34 3.8 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.42 8.295 3.8 4
HepG2
CHEMBL395
 IC50 8.4 8.4 4.0 1
HCT-116
CHEMBL394
 IC50 8.24 8.18 5.8 2
SK-OV-3
CHEMBL614925
 IC50 8.07 8.07 8.5 1
SW48
CHEMBL614055
 IC50 8.0 8.0 10.0 1
PC-3
CHEMBL390
 IC50 7.77 7.77 17.0 1
Chikungunya virus
CHEMBL4296563
 IC50 7.65 7.65 22.4 1
Unchecked
CHEMBL612545
 IC50 6.7 6.7 200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-15 IC50 = 1.0 nM 9.0 Cytotoxicity against human HCT15 cells after 72 hrs by MTS assay 19655762
MCF7 IC50 = 1.0 nM 9.0 Cytotoxicity against human MCF7 cells after 72 hrs by MTS assay 19655762
KB IC50 = 2.4 nM 8.62 Cytotoxicity against human KB cells incubated for 72 hrs by MTS assay 23072299
NON-PROTEIN TARGET IC50 = 3.8 nM 8.42 Cytotoxicity against human MDA231 cells after 72 hrs by MTS assay 21142180
HL-60 IC50 = 3.8 nM 8.42 Cytotoxicity against human HL60 cells incubated for 72 hrs by MTS assay 23072299
HepG2 IC50 = 4.0 nM 8.4 Cytotoxicity against human HepG2 cells after 72 hrs by MTS assay 19655762
NON-PROTEIN TARGET IC50 = 4.5 nM 8.35 Cytotoxicity against human HL60R cells after 72 hrs by MTS assay 21142180
NON-PROTEIN TARGET IC50 = 4.5 nM 8.35 Cytotoxicity against human HL60R cells overexpressing Pgp incubated for 72 hrs b... 23072299
HL-60 IC50 = 5.5 nM 8.26 Cytotoxicity against human HL60 cells after 72 hrs by MTS assay 21142180
HCT-116 IC50 = 5.8 nM 8.24 Cytotoxicity against human HCT116 cells incubated for 72 hrs by MTS assay 23072299
HCT-116 IC50 = 7.6 nM 8.12 Cytotoxicity against human HCT116 cells after 72 hrs by MTS assay 21142180
SK-OV-3 IC50 = 8.5 nM 8.07 Cytotoxicity against human SKOV3 cells after 72 hrs by MTS assay 21142180
NON-PROTEIN TARGET IC50 = 8.7 nM 8.06 Cytotoxicity against human MDA435 cells after 72 hrs by MTS assay 21142180
SW48 IC50 = 10.0 nM 8.0 Anticancer activity against human SW48 cells assessed as cell growth inhibition 33445154
KB IC50 = 15.0 nM 7.82 Cytotoxicity against human KB cells after 72 hrs by MTS assay 21142180
PC-3 IC50 = 17.0 nM 7.77 Cytotoxicity against human PC3 cells after 72 hrs by MTS assay 21142180
Chikungunya virus IC50 = 22.4 nM 7.65 Antiviral activity against CHIKV infected in HEK293T cells 38394369
Unchecked IC50 = 200.0 nM 6.7 Inhibition of capped and polyadenylated luciferase mRNA in rabbit reticulocyte l... 19655762

Literature References

PubMed DOI Target Context # Activities
19655762 10.1021/jm900365v HL-60 13
19655762 10.1021/jm900365v HeLa 9
31735574 10.1016/j.ejmech.2019.111859 H9c2 6
19655762 10.1021/jm900365v H9c2 5
21142180 10.1021/jm101318b NON-PROTEIN TARGET 3
19655762 10.1021/jm900365v Unchecked 3
23072299 10.1021/jm301201z H9c2 2
19655762 10.1021/jm900365v MCF7 2
23072299 10.1021/jm301201z Mus musculus 2
23072299 10.1021/jm301201z NON-PROTEIN TARGET 2
19655762 10.1021/jm900365v Mus musculus 2
19655762 10.1021/jm900365v HepG2 2
21142180 10.1021/jm101318b HL-60 1
19655762 10.1021/jm900365v ATP-dependent translocase ABCB1 1
21142180 10.1021/jm101318b KB 1
21142180 10.1021/jm101318b HCT-116 1
19655762 10.1021/jm900365v HCT-116 1
21142180 10.1021/jm101318b PC-3 1
38394369 10.1021/acs.jmedchem.3c01543 Chikungunya virus 1
23072299 10.1021/jm301201z HCT-116 1

Data from ChEMBL 36 via Core Engine