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Compound Detail

CHEMBL376130

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COc1ccc2c(c1N)C(=O)O[C@@H]2[C@H]1c2c(cc3c(c2OC)OCO3)CCN1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL376130
Phase Preclinical
Structure Type MOL
InChI Key WPUKOXIOPURGHT-MSOLQXFVSA-N
13
Targets
20
Activities
2
Assay Types
5
PK Parameters
18
Publications
0
Known Names

Molecular Properties

398.4
MW (Da)
2.46
ALogP
8
HBA
1
HBD
92.5
PSA (Ų)
0.62
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22N2O6
MW 398.42
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness 1.41

Activity Summary

IC50 15 meas. best 7.22
EC50 5 meas. best 7.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NIH3T3
CHEMBL614822
 EC50 7.3 7.3 50.0 1
SNU-387
CHEMBL1075583
 IC50 7.22 7.22 59.5 1
Bel-7402
CHEMBL614279
 IC50 7.11 7.11 78.4 1
A549
CHEMBL392
 EC50 7.08 7.045 84.0 2
SNU-398
CHEMBL614454
 IC50 7.03 6.76 94.3 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.97 6.5667 106.9 6
SMMC-7721
CHEMBL613831
 IC50 6.96 6.96 109.3 1
Huh-7
CHEMBL614039
 IC50 6.66 6.66 218.4 1
SNU-423
CHEMBL1075584
 IC50 6.65 6.65 226.1 1
SNU-449
CHEMBL1075585
 IC50 6.55 6.55 283.4 1
Tubulin
CHEMBL2095182
 EC50 6.52 6.52 300.0 1
SNU-475
CHEMBL1075586
 IC50 6.23 6.23 584.5 1
Unchecked
CHEMBL612545
 EC50 5.92 5.92 1200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 350.0 ng.hr.mL-1 Mus musculus
AUC 391.0 ng.hr.mL-1 Mus musculus
CL 95.3 mL.min-1.kg-1 Mus musculus
F 11.4 % Mus musculus
T1/2 1.043 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NIH3T3 EC50 = 50.0 nM 7.3 Effect on cell growth in dividing Swiss 3T3 cells by MTS assay 16279766
SNU-387 IC50 = 59.5 nM 7.22 Antiproliferative activity against human SNU387 after 72 hrs by CellTiter Glo as... 22320354
Bel-7402 IC50 = 78.4 nM 7.11 Antiproliferative activity against human Bel7402 after 72 hrs by CellTiter Glo a... 22320354
A549 EC50 = 84.0 nM 7.08 Effect on cell growth in A549 cells by colony-forming assay 16279766
SNU-398 IC50 = 94.3 nM 7.03 Antiproliferative activity against human SNU398 cells 22320354
A549 EC50 = 97.0 nM 7.01 Effect on cell growth in A549 cells by MTS assay 16279766
NON-PROTEIN TARGET IC50 = 106.9 nM 6.97 Antiproliferative activity against human JHH4 after 72 hrs by CellTiter Glo assa... 22320354
SMMC-7721 IC50 = 109.3 nM 6.96 Antiproliferative activity against human SMMC7721 after 72 hrs by CellTiter Glo ... 22320354
Huh-7 IC50 = 218.4 nM 6.66 Antiproliferative activity against human HuH7 after 72 hrs by CellTiter Glo assa... 22320354
SNU-423 IC50 = 226.1 nM 6.65 Antiproliferative activity against human SNU423 after 72 hrs by CellTiter Glo as... 22320354
NON-PROTEIN TARGET IC50 = 237.4 nM 6.62 Antiproliferative activity against human PLC/PRF/5 cells 22320354
NON-PROTEIN TARGET IC50 = 277.8 nM 6.56 Antiproliferative activity against human PLC/PRF/5 after 72 hrs by CellTiter Glo... 22320354
SNU-449 IC50 = 283.4 nM 6.55 Antiproliferative activity against human SNU449 after 72 hrs by CellTiter Glo as... 22320354
Tubulin EC50 = 300.0 nM 6.52 Inhibition of tubulin polymerization 16279766
NON-PROTEIN TARGET IC50 = 318.0 nM 6.5 Antiproliferative activity against human JHH7 after 72 hrs by CellTiter Glo assa... 22320354
SNU-398 IC50 = 323.5 nM 6.49 Antiproliferative activity against human SNU398 after 72 hrs by CellTiter Glo as... 22320354
NON-PROTEIN TARGET IC50 = 351.0 nM 6.46 Antiproliferative activity against human MHCC97H after 72 hrs by CellTiter Glo a... 22320354
NON-PROTEIN TARGET IC50 = 508.1 nM 6.29 Antiproliferative activity against human SNU182 after 72 hrs by CellTiter Glo as... 22320354
SNU-475 IC50 = 584.5 nM 6.23 Antiproliferative activity against human SNU475 after 72 hrs by CellTiter Glo as... 22320354
Unchecked EC50 = 1200.0 nM 5.92 Inhibition of calf brain tubulin assembly 22320354

Literature References

PubMed DOI Target Context # Activities
22320354 10.1021/jm200848t Unchecked 15
22320354 10.1021/jm200848t NON-PROTEIN TARGET 8
16279766 10.1021/jm050674q Mus musculus 6
22320354 10.1021/jm200848t SNU-398 5
22320354 10.1021/jm200848t Molecular identity unknown 3
16279766 10.1021/jm050674q Molecular identity unknown 3
22320354 10.1021/jm200848t ADMET 2
16279766 10.1021/jm050674q A549 2
16279766 10.1021/jm050674q NIH3T3 2
22320354 10.1021/jm200848t Bel-7402 1
22320354 10.1021/jm200848t SNU-475 1
22320354 10.1021/jm200848t SNU-449 1
22320354 10.1021/jm200848t SNU-423 1
22320354 10.1021/jm200848t SNU-387 1
22320354 10.1021/jm200848t Huh-7 1
22320354 10.1021/jm200848t HepG2 1
22320354 10.1021/jm200848t SMMC-7721 1
16279766 10.1021/jm050674q Tubulin 1

Data from ChEMBL 36 via Core Engine