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Compound Detail

CHEMBL4472466

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O=C1c2cccc(O)c2C(=O)c2c3c(cc(O)c21)[C@@]12O[C@@]1([C@H](O)CO)[C@H](C#C/C=C\C#C[C@H]2O)N3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4472466
Phase Preclinical
Structure Type MOL
InChI Key BUWSAXYRPMZMDH-LGKAZVCASA-N
8
Targets
11
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

471.4
MW (Da)
-0.08
ALogP
9
HBA
6
HBD
159.8
PSA (Ų)
0.17
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C26H17NO8
MW 471.42
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness 2.19

Activity Summary

IC50 10 meas. best 11.0
EC50 1 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 11.0 11.0 0.0 1
Jurkat
CHEMBL397
 IC50 10.7 10.235 0.0 2
A549
CHEMBL392
 IC50 9.7 9.66 0.2 2
NCM460
CHEMBL4483264
 IC50 9.7 9.7 0.2 1
HUVEC
CHEMBL613979
 IC50 9.1 9.1 0.8 1
SK-BR-3
CHEMBL613834
 IC50 8.59 8.59 2.6 1
Caco-2
CHEMBL614058
 IC50 8.5 8.185 3.2 2
Supercoiled DNA
CHEMBL4649925
 EC50 6.58 6.58 260.6 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.01 nM 11.0 Cytotoxicity against human KPL-4 cells incubated for 72 hrs by CCK-8 assay 38483132
Jurkat IC50 = 0.02 nM 10.7 Cytotoxicity against human Jurkat cells incubated for 72 hrs by CCK-8 assay 38483132
Jurkat IC50 = 0.17 nM 9.77 Cytotoxicity against human Jurkat cells assessed as inhibition of cell viability... 31490685
A549 IC50 = 0.2 nM 9.7 Cytotoxicity against human A549 cells incubated for 72 hrs by CCK-8 assay 38483132
NCM460 IC50 = 0.2 nM 9.7 Cytotoxicity against human NCM460 cells incubated for 72 hrs by CCK-8 assay 38483132
A549 IC50 = 0.24 nM 9.62 Cytotoxicity against human A549 cells assessed as inhibition of cell viability i... 31490685
HUVEC IC50 = 0.8 nM 9.1 Cytotoxicity against human HUVEC cells incubated for 72 hrs by CCK-8 assay 38483132
SK-BR-3 IC50 = 2.56 nM 8.59 Cytotoxicity against human SKBR3 cells assessed as inhibition of cell viability ... 31490685
Caco-2 IC50 = 3.16 nM 8.5 Cytotoxicity against human Caco2 cells assessed as inhibition of cell viability ... 31490685
Caco-2 IC50 = 13.5 nM 7.87 Cytotoxicity against human Caco-2 cells incubated for 72 hrs by CCK-8 assay 38483132
Supercoiled DNA EC50 = 260.6 nM 6.58 Induction of supercoiled pBR322 DNA (unknown origin) cleavage assessed as relaxa... 38483132

Literature References

PubMed DOI Target Context # Activities
31490685 10.1021/acs.jnatprod.9b00229 Staphylococcus aureus 4
31490685 10.1021/acs.jnatprod.9b00229 SK-BR-3 3
31490685 10.1021/acs.jnatprod.9b00229 Caco-2 2
31490685 10.1021/acs.jnatprod.9b00229 Jurkat 1
31490685 10.1021/acs.jnatprod.9b00229 A549 1
31490685 10.1021/acs.jnatprod.9b00229 Escherichia coli 1
38483132 10.1021/acs.jmedchem.3c02049 Jurkat 1
38483132 10.1021/acs.jmedchem.3c02049 A549 1
38483132 10.1021/acs.jmedchem.3c02049 Caco-2 1
38483132 10.1021/acs.jmedchem.3c02049 Unchecked 1
38483132 10.1021/acs.jmedchem.3c02049 NCM460 1
38483132 10.1021/acs.jmedchem.3c02049 HUVEC 1
38483132 10.1021/acs.jmedchem.3c02049 Supercoiled DNA 1
38483132 10.1021/acs.jmedchem.3c02049 DNA 1
38483132 10.1021/acs.jmedchem.3c02049 Calf thymus DNA 1

Data from ChEMBL 36 via Core Engine