Dimethylarsinic acid (BioDeep_00000002848)

 

Secondary id: BioDeep_00001867631, BioDeep_00001892245

human metabolite Endogenous blood metabolite


代谢物信息卡片


Hydroxydimethylarsine oxide

化学式: C2H7AsO2 (137.9661982)
中文名称: 二甲基砷标准溶液
谱图信息: 最多检出来源 Homo sapiens(blood) 0.26%

分子结构信息

SMILES: C[As](=O)(C)O
InChI: InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)

描述信息

Dimethylarsinic acid, also known as cacodylic acid, is formally rated as possibly a carcinogenic (IARC 2B), potentially toxic compound. Derivatives of cacodylic acid, cacodylates, were frequently used as herbicides. For example, Agent Blue, one of the chemicals used during the Vietnam War, is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a buffering agent in the preparation and fixation of biological samples for transmission electron microscopy. Dimethylarsinic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be teratogenic in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing apoptosis and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, dimethylarsinic acid does promote tumours in the presence of carcinogens in organs such as the kidneys and liver (Wikipedia).
Cacodylic acid is the chemical compound with the formula (CH3)2AsO2H. Derivatives of cacodylic acid, cacodylates, were frequently used as herbicides. For example, "Agent Blue," one of the chemicals used during the Vietnam War, is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a buffering agent in the preparation and fixation of biological samples for transmission electron microscopy.
D010575 - Pesticides > D006540 - Herbicides
D016573 - Agrochemicals

同义名列表

13 个代谢物同义名

Hydroxydimethylarsine oxide; As,as-dimethylarsinic acid; Acid, dimethylarsinic; Dimethylarsenic acid; Dimethylarsinic acid; Dimethylarsinate; Acid, cacodylic; [As(CH3)2O(OH)]; cacodylic acid; Kakodylsaeure; Me2as(=o)OH; CACODYLate; Ansar



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

60 个相关的代谢反应过程信息。

Reactome(60)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

4 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

  • Yi-Jie Wang, Chun-Yan Dong, Zhong Tang, Fang-Jie Zhao. Translocation, enzymatic reduction and toxicity of dimethylarsenate in rice. Plant physiology and biochemistry : PPB. 2024 Feb; 207(?):108393. doi: 10.1016/j.plaphy.2024.108393. [PMID: 38290344]
  • Andrea E Colina Blanco, Erik Pischke, Alejandra Higa Mori, Carolin F Kerl, Stephan Clemens, Britta Planer-Friedrich. In Planta Arsenic Thiolation in Rice and Arabidopsis thaliana. Environmental science & technology. 2023 Dec; 57(51):21846-21854. doi: 10.1021/acs.est.3c06603. [PMID: 38093687]
  • Yang Song, Yang Liu, Haipu Li, Ying Fang, Denglong Lu, Zhaoguang Yang. The crucial elements for lettuce (Lactuca sativa L.) growth under DMA stress and the linkage with DMA behavior: A new application of ionome. Journal of environmental management. 2023 Sep; 347(?):119124. doi: 10.1016/j.jenvman.2023.119124. [PMID: 37776798]
  • Chuan Chen, Yu Yu, Yijie Wang, Axiang Gao, Baoyun Yang, Zhu Tang, Fang-Jie Zhao. Reduction of Dimethylarsenate to Highly Toxic Dimethylarsenite in Paddy Soil and Rice Plants. Environmental science & technology. 2023 01; 57(1):822-830. doi: 10.1021/acs.est.2c07418. [PMID: 36490306]
  • Britta Planer-Friedrich, Carolin F Kerl, Andrea E Colina Blanco, Stephan Clemens. Dimethylated Thioarsenates: A Potentially Dangerous Blind Spot in Current Worldwide Regulatory Limits for Arsenic in Rice. Journal of agricultural and food chemistry. 2022 Aug; 70(31):9610-9618. doi: 10.1021/acs.jafc.2c02425. [PMID: 35901520]
  • Jun Tang, Qinheng Zhu, Yang Xu, Yexinyi Zhou, Longtao Zhu, Lanfei Jin, Weiye Wang, Lan Gao, Guangdi Chen, Hao Zhao. Total arsenic, dimethylarsinic acid, lead, cadmium, total mercury, methylmercury and hypertension among Asian populations in the United States: NHANES 2011-2018. Ecotoxicology and environmental safety. 2022 Aug; 241(?):113776. doi: 10.1016/j.ecoenv.2022.113776. [PMID: 35738098]
  • Erik Pischke, Fabrizio Barozzi, Andrea E Colina Blanco, Carolin F Kerl, Britta Planer-Friedrich, Stephan Clemens. Dimethylmonothioarsenate Is Highly Toxic for Plants and Readily Translocated to Shoots. Environmental science & technology. 2022 07; 56(14):10072-10083. doi: 10.1021/acs.est.2c01206. [PMID: 35759640]
  • Larissa Müller, Gabriela Corrêa Soares, Marcelo Estrella Josende, José Maria Monserrat, Juliane Ventura-Lima. Comparison of the toxic effects of organic and inorganic arsenic in Caenorhabditis elegans using a multigenerational approach. Toxicology research. 2022 Jun; 11(3):402-416. doi: 10.1093/toxres/tfac010. [PMID: 35782638]
  • Humairat H Rahman, Danielle Niemann, Stuart H Munson-McGee. Association of albumin to creatinine ratio with urinary arsenic and metal exposure: evidence from NHANES 2015-2016. International urology and nephrology. 2022 Jun; 54(6):1343-1353. doi: 10.1007/s11255-021-03018-y. [PMID: 34643861]
  • Raquel Soler-Blasco, Mario Murcia, Manuel Lozano, Blanca Sarzo, Ana Esplugues, Gabriel Riutort-Mayol, Jesús Vioque, Nerea Lertxundi, Loreto Santa Marina, Aitana Lertxundi, Amaia Irizar, Simone Braeuer, Ferran Ballester, Sabrina Llop. Prenatal arsenic exposure, arsenic methylation efficiency, and neuropsychological development among preschool children in a Spanish birth cohort. Environmental research. 2022 05; 207(?):112208. doi: 10.1016/j.envres.2021.112208. [PMID: 34662579]
  • Xin Liu, Jiating Wang, Hongyu Deng, Xiaoting Zhong, Chengji Li, Yu Luo, Linkang Chen, Bin Zhang, Dongbin Wang, Yixiang Huang, Jingjing Zhang, Lianxian Guo. In situ analysis of variations of arsenicals, microbiome and transcriptome profiles along murine intestinal tract. Journal of hazardous materials. 2022 04; 427(?):127899. doi: 10.1016/j.jhazmat.2021.127899. [PMID: 34876320]
  • Seul-Gi Lee, Ingu Kang, Mi-Na Seo, Jung-Eum Lee, Sang-Yong Eom, Myung-Sil Hwang, Kyung Su Park, Byung-Sun Choi, Ho-Jang Kwon, Young-Seoub Hong, Heon Kim, Jung-Duck Park. Exposure Levels and Contributing Factors of Various Arsenic Species and Their Health Effects on Korean Adults. Archives of environmental contamination and toxicology. 2022 Apr; 82(3):391-402. doi: 10.1007/s00244-022-00913-y. [PMID: 35132447]
  • Jun Dai, Zhu Tang, A-Xiang Gao, Britta Planer-Friedrich, Peter M Kopittke, Fang-Jie Zhao, Peng Wang. Widespread Occurrence of the Highly Toxic Dimethylated Monothioarsenate (DMMTA) in Rice Globally. Environmental science & technology. 2022 03; 56(6):3575-3586. doi: 10.1021/acs.est.1c08394. [PMID: 35174706]
  • Krzysztof Żamojć, Dariusz Wyrzykowski, Lech Chmurzyński. On the Effect of pH, Temperature, and Surfactant Structure on Bovine Serum Albumin-Cationic/Anionic/Nonionic Surfactants Interactions in Cacodylate Buffer-Fluorescence Quenching Studies Supported by UV Spectrophotometry and CD Spectroscopy. International journal of molecular sciences. 2021 Dec; 23(1):. doi: 10.3390/ijms23010041. [PMID: 35008466]
  • YongChen Wu, Huang Zhang, KaiTeng Wang, Wei Chen, ZhiFeng Liu, Lian Chen, XuSheng Wang, FengFu Fu, GuiDi Yang. Metabolic and residual characteristic of different arsenic species contained in laver during mouse digestion. The Science of the total environment. 2021 Nov; 793(?):148434. doi: 10.1016/j.scitotenv.2021.148434. [PMID: 34171799]
  • Jin Xie, Xiao-Dong Niu, Jiao-Jiao Xie, Kai-Qiang He, Meng-Dan Shi, Su-Juan Yu, Chun-Gang Yuan, Jing-Fu Liu. Distribution and chemical speciation of arsenic in different sized atmospheric particulate matters. Journal of environmental sciences (China). 2021 Oct; 108(?):1-7. doi: 10.1016/j.jes.2021.02.010. [PMID: 34465424]
  • Haijuan Wang, Suping Cui, Li Ma, Zhongzhen Wang, Hongbin Wang. Variations of arsenic forms and the role of arsenate reductase in three hydrophytes exposed to different arsenic species. Ecotoxicology and environmental safety. 2021 Sep; 221(?):112415. doi: 10.1016/j.ecoenv.2021.112415. [PMID: 34171691]
  • Semih Kara, Dotse Selali Chormey, Ahmet Saygılar, Sezgin Bakırdere. Arsenic speciation in rice samples for trace level determination by high performance liquid chromatography-inductively coupled plasma-mass spectrometry. Food chemistry. 2021 Sep; 356(?):129706. doi: 10.1016/j.foodchem.2021.129706. [PMID: 33831825]
  • Sixun Guo, Xinyu Wang, Chunlu Gao, Zhiqiang Wu, Hongzhu Chen, Liwang Lin, Meihua Guo, Yanhui Gao, Xin Hai. Monomethylated arsenic was the Major methylated arsenic in Red blood cells of acute promyelocytic leukemia patients treated with arsenic trioxide. Toxicology letters. 2021 Sep; 347(?):78-85. doi: 10.1016/j.toxlet.2021.04.005. [PMID: 33865921]
  • Christoph-Cornelius Brombach, Shaun T Lancaster, Matthew A Dexter, K Clive Thompson, Warren T Corns. Stability, preservation and storage of As(iii), DMA, MMA and As(v) in water samples. Analytical methods : advancing methods and applications. 2021 07; 13(28):3154-3159. doi: 10.1039/d1ay00743b. [PMID: 34164635]
  • Molly Scannell Bryan, Tamar Sofer, Majid Afshar, Yasmin Mossavar-Rahmani, H Dean Hosgood, Naresh M Punjabi, Donglin Zeng, Martha L Daviglus, Maria Argos. Mendelian randomization analysis of arsenic metabolism and pulmonary function within the Hispanic Community Health Study/Study of Latinos. Scientific reports. 2021 06; 11(1):13470. doi: 10.1038/s41598-021-92911-8. [PMID: 34188144]
  • Zixiang Gao, Xianjin Tang, Mujun Ye, Iram Gul, Hao Chen, Guochao Yan, Scott X Chang, Yongchao Liang. Effects of silicon on the uptake and accumulation of arsenite and dimethylarsinic acid in rice (Oryza sativa L.). Journal of hazardous materials. 2021 05; 409(?):124442. doi: 10.1016/j.jhazmat.2020.124442. [PMID: 33168309]
  • Luis Fernando Negro Silva, Kiran Makhani, Maryse Lemaire, Catherine A Lemarié, Dany Plourde, Alicia M Bolt, Christopher Chiavatti, D Scott Bohle, Stéphanie Lehoux, Mark S Goldberg, Koren K Mann. Sex-Specific Effects of Prenatal and Early Life Inorganic and Methylated Arsenic Exposure on Atherosclerotic Plaque Development and Composition in Adult ApoE-/- Mice. Environmental health perspectives. 2021 05; 129(5):57008. doi: 10.1289/ehp8171. [PMID: 34014776]
  • Franklin Linam, Kendall McCoach, Matt A Limmer, Angelia L Seyfferth. Contrasting effects of rice husk pyrolysis temperature on silicon dissolution and retention of cadmium (Cd) and dimethylarsinic acid (DMA). The Science of the total environment. 2021 Apr; 765(?):144428. doi: 10.1016/j.scitotenv.2020.144428. [PMID: 33412375]
  • Fen Wu, Yu Chen, Ana Navas-Acien, Michela L Garabedian, Jane Coates, Jonathan D Newman. Arsenic Exposure, Arsenic Metabolism, and Glycemia: Results from a Clinical Population in New York City. International journal of environmental research and public health. 2021 04; 18(7):. doi: 10.3390/ijerph18073749. [PMID: 33916749]
  • Jun Yoshinaga, Tomohiro Narukawa. Dietary intake and urinary excretion of methylated arsenicals of Japanese adults consuming marine foods and rice. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2021 Apr; 38(4):622-629. doi: 10.1080/19440049.2021.1877836. [PMID: 33625959]
  • Dayana A Delgado, Meytal Chernoff, Lei Huang, Lin Tong, Lin Chen, Farzana Jasmine, Justin Shinkle, Shelley A Cole, Karin Haack, Jack Kent, Jason Umans, Lyle G Best, Heather Nelson, Donald Vander Griend, Joseph Graziano, Muhammad G Kibriya, Ana Navas-Acien, Margaret R Karagas, Habibul Ahsan, Brandon L Pierce. Rare, Protein-Altering Variants in AS3MT and Arsenic Metabolism Efficiency: A Multi-Population Association Study. Environmental health perspectives. 2021 04; 129(4):47007. doi: 10.1289/ehp8152. [PMID: 33826413]
  • Andrea E Colina Blanco, Carolin F Kerl, Britta Planer-Friedrich. Detection of Thioarsenates in Rice Grains and Rice Products. Journal of agricultural and food chemistry. 2021 Feb; 69(7):2287-2294. doi: 10.1021/acs.jafc.0c06853. [PMID: 33566616]
  • Ram B Jain. Concentrations of selected arsenic species in urine across various stages of renal function including hyperfiltration. Environmental science and pollution research international. 2021 Feb; 28(7):8594-8605. doi: 10.1007/s11356-020-11189-x. [PMID: 33067786]
  • Yuko Takayama, Yuko Masuzaki, Futoshi Mizutani, Toyoto Iwata, Eri Maeda, Mikako Tsukada, Kyoko Nomura, Yasunori Ito, Yoichi Chisaki, Katsuyuki Murata. Associations between blood arsenic and urinary arsenic species concentrations as an exposure characterization tool. The Science of the total environment. 2021 Jan; 750(?):141517. doi: 10.1016/j.scitotenv.2020.141517. [PMID: 32829259]
  • Monika Gąsecka, Kinga Drzewiecka, Zuzanna Magdziak, Aneta Piechalak, Anna Budka, Bogusława Waliszewska, Kinga Szentner, Piotr Goliński, Przemysław Niedzielski, Sylwia Budzyńska, Mirosław Mleczek. Arsenic uptake, speciation and physiological response of tree species (Acer pseudoplatanus, Betula pendula and Quercus robur) treated with dimethylarsinic acid. Chemosphere. 2021 Jan; 263(?):127859. doi: 10.1016/j.chemosphere.2020.127859. [PMID: 32841871]
  • Zhenzhen Cao, Jiuyue Pan, Yongjie Yang, Zhaoyun Cao, Ping Xu, Mingxue Chen, Meiyan Guan. Water management affects arsenic uptake and translocation by regulating arsenic bioavailability, transporter expression and thiol metabolism in rice (Oryza sativa L.). Ecotoxicology and environmental safety. 2020 Dec; 206(?):111208. doi: 10.1016/j.ecoenv.2020.111208. [PMID: 32871521]
  • Daniel R Doerge, Nathan C Twaddle, Mona I Churchwell, Frederick A Beland. Reduction by, ligand exchange among, and covalent binding to glutathione and cellular thiols link metabolism and disposition of dietary arsenic species with toxicity. Environment international. 2020 11; 144(?):106086. doi: 10.1016/j.envint.2020.106086. [PMID: 32889486]
  • Gretchen E Dykes, Nikhil R Chari, Angelia L Seyfferth. Si-induced DMA desorption is not the driver for enhanced DMA availability after Si addition to flooded soils. The Science of the total environment. 2020 Oct; 739(?):139906. doi: 10.1016/j.scitotenv.2020.139906. [PMID: 32758940]
  • Beatrice Bocca, Anna Pino, Liza Vecchi Brumatti, Valentina Rosolen, Luca Ronfani, Jenny D'Aversa, Flavia Ruggieri, Francesco Petrucci, Gemma Calamandrei, Fabio Barbone, Alessandro Alimonti. Children exposure to inorganic and organic arsenic metabolites: A cohort study in Northeast Italy. Environmental pollution (Barking, Essex : 1987). 2020 Oct; 265(Pt B):114826. doi: 10.1016/j.envpol.2020.114826. [PMID: 32454361]
  • Jiating Wang, Guiwei Zhang, Zeheng Lin, Yu Luo, Heng Fang, Linjie Yang, Jinying Xie, Lianxian Guo. Determination of arsenicals in mouse tissues after simulated exposure to arsenic from rice for sixteen weeks and the effects on histopathological features. Ecotoxicology and environmental safety. 2020 Sep; 200(?):110742. doi: 10.1016/j.ecoenv.2020.110742. [PMID: 32470681]
  • Mark Button, Iris Koch, Michael J Watts, Kenneth J Reimer. Arsenic speciation in the bracket fungus Fomitopsis betulina from contaminated and pristine sites. Environmental geochemistry and health. 2020 Sep; 42(9):2723-2732. doi: 10.1007/s10653-019-00506-0. [PMID: 31897873]
  • Maria Ă'ngela de B C Menezes, Ingrid Falnoga, Zdenka Ĺ Lejkovec, Radojko JaÄ imoviÄ, Nilton Couto, Eleonora Deschamps, Jadran Faganeli. Arsenic in Sediments, Soil and Plants in a Remediated Area of the Iron Quadrangle, Brazil, and its Accumulation and Biotransformation in Eleocharis geniculata. Acta chimica Slovenica. 2020 Sep; 67(3):985-991. doi: 10.17344/acsi.2019.5760. [PMID: 33533426]
  • Farith González-Martínez, Daniel Sánchez-Rodas, Nelson M Varela, Christopher A Sandoval, Luis A Quiñones, Boris Johnson-Restrepo. As3MT and GST Polymorphisms Influencing Arsenic Metabolism in Human Exposure to Drinking Groundwater. International journal of molecular sciences. 2020 Jul; 21(14):. doi: 10.3390/ijms21144832. [PMID: 32650499]
  • Magdalena Jabłońska-Czapla, Piotr Zerzucha, Katarzyna Grygoyć. Impact of River Water and Bottom Sediment Pollution on Accumulation of Metal(loid)s and Arsenic Species in the Coastal Plants Stuckenia pectinata L., Galium aparine L., and Urtica dioica L.: A Chemometric and Environmental Study. Archives of environmental contamination and toxicology. 2020 Jul; 79(1):60-79. doi: 10.1007/s00244-020-00727-w. [PMID: 32285162]
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