Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:17:44 UTC |
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NP-MRD ID | NP0000716 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Acetylglycine |
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Description | N-acetylglycine is used is in biological research of peptidomimetics. It is used as the blocking agent of the N-terminus to prepare unnatural and unusual amino acids and amino acid analogs as well as to modify peptides. N-Substituted glycine analogs are widely used in peptidomimetics and drug research. Excessive amounts N-acetyl amino acids including N-acetylglycine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, Nacetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine) can be detected in the urine with individuals with acylase I defiency, a genetic disorder. This enzyme is involved in the degradation of N-acylated proteins. Individuals with this disorder will experience convulsions, hearing loss ond difficulty feeding. |
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Structure | InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8) |
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Synonyms | Value | Source |
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Ac-gly-OH | ChEBI | Acetamidoacetic acid | ChEBI | Aceturic acid | ChEBI | Acetylamino-acetic acid | ChEBI | Acetylaminoacetic acid | ChEBI | Ethanoylaminoethanoic acid | ChEBI | Acetamidoacetate | Generator | Acetate | Generator | Acetic acid | Generator | Acetylamino-acetate | Generator | Acetylaminoacetate | Generator | Ethanoylaminoethanoate | Generator | 15N-Acetylglycine a-radical | HMDB | 2-Acetamidoacetate | HMDB | 2-Acetamidoacetic acid | HMDB | Ac gly | HMDB | Aceturate | HMDB | Acetylglycocoll | HMDB | N-Acetyl-glycine | HMDB | N-Acetylglycine | HMDB | N-Acetylglycine sodium salt | HMDB | Acetylglycinate | HMDB | Acetylglycine | ChEBI |
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Chemical Formula | C4H7NO3 |
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Average Mass | 117.1033 Da |
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Monoisotopic Mass | 117.04259 Da |
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IUPAC Name | 2-acetamidoacetic acid |
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Traditional Name | aceturate |
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CAS Registry Number | 543-24-8 |
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SMILES | CC(=O)NCC(O)=O |
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InChI Identifier | InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8) |
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InChI Key | OKJIRPAQVSHGFK-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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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
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 207 - 209 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 26.3 mg/mL at 15 °C | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Graca G, Duarte IF, J Goodfellow B, Carreira IM, Couceiro AB, Domingues Mdo R, Spraul M, Tseng LH, Gil AM: Metabolite profiling of human amniotic fluid by hyphenated nuclear magnetic resonance spectroscopy. Anal Chem. 2008 Aug 1;80(15):6085-92. doi: 10.1021/ac800907f. Epub 2008 Jun 20. [PubMed:18564856 ]
- Harper MS, Shen ZA, Barnett JF Jr, Krsmanovic L, Dakoulas EW, Delaney B: Toxicology studies with N-acetylglycine. Food Chem Toxicol. 2010 May;48(5):1321-7. doi: 10.1016/j.fct.2010.02.031. Epub 2010 Feb 25. [PubMed:20188778 ]
- Manna SK, Patterson AD, Yang Q, Krausz KW, Idle JR, Fornace AJ, Gonzalez FJ: UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. J Proteome Res. 2011 Sep 2;10(9):4120-33. doi: 10.1021/pr200310s. Epub 2011 Jul 28. [PubMed:21749142 ]
- Boeckx B, Maes G: Comparison of the conformational behavior of amino acids and N-acetylated amino acids: a theoretical and matrix-isolation FT-IR study of N-acetylglycine. J Phys Chem A. 2012 Mar 1;116(8):1956-65. doi: 10.1021/jp211382u. Epub 2012 Feb 21. [PubMed:22273063 ]
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