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Compound Detail

CHEMBL505932

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COc1cc2c(O[C@@H]3O[C@H](C)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)c3c(c(-c4ccc5c(c4)OCO5)c2cc1OC)C(=O)OC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL505932
Phase Preclinical
Structure Type MOL
InChI Key BWGZOLFCSSJAKB-BLWCVCJGSA-N
4
Targets
10
Activities
1
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

652.6
MW (Da)
3.84
ALogP
14
HBA
0
HBD
160.6
PSA (Ų)
0.25
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C33H32O14
MW 652.61
Aromatic Rings 3
Heavy Atoms 47
NP-Likeness 1.23

Activity Summary

IC50 10 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MCF7
CHEMBL387
 IC50 8.7 7.4367 2.0 3
KB
CHEMBL398
 IC50 7.85 6.6967 14.0 3
HCT-116
CHEMBL394
 IC50 7.8 7.185 16.0 2
K562
CHEMBL385
 IC50 6.09 5.605 808.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MCF7 IC50 = 2.0 nM 8.7 Cytotoxicity against doxorubicin-sensitive human MCF7 cells 15921419
KB IC50 = 14.0 nM 7.85 Cytotoxicity against human KB cells 15921419
HCT-116 IC50 = 16.0 nM 7.8 Cytotoxicity against human HCT116 cells 15921419
MCF7 IC50 = 65.0 nM 7.19 Cytotoxicity against doxorubicin-resistant human MCF7 cells 15921419
HCT-116 IC50 = 270.0 nM 6.57 Cytotoxicity against human HCT116 cells after 72 hrs by sulforhodamine B and MTT... 22119124
MCF7 IC50 = 380.0 nM 6.42 Cytotoxicity against human MCF7 cells after 72 hrs by sulforhodamine B and MTT a... 22119124
KB IC50 = 440.0 nM 6.36 Cytotoxicity against human KB cells after 72 hrs by sulforhodamine B and MTT ass... 22119124
K562 IC50 = 808.0 nM 6.09 Cytotoxicity against human K562 cells after 72 hrs by sulforhodamine B and MTT a... 22119124
KB IC50 = 1320.0 nM 5.88 Cytotoxicity against vincristine-selected multi drug-resistant human KB cells af... 22119124
K562 IC50 = 7660.0 nM 5.12 Cytotoxicity against adriamycin-selected multi drug-resistant human K562 cells a... 22119124

Literature References

PubMed DOI Target Context # Activities
22119124 10.1016/j.ejmech.2011.11.011 HL-60 11
22119124 10.1016/j.ejmech.2011.11.011 HCT-116 7
22119124 10.1016/j.ejmech.2011.11.011 KB 3
22119124 10.1016/j.ejmech.2011.11.011 K562 3
15921419 10.1021/np050028u MCF7 2
15921419 10.1021/np050028u KB 1
15921419 10.1021/np050028u HCT-116 1
22119124 10.1016/j.ejmech.2011.11.011 MCF7 1
22119124 10.1016/j.ejmech.2011.11.011 DNA topoisomerase 2-alpha 1

Data from ChEMBL 36 via Core Engine