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Compound Detail

CHEMBL311636

8Z-3,4',5-TRIMETHOXYSTILBENE
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COc1ccc(/C=C\c2cc(OC)cc(OC)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL311636
Name 8Z-3,4',5-TRIMETHOXYSTILBENE
Phase Preclinical
Structure Type MOL
InChI Key GDHNBPHYVRHYCC-PLNGDYQASA-N
20
Targets
28
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

270.3
MW (Da)
3.88
ALogP
3
HBA
0
HBD
27.7
PSA (Ų)
0.77
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C17H18O3
MW 270.33
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.05

Activity Summary

IC50 23 meas. best 7.4
Ki 5 meas. best 7.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aryl hydrocarbon receptor
CHEMBL3201
 Ki 7.92 7.92 12.0 1
HT-29
CHEMBL384
 IC50 7.4 7.2033 40.0 3
Aryl hydrocarbon receptor
CHEMBL4725
 Ki 7.12 7.12 75.0 1
Caco-2
CHEMBL614058
 IC50 7.1 6.97 80.0 2
MCF7
CHEMBL387
 IC50 6.92 6.92 120.0 1
Estrogen receptor
CHEMBL206
 Ki 6.88 6.88 132.0 1
HL-60
CHEMBL383
 IC50 6.82 6.82 150.0 1
MKN-45
CHEMBL614354
 IC50 6.66 6.66 218.0 1
HCT-116
CHEMBL394
 IC50 6.66 6.66 220.0 1
KB
CHEMBL398
 IC50 6.65 6.6 223.0 2
ADMET
CHEMBL612558
 IC50 6.64 6.64 230.0 1
NCI-H460
CHEMBL396
 IC50 6.6 6.6 253.0 1
SW480
CHEMBL612544
 IC50 6.52 6.52 300.0 2
TSGH 9201
CHEMBL614787
 IC50 6.49 6.49 324.0 1
HepG2
CHEMBL395
 IC50 6.33 6.33 473.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.23 6.23 590.0 1
B16-F10
CHEMBL612656
 IC50 6.0 6.0 1000.0 1
Tubulin
CHEMBL2094134
 IC50 5.75 5.75 1800.0 1
Tubulin
CHEMBL2095182
 IC50 5.46 5.44 3500.0 2
Bos taurus
CHEMBL613489
 IC50 5.42 5.42 3800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aryl hydrocarbon receptor Ki = 12.0 nM 7.92 Binding affinity to aryl hydrocarbon receptor (unknown origin) -
HT-29 IC50 = 40.0 nM 7.4 Cytotoxicity against human HT-29 cells after 3 days by [3H]thymidine incorporati... 20627379
HT-29 IC50 = 54.0 nM 7.27 Antiproliferative activity against human HT29 cell line by methylene blue dye as... 17034147
Aryl hydrocarbon receptor Ki = 75.0 nM 7.12 Binding affinity for aryl hydrocarbon receptor (AhR) of rabbit liver cytosol inc... 15634023
Caco-2 IC50 = 80.0 nM 7.1 Cytotoxicity against human Caco-2 cells after 3 days by [3H]thymidine incorporat... 20627379
HT-29 IC50 = 115.0 nM 6.94 Anti cancer activity against human HT-29 cell assessed as cell growth inhibition... 32485531
MCF7 IC50 = 120.0 nM 6.92 Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay 21215623
Estrogen receptor Ki = 132.0 nM 6.88 Binding affinity for estrogen receptor (ER) alpha of MCF-7 cell cytosol incubate... 15634023
Caco-2 IC50 = 145.0 nM 6.84 Anti cancer activity against human Caco-2 cell assessed as cell growth inhibitio... 32485531
HL-60 IC50 = 150.0 nM 6.82 Antiproliferative activity against human HL60 cells 16580204
HCT-116 IC50 = 220.0 nM 6.66 Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay 21215623
MKN-45 IC50 = 218.0 nM 6.66 Antiproliferative activity against human MKN45 cell line by methylene blue dye a... 17034147
KB IC50 = 223.0 nM 6.65 Antiproliferative activity against human KB-VIN10 cell line by methylene blue dy... 17034147
ADMET IC50 = 230.0 nM 6.64 Cytotoxicity against human IMR90 cells after 24 hrs by MTT assay 21215623
NCI-H460 IC50 = 253.0 nM 6.6 Antiproliferative activity against human H460 cell line by methylene blue dye as... 17034147
KB IC50 = 280.0 nM 6.55 Antiproliferative activity against human KB cell line by methylene blue dye assa... 17034147
SW480 IC50 = 300.0 nM 6.52 Antiproliferative activity against human SW480 cells assessed as cell viability ... 20395019
SW480 IC50 = 300.0 nM 6.52 Antiproliferative activity against human SW480 cells assessed as cell viability ... 20395019
TSGH 9201 IC50 = 324.0 nM 6.49 Antiproliferative activity against human TSGH stomach carcinoma cell line by met... 17034147
HepG2 IC50 = 473.0 nM 6.33 Anti cancer activity against human HepG2 cell assessed as cell growth inhibition... 32485531

Literature References

PubMed DOI Target Context # Activities
20395019 10.1016/j.ejmech.2010.03.024 SW480 16
16580204 10.1016/j.bmcl.2006.03.028 HL-60 6
12036362 10.1021/jm010119y Tubulin 3
20627379 10.1016/j.ejmech.2010.05.019 HT-29 3
21215623 10.1016/j.bmcl.2010.12.029 MCF7 2
32485531 10.1016/j.ejmech.2020.112356 B16-F10 2
17034147 10.1021/jm060616k Tubulin 2
21215623 10.1016/j.bmcl.2010.12.029 ADMET 2
17034147 10.1021/jm060616k KB 2
- 10.1007/s00044-009-9236-2 Aryl hydrocarbon receptor 2
12036362 10.1021/jm010119y DU-145 1
32485531 10.1016/j.ejmech.2020.112356 MDA-MB-231 1
12036362 10.1021/jm010119y Staphylococcus aureus 1
12036362 10.1021/jm010119y Candida albicans 1
12036362 10.1021/jm010119y Cryptococcus neoformans 1
12036362 10.1021/jm010119y SF-268 1
12036362 10.1021/jm010119y BXPC-3 1
1613753 10.1021/jm00090a021 Bos taurus 1
1613753 10.1021/jm00090a021 MLM 1
1613753 10.1021/jm00090a021 HT-29 1

Data from ChEMBL 36 via Core Engine