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Compound Detail

CHEMBL4866085

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COc1ccc(CNC(=O)c2cc(F)ccc2N2CCOCC2)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4866085
Phase Preclinical
Structure Type MOL
InChI Key RNCMVGCGDYWOHU-UHFFFAOYSA-N
14
Targets
20
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

360.4
MW (Da)
2.31
ALogP
5
HBA
2
HBD
71.0
PSA (Ų)
0.86
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H21FN2O4
MW 360.39
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -1.43

Activity Summary

IC50 20 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A-431
CHEMBL614069
 IC50 7.85 7.85 14.0 1
K562
CHEMBL385
 IC50 7.77 7.745 17.0 2
HCT-8
CHEMBL613510
 IC50 7.7 7.335 20.0 2
H22
CHEMBL614998
 IC50 7.62 7.58 24.0 2
HepG2
CHEMBL395
 IC50 7.6 7.585 25.0 2
MDA-MB-231
CHEMBL400
 IC50 7.58 7.575 26.0 2
Bel-7402
CHEMBL614279
 IC50 7.57 7.275 27.0 2
HCT-116
CHEMBL394
 IC50 7.54 7.54 29.0 1
MCF7
CHEMBL387
 IC50 7.5 7.5 32.0 1
L02
CHEMBL4296457
 IC50 6.95 6.95 112.0 1
HUVEC
CHEMBL613979
 IC50 6.92 6.92 120.0 1
HFL1
CHEMBL612547
 IC50 6.9 6.9 126.0 1
K562/VCR
CHEMBL4296450
 IC50 6.69 6.69 205.0 1
Unchecked
CHEMBL612545
 IC50 5.52 5.52 3030.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A-431 IC50 = 14.0 nM 7.85 Antiproliferative activity against human A-431 cells assessed as reduction in ce... 33676300
K562 IC50 = 17.0 nM 7.77 Antiproliferative activity against human K562 cells assessed as inhibition of ce... 35926141
K562 IC50 = 19.0 nM 7.72 Antiproliferative activity against human K562 cells assessed as reduction in cel... 33676300
HCT-8 IC50 = 20.0 nM 7.7 Antiproliferative activity against human HCT-8 cells assessed as reduction in ce... 33676300
H22 IC50 = 24.0 nM 7.62 Antiproliferative activity against mouse H22 cells assessed as reduction in cell... 33676300
HepG2 IC50 = 25.0 nM 7.6 Antiproliferative activity against human HepG2 cells assessed as reduction in ce... 33676300
MDA-MB-231 IC50 = 26.0 nM 7.58 Antiproliferative activity against human MDA-MB-231 cells assessed as inhibition... 35926141
MDA-MB-231 IC50 = 27.0 nM 7.57 Antiproliferative activity against human MDA-MB-231 cells assessed as reduction ... 33676300
Bel-7402 IC50 = 27.0 nM 7.57 Antiproliferative activity against human Bel-7402 cells assessed as reduction in... 33676300
HepG2 IC50 = 27.0 nM 7.57 Antiproliferative activity against human HepG2 cells assessed as inhibition of c... 35926141
HCT-116 IC50 = 29.0 nM 7.54 Antiproliferative activity against human HCT-116 cells assessed as inhibition of... 35926141
H22 IC50 = 29.0 nM 7.54 Antiproliferative activity against mouse H22 cells assessed as inhibition of cel... 35926141
MCF7 IC50 = 32.0 nM 7.5 Antiproliferative activity against human MCF7 cells assessed as inhibition of ce... 35926141
Bel-7402 IC50 = 104.0 nM 6.98 Antiproliferative activity against ADR-resistant human Bel-7402 cells assessed a... 33676300
HCT-8 IC50 = 106.0 nM 6.97 Antiproliferative activity against taxol-resistant human HCT-8 cells assessed as... 33676300
L02 IC50 = 112.0 nM 6.95 Cytotoxicity against human L02 cells assessed as reduction in cell viability inc... 33676300
HUVEC IC50 = 120.0 nM 6.92 Cytotoxicity against HUVEC incubated for 6 hrs by inverted microscopic analysis 33676300
HFL1 IC50 = 126.0 nM 6.9 Antiproliferative activity against human HFL1 cells assessed as inhibition of ce... 35926141
K562/VCR IC50 = 205.0 nM 6.69 Antiproliferative activity against VCR resistant human K562/VCR cells assessed a... 33676300
Unchecked IC50 = 3030.0 nM 5.52 Inhibition of pig brain tubulin polymerisation incubated for 30 mins and measure... 33676300

Literature References

PubMed DOI Target Context # Activities
33676300 10.1016/j.ejmech.2021.113316 A-431 38
33676300 10.1016/j.ejmech.2021.113316 Unchecked 12
35926141 10.1021/acs.jmedchem.2c00681 H22 6
33676300 10.1016/j.ejmech.2021.113316 H22 5
33676300 10.1016/j.ejmech.2021.113316 No relevant target 3
33676300 10.1016/j.ejmech.2021.113316 HUVEC 3
33676300 10.1016/j.ejmech.2021.113316 ADMET 3
33676300 10.1016/j.ejmech.2021.113316 Bel-7402 2
33676300 10.1016/j.ejmech.2021.113316 HCT-8 2
35926141 10.1021/acs.jmedchem.2c00681 Unchecked 2
35926141 10.1021/acs.jmedchem.2c00681 Histone deacetylase 2
33676300 10.1016/j.ejmech.2021.113316 L02 1
33676300 10.1016/j.ejmech.2021.113316 K562/VCR 1
33676300 10.1016/j.ejmech.2021.113316 MDA-MB-231 1
33676300 10.1016/j.ejmech.2021.113316 K562 1
35926141 10.1021/acs.jmedchem.2c00681 K562 1
35926141 10.1021/acs.jmedchem.2c00681 HepG2 1
35926141 10.1021/acs.jmedchem.2c00681 HCT-116 1
35926141 10.1021/acs.jmedchem.2c00681 MDA-MB-231 1
33676300 10.1016/j.ejmech.2021.113316 HepG2 1

Data from ChEMBL 36 via Core Engine