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Compound Detail

CHEMBL4468642

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COc1cc(C(=O)c2cccc(-c3ccc(C)c(O)c3)n2)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4468642
Phase Preclinical
Structure Type MOL
InChI Key BTWMVPMEPRQKQD-UHFFFAOYSA-N
10
Targets
19
Activities
2
Assay Types
4
PK Parameters
19
Publications
0
Known Names

Molecular Properties

379.4
MW (Da)
4.02
ALogP
6
HBA
1
HBD
77.9
PSA (Ų)
0.65
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H21NO5
MW 379.41
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.10

Activity Summary

IC50 18 meas. best 9.05
Kd 1 meas. best 5.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
M14
CHEMBL614317
 IC50 9.05 8.875 0.9 2
MDA-MB-453
CHEMBL614334
 IC50 8.96 8.94 1.1 2
Unchecked
CHEMBL612545
 IC50 8.85 8.6667 1.4 3
A-375
CHEMBL613859
 IC50 8.82 8.76 1.5 2
PC-3
CHEMBL390
 IC50 8.77 8.77 1.7 1
MDA-MB-231
CHEMBL400
 IC50 8.77 8.625 1.7 2
RPMI-7951
CHEMBL612447
 IC50 8.77 8.66 1.7 2
SK-BR-3
CHEMBL613834
 IC50 8.55 8.47 2.8 2
DU-145
CHEMBL613508
 IC50 8.43 8.43 3.7 1
Tubulin
CHEMBL2111354
 Kd 5.58 5.58 2660.0 1
Tubulin
CHEMBL2111354
 IC50 5.3 5.3 5000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 116.4 mL.min-1.kg-1 Homo sapiens
CL 57.3 mL.min-1.kg-1 Mus musculus
T1/2 0.18 hr Homo sapiens
T1/2 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
M14 IC50 = 0.9 nM 9.05 Antiproliferative activity against human M14 cells measured after 72 hrs by MTS ... 31860298
MDA-MB-453 IC50 = 1.1 nM 8.96 Antiproliferative activity against human MDA-MB-453 cells assessed as cell growt... 34378386
MDA-MB-453 IC50 = 1.2 nM 8.92 Antiproliferative activity against human MDA-MB-453 cells measured after 72 hrs ... 31860298
Unchecked IC50 = 1.4 nM 8.85 Antiproliferative activity against human M14/LCC6MDR1 cells measured after 72 hr... 31860298
A-375 IC50 = 1.5 nM 8.82 Antiproliferative activity against human A375 cells measured after 72 hrs by MTS... 31860298
MDA-MB-231 IC50 = 1.7 nM 8.77 Antiproliferative activity against human MDA-MB-231 cells measured after 72 hrs ... 31860298
RPMI-7951 IC50 = 1.7 nM 8.77 Antiproliferative activity against human RPMI7951 cells measured after 72 hrs by... 31860298
PC-3 IC50 = 1.7 nM 8.77 Antiproliferative activity against human PC3 cells measured after 72 hrs by MTS ... 31860298
M14 IC50 = 2.0 nM 8.7 Antiproliferative activity against human M14 cells assessed as cell growth inhib... 34378386
A-375 IC50 = 2.0 nM 8.7 Antiproliferative activity against human A-375 cells assessed as cell growth inh... 34378386
Unchecked IC50 = 2.5 nM 8.6 Antiproliferative activity against human PC3/TxR cells measured after 72 hrs by ... 31860298
SK-BR-3 IC50 = 2.8 nM 8.55 Antiproliferative activity against human SK-BR-3 cells measured after 72 hrs by ... 31860298
Unchecked IC50 = 2.8 nM 8.55 Antiproliferative activity against human DU145-TxR cells measured after 72 hrs b... 31860298
RPMI-7951 IC50 = 2.8 nM 8.55 Antiproliferative activity against human RPMI-7951 cells assessed as cell growth... 34378386
MDA-MB-231 IC50 = 3.3 nM 8.48 Antiproliferative activity against human MDA-MB-231 cells assessed as cell growt... 34378386
DU-145 IC50 = 3.7 nM 8.43 Antiproliferative activity against human DU145 cells measured after 72 hrs by MT... 31860298
SK-BR-3 IC50 = 4.1 nM 8.39 Antiproliferative activity against human SK-BR-3 cells assessed as cell growth i... 34378386
Tubulin Kd = 2660.0 nM 5.58 Binding affinity to porcine brain tubulin polymerization by surface plasmon anal... 31860298
Tubulin IC50 = 5000.0 nM 5.3 Inhibition of porcine brain tubulin polymerization measured at 30 secs interval ... 31860298

Literature References

PubMed DOI Target Context # Activities
31860298 10.1021/acs.jmedchem.9b01815 A-375 11
31860298 10.1021/acs.jmedchem.9b01815 Unchecked 6
31860298 10.1021/acs.jmedchem.9b01815 Tubulin 5
34378386 10.1021/acs.jmedchem.1c00715 ADMET 4
34378386 10.1021/acs.jmedchem.1c00715 Unchecked 1
31860298 10.1021/acs.jmedchem.9b01815 MDA-MB-231 1
34378386 10.1021/acs.jmedchem.1c00715 RPMI-7951 1
34378386 10.1021/acs.jmedchem.1c00715 M14 1
34378386 10.1021/acs.jmedchem.1c00715 A-375 1
34378386 10.1021/acs.jmedchem.1c00715 SK-BR-3 1
34378386 10.1021/acs.jmedchem.1c00715 MDA-MB-453 1
34378386 10.1021/acs.jmedchem.1c00715 MDA-MB-231 1
31860298 10.1021/acs.jmedchem.9b01815 ADMET 1
31860298 10.1021/acs.jmedchem.9b01815 DU-145 1
31860298 10.1021/acs.jmedchem.9b01815 PC-3 1
31860298 10.1021/acs.jmedchem.9b01815 RPMI-7951 1
31860298 10.1021/acs.jmedchem.9b01815 M14 1
31860298 10.1021/acs.jmedchem.9b01815 SK-BR-3 1
31860298 10.1021/acs.jmedchem.9b01815 MDA-MB-453 1

Data from ChEMBL 36 via Core Engine