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Compound Detail

CHEMBL23838

PARAOXON
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CCOP(=O)(OCC)Oc1ccc([N+](=O)[O-])cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL23838
Name PARAOXON
Phase Preclinical
Structure Type MOL
InChI Key WYMSBXTXOHUIGT-UHFFFAOYSA-N

Known Names

Diethyl p-nitrophenyl phosphate E-600 E600 Miotisal NSC-404110 Paraoxon Parathion oxygen analog Phosphacol
9
Targets
12
Activities
2
Assay Types
1
PK Parameters
20
Publications
8
Known Names
1
Indications

Molecular Properties

275.2
MW (Da)
3.15
ALogP
6
HBA
0
HBD
87.9
PSA (Ų)
0.43
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C10H14NO6P
MW 275.20
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.57

Indications

Glaucoma

ATC Classification

S01EB10
paraoxon
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

IC50 11 meas. best 8.15
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cholinesterase
CHEMBL1914
 IC50 8.15 8.15 7.0 1
Acetylcholinesterase
CHEMBL220
 IC50 8.0 8.0 10.0 1
Acetylcholinesterase
CHEMBL3198
 IC50 7.89 7.89 13.0 1
Carbonic anhydrase 2
CHEMBL205
 IC50 7.23 7.23 59.0 1
Carbonic anhydrase 1
CHEMBL261
 IC50 6.47 6.47 338.0 1
Fatty-acid amide hydrolase 1
CHEMBL3455
 IC50 6.27 5.75 540.0 2
Carbonic anhydrase 13
CHEMBL2186
 IC50 5.99 5.99 1021.0 1
Cannabinoid receptor 1
CHEMBL3037
 IC50 5.92 5.92 1200.0 1
Monoglyceride lipase
CHEMBL5774
 IC50 5.92 5.78 1200.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 24.33 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cholinesterase IC50 = 7.0 nM 8.15 Inhibition of human BChE using butyrylthiocholine as substrate measured for 30 s... 28404526
Acetylcholinesterase IC50 = 10.0 nM 8.0 Inhibition of human AChE using p-nitrophenyl acetate as substrate measured for 3... 28404526
Acetylcholinesterase IC50 = 13.0 nM 7.89 Displacement of acetylcholine from AChE in Swiss Webster mouse brain after 5 min... 18438404
Carbonic anhydrase 2 IC50 = 59.0 nM 7.23 Inhibition of esterase activity of human carbonic anhydrase 2 by CO2 hydration m... 20833546
Carbonic anhydrase 1 IC50 = 338.0 nM 6.47 Inhibition of esterase activity of human carbonic anhydrase 1 by CO2 hydration m... 20833546
Fatty-acid amide hydrolase 1 IC50 = 540.0 nM 6.27 Inhibition of FAAH-mediated [3H]anandamide hydrolysis in mouse brain 18752948
Carbonic anhydrase 13 IC50 = 1021.0 nM 5.99 Inhibition of esterase activity of mouse carbonic anhydrase 13 by CO2 hydration ... 20833546
Cannabinoid receptor 1 IC50 = 1200.0 nM 5.92 Displacement of [3H]CP-55940 from CB1 receptor in mouse brain 18752948
Monoglyceride lipase IC50 = 1200.0 nM 5.92 Displacement of 2-arachidonylglycerol from MAGL in Swiss Webster mouse brain aft... 18438404
Monoglyceride lipase IC50 = 2300.0 nM 5.64 Inhibition of MAGL-mediated 2-arachidonoylglycerol hydrolysis in mouse brain 18752948
Fatty-acid amide hydrolase 1 IC50 = 5900.0 nM 5.23 Displacement of [3H]anandamide from FAAH in Swiss Webster mouse brain after 5 mi... 18438404

Literature References

PubMed DOI Target Context # Activities
20005727 10.1016/j.bmc.2009.11.052 Acetylcholinesterase 6
11052723 10.1021/jf000548p Acetylcholinesterase 5
10866401 10.1016/s0960-894x(00)00213-4 Xaa-Pro dipeptidase 5
23453838 10.1016/j.bmcl.2013.02.010 Acetylcholinesterase 4
17319687 10.1021/jf0631934 Muscarinic acetylcholine receptor DM1 4
28404526 10.1016/j.bmc.2017.03.058 Acetylcholinesterase 3
11814848 10.1016/s0968-0896(01)00326-1 Acetylcholinesterase 3
20833546 10.1016/j.bmcl.2010.08.110 Carbonic anhydrase 13 3
20833546 10.1016/j.bmcl.2010.08.110 Carbonic anhydrase 2 3
20833546 10.1016/j.bmcl.2010.08.110 Carbonic anhydrase 1 3
20034789 10.1016/j.bmcl.2009.12.007 Acetylcholinesterase 2
18438404 10.1038/nchembio.86 Fatty-acid amide hydrolase 1 1
35678759 10.1021/acs.jmedchem.2c00658 Unchecked 1
18438404 10.1038/nchembio.86 Acetylcholinesterase 1
3351852 10.1021/jm00399a012 No relevant target 1
18438404 10.1038/nchembio.86 Monoglyceride lipase 1
12729627 10.1016/s0960-894x(03)00290-7 Serum paraoxonase/arylesterase 1 1
18752948 10.1016/j.bmcl.2008.08.007 Cannabinoid receptor 1 1
18752948 10.1016/j.bmcl.2008.08.007 Fatty-acid amide hydrolase 1 1
6325692 10.1021/jm00371a017 No relevant target 1

Data from ChEMBL 36 via Core Engine