N-Acetyl-L-aspartic acid (BioDeep_00000001686)

 

Secondary id: BioDeep_00000265248, BioDeep_00000399929, BioDeep_00000400346, BioDeep_00000412715

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


N-Acetylaspartate, monopotassium salt

化学式: C6H9NO5 (175.0480704)
中文名称: N-乙酰-L-天门冬氨酸, N-乙酰-DL-天冬氨酸, N-乙酰-DL-天冬氨酸, N-乙酰-天冬氨酸, N-乙酰基-L-天冬氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.47%

分子结构信息

SMILES: CC(=O)NC(CC(=O)O)C(=O)O
InChI: InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)

描述信息

N-Acetyl-L-Aspartic acid (NAA) or N-Acetylaspartic acid, 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-alpha-Acetyl-L-aspartic acid can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyl-L-aspartic acid is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-aspartic acid. 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-acetylaspartate 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 aspartic acid can also occur. In particular, N-Acetyl-L-aspartic acid can be synthesized in neurons from the amino acid aspartate and acetyl coenzyme A (acetyl CoA). Specifically, the enzyme known as aspartate N-acetyltransferase (EC 2.3.1.17) catalyzes the transfer of the acetyl group of acetyl CoA to the amino group of aspartate. N-Acetyl-L-aspartic acid is the second most concentrated molecule in the brain after the amino acid glutamate. The various functions served by N-acetylaspartic acid are still under investigation, but the primary proposed functions include (1) acting as a neuronal osmolyte that is involved in fluid balance in the brain, (2) serving as a source of acetate for lipid and myelin synthesis in oligodendrocytes (the glial cells that myelinate neuronal axons), (3) serving as a precursor for the synthesis of the important dipeptide neurotransmitter N-acetylaspartylglutamate (NAAG), and (4) playing a potential role in energy production from the amino acid glutamate in neuronal mitochondria. High neurotransmitter (i.e. N-acetylaspartic acid) levels can lead to abnormal neural signaling, delayed or arrested intellectual development, and difficulties with general motor skills. When present in sufficiently high levels, N-acetylaspartic acid can be a neurotoxin, an acidogen, and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural tissue. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of N-acetylaspartic acid are associated with Canavan disease. Because N-acetylaspartic acid functions as an organic acid and high levels of organic acids can lead to a condition known...
N-Acetylaspartic acid is a derivative of aspartic acid. It is the second most concentrated molecule in the brain after the amino acid glutamate. It is synthesized in neurons from the amino acid aspartate and acetyl coenzyme A. The various functions served by N-acetylaspartic acid are still under investigation, but the primary proposed functions include:
Acquisition and generation of the data is financially supported in part by CREST/JST.
D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids
KEIO_ID A142
N-Acetyl-L-aspartic acid is a derivative of aspartic acid.

同义名列表

25 个代谢物同义名

N-Acetylaspartate, monopotassium salt; (S)-2-(Acetylamino)butanedioic acid; (S)-2-(Acetylamino)succinic acid; (2S)-2-Acetamidobutanedioic acid; (S)-2-(Acetylamino)butanedioate; (S)-2-(Acetylamino)succinate; (2S)-2-Acetamidobutanedioate; N-Acetyl-DL-aspartic acid; N-Acetyl-S-aspartic acid; N-acetyl-L-aspartic acid; L-N-Acetylaspartic acid; Acetyl-L-aspartic acid; N-Acetylaspartic acid; Acetyl aspartic acid; N-Acetyl-L-aspartate; N-Acetyl-S-aspartate; Acetylaspartic acid; L-N-Acetylaspartate; Acetyl-L-aspartate; N-Acetyl aspartate; N-Acetylaspartate; Acetylaspartate; Ac-Asp; NAA; N-Acetylaspartic acid



数据库引用编号

33 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

70 个相关的代谢反应过程信息。

Reactome(56)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(12)

PharmGKB(0)

4 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

  • Anoushka Lotun, Danning Li, Hongxia Xu, Qin Su, Serafettin Tuncer, Julio Sanmiguel, Morgan Mooney, Christina E Baer, Russell Ulbrich, Stephen J Eyles, Lara Strittmatter, Lawrence J Hayward, Dominic J Gessler, Guangping Gao. Renewal of Oligodendrocyte Lineage Reverses Dysmyelination and CNS Neurodegeneration Through Corrected N-acetylaspartate Metabolism. Progress in neurobiology. 2023 May; ?(?):102460. doi: 10.1016/j.pneurobio.2023.102460. [PMID: 37149081]
  • Eleni Rebelos, Giuseppe Daniele, Beatrice Campi, Alessandro Saba, Kalle Koskensalo, Jukka Ihalainen, Ekaterina Saukko, Pirjo Nuutila, Walter H Backes, Jacobus F A Jansen, Pieter C Dagnelie, Sebastian Köhler, Bastiaan E de Galan, Thomas T van Sloten, Coen D A Stehouwer, Ele Ferrannini. Circulating N-Acetylaspartate does not track brain NAA concentrations, cognitive function or features of small vessel disease in humans. Scientific reports. 2022 Jul; 12(1):11530. doi: 10.1038/s41598-022-15670-0. [PMID: 35798828]
  • Thaysa Mara Gazzotto Neves, Estefania Simoes, Maria Concepcíon García Otaduy, Elie Leal de Barros Calfat, Pâmela Bertolazzi, Naomi Antunes da Costa, Fábio Luís de Souza Duran, Joanna Correia-Lima, Maria da Graça Morais Martin, Marília Cerqueira Leite Seelander, Victor Henrique Oyamada Otani, Thais Zélia Dos Santos Otani, Daniel Augusto Corrêa Vasques, Geraldo Busatto Filho, Cristiane Kochi, Ricardo Riyoiti Uchida. Inverse Association Between Hypothalamic N-Acetyl Aspartate/Creatine Ratio and Indices of Body Mass in Adolescents with Obesity. The Journal of nutrition. 2022 03; 152(3):663-670. doi: 10.1093/jn/nxab415. [PMID: 34888674]
  • Kimberly A Lewis, Nico Osier, Ruy Carrasco, Jennifer Chiou, Patricia Carter, Alexandra Garcia, Elena Flowers, Efstathios D Gennatas, Christina Nguyen, Ambreen Rana, Sharon A Brown, Stefano Tiziani. Serine, N-acetylaspartate differentiate adolescents with juvenile idiopathic arthritis compared with healthy controls: a metabolomics cross-sectional study. Pediatric rheumatology online journal. 2022 Feb; 20(1):12. doi: 10.1186/s12969-022-00672-z. [PMID: 35144633]
  • Laura L Gramegna, Stefania Evangelisti, Lidia Di Vito, Chiara La Morgia, Alessandra Maresca, Leonardo Caporali, Giulia Amore, Lia Talozzi, Claudio Bianchini, Claudia Testa, David N Manners, Irene Cortesi, Maria L Valentino, Rocco Liguori, Valerio Carelli, Caterina Tonon, Raffaele Lodi. Brain MRS correlates with mitochondrial dysfunction biomarkers in MELAS-associated mtDNA mutations. Annals of clinical and translational neurology. 2021 06; 8(6):1200-1211. doi: 10.1002/acn3.51329. [PMID: 33951347]
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  • Beatrice Campi, Simone Codini, Giuseppe Daniele, Antonella Marvelli, Giovanni Ceccarini, Ferruccio Santini, Riccardo Zucchi, Ele Ferrannini, Alessandro Saba. Plasma N-acetylaspartate: Development and validation of a quantitative assay based on HPLC-MS-MS and sample derivatization. Clinica chimica acta; international journal of clinical chemistry. 2020 Sep; 508(?):146-153. doi: 10.1016/j.cca.2020.05.020. [PMID: 32417212]
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  • Giuseppe Daniele, Beatrice Campi, Alessandro Saba, Simone Codini, Annamaria Ciccarone, Laura Giusti, Stefano Del Prato, Russel L Esterline, Ele Ferrannini. Plasma N-Acetylaspartate Is Related to Age, Obesity, and Glucose Metabolism: Effects of Antidiabetic Treatment and Bariatric Surgery. Frontiers in endocrinology. 2020; 11(?):216. doi: 10.3389/fendo.2020.00216. [PMID: 32362872]
  • Joshua Chiappelli, Laura M Rowland, S Andrea Wijtenburg, Hongji Chen, Andrew A Maudsley, Sulaiman Sheriff, Shuo Chen, Anya Savransky, Wyatt Marshall, Meghann C Ryan, Heather A Bruce, Alan R Shuldiner, Braxton D Mitchell, Peter Kochunov, L Elliot Hong. Cardiovascular risks impact human brain N-acetylaspartate in regionally specific patterns. Proceedings of the National Academy of Sciences of the United States of America. 2019 12; 116(50):25243-25249. doi: 10.1073/pnas.1907730116. [PMID: 31754041]
  • Dina C Hofer, Gabriel Zirkovits, Helmut J Pelzmann, Katharina Huber, Ariane R Pessentheiner, Wenmin Xia, Kyosuke Uno, Toh Miyazaki, Kanta Kon, Hiroshi Tsuneki, Tobias Pendl, Wael Al Zoughbi, Corina T Madreiter-Sokolowski, Gert Trausinger, Mahmoud Abdellatif, Gabriele Schoiswohl, Renate Schreiber, Tobias Eisenberg, Christoph Magnes, Simon Sedej, Matthias Eckhardt, Masakiyo Sasahara, Toshiyasu Sasaoka, Atsumi Nitta, Gerald Hoefler, Wolfgang F Graier, Dagmar Kratky, Johan Auwerx, Juliane G Bogner-Strauss. N-acetylaspartate availability is essential for juvenile survival on fat-free diet and determines metabolic health. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2019 12; 33(12):13808-13824. doi: 10.1096/fj.201801323r. [PMID: 31638418]
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  • Aljoharah Alakkas, Ronald J Ellis, Caitlin Wei-Ming Watson, Anya Umlauf, Robert K Heaton, Scott Letendre, Ann Collier, Christina Marra, David B Clifford, Benjamin Gelman, Ned Sacktor, Susan Morgello, David Simpson, J Allen McCutchan, Asha Kallianpur, Sara Gianella, Thomas Marcotte, Igor Grant, Christine Fennema-Notestine. White matter damage, neuroinflammation, and neuronal integrity in HAND. Journal of neurovirology. 2019 02; 25(1):32-41. doi: 10.1007/s13365-018-0682-9. [PMID: 30291567]
  • I I Miroshnichenko, O B Yakovleva, T P Safarova, E S Shipilova, N V Baymeeva. [The content of N-acetylaspartate in depressed elderly patients during therapy with antidepressants and actovegin]. Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova. 2019; 119(4):38-42. doi: 10.17116/jnevro201911904138. [PMID: 31156220]
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  • Talitha C Ford, Luke A Downey, Tamara Simpson, Grace McPhee, Chris Oliver, Con Stough. The Effect of a High-Dose Vitamin B Multivitamin Supplement on the Relationship between Brain Metabolism and Blood Biomarkers of Oxidative Stress: A Randomized Control Trial. Nutrients. 2018 Dec; 10(12):. doi: 10.3390/nu10121860. [PMID: 30513795]
  • Xueying Ma, Yan Zhang, Shaohui Ma, Peng Li, Dun Ding, Hua Liu, Jixin Liu, Ming Zhang. Association between abnormal thalamic metabolites and sleep disturbance in patients with end-stage renal disease. Metabolic brain disease. 2018 10; 33(5):1641-1648. doi: 10.1007/s11011-018-0272-9. [PMID: 29974312]
  • Paul Chang, Sahar Nassirpour, Nikolai Avdievitch, Anke Henning. Non-water-suppressed 1 H FID-MRSI at 3T and 9.4T. Magnetic resonance in medicine. 2018 08; 80(2):442-451. doi: 10.1002/mrm.27049. [PMID: 29285781]
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