Paraoxon
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Basic Info
| Common Name | Paraoxon(F05615) |
| 2D Structure | |
| Description | Paraoxon is an acetylcholinesterase inhibitor. It is an organophosphate oxon, and the active metabolite of the insecticide parathion. It is also used as an opthamological drug against glaucoma. Paraoxon is one of the most potent acetylcholinesterase-inhibiting insecticides available, around 70% as potent as the nerve agent sarin, and so is now rarely used as an insecticide due to the risk of poisoning to humans and other animals. It is easily absorbed through skin, and was used as an assassination weapon by the apartheid-era South African chemical weapons program Project Coast. |
| FRCD ID | F05615 |
| CAS Number | 311-45-5 |
| PubChem CID | 9395 |
| Formula | C10H14NO6P |
| IUPAC Name | diethyl (4-nitrophenyl) phosphate |
| InChI Key | WYMSBXTXOHUIGT-UHFFFAOYSA-N |
| 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 |
| Canonical SMILES | CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-] |
| Isomeric SMILES | CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-] |
| Wikipedia | Paraoxon |
| Synonyms |
PARAOXON
Diethyl paraoxon
Phosphacol
311-45-5
Ethyl paraoxon
Phosphachole
Mintacol
Diethyl 4-nitrophenyl phosphate
Chinorto
Fosfakol
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Nitrobenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Nitrobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Nitrobenzene - Phenoxy compound - Nitroaromatic compound - Dialkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Alkyl phosphate - C-nitro compound - Organic nitro compound - Organic oxoazanium - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as nitrobenzenes. These are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 275.197 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 6 |
| Complexity | 300 |
| Monoisotopic Mass | 275.056 |
| Exact Mass | 275.056 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 18 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Synthesis, Biological Evaluation, and Docking Studies of Novel Bisquaternary Aldoxime Reactivators on Acetylcholinesterase and Butyrylcholinesterase Inhibited by Paraoxon. | Molecules | 2018 May 7 | 29735900 |
| In silico and in vitro evaluation of two novel oximes (K378 and K727) incomparison to K-27 and pralidoxime against paraoxon-ethyl intoxication. | Toxicol Mech Methods | 2018 Jan | 28722512 |
| A toolbox for microbore liquid chromatography tandem-high-resolution mass spectrometry analysis of albumin-adducts as novel biomarkers of organophosphorus pesticide poisoning. | Toxicol Lett | 2018 Aug | 29702198 |
| A novel fluorimetric sensing platform for highly sensitive detection oforganophosphorus pesticides by using egg white-encapsulated gold nanoclusters. | Biosens Bioelectron | 2017 May 15 | 28012319 |
| Colorimetric biosensor for the assay of paraoxon in environmental water samplesbased on the iodine-starch color reaction. | Anal Chim Acta | 2017 May 15 | 28390486 |
| Graphene modified screen printed immunosensor for highly sensitive detection ofparathion. | Biosens Bioelectron | 2016 Sep 15 | 27135939 |
| Highly-sensitive organophosphorus pesticide biosensors based on CdTe quantum dotsand bi-enzyme immobilized eggshell membranes. | Analyst | 2016 Feb 7 | 26688862 |
| Sensitive Detection of Organophosphorus Pesticides in Medicinal Plants UsingUltrasound-Assisted Dispersive Liquid-Liquid Microextraction Combined withSweeping Micellar Electrokinetic Chromatography. | J Agric Food Chem | 2016 Feb 3 | 26758524 |
| Organophosphorous Pesticide Detection in Olive Oil by Using a Miniaturized,Easy-to-Use, and Cost-Effective Biosensor Combined with QuEChERS for SampleClean-Up. | Sensors (Basel) | 2016 Dec 24 | 28029127 |
| Sensitive fluorescence assay of organophosphorus pesticides based on thefluorescence resonance energy transfer between CdTe quantum dots and porphyrin. | Analyst | 2016 Aug 2 | 27305657 |
| A nano-silver enzyme electrode for organophosphorus pesticide detection. | Anal Bioanal Chem | 2016 Aug | 27342792 |
| Novel approaches to mitigating parathion toxicity: targeting cytochromeP450-mediated metabolism with menadione. | Ann N Y Acad Sci | 2016 Aug | 27441453 |
| An integrated molecular docking and rescoring method for predicting thesensitivity spectrum of various serine hydrolases to organophosphorus pesticides. | J Sci Food Agric | 2016 Apr | 26172068 |
| Stereoselectivity of phosphotriesterase with paraoxon derivatives: acomputational study. | J Biomol Struct Dyn | 2016 | 25929154 |
| Colorimetric and Phosphorimetric Dual-Signaling Strategy Mediated by Inner FilterEffect for Highly Sensitive Assay of Organophosphorus Pesticides. | J Agric Food Chem | 2015 Oct 14 | 26411607 |
| A fluorescence assay for measuring acetylcholinesterase activity in rat blood anda human neuroblastoma cell line (SH-SY5Y). | J Pharmacol Toxicol Methods | 2015 Nov-Dec | 26165232 |
| Efficient immobilization of acetylcholinesterase onto amino functionalized carbonnanotubes for the fabrication of high sensitive organophosphorus pesticidesbiosensors. | Biosens Bioelectron | 2015 Jun 15 | 25594160 |
| Paper-based acetylcholinesterase inhibition assay combining a wet system fororganophosphate and carbamate pesticides detection. | EXCLI J | 2015 Feb 26 | 26417364 |
| Nanostructured photoelectrochemical biosensor for highly sensitive detection oforganophosphorous pesticides. | Biosens Bioelectron | 2015 Feb 15 | 25173731 |
| Based on time and spatial-resolved SERS mapping strategies for detection ofpesticides. | Talanta | 2015 Aug 15 | 25966372 |
Targets
- Specific Function:
- Keratin-binding protein required for epithelial cell polarization. Involved in apical junction complex (AJC) assembly via its interaction with PARD3. Required for ciliogenesis.
- Gene Name:
- FBF1
- Uniprot ID:
- Q8TES7
- Molecular Weight:
- 125445.19 Da
References
- Peeples ES, Schopfer LM, Duysen EG, Spaulding R, Voelker T, Thompson CM, Lockridge O: Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry. Toxicol Sci. 2005 Feb;83(2):303-12. Epub 2004 Nov 3. [15525694 ]
- General Function:
- Oxygen binding
- Specific Function:
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name:
- CYP19A1
- Uniprot ID:
- P11511
- Molecular Weight:
- 57882.48 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Identical protein binding
- Specific Function:
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name:
- BCHE
- Uniprot ID:
- P06276
- Molecular Weight:
- 68417.575 Da
References
- Petroianu G, Kuhn F, Thyes C, Ewald V, Missler A: In vitro protection of plasma cholinesterases by metoclopramide from inhibition by paraoxon. J Appl Toxicol. 2003 Jan-Feb;23(1):75-9. [12518340 ]
- General Function:
- Cation transmembrane transporter activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNE
- Uniprot ID:
- Q04844
- Molecular Weight:
- 54696.54 Da
References
- Radic Z, Sit RK, Garcia E, Zhang L, Berend S, Kovarik Z, Amitai G, Fokin VV, Barry Sharpless K, Taylor P: Mechanism of interaction of novel uncharged, centrally active reactivators with OP-hAChE conjugates. Chem Biol Interact. 2013 Mar 25;203(1):67-71. doi: 10.1016/j.cbi.2012.08.014. Epub 2012 Sep 4. [22975155 ]