Malaoxon (BioDeep_00000002240)

 

Secondary id: BioDeep_00001867741

human metabolite Endogenous blood metabolite


代谢物信息卡片


1,4-diethyl 2-[(dimethoxyphosphoryl)sulfanyl]butanedioate

化学式: C10H19O7PS (314.0589074)
中文名称: 马拉氧磷
谱图信息: 最多检出来源 Homo sapiens(blood) 7.69%

分子结构信息

SMILES: CCOC(=O)CC(C(=O)OCC)SP(=O)(OC)OC
InChI: InChI=1S/C10H19O7PS/c1-5-16-9(11)7-8(10(12)17-6-2)19-18(13,14-3)15-4/h8H,5-7H2,1-4H3

描述信息

Malaoxon is a metabolite of malathion. Malaoxon is a chemical compound with the formula C10H19O7PS. More specifically, it is a phosphorothioate. It is a breakdown product of, and more toxic than, malathion. (Wikipedia)
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3713
D010575 - Pesticides > D007306 - Insecticides
D016573 - Agrochemicals

同义名列表

2 个代谢物同义名

1,4-diethyl 2-[(dimethoxyphosphoryl)sulfanyl]butanedioate; MALAOXON



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

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

  • Zhou Tong, Yan Shen, DanDan Meng, XiaoTong Yi, MingNa Sun, Xu Dong, Yue Chu, JinSheng Duan. Ecological threat caused by malathion and its chiral metabolite in a honey bee-rape system: Stereoselective exposure risk and the mechanism revealed by proteome. The Science of the total environment. 2023 Mar; 874(?):162585. doi: 10.1016/j.scitotenv.2023.162585. [PMID: 36870510]
  • Li-Wei Meng, Meng-Lan Peng, Meng-Ling Chen, Guo-Rui Yuan, Li-Sha Zheng, Wen-Jie Bai, Guy Smagghe, Jin-Jun Wang. A glutathione S-transferase (BdGSTd9) participates in malathion resistance via directly depleting malathion and its toxic oxide malaoxon in Bactrocera dorsalis (Hendel). Pest management science. 2020 Aug; 76(8):2557-2568. doi: 10.1002/ps.5810. [PMID: 32128980]
  • Haina Sun, Nicolas Buchon, Jeffrey G Scott. Mdr65 decreases toxicity of multiple insecticides in Drosophila melanogaster. Insect biochemistry and molecular biology. 2017 10; 89(?):11-16. doi: 10.1016/j.ibmb.2017.08.002. [PMID: 28803989]
  • Zhiqiang Kong, Minmin Li, Jieying Chen, Yuejing Gui, Yuming Bao, Bei Fan, Qiu Jian, Frédéric Francis, Xiaofeng Dai. Behavior of field-applied triadimefon, malathion, dichlorvos, and their main metabolites during barley storage and beer processing. Food chemistry. 2016 Nov; 211(?):679-86. doi: 10.1016/j.foodchem.2016.05.058. [PMID: 27283683]
  • Rezeda V Shamagsumova, Dmitry N Shurpik, Pavel L Padnya, Ivan I Stoikov, Gennady A Evtugyn. Acetylcholinesterase biosensor for inhibitor measurements based on glassy carbon electrode modified with carbon black and pillar[5]arene. Talanta. 2015 Nov; 144(?):559-68. doi: 10.1016/j.talanta.2015.07.008. [PMID: 26452862]
  • J Von Der Wellen, F Worek, H Thiermann, T Wille. Investigations of kinetic interactions between lipid emulsions, hydroxyethyl starch or dextran and organophosphorus compounds. Clinical toxicology (Philadelphia, Pa.). 2013 Dec; 51(10):918-22. doi: 10.3109/15563650.2013.857025. [PMID: 24199642]
  • Li Chen, Taifeng Zhao, Canping Pan, John H Ross, Robert I Krieger. Preformed biomarkers including dialkylphosphates (DAPs) in produce may confound biomonitoring in pesticide exposure and risk assessment. Journal of agricultural and food chemistry. 2012 Sep; 60(36):9342-51. doi: 10.1021/jf303116p. [PMID: 22906185]
  • Olajire A Gbaye, Graham J Holloway, Amanda Callaghan. Variation in the sensitivity of Callosobruchus (Coleoptera: Bruchidae) acetylcholinesterase to the organophosphate insecticide malaoxon: effect of species, geographical strain and food type. Pest management science. 2012 Sep; 68(9):1265-71. doi: 10.1002/ps.3293. [PMID: 22605686]
  • Agustín Basso, Andrés M Attademo, Rafael C Lajmanovich, Paola M Peltzer, Celina Junges, Mariana C Cabagna, Gabriela S Fiorenza, Juan Carlos Sanchez-Hernandez. Plasma esterases in the tegu lizard Tupinambis merianae (Reptilia, Teiidae): impact of developmental stage, sex, and organophosphorus in vitro exposure. Environmental science and pollution research international. 2012 Jan; 19(1):214-25. doi: 10.1007/s11356-011-0549-6. [PMID: 21717171]
  • Najwa Ben Oujji, Idriss Bakas, Georges Istamboulié, Ihya Ait-Ichou, Elhabib Ait-Addi, Régis Rouillon, Thierry Noguer. Acetylcholinesterase immobilized on magnetic beads for pesticides detection: application to olive oil analysis. Sensors (Basel, Switzerland). 2012; 12(6):7893-904. doi: 10.3390/s120607893. [PMID: 22969377]
  • Mabruka H Tarhoni, Vasanthy Vigneswara, Marie Smith, Susan Anderson, Peter Wigmore, John E Lees, David E Ray, Wayne G Carter. Detection, quantification, and microlocalisation of targets of pesticides using microchannel plate autoradiographic imagers. Molecules (Basel, Switzerland). 2011 Oct; 16(10):8535-51. doi: 10.3390/molecules16108535. [PMID: 21989313]
  • Yiou Pan, Qingli Shang, Kui Fang, Jing Zhang, Jinghui Xi. Down-regulated transcriptional level of Ace1 combined with mutations in Ace1 and Ace2 of Aphis gossypii are related with omethoate resistance. Chemico-biological interactions. 2010 Dec; 188(3):553-7. doi: 10.1016/j.cbi.2010.07.022. [PMID: 20692243]
  • Milica Zlatković, Miodrag Jovanović, Dragana Djordjević, Slavica Vucinić. [Rapid simultaneous determination of organophosphorus pesticides in human serum and urine by liquid chromatography-mass spectrometry]. Vojnosanitetski pregled. 2010 Sep; 67(9):717-22. doi: 10.2298/vsp1009717z. [PMID: 20954410]
  • Mustafa Alp Cetinkaya, Emine Baydan. Investigation of in vitro effects of ethephon and chlorpyrifos, either alone or in combination, on rat intestinal muscle contraction. Interdisciplinary toxicology. 2010 Mar; 3(1):35-9. doi: 10.2478/v10102-010-0002-6. [PMID: 21217869]
  • Picheng Zhao, Kun Yan Zhu, Haobo Jiang. Heterologous expression, purification, and biochemical characterization of a greenbug (Schizaphis graminum) acetylcholinesterase encoded by a paralogous gene (ace-1). Journal of biochemical and molecular toxicology. 2010 Jan; 24(1):51-9. doi: 10.1002/jbt.20311. [PMID: 20146377]
  • Atef M Al-Attar. Physiological and histopathological investigations on the effects of alpha-lipoic acid in rats exposed to malathion. Journal of biomedicine & biotechnology. 2010; 2010(?):203503. doi: 10.1155/2010/203503. [PMID: 20454535]
  • Haobo Jiang, Siwei Liu, Picheng Zhao, Carey Pope. Recombinant expression and biochemical characterization of the catalytic domain of acetylcholinesterase-1 from the African malaria mosquito, Anopheles gambiae. Insect biochemistry and molecular biology. 2009 Sep; 39(9):646-53. doi: 10.1016/j.ibmb.2009.07.002. [PMID: 19607916]
  • Brian C Geyer, Ryan R Woods, Tsafrir S Mor. Increased organophosphate scavenging in a butyrylcholinesterase mutant. Chemico-biological interactions. 2008 Sep; 175(1-3):376-9. doi: 10.1016/j.cbi.2008.04.012. [PMID: 18514178]
  • Mabruka H Tarhoni, Timothy Lister, David E Ray, Wayne G Carter. Albumin binding as a potential biomarker of exposure to moderately low levels of organophosphorus pesticides. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2008 Jun; 13(4):343-63. doi: 10.1080/13547500801973563. [PMID: 18484351]
  • Ingrid Walz, Wolfgang Schwack. Cutinase inhibition by means of insecticidal organophosphates and carbamates. 3. Oxidation of phosphorothionates by chloroperoxidase from Caldariomyces fumago. Journal of agricultural and food chemistry. 2007 Oct; 55(20):8177-86. doi: 10.1021/jf071598y. [PMID: 17824663]
  • Grant T McQuate, Roger I Vargas. Assessment of attractiveness of plants as roosting sites for the melon fly, Bactrocera cucurbitae, and oriental fruit fly, Bactrocera dorsalis. Journal of insect science (Online). 2007; 7(?):57. doi: 10.1673/031.007.5701. [PMID: 20334596]
  • Asa Bradman, Robin M Whyatt. Characterizing exposures to nonpersistent pesticides during pregnancy and early childhood in the National Children's Study: a review of monitoring and measurement methodologies. Environmental health perspectives. 2005 Aug; 113(8):1092-9. doi: 10.1289/ehp.7769. [PMID: 16079084]
  • Eric S Peeples, Lawrence M Schopfer, Ellen G Duysen, Reggie Spaulding, Troy Voelker, Charles M Thompson, Oksana Lockridge. Albumin, a new biomarker of organophosphorus toxicant exposure, identified by mass spectrometry. Toxicological sciences : an official journal of the Society of Toxicology. 2005 Feb; 83(2):303-12. doi: 10.1093/toxsci/kfi023. [PMID: 15525694]
  • S Padilla, H-J Sung, V C Moser. Further assessment of an in vitro screen that may help identify organophosphorus pesticides that are more acutely toxic to the young. Journal of toxicology and environmental health. Part A. 2004 Sep; 67(18):1477-89. doi: 10.1080/15287390490483836. [PMID: 15371233]
  • Andras Bozsik, Frédéric Francis, Charles Gaspar, Eric Haubruge. Effect of some insecticides on acetylcholinesterase from beneficial insects: Coccinella septempunctata, Chrysoperla carnea and Forficula auricularia. Mededelingen (Rijksuniversiteit te Gent. Fakulteit van de Landbouwkundige en Toegepaste Biologische Wetenschappen). 2002; 67(3):671-7. doi: . [PMID: 12696436]
  • A W Abu-Qare, M B Abou-Donia. Simultaneous determination of malathion, permethrin, DEET (N,N-diethyl-m-toluamide), and their metabolites in rat plasma and urine using high performance liquid chromatography. Journal of pharmaceutical and biomedical analysis. 2001 Sep; 26(2):291-9. doi: 10.1016/s0731-7085(01)00407-1. [PMID: 11470206]
  • C Sams, H J Mason. Detoxification of organophosphates by A-esterases in human serum. Human & experimental toxicology. 1999 Nov; 18(11):653-8. doi: 10.1191/096032799678839581. [PMID: 10602389]
  • M R Hirvonen, L Paljärvi, K M Savolainen. Malaoxon-induced neurotoxicity in old rats: alterations in cerebral inositol lipid signalling, brain tissue calcium levels and early neuronal injury. Toxicology. 1993 Apr; 79(2):157-67. doi: 10.1016/0300-483x(93)90129-g. [PMID: 8497869]
  • C Morgade, A Barquet. Body distribution of malathion and its metabolites in a fatal poisoning by ingestion. Journal of toxicology and environmental health. 1982 Aug; 10(2):321-5. doi: 10.1080/15287398209530254. [PMID: 7143485]