Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2014-04-16 20:46:48 UTC |
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Update Date | 2023-02-21 17:30:26 UTC |
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HMDB ID | HMDB0061715 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Glutamic acid gamma-methyl ester |
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Description | L-Glutamic acid 5-methyl ester, also known as poly(gamma-methyl L-glutamate) or PGMGT, belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Glutamic acid 5-methyl ester is a very strong basic compound (based on its pKa). |
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Structure | InChI=1S/C6H11NO4/c1-11-5(8)3-2-4(7)6(9)10/h4H,2-3,7H2,1H3,(H,9,10)/t4-/m0/s1 |
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Synonyms | Value | Source |
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L-Glutamate 5-methyl ester | Generator | PGMGT | MeSH | Poly-gamma-methylglutamic acid | MeSH | Poly(gamma-methyl L-glutamate) | MeSH | Poly-gamma-methylglutamate | MeSH | PMLG Polymer | MeSH | Poly(gamma-methyl-L-glutamate) | MeSH | (2S)-2-Amino-5-methoxy-5-oxopentanoate | Generator | (2S)-2-Amino-5-methoxy-5-oxo-pentanoic acid | HMDB | (S)-2-Aminopentanedioic acid 5-methyl ester | HMDB | (S)-Glutamic acid 5-methyl ester | HMDB | 4(S)-Carboxy-4-aminobutanoic acid methyl ester | HMDB | 5-Methyl L-glutamate | HMDB | Glutamate gamma-methyl ester | HMDB | Glutamate γ-methyl ester | HMDB | Glutamic acid 5-methyl ester | HMDB | L-Glutamic acid gamma-methyl ester | HMDB | L-Glutamic acid γ-methyl ester | HMDB | gamma-Methyl (S)-glutamate | HMDB | gamma-Methyl L-glutamate | HMDB | γ-Methyl (S)-glutamate | HMDB | γ-Methyl L-glutamate | HMDB |
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Chemical Formula | C6H11NO4 |
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Average Molecular Weight | 161.1558 |
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Monoisotopic Molecular Weight | 161.068807845 |
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IUPAC Name | (2S)-2-amino-5-methoxy-5-oxopentanoic acid |
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Traditional Name | (2S)-2-amino-5-methoxy-5-oxopentanoic acid |
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CAS Registry Number | 1499-55-4 |
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SMILES | COC(=O)CC[C@H](N)C(O)=O |
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InChI Identifier | InChI=1S/C6H11NO4/c1-11-5(8)3-2-4(7)6(9)10/h4H,2-3,7H2,1H3,(H,9,10)/t4-/m0/s1 |
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InChI Key | ZGEYCCHDTIDZAE-BYPYZUCNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Glutamic acid and derivatives |
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Alternative Parents | |
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Substituents | - Glutamic acid or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Fatty acid ester
- Fatty acid methyl ester
- Dicarboxylic acid or derivatives
- Fatty acyl
- Methyl ester
- Carboxylic acid ester
- Amino acid
- Carboxylic acid
- Organic nitrogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Glutamic acid gamma-methyl ester,1TMS,isomer #1 | COC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C | 1399.5 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,1TMS,isomer #2 | COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O | 1499.6 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TMS,isomer #1 | COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1528.3 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TMS,isomer #1 | COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1555.4 | Standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TMS,isomer #1 | COC(=O)CC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1896.0 | Standard polar | 33892256 | Glutamic acid gamma-methyl ester,2TMS,isomer #2 | COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1687.0 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TMS,isomer #2 | COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1621.1 | Standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TMS,isomer #2 | COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2092.1 | Standard polar | 33892256 | Glutamic acid gamma-methyl ester,3TMS,isomer #1 | COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1718.9 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,3TMS,isomer #1 | COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1671.7 | Standard non polar | 33892256 | Glutamic acid gamma-methyl ester,3TMS,isomer #1 | COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1836.4 | Standard polar | 33892256 | Glutamic acid gamma-methyl ester,1TBDMS,isomer #1 | COC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C | 1629.7 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,1TBDMS,isomer #2 | COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O | 1742.2 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TBDMS,isomer #1 | COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1964.7 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TBDMS,isomer #1 | COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1995.4 | Standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TBDMS,isomer #1 | COC(=O)CC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2125.6 | Standard polar | 33892256 | Glutamic acid gamma-methyl ester,2TBDMS,isomer #2 | COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2120.4 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TBDMS,isomer #2 | COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2051.1 | Standard non polar | 33892256 | Glutamic acid gamma-methyl ester,2TBDMS,isomer #2 | COC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2218.2 | Standard polar | 33892256 | Glutamic acid gamma-methyl ester,3TBDMS,isomer #1 | COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2379.3 | Semi standard non polar | 33892256 | Glutamic acid gamma-methyl ester,3TBDMS,isomer #1 | COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2292.4 | Standard non polar | 33892256 | Glutamic acid gamma-methyl ester,3TBDMS,isomer #1 | COC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2195.7 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Glutamic acid gamma-methyl ester GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glutamic acid gamma-methyl ester GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 10V, Positive-QTOF | splash10-02ai-2900000000-e25e7bd0169fa84c265a | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Positive-QTOF | splash10-014j-9700000000-b2707dfbecef89dccc36 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Positive-QTOF | splash10-0a4i-9000000000-ef9d7dadc9a20b25c7b7 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 10V, Negative-QTOF | splash10-03di-0900000000-9ca60a4a29b53180d21f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Negative-QTOF | splash10-03fr-3900000000-deb73cb97bd1b4d6f62d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Negative-QTOF | splash10-00ec-9200000000-e28dba9ace5235f5f94d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 10V, Negative-QTOF | splash10-01tc-1900000000-7ba8da19d1ca271d51a8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Negative-QTOF | splash10-0gx3-6900000000-437a04a8632b8b96a54c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Negative-QTOF | splash10-0006-9000000000-60f58cdb95258ba389a3 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 10V, Positive-QTOF | splash10-02u9-5900000000-2d2de75bccd5007f24e1 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 20V, Positive-QTOF | splash10-00lj-9100000000-fac61cb106b5271040ea | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glutamic acid gamma-methyl ester 40V, Positive-QTOF | splash10-0a4i-9000000000-677484e9a6c9c097bacc | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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General References | - Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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