Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 18:41:51 UTC |
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Update Date | 2022-03-07 02:53:54 UTC |
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HMDB ID | HMDB0033923 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (±)-erythro-Isoleucine |
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Description | (±)-erythro-Isoleucine is a flavouring ingredient, dietary supplement, and a nutrient. Branched-chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAA denotes valine, isoleucine, and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats, and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg, and 16 mg/kg of valine, leucine, and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAA are decreased in patients with liver disease such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia, or portacaval shunt. Aromatic amino acids (AAA)-tyrosine, tryptophan, and phenylalanine (as well as methionine) are increased in these conditions. Valine, in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. The BCAA are not without side effects. Leucine alone, for example, exacerbates pellagra and can cause psychosis in pellagra patients by increasing excretion of niacin in the urine. Leucine may lower brain serotonin and dopamine. The ratio of leucine to other BCAA is greatest in pork, where leucine is 7 to 8 g and the other BCAA together are only 3 to 4 g (http://www.dcnutrition.com). |
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Structure | InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9) |
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Synonyms | Value | Source |
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(+/-)-erythro-form | HMDB | (+/-)-isoleucine | HMDB | FEMA 3295 | HMDB | Isoleucine | HMDB | 2-Amino-3-methylpentanoic acid | MeSH |
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Chemical Formula | C6H13NO2 |
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Average Molecular Weight | 131.1729 |
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Monoisotopic Molecular Weight | 131.094628665 |
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IUPAC Name | 2-amino-3-methylpentanoic acid |
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Traditional Name | L(+)-isoleucine |
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CAS Registry Number | 443-79-8 |
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SMILES | CCC(C)C(N)C(O)=O |
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InChI Identifier | InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9) |
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InChI Key | AGPKZVBTJJNPAG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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 | Isoleucine and derivatives |
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Alternative Parents | |
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Substituents | - Isoleucine or derivatives
- Alpha-amino acid
- Branched fatty acid
- Methyl-branched fatty acid
- Fatty acid
- Fatty acyl
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organopnictogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic oxide
- Hydrocarbon derivative
- 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 | |
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Disposition | |
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Process | Not Available |
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Role | |
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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 | 275 °C | Not Available | Boiling Point | 225.00 to 226.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 21.4 mg/mL at 25 °C | Not Available | LogP | -1.70 | 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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(??)-erythro-Isoleucine,1TMS,isomer #1 | CCC(C)C(N)C(=O)O[Si](C)(C)C | 1172.7 | Semi standard non polar | 33892256 | (??)-erythro-Isoleucine,1TMS,isomer #2 | CCC(C)C(N[Si](C)(C)C)C(=O)O | 1267.6 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,2TMS,isomer #1 | CCC(C)C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1308.0 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,2TMS,isomer #1 | CCC(C)C(N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1289.5 | Standard non polar | 33892256 | (±)-erythro-Isoleucine,2TMS,isomer #2 | CCC(C)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1475.9 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,2TMS,isomer #2 | CCC(C)C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1327.6 | Standard non polar | 33892256 | (±)-erythro-Isoleucine,3TMS,isomer #1 | CCC(C)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1515.0 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,3TMS,isomer #1 | CCC(C)C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1418.1 | Standard non polar | 33892256 | (??)-erythro-Isoleucine,1TBDMS,isomer #1 | CCC(C)C(N)C(=O)O[Si](C)(C)C(C)(C)C | 1391.1 | Semi standard non polar | 33892256 | (??)-erythro-Isoleucine,1TBDMS,isomer #2 | CCC(C)C(N[Si](C)(C)C(C)(C)C)C(=O)O | 1511.2 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,2TBDMS,isomer #1 | CCC(C)C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1739.4 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,2TBDMS,isomer #1 | CCC(C)C(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1714.2 | Standard non polar | 33892256 | (±)-erythro-Isoleucine,2TBDMS,isomer #2 | CCC(C)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1881.3 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,2TBDMS,isomer #2 | CCC(C)C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 1744.3 | Standard non polar | 33892256 | (±)-erythro-Isoleucine,3TBDMS,isomer #1 | CCC(C)C(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 | 2166.9 | Semi standard non polar | 33892256 | (±)-erythro-Isoleucine,3TBDMS,isomer #1 | CCC(C)C(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 | 2045.5 | Standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - (±)-erythro-Isoleucine GC-MS (1 TMS) | splash10-000i-9200000000-5690865bab18b5b529cd | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (±)-erythro-Isoleucine GC-MS (2 TMS) | splash10-0a4i-0910000000-5bb0521c0ebf8a910a75 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (±)-erythro-Isoleucine GC-MS (Non-derivatized) - 70eV, Positive | splash10-00b9-9000000000-0596928db2c9fa4c08c0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (±)-erythro-Isoleucine GC-MS (1 TMS) - 70eV, Positive | splash10-000i-9200000000-ae8694c0f3e4dcc608f9 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (±)-erythro-Isoleucine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (±)-erythro-Isoleucine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (±)-erythro-Isoleucine 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine , negative-QTOF | splash10-001i-0900000000-55eff9d9638f882c260f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-QTOF , positive-QTOF | splash10-001r-5900000000-e881c9d3a0915892d38b | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-QTOF , positive-QTOF | splash10-000i-9100000000-86db4653452734c7ee02 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-QTOF , positive-QTOF | splash10-00kr-9000000000-b5193c14ac1b83a826f8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-QTOF , positive-QTOF | splash10-0a4l-9000000000-fe2b891ad2e6f480f0e0 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-IT , positive-QTOF | splash10-000i-9000000000-e3563316bf8abf9b350e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-001r-5900000000-d1d68f4749ada07de247 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-001r-7900000000-dfc616c406406a090017 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-0019-9800000000-791a972f9062e1e1eecc | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-0019-9500000000-a332ad6eee44c4497d8f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-000i-9000000000-8d985ce33021a1b4c84a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-000i-9000000000-3dcd45c5f171baffc70d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-000i-9000000000-a9179cc22b0f645e95d5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-001i-1900000000-8f46b9e93a85ffd492cf | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-0019-9500000000-d4299ac653fc3b59494d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-000i-9000000000-60845ad5e14aa30302f9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-000i-9000000000-abdbfcab79f327c00e5a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine LC-ESI-ITFT , positive-QTOF | splash10-001i-1900000000-99f9d7387d2d9e3ec421 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (±)-erythro-Isoleucine , positive-QTOF | splash10-001r-9400000000-be94679417dff84dfe6b | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (±)-erythro-Isoleucine 10V, Positive-QTOF | splash10-0019-9600000000-c89a1d3a5cd18f7067c6 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (±)-erythro-Isoleucine 20V, Positive-QTOF | splash10-000i-9000000000-0ec2d659f4b36953fc35 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (±)-erythro-Isoleucine 40V, Positive-QTOF | splash10-0a4i-9000000000-a1549b562a6cbd32eff5 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (±)-erythro-Isoleucine 10V, Negative-QTOF | splash10-001i-2900000000-4adf1ee6b81d40f1574a | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (±)-erythro-Isoleucine 20V, Negative-QTOF | splash10-001i-5900000000-5b598d31f2916eb03739 | 2015-05-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (±)-erythro-Isoleucine 40V, Negative-QTOF | splash10-0ab9-9000000000-eb5a6b5a60bf1dce153d | 2015-05-27 | 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) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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