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Compound Detail

CHEMBL5560224

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COc1cc(-n2cnc3ccc(-c4ccc(C)c(N)c4)nc32)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5560224
Phase Preclinical
Structure Type MOL
InChI Key WAGLVYSVXYGSOH-UHFFFAOYSA-N
17
Targets
19
Activities
2
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

390.4
MW (Da)
4.00
ALogP
7
HBA
1
HBD
84.4
PSA (Ų)
0.52
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22N4O3
MW 390.44
Aromatic Rings 4
Heavy Atoms 29
NP-Likeness -0.92

Activity Summary

IC50 18 meas. best 9.3
Kd 1 meas. best 5.74

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MGC-803
CHEMBL3706566
 IC50 9.3 9.3 0.5 1
SK-OV-3
CHEMBL614925
 IC50 9.1 9.1 0.8 1
HeLa
CHEMBL399
 IC50 9.05 9.05 0.9 1
MCF7
CHEMBL387
 IC50 9.0 9.0 1.0 1
A549
CHEMBL392
 IC50 9.0 9.0 1.0 1
A549/TR
CHEMBL4483226
 IC50 8.8 8.8 1.6 1
Unchecked
CHEMBL612545
 IC50 8.7 7.5933 2.0 3
HCT-116
CHEMBL394
 IC50 8.52 8.52 3.0 1
A2780
CHEMBL614004
 IC50 8.52 8.52 3.0 1
PANC-1
CHEMBL614139
 IC50 8.4 8.4 4.0 1
DU-145
CHEMBL613508
 IC50 8.4 8.4 4.0 1
A2780/Taxol
CHEMBL4483224
 IC50 8.32 8.32 4.8 1
MDA-MB-468
CHEMBL614335
 IC50 8.0 8.0 10.0 1
HT-29
CHEMBL384
 IC50 7.96 7.96 11.0 1
U-87 MG
CHEMBL614247
 IC50 7.82 7.82 15.0 1
MDA-MB-231
CHEMBL400
 IC50 7.7 7.7 20.0 1
Katanin p60 ATPase-containing subunit A1
CHEMBL3879856
 Kd 5.74 5.74 1815.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 666.0 ng.hr.mL-1 Mus musculus
AUC 668.0 ng.hr.mL-1 Mus musculus
AUC 1241.0 ng.hr.mL-1 Mus musculus
AUC 1335.0 ng.hr.mL-1 Mus musculus
Cmax 1.653 ug.mL-1 Mus musculus
Cmax 1.196 ug.mL-1 Mus musculus
F 40.0 % Mus musculus
MRT 0.52 hr Mus musculus
MRT 2.47 hr Mus musculus
T1/2 39.0 hr Mus musculus
T1/2 1.06 hr Mus musculus
T1/2 1.92 hr Mus musculus
Tmax 0.08 hr Mus musculus
Tmax 0.14 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MGC-803 IC50 = 0.5 nM 9.3 Antiproliferative activity against human MGC-803 assessed as inhibition of cell ... 38996194
SK-OV-3 IC50 = 0.8 nM 9.1 Antiproliferative activity against human SK-OV-3 cells assessed as inhibition of... 38996194
HeLa IC50 = 0.9 nM 9.05 Antiproliferative activity against human HeLa assessed as inhibition of cell gro... 38996194
MCF7 IC50 = 1.0 nM 9.0 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 38996194
A549 IC50 = 1.0 nM 9.0 Antiproliferative activity against human A549 assessed as inhibition of cell gro... 38996194
A549/TR IC50 = 1.6 nM 8.8 Antiproliferative activity against paclitaxel resistant human A549/Taxol cells a... 38996194
Unchecked IC50 = 2.0 nM 8.7 Antiproliferative activity against human CDDP-resistant A549 cell assessed as in... 38996194
HCT-116 IC50 = 3.0 nM 8.52 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 38996194
A2780 IC50 = 3.0 nM 8.52 Antiproliferative activity against human A2780 cells assessed as inhibition of c... 38996194
DU-145 IC50 = 4.0 nM 8.4 Antiproliferative activity against human DU-145 assessed as inhibition of cell g... 38996194
PANC-1 IC50 = 4.0 nM 8.4 Antiproliferative activity against human PANC-1 assessed as inhibition of cell g... 38996194
Unchecked IC50 = 4.2 nM 8.38 Antiproliferative activity against cisplatin resistant human A2780/CDDP cells as... 38996194
A2780/Taxol IC50 = 4.8 nM 8.32 Antiproliferative activity against paclitaxel resistant human A2780/Taxol cells ... 38996194
MDA-MB-468 IC50 = 10.0 nM 8.0 Antiproliferative activity against human MDA-MB-468 cells assessed as inhibition... 38996194
HT-29 IC50 = 11.0 nM 7.96 Antiproliferative activity against human HT-29 cells assessed as inhibition of c... 38996194
U-87 MG IC50 = 15.0 nM 7.82 Antiproliferative activity against human U-87 MG assessed as inhibition of cell ... 38996194
MDA-MB-231 IC50 = 20.0 nM 7.7 Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition... 38996194
Katanin p60 ATPase-containing subunit A1 Kd = 1815.0 nM 5.74 Binding affinity to N-terminal human Katanin p60 (8 to 229 residues) expressed i... 38996194
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of porcine brain tubulin polymerization 38996194

Literature References

PubMed DOI Target Context # Activities
38996194 10.1021/acs.jmedchem.4c00878 ADMET 43
38996194 10.1021/acs.jmedchem.4c00878 MCF7 20
38996194 10.1021/acs.jmedchem.4c00878 Unchecked 14
38996194 10.1021/acs.jmedchem.4c00878 MDA-MB-231 8
38996194 10.1021/acs.jmedchem.4c00878 Katanin p60 ATPase-containing subunit A1 3
38996194 10.1021/acs.jmedchem.4c00878 HUVEC 3
38996194 10.1021/acs.jmedchem.4c00878 Tubulin 2
38996194 10.1021/acs.jmedchem.4c00878 A549/TR 2
38996194 10.1021/acs.jmedchem.4c00878 No relevant target 1
38996194 10.1021/acs.jmedchem.4c00878 A2780/Taxol 1
38996194 10.1021/acs.jmedchem.4c00878 MGC-803 1
38996194 10.1021/acs.jmedchem.4c00878 U-87 MG 1
38996194 10.1021/acs.jmedchem.4c00878 A549 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

Data from ChEMBL 36 via Core Engine