Pyruvic acid (BioDeep_00000406172)

Main id: BioDeep_00000002915

 

PANOMIX_OTCML-2023 BioNovoGene_Lab2019 natural product


代谢物信息卡片


alpha-keto propionic acid

化学式: C3H4O3 (88.016)
中文名称: 丙酮酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(=O)C(=O)O
InChI: 4H,1H2,(H,5,6)

描述信息

A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.
Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures (From Stedman, 26th ed.). Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds); Pyruvate is a key intersection in the network of metabolic pathways. Pyruvate can be converted into carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine and to ethanol. Therefore it unites several key metabolic processes.; Pyruvate is an important chemical compound in biochemistry. It is the output of the anaerobic metabolism of glucose known as glycolysis. One molecule of glucose breaks down into two molecules of pyruvate, which are then used to provide further energy, in one of two ways. Pyruvate is converted into acetyl-coenzyme A, which is the main input for a series of reactions known as the Krebs cycle. Pyruvate is also converted to oxaloacetate by an anaplerotic reaction which replenishes Krebs cycle intermediates; alternatively, the oxaloacetate is used for gluconeogenesis. These reactions are named after Hans Adolf Krebs, the biochemist awarded the 1953 Nobel Prize for physiology, jointly with Fritz Lipmann, for research into metabolic processes. The cycle is also called the citric acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.; Pyruvic acid (CH3COCOOH) is an organic acid. It is also a ketone, as well as being the simplest alpha-keto acid. The carboxylate (COOH) ion (anion) of pyruvic acid, CH3COCOO-, is known as pyruvate, and is a key intersection in several metabolic pathways. It can be made from glucose through glycolysis, supplies energy to living cells in the citric acid cycle, and can also be converted to carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl-CoA, to the amino acid alanine and to ethanol.; Pyruvic acid is a colorless liquid with a smell similar to that of acetic acid. It is miscible with water, and soluble in ethanol and diethyl ether. In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and potassium hydrogen sulfate, by the oxidation of propylene glycol by a strong oxidizer (eg. potassium permanganate or bleach), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide:; Pyruvic acid or pyruvate is a key intermediate in the glycolytic and pyruvate dehydrogenase pathways, which are involved in biological energy production. Pyruvate is widely found in living organisms. It is not an essential nutrient since it can be synthesized in the cells of the body. Certain fruits and vegetables are rich in pyruvate. For example, an average-size red apple contains approximately 450 milligrams. Dark beer and red wine are also rich sources of pyruvate. Recent research suggests that pyruvate in high concentrations may have a role in cardiovascular therapy, as an inotropic agent. Supplements of this dietary substance may also have bariatric and ergogenic applications. Pyruvic acid is isolated from cane sugar fermentation broth, Cicer arietinum (chickpea), Pisum sativum (pea), Trigonella cerulea (sweet trefoil) and peppermint. It can be used as a flavouring ingredient.
Pyruvic acid is an intermediate metabolite in the metabolism of carbohydrates, proteins, and fats.
Pyruvic acid is an intermediate metabolite in the metabolism of carbohydrates, proteins, and fats.

同义名列表

7 个代谢物同义名

Pyruvic acid; alpha-keto propionic acid; 2-oxo-propinoic acid; FA 3:1;O; Acetylformic acid; Pyruvate; Pyruvic acid



数据库引用编号

27 个数据库交叉引用编号

分类词条

93 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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 CASP3, CAT, G6PD, GAPDH, HMGB1, LDHA, PC, PKM, XDH
Peripheral membrane protein 4 G6PD, GORASP1, HK2, HMGB1
Endoplasmic reticulum membrane 1 TKT
Nucleus 5 CASP3, GAPDH, HMGB1, LDHA, PKM
cytosol 13 CASP3, CAT, G6PD, GAPDH, GPT, HK2, LDHA, LIPE, PC, PGK1, PKM, TKT, XDH
nuclear body 1 TKT
centrosome 1 HK2
nucleoplasm 4 ATP2B1, CASP3, HMGB1, TKT
Cell membrane 5 ATP2B1, HMGB1, LIPE, TKT, TNF
Cytoplasmic side 1 GORASP1
Multi-pass membrane protein 1 ATP2B1
Golgi apparatus membrane 1 GORASP1
Synapse 1 ATP2B1
cell surface 2 HMGB1, TNF
glutamatergic synapse 2 ATP2B1, CASP3
Golgi apparatus 1 GORASP1
Golgi membrane 2 GORASP1, INS
neuronal cell body 2 CASP3, TNF
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 4 G6PD, GAPDH, HK2, LIPE
endosome 1 HMGB1
plasma membrane 6 ATP2B1, GAPDH, GCG, HMGB1, TKT, TNF
synaptic vesicle membrane 1 ATP2B1
Membrane 8 ATP2B1, CAT, G6PD, GAPDH, HK2, LDHA, LIPE, PGK1
apical plasma membrane 1 TKT
axon 1 CCK
basolateral plasma membrane 1 ATP2B1
caveola 1 LIPE
extracellular exosome 9 ATP2B1, CAT, G6PD, GAPDH, GPT, LDHA, PGK1, PKM, TKT
endoplasmic reticulum 1 HMGB1
extracellular space 7 CCK, GCG, HMGB1, INS, PGK1, TNF, XDH
perinuclear region of cytoplasm 1 GAPDH
mitochondrion 5 CAT, HK2, LDHA, PC, PKM
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 5 ATP2B1, CAT, G6PD, GAPDH, HK2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TKT
Secreted 5 CCK, GCG, HK2, HMGB1, INS
extracellular region 7 CAT, CCK, GCG, HMGB1, INS, PKM, TNF
cytoplasmic side of plasma membrane 1 G6PD
Mitochondrion outer membrane 1 HK2
mitochondrial outer membrane 1 HK2
Mitochondrion matrix 1 PC
mitochondrial matrix 2 CAT, PC
Extracellular side 1 HMGB1
centriolar satellite 1 G6PD
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
nuclear membrane 1 GAPDH
external side of plasma membrane 1 TNF
Extracellular vesicle 1 PKM
actin cytoskeleton 1 TKT
microtubule cytoskeleton 1 GAPDH
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 3 GAPDH, PKM, TKT
Cytoplasm, perinuclear region 1 GAPDH
Membrane raft 2 PGK1, TNF
Cytoplasm, cytoskeleton 1 GAPDH
focal adhesion 2 CAT, TKT
cis-Golgi network 1 GORASP1
Peroxisome 3 CAT, TKT, XDH
sarcoplasmic reticulum 2 HK2, XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 PKM
lateral plasma membrane 1 ATP2B1
receptor complex 1 TKT
cilium 1 PKM
cell projection 1 ATP2B1
phagocytic cup 1 TNF
Chromosome 1 HMGB1
cytoskeleton 1 GAPDH
Basolateral cell membrane 1 ATP2B1
endosome lumen 1 INS
Lipid droplet 2 GAPDH, LIPE
Membrane, caveola 1 LIPE
Presynaptic cell membrane 1 ATP2B1
ficolin-1-rich granule lumen 3 CAT, HMGB1, PKM
secretory granule lumen 5 CAT, GCG, HMGB1, INS, PKM
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 GCG, INS
transcription repressor complex 1 HMGB1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
immunological synapse 1 ATP2B1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
ribonucleoprotein complex 1 GAPDH
endoplasmic reticulum-Golgi intermediate compartment 1 HMGB1
death-inducing signaling complex 1 CASP3
Rough endoplasmic reticulum 1 PKM
condensed chromosome 1 HMGB1
GAIT complex 1 GAPDH
oxidoreductase complex 1 LDHA
[Glucagon-like peptide 1]: Secreted 1 GCG
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
alphav-beta3 integrin-HMGB1 complex 1 HMGB1
photoreceptor ribbon synapse 1 ATP2B1
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Alexander S Shashkov, Natalia V Potekhina, Elena M Tul'skaya, Andrey S Dmitrenok, Sof'ya N Senchenkova, Vladimir I Torgov, Lubov V Dorofeeva, Lyudmila I Evtushenko. New lactate- and pyruvate-containing polysaccharide and rhamnomannan with xylose residues from the cell wall of Rathayibacter oskolensis VKM Ac-2121T. Carbohydrate research. 2024 Jun; 540(?):109145. doi: 10.1016/j.carres.2024.109145. [PMID: 38759341]
  • Anne Jahn, Maike Petersen. Hydroxy(phenyl)pyruvic acid reductase in Actaea racemosa L.: a putative enzyme in cimicifugic and fukinolic acid biosynthesis. Planta. 2024 Mar; 259(5):102. doi: 10.1007/s00425-024-04382-6. [PMID: 38549005]
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  • Josepheena Joseph, Sanjib Bal Samant, Kapuganti Jagadis Gupta. Mitochondrial alternative oxidase pathway helps in nitrooxidative stress tolerance in germinating chickpea. Journal of biosciences. 2024; 49(?):. doi: ". [PMID: 38726824]
  • João Vitor Alcantara da Silva, Jessica Ispada, Ricardo Perecin Nociti, Aldcejam Martins da Fonseca Junior, Camila Bruna De Lima, Erika Cristina Dos Santos, Marcos Roberto Chiaratti, Marcella Pecora Milazzotto. The central role of pyruvate metabolism on the epigenetic maturation and transcriptional profile of bovine oocytes. Reproduction (Cambridge, England). 2024 Jan; ?(?):. doi: 10.1530/rep-23-0181. [PMID: 38271822]
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  • Toshiharu Onodera, May-Yun Wang, Joseph M Rutkowski, Stanislaw Deja, Shiuhwei Chen, Michael S Balzer, Dae-Seok Kim, Xuenan Sun, Yu A An, Bianca C Field, Charlotte Lee, Ei-Ichi Matsuo, Monika Mizerska, Ina Sanjana, Naoto Fujiwara, Christine M Kusminski, Ruth Gordillo, Laurent Gautron, Denise K Marciano, Ming Chang Hu, Shawn C Burgess, Katalin Susztak, Orson W Moe, Philipp E Scherer. Endogenous renal adiponectin drives gluconeogenesis through enhancing pyruvate and fatty acid utilization. Nature communications. 2023 10; 14(1):6531. doi: 10.1038/s41467-023-42188-4. [PMID: 37848446]
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  • Hira Shakoor, Jaleel Kizhakkayil, Mariyam Khalid, Amar Mahgoub, Carine Platat. Effect of Moderate-Intense Training and Detraining on Glucose Metabolism, Lipid Profile, and Liver Enzymes in Male Wistar Rats: A Preclinical Randomized Study. Nutrients. 2023 Aug; 15(17):. doi: 10.3390/nu15173820. [PMID: 37686852]
  • An-Hui Jin, Yi-Fan Qian, Jiong Ren, Jin-Gang Wang, Fang Qiao, Mei-Ling Zhang, Zhen-Yu Du, Yuan Luo. PDK inhibition promotes glucose utilization, reduces hepatic lipid deposition, and improves oxidative stress in largemouth bass (Micropterus salmoides) by increasing pyruvate oxidative phosphorylation. Fish & shellfish immunology. 2023 Jul; 140(?):108969. doi: 10.1016/j.fsi.2023.108969. [PMID: 37488039]
  • Yanping Zhao, Xu Geng, Xiaoling Zhou, Li Xu, Shuai Li, Zhengqiang Li, Yi Guo, Chen Li. A novel high-stability bioelectrochemical sensor based on sol-gel immobilization of lactate dehydrogenase and AuNPs-rGO signal enhancement for serum pyruvate detection. Analytica chimica acta. 2023 Jul; 1265(?):341335. doi: 10.1016/j.aca.2023.341335. [PMID: 37230575]
  • Ju-Yi Hsieh, Kun-Chi Chen, Chun-Hsiung Wang, Guang-Yaw Liu, Jie-An Ye, Yu-Tung Chou, Yi-Chun Lin, Cheng-Jhe Lyu, Rui-Ying Chang, Yi-Liang Liu, Yen-Hsien Li, Mau-Rong Lee, Meng-Chiao Ho, Hui-Chih Hung. Suppression of the human malic enzyme 2 modifies energy metabolism and inhibits cellular respiration. Communications biology. 2023 May; 6(1):548. doi: 10.1038/s42003-023-04930-y. [PMID: 37217557]
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  • Saad Alrashdi, Federica Casolari, Aziz Alabed, Kwaku Kyeremeh, Hai Deng. Chemoenzymatic Synthesis of Indole-Containing Acyloin Derivatives. Molecules (Basel, Switzerland). 2023 Jan; 28(1):. doi: 10.3390/molecules28010354. [PMID: 36615552]
  • Jingyu Ni, Hao Zhang, Xiaodan Wang, Zhihao Liu, Tong Nie, Lan Li, Jing Su, Yan Zhu, Chuanrui Ma, Yuting Huang, Jingyuan Mao, Xiumei Gao, Guanwei Fan. Rg3 regulates myocardial pyruvate metabolism via P300-mediated dihydrolipoamide dehydrogenase 2-hydroxyisobutyrylation in TAC-induced cardiac hypertrophy. Cell death & disease. 2022 12; 13(12):1073. doi: 10.1038/s41419-022-05516-y. [PMID: 36572672]
  • Shan Tang, Ning Guo, Qingqing Tang, Fei Peng, Yunhao Liu, Hui Xia, Shaoping Lu, Liang Guo. Pyruvate transporter BnaBASS2 impacts seed oil accumulation in Brassica napus. Plant biotechnology journal. 2022 12; 20(12):2406-2417. doi: 10.1111/pbi.13922. [PMID: 36056567]
  • Kuenzang Om, Nico N Arias, Chaney C Jambor, Alexandra MacGregor, Ashley N Rezachek, Carlan Haugrud, Hans-Henning Kunz, Zhonghui Wang, Pu Huang, Quan Zhang, Josh Rosnow, Thomas P Brutnell, Asaph B Cousins, Chris J Chastain. Pyruvate, phosphate dikinase regulatory protein impacts light response of C4 photosynthesis in Setaria viridis. Plant physiology. 2022 09; 190(2):1117-1133. doi: 10.1093/plphys/kiac333. [PMID: 35876823]
  • Faizan Abul Qais, Suliman Yousef Alomar, Mohammad Azhar Imran, Md Amiruddin Hashmi. In-Silico Analysis of Phytocompounds of Olea europaea as Potential Anti-Cancer Agents to Target PKM2 Protein. Molecules (Basel, Switzerland). 2022 Sep; 27(18):. doi: 10.3390/molecules27185793. [PMID: 36144527]
  • Evelyn Silva Moreira, Ana Paula Ames-Sibin, Carla Indianara Bonetti, Luana Eloísa Leal, Rosane Marina Peralta, Anacharis Babeto de Sá-Nakanishi, Jurandir Fernando Comar, Adelar Bracht, Lívia Bracht. The short-term effects of berberine in the liver: Narrow margins between benefits and toxicity. Toxicology letters. 2022 Sep; 368(?):56-65. doi: 10.1016/j.toxlet.2022.08.005. [PMID: 35963428]
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  • Wei Gao, Yue Zhang, Lai Chen, Xiaoyu Liu, Kun Li, Lijun Han, Zhenwu Yu, Jinzhou Ren, Liangfu Tang, Zhijin Fan. Novel [1,2,4]-Triazolo[3,4-b]-[1,3,4]thiadizoles as Potent Pyruvate Kinase Inhibitors for Fungal Control. Journal of agricultural and food chemistry. 2022 Aug; 70(33):10170-10181. doi: 10.1021/acs.jafc.2c03758. [PMID: 35960265]
  • Jiaxin Cui, Georg Hölzl, Tobias Karmainski, Till Tiso, Sonja Kubicki, Stephan Thies, Lars M Blank, Karl-Erich Jaeger, Peter Dörmann. The Glycine-Glucolipid of Alcanivorax borkumensis Is Resident to the Bacterial Cell Wall. Applied and environmental microbiology. 2022 08; 88(16):e0112622. doi: 10.1128/aem.01126-22. [PMID: 35938787]
  • Kiran Kumar Adepu, Dipendra Bhandari, Andriy Anishkin, Sean H Adams, Sree V Chintapalli. Myoglobin-Pyruvate Interactions: Binding Thermodynamics, Structure-Function Relationships, and Impact on Oxygen Release Kinetics. International journal of molecular sciences. 2022 Aug; 23(15):. doi: 10.3390/ijms23158766. [PMID: 35955898]
  • Dorota Lechniak, Ewa Sell-Kubiak, Ewelina Warzych. The metabolic profile of bovine blastocysts is affected by in vitro culture system and the pattern of first zygotic cleavage. Theriogenology. 2022 Aug; 188(?):43-51. doi: 10.1016/j.theriogenology.2022.05.021. [PMID: 35661988]
  • Nadia Turton, Neve Cufflin, Mollie Dewsbury, Olivia Fitzpatrick, Rahida Islam, Lowidka Linares Watler, Cara McPartland, Sophie Whitelaw, Caitlin Connor, Charlotte Morris, Jason Fang, Ollie Gartland, Liv Holt, Iain P Hargreaves. The Biochemical Assessment of Mitochondrial Respiratory Chain Disorders. International journal of molecular sciences. 2022 Jul; 23(13):. doi: 10.3390/ijms23137487. [PMID: 35806492]
  • Rodney C Daniels, Mohamad H Tiba, Brandon C Cummings, Yan Rou Yap, Sardar Ansari, Brendan M McCracken, Yihan Sun, Theodore S Jennaro, Kevin R Ward, Kathleen A Stringer. Redox Potential Correlates with Changes in Metabolite Concentrations Attributable to Pathways Active in Oxidative Stress Response in Swine Traumatic Shock. Shock (Augusta, Ga.). 2022 06; 57(6):282-290. doi: 10.1097/shk.0000000000001944. [PMID: 35670453]
  • Yiru Shao, Zhiyong Xie, Shusheng Liang, Cuiying Chen, Douglas R Tocher, Li Lin, Yanhua Huang, Yuanyou Li, Dizhi Xie, Yucong Hong, Shuqi Wang, Cuihong You. Dietary calcium pyruvate could improve growth performance and reduce excessive lipid deposition in juvenile golden pompano (Trachinotus ovatus) fed a high fat diet. Fish physiology and biochemistry. 2022 Jun; 48(3):555-570. doi: 10.1007/s10695-022-01077-1. [PMID: 35461391]
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