Methyl parathion (BioDeep_00000001404)

 

Secondary id: BioDeep_00001871698

human metabolite blood metabolite Industrial Pollutants


代谢物信息卡片


Phosphorothioic acid, O,O-dimethyl O-(4-nitrophenyl) ester

化学式: C8H10NO5PS (263.00173)
中文名称: 甲基对硫磷
谱图信息: 最多检出来源 Homo sapiens(blood) 0.08%

Reviewed

Last reviewed on 2024-08-21.

Cite this Page

Methyl parathion. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/methyl_parathion (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000001404). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: COP(=S)(OC)OC1=CC=C(C=C1)[N+](=O)[O-]
InChI: InChI=1S/C8H10NO5PS/c1-12-15(16,13-2)14-8-5-3-7(4-6-8)9(10)11/h3-6H,1-2H3

描述信息

Methyl parathion is an insecticide that does not occur naturally in the environment. Pure methyl parathion exists as white crystals. Impure methyl parathion is a brownish liquid that smells like rotten eggs.Methyl parathion is used to kill insects on farm crops, especially cotton. The EPA now restricts how methyl parathion can be used and applied; only trained people are allowed to spray it. Methyl parathion can no longer be used on food crops commonly consumed by children.

Methyl parathion is a white crystalline solid which is often dissolved in a liquid solvent carrier. The commercial product is a tan liquid (xylene solution) with a pungent odor. It is slightly soluble to insoluble in water. Usually with the liquid solvent it is a combustible liquid. It is toxic by inhalation, ingestion and skin absorption. It is used as an insecticide.

Parathion-methyl is a C-nitro compound that is 4-nitrophenol substituted by a (dimethoxyphosphorothioyl)oxy group at position 4. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an acaricide, an agrochemical, a genotoxin, an environmental contaminant and an antifungal agent. It is an organic thiophosphate, an organothiophosphate insecticide and a C-nitro compound. It is functionally related to a 4-nitrophenol.

同义名列表

21 个代谢物同义名

Phosphorothioic acid, O,O-dimethyl O-(4-nitrophenyl) ester; Phosphorothioic acid, O,O-dimethyl-O-p-nitrophenyl ester; Phosphorothioate, O,O-dimethyl O-(4-nitrophenyl) ester; Phosphorothioate, O,O-dimethyl-O-p-nitrophenyl ester; O,O-Dimethyl O-(p-nitrophenyl) thionophosphoric acid; O,O-Dimethyl O-(p-nitrophenyl) thionophosphate; O,O-dimethyl O-4-nitrophenyl phosphorothioate; Dimethyl p-nitrophenyl thiophosphoric acid; Dimethyl p-nitrophenyl thiophosphate; Dimethyl parathion; METHYL PARATHIONE; Parathion-methyl; Methyl parathion; Parathion methyl; Methylparathion; Metacid 50; Metaphos; Wofatox; Vofatox; α-gro; Dalf



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

6 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(6)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Rafael J G Rubira, Victor R G Batista, Rafael R Correia, Wallance M Pazin, Mateus D Maximino, Gilia C M Ruiz, Giovana R Teixeira, Aldo E Job. Biological responses to imazapic and methyl parathion pesticides in bioinspired lipid membranes and Tilapia fish. Journal of hazardous materials. 2023 09; 458(?):131943. doi: 10.1016/j.jhazmat.2023.131943. [PMID: 37390683]
  • Shivani Chhillar, Vipul Batra, Arumugam Kumaresan, Rakesh Kumar, Ankit Pal, Tirtha Kumar Datta. Acute exposure to organophosphorus pesticide metabolites compromises buffalo sperm function and impairs fertility. Scientific reports. 2023 06; 13(1):9102. doi: 10.1038/s41598-023-35541-6. [PMID: 37277402]
  • Zhao Ma, Yuanbo Li, Chao Lu, Meng Li. On-site screening method for bioavailability assessment of the organophosphorus pesticide, methyl parathion, and its primary metabolite in soils by paper strip biosensor. Journal of hazardous materials. 2023 May; 457(?):131725. doi: 10.1016/j.jhazmat.2023.131725. [PMID: 37295330]
  • Hongyuan Zhao, Bo Li, Runqiang Liu, Yuqi Chang, Hongliang Wang, Lin Zhou, Sridhar Komarneni. Ultrasonic-assisted preparation of halloysite nanotubes/zirconia/carbon black nanocomposite for the highly sensitive determination of methyl parathion. Materials science & engineering. C, Materials for biological applications. 2021 Apr; 123(?):111982. doi: 10.1016/j.msec.2021.111982. [PMID: 33812610]
  • Huiyu Zhao, Barbara Bojko, Fengmao Liu, Janusz Pawliszyn, Wei Peng, Xinquan Wang. Mechanism of interactions between organophosphorus insecticides and human serum albumin: Solid-phase microextraction, thermodynamics and computational approach. Chemosphere. 2020 Aug; 253(?):126698. doi: 10.1016/j.chemosphere.2020.126698. [PMID: 32302901]
  • Mayrut Urióstegui-Acosta, Pamela Tello-Mora, María de Jesús Solís-Heredia, José Mario Ortega-Olvera, Belem Piña-Guzmán, Dolores Martín-Tapia, Lorenza González-Mariscal, Betzabet Quintanilla-Vega. Methyl parathion causes genetic damage in sperm and disrupts the permeability of the blood-testis barrier by an oxidant mechanism in mice. Toxicology. 2020 05; 438(?):152463. doi: 10.1016/j.tox.2020.152463. [PMID: 32294493]
  • Michael Eddleston, R Eddie Clutton, Matthew Taylor, Adrian Thompson, Franz Worek, Harald John, Horst Thiermann, Colin Scott. Efficacy of an organophosphorus hydrolase enzyme (OpdA) in human serum and minipig models of organophosphorus insecticide poisoning. Clinical toxicology (Philadelphia, Pa.). 2020 05; 58(5):397-405. doi: 10.1080/15563650.2019.1655149. [PMID: 31452424]
  • Lindsay M Jaacks, Nancy Diao, Antonia M Calafat, Maria Ospina, Maitreyi Mazumdar, Md Omar Sharif Ibne Hasan, Robert Wright, Quazi Quamruzzaman, David C Christiani. Association of prenatal pesticide exposures with adverse pregnancy outcomes and stunting in rural Bangladesh. Environment international. 2019 12; 133(Pt B):105243. doi: 10.1016/j.envint.2019.105243. [PMID: 31675560]
  • T H Vignesh Kumar, Ashok K Sundramoorthy. Electrochemical biosensor for methyl parathion based on single-walled carbon nanotube/glutaraldehyde crosslinked acetylcholinesterase-wrapped bovine serum albumin nanocomposites. Analytica chimica acta. 2019 Oct; 1074(?):131-141. doi: 10.1016/j.aca.2019.05.011. [PMID: 31159933]
  • Huixiang Wu, Yi Luo, Changjun Hou, Danqun Huo, Weilu Wang, Jing Zhao, Yu Lei. Rapid and fingerprinted monitoring of pesticide methyl parathion on the surface of fruits/leaves as well as in surface water enabled by gold nanorods based casting-and-sensing SERS platform. Talanta. 2019 Aug; 200(?):84-90. doi: 10.1016/j.talanta.2019.03.004. [PMID: 31036229]
  • Tehseen Yaseen, Hongbin Pu, Da-Wen Sun. Rapid detection of multiple organophosphorus pesticides (triazophos and parathion-methyl) residues in peach by SERS based on core-shell bimetallic Au@Ag NPs. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2019 May; 36(5):762-778. doi: 10.1080/19440049.2019.1582806. [PMID: 30943113]
  • Youping Wang, Cheng Liu, Juan Wan, Xiaowen Sun, Wei Ma, Hong Ni. Molecular cloning and characterization of a methyl parathion hydrolase from an organophosphorus-degrading bacterium, Serratia marcescens MEW06. FEMS microbiology letters. 2018 12; 365(24):. doi: 10.1093/femsle/fny279. [PMID: 30476043]
  • Fuying Du, Ying-Sing Fung. Dual-opposite multi-walled carbon nanotube modified carbon fiber microelectrode for microfluidic chip-capillary electrophoresis determination of methyl parathion metabolites in human urine. Electrophoresis. 2018 06; 39(11):1375-1381. doi: 10.1002/elps.201700470. [PMID: 29500834]
  • Victor Hugo Fuentes-Delgado, María Consolación Martínez-Saldaña, María Luisa Rodríguez-Vázquez, Miguel Arturo Reyes-Romero, José Luis Reyes-Sánchez, Fernando Jaramillo-Juárez. Renal damage induced by the pesticide methyl parathion in male Wistar rats. Journal of toxicology and environmental health. Part A. 2018; 81(6):130-141. doi: 10.1080/15287394.2017.1394948. [PMID: 29319433]
  • A Ojha, Y K Gupta. Study of commonly used organophosphate pesticides that induced oxidative stress and apoptosis in peripheral blood lymphocytes of rats. Human & experimental toxicology. 2017 Nov; 36(11):1158-1168. doi: 10.1177/0960327116680273. [PMID: 27941166]
  • Irma Martha Medina-Díaz, Néstor Ponce-Ruiz, Bryana Ramírez-Chávez, Aurora Elizabeth Rojas-García, Briscia S Barrón-Vivanco, Guillermo Elizondo, Yael Y Bernal-Hernández. Downregulation of human paraoxonase 1 (PON1) by organophosphate pesticides in HepG2 cells. Environmental toxicology. 2017 Feb; 32(2):490-500. doi: 10.1002/tox.22253. [PMID: 26948828]
  • Jing Bao, Changjun Hou, Qiuchen Dong, Xiaoyu Ma, Jun Chen, Danqun Huo, Mei Yang, Khaled Hussein Abd El Galil, Wilfred Chen, Yu Lei. ELP-OPH/BSA/TiO2 nanofibers/c-MWCNTs based biosensor for sensitive and selective determination of p-nitrophenyl substituted organophosphate pesticides in aqueous system. Biosensors & bioelectronics. 2016 Nov; 85(?):935-942. doi: 10.1016/j.bios.2016.05.094. [PMID: 27315519]
  • Pragyan Dubey, Amit Kumar Mishra, Ashok Kumar Singh. Comparative analyses of genotoxicity, oxidative stress and antioxidative defence system under exposure of methyl parathion and hexaconazole in barley (Hordeum vulgare L.). Environmental science and pollution research international. 2015 Dec; 22(24):19848-59. doi: 10.1007/s11356-015-5216-x. [PMID: 26286802]
  • Sanjay Vikrant. Hepato-renal toxicity-associated with methyl parathion exposure. Renal failure. 2015 Mar; 37(2):355-6. doi: 10.3109/0886022x.2014.986620. [PMID: 25410113]
  • Xiangjiang Tang, Bo Liang, Tuyong Yi, Giuseppe Manco, Ilaria Palchetti, Ilariapalchetti, Aihua Liu. Cell surface display of organophosphorus hydrolase for sensitive spectrophotometric detection of p-nitrophenol substituted organophosphates. Enzyme and microbial technology. 2014 Feb; 55(?):107-12. doi: 10.1016/j.enzmictec.2013.10.006. [PMID: 24411452]
  • Anupama Ojha, Santosh Kumar Yaduvanshi, Satish Chnadra Pant, Vinay Lomash, Nalini Srivastava. Evaluation of DNA damage and cytotoxicity induced by three commonly used organophosphate pesticides individually and in mixture, in rat tissues. Environmental toxicology. 2013 Oct; 28(10):543-52. doi: 10.1002/tox.20748. [PMID: 21786386]
  • Falicia L Edwards, Clement G Yedjou, Paul B Tchounwou. Involvement of oxidative stress in methyl parathion and parathion-induced toxicity and genotoxicity to human liver carcinoma (HepG₂) cells. Environmental toxicology. 2013 Jun; 28(6):342-8. doi: 10.1002/tox.20725. [PMID: 21544925]
  • Xue-Ping Ling, Ying-Hua Lu, He-Qing Huang. Differential protein profile in zebrafish (Danio rerio) brain under the joint exposure of methyl parathion and cadmium. Environmental science and pollution research international. 2012 Nov; 19(9):3925-41. doi: 10.1007/s11356-012-1037-3. [PMID: 22767353]
  • Xiang Huang, He-Qing Huang. Alteration of the kidney membrane proteome of Mizuhopecten yessoensis induced by low-level methyl parathion exposure. Aquatic toxicology (Amsterdam, Netherlands). 2012 Jun; 114-115(?):189-99. doi: 10.1016/j.aquatox.2012.01.025. [PMID: 22446831]
  • Laura E Lange, S Kay Obendorf. Effect of plasma etching on destructive adsorption properties of polypropylene fibers containing magnesium oxide nanoparticles. Archives of environmental contamination and toxicology. 2012 Feb; 62(2):185-94. doi: 10.1007/s00244-011-9702-y. [PMID: 21850511]
  • Wensheng Lan, Guoping Chen, Feng Cui, Feng Tan, Ran Liu, Maolidan Yushupujiang. Development of a novel optical biosensor for detection of organophosphorus pesticides based on methyl parathion hydrolase immobilized by metal-chelate affinity. Sensors (Basel, Switzerland). 2012; 12(7):8477-90. doi: 10.3390/s120708477. [PMID: 23012501]
  • Meltem Uzunhisarcikli, Yusuf Kalender. Protective effects of vitamins C and E against hepatotoxicity induced by methyl parathion in rats. Ecotoxicology and environmental safety. 2011 Oct; 74(7):2112-8. doi: 10.1016/j.ecoenv.2011.07.001. [PMID: 21782244]
  • Yuan Du, Tian Wang, Na Jiang, Ru-Tong Ren, De-Lu Zhao, Chong Li, Feng-Hua Fu. Protective effect of sodium aescinate on lung injury induced by methyl parathion. Human & experimental toxicology. 2011 Oct; 30(10):1584-91. doi: 10.1177/0960327110393764. [PMID: 21177729]
  • Jitendra Kumar, S F D'Souza. Immobilization of microbial cells on inner epidermis of onion bulb scale for biosensor application. Biosensors & bioelectronics. 2011 Jul; 26(11):4399-404. doi: 10.1016/j.bios.2011.04.049. [PMID: 21605968]
  • Dau Hung Anh, Kritsananporn Cheunrungsikul, Jesdawan Wichitwechkarn, Werasak Surareungchai. A colorimetric assay for determination of methyl parathion using recombinant methyl parathion hydrolase. Biotechnology journal. 2011 May; 6(5):565-71. doi: 10.1002/biot.201000348. [PMID: 21381204]
  • Yingxia Yue, Lun Li, Yong Liang, Linjie Dong, Qingjian Dong, Hongying Zhong. Effects of co-existed proteins on measurement of pesticide residues in blood by gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Nov; 878(30):3089-94. doi: 10.1016/j.jchromb.2010.09.013. [PMID: 20970391]
  • Dilson Silva, Madelayne Cortez-Moreira, Vera Lúcia Freire Cunha Bastos, Jayme Cunha Bastos, Célia Martins Cortez. Spectrofluorimetric study of the interaction of methyl-parathion with fish serum albumin. Fish physiology and biochemistry. 2010 Sep; 36(3):427-433. doi: 10.1007/s10695-009-9312-z. [PMID: 19294526]
  • Chip Gresham, Christopher Rosenbaum, Romolo J Gaspari, Colin J Jackson, Steven B Bird. Kinetics and efficacy of an organophosphorus hydrolase in a rodent model of methyl-parathion poisoning. Academic emergency medicine : official journal of the Society for Academic Emergency Medicine. 2010 Jul; 17(7):736-40. doi: 10.1111/j.1553-2712.2010.00798.x. [PMID: 20653588]
  • Na Jiang, Lina Lu, Tian Wang, Leiming Zhang, Wenyu Xin, Fenghua Fu. Reduced glutathione attenuates liver injury induced by methyl parathion in rats. Toxicology mechanisms and methods. 2010 Feb; 20(2):69-74. doi: 10.3109/15376510903575782. [PMID: 20100039]
  • Dilson Silva, Madelayne Cortez-Moreira, Vera L F Cunha Bastos, Jayme Cunha Bastos, Célia Martins Cortez. The interaction of methyl-parathion with serum and albumin of the neo-tropical fish Piaractus mesopotamicus. Ecotoxicology and environmental safety. 2010 Jan; 73(1):32-7. doi: 10.1016/j.ecoenv.2009.09.003. [PMID: 19800687]
  • Susmita Ganguly, Sima Bhattacharya, Sukumar Mandi, Jayanta Tarafdar. Biological detection and analysis of toxicity of organophosphate- and azadirachtin-based insecticides in Lathyrus sativus L. Ecotoxicology (London, England). 2010 Jan; 19(1):85-95. doi: 10.1007/s10646-009-0391-5. [PMID: 19618265]
  • Parinya Panuwet, Tippawan Prapamontol, Somporn Chantara, Prasak Thavornyuthikarn, Roberto Bravo, Paula Restrepo, Robert D Walker, Bryan L Williams, Larry L Needham, Dana B Barr. Urinary paranitrophenol, a metabolite of methyl parathion, in Thai farmer and child populations. Archives of environmental contamination and toxicology. 2009 Oct; 57(3):623-9. doi: 10.1007/s00244-009-9315-x. [PMID: 19365648]
  • Melpomeni Tryfonos, Chrisovalantis Papaefthimiou, Efthimia Antonopoulou, George Theophilidis. Comparing the inhibitory effects of five protoxicant organophosphates (azinphos-methyl, parathion-methyl, chlorpyriphos-methyl, methamidophos and diazinon) on the spontaneously beating auricle of Sparus aurata: an in vitro study. Aquatic toxicology (Amsterdam, Netherlands). 2009 Sep; 94(3):211-8. doi: 10.1016/j.aquatox.2009.07.003. [PMID: 19674799]
  • B Piña-Guzmán, M Sánchez-Gutiérrez, F Marchetti, I Hernández-Ochoa, M J Solís-Heredia, B Quintanilla-Vega. Methyl-parathion decreases sperm function and fertilization capacity after targeting spermatocytes and maturing spermatozoa. Toxicology and applied pharmacology. 2009 Jul; 238(2):141-9. doi: 10.1016/j.taap.2009.05.008. [PMID: 19442678]
  • Leonardo Cericato, Joaquim Gonçalves Machado Neto, Luiz Carlos Kreutz, Rosmari Mezzalira Quevedo, João Gabriel Santos da Rosa, Gessi Koakoski, Lucas Centenaro, Emanuele Pottker, Alessandra Marqueze, Leonardo José Gil Barcellos. Responsiveness of the interrenal tissue of Jundiá (Rhamdia quelen) to an in vivo ACTH test following acute exposure to sublethal concentrations of agrichemicals. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2009 Apr; 149(3):363-7. doi: 10.1016/j.cbpc.2008.09.002. [PMID: 18824247]
  • Diana Amaral Monteiro, Francisco Tadeu Rantin, Ana Lúcia Kalinin. The effects of selenium on oxidative stress biomarkers in the freshwater characid fish matrinxã, Brycon cephalus (Günther, 1869) exposed to organophosphate insecticide Folisuper 600 BR (methyl parathion). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2009 Jan; 149(1):40-9. doi: 10.1016/j.cbpc.2008.06.012. [PMID: 18655848]
  • Richard P Moody, Anna Yip, Ih Chu. Effect of cold storage on in vitro human skin absorption of six 14C-radiolabeled environmental contaminants: benzo[a]pyrene, ethylene glycol, methyl parathion, naphthalene, nonyl phenol, and toluene. Journal of toxicology and environmental health. Part A. 2009; 72(8):505-17. doi: 10.1080/15287390802328713. [PMID: 19267311]
  • Guifang Jia, Chunguang Lv, Wentao Zhu, Jing Qiu, Xinquan Wang, Zhiqiang Zhou. Applicability of cloud point extraction coupled with microwave-assisted back-extraction to the determination of organophosphorous pesticides in human urine by gas chromatography with flame photometry detection. Journal of hazardous materials. 2008 Nov; 159(2-3):300-5. doi: 10.1016/j.jhazmat.2008.02.081. [PMID: 18468789]
  • Saumen Kumar Maitra, Anindita Mitra. Testicular functions and serum titers of LH and testosterone in methyl parathion-fed roseringed parakeets. Ecotoxicology and environmental safety. 2008 Sep; 71(1):236-44. doi: 10.1016/j.ecoenv.2007.09.002. [PMID: 18029014]
  • Ismail Celik, Huseyin Suzek. Subacute effects of methyl parathion on antioxidant defense systems and lipid peroxidation in rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2008 Aug; 46(8):2796-801. doi: 10.1016/j.fct.2008.05.012. [PMID: 18571824]
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  • B Piña-Guzmán, M J Solís-Heredia, A E Rojas-García, M Urióstegui-Acosta, B Quintanilla-Vega. Genetic damage caused by methyl-parathion in mouse spermatozoa is related to oxidative stress. Toxicology and applied pharmacology. 2006 Oct; 216(2):216-24. doi: 10.1016/j.taap.2006.05.001. [PMID: 16784764]
  • Ping Liu, Xiaoxiao Song, Weihong Yuan, Weihua Wen, Xinan Wu, Jian Li, Xuemin Chen. Effects of cypermethrin and methyl parathion mixtures on hormone levels and immune functions in Wistar rats. Archives of toxicology. 2006 Jul; 80(7):449-57. doi: 10.1007/s00204-006-0071-7. [PMID: 16496128]
  • Hui-fang Yan, Ya-juan Pan, Jian Wang, Fu-gang Zhang, Xiao-shuang Xie, Jing Zhang, Chun-ling Li. [High performance thin layer chromatography quality assessment of Rogor, methyl parathion, methamidophos and dichlorvos in serum]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2006 Jul; 24(7):437-8. doi: NULL. [PMID: 16889713]
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  • Diana Amaral Monteiro, Jeane Alves de Almeida, Francisco Tadeu Rantin, Ana Lúcia Kalinin. Oxidative stress biomarkers in the freshwater characid fish, Brycon cephalus, exposed to organophosphorus insecticide Folisuper 600 (methyl parathion). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2006 Jun; 143(2):141-9. doi: 10.1016/j.cbpc.2006.01.004. [PMID: 16546452]
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