Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:47 UTC |
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Update date | 2019-11-26 02:55:42 UTC |
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Primary ID | FDB000970 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | N-Acetyl-L-serine |
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Description | Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians,80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. Acetylation of the N-terminal amino acid (-NH2 acetylation) is a common protein modification in eukaryotes but is rarely encountered in prokaryotes. In mammalians, 80 to 90 percent of the cytosolic proteins are subjected to an irreversible, cotranslational amino acid acetylation at their N-terminus. N-acetylated proteins are catabolized in the cytosol by the ATP-ubiquitin-dependent proteasomal pathway. Several types of aminoacylases can be distinguished on the basis of substrate specificity. Aminoacylase I (ACY1; EC 3.5.1.14), the most abundant type, is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. It is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that comprises 15 exons (OMIM 609924). Preferred substrates of ACY1 are aliphatic amino acids with a short-chain acyl moiety, especially N-acetyl-methionine. However, ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Functional aminoacylase I is crucial in the last step in this degradation as it catalyzes the hydrolysis of N-acetylated amino acids into acetate and the free amino acid. Although N-acetylation occurs in many metabolic pathways and N-acetylated metabolites are known to accumulate in several inborn errors, there are only a few reports on N-acetylated amino acids detected in urine. Identification of N-acetylated amino acids by routine GC-MS may be problematic for several reasons. The major problem is linked to the identification strategy itself. Identification of an unknown compound in mass spectrometry is usually based on comparison of its spectrum against a library of reference spectra. (PMID: 16465618, 16274666, 17723438). N-Acetyl-L-serine is found in watermelon. |
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CAS Number | 16354-58-8 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C5H9NO4 |
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IUPAC name | 2-acetamido-3-hydroxypropanoic acid |
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InChI Identifier | InChI=1S/C5H9NO4/c1-3(8)6-4(2-7)5(9)10/h4,7H,2H2,1H3,(H,6,8)(H,9,10) |
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InChI Key | JJIHLJJYMXLCOY-UHFFFAOYSA-N |
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Isomeric SMILES | CC(=O)NC(CO)C(O)=O |
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Average Molecular Weight | 147.1293 |
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Monoisotopic Molecular Weight | 147.053157781 |
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Classification |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-alpha amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-amino acid
- Serine or derivatives
- Beta-hydroxy acid
- Hydroxy acid
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen compound
- Primary alcohol
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | N-Acetyl-L-serine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9200000000-3fdf2264d7f6bfa966ae | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f7k-1900000000-8fd08db8763ca780a73b | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0nn9-9500000000-5ed0dd34b41fd175f669 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9100000000-2e1c11fb421c1111b011 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-2900000000-0c8c866ca02199eba95d | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zgj-9800000000-fb156ef161572da8f131 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9100000000-a9df8ace176575dd53e5 | 2016-09-12 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 58744 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 65249 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02340 |
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HMDB ID | HMDB02931 |
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CRC / DFC (Dictionary of Food Compounds) ID | BCP29-I:BOF42-P |
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EAFUS ID | Not Available |
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Dr. Duke ID | N-ACETYL-SERINE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | SAC |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Acetylserine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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