Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:30:23 UTC |
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Update Date | 2023-02-21 17:18:46 UTC |
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HMDB ID | HMDB0029433 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-2-Amino-4-methylenepentanedioic acid |
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Description | L-2-Amino-4-methylenepentanedioic acid, also known as 4-methylene-DL-glutamic acid or (2S,3S)-(3-2H1)-4-methyleneglutamic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review a significant number of articles have been published on L-2-Amino-4-methylenepentanedioic acid. |
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Structure | InChI=1S/C6H9NO4/c1-3(5(8)9)2-4(7)6(10)11/h4H,1-2,7H2,(H,8,9)(H,10,11) |
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Synonyms | Value | Source |
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4-Methylene-DL-glutamic acid | ChEBI | gamma-Methylene glutamic acid | ChEBI | 4-Methylene-DL-glutamate | Generator | g-Methylene glutamate | Generator | g-Methylene glutamic acid | Generator | gamma-Methylene glutamate | Generator | Γ-methylene glutamate | Generator | Γ-methylene glutamic acid | Generator | L-2-Amino-4-methylenepentanedioate | Generator | 4-Methylene glutamic acid | HMDB | 4-Methylene-L-glutamate | HMDB | 4-Methylidene glutamic acid | HMDB | 4-Methyleneglutamate | HMDB | (2S,3S)-(3-2H1)-4-Methyleneglutamic acid | HMDB | 4-Methyleneglutamic acid, (L-glu)-isomer | HMDB | 4-Methyleneglutamic acid, sodium salt, (L-glu)-isomer | HMDB | (2S,3R)-(2,3-2H2)-4-Methyleneglutamic acid | HMDB | 4-Methyleneglutamic acid | HMDB |
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Chemical Formula | C6H9NO4 |
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Average Molecular Weight | 159.14 |
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Monoisotopic Molecular Weight | 159.053157781 |
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IUPAC Name | 2-amino-4-methylidenepentanedioic acid |
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Traditional Name | 4-methyleneglutamic acid |
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CAS Registry Number | 16804-57-2 |
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SMILES | NC(CC(=C)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C6H9NO4/c1-3(5(8)9)2-4(7)6(10)11/h4H,1-2,7H2,(H,8,9)(H,10,11) |
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InChI Key | RCCMXKJGURLWPB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). |
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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 | Alpha amino acids |
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Alternative Parents | |
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Substituents | - Alpha-amino acid
- Amino fatty acid
- Branched fatty acid
- Dicarboxylic acid or derivatives
- Fatty acyl
- Fatty acid
- Unsaturated fatty acid
- Amino acid
- Carboxylic acid
- Organic nitrogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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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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L-2-Amino-4-methylenepentanedioic acid,1TMS,isomer #1 | C=C(CC(N)C(=O)O)C(=O)O[Si](C)(C)C | 1493.6 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,1TMS,isomer #2 | C=C(CC(N)C(=O)O[Si](C)(C)C)C(=O)O | 1535.2 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,1TMS,isomer #3 | C=C(CC(N[Si](C)(C)C)C(=O)O)C(=O)O | 1607.5 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TMS,isomer #1 | C=C(CC(N)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1567.0 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TMS,isomer #2 | C=C(CC(N[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C | 1643.7 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TMS,isomer #3 | C=C(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O | 1635.2 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TMS,isomer #4 | C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 1813.1 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TMS,isomer #1 | C=C(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1661.5 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TMS,isomer #1 | C=C(CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1691.8 | Standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TMS,isomer #2 | C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1816.9 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TMS,isomer #2 | C=C(CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1781.8 | Standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TMS,isomer #3 | C=C(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 1819.5 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TMS,isomer #3 | C=C(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 1695.6 | Standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,4TMS,isomer #1 | C=C(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1843.1 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,4TMS,isomer #1 | C=C(CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1806.7 | Standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,1TBDMS,isomer #1 | C=C(CC(N)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C | 1728.1 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,1TBDMS,isomer #2 | C=C(CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O | 1784.0 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,1TBDMS,isomer #3 | C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O | 1845.4 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TBDMS,isomer #1 | C=C(CC(N)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1993.2 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TBDMS,isomer #2 | C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C | 2073.6 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TBDMS,isomer #3 | C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O | 2084.7 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,2TBDMS,isomer #4 | C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2220.7 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TBDMS,isomer #1 | C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2281.8 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TBDMS,isomer #1 | C=C(CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2282.0 | Standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TBDMS,isomer #2 | C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2452.3 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TBDMS,isomer #2 | C=C(CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2332.8 | Standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TBDMS,isomer #3 | C=C(CC(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)C(=O)O | 2480.3 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,3TBDMS,isomer #3 | C=C(CC(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)C(=O)O | 2325.0 | Standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,4TBDMS,isomer #1 | C=C(CC(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)C(=O)O[Si](C)(C)C(C)(C)C | 2668.9 | Semi standard non polar | 33892256 | L-2-Amino-4-methylenepentanedioic acid,4TBDMS,isomer #1 | C=C(CC(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)C(=O)O[Si](C)(C)C(C)(C)C | 2558.8 | Standard non 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 - L-2-Amino-4-methylenepentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-044l-9300000000-4bf971e6eda33854899b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-2-Amino-4-methylenepentanedioic acid GC-MS (2 TMS) - 70eV, Positive | splash10-05fu-8290000000-937029406411ff8ce3f4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 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 - L-2-Amino-4-methylenepentanedioic acid 10V, Positive-QTOF | splash10-03di-3900000000-fcf669094a0ee94356d7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 20V, Positive-QTOF | splash10-03xs-9500000000-10e17e660bf63bacae45 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 40V, Positive-QTOF | splash10-014i-9000000000-586fe67eaca3bc48cc6a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 10V, Negative-QTOF | splash10-0a4i-1900000000-59c4ae04e470fbdf819e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 20V, Negative-QTOF | splash10-074r-9700000000-914712eca23ff94b0002 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 40V, Negative-QTOF | splash10-00di-9000000000-dc78f41c92a36f9a6acd | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 10V, Negative-QTOF | splash10-0bt9-1900000000-e90f6ef1558e6858387d | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 20V, Negative-QTOF | splash10-03ka-9400000000-2ce1140f2a1b29aa46cc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 40V, Negative-QTOF | splash10-0006-9000000000-fc42333b630baebe7a73 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 10V, Positive-QTOF | splash10-03kd-5900000000-9e2cbd8f98cadd3a911f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 20V, Positive-QTOF | splash10-01b9-9000000000-5ce6d9bc7f9594547785 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-2-Amino-4-methylenepentanedioic acid 40V, Positive-QTOF | splash10-014i-9000000000-25de33acb3932f7ce578 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | 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]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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