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Compound Detail

CHEMBL5081479

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COc1cc(C(=O)c2nc(-c3ccc(C)c(O)c3)ccc2F)cc(OC)c1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5081479
Phase Preclinical
Structure Type MOL
InChI Key JZHPUOFRNWNYQR-UHFFFAOYSA-N
7
Targets
12
Activities
1
Assay Types
8
PK Parameters
17
Publications
0
Known Names

Molecular Properties

397.4
MW (Da)
4.16
ALogP
6
HBA
1
HBD
77.9
PSA (Ų)
0.63
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 C22H20FNO5
MW 397.40
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.29

Activity Summary

IC50 12 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-453
CHEMBL614334
 IC50 8.85 8.85 1.4 1
A-375
CHEMBL613859
 IC50 8.74 8.515 1.8 2
M14
CHEMBL614317
 IC50 8.72 8.5267 1.9 3
Unchecked
CHEMBL612545
 IC50 8.68 8.48 2.1 2
MDA-MB-231
CHEMBL400
 IC50 8.66 8.45 2.2 2
RPMI-7951
CHEMBL612447
 IC50 8.62 8.62 2.4 1
SK-BR-3
CHEMBL613834
 IC50 8.32 8.32 4.8 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4872.07 ng.hr.mL-1 Mus musculus
CL 42.3 mL.min-1.kg-1 Homo sapiens
CL 4.6 mL.min-1.kg-1 Mus musculus
Cmax 15636.64 nM Mus musculus
T1/2 0.49 hr Homo sapiens
T1/2 4.0 hr Mus musculus
T1/2 4.39 hr Mus musculus
Tmax 0.17 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MDA-MB-453 IC50 = 1.4 nM 8.85 Antiproliferative activity against human MDA-MB-453 cells assessed as cell growt... 34378386
A-375 IC50 = 1.8 nM 8.74 Antiproliferative activity against human A-375 cells assessed as cell growth inh... 34378386
M14 IC50 = 1.9 nM 8.72 Antiproliferative activity against human M14 cells assessed as cell growth inhib... 34378386
Unchecked IC50 = 2.1 nM 8.68 Cytotoxicity against paclitaxel resistant human MDA-MB-231/TxR cells measured af... 34378386
MDA-MB-231 IC50 = 2.2 nM 8.66 Antiproliferative activity against human MDA-MB-231 cells assessed as cell growt... 34378386
RPMI-7951 IC50 = 2.4 nM 8.62 Antiproliferative activity against human RPMI-7951 cells assessed as cell growth... 34378386
M14 IC50 = 2.8 nM 8.55 Cytotoxicity against human M14 cells measured after 72 hrs by western blot 34378386
SK-BR-3 IC50 = 4.8 nM 8.32 Antiproliferative activity against human SK-BR-3 cells assessed as cell growth i... 34378386
M14 IC50 = 4.9 nM 8.31 Cytotoxicity against paclitaxel resistant human M14 cells measured after 72 hrs ... 34378386
A-375 IC50 = 5.1 nM 8.29 Cytotoxicity against human A-375 cells measured after 72 hrs by western blot 34378386
Unchecked IC50 = 5.3 nM 8.28 Cytotoxicity against paclitaxel resistant human A-375/TxR cells measured after 7... 34378386
MDA-MB-231 IC50 = 5.8 nM 8.24 Cytotoxicity against human MDA-MB-231 cells measured after 72 hrs by western blo... 34378386

Literature References

PubMed DOI Target Context # Activities
34378386 10.1021/acs.jmedchem.1c00715 Unchecked 24
34378386 10.1021/acs.jmedchem.1c00715 ADMET 15
34378386 10.1021/acs.jmedchem.1c00715 Salmonella typhimurium 4
34378386 10.1021/acs.jmedchem.1c00715 M14 3
34378386 10.1021/acs.jmedchem.1c00715 A-375 2
34378386 10.1021/acs.jmedchem.1c00715 MDA-MB-231 2
34378386 10.1021/acs.jmedchem.1c00715 Voltage-gated inwardly rectifying potassium channel KCNH2 1
34378386 10.1021/acs.jmedchem.1c00715 Cytochrome P450 2D6 1
34378386 10.1021/acs.jmedchem.1c00715 Cytochrome P450 2C19 1
34378386 10.1021/acs.jmedchem.1c00715 Cytochrome P450 2C9 1
34378386 10.1021/acs.jmedchem.1c00715 Cytochrome P450 2C8 1
34378386 10.1021/acs.jmedchem.1c00715 Cytochrome P450 2B6 1
34378386 10.1021/acs.jmedchem.1c00715 Cytochrome P450 1A2 1
34378386 10.1021/acs.jmedchem.1c00715 No relevant target 1
34378386 10.1021/acs.jmedchem.1c00715 RPMI-7951 1
34378386 10.1021/acs.jmedchem.1c00715 SK-BR-3 1
34378386 10.1021/acs.jmedchem.1c00715 MDA-MB-453 1

Data from ChEMBL 36 via Core Engine