Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:09 UTC |
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Update date | 2019-11-26 03:06:42 UTC |
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Primary ID | FDB012397 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Isoleucine |
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Description | Dietary supplement, 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; They provide ingredients for the manufacturing of other essential biochemical components in the body, some of which are utilized for the production of energy, stimulants to the upper brain and helping you to be more alert.; 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. A dose of 3 g of isoleucine added to the niacin regime has cleared leucine-aggravated psychosis in schizophrenic patients. Isoleucine may have potential as an antipsychotic treatment. Leucine is more highly concentrated in foods than other amino acids. A cup of milk contains 800 mg of leucine and only 500 mg of isoleucine and valine. A cup of wheat germ has about 1.6 g of leucine and 1 g of isoleucine and valine. The ratio evens out in eggs and cheese. One egg and an ounce of most cheeses each contain about 400 mg of leucine and 400 mg of valine and isoleucine. 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). L-Isoleucine is found in many foods, some of which are atlantic salmon, quince, baked potato, and pistachio. |
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CAS Number | 73-32-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(+/-)-erythro-form | HMDB | (+/-)-isoleucine | HMDB | FEMA 3295 | HMDB | Isoleucine | HMDB | 2-Amino-3-methylpentanoic acid | MeSH | (2S,3S)-2-amino-3-Methyl-pentanoate | HMDB | (2S,3S)-2-amino-3-Methyl-pentanoic acid | HMDB | (2S,3S)-2-amino-3-Methylpentanoate | Generator | (2S,3S)-2-amino-3-Methylpentanoic acid | ChEBI | (2S,3S)-a-amino-b-Methyl-N-valerate | HMDB | (2S,3S)-a-amino-b-Methyl-N-valeric acid | HMDB | (2S,3S)-a-amino-b-Methylvalerate | HMDB | (2S,3S)-a-amino-b-Methylvaleric acid | HMDB | (2S,3S)-Alph-amino-beta-methylvalerate | HMDB | (2S,3S)-Alph-amino-beta-methylvaleric acid | HMDB | (2S,3S)-alpha-amino-beta-Merthyl-N-valerate | HMDB | (2S,3S)-alpha-amino-beta-Merthyl-N-valeric acid | HMDB | (2S,3S)-alpha-amino-beta-Merthylvalerate | HMDB | (2S,3S)-alpha-amino-beta-Merthylvaleric acid | HMDB | (2S,3S)-alpha-amino-beta-Methyl-N-valerate | HMDB | (2S,3S)-alpha-amino-beta-Methyl-N-valeric acid | HMDB | (2S,3S)-alpha-amino-beta-Methylvalerate | HMDB | (2S,3S)-alpha-amino-beta-Methylvaleric acid | HMDB | (S,S)-Isoleucine | HMDB | (S)-Isoleucine | HMDB | [S-(R*,r*)]-2-amino-3-methylpentanoate | HMDB | [S-(R*,r*)]-2-amino-3-methylpentanoic acid | HMDB | α-amino-β-methylvaleric acid | biospider | 2-amino-3-Methylpentanoate | HMDB | 2-amino-3-Methylpentanoic acid | HMDB | 2-amino-3-Methylvalerate | Generator | 2-amino-3-Methylvaleric acid | ChEBI | 2S,3S-Isoleucine | HMDB | a-amino-b-Methylvalerate | Generator | a-amino-b-Methylvaleric acid | Generator | alpha-amino-beta-Methylvalerate | Generator | alpha-amino-beta-Methylvaleric acid | ChEBI | erythro-L-Isoleucine | HMDB | Ile | ChEBI | Iso-leucine | HMDB | Isoleucine (van) | biospider | Isoleucine; L-erythro-form | db_source | L-(+)-Isoleucine | HMDB | L-Ile | HMDB | L-Isoleucine | db_source | sec-C4H9CH(NH2)COOH | biospider | α-amino-β-methylvalerate | Generator | α-amino-β-methylvaleric acid | Generator |
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Predicted Properties | |
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Chemical Formula | C6H13NO2 |
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IUPAC name | 2-amino-3-methylpentanoic acid |
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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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Isomeric SMILES | CCC(C)C(N)C(O)=O |
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Average Molecular Weight | 131.1729 |
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Monoisotopic Molecular Weight | 131.094628665 |
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Classification |
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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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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 54.94%; H 9.99%; N 10.68%; O 24.39% | DFC |
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Melting Point | Mp 285-286° dec. | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | 34.4 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | -1.70 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa2 9.68 (NH2) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]D +51.8 (5M HCl) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | (±)-erythro-Isoleucine, 1 TMS, GC-MS Spectrum | splash10-000i-9200000000-5690865bab18b5b529cd | Spectrum | GC-MS | (±)-erythro-Isoleucine, 2 TMS, GC-MS Spectrum | splash10-0a4i-0910000000-5bb0521c0ebf8a910a75 | Spectrum | Predicted GC-MS | (±)-erythro-Isoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00b9-9000000000-0596928db2c9fa4c08c0 | Spectrum | Predicted GC-MS | (±)-erythro-Isoleucine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-9200000000-ae8694c0f3e4dcc608f9 | Spectrum | Predicted GC-MS | (±)-erythro-Isoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (±)-erythro-Isoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (±)-erythro-Isoleucine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - , negative | splash10-001i-0900000000-55eff9d9638f882c260f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001r-5900000000-e881c9d3a0915892d38b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-9100000000-86db4653452734c7ee02 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00kr-9000000000-b5193c14ac1b83a826f8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0a4l-9000000000-fe2b891ad2e6f480f0e0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-000i-9000000000-e3563316bf8abf9b350e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001r-5900000000-d1d68f4749ada07de247 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001r-7900000000-dfc616c406406a090017 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0019-9800000000-791a972f9062e1e1eecc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0019-9500000000-a332ad6eee44c4497d8f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-9000000000-8d985ce33021a1b4c84a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-9000000000-3dcd45c5f171baffc70d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-9000000000-a9179cc22b0f645e95d5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001i-1900000000-8f46b9e93a85ffd492cf | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0019-9500000000-d4299ac653fc3b59494d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-9000000000-60845ad5e14aa30302f9 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-9000000000-abdbfcab79f327c00e5a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-001i-1900000000-99f9d7387d2d9e3ec421 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-001r-9400000000-be94679417dff84dfe6b | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0019-9600000000-c89a1d3a5cd18f7067c6 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-9000000000-0ec2d659f4b36953fc35 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-a1549b562a6cbd32eff5 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-2900000000-4adf1ee6b81d40f1574a | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-5900000000-5b598d31f2916eb03739 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ab9-9000000000-eb5a6b5a60bf1dce153d | 2015-05-27 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 6067 |
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ChEMBL ID | CHEMBL1233584 |
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KEGG Compound ID | C00407 |
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Pubchem Compound ID | 6306 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00167 |
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HMDB ID | HMDB00172 |
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CRC / DFC (Dictionary of Food Compounds) ID | GXX01-C:HGS59-W |
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EAFUS ID | 1894 |
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Dr. Duke ID | L-(+)-ISOLEUCINE|ISOLEUCINE |
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BIGG ID | 34887 |
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KNApSAcK ID | C00001374 |
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HET ID | ILE |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1253751 |
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SuperScent ID | Not Available |
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Wikipedia ID | Isoleucine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Branched-chain-amino-acid aminotransferase, cytosolic | BCAT1 | P54687 | Branched-chain-amino-acid aminotransferase, mitochondrial | BCAT2 | O15382 | Isoleucine--tRNA ligase, cytoplasmic | IARS | P41252 | Isoleucine--tRNA ligase, mitochondrial | IARS2 | Q9NSE4 |
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Pathways | Name | SMPDB Link | KEGG Link |
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Transcription/Translation | SMP00019 | Not Available | Valine, Leucine and Isoleucine Degradation | SMP00032 | map00280 |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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odorless |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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