N-acetyltyrosine (BioDeep_00000017795)

 

Secondary id: BioDeep_00000405387, BioDeep_00000604243

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoic acid

化学式: C11H13NO4 (223.0844538)
中文名称: N-乙酰基-DL-酪氨酸, N-乙酰-L-酪氨酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.06%

Reviewed

Last reviewed on 2024-09-13.

Cite this Page

N-acetyltyrosine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/n-acetyltyrosine (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000017795). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=O)NC(CC1=CC=C(C=C1)O)C(=O)O
InChI: InChI=1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)

描述信息

N-Acetyl-L-tyrosine or N-Acetyltyrosine, 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-Acetyltyrosine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetyltyrosine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-tyrosine. 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-acetyltyrosine 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 tyrosine can also occur. Many N-acetylamino acids, including N-acetyltyrosine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986; PMID: 20613759). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557). N-Acetyl-L-tyrosine, has also been associated with several inborn metabolic disorders including tyrosinemia I and aromatic l-amino acid decarboxylase deficiency. N-acetyltyrosine, is used in place of as a tyrosine precursor and administered as a source of nutritional support where oral nutrition is inadequate or cannot be tolerated (PMID: 14621123). N-acetyltyrosine has also been identified as an endogenous stress response factor. Under stress conditions, mitochondria release low levels of reactive oxygen species (ROS), which triggers a cytoprotective response, called "mitohormesis". N-acetyltyrosine has recently been identified as an intrinsic triggering factor of mitohormesis in stressed animals (PMID: 32118349). Interventions and small molecules, which promote formation of reactive oxygen species (ROS), have been shown to increase stress resistance and lifespan of different model organisms. These phenotypes occur only in response to low concentrations of ROS, while higher concentrations of ROS exert opposing effects. In this regard, a stress-dependent increase in N-acetyltyrosine was recently found to occur in insect larvae that had endured high temperatures (i.e. thermal stress). N-acetyltyrosine treatment has also been demonstrated to induce thermotolerance in several tested insect species. N-acetyltyrosine has been identified in the serum of humans as well as mice, and its concentration in mice was shown to be increased by heat s...
Acetyltyrosine is a side chain reaction of tyrosine. It converts to tyrosine and then can be used in neurotransmitter treatment as a precursor of cathecholamine (http://www.neuroassist.com/). [HMDB]
N-Acetyl-L-tyrosine originates from tyrosine through an AA acetylase, is associated with aromatic L-amino acid decarboxylase deficiency and tyrosinemia I.

同义名列表

13 个代谢物同义名

(2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid; (2S)-2-Acetylamino-3-(4-hydroxyphenyl)propanoate; N-Acetyl-4-hydroxyphenylalanine; N-Acetyltyrosine, (DL)-isomer; N-Acetyltyrosine, (D)-isomer; L-N-acetyl-Tyrosine; N-Acetyl-L-tyrosine; L-N-Acetyltyrosine; Acetyl-L-tyrosine; N-Acetyl-tyrosine; N-Acetyltyrosine; N-Acetyl-L-tyrosine



数据库引用编号

14 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)

2 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

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  • Yoji Kato, Natsuko Dozaki, Toshiyuki Nakamura, Noritoshi Kitamoto, Akihiro Yoshida, Michitaka Naito, Masayasu Kitamura, Toshihiko Osawa. Quantification of Modified Tyrosines in Healthy and Diabetic Human Urine using Liquid Chromatography/Tandem Mass Spectrometry. Journal of clinical biochemistry and nutrition. 2009 Jan; 44(1):67-78. doi: 10.3164/jcbn.08-185. [PMID: 19177191]
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  • Jose E Abdenur, Nico Abeling, Norma Specola, Lia Jorge, Andrea B Schenone, Arno C van Cruchten, Nestor A Chamoles. Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Molecular genetics and metabolism. 2006 Jan; 87(1):48-53. doi: 10.1016/j.ymgme.2005.09.007. [PMID: 16288991]
  • Stanley H Korman, Alisa Gutman. N-acetyl tyrosyluria caused by parenteral or enteral administration of N-acetyl-L-tyrosine: differentiation from hereditary and acquired tyrosinemias. Journal of pediatric gastroenterology and nutrition. 2004 Jul; 39(1):95-100. doi: 10.1097/00005176-200407000-00019. [PMID: 15187789]
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  • T Shutova, A Villarejo, B Zietz, V Klimov, T Gillbro, G Samuelsson, G Renger. Comparative studies on the properties of the extrinsic manganese-stabilizing protein from higher plants and of a synthetic peptide of its C-terminus. Biochimica et biophysica acta. 2003 Jun; 1604(2):95-104. doi: 10.1016/s0005-2728(03)00025-2. [PMID: 12765766]
  • Do Kyung Kim, Yoshikatsu Kanai, Hirotaka Matsuo, Ju Young Kim, Arthit Chairoungdua, Yukari Kobayashi, Atsushi Enomoto, Seok Ho Cha, Tomoyuki Goya, Hitoshi Endou. The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan; 79(1):95-103. doi: 10.1006/geno.2001.6678. [PMID: 11827462]
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