Diethylthiophosphate (BioDeep_00000002937)

 

Secondary id: BioDeep_00001868516

human metabolite Endogenous blood metabolite


代谢物信息卡片


O,O-Diethyl phosphorothionate, potassium salt

化学式: C4H11O3PS (170.0166506)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 1.21%

分子结构信息

SMILES: CCOP(=S)(O)OCC
InChI: InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9)

描述信息

Diethylthiophosphate, also known as DETP, belongs to the class of organic compounds known as thiophosphate diesters. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR)(OR)=S, where exactly two R-groups are organyl groups. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Diethylthiophosphate is a potentially toxic compound. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase Chronic exposure to POs has neurological sequelae as well and data suggests that OP exposure alters sperm chromatin condensation (A3181, A3182, A3183, A3181). Chronic exposure to POs has neurological sequelae as well (PMID 8179040) and data suggests that OP exposure alters sperm chromatin condensation (PMID 15050412). PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase (PMID 11991535).
Diethylthiophosphate is the most frequent metabolite of organophosphorus (OP) found in urine (PMID 15050412). Organophosphorus compounds are widely used as pesticides because of easy degradation in the environment. Acute OP intoxication results from blockage of the decomposition of synaptic acetylcholine because the pesticide covalently binds to chlolinesterase (PMID 11991535). Chronic exposure to POs has neurological sequelae as well (PMID 8179040) and data suggests that OP exposure alters sperm chromatin condensation (PMID 15050412) [HMDB]
KEIO_ID D113

同义名列表

16 个代谢物同义名

O,O-Diethyl phosphorothionate, potassium salt; O,O-Diethyl phosphorothionate, ammonium salt; diethoxy-hydroxy-sulfanylidene-phosphorane; O,O-Diethyl phosphorothionate, sodium salt; O,O-Diethyl hydrogen thiophosphoric acid; diethoxy(sulfanylidene)phosphinous acid; O,O-Diethyl hydrogen thiophosphate; O,O-Diethyl phosphorothionate; O,O-Diethyl phosphorothioate; O, O-Diethyl thiophosphate; Diethylthiophosphoric acid; O,O-Diethyl thiophosphate; Diethylthiophosphic acid; Diethylthiophosphorate; Diethylthiophosphate; DETP



数据库引用编号

22 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

5 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

  • Yiwen Wang, Limei Chen, Caifeng Wang, Yi Hum, Yu Gao, Yijun Zhou, Rong Shi, Yan Zhang, Michihiro Kamijima, Jun Ueyama, Ying Tian. Association Between Organophosphate Pesticide Exposure and Thyroid Hormones in Pregnant Women. Epidemiology (Cambridge, Mass.). 2017 10; 28 Suppl 1(?):S35-S40. doi: 10.1097/ede.0000000000000721. [PMID: 29028673]
  • Razia Alam Gilani, Mazhar Rafique, Abdul Rehman, Muhammad Farooq Hussain Munis, Shafiq Ur Rehman, Hassan Javed Chaudhary. Biodegradation of chlorpyrifos by bacterial genus Pseudomonas. Journal of basic microbiology. 2016 Feb; 56(2):105-19. doi: 10.1002/jobm.201500336. [PMID: 26837064]
  • H Abdel-Gawad, R M Abdel-Hameed, A Witczak. Residues of ¹⁴C-ethion along the extraction and refining process of maize oil, and the bioavailability of bound residues in the cake for experimental animals. Bulletin of environmental contamination and toxicology. 2013 Aug; 91(2):240-5. doi: 10.1007/s00128-013-1027-2. [PMID: 23765209]
  • Mahmoud M A Desouky, Hassan Abdel-Gawad, Bahira Hegazi. Distribution, fate and histopathological effects of ethion insecticide on selected organs of the crayfish, Procambarus clarkii. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Feb; 52(?):42-52. doi: 10.1016/j.fct.2012.10.029. [PMID: 23127602]
  • Qianfei Zhao, Ruliang Xie, Tao Zhang, Jing Fang, Xiangdong Mei, Jun Ning, Yun Tang. Homo- and hetero-dimers of inactive organophosphorous group binding at dual sites of AChE. Bioorganic & medicinal chemistry letters. 2011 Nov; 21(21):6404-8. doi: 10.1016/j.bmcl.2011.08.098. [PMID: 21940169]
  • Yan Zhang, Sha Zhu, Yu Gao, Xiao-jin Wang, Tao Chen, You Yang, Guo-quan Wang, Guo-hua Hu, Rong Shi, Ping Jin, Ying Tian. [A case-control study on correlation of pesticide exposure with childhood acute leukemia]. Zhonghua yu fang yi xue za zhi [Chinese journal of preventive medicine]. 2011 Jan; 45(1):41-6. doi: . [PMID: 21418818]
  • Andrea L Busby-Hjerpe, James A Campbell, Jordan Ned Smith, Sookwang Lee, Torka S Poet, Dana B Barr, Charles Timchalk. Comparative pharmacokinetics of chlorpyrifos versus its major metabolites following oral administration in the rat. Toxicology. 2010 Jan; 268(1-2):55-63. doi: 10.1016/j.tox.2009.11.022. [PMID: 19963030]
  • G K Hemakanthi De Alwis, Larry L Needham, Dana B Barr. Automated solid phase extraction, on-support derivatization and isotope dilution-GC/MS method for the detection of urinary dialkyl phosphates in humans. Talanta. 2009 Jan; 77(3):1063-7. doi: 10.1016/j.talanta.2008.08.007. [PMID: 19064092]
  • Gayanga Weerasekera, Kimberly D Smith, Larry L Needham, Dana B Barr. A rapid, cost-effective method for analyzing organophosphorus pesticide metabolites in human urine for counter-terrorism response. Journal of analytical toxicology. 2008 Jan; 32(1):106-15. doi: 10.1093/jat/32.1.106. [PMID: 18269802]
  • Charles Timchalk, Andrea Busby, James A Campbell, Larry L Needham, Dana B Barr. Comparative pharmacokinetics of the organophosphorus insecticide chlorpyrifos and its major metabolites diethylphosphate, diethylthiophosphate and 3,5,6-trichloro-2-pyridinol in the rat. Toxicology. 2007 Jul; 237(1-3):145-157. doi: 10.1016/j.tox.2007.05.007. [PMID: 17590257]
  • Brenda Eskenazi, Amy R Marks, Asa Bradman, Kim Harley, Dana B Barr, Caroline Johnson, Norma Morga, Nicholas P Jewell. Organophosphate pesticide exposure and neurodevelopment in young Mexican-American children. Environmental health perspectives. 2007 May; 115(5):792-8. doi: 10.1289/ehp.9828. [PMID: 17520070]
  • Wolfgang Bicker, Michael Lämmerhofer, Dieter Genser, Heinrich Kiss, Wolfgang Lindner. A case study of acute human chlorpyrifos poisoning: novel aspects on metabolism and toxicokinetics derived from liquid chromatography-tandem mass spectrometry analysis of urine samples. Toxicology letters. 2005 Dec; 159(3):235-51. doi: 10.1016/j.toxlet.2005.05.013. [PMID: 15996837]
  • Asa Bradman, Brenda Eskenazi, Dana B Barr, Roberto Bravo, Rosemary Castorina, Jonathan Chevrier, Katherine Kogut, Martha E Harnly, Thomas E McKone. Organophosphate urinary metabolite levels during pregnancy and after delivery in women living in an agricultural community. Environmental health perspectives. 2005 Dec; 113(12):1802-7. doi: 10.1289/ehp.7894. [PMID: 16330368]
  • Wolfgang Bicker, Michael Lämmerhofer, Wolfgang Lindner. Determination of chlorpyrifos metabolites in human urine by reversed-phase/weak anion exchange liquid chromatography-electrospray ionisation-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Aug; 822(1-2):160-9. doi: 10.1016/j.jchromb.2005.06.003. [PMID: 15994139]
  • N Kupfermann, A Schmoldt, H Steinhart. Rapid and sensitive quantitative analysis of alkyl phosphates in urine after organophosphate poisoning. Journal of analytical toxicology. 2004 May; 28(4):242-8. doi: 10.1093/jat/28.4.242. [PMID: 15189674]
  • L C Sánchez-Peña, B E Reyes, L López-Carrillo, R Recio, J Morán-Martínez, M E Cebrián, B Quintanilla-Vega. Organophosphorous pesticide exposure alters sperm chromatin structure in Mexican agricultural workers. Toxicology and applied pharmacology. 2004 Apr; 196(1):108-13. doi: 10.1016/j.taap.2003.11.023. [PMID: 15050412]
  • S J Garfitt, K Jones, H J Mason, J Cocker. Exposure to the organophosphate diazinon: data from a human volunteer study with oral and dermal doses. Toxicology letters. 2002 Aug; 134(1-3):105-13. doi: 10.1016/s0378-4274(02)00178-9. [PMID: 12191867]
  • W C Lin, C H Kuei, H C Wu, C C Yang, H Y Chang. Method for the determination of dialkyl phosphates in urine by strong anion exchange disk extraction and in-vial derivatization. Journal of analytical toxicology. 2002 Apr; 26(3):176-80. doi: 10.1093/jat/26.3.176. [PMID: 11991535]
  • A N Oglobline, H Elimelakh, B Tattam, R Geyer, G E O'Donnell, G Holder. Negative ion chemical ionization GC/MS-MS analysis of dialkylphosphate metabolites of organophosphate pesticides in urine of non-occupationally exposed subjects. The Analyst. 2001 Jul; 126(7):1037-41. doi: 10.1039/b102004h. [PMID: 11478632]
  • D Schenke. Analytical method for the determination of O,O-diethyl phosphate and O,O-diethyl thiophosphate in faecal samples. Chemosphere. 2000 Nov; 41(9):1313-20. doi: 10.1016/s0045-6535(00)00020-5. [PMID: 11057566]
  • V Drevenkar, Z Vasilić, B Stengl, Z Fröbe, V Rumenjak. Chlorpyrifos metabolites in serum and urine of poisoned persons. Chemico-biological interactions. 1993 Jun; 87(1-3):315-22. doi: 10.1016/0009-2797(93)90059-8. [PMID: 7688273]
  • Z Vasilić, V Drevenkar, B Stengl, Z Fröbe, V Rumenjak. Diethylphosphorus metabolites in serum and urine of persons poisoned by phosalone. Chemico-biological interactions. 1993 Jun; 87(1-3):305-13. doi: 10.1016/0009-2797(93)90058-7. [PMID: 8343988]
  • C P Weisskopf, J N Seiber, N Maizlish, M Schenker. Personnel exposure to diazinon in a supervised pest eradication program. Archives of environmental contamination and toxicology. 1988 Mar; 17(2):201-12. doi: 10.1007/bf01056026. [PMID: 3355234]
  • N Maizlish, M Schenker, C Weisskopf, J Seiber, S Samuels. A behavioral evaluation of pest control workers with short-term, low-level exposure to the organophosphate diazinon. American journal of industrial medicine. 1987; 12(2):153-72. doi: 10.1002/ajim.4700120205. [PMID: 3661569]
  • M E Mount. Diagnostic value of urinary dialkyl phosphate measurement in goats exposed to diazinon. American journal of veterinary research. 1984 Apr; 45(4):817-24. doi: . [PMID: 6731999]