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Compound Detail

CHEMBL4466320

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O=C1c2ccccc2C(=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 CHEMBL4466320
Phase Preclinical
Structure Type MOL
InChI Key LPUJFXOPSMZKRQ-HKZZBQCASA-N
7
Targets
11
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

455.4
MW (Da)
0.22
ALogP
8
HBA
5
HBD
139.6
PSA (Ų)
0.21
QED
0
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 C26H17NO7
MW 455.42
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness 1.99

Activity Summary

IC50 10 meas. best 11.0
EC50 1 meas. best 7.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Jurkat
CHEMBL397
 IC50 11.0 10.105 0.0 2
NCM460
CHEMBL4483264
 IC50 10.0 10.0 0.1 1
A549
CHEMBL392
 IC50 9.7 9.085 0.2 2
HUVEC
CHEMBL613979
 IC50 9.52 9.52 0.3 1
Caco-2
CHEMBL614058
 IC50 8.27 7.765 5.4 2
SK-BR-3
CHEMBL613834
 IC50 7.62 7.62 24.2 1
Supercoiled DNA
CHEMBL4649925
 EC50 7.08 7.08 83.3 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Jurkat IC50 = 0.01 nM 11.0 Cytotoxicity against human Jurkat cells incubated for 72 hrs by CCK-8 assay 38483132
NCM460 IC50 = 0.1 nM 10.0 Cytotoxicity against human NCM460 cells incubated for 72 hrs by CCK-8 assay 38483132
A549 IC50 = 0.2 nM 9.7 Cytotoxicity against human A549 cells incubated for 72 hrs by CCK-8 assay 38483132
HUVEC IC50 = 0.3 nM 9.52 Cytotoxicity against human HUVEC cells incubated for 72 hrs by CCK-8 assay 38483132
Jurkat IC50 = 0.62 nM 9.21 Cytotoxicity against human Jurkat cells assessed as inhibition of cell viability... 31490685
A549 IC50 = 3.41 nM 8.47 Cytotoxicity against human A549 cells assessed as inhibition of cell viability i... 31490685
Caco-2 IC50 = 5.4 nM 8.27 Cytotoxicity against human Caco-2 cells incubated for 72 hrs by CCK-8 assay 38483132
SK-BR-3 IC50 = 24.2 nM 7.62 Cytotoxicity against human SKBR3 cells assessed as inhibition of cell viability ... 31490685
Caco-2 IC50 = 55.2 nM 7.26 Cytotoxicity against human Caco2 cells assessed as inhibition of cell viability ... 31490685
Supercoiled DNA EC50 = 83.3 nM 7.08 Induction of supercoiled pBR322 DNA (unknown origin) cleavage assessed as relaxa... 38483132

Literature References

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

Data from ChEMBL 36 via Core Engine