N-acetyl-aspartyl-glutamate (NAAG) (BioDeep_00000002799)

 

Secondary id: BioDeep_00000015163, BioDeep_00000181527

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2S)-2-[(2S)-3-carboxy-2-acetamidopropanamido]pentanedioic acid

化学式: C11H16N2O8 (304.0906616)
中文名称: 异冬谷酸, N-乙酰基谷氨酸, N-乙酰基-L-天冬氨酰-L-谷氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.14%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

N-acetyl-aspartyl-glutamate (NAAG). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/n-acetyl-aspartyl-glutamate_(naag) (retrieved 2024-09-20) (BioDeep RN: BioDeep_00000002799). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=O)NC(CC(=O)O)C(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)

描述信息

N-Acetylaspartylglutamate (NAAG) is a neuropeptide found in millimolar concentrations in the brain that is localized to subpopulations of glutamatergic, cholinergic, GABAergic, and noradrenergic neuronal systems. NAAG is released upon depolarization by a Ca(2+)-dependent process and is an agonist at mGluR3 receptors and an antagonist at NMDA receptors. NAAG is catabolized to N-acetylaspartate and glutamate primarily by glutamate carboxypeptidase II, which is expressed on the extracellular surface of astrocytes. The levels of NAAG and the activity of carboxypeptidase II are altered in a regionally specific fashion in several neuropsychiatric disorders (PMID:9361299). N-Acetylaspartylglutamic acid (NAAG) is a purported precursor of N-acetylaspartic acid (NAA) and is present at about one-tenth of the concentration of NAA in the brain. NAAG has been reported to activate N-methyl-D-aspartic acid (NMDA) receptors in neurons. Previous immunohistochemical studies in the vertebrate central nervous system (CNS) have suggested that NAAG is exclusively localized to neurons. Recent evidence, however, indicates that NAAG might also be localized to nonneuronal cells within the CNS. Only traces of NAA and NAAG are detectable in other tissues. Some compounds can change levels of NAA and NAAG in the brain. For example, methylphenidate increases the levels of NAA and NAAG in the cerebral cortex; amphetamine also increases NAA concentration in a mature brain by 26\\\%, raising the possibility that other neurochemical systems might be involved in the clinical effects of stimulants (PMID:10603234).
N-Acetylaspartylglutamate (NAAG) is a neuropeptide found in millimolar concentrations in brain that is localized to subpopulations of glutamatergic, cholinergic, GABAergic, and noradrenergic neuronal systems. NAAG is released upon depolarization by a Ca(2+)-dependent process and is an agonist at mGluR3 receptors and an antagonist at NMDA receptors. NAAG is catabolized to N-acetylaspartate and glutamate primarily by glutamate carboxypeptidase II, which is expressed on the extracellular surface of astrocytes. The levels of NAAG and the activity of carboxypeptidase II are altered in a regionally specific fashion in several neuropsychiatric disorders. (PMID 9361299)
D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
D009676 - Noxae > D009498 - Neurotoxins
D018926 - Anti-Allergic Agents
D020011 - Protective Agents
Spaglumic Acid (N-Acetylaspartylglutamic acid) is a neuropeptide found in millimolar concentrations in brain.

同义名列表

37 个代谢物同义名

(2S)-2-[(2S)-3-carboxy-2-acetamidopropanamido]pentanedioic acid; 2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid; N-(N-Acetyl-L-alpha-aspartyl)-L-glutamic acid; N-Acetyl-alpha-L-aspartyl-L-glutamic acid; N-Acetyl-L-alpha-aspartyl-L-glutamic acid; N-Acetyl-L-alpha-aspartylglutamic acid; N-Acetyl-α-L-aspartyl-L-glutamic acid; N-Acetyl-L-α-aspartyl-L-glutamic acid; N-Acetyl-a-L-aspartyl-L-glutamic acid; Acetyl-alpha-L-aspartylglutamic acid; N-Acetyl-alpha-aspartylglutamic acid; N-Acetyl-L-aspartyl-L-glutamic acid; N-(N-Acetylaspartyl)glutamic acid; Acetyl-a-L-aspartylglutamic acid; Acetyl-α-L-aspartylglutamic acid; N-Acetyl-α-aspartylglutamic acid; N-Acetyl-a-aspartylglutamic acid; N-Acetyl-1-aspartylglutamic acid; N-Acetyl-aspartyl-glutamic acid; N-acetyl-L-aspartyl-L-glutamate; N-Acetylaspartylglutamic acid; N-Acetyl-1-aspartylglutamate; N-Acetyl-aspartyl-glutamate; N-Acetylaspartylglutamate; alpha-Spaglumic acid; N-Acetyl-L-asp-L-glu; N-Acetyl-1-asp-glu; Isospaglumic acid; a-Spaglumic acid; Α-spaglumic acid; spaglumic acid; Isospaglumate; N-Ac-D-e; Naaxia; NAAGA; NAAG; N-Acetylaspartylglutamic acid (NAAG)



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

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)

1 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

  • František Sedlák, Aleš Kvasnička, Barbora Marešová, Radana Brumarová, Dana Dobešová, Kateřina Dostálová, Karolína Šrámková, Martin Pehr, Pavel Šácha, David Friedecký, Jan Konvalinka. Parallel Metabolomics and Lipidomics of a PSMA/GCPII Deficient Mouse Model Reveal Alteration of NAAG Levels and Brain Lipid Composition. ACS chemical neuroscience. 2024 Apr; 15(7):1342-1355. doi: 10.1021/acschemneuro.3c00494. [PMID: 38377674]
  • J R Swann, I Garcia-Perez, V Braniste, I D Wilson, J E Sidaway, J K Nicholson, S Pettersson, E Holmes. Application of 1H NMR spectroscopy to the metabolic phenotyping of rodent brain extracts: A metabonomic study of gut microbial influence on host brain metabolism. Journal of pharmaceutical and biomedical analysis. 2017 Sep; 143(?):141-146. doi: 10.1016/j.jpba.2017.05.040. [PMID: 28595107]
  • H Rosewich, P Dechent, C Krause, A Ohlenbusch, K Brockmann, J Gärtner. Diagnostic and prognostic value of in vivo proton MR spectroscopy for Zellweger syndrome spectrum patients. Journal of inherited metabolic disease. 2016 11; 39(6):869-876. doi: 10.1007/s10545-016-9965-6. [PMID: 27488561]
  • Devender Bairwa, Virendra Kumar, Surabhi Vyas, Bimal Kumar Das, Achal Kumar Srivastava, Ravinder M Pandey, Surendra K Sharma, Naranamangalam R Jagannathan, Sanjeev Sinha. Case control study: magnetic resonance spectroscopy of brain in HIV infected patients. BMC neurology. 2016 Jul; 16(?):99. doi: 10.1186/s12883-016-0628-x. [PMID: 27405321]
  • Ramandeep Garg, Lorraine Brennan, Ruth K Price, Julie M W Wallace, J J Strain, Mike J Gibney, Peter R Shewry, Jane L Ward, Lalit Garg, Robert W Welch. Using NMR-Based Metabolomics to Evaluate Postprandial Urinary Responses Following Consumption of Minimally Processed Wheat Bran or Wheat Aleurone by Men and Women. Nutrients. 2016 Feb; 8(2):96. doi: 10.3390/nu8020096. [PMID: 26901221]
  • Kohnosuke Kinoshita, Kotaro Arai, Kazuaki Kawaura, Tetsuaki Hiyoshi, Jun-ichi Yamaguchi. Development, validation, and application of a surrogate analyte method for determining N-acetyl-l-aspartyl-l-glutamic acid levels in rat brain, plasma, and cerebrospinal fluid. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Oct; 1003(?):1-11. doi: 10.1016/j.jchromb.2015.09.005. [PMID: 26386976]
  • Radka Tušková, Boris Lipták, Pavol Szomolányi, Oľga Vančová, Oľga Uličná, Zuzana Sumbalová, Jarmila Kucharská, Michal Dubovický, Siegfried Trattnig, Tibor Liptaj, Svatava Kašparová. Neuronal marker recovery after Simvastatin treatment in dementia in the rat brain: in vivo magnetic resonance study. Behavioural brain research. 2015 May; 284(?):257-64. doi: 10.1016/j.bbr.2015.02.016. [PMID: 25698600]
  • F Mochel, U F H Engelke, J Barritault, B Yang, N H McNeill, J N Thompson, A Vanderver, N I Wolf, M A Willemsen, F W Verheijen, F Seguin, R A Wevers, R Schiffmann. Elevated CSF N-acetylaspartylglutamate in patients with free sialic acid storage diseases. Neurology. 2010 Jan; 74(4):302-5. doi: 10.1212/wnl.0b013e3181cbcdc4. [PMID: 20101035]
  • Morris H Baslow, David N Guilfoyle. Are astrocytes the missing link between lack of brain aspartoacylase activity and the spongiform leukodystrophy in Canavan disease?. Neurochemical research. 2009 Sep; 34(9):1523-34. doi: 10.1007/s11064-009-9958-z. [PMID: 19319678]
  • Carolina Didonet Pederzolli, Francieli Juliana Rockenbach, Fernanda Rech Zanin, Nicoli Taiana Henn, Eline Coan Romagna, Angela M Sgaravatti, Angela T S Wyse, Clóvis M D Wannmacher, Moacir Wajner, Angela de Mattos Dutra, Carlos S Dutra-Filho. Intracerebroventricular administration of N-acetylaspartic acid impairs antioxidant defenses and promotes protein oxidation in cerebral cortex of rats. Metabolic brain disease. 2009 Jun; 24(2):283-98. doi: 10.1007/s11011-009-9137-6. [PMID: 19294497]
  • Dominick J O McIntyre, Rebecca A Charlton, Hugh S Markus, Franklyn A Howe. Long and short echo time proton magnetic resonance spectroscopic imaging of the healthy aging brain. Journal of magnetic resonance imaging : JMRI. 2007 Dec; 26(6):1596-606. doi: 10.1002/jmri.21198. [PMID: 17968966]
  • Laura M Gehl, Omar H Saab, Tomasz Bzdega, Barbara Wroblewska, Joseph H Neale. Biosynthesis of NAAG by an enzyme-mediated process in rat central nervous system neurons and glia. Journal of neurochemistry. 2004 Aug; 90(4):989-97. doi: 10.1111/j.1471-4159.2004.02578.x. [PMID: 15287905]
  • G Tsai, K S Dunham, U Drager, A Grier, C Anderson, J Collura, J T Coyle. Early embryonic death of glutamate carboxypeptidase II (NAALADase) homozygous mutants. Synapse (New York, N.Y.). 2003 Dec; 50(4):285-92. doi: 10.1002/syn.10263. [PMID: 14556233]
  • C Blondin, B Cholley, N Haeffner-Cavaillon, P Goldschmidt. [In vitro effects of antiallergic eyedrops on complement activation induced by particulate matter]. Journal francais d'ophtalmologie. 2003 Apr; 26(4):328-36. doi: . [PMID: 12843888]
  • Hanna Krawczyk, Wanda Gradowska. Characterisation of the 1H and 13C NMR spectra of N-acetylaspartylglutamate and its detection in urine from patients with Canavan disease. Journal of pharmaceutical and biomedical analysis. 2003 Mar; 31(3):455-63. doi: 10.1016/s0731-7085(02)00691-x. [PMID: 12615232]
  • Dean J Bacich, Epolia Ramadan, Denise S O'Keefe, Noreen Bukhari, Iga Wegorzewska, Olumide Ojeifo, Rafal Olszewski, Craige C Wrenn, Tomasz Bzdega, Barbara Wroblewska, Warren D W Heston, Joseph H Neale. Deletion of the glutamate carboxypeptidase II gene in mice reveals a second enzyme activity that hydrolyzes N-acetylaspartylglutamate. Journal of neurochemistry. 2002 Oct; 83(1):20-9. doi: 10.1046/j.1471-4159.2002.01117.x. [PMID: 12358725]
  • Lioudmila Pliss, Daniela Jezová, Vladislav Mares, Vladimir J Balcar, Frantisek St'astný. N-Acetyl-L-aspartyl-L-glutamate changes functional and structural properties of rat blood-brain barrier. Neuroscience letters. 2002 Jan; 317(2):85-8. doi: 10.1016/s0304-3940(01)02423-5. [PMID: 11755246]
  • A P Burlina, V Ferrari, P Divry, W Gradowska, C Jakobs, M J Bennett, A C Sewell, C Dionisi-Vici, A B Burlina. N-acetylaspartylglutamate in Canavan disease: an adverse effector?. European journal of pediatrics. 1999 May; 158(5):406-9. doi: 10.1007/s004310051102. [PMID: 10333125]
  • H Wang, Y J Fei, V Ganapathy, F H Leibach. Electrophysiological characteristics of the proton-coupled peptide transporter PEPT2 cloned from rat brain. The American journal of physiology. 1998 10; 275(4):C967-75. doi: 10.1152/ajpcell.1998.275.4.c967. [PMID: 9755050]
  • G Tsai, D C Goff, R W Chang, J Flood, L Baer, J T Coyle. Markers of glutamatergic neurotransmission and oxidative stress associated with tardive dyskinesia. The American journal of psychiatry. 1998 Sep; 155(9):1207-13. doi: 10.1176/ajp.155.9.1207. [PMID: 9734544]
  • B Wroblewska, J T Wroblewski, S Pshenichkin, A Surin, S E Sullivan, J H Neale. N-acetylaspartylglutamate selectively activates mGluR3 receptors in transfected cells. Journal of neurochemistry. 1997 Jul; 69(1):174-81. doi: 10.1046/j.1471-4159.1997.69010174.x. [PMID: 9202308]
  • A P Burlina, A Corazza, V Ferrari, P Erhard, B Künnecke, J Seelig, A B Burlina. Detection of increased urinary N-acetylaspartylglutamate in Canavan disease. European journal of pediatrics. 1994 Jul; 153(7):538-9. doi: 10.1007/bf01957015. [PMID: 7957376]
  • P B Toft, P Christiansen, O Pryds, H C Lou, O Henriksen. T1, T2, and concentrations of brain metabolites in neonates and adolescents estimated with H-1 MR spectroscopy. Journal of magnetic resonance imaging : JMRI. 1994 Jan; 4(1):1-5. doi: 10.1002/jmri.1880040102. [PMID: 7908545]
  • M Cassidy, J H Neale. N-acetylaspartylglutamate catabolism is achieved by an enzyme on the cell surface of neurons and glia. Neuropeptides. 1993 May; 24(5):271-8. doi: 10.1016/0143-4179(93)90015-3. [PMID: 8100987]
  • J R Moffett, M A Namboodiri, J H Neale. Enhanced carbodiimide fixation for immunohistochemistry: application to the comparative distributions of N-acetylaspartylglutamate and N-acetylaspartate immunoreactivities in rat brain. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society. 1993 Apr; 41(4):559-70. doi: 10.1177/41.4.8450195. [PMID: 8450195]
  • A Plaitakis, E Constantakakis. Altered metabolism of excitatory amino acids, N-acetyl-aspartate and N-acetyl-aspartyl-glutamate in amyotrophic lateral sclerosis. Brain research bulletin. 1993; 30(3-4):381-6. doi: 10.1016/0361-9230(93)90269-h. [PMID: 8457887]
  • B S Slusher, G Tsai, G Yoo, J T Coyle. Immunocytochemical localization of the N-acetyl-aspartyl-glutamate (NAAG) hydrolyzing enzyme N-acetylated alpha-linked acidic dipeptidase (NAALADase). The Journal of comparative neurology. 1992 Jan; 315(2):217-29. doi: 10.1002/cne.903150208. [PMID: 1545010]
  • C G Frondoza, S Logan, G Forloni, J T Coyle. Production and characterization of monoclonal antibodies to N-acetyl-aspartyl-glutamate. The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society. 1990 Apr; 38(4):493-502. doi: 10.1177/38.4.2319120. [PMID: 2319120]
  • B Datz, C Sieger, M A Weibel. [NAAGA and cromoglycate. A comparison in the treatment of seasonal allergic rhinitis]. Laryngologie, Rhinologie, Otologie. 1988 Jun; 67(6):300-3. doi: . [PMID: 3136279]
  • A S Guarda, M B Robinson, L Ory-Lavollée, G L Forloni, R D Blakely, J T Coyle. Quantitation of N-acetyl-aspartyl-glutamate in microdissected rat brain nuclei and peripheral tissues: findings with a novel liquid phase radioimmunoassay. Brain research. 1988 Jun; 427(3):223-31. doi: 10.1016/0169-328x(88)90045-9. [PMID: 3401700]
  • R D Blakely, M B Robinson, R C Thompson, J T Coyle. Hydrolysis of the brain dipeptide N-acetyl-L-aspartyl-L-glutamate: subcellular and regional distribution, ontogeny, and the effect of lesions on N-acetylated-alpha-linked acidic dipeptidase activity. Journal of neurochemistry. 1988 Apr; 50(4):1200-9. doi: 10.1111/j.1471-4159.1988.tb10593.x. [PMID: 3346674]
  • M B Robinson, R D Blakely, R Couto, J T Coyle. Hydrolysis of the brain dipeptide N-acetyl-L-aspartyl-L-glutamate. Identification and characterization of a novel N-acetylated alpha-linked acidic dipeptidase activity from rat brain. The Journal of biological chemistry. 1987 Oct; 262(30):14498-506. doi: . [PMID: 3667587]
  • L Ory-Lavollée, R D Blakely, J T Coyle. Neurochemical and immunocytochemical studies on the distribution of N-acetyl-aspartylglutamate and N-acetyl-aspartate in rat spinal cord and some peripheral nervous tissues. Journal of neurochemistry. 1987 Mar; 48(3):895-9. doi: 10.1111/j.1471-4159.1987.tb05601.x. [PMID: 3543223]
  • R D Blakely, L Ory-Lavollée, R Grzanna, K J Koller, J T Coyle. Selective immunocytochemical staining of mitral cells in rat olfactory bulb with affinity purified antibodies against N-acetyl-aspartyl-glutamate. Brain research. 1987 Feb; 402(2):373-8. doi: 10.1016/0006-8993(87)90049-7. [PMID: 2435366]
  • P Lapalus, G Moulin, V Bayer, D Fredj-Reygrobellet, P P Elena. Effects of a new anti-allergic agent: the magnesium salt of N-acetyl-aspartyl-glutamic acid on experimental allergic inflammation of the rabbit eye. Current eye research. 1986 Jul; 5(7):517-22. doi: 10.3109/02713688608996374. [PMID: 3743112]
  • S Tsuji, K Nakagawa, T Fukushima. Genetically controlled quantitative variation of ornithine transcarbamylase in the chick kidney. Biochemical genetics. 1983 Oct; 21(9-10):857-69. doi: 10.1007/bf00483945. [PMID: 6419722]
  • M Miyake, H Morino, M Mizobuchi, Y Kakimoto. N-acetyl-L-aspartic acid, N-acetyl-alpha-L-aspartyl-L-glutamic acid and beta-citryl-L-glutamic acid in human urine. Clinica chimica acta; international journal of clinical chemistry. 1982 Mar; 120(1):119-26. doi: 10.1016/0009-8981(82)90082-1. [PMID: 7067131]
  • H H Borden, R W Harris, W E Mosher. A waterborne outbreak of gastroenteritis in western New York State. American journal of public health and the nation's health. 1970 Feb; 60(2):283-8. doi: 10.2105/ajph.60.2.283. [PMID: 5460971]