Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1241)
Drug Name
Paraoxon
Synonyms
Chinorta; Chinorto; Diethyl 4-nitrophenyl phosphate; Diethyl p-nitrophenyl phosphate; Diethyl paraoxon; Diethyl-p-nitrophenyl phosphate; Diethylparaoxon; Ester 25; Ethyl paraoxan; Ethyl paraoxon; Eticol; Fosfakol; Mintaco; Mintacol; Miotisal; Miotisal A; Oxyparathion; PARAOXON; Paraoxon-ethyl; Paraoxone; Paroxan; Pestox 101; Phosphachole; Phosphacol; Phosphakol; Soluglacit; Soluglaucit; p-Nitrophenyl diethyl phosphate; 311-45-5; E 600 (pesticide); Phosphoric acid diethyl 4-nitrophenyl ester; Phosphoric acid, diethyl 4-nitrophenyl ester
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 275.19 Topological Polar Surface Area 90.6
Heavy Atom Count 18 Rotatable Bond Count 6
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
9395
ChEBI ID
CHEBI:27827
CAS Number
311-45-5
TTD Drug ID
D08XQI
Formula
C10H14NO6P
Canonical SMILES
CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-]
InChI
1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3
InChIKey
WYMSBXTXOHUIGT-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Diethylphosphoric acid DM004082
654
Oxidation - Hydrolyzationn 1 [4]
Paraoxon Metabolite C3 DM004083 N. A. Unclear 1 [6]
p-nitrophenol DM004005
980
Oxidation - Hydrolyzationn 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004457 Paraoxon Diethylphosphoric acid Oxidation - Hydrolyzationn PTE [4]
MR004459 Paraoxon Paraoxon Metabolite C3 Unclear PON1 [6]
MR004458 Paraoxon p-nitrophenol Oxidation - Hydrolyzationn PTE [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
phosphotriesterase (PTE) DMEN206 Bacteroides fragilis Not Available Not Available [4]
Serum paraoxonase/arylesterase 1 (PON1) DME0169 Homo sapiens
PON1_HUMAN
3.1.1.2
[5]
Serum paraoxonase/arylesterase 1 (PON1) DME0169 Homo sapiens
PON1_HUMAN
3.1.1.2
[6]
Serum paraoxonase/arylesterase 2 (PON2) DME0620 Homo sapiens
PON2_HUMAN
3.1.1.2
[7]
⏷ Show the Full List of 9  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Serum paraoxonase/arylesterase 1 (PON1) DME0169 Km = 0.27 microM
PON1_HUMAN
[5]
References
1 Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels. Bioorg Med Chem Lett. 2008 Nov 15;18(22):5875-8.
2 Diazinon, chlorpyrifos and parathion are metabolised by multiple cytochromes P450 in human liver. Toxicology. 2006 Jul 5;224(1-2):22-32.
3 Interaction of ethanol and the organophosphorus insecticide parathion. Biochem Pharmacol. 1995 Nov 27;50(11):1925-32.
4 Encapsulation of phosphotriesterase within murine erythrocytes
5 Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters. Drug Metab Dispos. 2000 Nov;28(11):1335-42.
6 Paraoxon hydrolysis vs. covalent binding in the elimination of paraoxon in the rabbit
7 Paraoxonases-1, -2 and -3: what are their functions? Chem Biol Interact. 2016 Nov 25;259(Pt B):51-62.

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