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Compound Detail

CHEMBL330407

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COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)cc1N
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL330407
Phase Preclinical
Structure Type MOL
InChI Key QSAMWSFELUCKOA-WAYWQWQTSA-N
28
Targets
63
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

315.4
MW (Da)
3.47
ALogP
5
HBA
1
HBD
62.9
PSA (Ų)
0.65
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 C18H21NO4
MW 315.37
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness 0.31

Activity Summary

IC50 63 meas. best 9.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HeLa
CHEMBL399
 IC50 9.28 8.2125 0.5 4
Colon 26
CHEMBL614466
 IC50 8.55 8.42 2.8 2
HCT-116
CHEMBL394
 IC50 8.5 7.8567 3.2 3
MCF7
CHEMBL387
 IC50 8.46 8.22 3.5 3
HL-60
CHEMBL383
 IC50 8.35 8.135 4.5 4
KB
CHEMBL398
 IC50 8.32 8.17 4.8 4
NCI-H460
CHEMBL396
 IC50 8.31 8.18 4.9 2
HT-29
CHEMBL384
 IC50 8.3 8.004 5.0 5
Mus musculus
CHEMBL375
 IC50 8.29 8.29 5.1 1
MKN-45
CHEMBL614354
 IC50 8.29 8.29 5.1 1
U2OS
CHEMBL615023
 IC50 8.22 8.22 6.0 1
HEK293
CHEMBL614818
 IC50 8.15 8.15 7.1 2
TSGH 9201
CHEMBL614787
 IC50 8.15 8.15 7.0 1
TSGH
CHEMBL615018
 IC50 8.11 8.11 7.7 1
Unchecked
CHEMBL612545
 IC50 8.04 6.735 9.2 4
HUVEC
CHEMBL613979
 IC50 7.95 7.95 11.3 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.92 7.0933 12.0 3
MDA-MB-231
CHEMBL400
 IC50 7.92 7.635 12.0 2
HMEC-1
CHEMBL4296433
 IC50 7.92 7.92 12.0 3
K562
CHEMBL385
 IC50 7.8 7.36 15.7 2
CEM-DNR
CHEMBL614547
 IC50 7.8 7.8 15.7 1
HepG2
CHEMBL395
 IC50 7.55 7.55 28.0 1
HCT-15
CHEMBL612263
 IC50 7.34 7.34 45.2 1
A549
CHEMBL392
 IC50 7.29 7.05 51.2 3
CCRF-CEM
CHEMBL382
 IC50 7.29 7.29 51.2 1
BJ
CHEMBL614358
 IC50 7.06 7.06 87.3 1
Tubulin
CHEMBL2094134
 IC50 6.52 5.9467 300.0 3
Tubulin
CHEMBL2095182
 IC50 5.92 5.5033 1200.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HeLa IC50 = 0.53 nM 9.28 Cytotoxicity against human HeLa cells by MTT assay 19879758
HeLa IC50 = 2.6 nM 8.59 Antiproliferative activity against human HeLa cells after 2 days by MTT assay 29432949
HeLa IC50 = 2.6 nM 8.59 Antiproliferative activity against human HeLa cells by MTT assay 30502686
Colon 26 IC50 = 2.8 nM 8.55 Antiproliferative activity against mouse Colon 26 cells assessed as inhibition o... 23454513
HCT-116 IC50 = 3.17 nM 8.5 Cytotoxicity against p53 deficient human HCT116 cells assessed as reduction in c... 31401010
HCT-116 IC50 = 3.18 nM 8.5 Cytotoxicity against human HCT116 cells assessed as reduction in cell viability ... 31401010
MCF7 IC50 = 3.5 nM 8.46 Cytotoxicity against human MCF7 cells by MTT assay 19879758
HL-60 IC50 = 4.5 nM 8.35 Antiproliferative activity against human HL60 cells after 2 days by MTT assay 29432949
HL-60 IC50 = 4.5 nM 8.35 Antiproliferative activity against human HL60 cells by MTT assay 30502686
KB IC50 = 4.8 nM 8.32 Antiproliferative activity against human KB-VIN10 cell line by methylene blue dy... 17034147
NCI-H460 IC50 = 4.9 nM 8.31 Cytotoxic activity against human NCI-H460 cells after 72 hrs by sulforhodamine B... 18396857
HT-29 IC50 = 5.0 nM 8.3 Antiproliferative activity against human HT29 cell line by methylene blue dye as... 17034147
HT-29 IC50 = 5.0 nM 8.3 Cytotoxic activity against human HT29 cells after 72 hrs by sulforhodamine B tes... 18396857
Colon 26 IC50 = 5.1 nM 8.29 Growth inhibition of colon 26 adenocarcinoma cells by 50 %. 9685242
Mus musculus IC50 = 5.1 nM 8.29 Inhibitory activity against murine colon 26 adenocarcinoma cell 12570374
MKN-45 IC50 = 5.1 nM 8.29 Antiproliferative activity against human MKN45 cell line by methylene blue dye a... 17034147
U2OS IC50 = 6.0 nM 8.22 Cytotoxicity against human U2OS cells assessed as reduction in cell viability in... 31401010
KB IC50 = 7.0 nM 8.15 Antiproliferative activity against human KB cell line by methylene blue dye assa... 17034147
HEK293 IC50 = 7.1 nM 8.15 Antiproliferative activity against HEK293 cells by MTT assay 30502686
TSGH 9201 IC50 = 7.0 nM 8.15 Antiproliferative activity against human TSGH stomach carcinoma cell line by met... 17034147

Literature References

PubMed DOI Target Context # Activities
31401010 10.1016/j.bmc.2019.07.048 CCRF-CEM 15
29432949 10.1016/j.ejmech.2018.01.058 A549 8
30502686 10.1016/j.ejmech.2018.11.023 A549 7
31401010 10.1016/j.bmc.2019.07.048 Unchecked 5
29432949 10.1016/j.ejmech.2018.01.058 Unchecked 4
31401010 10.1016/j.bmc.2019.07.048 Tubulin 4
20363626 10.1016/j.bmcl.2010.03.066 Saccharomyces cerevisiae 3
30502686 10.1016/j.ejmech.2018.11.023 HMEC-1 3
26852340 10.1016/j.bmc.2016.01.007 Tubulin 3
31413794 10.1021/acsmedchemlett.9b00058 Huh-7 3
31413794 10.1021/acsmedchemlett.9b00058 HeLa 3
31401010 10.1016/j.bmc.2019.07.048 HCT-116 2
17034147 10.1021/jm060616k KB 2
15139768 10.1021/jm0305974 KB 2
26852340 10.1016/j.bmc.2016.01.007 NON-PROTEIN TARGET 2
29432949 10.1016/j.ejmech.2018.01.058 HMEC-1 2
15943482 10.1021/jm0205797 SW-1736 1
15943482 10.1021/jm0205797 NCI-H460 1
15943482 10.1021/jm0205797 DU-145 1
15139768 10.1021/jm0305974 Tubulin 1

Data from ChEMBL 36 via Core Engine