3-Methyl-2-oxovaleric acid (BioDeep_00000265241)

 

Secondary id: BioDeep_00000015107, BioDeep_00000229621, BioDeep_00000419349, BioDeep_00000873002

PANOMIX_OTCML-2023


代谢物信息卡片


(3S)-3-Methyl-2-oxopentanoic acid

化学式: C6H10O3 (130.062991)
中文名称: 3-甲基-2-氧代戊酸, 3-甲基-2-氧基戊酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.76%

分子结构信息

SMILES: CCC(C)C(=O)C(=O)O
InChI: InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)

描述信息

A 2-oxo monocarboxylic acid that is valeric acid carrying oxo- and methyl substituents at C-2 and C-3, respectively. An alpha-keto acid analogue and metabolite of isoleucine in man, animals and bacteria. Used as a clinical marker for maple syrup urine disease (MSUD).
3-Methyl-2-oxovaleric acid is a neurotoxin, an acidogen, and a metabotoxin, and also an abnormal metabolite that arises from the incomplete breakdown of branched-chain amino acids.

同义名列表

2 个代谢物同义名

(3S)-3-Methyl-2-oxopentanoic acid; 3-Methyl-2-oxovaleric acid



数据库引用编号

17 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)

6 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

  • Woong B Kwon, Kevin J Touchette, Aude Simongiovanni, Kostas Syriopoulos, Anna Wessels, Hans H Stein. Excess dietary leucine in diets for growing pigs reduces growth performance, biological value of protein, protein retention, and serotonin synthesis1. Journal of animal science. 2019 Oct; 97(10):4282-4292. doi: 10.1093/jas/skz259. [PMID: 31410464]
  • Katsumi Shibata. Urinary Excretion of 2-Oxo Acids Is Greater in Rats with Streptozotocin-Induced Diabetes. Journal of nutritional science and vitaminology. 2018; 64(4):292-295. doi: 10.3177/jnsv.64.292. [PMID: 30175794]
  • Kurt Lächler, Janet Imhof, Michael Reichelt, Jonathan Gershenzon, Stefan Binder. The cytosolic branched-chain aminotransferases of Arabidopsis thaliana influence methionine supply, salvage and glucosinolate metabolism. Plant molecular biology. 2015 May; 88(1-2):119-31. doi: 10.1007/s11103-015-0312-3. [PMID: 25851613]
  • Claire L Boulangé, Sandrine P Claus, Chieh J Chou, Sebastiano Collino, Ivan Montoliu, Sunil Kochhar, Elaine Holmes, Serge Rezzi, Jeremy K Nicholson, Marc E Dumas, François-Pierre J Martin. Early metabolic adaptation in C57BL/6 mice resistant to high fat diet induced weight gain involves an activation of mitochondrial oxidative pathways. Journal of proteome research. 2013 Apr; 12(4):1956-68. doi: 10.1021/pr400051s. [PMID: 23473242]
  • Jia V Li, Jasmina Saric, Yulan Wang, Jennifer Keiser, Jürg Utzinger, Elaine Holmes. Chemometric analysis of biofluids from mice experimentally infected with Schistosoma mansoni. Parasites & vectors. 2011 Sep; 4(?):179. doi: 10.1186/1756-3305-4-179. [PMID: 21929782]
  • Jia V Li, Jasmina Saric, Yulan Wang, Jürg Utzinger, Elaine Holmes, Oliver Balmer. Metabonomic investigation of single and multiple strain Trypanosoma brucei brucei infections. The American journal of tropical medicine and hygiene. 2011 Jan; 84(1):91-8. doi: 10.4269/ajtmh.2011.10-0402. [PMID: 21212208]
  • Jan-Willem de Kraker, Jonathan Gershenzon. From amino acid to glucosinolate biosynthesis: protein sequence changes in the evolution of methylthioalkylmalate synthase in Arabidopsis. The Plant cell. 2011 Jan; 23(1):38-53. doi: 10.1105/tpc.110.079269. [PMID: 21205930]
  • Junfang Wu, Wenxin Xu, Zhenping Ming, Huifen Dong, Huiru Tang, Yulan Wang. Metabolic changes reveal the development of schistosomiasis in mice. PLoS neglected tropical diseases. 2010 Aug; 4(8):. doi: 10.1371/journal.pntd.0000807. [PMID: 20824219]
  • Gregory S Maloney, Andrej Kochevenko, Denise M Tieman, Takayuki Tohge, Uri Krieger, Dani Zamir, Mark G Taylor, Alisdair R Fernie, Harry J Klee. Characterization of the branched-chain amino acid aminotransferase enzyme family in tomato. Plant physiology. 2010 Jul; 153(3):925-36. doi: 10.1104/pp.110.154922. [PMID: 20435740]
  • Susan C Connor, Michael K Hansen, Adam Corner, Randall F Smith, Terence E Ryan. Integration of metabolomics and transcriptomics data to aid biomarker discovery in type 2 diabetes. Molecular bioSystems. 2010 May; 6(5):909-21. doi: 10.1039/b914182k. [PMID: 20567778]
  • Markus Karl Wiltafsky, Michael Walter Pfaffl, Franz Xaver Roth. The effects of branched-chain amino acid interactions on growth performance, blood metabolites, enzyme kinetics and transcriptomics in weaned pigs. The British journal of nutrition. 2010 Apr; 103(7):964-76. doi: 10.1017/s0007114509992212. [PMID: 20196890]
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  • Tanja Knill, Michael Reichelt, Christian Paetz, Jonathan Gershenzon, Stefan Binder. Arabidopsis thaliana encodes a bacterial-type heterodimeric isopropylmalate isomerase involved in both Leu biosynthesis and the Met chain elongation pathway of glucosinolate formation. Plant molecular biology. 2009 Oct; 71(3):227-39. doi: 10.1007/s11103-009-9519-5. [PMID: 19597944]
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  • Carolyn M Slupsky, Andriy Cheypesh, Danny V Chao, Hao Fu, Kathryn N Rankin, Thomas J Marrie, Paige Lacy. Streptococcus pneumoniae and Staphylococcus aureus pneumonia induce distinct metabolic responses. Journal of proteome research. 2009 Jun; 8(6):3029-36. doi: 10.1021/pr900103y. [PMID: 19368345]
  • Chang Shi, Chun-Qi Wu, An-Min Cao, He-Zhang Sheng, Xian-Zhong Yan, Ming-Yang Liao. NMR-spectroscopy-based metabonomic approach to the analysis of Bay41-4109, a novel anti-HBV compound, induced hepatotoxicity in rats. Toxicology letters. 2007 Sep; 173(3):161-7. doi: 10.1016/j.toxlet.2007.07.010. [PMID: 17826925]
  • Cláudia Funchal, Francine Tramontina, André Quincozes dos Santos, Daniela Fraga de Souza, Carlos Alberto Gonçalves, Regina Pessoa-Pureur, Moacir Wajner. Effect of the branched-chain alpha-keto acids accumulating in maple syrup urine disease on S100B release from glial cells. Journal of the neurological sciences. 2007 Sep; 260(1-2):87-94. doi: 10.1016/j.jns.2007.04.011. [PMID: 17499767]
  • Alexander I Shestopalov, Bruce S Kristal. Branched chain keto-acids exert biphasic effects on alpha-ketoglutarate-stimulated respiration in intact rat liver mitochondria. Neurochemical research. 2007 Apr; 32(4-5):947-51. doi: 10.1007/s11064-007-9291-3. [PMID: 17342410]
  • André Wajner, Cristiane Bürger, Carlos Severo Dutra-Filho, Moacir Wajner, Angela Terezinha de Souza Wyse, Clóvis Milton Duval Wannmacher. Synaptic plasma membrane Na(+), K (+)-ATPase activity is significantly reduced by the alpha-keto acids accumulating in maple syrup urine disease in rat cerebral cortex. Metabolic brain disease. 2007 Mar; 22(1):77-88. doi: 10.1007/s11011-007-9046-5. [PMID: 17295076]
  • Anne-Laure Cavin, Anne-Emmanuelle Hay, Andrew Marston, Helen Stoeckli-Evans, Rosario Scopelliti, Drissa Diallo, Kurt Hostettmann. Bioactive diterpenes from the fruits of Detarium microcarpum. Journal of natural products. 2006 May; 69(5):768-73. doi: 10.1021/np058123q. [PMID: 16724838]
  • Cláudia Funchal, Patrícia Fernanda Schuck, André Quincozes Dos Santos, Maria Caroline Jacques-Silva, Carmem Gottfried, Regina Pessoa-Pureur, Moacir Wajner. Creatine and antioxidant treatment prevent the inhibition of creatine kinase activity and the morphological alterations of C6 glioma cells induced by the branched-chain alpha-keto acids accumulating in maple syrup urine disease. Cellular and molecular neurobiology. 2006 Feb; 26(1):67-79. doi: 10.1007/s10571-006-9098-9. [PMID: 16633902]
  • Cláudia Funchal, André Quincozes Dos Santos, Maria Caroline Jacques-Silva, Ariane Zamoner, Carmem Gottfried, Moacir Wajner, Regina Pessoa-Pureur. Branched-chain alpha-keto acids accumulating in maple syrup urine disease induce reorganization of phosphorylated GFAP in C6-glioma cells. Metabolic brain disease. 2005 Sep; 20(3):205-17. doi: 10.1007/s11011-005-7208-x. [PMID: 16167198]
  • Raquel Bridi, César A Braun, Giovanni K Zorzi, Clóvis M D Wannmacher, Moacir Wajner, Eduardo G Lissi, Carlos Severo Dutra-Filho. alpha-keto acids accumulating in maple syrup urine disease stimulate lipid peroxidation and reduce antioxidant defences in cerebral cortex from young rats. Metabolic brain disease. 2005 Jun; 20(2):155-67. doi: 10.1007/s11011-005-4152-8. [PMID: 15938133]
  • Cláudia Funchal, Carmem Gottfried, Lúcia Maria Vieira De Almeida, Moacir Wajner, Regina Pessoa-Pureur. Evidence that the branched-chain alpha-keto acids accumulating in maple syrup urine disease induce morphological alterations and death in cultured astrocytes from rat cerebral cortex. Glia. 2004 Nov; 48(3):230-40. doi: 10.1002/glia.20072. [PMID: 15390119]
  • Cláudia Funchal, Franciele Dall Bello Pessutto, Lúcia Maria Vieira de Almeida, Priscila de Lima Pelaez, Samanta Oliveira Loureiro, Lilian Vivian, Moacir Wajner, Regina Pessoa-Pureur. Alpha-keto-beta-methylvaleric acid increases the in vitro phosphorylation of intermediate filaments in cerebral cortex of young rats through the gabaergic system. Journal of the neurological sciences. 2004 Jan; 217(1):17-24. doi: 10.1016/j.jns.2003.08.003. [PMID: 14675604]
  • Vilson de Castro Vasques, Melissa Avila de Boer, Felipe Diligenti, Fabrício Brinco, Fabrício Mallmann, Carlos Fernando Mello, Moacir Wajner. Intrahippocampal administration of the alpha-keto acids accumulating in maple syrup urine disease provokes learning deficits in rats. Pharmacology, biochemistry, and behavior. 2004 Jan; 77(1):183-90. doi: 10.1016/j.pbb.2003.10.013. [PMID: 14724056]
  • Angela M Sgaravatti, Rafael B Rosa, Patrícia F Schuck, César A J Ribeiro, Clóvis M D Wannmacher, Angela T S Wyse, Carlos S Dutra-Filho, Moacir Wajner. Inhibition of brain energy metabolism by the alpha-keto acids accumulating in maple syrup urine disease. Biochimica et biophysica acta. 2003 Nov; 1639(3):232-8. doi: 10.1016/j.bbadis.2003.09.010. [PMID: 14636955]
  • R Pessoa-Pureur, C Funchal, P de Lima Pelaez, L Vivian, S Oliveira Loureiro, R de Freitas Miranda, M Wajner. Effect of the branched-chain alpha-ketoacids accumulating in maple syrup urine disease on the high molecular weight neurofilament subunit (NF-H) in rat cerebral cortex. Metabolic brain disease. 2002 Jun; 17(2):65-75. doi: 10.1023/a:1015459910869. [PMID: 12083338]
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  • R G Tavares, C E Santos, C I Tasca, M Wajner, D O Souza, C S Dutra-Filho. Inhibition of glutamate uptake into synaptic vesicles of rat brain by the metabolites accumulating in maple syrup urine disease. Journal of the neurological sciences. 2000 Dec; 181(1-2):44-9. doi: 10.1016/s0022-510x(00)00402-0. [PMID: 11099711]
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