2-Oxoadipic acid (BioDeep_00000003399)

 

Secondary id: BioDeep_00000400102, BioDeep_00000419346

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


2-Oxohexanedionic acid

化学式: C6H8O5 (160.0371718)
中文名称: 2-氧代己二酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.06%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

2-Oxoadipic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/2-oxoadipic_acid (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000003399). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(=O)(CCCC(=O)O)C(=O)O
InChI: InChI=1S/C6H8O5/c7-4(6(10)11)2-1-3-5(8)9/h1-3H2,(H,8,9)(H,10,11)

描述信息

2-Oxoadipic acid is produced from lysine in the cytosol of cells via the saccharopine and the pipecolic acid pathways. Catabolites of hydroxylysine and tryptophan enter these pathways as 2-aminoadipic- -semialdehyde and 2-oxoadipate, respectively. In the matrix of mitochondria, 2-oxoadipate is decarboxylated to glutaryl-CoA by the 2-oxoadipate dehydrogenase complex and then converted to acetyl-CoA. 2-Oxoadipic aciduria is an in-born error of metabolism of lysine, tryptophan, and hydroxylysine, in which abnormal quantities of 2-aminoadipic acid are found in body fluids along with 2-oxoadipic acid. Patients with 2-Oxoadipic acidemias are mentally retarded with hypotonia or seizures. 2-Oxoadipic aciduria can occur in patients with Kearns-Sayre Syndrome, a progressive disorder with onset prior to 20 years of age in which multiple organ systems are affected, including progressive external ophthalmoplegia, retinopathy, and the age of onset, and these are associated classically with abnormalities in cardiac conduction, cerebellar signs, and elevated cerebrospinal fluid protein (PMID: 10655159, 16183823, 11083877). Oxoadipic acid is found to be associated with alpha-aminoadipic aciduria, which is an inborn error of metabolism.
Present in pea seedlings
KEIO_ID K009
Oxoadipic acid is a key metabolite of the essential amino acids tryptophan and lysine.

同义名列表

23 个代谢物同义名

2-Oxohexanedionic acid; 2-oxo-hexanedioic acid; alpha-Ketoadipic acid; 2-Oxohexanedioic acid; alpha-Oxoadipic acid; 2-oxo-Hexanedioate; α-Ketoadipic acid; alpha-Ketoadipate; 2-Ketoadipic acid; 2-Oxohexanedioate; a-Ketoadipic acid; a-Oxoadipic acid; alpha-Oxoadipate; 2-Oxoadipic acid; α-Oxoadipic acid; 2-Keto-adipate; Oxoadipic acid; 2-Ketoadipate; a-Ketoadipate; a-Oxoadipate; 2-Oxoadipate; Oxoadipate; Oxoadipic acid



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

417 个相关的代谢反应过程信息。

Reactome(68)

BioCyc(0)

WikiPathways(2)

Plant Reactome(320)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(25)

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

  • Yuanyuan Hu, John E Cronan. α-proteobacteria synthesize biotin precursor pimeloyl-ACP using BioZ 3-ketoacyl-ACP synthase and lysine catabolism. Nature communications. 2020 11; 11(1):5598. doi: 10.1038/s41467-020-19251-5. [PMID: 33154364]
  • Artem V Artiukhov, Aneta Grabarska, Ewelina Gumbarewicz, Vasily A Aleshin, Thilo Kähne, Toshihiro Obata, Alexey V Kazantsev, Nikolay V Lukashev, Andrzej Stepulak, Alisdair R Fernie, Victoria I Bunik. Synthetic analogues of 2-oxo acids discriminate metabolic contribution of the 2-oxoglutarate and 2-oxoadipate dehydrogenases in mammalian cells and tissues. Scientific reports. 2020 02; 10(1):1886. doi: 10.1038/s41598-020-58701-4. [PMID: 32024885]
  • Veronika Boczonadi, Martin S King, Anthony C Smith, Monika Olahova, Boglarka Bansagi, Andreas Roos, Filmon Eyassu, Christoph Borchers, Venkateswaran Ramesh, Hanns Lochmüller, Tuomo Polvikoski, Roger G Whittaker, Angela Pyle, Helen Griffin, Robert W Taylor, Patrick F Chinnery, Alan J Robinson, Edmund R S Kunji, Rita Horvath. Mitochondrial oxodicarboxylate carrier deficiency is associated with mitochondrial DNA depletion and spinal muscular atrophy-like disease. Genetics in medicine : official journal of the American College of Medical Genetics. 2018 10; 20(10):1224-1235. doi: 10.1038/gim.2017.251. [PMID: 29517768]
  • Janaína Camacho da Silva, Alexandre Umpierrez Amaral, Cristiane Cecatto, Alessandro Wajner, Kálita Dos Santos Godoy, Rafael Teixeira Ribeiro, Aline de Mello Gonçalves, Ângela Zanatta, Mateus Struecker da Rosa, Samanta Oliveira Loureiro, Carmen Regla Vargas, Guilhian Leipnitz, Diogo Onofre Gomes de Souza, Moacir Wajner. α-Ketoadipic Acid and α-Aminoadipic Acid Cause Disturbance of Glutamatergic Neurotransmission and Induction of Oxidative Stress In Vitro in Brain of Adolescent Rats. Neurotoxicity research. 2017 Aug; 32(2):276-290. doi: 10.1007/s12640-017-9735-8. [PMID: 28429309]
  • Katsumi Shibata, Chifumi Nakata, Tsutomu Fukuwatari. High-performance liquid chromatographic method for profiling 2-oxo acids in urine and its application in evaluating vitamin status in rats. Bioscience, biotechnology, and biochemistry. 2016; 80(2):304-12. doi: 10.1080/09168451.2015.1083395. [PMID: 26745680]
  • Jacob Hagen, Heleen te Brinke, Ronald J A Wanders, Alida C Knegt, Esmee Oussoren, A Jeannette M Hoogeboom, George J G Ruijter, Daniel Becker, Karl Otfried Schwab, Ingo Franke, Marinus Duran, Hans R Waterham, Jörn Oliver Sass, Sander M Houten. Genetic basis of alpha-aminoadipic and alpha-ketoadipic aciduria. Journal of inherited metabolic disease. 2015 Sep; 38(5):873-9. doi: 10.1007/s10545-015-9841-9. [PMID: 25860818]
  • Katsumi Shibata, Kasumi Inomoto, Chifumi Nakata, Tsutomu Fukuwatari. Pantothenic acid deficiency may increase the urinary excretion of 2-oxo acids and nicotinamide catabolites in rats. Journal of nutritional science and vitaminology. 2013; 59(6):509-15. doi: 10.3177/jnsv.59.509. [PMID: 24477247]
  • Katharina Danhauser, Sven W Sauer, Tobias B Haack, Thomas Wieland, Christian Staufner, Elisabeth Graf, Johannes Zschocke, Tim M Strom, Thorsten Traub, Jürgen G Okun, Thomas Meitinger, Georg F Hoffmann, Holger Prokisch, Stefan Kölker. DHTKD1 mutations cause 2-aminoadipic and 2-oxoadipic aciduria. American journal of human genetics. 2012 Dec; 91(6):1082-7. doi: 10.1016/j.ajhg.2012.10.006. [PMID: 23141293]
  • Ilka Haferkamp, Stephan Schmitz-Esser. The plant mitochondrial carrier family: functional and evolutionary aspects. Frontiers in plant science. 2012; 3(?):2. doi: 10.3389/fpls.2012.00002. [PMID: 22639632]
  • Peng Jiang, Weixing Dai, Shikai Yan, Zhongliang Chen, Ruilin Xu, Jianmi Ding, Li Xiang, Shuping Wang, Runhui Liu, Weidong Zhang. Biomarkers in the early period of acute myocardial infarction in rat serum and protective effects of Shexiang Baoxin Pill using a metabolomic method. Journal of ethnopharmacology. 2011 Nov; 138(2):530-6. doi: 10.1016/j.jep.2011.09.049. [PMID: 22001859]
  • 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]
  • Desmond B S Pink, Stephanie K Gatrell, Rajavel Elango, Joan Turchinsky, Aaron S Kiess, Kenneth P Blemings, Walter T Dixon, Ronald O Ball. Lysine α-ketoglutarate reductase, but not saccharopine dehydrogenase, is subject to substrate inhibition in pig liver. Nutrition research (New York, N.Y.). 2011 Jul; 31(7):544-54. doi: 10.1016/j.nutres.2011.06.001. [PMID: 21840471]
  • Katsumi Shibata, Miki Yasui, Mitsue Sano, Tsutomu Fukuwatari. Fluorometric determination of 2-oxoadipic acid, a common metabolite of tryptophan and lysine, by high-performance liquid chromatography with pre-chemical derivatization. Bioscience, biotechnology, and biochemistry. 2011; 75(1):185-7. doi: 10.1271/bbb.100723. [PMID: 21228461]
  • Nicolas L Taylor, Katharine A Howell, Joshua L Heazlewood, Tzu Yien W Tan, Reena Narsai, Shaobai Huang, James Whelan, A Harvey Millar. Analysis of the rice mitochondrial carrier family reveals anaerobic accumulation of a basic amino acid carrier involved in arginine metabolism during seed germination. Plant physiology. 2010 Oct; 154(2):691-704. doi: 10.1104/pp.110.162214. [PMID: 20720170]
  • 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]
  • Masashi Niimi, Lian Tao, Shi-Hua Lin, Jun Yin, Xiaoyun Wu, Hiroyuki Fukui, Junichi Kambayashi, Jianping Ye, Bing Sun. Involvement of an alternatively spliced mitochondrial oxodicarboxylate carrier in adipogenesis in 3T3-L1 cells. Journal of biomedical science. 2009 Oct; 16(?):92. doi: 10.1186/1423-0127-16-92. [PMID: 19825180]
  • Tunahan Cakir, Selma Alsan, Hale Saybaşili, Ata Akin, Kutlu O Ulgen. Reconstruction and flux analysis of coupling between metabolic pathways of astrocytes and neurons: application to cerebral hypoxia. Theoretical biology & medical modelling. 2007 Dec; 4(?):48. doi: 10.1186/1742-4682-4-48. [PMID: 18070347]
  • Antoaneta B Kroumova, George J Wagner. Different elongation pathways in the biosynthesis of acyl groups of trichome exudate sugar esters from various solanaceous plants. Planta. 2003 Apr; 216(6):1013-21. doi: 10.1007/s00425-002-0954-7. [PMID: 12687369]
  • J S Lee, H R Yoon, C J Coe. A Korean girl with alpha-aminoadipic and alpha-ketoadipic aciduria accompanied with elevation of 2-hydroxyglutarate and glutarate. Journal of inherited metabolic disease. 2001 Aug; 24(4):509-10. doi: 10.1023/a:1010589815638. [PMID: 11596655]
  • X Fu, M Kimura, M Iga, S Yamaguchi. Gas chromatographic-mass spectrometric screening for organic acidemias using dried urine filter paper: determination of alpha-ketoacids. Journal of chromatography. B, Biomedical sciences and applications. 2001 Jul; 758(1):87-94. doi: 10.1016/s0378-4347(01)00101-3. [PMID: 11482739]
  • B A Barshop, W L Nyhan, R K Naviaux, K A McGowan, M Friedlander, R H Haas. Kearns-Sayre syndrome presenting as 2-oxoadipic aciduria. Molecular genetics and metabolism. 2000 Jan; 69(1):64-8. doi: 10.1006/mgme.1999.2946. [PMID: 10655159]
  • A C Sewell, J Herwig, H Böhles, N G Abeling, A H van Gennip. Normal kynurenine metabolism in 2-oxoadipic aciduria. Journal of inherited metabolic disease. 1999 Dec; 22(8):949-50. doi: 10.1023/a:1005672314435. [PMID: 10604155]
  • D Darmaun, D D'Amore, M W Haymond. Determination of glutamine and alpha-ketoglutarate concentration and specific activity in plasma using high-performance liquid chromatography. Journal of chromatography. 1993 Oct; 620(1):33-8. doi: 10.1016/0378-4347(93)80048-9. [PMID: 8106589]
  • T Takechi, T Okada, H Wakiguchi, H Morita, T Kurashige, K Sugahara, H Kodama. Identification of N-acetyl-alpha-aminoadipic acid in the urine of a patient with alpha-aminoadipic and alpha-ketoadipic aciduria. Journal of inherited metabolic disease. 1993; 16(1):119-26. doi: 10.1007/bf00711325. [PMID: 8487492]
  • C Jakobs, A J de Grauw. A fatal case of 2-keto-, 2-hydroxy- and 2-aminoadipic aciduria: relation of organic aciduria to phenotype?. Journal of inherited metabolic disease. 1992; 15(2):279-80. doi: 10.1007/bf01799643. [PMID: 1527995]
  • C Vianey-Liaud, P Divry, J Cotte, G Teyssier. alpha-Aminoadipic and alpha-ketoadipic aciduria: detection of a new case by a screening program using two-dimensional thin layer chromatography of amino acids. Journal of inherited metabolic disease. 1985; 8 Suppl 2(?):133-4. doi: 10.1007/bf01811495. [PMID: 3930865]
  • D G Hine, K Tanaka. Capillary gas chromatographic/mass spectrometric analysis of abnormal metabolites in hypoglycin-treated rat urine. Biomedical mass spectrometry. 1984 Jul; 11(7):332-9. doi: 10.1002/bms.1200110704. [PMID: 6478044]
  • M Duran, F A Beemer, S K Wadman, U Wendel, B Janssen. A patient with alpha-ketoadipic and alpha-aminoadipic aciduria. Journal of inherited metabolic disease. 1984; 7(2):61. doi: 10.1007/bf01805803. [PMID: 6434826]