N-acetylglutamate (BioDeep_00000001389)

 

Secondary id: BioDeep_00000405417, BioDeep_00000405920, BioDeep_00000415771

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


N-Acetylglutamate, calcium salt (1:1), (L)-isomer

化学式: C7H11NO5 (189.0637196)
中文名称: N-乙酰谷氨酸, N-乙酰-L-谷氨酸, N-乙酰-L-谷氨酰胺, N-乙酰-DL-谷氨酸
谱图信息: 最多检出来源 Homo sapiens(feces) 27.75%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

N-acetylglutamate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/n-acetylglutamate (retrieved 2024-11-28) (BioDeep RN: BioDeep_00000001389). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)

描述信息

N-Acetyl-L-glutamic acid or N-Acetylglutamate, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetyl-L-glutamate can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-glutamate is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-glutamic acid. N-Acetyl-L-glutamic acid is found in all organisms ranging from bacteria to plants to animals. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\\\% of all human proteins and 68\\\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylglutamate can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free glutamic acid can also occur. In particular, N-Acetyl-L-glutamic acid can be biosynthesized from glutamate and acetylornithine by ornithine acetyltransferase, and from glutamic acid and acetyl-CoA by the enzyme known as N-acetylglutamate synthase. N-Acetyl-L-glutamic acid is the first intermediate involved in the biosynthesis of arginine in prokaryotes and simple eukaryotes and a regulator of the urea cycle in vertebrates. In vertebrates, N-acetylglutamic acid is the allosteric activator molecule to mitochondrial carbamyl phosphate synthetase I (CPSI) which is the first enzyme in the urea cycle. It triggers the production of the first urea cycle intermediate, a compound known as carbamyl phosphate. Notably the CPSI enzyme is inactive when N-acetylglutamic acid is not present. A deficiency in N-acetyl glutamate synthase or a genetic mutation in the gene coding for the enzyme will lead to urea cycle failure in which ammonia is not converted to urea, but rather accumulated in the blood leading to the condition called Type I hyperammonemia. Excessive amounts N-acetyl amino acids can be detected in the urine with individuals with aminoacylase I deficiency, a genetic disorder (PMID: 16465618). These include N-acetylalanine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylglycine, N-acetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine. Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924). Individuals with aminoacylase I deficiency w...
N-acetyl-l-glutamate, also known as L-N-acetylglutamic acid or ac-glu-oh, belongs to glutamic acid and derivatives class of compounds. Those are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-acetyl-l-glutamate is soluble (in water) and a weakly acidic compound (based on its pKa). N-acetyl-l-glutamate can be found in a number of food items such as cardoon, almond, butternut squash, and avocado, which makes N-acetyl-l-glutamate a potential biomarker for the consumption of these food products. N-acetyl-l-glutamate may be a unique S.cerevisiae (yeast) metabolite.
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID A031
N-Acetyl-L-glutamic acid, a glutamic acid, is a component of animal cell culturing media. N-Acetyl-L-glutamic acid is a metabolite of Saccharomyces cerevisiae and human[1].
N-Acetyl-L-glutamic acid, a glutamic acid, is a component of animal cell culturing media. N-Acetyl-L-glutamic acid is a metabolite of Saccharomyces cerevisiae and human[1].

同义名列表

35 个代谢物同义名

N-Acetylglutamate, calcium salt (1:1), (L)-isomer; N-Acetylglutamate, dipotassium salt, (L)-isomer; N-Acetylglutamate, monosodium salt, (L)-isomer; N-Acetylglutamate, potassium salt, (L)-isomer; N-Acetylglutamate, magnesium salt, (L)-isomer; N-Acetylglutamate, disodium salt, (L)-isomer; N-Acetylglutamate, calcium salt, (L)-isomer; (S)-2-(Acetylamino)pentanedioic acid; N-Acetylglutamic acid semialdehyde; (2S)-2-acetamidopentanedioic acid; (S)-2-(Acetylamino)pentanedioate; alpha-(N-Acetyl)-L-glutamic acid; N-Acetylglutamate, (DL)-isomer; N-Acetylglutamate, (D)-isomer; Α-(N-acetyl)-L-glutamic acid; N-Acetyl-L-glutaminic acid; N-Acetyl-DL-glutamic acid; N-Acetyl-L-glutamic acid; Sodium N-acetylglutamate; L-N-Acetylglutamic acid; Acetyl-L-glutamic acid; N-Acetylglutamic acid; N-ACETYL-L-glutamATE; L-N-Acetylglutamate; Acetylglutamic acid; Acetyl-L-glutamate; N-Acetylglutamate; Acetylglutamate; N-Ac-glu-OH; Ac-glu-OH; NAcGlu; Ac-Glu; N-Acetylglutamic acid; N-Acetyl-L-glutamic acid; N-Acetyl-L-glutamate



数据库引用编号

39 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

483 个相关的代谢反应过程信息。

Reactome(33)

BioCyc(0)

WikiPathways(0)

Plant Reactome(444)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(6)

PharmGKB(0)

15 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

  • Katrine D Galsgaard, Jens Pedersen, Sasha A S Kjeldsen, Marie Winther-Sørensen, Elena Stojanovska, Hendrik Vilstrup, Cathrine Ørskov, Nicolai J Wewer Albrechtsen, Jens J Holst. Glucagon receptor signaling is not required for N-carbamoyl glutamate- and l-citrulline-induced ureagenesis in mice. American journal of physiology. Gastrointestinal and liver physiology. 2020 05; 318(5):G912-G927. doi: 10.1152/ajpgi.00294.2019. [PMID: 32174131]
  • Barbora Vorlova, Tomas Knedlik, Jan Tykvart, Jan Konvalinka. GCPII and its close homolog GCPIII: from a neuropeptidase to a cancer marker and beyond. Frontiers in bioscience (Landmark edition). 2019 03; 24(4):648-687. doi: 10.2741/4742. [PMID: 30844704]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Birgitta C Burckhardt, Gerhard Burckhardt. Interaction of Excitatory Amino Acid Transporters 1 - 3 (EAAT1, EAAT2, EAAT3) with N-Carbamoylglutamate and N-Acetylglutamate. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2017; 43(5):1907-1916. doi: 10.1159/000484110. [PMID: 29055942]
  • Primal Sharma, Priyanka A Shah, Mallika Sanyal, Pranav S Shrivastav. Challenges in optimizing sample preparation and LC-MS/MS conditions for the analysis of carglumic acid, an N-acetyl glutamate derivative in human plasma. Drug testing and analysis. 2015 Sep; 7(9):763-72. doi: 10.1002/dta.1774. [PMID: 25677217]
  • Yohannes Hagos, Gerhard Burckhardt, Birgitta C Burckhardt. Human organic anion transporter OAT1 is not responsible for glutathione transport but mediates transport of glutamate derivatives. American journal of physiology. Renal physiology. 2013 Feb; 304(4):F403-9. doi: 10.1152/ajprenal.00412.2012. [PMID: 23255614]
  • Gengxiang Zhao, Zhongmin Jin, Norma M Allewell, Mendel Tuchman, Dashuang Shi. Crystal structure of the N-acetyltransferase domain of human N-acetyl-L-glutamate synthase in complex with N-acetyl-L-glutamate provides insights into its catalytic and regulatory mechanisms. PloS one. 2013; 8(7):e70369. doi: 10.1371/journal.pone.0070369. [PMID: 23894642]
  • Dae Eun Choi, Kang Wook Lee, Young Tai Shin, Ki Ryang Na. Hyperammonemia in a patient with late-onset ornithine carbamoyltransferase deficiency. Journal of Korean medical science. 2012 May; 27(5):556-9. doi: 10.3346/jkms.2012.27.5.556. [PMID: 22563224]
  • Wataru Takagi, Makiko Kajimura, Justin D Bell, Tes Toop, John A Donald, Susumu Hyodo. Hepatic and extrahepatic distribution of ornithine urea cycle enzymes in holocephalan elephant fish (Callorhinchus milii). Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2012 Apr; 161(4):331-40. doi: 10.1016/j.cbpb.2011.12.006. [PMID: 22227372]
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  • Luigi Atzori, Roberto Antonucci, Luigi Barberini, Emanuela Locci, Flaminia Cesare Marincola, Paola Scano, Patrizia Cortesi, Rino Agostiniani, Riccardo Defraia, Aalim Weljie, Diego Gazzolo, Adolfo Lai, Vassilios Fanos. 1H NMR-based metabolomic analysis of urine from preterm and term neonates. Frontiers in bioscience (Elite edition). 2011 06; 3(3):1005-12. doi: 10.2741/e306. [PMID: 21622109]
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  • Magdalena Stepien, Claire Gaudichon, Gilles Fromentin, Patrick Even, Daniel Tomé, Dalila Azzout-Marniche. Increasing protein at the expense of carbohydrate in the diet down-regulates glucose utilization as glucose sparing effect in rats. PloS one. 2011 Feb; 6(2):e14664. doi: 10.1371/journal.pone.0014664. [PMID: 21326875]
  • Marta Daniotti, Giancarlo la Marca, Patrizio Fiorini, Luca Filippi. New developments in the treatment of hyperammonemia: emerging use of carglumic acid. International journal of general medicine. 2011 Jan; 4(?):21-8. doi: 10.2147/ijgm.s10490. [PMID: 21403788]
  • Johannes Häberle. Role of carglumic acid in the treatment of acute hyperammonemia due to N-acetylglutamate synthase deficiency. Therapeutics and clinical risk management. 2011; 7(?):327-32. doi: 10.2147/tcrm.s12703. [PMID: 21941437]
  • Kazuyo Tujioka, Miho Ohsumi, Kazutoshi Hayase, Hidehiko Yokogoshi. Effect of the quality of dietary amino acids composition on the urea synthesis in rats. Journal of nutritional science and vitaminology. 2011; 57(1):48-55. doi: 10.3177/jnsv.57.48. [PMID: 21512291]
  • Surjit Tarafdar, Mark Slee, Faisal Ameer, Matt Doogue. A case of valproate induced hyperammonemic encephalopathy. Case reports in medicine. 2011; 2011(?):969505. doi: 10.1155/2011/969505. [PMID: 21629819]
  • Harin Kanani, Bhaskar Dutta, Maria I Klapa. Individual vs. combinatorial effect of elevated CO2 conditions and salinity stress on Arabidopsis thaliana liquid cultures: comparing the early molecular response using time-series transcriptomic and metabolomic analyses. BMC systems biology. 2010 Dec; 4(?):177. doi: 10.1186/1752-0509-4-177. [PMID: 21190570]
  • Tong Wang, Erhua Zhang, Xiaoping Chen, Ling Li, Xuanqiang Liang. Identification of seed proteins associated with resistance to pre-harvested aflatoxin contamination in peanut (Arachis hypogaea L). BMC plant biology. 2010 Nov; 10(?):267. doi: 10.1186/1471-2229-10-267. [PMID: 21118527]
  • Sébastien Baud, Ana Belen Feria Bourrellier, Marianne Azzopardi, Adeline Berger, Julie Dechorgnat, Françoise Daniel-Vedele, Loïc Lepiniec, Martine Miquel, Christine Rochat, Michael Hodges, Sylvie Ferrario-Méry. PII is induced by WRINKLED1 and fine-tunes fatty acid composition in seeds of Arabidopsis thaliana. The Plant journal : for cell and molecular biology. 2010 Oct; 64(2):291-303. doi: 10.1111/j.1365-313x.2010.04332.x. [PMID: 21070409]
  • Markus Schrettl, Nicola Beckmann, John Varga, Thorsten Heinekamp, Ilse D Jacobsen, Christoph Jöchl, Tarek A Moussa, Shaohua Wang, Fabio Gsaller, Michael Blatzer, Ernst R Werner, William C Niermann, Axel A Brakhage, Hubertus Haas. HapX-mediated adaption to iron starvation is crucial for virulence of Aspergillus fumigatus. PLoS pathogens. 2010 Sep; 6(9):e1001124. doi: 10.1371/journal.ppat.1001124. [PMID: 20941352]
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