Details of the Drug

General Information of Drug (ID: DMN4ZKC)

Drug Name
PARAOXON
Synonyms
PARAOXON; Phosphacol; Diethyl paraoxon; 311-45-5; Ethyl paraoxon; Diethyl 4-nitrophenyl phosphate; Phosphachole; Mintacol; Paraoxone; Miotisal; Fosfakol; Phosphakol; Oxyparathion; Chinorto; Diethyl p-nitrophenyl phosphate; Paroxan; Mintaco; Chinorta; Eticol; Miotisal A; Diethylparaoxon; Soluglaucit; Soluglacit; Paraoxon-ethyl; Ethyl paraoxan; p-Nitrophenyl diethyl phosphate; Phosphoric acid, diethyl 4-nitrophenyl ester; Ester 25; Pestox 101; E 600 (pesticide); Diethyl-p-nitrophenyl phosphate; Phosphoric acid diethyl 4-nitrophenyl ester
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 275.19
Logarithm of the Partition Coefficient (xlogp) 2
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C10H14NO6P
IUPAC Name
diethyl (4-nitrophenyl) phosphate
Canonical SMILES
CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-]
InChI
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
Cross-matching ID
PubChem CID
9395
ChEBI ID
CHEBI:27827
CAS Number
311-45-5
DrugBank ID
DB13495
TTD ID
D08XQI
INTEDE ID
DR1241

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetylcholinesterase (AChE) TT1RS9F ACES_HUMAN Inhibitor [2]
Cannabinoid receptor 1 (CB1) TT6OEDT CNR1_HUMAN Inhibitor [1]
Carbonic anhydrase (CA) TTUNARX NOUNIPROTAC Inhibitor [3]
Carbonic anhydrase I (CA-I) TTHQPL7 CAH1_HUMAN Inhibitor [3]
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [3]
Fatty acid amide hydrolase (FAAH) TTDP1UC NOUNIPROTAC Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [5]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [4]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [4]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [4]
Serum paraoxonase/arylesterase 1 (PON1) DESDN74 PON1_HUMAN Substrate [6]
Serum paraoxonase/arylesterase 2 (PON2) DEHJU7E PON2_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
A-kinase anchor protein 12 (AKAP12) OTCVRDDX AKA12_HUMAN Gene/Protein Processing [8]
Abscission/NoCut checkpoint regulator OT6V9IDI ANCHR_HUMAN Gene/Protein Processing [9]
Acetylcholinesterase (ACHE) OT2H8HG6 ACES_HUMAN Gene/Protein Processing [10]
Actin, cytoplasmic 1 (ACTB) OT1MCP2F ACTB_HUMAN Gene/Protein Processing [9]
Acyl-CoA-binding domain-containing protein 5 (ACBD5) OT7L16DY ACBD5_HUMAN Gene/Protein Processing [8]
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [11]
Alpha-enolase (ENO1) OTB1KWJS ENOA_HUMAN Gene/Protein Processing [9]
Aromatic-L-amino-acid decarboxylase (DDC) OT0TSW09 DDC_HUMAN Protein Interaction/Cellular Processes [12]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Gene/Protein Processing [13]
ATP synthase subunit beta, mitochondrial (ATP5F1B) OTLFZUQK ATPB_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Acetylcholinesterase (AChE) DTT ACHE 6.39E-02 -1.07 -1.15
Cytochrome P450 2E1 (CYP2E1) DME CYP2E1 9.45E-02 -1.86E-01 -9.83E-01
Serum paraoxonase/arylesterase 1 (PON1) DME PON1 6.73E-01 -1.29E-02 -1.08E-01
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 5.57E-01 -7.89E-02 -7.93E-01
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 8.46E-01 -6.63E-03 -4.49E-02
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 9.57E-01 9.43E-03 1.29E-01
Serum paraoxonase/arylesterase 2 (PON2) DME PON2 7.02E-01 1.29E-01 4.19E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.76E-01 1.26E-01 8.27E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Monoacylglycerol lipase regulates 2-arachidonoylglycerol action and arachidonic acid levels. Bioorg Med Chem Lett. 2008 Nov 15;18(22):5875-8.
2 Activation of the endocannabinoid system by organophosphorus nerve agents. Nat Chem Biol. 2008 Jun;4(6):373-8.
3 Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of - but not of -, - and -carbonic anhydrases. Bioorg Med Chem Lett. 2010 Nov 1;20(21):6208-12.
4 Diazinon, chlorpyrifos and parathion are metabolised by multiple cytochromes P450 in human liver. Toxicology. 2006 Jul 5;224(1-2):22-32.
5 Interaction of ethanol and the organophosphorus insecticide parathion. Biochem Pharmacol. 1995 Nov 27;50(11):1925-32.
6 Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters. Drug Metab Dispos. 2000 Nov;28(11):1335-42.
7 Paraoxonases-1, -2 and -3: what are their functions? Chem Biol Interact. 2016 Nov 25;259(Pt B):51-62.
8 Genomic and phenotypic alterations of the neuronal-like cells derived from human embryonal carcinoma stem cells (NT2) caused by exposure to organophosphorus compounds paraoxon and mipafox. Int J Mol Sci. 2014 Jan 9;15(1):905-26. doi: 10.3390/ijms15010905.
9 Paraoxon-induced protein expression changes to SH-SY5Y cells. Chem Res Toxicol. 2010 Nov 15;23(11):1656-62. doi: 10.1021/tx100192f. Epub 2010 Oct 8.
10 Improvement of acetylcholinesterase-based assay for organophosphates in way of identification by reactivators. Talanta. 2008 Oct 19;77(1):451-4.
11 Serum albumins and detoxication of anti-cholinesterase agents. Chem Biol Interact. 2010 Sep 6;187(1-3):325-9. doi: 10.1016/j.cbi.2010.03.001. Epub 2010 Mar 6.
12 Decarboxylases as hypothetical targets for actions of organophosphates: Molecular modeling for prediction of hidden and unexpected health threats. Food Chem Toxicol. 2022 Mar;161:112856. doi: 10.1016/j.fct.2022.112856. Epub 2022 Feb 11.
13 Induction of paraoxonase 1 and apolipoprotein A-I gene expression by aspirin. J Lipid Res. 2008 Oct;49(10):2142-8.