Dimethylglycine (BioDeep_00000002864)

 

Secondary id: BioDeep_00000400250

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


N-Methylsarcosine N,N-dimethyl-glycine

化学式: C4H9NO2 (103.0633254)
中文名称: N,N-二甲基甘氨酸, 二甲基甘氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.97%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Dimethylglycine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dimethylglycine (retrieved 2024-09-18) (BioDeep RN: BioDeep_00000002864). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN(C)CC(=O)O
InChI: InChI=1S/C4H9NO2/c1-5(2)3-4(6)7/h3H2,1-2H3,(H,6,7)

描述信息

Dimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N,N-dimethylglycine by betaine-homocysteine methyltransferase. DMG in the urine is a biomarker for the consumption of legumes. It is also a microbial metabolite (PMID: 25901889).
Dimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into Glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N, N-dimethylglycine by betaine-homocysteine methyltransferase. [HMDB]. Dimethylglycine in the urine is a biomarker for the consumption of legumes.

N,N-Dimethylglycine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1118-68-9 (retrieved 2024-07-16) (CAS RN: 1118-68-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

N-Methylsarcosine is an amino acid building block for protein, found in a small amount in the body.

同义名列表

18 个代谢物同义名

N-Methylsarcosine N,N-dimethyl-glycine; Dimethylglycine, monopotassium salt; N,N-Dimethylglycine hydrochloride; Dimethylglycine monohydrochloride; 2-(N,N-Dimethylamino)acetic acid; Dimethylglycine, calcium salt; N,N-Dimethylaminoacetic acid; Dimethylglycine, sodium salt; 2-(Dimethylamino)acetic acid; (Dimethylamino)acetic acid; N,N-Dimethylaminoacetate; 2-(Dimethylamino)acetate; (Dimethylamino)acetate; N,N-dimethylglycine; N-Methylsarcosine; Dimethylglycine; DMG; Dimethylglycine



数据库引用编号

35 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

67 个相关的代谢反应过程信息。

Reactome(5)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(59)

PharmGKB(0)

2 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

  • Hong Yao, Yan Hu, Haibing Tong, Shourong Shi. Dimethylglycine Alleviates Metabolic Dysfunction-Associated Fatty Liver Disease by Improving the Circulating Estrogen Level via Gut Staphylococcus. Journal of agricultural and food chemistry. 2023 Dec; ?(?):. doi: 10.1021/acs.jafc.3c07075. [PMID: 38131116]
  • Sifiso S Makhathini, Calvin A Omolo, Lucy W Kiruri, Pavan Walvekar, Nikita Devnarain, Chunderika Mocktar, Thirumala Govender. Synthesis of pH-responsive dimethylglycine surface-modified branched lipids for targeted delivery of antibiotics. Chemistry and physics of lipids. 2022 11; 249(?):105241. doi: 10.1016/j.chemphyslip.2022.105241. [PMID: 36152880]
  • Kaiwen Bai, Luyi Jiang, Chengheng Wei, Qiming Li, Lili Zhang, Jingfei Zhang, Tian Wang. Dimethylglycine sodium salt activates Nrf2/SIRT1/PGC1α leading to the recovery of muscle stem cell dysfunction in newborns with intrauterine growth restriction. Free radical biology & medicine. 2022 May; 184(?):89-98. doi: 10.1016/j.freeradbiomed.2022.04.004. [PMID: 35405266]
  • Daisuke Watase, Shuichi Setoguchi, Nami Nagata-Akaho, Shotaro Goto, Hirofumi Yamakawa, Ayano Yamada, Mitsuhisa Koga, Yoshiharu Karube, Kazuhisa Matsunaga, Jiro Takata. Cationic N,N-Dimethylglycine Ester Prodrug of 2R-α-Tocotrienol Promotes Intestinal Absorption via Efficient Self-Micellization with Intrinsic Bile Acid Anion. Molecules (Basel, Switzerland). 2022 Apr; 27(9):. doi: 10.3390/molecules27092727. [PMID: 35566078]
  • Hong Yao, Yan Hu, Qiang Wang, Yijian Zhang, Kaiqing Rao, Shourong Shi. Effects of dietary dimethylglycine supplementation on laying performance, egg quality, and tissue index of hens during late laying period. Poultry science. 2022 Feb; 101(2):101610. doi: 10.1016/j.psj.2021.101610. [PMID: 34936951]
  • Xiong-Fei Pan, Jae Jeong Yang, Xiao-Ou Shu, Steven C Moore, Nicholette D Palmer, Marta Guasch-Ferré, David M Herrington, Sei Harada, Heather Eliassen, Thomas J Wang, Robert E Gerszten, Demetrius Albanes, Ioanna Tzoulaki, Ibrahim Karaman, Paul Elliott, Huilian Zhu, Lynne E Wagenknecht, Wei Zheng, Hui Cai, Qiuyin Cai, Charles E Matthews, Cristina Menni, Katie A Meyer, Loren P Lipworth, Jennifer Ose, Myriam Fornage, Cornelia M Ulrich, Danxia Yu. Associations of circulating choline and its related metabolites with cardiometabolic biomarkers: an international pooled analysis. The American journal of clinical nutrition. 2021 09; 114(3):893-906. doi: 10.1093/ajcn/nqab152. [PMID: 34020444]
  • Kaiwen Bai, Luyi Jiang, Qiming Li, Jingfei Zhang, Lili Zhang, Tian Wang. Dietary dimethylglycine sodium salt supplementation improves growth performance, redox status, and skeletal muscle function of intrauterine growth-restricted weaned piglets. Journal of animal science. 2021 Jul; 99(7):. doi: 10.1093/jas/skab186. [PMID: 34107017]
  • Yi Qun Liu, Ling He Huang, Pei Pei Liu, Qing Bin Xing, Feng Han, Qin Wang, Shu Rong Chen, Kimio Sugiyama, Xue Song Xiang, Zhen Wu Huang. Effect of N, N-Dimethylglycine on Homocysteine Metabolism in Rats Fed Folate-Sufficient and Folate-Deficient Diets. Biomedical and environmental sciences : BES. 2021 May; 34(5):356-363. doi: 10.3967/bes2021.047. [PMID: 34059172]
  • Elisabetta Tarentini, Giulia Odorici, Valeria Righi, Alessia Paganelli, Luca Giacomelli, Valentina Mirisola, Adele Mucci, Luisa Benassi, Elisabetta D'Aversa, Claudia Lasagni, Shaniko Kaleci, Eva Reali, Cristina Magnoni. Integrated metabolomic analysis and cytokine profiling define clusters of immuno-metabolic correlation in new-onset psoriasis. Scientific reports. 2021 05; 11(1):10472. doi: 10.1038/s41598-021-89925-7. [PMID: 34006909]
  • Yasuhiko Kato, Hitoshi Kuwabara, Takashi Okada, Toshio Munesue, Seico Benner, Miho Kuroda, Masaki Kojima, Walid Yassin, Yosuke Eriguchi, Yosuke Kameno, Chihiro Murayama, Tomoko Nishimura, Kenji Tsuchiya, Kiyoto Kasai, Norio Ozaki, Hirotaka Kosaka, Hidenori Yamasue. Oxytocin-induced increase in N,N-dimethylglycine and time course of changes in oxytocin efficacy for autism social core symptoms. Molecular autism. 2021 02; 12(1):15. doi: 10.1186/s13229-021-00423-z. [PMID: 33622389]
  • Yingna Wei, Bei Wang. The expression levels of plasma dimethylglycine (DMG), human maternally expressed gene 3 (MEG3), and Apelin-12 in patients with acute myocardial infarction and their clinical significance. Annals of palliative medicine. 2021 Feb; 10(2):2175-2183. doi: 10.21037/apm-21-122. [PMID: 33725773]
  • Christopher Papandreou, Mònica Bulló, Pablo Hernández-Alonso, Miguel Ruiz-Canela, Jun Li, Marta Guasch-Ferré, Estefanía Toledo, Clary Clish, Dolores Corella, Ramon Estruch, Emilio Ros, Montserrat Fitó, Angel Alonso-Gómez, Miquel Fiol, José M Santos-Lozano, Lluís Serra-Majem, Liming Liang, Miguel A Martínez-González, Frank B Hu, Jordi Salas-Salvadó. Choline Metabolism and Risk of Atrial Fibrillation and Heart Failure in the PREDIMED Study. Clinical chemistry. 2021 01; 67(1):288-297. doi: 10.1093/clinchem/hvaa224. [PMID: 33257943]
  • Hyo Kyozuka, Toma Fukuda, Tsuyoshi Murata, Yuta Endo, Aya Kanno, Shun Yasuda, Akiko Yamaguchi, Miho Ono, Akiko Sato, Koichi Hashimoto, Keiya Fujimori. Comprehensive metabolomic analysis of first-trimester serum identifies biomarkers of early-onset hypertensive disorder of pregnancy. Scientific reports. 2020 08; 10(1):13857. doi: 10.1038/s41598-020-70974-3. [PMID: 32807817]
  • Maria F Mujica-Coopman, Amy Tan, Theresa H Schroder, Graham Sinclair, Hilary D Vallance, Yvonne Lamers. Serum Betaine and Dimethylglycine Are Higher in South Asian Compared with European Pregnant Women in Canada, with Betaine and Total Homocysteine Inversely Associated in Early and Midpregnancy, Independent of Ethnicity. The Journal of nutrition. 2019 12; 149(12):2145-2155. doi: 10.1093/jn/nxz178. [PMID: 31504713]
  • Lotte Smolders, Nicole J W de Wit, Michiel G J Balvers, Rima Obeid, Marc M M Vissers, Diederik Esser. Natural Choline from Egg Yolk Phospholipids Is More Efficiently Absorbed Compared with Choline Bitartrate; Outcomes of A Randomized Trial in Healthy Adults. Nutrients. 2019 Nov; 11(11):. doi: 10.3390/nu11112758. [PMID: 31766273]
  • Yu-Feng Du, Yuan Wei, Jing Yang, Zi-Yi Cheng, Xi-Fang Zuo, Tian-Chen Wu, Hui-Feng Shi, Xiao-Li Wang. Maternal betaine status, but not that of choline or methionine, is inversely associated with infant birth weight. The British journal of nutrition. 2019 06; 121(11):1279-1286. doi: 10.1017/s0007114519000497. [PMID: 30837009]
  • Chengcheng Feng, Kaiwen Bai, Anan Wang, Xiaoke Ge, Yongwei Zhao, Lili Zhang, Tian Wang. Effects of dimethylglycine sodium salt supplementation on growth performance, hepatic antioxidant capacity, and mitochondria-related gene expression in weanling piglets born with low birth weight1. Journal of animal science. 2018 Sep; 96(9):3791-3803. doi: 10.1093/jas/sky233. [PMID: 29931075]
  • Rima Obeid, Hussain M Awwad, Astrid Ines Knell, Ulrich Hübner, Jürgen Geisel. Glucose and Fat Tolerance Tests Induce Differential Responses in Plasma Choline Metabolites in Healthy Subjects. Nutrients. 2018 Sep; 10(9):. doi: 10.3390/nu10091209. [PMID: 30200465]
  • Alejandra M Wiedeman, Cecil M Y Chau, Ruth E Grunau, Deanna McCarthy, Karin Yurko-Mauro, Roger A Dyer, Sheila M Innis, Angela M Devlin. Plasma Betaine Is Positively Associated with Developmental Outcomes in Healthy Toddlers at Age 2 Years Who Are Not Meeting the Recommended Adequate Intake for Dietary Choline. The Journal of nutrition. 2018 08; 148(8):1309-1314. doi: 10.1093/jn/nxy108. [PMID: 29986040]
  • Rima Obeid, Hussain M Awwad, Markus Keller, Juergen Geisel. Trimethylamine-N-oxide and its biological variations in vegetarians. European journal of nutrition. 2017 Dec; 56(8):2599-2609. doi: 10.1007/s00394-016-1295-9. [PMID: 27562778]
  • Michael Lever, Christopher J McEntyre, Peter M George, Stephen T Chambers. Is N,N-dimethylglycine N-oxide a choline and betaine metabolite?. Biological chemistry. 2017 06; 398(7):775-784. doi: 10.1515/hsz-2016-0261. [PMID: 27902449]
  • Kiyoshi Fukuhara, Akiko Ohno, Ruri Kikura-Hanajiri. A Metabolic Study on the Biochemical Effects of Chiral Illegal Drugs in Rats Using 1H-NMR Spectroscopy. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2017; 137(9):1147-1154. doi: 10.1248/yakushi.17-00046. [PMID: 28867701]
  • Robin Myte, Björn Gylling, Jörn Schneede, Per Magne Ueland, Jenny Häggström, Johan Hultdin, Göran Hallmans, Ingegerd Johansson, Richard Palmqvist, Bethany Van Guelpen. Components of One-carbon Metabolism Other than Folate and Colorectal Cancer Risk. Epidemiology (Cambridge, Mass.). 2016 11; 27(6):787-96. doi: 10.1097/ede.0000000000000529. [PMID: 27367522]
  • Jose M Colomina, Pere Cavallé-Busquets, Sílvia Fernàndez-Roig, Pol Solé-Navais, Joan D Fernandez-Ballart, Mónica Ballesteros, Per M Ueland, Klaus Meyer, Michelle M Murphy. Maternal Folate Status and the BHMT c.716G>A Polymorphism Affect the Betaine Dimethylglycine Pathway during Pregnancy. Nutrients. 2016 Oct; 8(10):. doi: 10.3390/nu8100621. [PMID: 27735840]
  • Mauro Forteschi, Angelo Zinellu, Stefano Assaretti, Arduino A Mangoni, Gianfranco Pintus, Ciriaco Carru, Salvatore Sotgia. An isotope dilution capillary electrophoresis/tandem mass spectrometry (CE-MS/MS) method for the simultaneous measurement of choline, betaine, and dimethylglycine concentrations in human plasma. Analytical and bioanalytical chemistry. 2016 Oct; 408(26):7505-12. doi: 10.1007/s00216-016-9848-6. [PMID: 27503542]
  • Pol Solé-Navais, Pere Cavallé-Busquets, Joan D Fernandez-Ballart, Michelle M Murphy. Early pregnancy B vitamin status, one carbon metabolism, pregnancy outcome and child development. Biochimie. 2016 Jul; 126(?):91-6. doi: 10.1016/j.biochi.2015.12.003. [PMID: 26700149]
  • Megan N Hall, Caitlin G Howe, Xinhua Liu, Marie A Caudill, Olga Malysheva, Vesna Ilievski, Angela M Lomax-Luu, Faruque Parvez, Abu B Siddique, Hasan Shahriar, Mohammad N Uddin, Tariqul Islam, Joseph H Graziano, Mary V Gamble. Supplementation with Folic Acid, but Not Creatine, Increases Plasma Betaine, Decreases Plasma Dimethylglycine, and Prevents a Decrease in Plasma Choline in Arsenic-Exposed Bangladeshi Adults. The Journal of nutrition. 2016 05; 146(5):1062-7. doi: 10.3945/jn.115.227132. [PMID: 27052531]
  • Vegard Lysne, Elin Strand, Gard F T Svingen, Bodil Bjørndal, Eva R Pedersen, Øivind Midttun, Thomas Olsen, Per M Ueland, Rolf K Berge, Ottar Nygård. Peroxisome Proliferator-Activated Receptor Activation is Associated with Altered Plasma One-Carbon Metabolites and B-Vitamin Status in Rats. Nutrients. 2016 Jan; 8(1):. doi: 10.3390/nu8010026. [PMID: 26742069]
  • Kaiwen Bai, Wen Xu, Jingfei Zhang, Tao Kou, Yu Niu, Xiaoli Wan, Lili Zhang, Chao Wang, Tian Wang. Assessment of Free Radical Scavenging Activity of Dimethylglycine Sodium Salt and Its Role in Providing Protection against Lipopolysaccharide-Induced Oxidative Stress in Mice. PloS one. 2016; 11(5):e0155393. doi: 10.1371/journal.pone.0155393. [PMID: 27171376]
  • Martin Magnusson, Thomas J Wang, Clary Clish, Gunnar Engström, Peter Nilsson, Robert E Gerszten, Olle Melander. Dimethylglycine Deficiency and the Development of Diabetes. Diabetes. 2015 Aug; 64(8):3010-6. doi: 10.2337/db14-1863. [PMID: 25795213]
  • Wolfgang Bernhard, Marco Raith, Rebecca Kunze, Vera Koch, Martin Heni, Christoph Maas, Harald Abele, Christian F Poets, Axel R Franz. Choline concentrations are lower in postnatal plasma of preterm infants than in cord plasma. European journal of nutrition. 2015 Aug; 54(5):733-41. doi: 10.1007/s00394-014-0751-7. [PMID: 25148882]
  • Carly E Visentin, Shannon Masih, Lesley Plumptre, Olga Malysheva, Daiva E Nielsen, Kyoung-Jin Sohn, Anna Ly, Andrea Y Lausman, Howard Berger, Ruth Croxford, Ahmed El-Sohemy, Marie A Caudill, Deborah L O'Connor, Young-In Kim. Maternal Choline Status, but Not Fetal Genotype, Influences Cord Plasma Choline Metabolite Concentrations. The Journal of nutrition. 2015 Jul; 145(7):1491-7. doi: 10.3945/jn.115.211136. [PMID: 25972528]
  • Vegard Lysne, Bodil Bjørndal, Rita Vik, Jan Erik Nordrehaug, Jon Skorve, Ottar Nygård, Rolf K Berge. A Protein Extract from Chicken Reduces Plasma Homocysteine in Rats. Nutrients. 2015 Jun; 7(6):4498-511. doi: 10.3390/nu7064498. [PMID: 26053618]
  • Gard F T Svingen, Hall Schartum-Hansen, Per M Ueland, Eva R Pedersen, Reinhard Seifert, Marta Ebbing, Kaare H Bønaa, Gunnar Mellgren, Dennis W T Nilsen, Jan E Nordrehaug, Jannike Øyen, Ottar Nygård. Elevated plasma dimethylglycine is a risk marker of mortality in patients with coronary heart disease. European journal of preventive cardiology. 2015 Jun; 22(6):743-52. doi: 10.1177/2047487314529351. [PMID: 24671904]
  • Christopher J McEntyre, Michael Lever, Stephen T Chambers, Peter M George, Sandy Slow, Jane L Elmslie, Christopher M Florkowski, Helen Lunt, Jeremy D Krebs. Variation of betaine, N,N-dimethylglycine, choline, glycerophosphorylcholine, taurine and trimethylamine-N-oxide in the plasma and urine of overweight people with type 2 diabetes over a two-year period. Annals of clinical biochemistry. 2015 May; 52(Pt 3):352-60. doi: 10.1177/0004563214545346. [PMID: 25013088]
  • J Øyen, G F T Svingen, C G Gjesdal, G S Tell, P M Ueland, V Lysne, E M Apalset, K Meyer, S E Vollset, O K Nygård. Plasma dimethylglycine, nicotine exposure and risk of low bone mineral density and hip fracture: the Hordaland Health Study. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA. 2015 May; 26(5):1573-83. doi: 10.1007/s00198-015-3030-4. [PMID: 25616506]
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  • Elisa Brasili, Elena Mengheri, Alberta Tomassini, Giorgio Capuani, Marianna Roselli, Alberto Finamore, Fabio Sciubba, Federico Marini, Alfredo Miccheli. Lactobacillus acidophilus La5 and Bifidobacterium lactis Bb12 induce different age-related metabolic profiles revealed by 1H-NMR spectroscopy in urine and feces of mice. The Journal of nutrition. 2013 Oct; 143(10):1549-57. doi: 10.3945/jn.113.177105. [PMID: 23946343]
  • Gard Frodahl Tveitevåg Svingen, Per Magne Ueland, Eva Kristine Ringdal Pedersen, Hall Schartum-Hansen, Reinhard Seifert, Marta Ebbing, Kjetil Halvorsen Løland, Grethe S Tell, Ottar Nygård. Plasma dimethylglycine and risk of incident acute myocardial infarction in patients with stable angina pectoris. Arteriosclerosis, thrombosis, and vascular biology. 2013 Aug; 33(8):2041-8. doi: 10.1161/atvbaha.113.301714. [PMID: 23723367]
  • Ranwa Alsayed, Faizeh Al Quobaili, Samir Srour, Jürgen Geisel, Rima Obeid. Elevated dimethylglycine in blood of children with congenital heart defects and their mothers. Metabolism: clinical and experimental. 2013 Aug; 62(8):1074-80. doi: 10.1016/j.metabol.2013.01.024. [PMID: 23481916]
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