2-Methylcitric acid (BioDeep_00000004313)

 

Secondary id: BioDeep_00001870390, BioDeep_00001874330

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid

化学式: C7H10O7 (206.0427)
中文名称: 2-甲基柠檬酸
谱图信息: 最多检出来源 Homo sapiens(feces) 33.73%

分子结构信息

SMILES: CC(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI: InChI=1S/C7H10O7/c1-3(5(10)11)7(14,6(12)13)2-4(8)9/h3,14H,2H2,1H3,(H,8,9)(H,10,11)(H,12,13)

描述信息

Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000, 232050), methylmalonic aciduria (MMA; OMIM 251000, 251120) and multiple carboxylase deficiency (OMIM 253260, 253270), which are inherited disorders. MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine (PMID: 17295121).
Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000, 232050), methylmalonic aciduria (MMA; OMIM 251000, 251120) and multiple carboxylase deficiency (OMIM 253260, 253270). MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine. (PMID: 17295121) [HMDB]
2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1].
2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1].
2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1].

同义名列表

15 个代谢物同义名

2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid; (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylic acid; 3-Carboxy-3-hydroxy-2-methylpentanedioic acid; (2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate; 2-Hydroxy-1,2,3-butanetricarboxylic acid; 2-Hydroxybutane-1,2,3-tricarboxylic acid; 2-Hydroxybutane-1,2,3-tricarboxylate; 2-Hydroxy-1,2,3-butanetricarboxylate; 2-Methylcitric acid, 3H-labeled; (2S,3S)-2-methylcitric acid; (2S,3S)-2-Methylcitrate; 2-Methylcitric acid; Methylcitric acid; 2-Methylcitrate; 2-Methylcitric Acid



数据库引用编号

20 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

2 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(2)

PharmGKB(0)

21 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

  • Jiaqi Sun, Jun Ding, Qingsong Shen, Xiyang Wang, Min Wang, Yongping Huang, Xuechun Zhang, Huan Zhu, Feng Zhang, Dongde Wu, Min Peng, Zhonglin Zhang, Yufeng Yuan, Wenhua Li, Zhi-Gang She, Xiao-Jing Zhang, Hongliang Li, Peng Zhang, Zan Huang. Decreased propionyl-CoA metabolism facilitates metabolic reprogramming and promotes hepatocellular carcinoma. Journal of hepatology. 2023 Mar; 78(3):627-642. doi: 10.1016/j.jhep.2022.11.017. [PMID: 36462680]
  • Michelle R Denburg, Yunwen Xu, Alison G Abraham, Josef Coresh, Jingsha Chen, Morgan E Grams, Harold I Feldman, Paul L Kimmel, Casey M Rebholz, Eugene P Rhee, Ramachandran S Vasan, Bradley A Warady, Susan L Furth. Metabolite Biomarkers of CKD Progression in Children. Clinical journal of the American Society of Nephrology : CJASN. 2021 08; 16(8):1178-1189. doi: 10.2215/cjn.00220121. [PMID: 34362785]
  • Evelina Maines, Giulio Catesini, Sara Boenzi, Antonella Mosca, Manila Candusso, Luca Dello Strologo, Diego Martinelli, Arianna Maiorana, Alessandra Liguori, Giorgia Olivieri, Roberta Taurisano, Fiorella Piemonte, Cristiano Rizzo, Marco Spada, Carlo Dionisi-Vici. Plasma methylcitric acid and its correlations with other disease biomarkers: The impact in the follow up of patients with propionic and methylmalonic acidemia. Journal of inherited metabolic disease. 2020 11; 43(6):1173-1185. doi: 10.1002/jimd.12287. [PMID: 32681732]
  • Osama Y Al-Dirbashi, Charu Sharma, Nahid Al Dahouri, Anas Al Aidaros, Shamma Al-Muhairi, Rami Beiram, Salah Gariballa, Juma Al Kaabi. Role of Functional Biomarkers to Identify Early Vitamin B12 Deficiency in Patients with Sleeve Gastrectomy: A Cross-Sectional Study. Medicina (Kaunas, Lithuania). 2020 Mar; 56(3):. doi: 10.3390/medicina56030142. [PMID: 32245061]
  • Joanne F Dorgan, Seungyoun Jung, Cher M Dallal, Min Zhan, Christina A Stennett, Yuji Zhang, Richard L Eckert, Linda G Snetselaar, Linda Van Horn. Alcohol consumption and serum metabolite concentrations in young women. Cancer causes & control : CCC. 2020 Feb; 31(2):113-126. doi: 10.1007/s10552-019-01256-1. [PMID: 31828464]
  • Agnese Serafini, Lendl Tan, Stuart Horswell, Steven Howell, Daniel J Greenwood, Deborah M Hunt, Minh-Duy Phan, Mark Schembri, Mercedes Monteleone, Christine R Montague, Warwick Britton, Acely Garza-Garcia, Ambrosius P Snijders, Brian VanderVen, Maximiliano G Gutierrez, Nicholas P West, Luiz Pedro S de Carvalho. Mycobacterium tuberculosis requires glyoxylate shunt and reverse methylcitrate cycle for lactate and pyruvate metabolism. Molecular microbiology. 2019 10; 112(4):1284-1307. doi: 10.1111/mmi.14362. [PMID: 31389636]
  • Nahid Al Dhahouri, Claus-Dieter Langhans, Zalikha Al Hammadi, Jürgen G Okun, Georg F Hoffmann, Fatma Al-Jasmi, Osama Y Al-Dirbashi. Quantification of methylcitrate in dried urine spots by liquid chromatography tandem mass spectrometry for the diagnosis of propionic and methylmalonic acidemias. Clinica chimica acta; international journal of clinical chemistry. 2018 Dec; 487(?):41-45. doi: 10.1016/j.cca.2018.09.017. [PMID: 30217751]
  • Hafsa Majid, Lena Jafri, Aysha Habib Khan, Zeba Zulfiqar Ali, Azeema Jamil, Nasir Yusufzai, Midhat Fatimah, Bushra Afroze. Diagnostic dilemma of patients with methylmalonic aciduria: Experience from a tertiary care centre in Pakistan. JPMA. The Journal of the Pakistan Medical Association. 2018 Apr; 68(4):510-514. doi: NULL. [PMID: 29808036]
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  • Gary E Blank, Mohamed A Virji. Development and implementation of an electronic interface for complex clinical laboratory instruments without a vendor-provided data transfer interface. Journal of pathology informatics. 2011 Jan; 2(?):14. doi: 10.4103/2153-3539.77176. [PMID: 21383937]
  • Marta Daniotti, Giancarlo la Marca, Patrizio Fiorini, Luca Filippi. New developments in the treatment of hyperammonemia: emerging use of carglumic acid. International journal of general medicine. 2011 Jan; 4(?):21-8. doi: 10.2147/ijgm.s10490. [PMID: 21403788]
  • Sally Stabler, Tatsuki Koyama, Zhiguo Zhao, Magaly Martinez-Ferrer, Robert H Allen, Zigmund Luka, Lioudmila V Loukachevitch, Peter E Clark, Conrad Wagner, Neil A Bhowmick. Serum methionine metabolites are risk factors for metastatic prostate cancer progression. PloS one. 2011; 6(8):e22486. doi: 10.1371/journal.pone.0022486. [PMID: 21853037]
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  • Ludmila V Roze, Anindya Chanda, Maris Laivenieks, Randolph M Beaudry, Katherine A Artymovich, Anna V Koptina, Deena W Awad, Dina Valeeva, Arthur D Jones, John E Linz. Volatile profiling reveals intracellular metabolic changes in Aspergillus parasiticus: veA regulates branched chain amino acid and ethanol metabolism. BMC biochemistry. 2010 Aug; 11(?):33. doi: 10.1186/1471-2091-11-33. [PMID: 20735852]
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