Dichloroacetate (BioDeep_00000003222)

   

natural product Volatile Flavor Compounds


代谢物信息卡片


2,2-dichloroacetic acid

化学式: C2H2Cl2O2 (127.9431852)
中文名称: 二氯乙酸标准溶液, 二氯乙酸
谱图信息: 最多检出来源 Viridiplantae(plant) 0.75%

分子结构信息

SMILES: C(C(=O)O)(Cl)Cl
InChI: InChI=1S/C2H2Cl2O2/c3-1(4)2(5)6/h1H,(H,5,6)

描述信息

An organochlorine compound comprising acetic acid carrying two chloro substituents at the 2-position. It occurs in nature in seaweed, Asparagopsis taxiformis.
KEIO_ID D160
KEIO_ID D034

同义名列表

6 个代谢物同义名

2,2-dichloroacetic acid; DICHLOROACETIC ACID; Dichloroacetate; Dichloroacetate(2); Dichloroacetate; Dichloroacetic acid



数据库引用编号

28 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)

15 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

  • Théo Ciccia, Pascal Pandard, Philippe Ciffroy, Nastassia Urien, Léo Lafay, Anne Bado-Nilles. Sub-lethal toxicity of five disinfection by-products on microalgae determined by flow cytometry - Lines of evidence for adverse outcome pathways. Ecotoxicology and environmental safety. 2023 Nov; 266(?):115582. doi: 10.1016/j.ecoenv.2023.115582. [PMID: 37862747]
  • Chong Liu, Yan-Ling Deng, Xiao-Qiong Yuan, Pan-Pan Chen, Yu Miao, Qiong Luo, Min Zhang, Fei-Peng Cui, Wen Yao, Jia-Yue Zeng, Tian Shi, Ting-Ting Lu, Yu-Feng Li, Wen-Qing Lu, Qiang Zeng. Exposure to disinfection by-products and reproductive hormones among women: Results from the Tongji Reproductive and Environmental (TREE) study. Environmental research. 2022 06; 209(?):112863. doi: 10.1016/j.envres.2022.112863. [PMID: 35123968]
  • Serene Joseph, Mengchen Li, Sicong Zhang, Lloyd Horne, Peter W Stacpoole, Stephanie E Wohlgemuth, Arthur S Edison, Charles Wood, Maureen Keller-Wood. Sodium dichloroacetate stimulates cardiac mitochondrial metabolism and improves cardiac conduction in the ovine fetus during labor. American journal of physiology. Regulatory, integrative and comparative physiology. 2022 01; 322(1):R83-R98. doi: 10.1152/ajpregu.00185.2021. [PMID: 34851727]
  • Bassam Lajin, Simone Braeuer, Jan Borovička, Walter Goessler. Is the water disinfection by-product dichloroacetic acid biosynthesized in the edible mushroom Russula nigricans?. Chemosphere. 2021 Oct; 281(?):130819. doi: 10.1016/j.chemosphere.2021.130819. [PMID: 33991903]
  • Li Ren, Yanwen Zhang, Yining Xin, Guo Chen, Xiaoxiao Sun, Yingqi Chen, Bin He. Dysfunction in Sertoli cells participates in glucocorticoid-induced impairment of spermatogenesis. Molecular reproduction and development. 2021 06; 88(6):405-415. doi: 10.1002/mrd.23515. [PMID: 34032349]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Jie Sun, Xiuqin Cheng, Shubo Pan, Liangjing Wang, Wenhuan Dou, Jie Liu, Xiaohua Shi. Dichloroacetate attenuates the stemness of colorectal cancer cells via trigerring ferroptosis through sequestering iron in lysosomes. Environmental toxicology. 2021 Apr; 36(4):520-529. doi: 10.1002/tox.23057. [PMID: 33166055]
  • Wei Wei, Qiuying Dong, Wenbo Jiang, Yue Wang, Yingying Chen, Tianshu Han, Changhao Sun. Dichloroacetic acid-induced dysfunction in rat hippocampus and the protective effect of curcumin. Metabolic brain disease. 2021 04; 36(4):545-556. doi: 10.1007/s11011-020-00657-5. [PMID: 33411217]
  • Rabina Mainali, Manal Zabalawi, David Long, Nancy Buechler, Ellen Quillen, Chia-Chi Key, Xuewei Zhu, John S Parks, Cristina Furdui, Peter W Stacpoole, Jennifer Martinez, Charles E McCall, Matthew A Quinn. Dichloroacetate reverses sepsis-induced hepatic metabolic dysfunction. eLife. 2021 02; 10(?):. doi: 10.7554/elife.64611. [PMID: 33616039]
  • Rodrigo S do Nascimento, Marcia K Nagamine, Gabriela F De Toledo, Lucas M Chaible, Marcello V Tedardi, Murilo P Del-Grande, Ivone I M da Fonseca, Maria L Z Dagli. Sodium dichloroacetate attenuates the growth of B16-F10 melanoma in vitro and in vivo: an opportunity for drug repurposing. Anti-cancer drugs. 2021 02; 32(2):111-116. doi: 10.1097/cad.0000000000001013. [PMID: 33395068]
  • Edwin J Squirewell, Marci G Smeltz, Laura Rowland-Faux, Lloyd P Horne, Peter W Stacpoole, Margaret O James. Effects of Multiple Doses of Dichloroacetate on GSTZ1 Expression and Activity in Liver and Extrahepatic Tissues of Young and Adult Rats. Drug metabolism and disposition: the biological fate of chemicals. 2020 11; 48(11):1217-1223. doi: 10.1124/dmd.120.000142. [PMID: 32873593]
  • Edward R Smith, Timothy D Hewitson. TGF-β1 is a regulator of the pyruvate dehydrogenase complex in fibroblasts. Scientific reports. 2020 10; 10(1):17914. doi: 10.1038/s41598-020-74919-8. [PMID: 33087819]
  • Serene Joseph, Abhisheak Sharma, Lloyd P Horne, Charles E Wood, Taimour Langaee, Margaret O James, Peter W Stacpoole, Maureen Keller-Wood. Pharmacokinetic and Biochemical Profiling of Sodium Dichloroacetate in Pregnant Ewes and Fetuses. Drug metabolism and disposition: the biological fate of chemicals. 2020 06; 49(6):451-458. doi: 10.1124/dmd.120.000330. [PMID: 33811107]
  • Xiaoxiao Zhang, Zhonglin Chen, Jimin Shen, Shengxin Zhao, Jing Kang, Wei Chu, Yaoyu Zhou, Binyuan Wang. Formation and interdependence of disinfection byproducts during chlorination of natural organic matter in a conventional drinking water treatment plant. Chemosphere. 2020 Mar; 242(?):125227. doi: 10.1016/j.chemosphere.2019.125227. [PMID: 31704522]
  • Tangzhiming Li, Suqi Li, Yilu Feng, Xiaofang Zeng, Shaohong Dong, Jianghua Li, Lihuang Zha, Hui Luo, Lin Zhao, Bin Liu, Ziwei Ou, Wenchao Lin, Mengqiu Zhang, Sheng Li, Qiuqiong Jiang, Qiangqiang Qi, Qingyao Xu, Zaixin Yu. Combination of Dichloroacetate and Atorvastatin Regulates Excessive Proliferation and Oxidative Stress in Pulmonary Arterial Hypertension Development via p38 Signaling. Oxidative medicine and cellular longevity. 2020; 2020(?):6973636. doi: 10.1155/2020/6973636. [PMID: 32617141]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Byong-Keol Min, Chang Joo Oh, Sungmi Park, Ji-Min Lee, Younghoon Go, Bo-Yoon Park, Hyeon-Ji Kang, Dong Wook Kim, Jeong-Eun Kim, Eun Kyung Yoo, Hui Eon Kim, Mi-Jin Kim, Yong Hyun Jeon, Yong-Hoon Kim, Chul-Ho Lee, Jae-Han Jeon, In-Kyu Lee. Therapeutic effect of dichloroacetate against atherosclerosis via hepatic FGF21 induction mediated by acute AMPK activation. Experimental & molecular medicine. 2019 09; 51(10):1-12. doi: 10.1038/s12276-019-0315-2. [PMID: 31570705]
  • Jiajun Huang, Jingjing Du, Wanjun Lin, Ze Long, Na Zhang, Xiaoming Huang, Ying Xie, Liang Liu, Wenzhe Ma. Regulation of lactate production through p53/β-enolase axis contributes to statin-associated muscle symptoms. EBioMedicine. 2019 Jul; 45(?):251-260. doi: 10.1016/j.ebiom.2019.06.003. [PMID: 31201144]
  • Qingqing Wei, Jennifer Su, Guie Dong, Ming Zhang, Yuqing Huo, Zheng Dong. Glycolysis inhibitors suppress renal interstitial fibrosis via divergent effects on fibroblasts and tubular cells. American journal of physiology. Renal physiology. 2019 06; 316(6):F1162-F1172. doi: 10.1152/ajprenal.00422.2018. [PMID: 30969803]
  • Agnieszka Korga, Marta Ostrowska, Magdalena Iwan, Mariola Herbet, Jaroslaw Dudka. Inhibition of glycolysis disrupts cellular antioxidant defense and sensitizes HepG2 cells to doxorubicin treatment. FEBS open bio. 2019 05; 9(5):959-972. doi: 10.1002/2211-5463.12628. [PMID: 30973680]
  • Yi-Xin Wang, Chong Liu, Ying-Jun Chen, Peng Duan, Qi Wang, Chao Chen, Yang Sun, Li-Li Huang, Liang Wang, Chen Chen, Jin Li, Song-Hua Ai, Zhen Huang, Li Sun, Zhen-Zhen Wan, An Pan, Tian-Qing Meng, Wen-Qing Lu. Profiles, variability and predictors of concentrations of blood trihalomethanes and urinary haloacetic acids along pregnancy among 1760 Chinese women. Environmental research. 2019 05; 172(?):665-674. doi: 10.1016/j.envres.2019.03.017. [PMID: 30878738]
  • Salah Mohamed El Sayed, Hussam Baghdadi, Nagwa Sayed Ahmed, Hamdi H Almaramhy, Ahmed Al-Amir Mahmoud, Samer Ahmed El-Sawy, Mongi Ayat, Momen Elshazley, Wafaa Abdel-Aziz, Haitham Mahmoud Abdel-Latif, Walaa Ibrahim, Moutasem Salih Aboonq. Dichloroacetate is an antimetabolite that antagonizes acetate and deprives cancer cells from its benefits: A novel evidence-based medical hypothesis. Medical hypotheses. 2019 Jan; 122(?):206-209. doi: 10.1016/j.mehy.2018.11.012. [PMID: 30593413]
  • I V Prokhorova, O N Pyaskovskaya, D L Kolesnik, G I Solyanik. Influence of metformin, sodium dichloroacetate and their combination on the hematological and biochemical blood parameters of rats with gliomas C6. Experimental oncology. 2018 Oct; 40(3):205-210. doi: 10.31768/2312-8852.2018.40(3):205-210. [PMID: 30284997]
  • Stephan C Jahn, Marci G Smeltz, Zhiwei Hu, Laura Rowland-Faux, Guo Zhong, Ryan J Lorenzo, Katherine V Cisneros, Peter W Stacpoole, Margaret O James. Regulation of dichloroacetate biotransformation in rat liver and extrahepatic tissues by GSTZ1 expression and chloride concentration. Biochemical pharmacology. 2018 06; 152(?):236-243. doi: 10.1016/j.bcp.2018.04.001. [PMID: 29626439]
  • Taimour Langaee, Richard Wagner, Lloyd P Horne, Lee Ann Lawson, Cecilia Becker, Mohamed Shahin, Petr Starostik, Peter W Stacpoole. Personalized Dosing of Dichloroacetate Using GSTZ1 Clinical Genotyping Assay. Genetic testing and molecular biomarkers. 2018 Apr; 22(4):266-269. doi: 10.1089/gtmb.2017.0261. [PMID: 29641284]
  • Hong-Yan Lin, Hong-Wei Han, Wen-Xue Sun, Yu-Shun Yang, Cheng-Yi Tang, Gui-Hua Lu, Jin-Liang Qi, Xiao-Ming Wang, Yong-Hua Yang. Design and characterization of α-lipoic acyl shikonin ester twin drugs as tubulin and PDK1 dual inhibitors. European journal of medicinal chemistry. 2018 Jan; 144(?):137-150. doi: 10.1016/j.ejmech.2017.12.019. [PMID: 29268130]
  • Mohammed Albatany, Alex Li, Susan Meakin, Robert Bartha. Dichloroacetate induced intracellular acidification in glioblastoma: in vivo detection using AACID-CEST MRI at 9.4 Tesla. Journal of neuro-oncology. 2018 Jan; 136(2):255-262. doi: 10.1007/s11060-017-2664-9. [PMID: 29143921]
  • Abrar Ul Haq Khan, Nerea Allende-Vega, Delphine Gitenay, Sabine Gerbal-Chaloin, Claire Gondeau, Dang-Nghiem Vo, Sana Belkahla, Stefania Orecchioni, Giovanna Talarico, Francesco Bertolini, Milica Bozic, Jose M Valdivielso, Fabienne Bejjani, Isabelle Jariel, Isabel C Lopez-Mejia, Lluis Fajas, Charles-Henri Lecellier, Javier Hernandez, Martine Daujat, Martin Villalba. The PDK1 Inhibitor Dichloroacetate Controls Cholesterol Homeostasis Through the ERK5/MEF2 Pathway. Scientific reports. 2017 09; 7(1):10654. doi: 10.1038/s41598-017-10339-5. [PMID: 28878225]
  • Amira El Arem, Lamia Lahouar, Emna Behija Saafi, Amira Thouri, Fatma Ghrairi, Zohra Houas, Fadoua Neffati, Lotfi Achour. Dichloroacetic acid-induced testicular toxicity in male rats and the protective effect of date fruit extract. BMC pharmacology & toxicology. 2017 04; 18(1):17. doi: 10.1186/s40360-017-0127-8. [PMID: 28431577]
  • Ramindhu Galgamuwa, Kristine Hardy, Jane E Dahlstrom, Anneke C Blackburn, Elize Wium, Melissa Rooke, Jean Y Cappello, Padmaja Tummala, Hardip R Patel, Aaron Chuah, Luyang Tian, Linda McMorrow, Philip G Board, Angelo Theodoratos. Dichloroacetate Prevents Cisplatin-Induced Nephrotoxicity without Compromising Cisplatin Anticancer Properties. Journal of the American Society of Nephrology : JASN. 2016 Nov; 27(11):3331-3344. doi: 10.1681/asn.2015070827. [PMID: 26961349]
  • Adam Kinnaird, Peter Dromparis, Bruno Saleme, Vikram Gurtu, Kristalee Watson, Roxane Paulin, Sotirios Zervopoulos, Trevor Stenson, Gopinath Sutendra, Desmond B Pink, Katia Carmine-Simmen, Ronald Moore, John D Lewis, Evangelos D Michelakis. Metabolic Modulation of Clear-cell Renal Cell Carcinoma with Dichloroacetate, an Inhibitor of Pyruvate Dehydrogenase Kinase. European urology. 2016 Apr; 69(4):734-744. doi: 10.1016/j.eururo.2015.09.014. [PMID: 26433571]
  • Theodoros Eleftheriadis, Maria Sounidaki, Georgios Pissas, Georgia Antoniadi, Vassilios Liakopoulos, Ioannis Stefanidis. In human alloreactive CD4⁺ T-cells, dichloroacetate inhibits aerobic glycolysis, induces apoptosis and favors differentiation towards the regulatory T-cell subset instead of effector T-cell subsets. Molecular medicine reports. 2016 Apr; 13(4):3370-6. doi: 10.3892/mmr.2016.4912. [PMID: 26935268]
  • Rafael Jaimes, Sarah Kuzmiak-Glancy, Daina M Brooks, Luther M Swift, Nikki G Posnack, Matthew W Kay. Functional response of the isolated, perfused normoxic heart to pyruvate dehydrogenase activation by dichloroacetate and pyruvate. Pflugers Archiv : European journal of physiology. 2016 Jan; 468(1):131-142. doi: 10.1007/s00424-015-1717-1. [PMID: 26142699]
  • Ezdihar Hassoun, Christopher Mettling. Dichloroacetate and Trichloroacetate Toxicity in AML12 Cells: Role of Oxidative Stress. Journal of biochemical and molecular toxicology. 2015 Nov; 29(11):508-12. doi: 10.1002/jbt.21720. [PMID: 26121004]
  • Emanuele Cotroneo, Ali Ashek, Lei Wang, John Wharton, Olivier Dubois, Sophie Bozorgi, Mark Busbridge, Kambiz N Alavian, Martin R Wilkins, Lan Zhao. Iron homeostasis and pulmonary hypertension: iron deficiency leads to pulmonary vascular remodeling in the rat. Circulation research. 2015 May; 116(10):1680-90. doi: 10.1161/circresaha.116.305265. [PMID: 25767292]
  • Albert L Shroads, Bonnie S Coats, Taimour Langaee, Jonathan J Shuster, Peter W Stacpoole. Chloral hydrate, through biotransformation to dichloroacetate, inhibits maleylacetoacetate isomerase and tyrosine catabolism in humans. Drug metabolism and personalized therapy. 2015 Mar; 30(1):49-55. doi: 10.1515/dmdi-2014-0015. [PMID: 25283137]
  • Suchandrima Saha, Monisankar Ghosh, Samir Kumar Dutta. A potent tumoricidal co-drug 'Bet-CA'--an ester derivative of betulinic acid and dichloroacetate selectively and synergistically kills cancer cells. Scientific reports. 2015 Jan; 5(?):7762. doi: 10.1038/srep07762. [PMID: 25585916]
  • Hong Sik Yoo, Blair U Bradford, Oksana Kosyk, Svitlana Shymonyak, Takeki Uehara, Leonard B Collins, Wanda M Bodnar, Louise M Ball, Avram Gold, Ivan Rusyn. Comparative analysis of the relationship between trichloroethylene metabolism and tissue-specific toxicity among inbred mouse strains: liver effects. Journal of toxicology and environmental health. Part A. 2015; 78(1):15-31. doi: 10.1080/15287394.2015.958417. [PMID: 25424544]
  • Hong Sik Yoo, Blair U Bradford, Oksana Kosyk, Takeki Uehara, Svitlana Shymonyak, Leonard B Collins, Wanda M Bodnar, Louise M Ball, Avram Gold, Ivan Rusyn. Comparative analysis of the relationship between trichloroethylene metabolism and tissue-specific toxicity among inbred mouse strains: kidney effects. Journal of toxicology and environmental health. Part A. 2015; 78(1):32-49. doi: 10.1080/15287394.2015.958418. [PMID: 25424545]
  • A L Shroads, B S Coats, C W McDonough, T Langaee, P W Stacpoole. Haplotype variations in glutathione transferase zeta 1 influence the kinetics and dynamics of chronic dichloroacetate in children. Journal of clinical pharmacology. 2015 Jan; 55(1):50-5. doi: 10.1002/jcph.371. [PMID: 25079374]
  • Robert Bacallao. Caveat emptor: if you have PKD, be careful of what you drink?. American journal of physiology. Renal physiology. 2014 Nov; 307(10):F1132-3. doi: 10.1152/ajprenal.00506.2014. [PMID: 25234314]
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  • Jacquelyn Cearfoss, Ezdihar Hassoun. The effects of a low vitamin E diet on dichloroacetate- and trichloroacetate-induced oxidative stress in the livers of mice. Journal of biochemical and molecular toxicology. 2012 Mar; 26(4):147-54. doi: 10.1002/jbt.20421. [PMID: 22447681]
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