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Compound Detail

CHEMBL18351

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COc1ccc(-c2oc3c(OC)c(OC)c(OC)c(O)c3c(=O)c2OC)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL18351
Phase Preclinical
Structure Type MOL
InChI Key GVLMRDDSMVCWKB-UHFFFAOYSA-N
16
Targets
27
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

404.4
MW (Da)
2.91
ALogP
9
HBA
2
HBD
116.8
PSA (Ų)
0.64
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H20O9
MW 404.37
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness 1.37

Activity Summary

IC50 25 meas. best 8.3
Kd 2 meas. best 6.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.3 8.035 5.0 2
K562
CHEMBL385
 IC50 8.15 8.15 7.0 1
KB
CHEMBL398
 IC50 8.1 7.9667 8.0 3
MIA PaCa-2
CHEMBL614725
 IC50 7.92 7.92 12.0 1
HCT-15
CHEMBL612263
 IC50 7.85 7.85 14.0 1
SK-OV-3
CHEMBL614925
 IC50 7.66 7.66 22.0 1
HCT-116
CHEMBL394
 IC50 7.64 7.64 23.0 1
HL-60
CHEMBL383
 IC50 7.44 7.44 36.0 1
OVCAR-8
CHEMBL612555
 IC50 7.4 7.4 40.0 1
A549
CHEMBL392
 IC50 7.24 7.24 58.0 1
MCF7
CHEMBL387
 IC50 6.89 6.89 130.0 1
Tubulin
CHEMBL2095182
 Kd 6.89 6.89 128.8 2
HepG2
CHEMBL395
 IC50 6.76 6.76 174.0 1
SF-268
CHEMBL613977
 IC50 6.73 6.73 186.0 1
Tubulin
CHEMBL2095182
 IC50 6.1 6.0867 800.0 3
Unchecked
CHEMBL612545
 IC50 6.08 5.388 830.0 5
HT-29
CHEMBL384
 IC50 5.5 5.5 3140.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 5.0 nM 8.3 Cytotoxicity against human HL60R cells after 72 hrs by MTS assay 21146994
K562 IC50 = 7.0 nM 8.15 Cytotoxicity against human K562 cells after 72 hrs by MTS assay 21146994
KB IC50 = 8.0 nM 8.1 Cytotoxicity against human KB cells after 72 hrs by MTS assay 20356063
KB IC50 = 8.0 nM 8.1 Cytotoxicity against human KB cells after 72 hrs by MTS assay 21146994
MIA PaCa-2 IC50 = 12.0 nM 7.92 Cytotoxicity against human MIAPaCa2 cells after 72 hrs by MTS assay 21146994
HCT-15 IC50 = 14.0 nM 7.85 Cytotoxicity against human HCT15 cells after 72 hrs by MTS assay 21146994
NON-PROTEIN TARGET IC50 = 17.0 nM 7.77 Cytotoxicity against human MCF7/R cells after 72 hrs by MTS assay 21146994
KB IC50 = 20.0 nM 7.7 Cytotoxicity against human KB cells after 72 hrs by MTS assay 19457664
SK-OV-3 IC50 = 22.0 nM 7.66 Cytotoxicity against human SKOV3 cells after 72 hrs by MTS assay 21146994
HCT-116 IC50 = 23.0 nM 7.64 Cytotoxicity against human HCT116 cells after 72 hrs by MTS assay 21146994
HL-60 IC50 = 36.0 nM 7.44 Cytotoxicity against human HL60 cells after 72 hrs by MTS assay 21146994
OVCAR-8 IC50 = 40.0 nM 7.4 Cytotoxicity against human OVCAR8 cells after 72 hrs by MTS assay 21146994
A549 IC50 = 58.0 nM 7.24 Cytotoxicity against human A549 cells after 72 hrs by MTS assay 21146994
Tubulin Kd = 130.0 nM 6.89 Displacement of [3H]colchicine from tubulin (unknown origin) 23961916
Tubulin Kd = 128.82 nM 6.89 Displacement of [3H]colchicine from tubulin (unknown origin) 23961916
MCF7 IC50 = 130.0 nM 6.89 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 38870715
HepG2 IC50 = 174.0 nM 6.76 Cytotoxicity against human HepG2 cells after 72 hrs by MTS assay 21146994
SF-268 IC50 = 186.0 nM 6.73 Cytotoxicity against human SF268 cells after 72 hrs by MTS assay 21146994
Tubulin IC50 = 800.0 nM 6.1 Inhibition of tubulin polymerization (unknown origin) 38870715
Tubulin IC50 = 830.0 nM 6.08 Inhibitory concentration required against tubulin polymerization in the antimicr... 11354375

Literature References

PubMed DOI Target Context # Activities
21146994 10.1016/j.bmc.2010.11.035 KB 10
21146994 10.1016/j.bmc.2010.11.035 HL-60 8
9632366 10.1021/jm970842h Tubulin 3
7623025 10.1021/np50118a001 NON-PROTEIN TARGET 3
7623025 10.1021/np50118a001 Unchecked 3
7623025 10.1021/np50118a001 SNB-75 2
7623025 10.1021/np50118a001 UO-31 2
7623025 10.1021/np50118a001 SF-539 2
7623025 10.1021/np50118a001 SF-268 2
7623025 10.1021/np50118a001 HCT-116 2
7623025 10.1021/np50118a001 NCI-H522 2
7623025 10.1021/np50118a001 NCI-H460 2
7623025 10.1021/np50118a001 NCI-H226 2
7623025 10.1021/np50118a001 HOP-62 2
7623025 10.1021/np50118a001 SR 2
7623025 10.1021/np50118a001 HL-60(TB) 2
38870715 10.1016/j.bmc.2024.117791 Tubulin 2
7623025 10.1021/np50118a001 SK-MEL-5 2
19457664 10.1016/j.bmcl.2009.05.008 KB 2
7623025 10.1021/np50118a001 OVCAR-3 2

Data from ChEMBL 36 via Core Engine