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Compound Detail

CHEMBL374257

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COc1cc(C(=O)c2n[nH]c3c(C#CCO)c(OC)ccc23)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL374257
Phase Preclinical
Structure Type MOL
InChI Key KEEGEWFDKNKLJX-UHFFFAOYSA-N
11
Targets
14
Activities
1
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

396.4
MW (Da)
2.17
ALogP
7
HBA
2
HBD
102.9
PSA (Ų)
0.49
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 C21H20N2O6
MW 396.40
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.01

Activity Summary

IC50 14 meas. best 9.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HeLa
CHEMBL399
 IC50 9.1 9.1 0.8 1
HT-29
CHEMBL384
 IC50 9.0 9.0 1.0 1
PC-3
CHEMBL390
 IC50 9.0 9.0 1.0 1
ACHN
CHEMBL614519
 IC50 8.8 8.8 1.6 1
NCI-H69
CHEMBL614805
 IC50 8.8 8.8 1.6 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.77 8.755 1.7 2
HCT-15
CHEMBL612263
 IC50 8.72 8.72 1.9 1
H69AR
CHEMBL5209893
 IC50 8.59 8.59 2.6 1
NCI-H460
CHEMBL396
 IC50 8.1 8.1 8.0 1
Tubulin
CHEMBL2095182
 IC50 7.34 6.98 46.0 2
Unchecked
CHEMBL612545
 IC50 6.3 5.76 500.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HeLa IC50 = 0.8 nM 9.1 Cytotoxicity against human HeLa cells 17286393
HT-29 IC50 = 1.0 nM 9.0 Cytotoxicity against human HT29 cells 17286393
PC-3 IC50 = 1.0 nM 9.0 Cytotoxicity against human PC3 cells 17286393
ACHN IC50 = 1.6 nM 8.8 Antiproliferative activity against drug resistant ACHN cell line expressing MDR1... 17286393
NCI-H69 IC50 = 1.6 nM 8.8 Antiproliferative activity against drug sensitive NCI-H69 cell line by Alamar Bl... 17286393
NON-PROTEIN TARGET IC50 = 1.7 nM 8.77 Antiproliferative activity against drug sensitive Messa cell line by Alamar Blue... 17286393
NON-PROTEIN TARGET IC50 = 1.8 nM 8.74 Antiproliferative activity against drug resistant Messa/DX5 cell line expressing... 17286393
HCT-15 IC50 = 1.9 nM 8.72 Antiproliferative activity against drug resistant HCT15 cell line expressing MDR... 17286393
H69AR IC50 = 2.6 nM 8.59 Antiproliferative activity against drug resistant H69AR cell line expressing MRP... 17286393
NCI-H460 IC50 = 8.0 nM 8.1 Inhibition of proliferation of human H460 cells 17286393
Tubulin IC50 = 46.0 nM 7.34 Displacement of [3H]colchicine from tubulin in MCF7 cells 17286393
Tubulin IC50 = 240.0 nM 6.62 Displacement of [3H]colchicine from tubulin in HeLa cells 17286393
Unchecked IC50 = 500.0 nM 6.3 Displacement of [3H]colchicine from tubulin in bovine brain at 500 nM 17286393
Unchecked IC50 = 6000.0 nM 5.22 Inhibition of bovine tubulin polymerization 17286393

Literature References

PubMed DOI Target Context # Activities
17286393 10.1021/jm061348t Unchecked 3
17286393 10.1021/jm061348t NON-PROTEIN TARGET 2
17286393 10.1021/jm061348t Tubulin 2
17286393 10.1021/jm061348t NCI-H460 1
17286393 10.1021/jm061348t HT-29 1
17286393 10.1021/jm061348t PC-3 1
17286393 10.1021/jm061348t HeLa 1
17286393 10.1021/jm061348t HCT-15 1
17286393 10.1021/jm061348t ACHN 1
17286393 10.1021/jm061348t NCI-H69 1
17286393 10.1021/jm061348t H69AR 1

Data from ChEMBL 36 via Core Engine