FA 4:2;O3 (BioDeep_00000629381)

 

Secondary id: BioDeep_00000005364, BioDeep_00000405222, BioDeep_00001869707

PANOMIX_OTCML-2023 BioNovoGene_Lab2019


代谢物信息卡片


2-Hydroxybut-2-enedioic acid

化学式: C4H4O5 (132.00587339999998)
中文名称: 草乙酸, 草酰乙酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.17%

分子结构信息

SMILES: C(/O)(\C(=O)O)=C/C(=O)O
InChI: InChI=1S/C4H4O5/c5-2(4(8)9)1-3(6)7/h1H2,(H,6,7)(H,8,9)

描述信息

C274 - Antineoplastic Agent > C177430 - Agent Targeting Cancer Metabolism
C26170 - Protective Agent > C1509 - Neuroprotective Agent
Oxaloacetic acid (2-Oxosuccinic acid) is a metabolic intermediate involved in several ways, such as citric acid cycle, gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, and fatty acid synthesis[1][2].
Oxaloacetic acid (2-Oxosuccinic acid) is a metabolic intermediate involved in several ways, such as citric acid cycle, gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, and fatty acid synthesis[1][2].

同义名列表

9 个代谢物同义名

2-oxo-butanedioic acid; Oxaloacetic acid; oxalacetic acid; FA 4:2;O3; 2-Hydroxybut-2-enedioic acid; 2-hydroxy-2-butenedioic acid; 2-Oxosuccinic acid; Oxaloacetate; Oxalacetic acid



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(1)

BioCyc(2)

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

  • Erika Greipel, Krisztina Nagy, Eszter Csákvári, László Dér, Peter Galajda, József Kutasi. Chemotactic Interactions of Scenedesmus sp. and Azospirillum brasilense Investigated by Microfluidic Methods. Microbial ecology. 2024 Mar; 87(1):52. doi: 10.1007/s00248-024-02366-3. [PMID: 38498218]
  • Cong Yin, Rui Qin, Zewei Ma, Fan Li, Jiao Liu, Hong Liu, Gang Shu, Hairong Xiong, Qingyan Jiang. Oxaloacetic acid induces muscle energy substrate depletion and fatigue by JNK-mediated mitochondrial uncoupling. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2024 02; 38(2):e23373. doi: 10.1096/fj.202301796r. [PMID: 38217376]
  • Anthony J Zmuda, Xiaojun Kang, Katie B Wissbroecker, Katrina Freund Saxhaug, Kyle C Costa, Adrian D Hegeman, Thomas D Niehaus. A universal metabolite repair enzyme removes a strong inhibitor of the TCA cycle. Nature communications. 2024 Jan; 15(1):846. doi: 10.1038/s41467-024-45134-0. [PMID: 38287013]
  • Maki Nishii, Shoki Ito, Takashi Osanai. Citrate synthase from Cyanidioschyzon merolae exhibits high oxaloacetate and acetyl-CoA catalytic efficiency. Plant molecular biology. 2023 Mar; ?(?):. doi: 10.1007/s11103-023-01335-7. [PMID: 36884198]
  • Alan Cash, David Lyons Kaufman. Oxaloacetate Treatment For Mental And Physical Fatigue In Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS) and Long-COVID fatigue patients: a non-randomized controlled clinical trial. Journal of translational medicine. 2022 06; 20(1):295. doi: 10.1186/s12967-022-03488-3. [PMID: 35764955]
  • Kusum Rana, Junhu Yuan, Hongmei Liao, Surinder S Banga, Rahul Kumar, Wei Qian, Yijuan Ding. Host-induced gene silencing reveals the role of Sclerotinia sclerotiorum oxaloacetate acetylhydrolase gene in fungal oxalic acid accumulation and virulence. Microbiological research. 2022 May; 258(?):126981. doi: 10.1016/j.micres.2022.126981. [PMID: 35183041]
  • Arthur J L Cooper, Thambi Dorai, John T Pinto, Travis T Denton. The metabolic importance of the overlooked asparaginase II pathway. Analytical biochemistry. 2022 05; 644(?):114084. doi: 10.1016/j.ab.2020.114084. [PMID: 33347861]
  • Yona Goldshmit, Rita Perelroizen, Alex Yakovchuk, Evgeni Banyas, Lior Mayo, Sari David, Amit Benbenishty, Pablo Blinder, Moshe Shalom, Angela Ruban. Blood glutamate scavengers increase pro-apoptotic signaling and reduce metastatic melanoma growth in-vivo. Scientific reports. 2021 07; 11(1):14644. doi: 10.1038/s41598-021-94183-8. [PMID: 34282238]
  • Shoki Ito, Takumi Hakamada, Tatsumi Ogino, Takashi Osanai. Reconstitution of oxaloacetate metabolism in the tricarboxylic acid cycle in Synechocystis sp. PCC 6803: discovery of important factors that directly affect the conversion of oxaloacetate. The Plant journal : for cell and molecular biology. 2021 03; 105(6):1449-1458. doi: 10.1111/tpj.15120. [PMID: 33280178]
  • Eric D Vidoni, In-Young Choi, Phil Lee, Gregory Reed, Na Zhang, Joseph Pleen, Jonathan D Mahnken, Jonathan Clutton, Annette Becker, Erica Sherry, Rebecca Bothwell, Heidi Anderson, Robert A Harris, William Brooks, Heather M Wilkins, Lisa Mosconi, Jeffrey M Burns, Russell H Swerdlow. Safety and target engagement profile of two oxaloacetate doses in Alzheimer's patients. Alzheimer's & dementia : the journal of the Alzheimer's Association. 2021 01; 17(1):7-17. doi: 10.1002/alz.12156. [PMID: 32715609]
  • Philippe Icard, Zherui Wu, Ludovic Fournel, Antoine Coquerel, Hubert Lincet, Marco Alifano. ATP citrate lyase: A central metabolic enzyme in cancer. Cancer letters. 2020 02; 471(?):125-134. doi: 10.1016/j.canlet.2019.12.010. [PMID: 31830561]
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  • Bruno E Rojas, Matías D Hartman, Carlos M Figueroa, Laura Leaden, Florencio E Podestá, Alberto A Iglesias. Biochemical characterization of phosphoenolpyruvate carboxykinases from Arabidopsis thaliana. The Biochemical journal. 2019 10; 476(20):2939-2952. doi: 10.1042/bcj20190523. [PMID: 31548269]
  • Yana Shaulov, Chikako Shimokawa, Meirav Trebicz-Geffen, Shruti Nagaraja, Karen Methling, Michael Lalk, Lea Weiss-Cerem, Ayelet T Lamm, Hajime Hisaeda, Serge Ankri. Escherichia coli mediated resistance of Entamoeba histolytica to oxidative stress is triggered by oxaloacetate. PLoS pathogens. 2018 10; 14(10):e1007295. doi: 10.1371/journal.ppat.1007295. [PMID: 30308066]
  • Cun Wang, Jingbo Zhang, Juyou Wu, Dennis E Brodsky, Julian I Schroeder. Cytosolic malate and oxaloacetate activate S-type anion channels in Arabidopsis guard cells. The New phytologist. 2018 10; 220(1):178-186. doi: 10.1111/nph.15292. [PMID: 29971803]
  • Juan P Zubimendi, Andrea Martinatto, Maria P Valacco, Silvia Moreno, Carlos S Andreo, María F Drincovich, Marcos A Tronconi. The complex allosteric and redox regulation of the fumarate hydratase and malate dehydratase reactions of Arabidopsis thaliana Fumarase 1 and 2 gives clues for understanding the massive accumulation of fumarate. The FEBS journal. 2018 06; 285(12):2205-2224. doi: 10.1111/febs.14483. [PMID: 29688630]
  • Ye Kuang, Xiaoyun Han, Mu Xu, Yue Wang, Yuxiang Zhao, Qing Yang. Oxaloacetate Ameliorates Chemical Liver Injury via Oxidative Stress Reduction and Enhancement of Bioenergetic Fluxes. International journal of molecular sciences. 2018 May; 19(6):. doi: 10.3390/ijms19061626. [PMID: 29857490]
  • Jennifer Selinski, Andreas Hartmann, Gabriele Deckers-Hebestreit, David A Day, James Whelan, Renate Scheibe. Alternative Oxidase Isoforms Are Differentially Activated by Tricarboxylic Acid Cycle Intermediates. Plant physiology. 2018 02; 176(2):1423-1432. doi: 10.1104/pp.17.01331. [PMID: 29208641]
  • Jaime Abrego, Venugopal Gunda, Enza Vernucci, Surendra K Shukla, Ryan J King, Aneesha Dasgupta, Gennifer Goode, Divya Murthy, Fang Yu, Pankaj K Singh. GOT1-mediated anaplerotic glutamine metabolism regulates chronic acidosis stress in pancreatic cancer cells. Cancer letters. 2017 08; 400(?):37-46. doi: 10.1016/j.canlet.2017.04.029. [PMID: 28455244]
  • Qingpeng Liu, Gang Zhao, Changwei Zhou, Martin R Farlow, Yansheng Du, Guangxu Xu, Huiying Gu. Oxaloacetate and adipose stromal cells-conditional medium synergistically protected potassium/serum deprivation-induced neuronal apoptosis. Brain research bulletin. 2017 01; 128(?):7-12. doi: 10.1016/j.brainresbull.2016.11.002. [PMID: 27816553]
  • Nanette R Boyle, Neelanjan Sengupta, John A Morgan. Metabolic flux analysis of heterotrophic growth in Chlamydomonas reinhardtii. PloS one. 2017; 12(5):e0177292. doi: 10.1371/journal.pone.0177292. [PMID: 28542252]
  • 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]
  • Howbeer Muhamadali, Yun Xu, David I Ellis, J William Allwood, Nicholas J W Rattray, Elon Correa, Haitham Alrabiah, Jonathan R Lloyd, Royston Goodacre. Metabolic Profiling of Geobacter sulfurreducens during Industrial Bioprocess Scale-Up. Applied and environmental microbiology. 2015 May; 81(10):3288-98. doi: 10.1128/aem.00294-15. [PMID: 25746987]
  • Christopher G Poggi, Kristin M Slade. Macromolecular crowding and the steady-state kinetics of malate dehydrogenase. Biochemistry. 2015 Jan; 54(2):260-7. doi: 10.1021/bi5011255. [PMID: 25478785]
  • Heather M Wilkins, Janna L Harris, Steven M Carl, Lezi E, Jianghua Lu, J Eva Selfridge, Nairita Roy, Lewis Hutfles, Scott Koppel, Jill Morris, Jeffrey M Burns, Mary L Michaelis, Elias K Michaelis, William M Brooks, Russell H Swerdlow. Oxaloacetate activates brain mitochondrial biogenesis, enhances the insulin pathway, reduces inflammation and stimulates neurogenesis. Human molecular genetics. 2014 Dec; 23(24):6528-41. doi: 10.1093/hmg/ddu371. [PMID: 25027327]
  • Abhaypratap Vishwakarma, Leena Bashyam, Balasubramanian Senthilkumaran, Renate Scheibe, Kollipara Padmasree. Physiological role of AOX1a in photosynthesis and maintenance of cellular redox homeostasis under high light in Arabidopsis thaliana. Plant physiology and biochemistry : PPB. 2014 Aug; 81(?):44-53. doi: 10.1016/j.plaphy.2014.01.019. [PMID: 24560882]
  • Angelo Vozza, Giovanni Parisi, Francesco De Leonardis, Francesco M Lasorsa, Alessandra Castegna, Daniela Amorese, Raffaele Marmo, Valeria M Calcagnile, Luigi Palmieri, Daniel Ricquier, Eleonora Paradies, Pasquale Scarcia, Ferdinando Palmieri, Frédéric Bouillaud, Giuseppe Fiermonte. UCP2 transports C4 metabolites out of mitochondria, regulating glucose and glutamine oxidation. Proceedings of the National Academy of Sciences of the United States of America. 2014 Jan; 111(3):960-5. doi: 10.1073/pnas.1317400111. [PMID: 24395786]
  • M Pérez-Mato, P Ramos-Cabrer, T Sobrino, M Blanco, A Ruban, D Mirelman, P Menendez, J Castillo, F Campos. Human recombinant glutamate oxaloacetate transaminase 1 (GOT1) supplemented with oxaloacetate induces a protective effect after cerebral ischemia. Cell death & disease. 2014 Jan; 5(?):e992. doi: 10.1038/cddis.2013.507. [PMID: 24407245]
  • Jian-jun Chen, Hua Huang, Li-bo Zhao, De-zhi Zhou, Yong-tao Yang, Peng Zheng, De-yu Yang, Peng He, Jing-jing Zhou, Liang Fang, Peng Xie. Sex-specific urinary biomarkers for diagnosing bipolar disorder. PloS one. 2014; 9(12):e115221. doi: 10.1371/journal.pone.0115221. [PMID: 25531985]
  • Anja Bienholz, Ahmad Al-Taweel, Nancy F Roeser, Andreas Kribben, Thorsten Feldkamp, Joel M Weinberg. Substrate modulation of fatty acid effects on energization and respiration of kidney proximal tubules during hypoxia/reoxygenation. PloS one. 2014; 9(4):e94584. doi: 10.1371/journal.pone.0094584. [PMID: 24728405]
  • Sirisha Ghanta, Ruth E Grossmann, Charles Brenner. Mitochondrial protein acetylation as a cell-intrinsic, evolutionary driver of fat storage: chemical and metabolic logic of acetyl-lysine modifications. Critical reviews in biochemistry and molecular biology. 2013 Nov; 48(6):561-74. doi: 10.3109/10409238.2013.838204. [PMID: 24050258]
  • Ilias Zafiriadis, Spyridon Ntougias, Anastasios G Kapagiannidis, Alexander Aivasidis. Metabolic behavior and enzymatic aspects of denitrifying EBPR sludge in a continuous-flow anaerobic-anoxic system. Applied biochemistry and biotechnology. 2013 Oct; 171(4):939-53. doi: 10.1007/s12010-013-0390-0. [PMID: 23912208]
  • 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]
  • Stephen M G Duff, Timothy J Rydel, Amanda L McClerren, Wenlan Zhang, Jimmy Y Li, Eric J Sturman, Coralie Halls, Songyang Chen, Jiamin Zeng, Jiexin Peng, Crystal N Kretzler, Artem Evdokimov. The enzymology of alanine aminotransferase (AlaAT) isoforms from Hordeum vulgare and other organisms, and the HvAlaAT crystal structure. Archives of biochemistry and biophysics. 2012 Dec; 528(1):90-101. doi: 10.1016/j.abb.2012.06.006. [PMID: 22750542]
  • Angela Ruban, Tamara Berkutzki, Itzik Cooper, Boaz Mohar, Vivian I Teichberg. Blood glutamate scavengers prolong the survival of rats and mice with brain-implanted gliomas. Investigational new drugs. 2012 Dec; 30(6):2226-35. doi: 10.1007/s10637-012-9799-5. [PMID: 22392507]
  • Paolo Dell' Antone. Energy metabolism in cancer cells: how to explain the Warburg and Crabtree effects?. Medical hypotheses. 2012 Sep; 79(3):388-92. doi: 10.1016/j.mehy.2012.06.002. [PMID: 22770870]
  • Anthony Gandin, Claire Duffes, David A Day, Asaph B Cousins. The absence of alternative oxidase AOX1A results in altered response of photosynthetic carbon assimilation to increasing CO(2) in Arabidopsis thaliana. Plant & cell physiology. 2012 Sep; 53(9):1627-37. doi: 10.1093/pcp/pcs107. [PMID: 22848123]
  • A Pérez-Jiménez, G Cardenete, M C Hidalgo, A García-Alcázar, E Abellán, A E Morales. Metabolic adjustments of Dentex dentex to prolonged starvation and refeeding. Fish physiology and biochemistry. 2012 Aug; 38(4):1145-1157. doi: 10.1007/s10695-011-9600-2. [PMID: 22228074]
  • Yoshinori Tsuji, Iwane Suzuki, Yoshihiro Shiraiwa. Enzymological evidence for the function of a plastid-located pyruvate carboxylase in the Haptophyte alga Emiliania huxleyi: a novel pathway for the production of C4 compounds. Plant & cell physiology. 2012 Jun; 53(6):1043-52. doi: 10.1093/pcp/pcs045. [PMID: 22492231]
  • Arghya Biswas, Syed Imam Rabbani, Kshama Devi. Influence of pioglitazone on experimental heart failure and hyperlipidemia in rats. Indian journal of pharmacology. 2012 May; 44(3):333-9. doi: 10.4103/0253-7613.96305. [PMID: 22701242]
  • Xu-Yu Zu, Qing-Hai Zhang, Jiang-Hua Liu, Ren-Xian Cao, Jing Zhong, Guang-Hui Yi, Zhi-Hua Quan, Giuseppe Pizzorno. ATP citrate lyase inhibitors as novel cancer therapeutic agents. Recent patents on anti-cancer drug discovery. 2012 May; 7(2):154-67. doi: 10.2174/157489212799972954. [PMID: 22339355]
  • Sudhakar Pandurangan, Agnieszka Pajak, Stephen J Molnar, Elroy R Cober, Sangeeta Dhaubhadel, Cinta Hernández-Sebastià, Werner M Kaiser, Randall L Nelson, Steven C Huber, Frédéric Marsolais. Relationship between asparagine metabolism and protein concentration in soybean seed. Journal of experimental botany. 2012 May; 63(8):3173-84. doi: 10.1093/jxb/ers039. [PMID: 22357599]
  • Jun-ichi Hanai, Nathaniel Doro, Atsuo T Sasaki, Susumu Kobayashi, Lewis C Cantley, Pankaj Seth, Vikas P Sukhatme. Inhibition of lung cancer growth: ATP citrate lyase knockdown and statin treatment leads to dual blockade of mitogen-activated protein kinase (MAPK) and phosphatidylinositol-3-kinase (PI3K)/AKT pathways. Journal of cellular physiology. 2012 Apr; 227(4):1709-20. doi: 10.1002/jcp.22895. [PMID: 21688263]
  • Li-Tao Zhang, Zi-Shan Zhang, Hui-Yuan Gao, Xiang-Long Meng, Cheng Yang, Jian-Guo Liu, Qing-Wei Meng. The mitochondrial alternative oxidase pathway protects the photosynthetic apparatus against photodamage in Rumex K-1 leaves. BMC plant biology. 2012 Mar; 12(?):40. doi: 10.1186/1471-2229-12-40. [PMID: 22429403]
  • Constance Schmelzer, Mitsuaki Kitano, Kazunori Hosoe, Frank Döring. Ubiquinol affects the expression of genes involved in PPARα signalling and lipid metabolism without changes in methylation of CpG promoter islands in the liver of mice. Journal of clinical biochemistry and nutrition. 2012 Mar; 50(2):119-26. doi: 10.3164/jcbn.11-19. [PMID: 22448092]
  • O Micle, M Muresan, L Antal, F Bodog, A Bodog. The influence of homocysteine and oxidative stress on pregnancy outcome. Journal of medicine and life. 2012 Feb; 5(1):68-73. doi: NULL. [PMID: 22574089]
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  • Inga Hebbelmann, Jennifer Selinski, Corinna Wehmeyer, Tatjana Goss, Ingo Voss, Paula Mulo, Saijaliisa Kangasjärvi, Eva-Mari Aro, Marie-Luise Oelze, Karl-Josef Dietz, Adriano Nunes-Nesi, Phuc T Do, Alisdair R Fernie, Sai K Talla, Agepati S Raghavendra, Vera Linke, Renate Scheibe. Multiple strategies to prevent oxidative stress in Arabidopsis plants lacking the malate valve enzyme NADP-malate dehydrogenase. Journal of experimental botany. 2012 Feb; 63(3):1445-59. doi: 10.1093/jxb/err386. [PMID: 22140244]
  • Francisco Campos, Tomás Sobrino, Pedro Ramos-Cabrer, José Castillo. Oxaloacetate: a novel neuroprotective for acute ischemic stroke. The international journal of biochemistry & cell biology. 2012 Feb; 44(2):262-5. doi: 10.1016/j.biocel.2011.11.003. [PMID: 22085530]
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