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Compound Detail

CHEMBL32857

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COc1cc(OC)c(C(=O)/C=C/c2ccc([N+](=O)[O-])cc2)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL32857
Phase Preclinical
Structure Type MOL
InChI Key VJNBRWWDKJRZIL-RMKNXTFCSA-N
16
Targets
16
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

343.3
MW (Da)
3.52
ALogP
6
HBA
0
HBD
87.9
PSA (Ų)
0.33
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H17NO6
MW 343.34
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.17

Activity Summary

IC50 16 meas. best 6.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Homo sapiens
CHEMBL372
 IC50 6.39 6.39 407.0 1
RAW264.7
CHEMBL612557
 IC50 5.61 5.61 2450.0 1
PC-3
CHEMBL390
 IC50 5.6 5.6 2500.0 1
Caco-2
CHEMBL614058
 IC50 5.58 5.58 2600.0 1
HCT-116
CHEMBL394
 IC50 5.57 5.57 2700.0 1
HaCaT
CHEMBL614392
 IC50 5.55 5.55 2800.0 1
MDA-MB-231
CHEMBL400
 IC50 5.48 5.48 3300.0 1
RL
CHEMBL2366175
 IC50 5.47 5.47 3400.0 1
NCI-H727
CHEMBL1075545
 IC50 5.39 5.39 4100.0 1
Huh-7
CHEMBL614039
 IC50 5.31 5.31 4900.0 1
MCF7
CHEMBL387
 IC50 5.3 5.3 5000.0 1
A549
CHEMBL392
 IC50 5.15 5.15 7100.0 1
Fibroblast
CHEMBL613838
 IC50 5.14 5.14 7300.0 1
HeLa
CHEMBL399
 IC50 5.1 5.1 8000.0 1
HepG2
CHEMBL395
 IC50 5.03 5.03 9400.0 1
Leishmania braziliensis
CHEMBL612878
 IC50 4.93 4.93 11700.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Homo sapiens IC50 = 407.0 nM 6.39 Inhibition of the production of Interleukin-1-beta from human peripheral blood m... 8496911
RAW264.7 IC50 = 2450.0 nM 5.61 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells 17988874
PC-3 IC50 = 2500.0 nM 5.6 Cytotoxicity against human PC3 cells assessed as cell viability after 48 hrs by ... 28214231
Caco-2 IC50 = 2600.0 nM 5.58 Cytotoxicity against human Caco2 cells assessed as cell viability after 48 hrs b... 28214231
HCT-116 IC50 = 2700.0 nM 5.57 Cytotoxicity against human HCT116 cells assessed as cell viability after 48 hrs ... 28214231
HaCaT IC50 = 2800.0 nM 5.55 Cytotoxicity against human HaCaT cells assessed as cell viability after 48 hrs b... 28214231
MDA-MB-231 IC50 = 3300.0 nM 5.48 Cytotoxicity against human MDA-MB-231 cells assessed as cell viability after 48 ... 28214231
RL IC50 = 3400.0 nM 5.47 Cytotoxicity against human RL assessed as cell viability after 48 hrs by Hoechst... 28214231
NCI-H727 IC50 = 4100.0 nM 5.39 Cytotoxicity against human NCI-H727 cells assessed as cell viability after 48 hr... 28214231
Huh-7 IC50 = 4900.0 nM 5.31 Cytotoxicity against human HuH7 cells assessed as cell viability after 48 hrs by... 28214231
MCF7 IC50 = 5000.0 nM 5.3 Cytotoxicity against human MCF7 assessed as cell viability after 48 hrs by Hoech... 28214231
A549 IC50 = 7100.0 nM 5.15 Cytotoxicity against human A549 cells assessed as inhibition of cell proliferati... 25629304
Fibroblast IC50 = 7300.0 nM 5.14 Cytotoxicity against human fibroblasts assessed as cell viability after 48 hrs b... 28214231
HeLa IC50 = 8000.0 nM 5.1 Cytotoxicity against human HeLa cells assessed as inhibition of cell proliferati... 25629304
HepG2 IC50 = 9400.0 nM 5.03 Cytotoxicity against human HepG2 cells assessed as inhibition of cell proliferat... 25629304
Leishmania braziliensis IC50 = 11700.0 nM 4.93 Antileishmanial activity against promastigotes form of Leishmania braziliensis M... 21757358

Literature References

PubMed DOI Target Context # Activities
28214231 10.1016/j.bmc.2017.01.049 Unchecked 9
28214231 10.1016/j.bmc.2017.01.049 Caco-2 2
28214231 10.1016/j.bmc.2017.01.049 Fibroblast 2
28214231 10.1016/j.bmc.2017.01.049 HaCaT 2
28214231 10.1016/j.bmc.2017.01.049 NCI-H727 2
28214231 10.1016/j.bmc.2017.01.049 PC-3 2
28214231 10.1016/j.bmc.2017.01.049 HCT-116 2
28214231 10.1016/j.bmc.2017.01.049 MDA-MB-231 2
28214231 10.1016/j.bmc.2017.01.049 Huh-7 2
17988874 10.1016/j.bmc.2007.10.039 RAW264.7 2
25629304 10.1021/jm5016507 HepG2 1
8496911 10.1021/jm00062a016 Homo sapiens 1
25629304 10.1021/jm5016507 A549 1
25629304 10.1021/jm5016507 HeLa 1
21757358 10.1016/j.bmc.2011.06.023 Unchecked 1
21757358 10.1016/j.bmc.2011.06.023 Vero 1
21757358 10.1016/j.bmc.2011.06.023 Leishmania braziliensis 1
17988874 10.1016/j.bmc.2007.10.039 Unchecked 1
28214231 10.1016/j.bmc.2017.01.049 RL 1
28214231 10.1016/j.bmc.2017.01.049 MCF7 1

Data from ChEMBL 36 via Core Engine