Paraoxon (BioCAD00000015880)
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Metabolite Card
Formula: C10H14NO6P (275.0559)
SMILES: CCOP(=O)(OCC)OC1=CC=C(C=C1)[N+]([O-])=O
Synonyms [en]
Paraoxon; Diethyl paraoxon; O,O-Diethyl-O-p-nitrophenylphosphoric acid; Diethyl 4-nitrophenyl phosphate; Ethyl paraoxon; Phosphoric acid diethyl 4-nitrophenyl ester
Last reviewed on 2024-06-28.
Cite this Page
Paraoxon. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000015880). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
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.
DBLinks
- CAS Registry Number: 311-45-5
- PubChem CID: 9395
- ChEBI: 27827
- HMDB: HMDB0013035
- LipidMaps:
- KEGG: C06606
- BioCyc: PARAOXON
- NCBI MeSH: Paraoxon
- Wikipedia: Paraoxon
Other DBLinks
- CAS Registry Number: 311-45-5
- PubChem: 9395
- ChEBI: ChEBI:27827
- HMDB: HMDB0013035
- HMDB: HMDB13035
- KEGG: C06606
- BioCyc: PARAOXON
- NCBI MeSH: Paraoxon
- Wikipedia: Paraoxon
- DrugBank: DB13495
- RefMet: RM0199410
- MoNA: FiehnHILIC000657
- MoNA: FiehnHILIC001433
- MoNA: FiehnHILIC002225
- MoNA: HMDB0013035_c_ms_100034
- Metlin: METLIN_44800
- Coconut NaturalProduct: CNP0580731.0
Class / Ontology
- WishartLab ClassyFire: [Nitrobenzenes] Nitrobenzenes
- RefMet: [Nitrobenzenes] Nitrobenzenes
- ChEBI: [CHEBI:27827] paraoxon
| ID | EC Number | Name |
|---|---|---|
| KEGG:R05259 | 1.14.14.1 | parathion,NADPH---hemoprotein reductase:oxygen oxidoreductase (paraoxon-forming) |
| KEGG:R05548 | 3.1.8.1 | C06606 + C00001<=>C06608 + C00870 |
| KEGG:R08579 | 1.14.-.- | parathion oxidoreductase |
| Rhea:RHEA:18054 | 3.1.8.1 | paraoxon + H2O => diethylphosphate + 4-nitrophenol + 2 H+ |
| Rhea:RHEA:18055 | 3.1.8.1 | diethylphosphate + 4-nitrophenol + 2 H+ => paraoxon + H2O |
| Rhea:RHEA:18056 | 3.1.8.1 | paraoxon + H2O <=> diethylphosphate + 4-nitrophenol + 2 H+ |
| BioCyc:RXN-8746 | 3.1.8.1 | PARAOXON + WATER --> DIETHYLPHOSPHATE + P-NITROPHENOL + 2 PROTON |
| BioCyc:RXN-20736 | PARATHION + OXYGEN-MOLECULE + 2 Red-NADPH-Hemoprotein-Reductases --> PARAOXON + WATER + HS + 2 Ox-NADPH-Hemoprotein-Reductases |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:META_LIPAS-PWY | triacylglycerol degradation |
| BioCyc:MTBCDC1551_PWY-5490 | paraoxon degradation |
| BioCyc:MOUSE_PWY-5490 | paraoxon degradation |
| BioCyc:FLY_PWY-5490 | paraoxon degradation |
| BioCyc:MTBH37RV_PWY-5490 | paraoxon degradation |
| BioCyc:10403S_RAST_PWY-5490 | paraoxon degradation |
| BioCyc:META_PWY-5490 | paraoxon degradation |