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 17:30:21 UTC |
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Update Date | 2022-03-07 02:52:09 UTC |
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HMDB ID | HMDB0029427 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Hypoglycin A |
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Description | L-Hypoglycin A 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). L-Hypoglycin A has been detected, but not quantified in, several different foods, such as european plums (Prunus domestica), opium poppies (Papaver somniferum), black crowberries (Empetrum nigrum), sorrels (Rumex acetosa), and alaska wild rhubarbs (Polygonum alpinum). This could make L-hypoglycin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on L-Hypoglycin A. |
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Structure | InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10) |
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Synonyms | Value | Source |
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2-Amino-3-(2-methylenecyclopropyl)propionic acid | ChEBI | 2-Amino-3-(2-methylenecyclopropyl)propionate | Generator | Hypoglycin | MeSH | Hypoglycin a | MeSH | Hypoglycin, (S)-isomer | MeSH | Hypoglycin, carboxy-(14)C-labeled | MeSH | 2-amino-4,5-Methylenehex-5-enoic acid | HMDB | 2-Methylenecyclopropanealanine | HMDB | 2-Methylenecyclopropanylalanine | HMDB | 2-MethyleneL-cyclopropanealanine | HMDB | alpha-amino-2-Methylenecyclopropanepropanoic acid | HMDB | alpha-amino-2-Methylenecyclopropanepropionic acid | HMDB | alpha-amino-beta-(2-Methylenecyclopropyl)propionic acid | HMDB | alpha-Aminomethylenecyclopropanepropionic acid | HMDB | beta-(Methylenecyclopropyl)alanine | HMDB | Hypoglycine a | HMDB | L-alpha-amino-beta-Methylenecyclopropanepropionic acid | HMDB | L-Hypoglycin | HMDB | 2-Amino-3-(2-methylenecyclopropyl)propanoate | Generator |
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Chemical Formula | C7H11NO2 |
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Average Molecular Weight | 141.1677 |
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Monoisotopic Molecular Weight | 141.078978601 |
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IUPAC Name | 2-amino-3-(2-methylidenecyclopropyl)propanoic acid |
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Traditional Name | hypoglycine A |
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CAS Registry Number | 156-56-9 |
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SMILES | NC(CC1CC1=C)C(O)=O |
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InChI Identifier | InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10) |
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InChI Key | OOJZCXFXPZGUBJ-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
- Carbocyclic fatty acid
- Fatty acyl
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Primary aliphatic amine
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 280 - 284 °C | 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-Hypoglycin A,1TMS,isomer #1 | C=C1CC1CC(N)C(=O)O[Si](C)(C)C | 1278.9 | Semi standard non polar | 33892256 | L-Hypoglycin A,1TMS,isomer #2 | C=C1CC1CC(N[Si](C)(C)C)C(=O)O | 1377.1 | Semi standard non polar | 33892256 | L-Hypoglycin A,2TMS,isomer #1 | C=C1CC1CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1406.9 | Semi standard non polar | 33892256 | L-Hypoglycin A,2TMS,isomer #1 | C=C1CC1CC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1458.7 | Standard non polar | 33892256 | L-Hypoglycin A,2TMS,isomer #2 | C=C1CC1CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1588.4 | Semi standard non polar | 33892256 | L-Hypoglycin A,2TMS,isomer #2 | C=C1CC1CC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1520.2 | Standard non polar | 33892256 | L-Hypoglycin A,3TMS,isomer #1 | C=C1CC1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1612.7 | Semi standard non polar | 33892256 | L-Hypoglycin A,3TMS,isomer #1 | C=C1CC1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1594.3 | Standard non polar | 33892256 | L-Hypoglycin A,1TBDMS,isomer #1 | C=C1CC1CC(N)C(=O)O[Si](C)(C)C(C)(C)C | 1505.6 | Semi standard non polar | 33892256 | L-Hypoglycin A,1TBDMS,isomer #2 | C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O | 1637.1 | Semi standard non polar | 33892256 | L-Hypoglycin A,2TBDMS,isomer #1 | C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1842.5 | Semi standard non polar | 33892256 | L-Hypoglycin A,2TBDMS,isomer #1 | C=C1CC1CC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1898.4 | Standard non polar | 33892256 | L-Hypoglycin A,2TBDMS,isomer #2 | C=C1CC1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2022.9 | Semi standard non polar | 33892256 | L-Hypoglycin A,2TBDMS,isomer #2 | C=C1CC1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1967.5 | Standard non polar | 33892256 | L-Hypoglycin A,3TBDMS,isomer #1 | C=C1CC1CC(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 | 2252.6 | Semi standard non polar | 33892256 | L-Hypoglycin A,3TBDMS,isomer #1 | C=C1CC1CC(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 | 2240.8 | 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-Hypoglycin A GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-9000000000-1860e52823f730f63355 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (1 TMS) - 70eV, Positive | splash10-0ukj-9100000000-bb541e9f44219160c2c0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - L-Hypoglycin A GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-04 | 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-Hypoglycin A 10V, Positive-QTOF | splash10-0005-9800000000-a5171a1c4df83880eaf3 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF | splash10-0002-9100000000-e69156f7fafd560dd124 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF | splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOF | splash10-0005-9800000000-a5171a1c4df83880eaf3 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF | splash10-0002-9100000000-e69156f7fafd560dd124 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF | splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOF | splash10-0005-9800000000-a5171a1c4df83880eaf3 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF | splash10-0002-9100000000-e69156f7fafd560dd124 | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF | splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c | 2015-05-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Positive-QTOF | splash10-0005-9800000000-a5171a1c4df83880eaf3 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Positive-QTOF | splash10-0002-9100000000-e69156f7fafd560dd124 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Positive-QTOF | splash10-0gb9-9000000000-d466aa46e7a29ca5ad5c | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF | splash10-0006-1900000000-d9b471c4d83e3c6242d6 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF | splash10-00dl-7900000000-ea855029d5dfccb789a2 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF | splash10-00di-9000000000-30d74facc5bc53038ca7 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF | splash10-0006-1900000000-d9b471c4d83e3c6242d6 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF | splash10-00dl-7900000000-ea855029d5dfccb789a2 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF | splash10-00di-9000000000-30d74facc5bc53038ca7 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF | splash10-0006-1900000000-d9b471c4d83e3c6242d6 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF | splash10-00dl-7900000000-ea855029d5dfccb789a2 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF | splash10-00di-9000000000-30d74facc5bc53038ca7 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF | splash10-0006-1900000000-d9b471c4d83e3c6242d6 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 20V, Negative-QTOF | splash10-00dl-7900000000-ea855029d5dfccb789a2 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 40V, Negative-QTOF | splash10-00di-9000000000-30d74facc5bc53038ca7 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - L-Hypoglycin A 10V, Negative-QTOF | splash10-0006-1900000000-23e6e4ddc37e52d21598 | 2021-09-23 | 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) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-30 | Wishart Lab | View Spectrum |
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