Oxoglutaric acid (BioDeep_00000001289)

 

Secondary id: BioDeep_00000405217, BioDeep_00000865860, BioDeep_00001867823

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


2-oxopentanedioic acid

化学式: C5H6O5 (146.0215226)
中文名称: α-酮戊二酸钠盐, 2-酮戊二酸, alpha-酮戊二酸, α-酮戊二酸, 2-氧戊二酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.02%

Reviewed

Last reviewed on 2024-07-16.

Cite this Page

Oxoglutaric acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/oxoglutaric_acid (retrieved 2024-11-24) (BioDeep RN: BioDeep_00000001289). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(=O)(CCC(=O)O)C(=O)O
InChI: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)

描述信息

Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207). Oxoglutaric acid has been found to be a metabolite produced by Corynebacterium and yeast (PMID: 27872963) (YMDB).
[Spectral] 2-Oxoglutarate (exact mass = 146.02152) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions.
[Spectral] 2-Oxoglutarate (exact mass = 146.02152) and (S)-Malate (exact mass = 134.02152) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions.
Flavouring ingredient

同义名列表

37 个代谢物同义名

alpha-Ketoglutaric acid disodium salt; 2-oxo-1,5-Pentanedioic acid; alpha-Oxopentanedioic acid; alpha-Keto-glutaric acid; 2-Ketoglutaric Acid-13C1; alpha-Ketoglutaric acid; 2-oxo-1,5-Pentanedioate; alpha Ketoglutaric acid; Α-oxopentanedioic acid; alpha-Oxoglutaric acid; 2-Oxopentanedioic acid; Α-keto-glutaric acid; 2-ketoglutaric acid; Α-ketoglutaric acid; alpha-Ketoglutarate; alpha Ketoglutarate; 2 Ketoglutaric acid; a-Ketoglutaric acid; Α-oxoglutaric acid; 2-Oxoglutaric acid; alpha-Oxoglutarate; 2-Oxopentanedioate; 2 Oxoglutaric acid; alpha Oxoglutarate; Ketoglutaric acid; Oxoglutaric acid; 2-Ketoglutarate; a-Ketoglutarate; 2 Ketoglutarate; Α-ketoglutarate; 2-Oxoglutarate; 2 Oxoglutarate; Oxogluric acid; Oxoglutarate; α-Ketoglutaric acid; 2-Oxoglutaric acid; 2-Oxoglutarate



数据库引用编号

38 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(20)

PlantCyc(0)

代谢反应

2212 个相关的代谢反应过程信息。

Reactome(146)

BioCyc(49)

WikiPathways(6)

Plant Reactome(1474)

INOH(34)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(503)

PharmGKB(0)

76 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

  • Tingting Lv, Xiude Fan, Chang He, Suwei Zhu, Xiaofeng Xiong, Wei Yan, Mei Liu, Hongwei Xu, Ruihua Shi, Qin He. SLC7A11-ROS/αKG-AMPK axis regulates liver inflammation through mitophagy and impairs liver fibrosis and NASH progression. Redox biology. 2024 Jun; 72(?):103159. doi: 10.1016/j.redox.2024.103159. [PMID: 38642501]
  • Kristina Žuna, Tatyana Tyschuk, Taraneh Beikbaghban, Felix Sternberg, Jürgen Kreiter, Elena E Pohl. The 2-oxoglutarate/malate carrier extends the family of mitochondrial carriers capable of fatty acid and 2,4-dinitrophenol-activated proton transport. Acta physiologica (Oxford, England). 2024 Jun; 240(6):e14143. doi: 10.1111/apha.14143. [PMID: 38577966]
  • Qiming Tang, Yuhui Huang, Xiaoxiang Ni, Ming-Ju Amy Lyu, Genyun Chen, Rowan Sage, Xin-Guang Zhu. Increased α-ketoglutarate links the C3-C4 intermediate state to C4 photosynthesis in the genus Flaveria. Plant physiology. 2024 Apr; 195(1):291-305. doi: 10.1093/plphys/kiae077. [PMID: 38377473]
  • Zhao Cui, Caifeng Li, Wei Liu, Mo Sun, Shiwen Deng, Junxian Cao, Hongjun Yang, Peng Chen. Scutellarin activates IDH1 to exert antitumor effects in hepatocellular carcinoma progression. Cell death & disease. 2024 Apr; 15(4):267. doi: 10.1038/s41419-024-06625-6. [PMID: 38622131]
  • Ying Zhang, Chun-Yan Sang, Xing-Rong Wang, Cheng-Bo Wang, Xian-Hua Meng, Wei-Feng Wang, Jun-Li Yang. Rapid evaluation of PHD2 inhibitory activity of natural products based on capillary electrophoresis online stacking strategy. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2024 Apr; 1236(?):124064. doi: 10.1016/j.jchromb.2024.124064. [PMID: 38430605]
  • Qing-Hua Qian, Ya-Ping Song, Yu Zhang, Hao Xue, Wei-Wei Zhang, Yapeng Han, Yán Wāng, De-Xiang Xu. Gestational α-ketoglutarate supplementation ameliorates arsenic-induced hepatic lipid deposition via epigenetic reprogramming of β-oxidation process in female offspring. Environment international. 2024 Mar; 185(?):108488. doi: 10.1016/j.envint.2024.108488. [PMID: 38359550]
  • Hao Yu, Daojing Gan, Zhen Luo, Qilin Yang, Dongqi An, Hao Zhang, Yingchun Hu, Zhuang Ma, Qingchun Zeng, Dingli Xu, Hao Ren. α-Ketoglutarate improves cardiac insufficiency through NAD+-SIRT1 signaling-mediated mitophagy and ferroptosis in pressure overload-induced mice. Molecular medicine (Cambridge, Mass.). 2024 Jan; 30(1):15. doi: 10.1186/s10020-024-00783-1. [PMID: 38254035]
  • San Kim, Se Hyeon Jang, Min Jeong Kim, Jeong Jae Lee, Kyung-Min Kim, Young Hoon Kim, Ju-Hoon Lee, Sung Keun Jung. Hybrid nutraceutical of 2-ketoglutaric acid in improving inflammatory bowel disease: Role of prebiotics and TAK1 inhibitor. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2024 Jan; 171(?):116126. doi: 10.1016/j.biopha.2024.116126. [PMID: 38219386]
  • Zhen-Ye Luo, Yin-Xia Hu, Chuan-Wei Qiu, Wei-Cong Chen, Li Li, Fei-Long Chen, Chang-Shun Liu. Coptidis Rhizoma processed with Evodia Rutaecarpa improves the effect on ulcerative colitis by increasing intestinal energy metabolites alpha-ketoglutarate and Lactobacillus reuteri. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Dec; 121(?):155115. doi: 10.1016/j.phymed.2023.155115. [PMID: 37801896]
  • Theo Lange, Nadiem Atiq, Maria João Pimenta Lange. GAS2 encodes a 2-oxoglutarate dependent dioxygenase involved in ABA catabolism. Nature communications. 2023 Nov; 14(1):7602. doi: 10.1038/s41467-023-43187-1. [PMID: 37990018]
  • Oleh Demianchuk, Myroslava Vatashchuk, Dmytro Gospodaryov, Viktoria Hurza, Marian Ivanochko, Vitalii Derkachov, Vladyslav Berezovkyi, Oleh Lushchak, Kenneth B Storey, Maria Bayliak, Volodymyr I Lushchak. High-fat high-fructose diet and alpha-ketoglutarate affect mouse behavior that is accompanied by changes in oxidative stress response and energy metabolism in the cerebral cortex. Biochimica et biophysica acta. General subjects. 2023 Nov; ?(?):130521. doi: 10.1016/j.bbagen.2023.130521. [PMID: 37967727]
  • Stephen M G Duff, Meiying Zhang, Fred Zinnel, Timothy Rydel, Christina M Taylor, Danqi Chen, Gregory Tilton, Patricia Mamanella, David Duda, Yanfei Wang, Bosong Xiang, Balasulojini Karunanandaa, Rita Varagona, Jaishree Chittoor, Qungang Qi, Erin Hall, Graeme Garvey, Jiamin Zeng, Jun Zhang, Xin Li, Tommi White, Agoston Jerga, Jeff Haas. Structural and functional characterization of triketone dioxygenase from Oryza Sativa. Biochimica et biophysica acta. General subjects. 2023 Nov; ?(?):130504. doi: 10.1016/j.bbagen.2023.130504. [PMID: 37967728]
  • Melanie N Hurst, Connor J Beebout, Alexis Hollingsworth, Kirsten R Guckes, Alexandria Purcell, Tomas A Bermudez, Diamond Williams, Seth A Reasoner, M Stephen Trent, Maria Hadjifrangiskou. The QseB response regulator imparts tolerance to positively charged antibiotics by controlling metabolism and minor changes to LPS. mSphere. 2023 10; 8(5):e0005923. doi: 10.1128/msphere.00059-23. [PMID: 37676915]
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  • Gang Li, Ziwen Gong, Nawaraj Dulal, Margarita Marroquin-Guzman, Raquel O Rocha, Michael Richter, Richard A Wilson. A protein kinase coordinates cycles of autophagy and glutaminolysis in invasive hyphae of the fungus Magnaporthe oryzae within rice cells. Nature communications. 2023 07; 14(1):4146. doi: 10.1038/s41467-023-39880-w. [PMID: 37438395]
  • Akiyoshi Yoda, Xiaonan Xie, Kaori Yoneyama, Kenji Miura, Christopher S P McErlean, Takahito Nomura. A Stereoselective Strigolactone Biosynthesis Catalyzed by a 2-Oxoglutarate-Dependent Dioxygenase in Sorghum. Plant & cell physiology. 2023 Jun; ?(?):. doi: 10.1093/pcp/pcad060. [PMID: 37307421]
  • Zhijia Gai, Maoming Zhang, Pengfei Zhang, Jingtao Zhang, Jingqi Liu, Lijun Cai, Xu Yang, Na Zhang, Zhengnan Yan, Lei Liu, Guozhong Feng. 2-Oxoglutarate contributes to the effect of foliar nitrogen on enhancing drought tolerance during flowering and grain yield of soybean. Scientific reports. 2023 May; 13(1):7274. doi: 10.1038/s41598-023-34403-5. [PMID: 37142711]
  • Ruojing Liu, Yi Gao, Li Huang, Bing Shi, Xing Yin, Shujuan Zou. Alpha-ketoglutarate up-regulates autophagic activity in peri-implant environment and enhances dental implant osseointegration in osteoporotic mice. Journal of clinical periodontology. 2023 05; 50(5):671-683. doi: 10.1111/jcpe.13784. [PMID: 36734077]
  • Angelika Janaszkiewicz, Ágota Tóth, Quentin Faucher, Hélène Arnion, Nicolas Védrenne, Chantal Barin-Le Guellec, Pierre Marquet, Florent Di Meo. Substrate binding and lipid-mediated allostery in the human organic anion transporter 1 at the atomic-scale. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Feb; 160(?):114342. doi: 10.1016/j.biopha.2023.114342. [PMID: 36739760]
  • Athena Papadopoulou, Fabian Meyer, Rebecca M Buller. Engineering Fe(II)/α-Ketoglutarate-Dependent Halogenases and Desaturases. Biochemistry. 2023 01; 62(2):229-240. doi: 10.1021/acs.biochem.2c00115. [PMID: 35446547]
  • Hanny Chauhan, Aiana, Kashmir Singh. Genome-wide identification of 2-oxoglutarate and Fe (II)-dependent dioxygenase family genes and their expression profiling under drought and salt stress in potato. PeerJ. 2023; 11(?):e16449. doi: 10.7717/peerj.16449. [PMID: 38025721]
  • Maria M Bayliak, Myroslava V Vatashchuk, Dmytro V Gospodaryov, Viktoria V Hurza, Oleh I Demianchuk, Marian V Ivanochko, Nadia I Burdyliuk, Kenneth B Storey, Oleh Lushchak, Volodymyr I Lushchak. High fat high fructose diet induces mild oxidative stress and reorganizes intermediary metabolism in male mouse liver: Alpha-ketoglutarate effects. Biochimica et biophysica acta. General subjects. 2022 12; 1866(12):130226. doi: 10.1016/j.bbagen.2022.130226. [PMID: 35987369]
  • Haotian Liu, Yong Xie, Xia Wang, Martine I Abboud, Chao Ma, Wei Ge, Christopher J Schofield. Exploring links between 2-oxoglutarate-dependent oxygenases and Alzheimer's disease. Alzheimer's & dementia : the journal of the Alzheimer's Association. 2022 12; 18(12):2637-2668. doi: 10.1002/alz.12733. [PMID: 35852137]
  • Qing-Qi Chang, Long Chen, Ya-Fang Liao, Chun-Lu Yuan, Dan-Dan Zhang. [Mechanism of timosaponin AⅢ in regulation of metabolism against glioblastoma growth]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 Dec; 47(24):6679-6686. doi: 10.19540/j.cnki.cjcmm.20220728.401. [PMID: 36604918]
  • Shao-Liang Yang, Hai-Xia Tan, Zhen-Zhen Lai, Hai-Yan Peng, Hui-Li Yang, Qiang Fu, Hai-Yan Wang, Da-Jin Li, Ming-Qing Li. An active glutamine/α-ketoglutarate/HIF-1α axis prevents pregnancy loss by triggering decidual IGF1+GDF15+NK cell differentiation. Cellular and molecular life sciences : CMLS. 2022 Nov; 79(12):611. doi: 10.1007/s00018-022-04639-x. [PMID: 36449080]
  • Shuhan Lei, Bingru Huang. Metabolic regulation of α-Ketoglutarate associated with heat tolerance in perennial ryegrass. Plant physiology and biochemistry : PPB. 2022 Nov; 190(?):164-173. doi: 10.1016/j.plaphy.2022.09.005. [PMID: 36116225]
  • Zhi-Rong Lin, Zhen-Zhen Li, Yan-Jun Cao, Wen-Jing Yu, Jian-Tao Ye, Pei-Qing Liu. GDH promotes isoprenaline-induced cardiac hypertrophy by activating mTOR signaling via elevation of α-ketoglutarate level. Naunyn-Schmiedeberg's archives of pharmacology. 2022 11; 395(11):1373-1385. doi: 10.1007/s00210-022-02252-0. [PMID: 35904584]
  • Xuewen Zhu, Yaolei Mi, Xiangxiao Meng, Yiming Zhang, Weiqiang Chen, Xue Cao, Huihua Wan, Wei Yang, Jun Li, Sifan Wang, Zhichao Xu, Atia Tul Wahab, Shilin Chen, Wei Sun. Genome-wide identification of key enzyme-encoding genes and the catalytic roles of two 2-oxoglutarate-dependent dioxygenase involved in flavonoid biosynthesis in Cannabis sativa L. Microbial cell factories. 2022 Oct; 21(1):215. doi: 10.1186/s12934-022-01933-y. [PMID: 36243861]
  • Daniel Gonzalez Izundegui, Patricia E Miller, Ravi V Shah, Clary B Clish, Maura E Walker, Gary F Mitchell, Robert E Gerszten, Martin G Larson, Ramachandran S Vasan, Matthew Nayor. Response of circulating metabolites to an oral glucose challenge and risk of cardiovascular disease and mortality in the community. Cardiovascular diabetology. 2022 10; 21(1):213. doi: 10.1186/s12933-022-01647-w. [PMID: 36243866]
  • Yong Cai, Zhiyi Dong, Jiying Wang. Circ_0000808 promotes the development of non-small cell lung cancer by regulating glutamine metabolism via the miR-1827/SLC1A5 axis. World journal of surgical oncology. 2022 Oct; 20(1):329. doi: 10.1186/s12957-022-02777-x. [PMID: 36192755]
  • Michael H Kramer, Qiang Zhang, Robert Sprung, Ryan B Day, Petra Erdmann-Gilmore, Yang Li, Ziheng Xu, Nichole M Helton, Daniel R George, Yiling Mi, Peter Westervelt, Jacqueline E Payton, Sai M Ramakrishnan, Christopher A Miller, Daniel C Link, John F DiPersio, Matthew J Walter, R Reid Townsend, Timothy J Ley. Proteomic and phosphoproteomic landscapes of acute myeloid leukemia. Blood. 2022 09; 140(13):1533-1548. doi: 10.1182/blood.2022016033. [PMID: 35895896]
  • Sawako Suzuki, Divya Venkatesh, Hiroaki Kanda, Akitoshi Nakayama, Hiroyuki Hosokawa, Eunyoung Lee, Takashi Miki, Brent R Stockwell, Koutaro Yokote, Tomoaki Tanaka, Carol Prives. GLS2 Is a Tumor Suppressor and a Regulator of Ferroptosis in Hepatocellular Carcinoma. Cancer research. 2022 Sep; 82(18):3209-3222. doi: 10.1158/0008-5472.can-21-3914. [PMID: 35895807]
  • Zalina I Iskhakova, Darya E Zhuravleva, Christopher Heim, Marcus D Hartmann, Aleksandr V Laykov, Karl Forchhammer, Airat R Kayumov. PotN represents a novel energy-state sensing PII subfamily, occurring in firmicutes. The FEBS journal. 2022 09; 289(17):5305-5321. doi: 10.1111/febs.16431. [PMID: 35285159]
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