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Compound Detail

CHEMBL3115914

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O=C(/C=C/c1ccc([N+](=O)[O-])cc1)c1ccc(O)c(O)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3115914
Phase Preclinical
Structure Type MOL
InChI Key CUEWOYAEVHHUTJ-XVNBXDOJSA-N
10
Targets
20
Activities
2
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

285.2
MW (Da)
2.90
ALogP
5
HBA
2
HBD
100.7
PSA (Ų)
0.30
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C15H11NO5
MW 285.25
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.10

Activity Summary

IC50 11 meas. best 6.08
EC50 9 meas. best 5.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
GroEL/GroES
CHEMBL4106139
 IC50 6.08 5.338 830.0 5
Unchecked
CHEMBL612545
 IC50 5.89 5.2875 1300.0 4
HSP60/HSP10
CHEMBL4106131
 IC50 5.28 5.28 5200.0 1
HCT-116
CHEMBL394
 EC50 5.24 5.225 5800.0 2
HT-29
CHEMBL384
 EC50 5.09 5.09 8200.0 1
DLD-1
CHEMBL614285
 EC50 5.02 5.02 9600.0 1
ADMET
CHEMBL612558
 EC50 5.0 5.0 9900.0 1
HEK293
CHEMBL614818
 EC50 4.92 4.92 12000.0 1
Staphylococcus aureus
CHEMBL352
 EC50 4.64 4.52 23000.0 2
Escherichia coli
CHEMBL354
 EC50 4.32 4.32 48000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
GroEL/GroES IC50 = 830.0 nM 6.08 Inhibition of Escherichia coli GroEL/GroES using Escherichia coli GroEL expresse... 27184767
GroEL/GroES IC50 = 1200.0 nM 5.92 Inhibition of Escherichia coli GroEL/GroES using Escherichia coli GroEL expresse... 27184767
Unchecked IC50 = 1300.0 nM 5.89 Inhibition of Escherichia coli GroEL expressed in NEB-5-alpha Escherichia coli c... 36356534
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of Escherichia coli GroEL expressed in NEB-5-alpha Escherichia coli c... 36356534
GroEL/GroES IC50 = 2400.0 nM 5.62 Inhibition of Escherichia coli GroEL/GroES expressed in Escherichia coli DH5alph... 24418775
HSP60/HSP10 IC50 = 5200.0 nM 5.28 Inhibition of human HSP60/HSP10 expressed in Escherichia coli Rosetta2(DE3) cell... 27184767
HCT-116 EC50 = 5800.0 nM 5.24 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 36356534
HCT-116 EC50 = 6100.0 nM 5.21 Cytotoxicity against p53-/- human HCT-116 cells assessed as reduction in cell vi... 36356534
Unchecked IC50 = 6200.0 nM 5.21 Inhibition of human mitochondrial HSP60 expressed in Escherichia coli Rosetta 2 ... 36356534
HT-29 EC50 = 8200.0 nM 5.09 Cytotoxicity against human HT-29 cells assessed as reduction in cell viability i... 36356534
DLD-1 EC50 = 9600.0 nM 5.02 Cytotoxicity against human DLD-1 cells assessed as reduction in cell viability i... 36356534
ADMET EC50 = 9900.0 nM 5.0 Cytotoxicity against human THLE3 cells assessed as reduction in cell viability a... 27184767
HEK293 EC50 = 12000.0 nM 4.92 Cytotoxicity against HEK293 cells assessed as reduction in cell viability after ... 27184767
GroEL/GroES IC50 = 12000.0 nM 4.92 Inhibition of Escherichia coli GroEL/GroES using Escherichia coli GroEL expresse... 27184767
Staphylococcus aureus EC50 = 23000.0 nM 4.64 Antibacterial activity against multidrug resistant Staphylococcus aureus subsp. ... 27184767
Staphylococcus aureus EC50 = 40000.0 nM 4.4 Antibacterial activity against methicillin resistant Staphylococcus aureus subsp... 27184767
Unchecked IC50 = 45000.0 nM 4.35 Inhibition of refolded rhodanese reporter enzyme (unknown origin) 36356534
Escherichia coli EC50 = 48000.0 nM 4.32 Antibacterial activity against Escherichia coli SM101 assessed as reduction in b... 27184767
GroEL/GroES IC50 = 71000.0 nM 4.15 Inhibition of Escherichia coli GroEL/GroES-ATPase activity expressed in Escheric... 24418775

Literature References

PubMed DOI Target Context # Activities
36356534 10.1016/j.bmc.2022.117072 Unchecked 7
27184767 10.1016/j.bmcl.2016.04.089 GroEL/GroES 5
27184767 10.1016/j.bmcl.2016.04.089 Escherichia coli 3
27184767 10.1016/j.bmcl.2016.04.089 Staphylococcus aureus 2
27184767 10.1016/j.bmcl.2016.04.089 HSP60/HSP10 2
36356534 10.1016/j.bmc.2022.117072 HCT-116 2
24418775 10.1016/j.bmcl.2013.12.100 GroEL/GroES 2
27184767 10.1016/j.bmcl.2016.04.089 HEK293 1
36356534 10.1016/j.bmc.2022.117072 FHC 1
36356534 10.1016/j.bmc.2022.117072 HT-29 1
36356534 10.1016/j.bmc.2022.117072 DLD-1 1
27184767 10.1016/j.bmcl.2016.04.089 Enterobacter cloacae 1
27184767 10.1016/j.bmcl.2016.04.089 Pseudomonas aeruginosa 1
27184767 10.1016/j.bmcl.2016.04.089 Acinetobacter baumannii 1
27184767 10.1016/j.bmcl.2016.04.089 Klebsiella pneumoniae subsp. pneumoniae 1
27184767 10.1016/j.bmcl.2016.04.089 ADMET 1
27184767 10.1016/j.bmcl.2016.04.089 Enterococcus faecium 1
27184767 10.1016/j.bmcl.2016.04.089 Bacillus subtilis 1
24418775 10.1016/j.bmcl.2013.12.100 Unchecked 1

Data from ChEMBL 36 via Core Engine