2-Amino-3-methylpentanoic acid
PubChem CID: 791
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| Compound Synonyms | DL-ISOLEUCINE, 443-79-8, 2-Amino-3-methylpentanoic acid, DL-Allo-isoleucine, 2095501-92-9, L(+)-Isoleucine, 2-amino-3-methyl-pentanoic acid, Isoleucine, DL-, 3107-04-8, DL-2-Amino-3-methylpentanoic acid, H-DL-allo-Ile-OH, CHEBI:38264, DL-Alloisoleucine, Isoleucine, allo-, Isoleucine, threo-, L-Isoleucine, allo-, L-Isoleucine, threo-, NSC-9958, NSC46708, MFCD00065934, (dl)-isoleucine, Isoleucine #, NSC-206282, Norvaline, threo-, NCGC00181164-01, Norvaline, erythro-, (+/-)-Isoleucine, L-Norvaline, threo-, (+/-)-erythro-form, ISOLEUCINE,(L), (+/-)-erythro-Isoleucine, SCHEMBL8868, Acetic acid, (R*,R*)-, WLN: QVYZY2&1 -L, L-Isoleucine, non animal origin, 2-amino-3-methyl pentanoic acid, FEMA 3295, DTXSID80901480, NSC9958, WLN: QVYZY2&1 -L,ALLO, Pentanoic acid, [S-(R*,R*)]-, Pentanoic acid, [S-(R*,S*)]-, BBL100034, FD3037, NSC206282, STL185601, AKOS000120120, AKOS016051419, DL-Allo-isoleucine (H-DL-xiIle-OH), CS-W013422, HY-W012706, PB48180, SB75593, .alpha.-Amino-.beta.-methylvaleric acid, AC-24098, AS-49219, DA-62942, SY017751, SY022275, SY022276, SY022277, SY022340, (2r,3r)-2-amino-3-methyl-pentanoic acid, DB-017950, DB-043068, DB-043069, [(2R,3R)-2-amino-3-methylpentanoic acid], A0212, NS00080659, EN300-19355, SR-01000944853, SR-01000944853-1, BRD-A02232681-001-01-8, Q27117434, Q60662693, Z104473608, B821F6FC-012D-4267-ABE2-AA1F36808C01 |
|---|---|
| Topological Polar Surface Area | 63.3 |
| Hydrogen Bond Donor Count | 2.0 |
| Inchi Key | AGPKZVBTJJNPAG-UHFFFAOYSA-N |
| Rotatable Bond Count | 3.0 |
| State | Solid |
| Substituent Name | Alpha-amino acid, Methyl-branched fatty acid, Branched fatty acid, Amino fatty acid, Fatty acyl, Fatty acid, Monocarboxylic acid or derivatives, Carboxylic acid, Hydrocarbon derivative, Primary amine, Organooxygen compound, Organonitrogen compound, Primary aliphatic amine, Carbonyl group, Amine, Aliphatic acyclic compound, L-alpha-amino acid |
| Synonyms | (+/-)-erythro-form, (+/-)-isoleucine, (±)-Isoleucine, FEMA 3295, Isoleucine, Isoleucine, (±)-erythro-form, (2S,3S)-2-amino-3-Methyl-pentanoate, (2S,3S)-2-amino-3-Methyl-pentanoic acid, (2S,3S)-2-amino-3-Methylpentanoate, (2S,3S)-2-amino-3-Methylpentanoic acid, (2S,3S)-a-amino-b-Methyl-N-valerate, (2S,3S)-a-amino-b-Methyl-N-valeric acid, (2S,3S)-a-amino-b-Methylvalerate, (2S,3S)-a-amino-b-Methylvaleric acid, (2S,3S)-Alph-amino-beta-methylvalerate, (2S,3S)-Alph-amino-beta-methylvaleric acid, (2S,3S)-alpha-amino-beta-Merthyl-N-valerate, (2S,3S)-alpha-amino-beta-Merthyl-N-valeric acid, (2S,3S)-alpha-amino-beta-Merthylvalerate, (2S,3S)-alpha-amino-beta-Merthylvaleric acid, (2S,3S)-alpha-amino-beta-Methyl-N-valerate, (2S,3S)-alpha-amino-beta-Methyl-N-valeric acid, (2S,3S)-alpha-amino-beta-Methylvalerate, (2S,3S)-alpha-amino-beta-Methylvaleric acid, (S,S)-Isoleucine, (S)-Isoleucine, [S-(R*,r*)]-2-amino-3-methylpentanoate, [S-(R*,r*)]-2-amino-3-methylpentanoic acid, &alpha, -amino-&beta, -methylvaleric acid, 2-amino-3-Methylpentanoate, 2-amino-3-Methylpentanoic acid, 2-amino-3-Methylvalerate, 2-amino-3-Methylvaleric acid, 2S,3S-Isoleucine, a-amino-b-Methylvalerate, a-amino-b-Methylvaleric acid, alpha-amino-beta-Methylvalerate, alpha-amino-beta-Methylvaleric acid, erythro-L-Isoleucine, Ile, Iso-leucine, Isoleucine (van), Isoleucine, L-erythro-form, L-(+)-Isoleucine, L-Ile, L-Isoleucine, sec-C4H9CH(NH2)COOH, α-amino-β-methylvalerate, α-amino-β-methylvaleric acid |
| Heavy Atom Count | 9.0 |
| Pathway Kegg Map Id | map00280 |
| Compound Name | 2-Amino-3-methylpentanoic acid |
| Kingdom | Organic compounds |
| Description | Flavouring ingredient, 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, 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) |
| Exact Mass | 131.095 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 131.095 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 103.0 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 131.17 |
| Database Name | fooddb_chem_all;pubchem |
| Covalent Unit Count | 1.0 |
| Enzyme Uniprot Id | P54687, O15382, P41252, Q9NSE4 |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 2-amino-3-methylpentanoic acid |
| Total Atom Stereocenter Count | 2.0 |
| Total Bond Stereocenter Count | 0.0 |
| Class | Carboxylic acids and derivatives |
| Inchi | InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9) |
| Smiles | CCC(C)C(C(=O)O)N |
| Xlogp | -1.7 |
| Superclass | Organic acids and derivatives |
| Defined Bond Stereocenter Count | 0.0 |
| Subclass | Amino acids, peptides, and analogues |
| Molecular Formula | C6H13NO2 |
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