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Compound Detail

CHEMBL1231178

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O=[N+]([O-])c1ccc(OP(=O)(O)Oc2ccc([N+](=O)[O-])cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1231178
Phase Preclinical
Structure Type MOL
InChI Key MHSVUSZEHNVFKW-UHFFFAOYSA-N
3
Targets
12
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

340.2
MW (Da)
3.06
ALogP
7
HBA
1
HBD
142.0
PSA (Ų)
0.48
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C12H9N2O8P
MW 340.18
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.24

Activity Summary

IC50 12 meas. best 6.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Liver carboxylesterase 1
CHEMBL2265
 IC50 6.85 6.7433 140.0 3
Liver carboxylesterase
CHEMBL3383
 IC50 5.75 5.75 1800.0 5
Cocaine esterase
CHEMBL3180
 IC50 5.39 5.2633 4030.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Liver carboxylesterase 1 IC50 = 140.0 nM 6.85 Inhibition of CE1 in human liver microsomes using 2-(2-Benzoyl-3-methoxyphenyl) ... 26900660
Liver carboxylesterase 1 IC50 = 200.0 nM 6.7 Inhibition of human CE1 using D-luciferin methyl ester as substrate preincubated... 32058719
Liver carboxylesterase 1 IC50 = 210.0 nM 6.68 Inhibition of CE1 in human liver microsomes using D-Luciferin methyl ester as su... 29353723
Liver carboxylesterase IC50 = 1800.0 nM 5.75 Inhibition of pig liver carboxylesterase using 4-nitrophenol acetate as substrat... 28986116
Liver carboxylesterase IC50 = 1800.0 nM 5.75 Inhibition of porcine liver carboxylesterase using 4-nitrophenol acetate as subs... 28578994
Liver carboxylesterase IC50 = 1800.0 nM 5.75 Inhibition of porcine liver carboxylesterase using 4-nitrophenol acetate as subs... 30104121
Liver carboxylesterase IC50 = 1800.0 nM 5.75 Inhibition of porcine liver carboxylesterase using 4-NPA as substrate preincubat... 31640885
Liver carboxylesterase IC50 = 1800.0 nM 5.75 Inhibition of porcine liver carboxylesterase using 4-NPA as substrate preincubat... 33831780
Cocaine esterase IC50 = 4030.0 nM 5.39 Inhibition of human carboxylesterase 2 using 4-benzoyl-N-butyl-1,8-naphthalimide... 26425784
Cocaine esterase IC50 = 6110.0 nM 5.21 Inhibition of CE2 in human liver microsomes using fluorescein diacetate as subst... 26900660
Cocaine esterase IC50 = 6400.0 nM 5.19 Inhibition of CES2 in human liver microsomes assessed as reduction in substrate ... 33965840

Literature References

PubMed DOI Target Context # Activities
31640885 10.1016/j.bmcl.2019.126716 No relevant target 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
33831780 10.1016/j.ejmech.2021.113385 No relevant target 2
28986116 10.1016/j.bmc.2017.09.028 No relevant target 2
28578994 10.1016/j.bmc.2017.05.045 Acetylcholinesterase 1
31640885 10.1016/j.bmcl.2019.126716 Liver carboxylesterase 1
30104121 10.1016/j.bmc.2018.08.010 Acetylcholinesterase 1
30104121 10.1016/j.bmc.2018.08.010 Liver carboxylesterase 1
30104121 10.1016/j.bmc.2018.08.010 No relevant target 1
29353723 10.1016/j.ejmech.2018.01.030 Cocaine esterase 1
29353723 10.1016/j.ejmech.2018.01.030 Liver carboxylesterase 1 1
28578994 10.1016/j.bmc.2017.05.045 Cholinesterase 1
26425784 10.1021/acs.jnatprod.5b00321 Cocaine esterase 1
36325400 10.1039/d2md00192f Liver carboxylesterase 1
28986116 10.1016/j.bmc.2017.09.028 Cholinesterase 1
28986116 10.1016/j.bmc.2017.09.028 Acetylcholinesterase 1
28986116 10.1016/j.bmc.2017.09.028 Liver carboxylesterase 1
27769035 10.1016/j.ejmech.2016.10.013 Unchecked 1
26900660 10.1016/j.ejmech.2016.02.020 Unchecked 1
26900660 10.1016/j.ejmech.2016.02.020 Liver carboxylesterase 1 1

Data from ChEMBL 36 via Core Engine