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Compound Detail

CHEMBL498271

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C=C(c1ccc(OC)c(O)c1)c1cc(OC)c(OC)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL498271
Phase Preclinical
Structure Type MOL
InChI Key CNGKIRSNRQSORA-UHFFFAOYSA-N
27
Targets
94
Activities
1
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

316.4
MW (Da)
3.49
ALogP
5
HBA
1
HBD
57.1
PSA (Ų)
0.88
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H20O5
MW 316.35
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.50

Activity Summary

IC50 94 meas. best 9.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 9.19 8.6189 0.6 9
K562
CHEMBL385
 IC50 9.1 8.55 0.8 9
HT-1080
CHEMBL614580
 IC50 9.04 9.04 0.9 1
PC-3
CHEMBL390
 IC50 9.0 9.0 1.0 1
K-562R
CHEMBL4296447
 IC50 8.96 8.6517 1.1 6
HUVEC
CHEMBL613979
 IC50 8.7 8.7 2.0 1
Unchecked
CHEMBL612545
 IC50 8.7 6.6283 2.0 23
MDA-MB-231
CHEMBL400
 IC50 8.7 8.3925 2.0 4
A2780
CHEMBL614004
 IC50 8.52 8.05 3.0 2
MIA PaCa-2
CHEMBL614725
 IC50 8.52 8.205 3.0 4
JIMT-1
CHEMBL4296443
 IC50 8.51 8.51 3.1 1
A549
CHEMBL392
 IC50 8.46 7.9357 3.5 7
LoVo
CHEMBL614721
 IC50 8.43 8.43 3.7 1
RKO
CHEMBL614879
 IC50 8.42 8.42 3.8 1
HT-29
CHEMBL384
 IC50 8.42 7.03 3.8 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.3 8.225 5.0 2
SK-OV-3
CHEMBL614925
 IC50 8.3 8.3 5.0 1
HeLa
CHEMBL399
 IC50 8.22 7.645 6.0 2
Tubulin
CHEMBL2095182
 IC50 8.22 8.22 6.0 1
H22
CHEMBL614998
 IC50 8.1 8.1 8.0 1
U-87 MG
CHEMBL614247
 IC50 8.1 8.09 8.0 3
MCF7
CHEMBL387
 IC50 8.1 7.5725 8.0 4
HepG2
CHEMBL395
 IC50 8.0 7.87 10.0 2
NCI-N87
CHEMBL614197
 IC50 7.85 7.85 14.0 1
MGC-803
CHEMBL3706566
 IC50 7.7 7.7 19.8 1
A549/CDDP
CHEMBL4483225
 IC50 7.16 7.16 69.1 1
PBL
CHEMBL614233
 IC50 5.77 5.77 1700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 2.73 mL.min-1.g-1 Rattus norvegicus
CL 0.96 mL.min-1.g-1 Homo sapiens
T1/2 1.698 hr Rattus norvegicus
T1/2 29.0 hr Homo sapiens
T1/2 18.0 hr Rattus norvegicus
T1/2 18.0 hr Rattus norvegicus
T1/2 30.0 hr Homo sapiens
T1/2 4.24 hr Rattus norvegicus
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 0.64 nM 9.19 Cytotoxicity against human HCT-116 cells assessed as inhibition of cell growth m... 34171660
K562 IC50 = 0.8 nM 9.1 Cytotoxicity against human K562 cells assessed as reduction in cell growth measu... 30818177
K562 IC50 = 0.8 nM 9.1 Cytotoxicity against human K562 cells assessed as decrease in cell growth after ... 28166995
HT-1080 IC50 = 0.91 nM 9.04 Cytotoxicity against human HT-1080 cells assessed as inhibition of cell growth m... 34171660
PC-3 IC50 = 1.0 nM 9.0 Cytotoxicity against human PC3 cells assessed as reduction in cell viability inc... 28803799
K-562R IC50 = 1.1 nM 8.96 Cytotoxicity against human K562R cells assessed as decrease in cell growth after... 28166995
K-562R IC50 = 1.1 nM 8.96 Cytotoxicity against human K562R cells assessed as reduction in cell growth meas... 30818177
HCT-116 IC50 = 1.8 nM 8.74 Cytotoxicity against human HCT116 cells assessed as reduction in cell growth mea... 30818177
K562 IC50 = 2.0 nM 8.7 Antiproliferative activity against human K562 cells after 72 hrs by MTS assay 30525602
HCT-116 IC50 = 2.0 nM 8.7 Cytotoxicity against human HCT116 cells assessed as decrease in cell growth afte... 28166995
HCT-116 IC50 = 2.0 nM 8.7 Cytotoxicity against human HCT116 cells after 72 hrs 20627378
Unchecked IC50 = 2.0 nM 8.7 Inhibition of sheep brain tubulin polymerization assessed as reduction in rate o... 29202409
HCT-116 IC50 = 2.0 nM 8.7 Antiproliferative activity against human HCT116 cells after 72 hrs by resazurin-... 29202409
HCT-116 IC50 = 2.0 nM 8.7 Antiproliferative activity against human HCT116 cells after 72 hrs by MTS assay 30525602
MDA-MB-231 IC50 = 1.98 nM 8.7 Cytotoxicity against human MDA-MB-231 cells assessed as inhibition of cell growt... 34171660
HUVEC IC50 = 2.0 nM 8.7 Antiproliferative activity against HUVEC after 72 hrs by MTS assay 30525602
K-562R IC50 = 2.2 nM 8.66 Antiproliferative activity against human K562R cells after 72 hrs by resazurin-b... 29202409
HCT-116 IC50 = 2.4 nM 8.62 Antiproliferative activity against human HCT116 cells assessed as cell viability... 33038796
HCT-116 IC50 = 2.5 nM 8.6 Cytotoxicity against human HCT116 cells after 72 hrs 19530698
Unchecked IC50 = 2.66 nM 8.57 Cytotoxicity against human A2780R cells assessed as reduction in cell growth mea... 30818177

Literature References

PubMed DOI Target Context # Activities
32339853 10.1016/j.ejmech.2020.112308 K562 9
32339853 10.1016/j.ejmech.2020.112308 Unchecked 7
34171660 10.1016/j.ejmech.2021.113656 ADMET 6
30525602 10.1021/acs.jmedchem.8b01386 Unchecked 5
28792756 10.1021/acs.jmedchem.7b00480 Unchecked 5
28792756 10.1021/acs.jmedchem.7b00480 Liver 5
19530698 10.1021/jm900321u K562 4
35797900 10.1016/j.ejmech.2022.114573 ADMET 4
30525602 10.1021/acs.jmedchem.8b01386 Cytochrome P450 4
30004697 10.1021/acs.jmedchem.8b00050 Unchecked 3
32339853 10.1016/j.ejmech.2020.112308 H22 3
30004697 10.1021/acs.jmedchem.8b00050 No relevant target 2
30525602 10.1021/acs.jmedchem.8b01386 ADMET 2
33038796 10.1016/j.ejmech.2020.112873 Unchecked 2
30525602 10.1021/acs.jmedchem.8b01386 No relevant target 2
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 11 2
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 8 2
30004697 10.1021/acs.jmedchem.8b00050 HT-29 2
30818177 10.1016/j.ejmech.2019.02.038 Unchecked 2
25528337 10.1016/j.ejmech.2014.12.024 NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine