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Compound Detail

CHEMBL521969

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COc1cc(OC)c2c(c1Cl)O[C@]1(C2=O)C(OCc2ccccc2)=CC(=O)C[C@H]1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL521969
Phase Preclinical
Structure Type MOL
InChI Key LAWAOYZSUFCPKY-ZLOXQWCVSA-N
6
Targets
9
Activities
1
Assay Types
4
PK Parameters
16
Publications
0
Known Names

Molecular Properties

428.9
MW (Da)
4.38
ALogP
6
HBA
0
HBD
71.1
PSA (Ų)
0.70
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H21ClO6
MW 428.87
Aromatic Rings 2
Heavy Atoms 30
NP-Likeness 1.25

Activity Summary

IC50 9 meas. best 6.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trichophyton mentagrophytes
CHEMBL613162
 IC50 6.58 6.58 260.0 1
Unchecked
CHEMBL612545
 IC50 6.05 6.05 900.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.01 6.01 980.0 1
Trichophyton rubrum
CHEMBL612649
 IC50 5.96 5.96 1100.0 1
U2OS
CHEMBL615023
 IC50 5.89 5.865 1300.0 2
MDA-MB-231
CHEMBL400
 IC50 5.79 5.7467 1620.0 3

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.027 - Rattus norvegicus
Fu 0.112 - Mus musculus
T1/2 0.45 hr Mus musculus
T1/2 1.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trichophyton mentagrophytes IC50 = 260.0 nM 6.58 Antifungal activity against Trichophyton mentagrophytes IBT 2724 after 7 days by... 22191585
Unchecked IC50 = 900.0 nM 6.05 Inhibition of centrosomal clustering in human SCC114 cells expressing GFPalpha-t... 19402668
NON-PROTEIN TARGET IC50 = 980.0 nM 6.01 Antiproliferative activity against exponentially growing adherent human SCC114 c... 25872984
Trichophyton rubrum IC50 = 1100.0 nM 5.96 Antifungal activity against Trichophyton rubrum IBT 29284 after 7 days by micro ... 22191585
U2OS IC50 = 1300.0 nM 5.89 Antiproliferative activity against human U2OS cells after 72 hrs by CellTiter-Gl... 28258034
U2OS IC50 = 1450.0 nM 5.84 Cytotoxicity against human U2OS cells assessed as reduction in cell viability af... 27061984
MDA-MB-231 IC50 = 1620.0 nM 5.79 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viabil... 27061984
MDA-MB-231 IC50 = 1700.0 nM 5.77 Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by CellTi... 28258034
MDA-MB-231 IC50 = 2100.0 nM 5.68 Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 48 ... 22191585

Literature References

PubMed DOI Target Context # Activities
28258034 10.1016/j.ejmech.2017.02.055 No relevant target 8
28258034 10.1016/j.ejmech.2017.02.055 Plasma 4
25872984 10.1016/j.bmcl.2015.03.081 HCC1937 2
28258034 10.1016/j.ejmech.2017.02.055 Liver 2
19402668 10.1021/jm801517j Unchecked 1
22191585 10.1021/jm200835c Trichophyton mentagrophytes 1
22191585 10.1021/jm200835c Trichophyton rubrum 1
22191585 10.1021/jm200835c MDA-MB-231 1
25872984 10.1016/j.bmcl.2015.03.081 NON-PROTEIN TARGET 1
27061984 10.1016/j.ejmech.2016.03.071 ADMET 1
27061984 10.1016/j.ejmech.2016.03.071 No relevant target 1
27061984 10.1016/j.ejmech.2016.03.071 U2OS 1
27061984 10.1016/j.ejmech.2016.03.071 MDA-MB-231 1
27061984 10.1016/j.ejmech.2016.03.071 Liver microsome 1
28258034 10.1016/j.ejmech.2017.02.055 MDA-MB-231 1
28258034 10.1016/j.ejmech.2017.02.055 U2OS 1

Data from ChEMBL 36 via Core Engine