Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:22:34 UTC |
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NP-MRD ID | NP0001328 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Glutarylglycine |
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Description | Glutarylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) Which is an enzyme that catalyzes the chemical reaction:. Acyl-CoA + glycine < -- > CoA + N-acylglycine. Glutarylglycine is involved in lysine metabolism. An elevated level of glutarylglycine occurs in patients with glutaric acidemia type II, which is an autosomal recessive inborn error of metabolism due to a mitochondrial respiratory electron chain transport defect. (Http://Www.Pediatricneuro.Com/alfonso/pg75.Htm). |
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Structure | InChI=1S/C7H11NO5/c9-5(8-4-7(12)13)2-1-3-6(10)11/h1-4H2,(H,8,9)(H,10,11)(H,12,13) |
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Synonyms | Value | Source |
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5-[(Carboxymethyl)amino]-5-oxo-pentanoate | HMDB | 5-[(Carboxymethyl)amino]-5-oxo-pentanoic acid | HMDB | N-(Carboxymethyl)-glutaramic acid | HMDB | 4-[(Carboxymethyl)-C-hydroxycarbonimidoyl]butanoate | HMDB |
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Chemical Formula | C7H11NO5 |
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Average Mass | 189.1659 Da |
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Monoisotopic Mass | 189.06372 Da |
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IUPAC Name | 4-[(carboxymethyl)carbamoyl]butanoic acid |
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Traditional Name | 4-(carboxymethylcarbamoyl)butanoic acid |
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CAS Registry Number | 17686-38-3 |
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SMILES | OC(=O)CCCC(=O)NCC(O)=O |
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InChI Identifier | InChI=1S/C7H11NO5/c9-5(8-4-7(12)13)2-1-3-6(10)11/h1-4H2,(H,8,9)(H,10,11)(H,12,13) |
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InChI Key | NBLKTRLPZFCMJG-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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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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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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
- Dicarboxylic acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Fatty acid
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Carbonyl group
- Organonitrogen compound
- Organooxygen 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 | Not Available |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Ohie T, Fu X, Iga M, Kimura M, Yamaguchi S: Gas chromatography-mass spectrometry with tert.-butyldimethylsilyl derivation: use of the simplified sample preparations and the automated data system to screen for organic acidemias. J Chromatogr B Biomed Sci Appl. 2000 Sep 1;746(1):63-73. [PubMed:11048741 ]
- Gron I, Gregersen N, Kolvraa S, Rasmussen K: Formation of N-dicarboxyl-mono-glycines catalyzed by glycine-N-acylase. Biochem Med. 1978 Feb;19(1):133-48. [PubMed:623642 ]
- Gregersen N, Kolvraa S, Rasmussen K, Gron I: Demonstration of N-dicarboxyl-mono-glycines in dicarboxylic acidurias by mass fragmentography. Clin Chim Acta. 1977 Jul 15;78(2):173-82. [PubMed:884855 ]
- Bonafe L, Troxler H, Kuster T, Heizmann CW, Chamoles NA, Burlina AB, Blau N: Evaluation of urinary acylglycines by electrospray tandem mass spectrometry in mitochondrial energy metabolism defects and organic acidurias. Mol Genet Metab. 2000 Apr;69(4):302-11. [PubMed:10870848 ]
- Gregersen N, Gron I, Rasmussen K, Kolvraa S: Gas chromatographic mass spectrometric identification of N-dicarboxylmonoglycines. Biomed Mass Spectrom. 1978 Jan;5(1):80-3. [PubMed:623898 ]
- (). Asai, Kiyofumi. Urinary glutarylglycine in a patient with glutaric aciduria type I. Quantification of urinary glutarylglycine by a carboxylic acid analyzer and its clinical application. Nagoya-shiritsu Daigaku Igakkai Zasshi (1989), 40(4), 743-58. .
- (). Curtius, T., Hechtenberg, Wihelm. Synthesis of -aminobutyric acid from glutarylglycine ester. Journal fuer Praktische Chemie (Leipzig) (1923), 105 319-26. .
- (). Fujita, A. Synthesis of anemoninic acid. Yakugaku Zasshi (1923), No. 492 67-75. .
- (). Paul, L., Dittmar, A., Rusch, Christel. Synthesis of maleoyl- and glutarylglycyl chlorides. Chemische Berichte (1967), 100(8), 2757-60. .
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