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Compound Detail

CHEMBL32856

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COc1cc(OC)c(C(=O)/C=C/c2cccc([N+](=O)[O-])c2)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL32856
Phase Preclinical
Structure Type MOL
InChI Key YCPYGCFJBDPLNN-BQYQJAHWSA-N
8
Targets
11
Activities
1
Assay Types
0
PK Parameters
14
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

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H17NO6
MW 343.34
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.32

Activity Summary

IC50 11 meas. best 6.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Homo sapiens
CHEMBL372
 IC50 6.66 6.66 220.0 1
HeLa
CHEMBL399
 IC50 5.85 5.81 1400.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.8 5.59 1600.0 2
RAW264.7
CHEMBL612557
 IC50 5.75 5.75 1780.0 1
Thioredoxin reductase
CHEMBL2096978
 IC50 5.46 5.175 3500.0 2
HepG2
CHEMBL395
 IC50 5.31 5.31 4900.0 1
A549
CHEMBL392
 IC50 5.27 5.27 5400.0 1
Leishmania braziliensis
CHEMBL612878
 IC50 4.7 4.7 20000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Homo sapiens IC50 = 220.0 nM 6.66 Inhibition of the production of Interleukin-1-beta from human peripheral blood m... 8496911
HeLa IC50 = 1400.0 nM 5.85 Cytotoxicity against human HeLa cells assessed as inhibition of cell proliferati... 25629304
NON-PROTEIN TARGET IC50 = 1600.0 nM 5.8 Cytotoxicity against human HL60 cells assessed as inhibition of cell proliferati... 25629304
HeLa IC50 = 1700.0 nM 5.77 Cytotoxicity against human HeLa cells assessed as inhibition of cell proliferati... 25629304
RAW264.7 IC50 = 1780.0 nM 5.75 Inhibition of LPS-induced nitric oxide production in mouse RAW264.7 cells 17988874
Thioredoxin reductase IC50 = 3500.0 nM 5.46 Inhibition of TrxR in human HeLa cells assessed as depletion of cellular thiol a... 25629304
NON-PROTEIN TARGET IC50 = 4200.0 nM 5.38 Cytotoxicity against human SSMC-7721 cells assessed as inhibition of cell prolif... 25629304
HepG2 IC50 = 4900.0 nM 5.31 Cytotoxicity against human HepG2 cells assessed as inhibition of cell proliferat... 25629304
A549 IC50 = 5400.0 nM 5.27 Cytotoxicity against human A549 cells assessed as inhibition of cell proliferati... 25629304
Thioredoxin reductase IC50 = 12800.0 nM 4.89 In vitro inhibition of NADPH-reduced TrxR (unknown origin) after 2 hrs incubatio... 25629304
Leishmania braziliensis IC50 = 20000.0 nM 4.7 Antileishmanial activity against promastigotes form of Leishmania braziliensis M... 21757358

Literature References

PubMed DOI Target Context # Activities
25629304 10.1021/jm5016507 HeLa 13
25629304 10.1021/jm5016507 Thioredoxin reductase 5
17988874 10.1016/j.bmc.2007.10.039 RAW264.7 2
25629304 10.1021/jm5016507 NON-PROTEIN TARGET 2
8496911 10.1021/jm00062a016 Homo sapiens 1
17988874 10.1016/j.bmc.2007.10.039 Unchecked 1
18930396 10.1016/j.bmcl.2008.09.105 Low molecular weight protein-tyrosine phosphatase A 1
21757358 10.1016/j.bmc.2011.06.023 Leishmania braziliensis 1
21757358 10.1016/j.bmc.2011.06.023 Vero 1
21757358 10.1016/j.bmc.2011.06.023 Unchecked 1
25629304 10.1021/jm5016507 A549 1
25629304 10.1021/jm5016507 Unchecked 1
25629304 10.1021/jm5016507 Glutathione reductase, mitochondrial 1
25629304 10.1021/jm5016507 HepG2 1

Data from ChEMBL 36 via Core Engine