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Compound Detail

CHEMBL4789173

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COc1ccc([C@H]2[C@H](CF)C(=O)N2c2cc(OC)c(OC)c(OC)c2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4789173
Phase Preclinical
Structure Type MOL
InChI Key MIRNCGQQVHLNFT-UGSOOPFHSA-N
8
Targets
10
Activities
1
Assay Types
2
PK Parameters
14
Publications
0
Known Names

Molecular Properties

391.4
MW (Da)
3.10
ALogP
6
HBA
1
HBD
77.5
PSA (Ų)
0.73
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 C20H22FNO6
MW 391.40
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 0.21

Activity Summary

IC50 10 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MDA-MB-231
CHEMBL400
 IC50 9.0 8.98 1.0 2
A2780
CHEMBL614004
 IC50 9.0 9.0 1.0 1
Huh-7
CHEMBL614039
 IC50 9.0 9.0 1.0 1
HeLa
CHEMBL399
 IC50 8.52 8.345 3.0 2
A2780/Taxol
CHEMBL4483224
 IC50 8.44 8.44 3.6 1
SK-OV-3
CHEMBL614925
 IC50 8.42 8.42 3.8 1
MCF7
CHEMBL387
 IC50 7.9 7.9 12.5 1
Unchecked
CHEMBL612545
 IC50 6.0 6.0 1000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 8.6 mL.min-1.kg-1 Homo sapiens
T1/2 2.417 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Huh-7 IC50 = 1.0 nM 9.0 Antiproliferative activity against human Huh-7 cells assessed as reduction in ce... 32339854
MDA-MB-231 IC50 = 1.0 nM 9.0 Antiproliferative activity against human MDA-MB-231 cells assessed as reduction ... 32339854
A2780 IC50 = 1.0 nM 9.0 Antiproliferative activity against human A2780 cells assessed as reduction in ce... 32339854
MDA-MB-231 IC50 = 1.1 nM 8.96 Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition... 35405397
HeLa IC50 = 3.0 nM 8.52 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 32339854
A2780/Taxol IC50 = 3.6 nM 8.44 Antiproliferative activity against paclitaxel-resistant human A2780T cells asses... 32339854
SK-OV-3 IC50 = 3.8 nM 8.42 Antiproliferative activity against human SK-OV-3 cells assessed as inhibition of... 35405397
HeLa IC50 = 6.7 nM 8.17 Antiproliferative activity against human HeLa cells assessed as inhibition of ce... 35405397
MCF7 IC50 = 12.5 nM 7.9 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 35405397
Unchecked IC50 = 1000.0 nM 6.0 Inhibition of pig brain tubulin polymerization by absorbance based analysis 32339854

Literature References

PubMed DOI Target Context # Activities
32339854 10.1016/j.ejmech.2020.112323 HeLa 23
32339854 10.1016/j.ejmech.2020.112323 ADMET 8
32339854 10.1016/j.ejmech.2020.112323 Unchecked 7
32339854 10.1016/j.ejmech.2020.112323 MDA-MB-231 3
32339854 10.1016/j.ejmech.2020.112323 A2780 3
32339854 10.1016/j.ejmech.2020.112323 HUVEC 2
32339854 10.1016/j.ejmech.2020.112323 Huh-7 1
32339854 10.1016/j.ejmech.2020.112323 A2780/Taxol 1
32339854 10.1016/j.ejmech.2020.112323 No relevant target 1
32339854 10.1016/j.ejmech.2020.112323 Danio rerio 1
35405397 10.1016/j.ejmech.2022.114344 HeLa 1
35405397 10.1016/j.ejmech.2022.114344 MDA-MB-231 1
35405397 10.1016/j.ejmech.2022.114344 SK-OV-3 1
35405397 10.1016/j.ejmech.2022.114344 MCF7 1

Data from ChEMBL 36 via Core Engine