Chlorpyrifos-methyl (BioDeep_00000002195)

   

human metabolite blood metabolite


代谢物信息卡片


Phosphorothioic acid, O,O-dimethyl O-(3,5,6-trichloro-2-pyridinyl) ester

化学式: C7H7Cl3NO3PS (320.89498520000006)
中文名称: 甲基毒死蜱
谱图信息: 最多检出来源 Homo sapiens(blood) 50%

分子结构信息

SMILES: Clc1c(OP(=S)(OC)OC)nc(Cl)c(Cl)c1
InChI: InChI=1S/C7H7Cl3NO3PS/c1-12-15(16,13-2)14-7-5(9)3-4(8)6(10)11-7/h3H,1-2H3

描述信息

C471 - Enzyme Inhibitor > C47792 - Acetylcholinesterase Inhibitor
CONFIDENCE standard compound; EAWAG_UCHEM_ID 2951

同义名列表

19 个代谢物同义名

Phosphorothioic acid, O,O-dimethyl O-(3,5,6-trichloro-2-pyridinyl) ester; Phosphorothioic acid, O,O-dimethyl O-(3,5,6-trichloro-2-pyridyl) ester; Phosphorothioate, O,O-dimethyl O-(3,5,6-trichloro-2-pyridinyl) ester; Phosphorothioate, O,O-dimethyl O-(3,5,6-trichloro-2-pyridyl) ester; O,O-Dimethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphoric acid; O,O-Dimethyl O-(3,5,6-trichloro-2-pyridyl) phosphorothioic acid; O,O-Dimethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioic acid; O,O-Dimethyl O-(3,5,6-trichloro-2-pyridyl) phosphorothioate; O,O-dimethyl O-3,5,6-trichloropyridin-2-yl phosphorothioate; O,O-Dimethyl O-(3,5,6-trichloropyridin-2-yl) thiophosphate; O,O-Dimethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate; Chlorpyrifos O,O-dimethyl analog; Chloropyriphos-methyl; Methyl chlorpyriphos; Chlorpyrifos-methyl; Methyl chlorpyrifos; Trichlormethylfos; dowco 214; Reldan



数据库引用编号

26 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

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

  • Rubing Zou, Yuanhao Guo, Yan Wang, Xinying Lu, Zhongjie Ma, Linfei Shou, Yihua Liu, Guonian Zhu, Yirong Guo. Insights into the Binding Profile of Anti-chlorpyrifos Recombinant Antibodies: From Computational Simulation to Immunoassay Validation. Analytical chemistry. 2023 08; 95(30):11287-11295. doi: 10.1021/acs.analchem.3c01355. [PMID: 37459591]
  • Johann G Zaller, Andreas Oswald, Martin Wildenberg, Helmut Burtscher-Schaden, Imran Nadeem, Herbert Formayer, Daniel Paredes. Potential to reduce pesticides in intensive apple production through management practices could be challenged by climatic extremes. The Science of the total environment. 2023 Feb; ?(?):162237. doi: 10.1016/j.scitotenv.2023.162237. [PMID: 36796687]
  • Elisabeth Holen, Marit Espe, Anett K Larsen, Pål A Olsvik. Dietary chlorpyrifos-methyl exposure impair transcription of immune-, detoxification- and redox signaling genes in leukocytes isolated from cod (Gadus morhua). Fish & shellfish immunology. 2022 Aug; 127(?):549-560. doi: 10.1016/j.fsi.2022.06.060. [PMID: 35803506]
  • Ayşegül Duman, Osman Tiryaki. Determination of chlorpyrifos-methyl, lambda-cyhalothrin and tebuconazole residues in Sultana seedless grapes sprayed with pesticides under farmer's conditions. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2022; 57(4):325-332. doi: 10.1080/03601234.2022.2051415. [PMID: 35293832]
  • Khaled A Osman, Eslam M Ezz El-Din, Nabila S Ahmed, Ayman S El-Seedy. Effect of N-acetylcysteine on attenuation of chlropyrifos and its methyl analogue toxicity in male rats. Toxicology. 2021 09; 461(?):152904. doi: 10.1016/j.tox.2021.152904. [PMID: 34425170]
  • Lydia Kuhnert, Mery Giantin, Mauro Dacasto, Sandra Halwachs, Walther Honscha. AhR-activating pesticides increase the bovine ABCG2 efflux activity in MDCKII-bABCG2 cells. PloS one. 2020; 15(8):e0237163. doi: 10.1371/journal.pone.0237163. [PMID: 32764792]
  • Bing Yang, Chao Qin, Xiaojie Hu, Kang Xia, Chao Lu, Fredrick Owino Gudda, Zhao Ma, Yanzheng Gao. Enzymatic degradation of extracellular DNA exposed to chlorpyrifos and chlorpyrifos-methyl in an aqueous system. Environment international. 2019 11; 132(?):105087. doi: 10.1016/j.envint.2019.105087. [PMID: 31430607]
  • Borja Garlito, María Ibáñez, Tania Portolés, Roque Serrano, Heidi Amlund, Anne-Katrine Lundebye, Monica Sanden, Marc H G Berntssen, Félix Hernández. LC-MS/MS method for the determination of organophosphorus pesticides and their metabolites in salmon and zebrafish fed with plant-based feed ingredients. Analytical and bioanalytical chemistry. 2019 Nov; 411(27):7281-7291. doi: 10.1007/s00216-019-02104-6. [PMID: 31608426]
  • P A Olsvik, M H G Berntssen, L Søfteland, M Sanden. Transcriptional effects of dietary chlorpyrifos‑methyl exposure in Atlantic salmon (Salmo salar) brain and liver. Comparative biochemistry and physiology. Part D, Genomics & proteomics. 2019 03; 29(?):43-54. doi: 10.1016/j.cbd.2018.11.003. [PMID: 30419482]
  • Tatsunori Takayasu, Hiroki Yamamoto, Yuko Ishida, Mizuho Nosaka, Mariko Kawaguchi, Yumi Kuninaka, Akihiko Kimura, Toshikazu Kondo. Postmortem distribution of chlorpyrifos-methyl, fenitrothion, and their metabolites in body fluids and organ tissues of an intoxication case. Legal medicine (Tokyo, Japan). 2017 Nov; 29(?):44-50. doi: 10.1016/j.legalmed.2017.10.002. [PMID: 29054069]
  • Martina Beránková, Jarmila Hojerová, Linda Melegová. Exposure of amateur gardeners to pesticides via the non-gloved skin per day. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2017 Oct; 108(Pt A):224-235. doi: 10.1016/j.fct.2017.07.060. [PMID: 28778749]
  • T Portolés, M Ibáñez, B Garlito, J Nácher-Mestre, V Karalazos, J Silva, M Alm, R Serrano, J Pérez-Sánchez, F Hernández, M H G Berntssen. Comprehensive strategy for pesticide residue analysis through the production cycle of gilthead sea bream and Atlantic salmon. Chemosphere. 2017 Jul; 179(?):242-253. doi: 10.1016/j.chemosphere.2017.03.099. [PMID: 28371708]
  • Ewa Szpyrka, Aneta Matyaszek, Magdalena Słowik-Borowiec. Dissipation of chlorantraniliprole, chlorpyrifos-methyl and indoxacarb-insecticides used to control codling moth (Cydia Pomonella L.) and leafrollers (Tortricidae) in apples for production of baby food. Environmental science and pollution research international. 2017 May; 24(13):12128-12135. doi: 10.1007/s11356-017-8821-z. [PMID: 28349309]
  • Ahmed M Abu El-Saad, Dalia A Kheirallah, Lamia M El-Samad. Biochemical and histological biomarkers in the midgut of Apis mellifera from polluted environment at Beheira Governorate, Egypt. Environmental science and pollution research international. 2017 Jan; 24(3):3181-3193. doi: 10.1007/s11356-016-8059-1. [PMID: 27864738]
  • Recep Dokuyucu, Ali Bilgili, Basak Hanedan, Hatice Dogan, Ahmet Dokuyucu, Muhammed Murat Celik. Attenuating effects of caffeic acid phenethyl ester with intralipid on hepatotoxicity of chlorpyrifos in the case of rats. Medycyna pracy. 2016 Dec; 67(6):743-749. doi: 10.13075/mp.5893.00462. [PMID: 28005083]
  • Lei Wang, Zhen Liu, Junjie Zhang, Yinghong Wu, Hongwen Sun. Chlorpyrifos exposure in farmers and urban adults: Metabolic characteristic, exposure estimation, and potential effect of oxidative damage. Environmental research. 2016 08; 149(?):164-170. doi: 10.1016/j.envres.2016.05.011. [PMID: 27208467]
  • Yongfeng Deng, Yan Zhang, Yifeng Lu, Yanping Zhao, Hongqiang Ren. Hepatotoxicity and nephrotoxicity induced by the chlorpyrifos and chlorpyrifos-methyl metabolite, 3,5,6-trichloro-2-pyridinol, in orally exposed mice. The Science of the total environment. 2016 Feb; 544(?):507-14. doi: 10.1016/j.scitotenv.2015.11.162. [PMID: 26674679]
  • Hirotaka Sato, Yuki Ito, Jun Ueyama, Yuya Kano, Tomoya Arakawa, Masahiro Gotoh, Takaaki Kondo, Yuka Sugiura, Isao Saito, Eiji Shibata, Michihiro Kamijima. Effects of Paraoxonase 1 gene polymorphisms on organophosphate insecticide metabolism in Japanese pest control workers. Journal of occupational health. 2016; 58(1):56-65. doi: 10.1539/joh.15-0175-oa. [PMID: 26549836]
  • Hyo-Sook Shin, Jong-Hun Seo, Sang-Hee Jeong, Sung-Won Park, Young-Il Park, Seong-Wan Son, Hwan-Goo Kang, Jin Suk Kim. Effect on the H19 gene methylation of sperm and organs of offspring after chlorpyrifos-methyl exposure during organogenesis period. Environmental toxicology. 2015 Dec; 30(12):1355-63. doi: 10.1002/tox.21923. [PMID: 25782373]
  • Jiyuan Liu, Xueqing Yang, Yalin Zhang. Characterization of a lambda-cyhalothrin metabolizing glutathione S-transferase CpGSTd1 from Cydia pomonella (L.). Applied microbiology and biotechnology. 2014 Nov; 98(21):8947-62. doi: 10.1007/s00253-014-5786-4. [PMID: 24827500]
  • Hyo-Sook Shin, Jong-Hun Seo, Sang-Hee Jeong, Sung-Won Park, Youngil Park, Seong-Wan Son, Jin Suk Kim, Hwan-Goo Kang. Exposure of pregnant mice to chlorpyrifos-methyl alters embryonic H19 gene methylation patterns. Environmental toxicology. 2014 Aug; 29(8):926-35. doi: 10.1002/tox.21820. [PMID: 23125134]
  • Gamola Z Fortenberry, John D Meeker, Brisa N Sánchez, Dana Boyd Barr, Parinya Panuwet, David Bellinger, Lourdes Schnaas, Maritsa Solano-González, Adrienne S Ettinger, Mauricio Hernandez-Avila, Howard Hu, Martha Maria Tellez-Rojo. Urinary 3,5,6-trichloro-2-pyridinol (TCPY) in pregnant women from Mexico City: distribution, temporal variability, and relationship with child attention and hyperactivity. International journal of hygiene and environmental health. 2014 Mar; 217(2-3):405-12. doi: 10.1016/j.ijheh.2013.07.018. [PMID: 24001412]
  • Cruz Garcerá, Enrique Moltó, Patricia Chueca. Factors influencing the efficacy of two organophosphate insecticides in controlling California red scale, Aonidiella aurantii (Maskell). A basis for reducing spray application volume in Mediterranean conditions. Pest management science. 2014 Jan; 70(1):28-38. doi: 10.1002/ps.3515. [PMID: 23404841]
  • Wei Wei, Xiaomin Zong, Xuan Wang, Lihong Yin, Yuepu Pu, Songqin Liu. A disposable amperometric immunosensor for chlorpyrifos-methyl based on immunogen/platinum doped silica sol-gel film modified screen-printed carbon electrode. Food chemistry. 2012 Dec; 135(3):888-92. doi: 10.1016/j.foodchem.2012.06.037. [PMID: 22953801]
  • Stanisław Walorczyk, Dariusz Drożdżyński. Improvement and extension to new analytes of a multi-residue method for the determination of pesticides in cereals and dry animal feed using gas chromatography-tandem quadrupole mass spectrometry revisited. Journal of chromatography. A. 2012 Aug; 1251(?):219-231. doi: 10.1016/j.chroma.2012.06.055. [PMID: 22794797]
  • Gamola Z Fortenberry, Howard Hu, Mary Turyk, Dana Boyd Barr, John D Meeker. Association between urinary 3, 5, 6-trichloro-2-pyridinol, a metabolite of chlorpyrifos and chlorpyrifos-methyl, and serum T4 and TSH in NHANES 1999-2002. The Science of the total environment. 2012 May; 424(?):351-5. doi: 10.1016/j.scitotenv.2012.02.039. [PMID: 22425279]
  • Aly S Derbalah. Efficacy of some botanical extracts against Trogoderma granarium in wheat grains with toxicity evaluation. TheScientificWorldJournal. 2012; 2012(?):639854. doi: 10.1100/2012/639854. [PMID: 22606054]
  • Dana Boyd Barr, Lee-Yang Wong, Roberto Bravo, Gayanga Weerasekera, Martins Odetokun, Paula Restrepo, Do-Gyun Kim, Carolina Fernandez, Ralph D Whitehead, Jose Perez, Maribel Gallegos, Bryan L Williams, Larry L Needham. Urinary concentrations of dialkylphosphate metabolites of organophosphorus pesticides: National Health and Nutrition Examination Survey 1999-2004. International journal of environmental research and public health. 2011 08; 8(8):3063-98. doi: 10.3390/ijerph8083063. [PMID: 21909292]
  • Shoetsu Chiba, Toru Ikawa, Hiroshi Takeshita, Kazue Ichiba, Morihisa Sagi, Toshiji Mukai, Naohiro Anzai. Interactions of human organic anion transporter 1 (hOAT1) with substances associated with forensic toxicology. Legal medicine (Tokyo, Japan). 2011 Jul; 13(4):180-5. doi: 10.1016/j.legalmed.2011.04.001. [PMID: 21561794]
  • Roberta Turci, Elena Sturchio, Jessica Businaro, Laura Casorri, Marcello Imbriani, Claudio Minoia. [The Endocrine Disruptors. Monographies. 6. Chlorpyrifos and chlorpyrifos-methyl]. Giornale italiano di medicina del lavoro ed ergonomia. 2011 Apr; 33(2):149-84. doi: NULL. [PMID: 21796922]
  • Yael Merbl, Itamar Aroch, Sigal Klainbart, Zachi Aizenberg, Efrat Kelmer. Intermediate syndrome of chlorpyriphos toxicity (Polaris) in a caracal (Caracal caracal). Journal of zoo and wildlife medicine : official publication of the American Association of Zoo Veterinarians. 2011 Mar; 42(1):144-8. doi: 10.1638/2010-0075.1. [PMID: 22946387]
  • Craig Sams, Kate Jones. Human volunteer studies investigating the potential for toxicokinetic interactions between the pesticides deltamethrin; pirimicarb and chlorpyrifos-methyl following oral exposure at the acceptable daily intake. Toxicology letters. 2011 Jan; 200(1-2):41-5. doi: 10.1016/j.toxlet.2010.10.012. [PMID: 21035527]
  • Suleiman F Ambali, Chinedu Orieji, Woziri O Abubakar, Muftau Shittu, Mohammed U Kawu. Ameliorative effect of vitamin C on alterations in thyroid hormones concentrations induced by subchronic coadministration of chlorpyrifos and lead in wistar rats. Journal of thyroid research. 2011; 2011(?):214924. doi: 10.4061/2011/214924. [PMID: 21687644]
  • Włodzimierz Matysiak, Barbara Jodłowska-Jedrych. Does administration of non-steroidal anti-inflammatory drug determine morphological changes in adrenal cortex: ultrastructural studies. Protoplasma. 2010 Oct; 246(1-4):109-18. doi: 10.1007/s00709-010-0194-9. [PMID: 20721677]
  • Xiude Hua, Guoliang Qian, Jifei Yang, Baishi Hu, Jiaqin Fan, Na Qin, Gang Li, Yuyan Wang, Fengquan Liu. Development of an immunochromatographic assay for the rapid detection of chlorpyrifos-methyl in water samples. Biosensors & bioelectronics. 2010 Sep; 26(1):189-94. doi: 10.1016/j.bios.2010.06.005. [PMID: 20598518]
  • Rosemary Castorina, Asa Bradman, Laura Fenster, Dana Boyd Barr, Roberto Bravo, Michelle G Vedar, Martha E Harnly, Thomas E McKone, Ellen A Eisen, Brenda Eskenazi. Comparison of current-use pesticide and other toxicant urinary metabolite levels among pregnant women in the CHAMACOS cohort and NHANES. Environmental health perspectives. 2010 Jun; 118(6):856-63. doi: 10.1289/ehp.0901568. [PMID: 20129873]
  • Sara A Quandt, Haiying Chen, Joseph G Grzywacz, Quirina M Vallejos, Leonardo Galvan, Thomas A Arcury. Cholinesterase depression and its association with pesticide exposure across the agricultural season among Latino farmworkers in North Carolina. Environmental health perspectives. 2010 May; 118(5):635-9. doi: 10.1289/ehp.0901492. [PMID: 20085857]
  • 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]
  • Robin M Whyatt, Robin Garfinkel, Lori A Hoepner, Howard Andrews, Darrell Holmes, Megan K Williams, Andria Reyes, Diurka Diaz, Frederica P Perera, David E Camann, Dana B Barr. A biomarker validation study of prenatal chlorpyrifos exposure within an inner-city cohort during pregnancy. Environmental health perspectives. 2009 Apr; 117(4):559-67. doi: 10.1289/ehp.0800041. [PMID: 19440494]
  • Sandra Yucra, Manuel Gasco, Julio Rubio, Gustavo F Gonzales. Semen quality in Peruvian pesticide applicators: association between urinary organophosphate metabolites and semen parameters. Environmental health : a global access science source. 2008 Nov; 7(?):59. doi: 10.1186/1476-069x-7-59. [PMID: 19014632]
  • John D Meeker, Sarena R Ravi, Dana B Barr, Russ Hauser. Circulating estradiol in men is inversely related to urinary metabolites of nonpersistent insecticides. Reproductive toxicology (Elmsford, N.Y.). 2008 Feb; 25(2):184-91. doi: 10.1016/j.reprotox.2007.12.005. [PMID: 18249523]
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  • John D Meeker, Dana B Barr, Russ Hauser. Thyroid hormones in relation to urinary metabolites of non-persistent insecticides in men of reproductive age. Reproductive toxicology (Elmsford, N.Y.). 2006 Oct; 22(3):437-42. doi: 10.1016/j.reprotox.2006.02.005. [PMID: 16584866]
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  • John D Meeker, Louise Ryan, Dana B Barr, Robert F Herrick, Deborah H Bennett, Roberto Bravo, Russ Hauser. The relationship of urinary metabolites of carbaryl/naphthalene and chlorpyrifos with human semen quality. Environmental health perspectives. 2004 Dec; 112(17):1665-70. doi: 10.1289/ehp.7234. [PMID: 15579410]
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  • Michele Del Carlo, Marcello Mascini, Alessia Pepe, Dario Compagnone, Marco Mascini. Electrochemical bioassay for the investigation of chlorpyrifos-methyl in vine samples. Journal of agricultural and food chemistry. 2002 Dec; 50(25):7206-10. doi: 10.1021/jf0257852. [PMID: 12452633]
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  • H M Koch, J Hardt, J Angerer. Biological monitoring of exposure of the general population to the organophosphorus pesticides chlorpyrifos and chlorpyrifos-methyl by determination of their specific metabolite 3,5,6-trichloro-2-pyridinol. International journal of hygiene and environmental health. 2001 Nov; 204(2-3):175-80. doi: 10.1078/1438-4639-00082. [PMID: 11759161]
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