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Compound Detail

CHEMBL4561563

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COc1ccc(-c2cc3c([nH]c(=O)n3-c3cc(OC)c(OC)c(OC)c3)c(C(N)=O)n2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4561563
Phase Preclinical
Structure Type MOL
InChI Key WUZIEGHVPAZRFN-UHFFFAOYSA-N
13
Targets
15
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

466.4
MW (Da)
2.22
ALogP
9
HBA
3
HBD
150.9
PSA (Ų)
0.38
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H22N4O7
MW 466.45
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -0.44

Activity Summary

IC50 13 meas. best 6.77
Kd 2 meas. best 5.04

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HCT-116
CHEMBL394
 IC50 6.77 6.77 170.0 1
A2780
CHEMBL614004
 IC50 6.68 6.68 210.0 1
MDA-MB-468
CHEMBL614335
 IC50 6.65 6.65 222.0 1
SK-OV-3
CHEMBL614925
 IC50 6.61 6.61 248.0 1
HeLa
CHEMBL399
 IC50 6.6 6.6 250.0 1
A549
CHEMBL392
 IC50 6.47 6.2333 340.0 3
U-87 MG
CHEMBL614247
 IC50 6.25 6.25 558.0 1
MCF7
CHEMBL387
 IC50 6.09 6.09 813.0 1
PANC-1
CHEMBL614139
 IC50 5.77 5.77 1690.0 1
DU-145
CHEMBL613508
 IC50 5.67 5.67 2146.0 1
Tubulin
CHEMBL2111354
 IC50 5.08 5.08 8400.0 1
Katanin p60 ATPase-containing subunit A1
CHEMBL3879856
 Kd 5.04 5.04 9155.0 1
Unchecked
CHEMBL612545
 Kd 4.9 4.9 12700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2630.0 ng.hr.mL-1 Mus musculus
AUC 2950.0 ng.hr.mL-1 Mus musculus
Cmax 1243.43 nM Mus musculus
MRT 8.39 hr Mus musculus
T1/2 9.36 hr Mus musculus
Tmax 0.23 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HCT-116 IC50 = 170.0 nM 6.77 Antiproliferative activity against human HCT116 cells assessed as reduction in c... 31185410
A2780 IC50 = 210.0 nM 6.68 Antiproliferative activity against human A2780 cells assessed as reduction in ce... 31185410
MDA-MB-468 IC50 = 222.0 nM 6.65 Antiproliferative activity against human MDA-MB-468 cells assessed as inhibition... 38996194
SK-OV-3 IC50 = 248.0 nM 6.61 Antiproliferative activity against human SK-OV-3 cells assessed as inhibition of... 38996194
HeLa IC50 = 250.0 nM 6.6 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 31185410
A549 IC50 = 340.0 nM 6.47 Antiproliferative activity against human A549 cells harboring control siRNA afte... 31185410
A549 IC50 = 400.0 nM 6.4 Antiproliferative activity against human A549 cells assessed as reduction in cel... 31185410
U-87 MG IC50 = 558.0 nM 6.25 Antiproliferative activity against human U-87 MG assessed as inhibition of cell ... 38996194
MCF7 IC50 = 813.0 nM 6.09 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 38996194
A549 IC50 = 1480.0 nM 5.83 Antiproliferative activity against human A549 cells harboring katanin siRNA afte... 31185410
PANC-1 IC50 = 1690.0 nM 5.77 Antiproliferative activity against human PANC-1 assessed as inhibition of cell g... 38996194
DU-145 IC50 = 2146.0 nM 5.67 Antiproliferative activity against human DU-145 assessed as inhibition of cell g... 38996194
Tubulin IC50 = 8400.0 nM 5.08 Inhibition of pig brain tubulin polymerization measured every 1 min for 25 mins ... 31185410
Katanin p60 ATPase-containing subunit A1 Kd = 9155.0 nM 5.04 Binding affinity to N-terminal human Katanin p60 (8 to 229 residues) expressed i... 38996194
Unchecked Kd = 12700.0 nM 4.9 Binding affinity to human katanin by MST assay 31185410

Literature References

PubMed DOI Target Context # Activities
31185410 10.1016/j.ejmech.2019.05.072 A549 25
31185410 10.1016/j.ejmech.2019.05.072 ADMET 9
31185410 10.1016/j.ejmech.2019.05.072 A2780 3
31185410 10.1016/j.ejmech.2019.05.072 Tubulin 3
31185410 10.1016/j.ejmech.2019.05.072 HUVEC 3
38996194 10.1021/acs.jmedchem.4c00878 Katanin p60 ATPase-containing subunit A1 2
38996194 10.1021/acs.jmedchem.4c00878 MGC-803 1
38996194 10.1021/acs.jmedchem.4c00878 PANC-1 1
38996194 10.1021/acs.jmedchem.4c00878 DU-145 1
38996194 10.1021/acs.jmedchem.4c00878 HeLa 1
38996194 10.1021/acs.jmedchem.4c00878 SK-OV-3 1
38996194 10.1021/acs.jmedchem.4c00878 A2780 1
38996194 10.1021/acs.jmedchem.4c00878 HT-29 1
38996194 10.1021/acs.jmedchem.4c00878 HCT-116 1
38996194 10.1021/acs.jmedchem.4c00878 MDA-MB-231 1
38996194 10.1021/acs.jmedchem.4c00878 MDA-MB-468 1
38996194 10.1021/acs.jmedchem.4c00878 MCF7 1
31185410 10.1016/j.ejmech.2019.05.072 Katanin p60 ATPase-containing subunit A1 1
31185410 10.1016/j.ejmech.2019.05.072 Unchecked 1
31185410 10.1016/j.ejmech.2019.05.072 HCT-116 1

Data from ChEMBL 36 via Core Engine