FComEx: L-Isoleucine (PC000129)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:42 UTC

Update date

2017-01-19 02:36:13 UTC

FoodComEx ID

PC000129

FoodDB Record

FDB012397

Chemical Information

Name

L-Isoleucine

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.

CAS Number

73-32-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(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

Chemical Formula

C6H13NO2

IUPAC name

2-amino-3-methylpentanoic acid

InChI Identifier

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)

InChI Key

AGPKZVBTJJNPAG-UHFFFAOYSA-N

Isomeric SMILES

CCC(C)C(N)C(O)=O

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Isoleucine and derivatives

Alternative Parents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha-amino acid (CHEBI:38264 )
branched-chain amino acid (CHEBI:38264 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-1.70	HANSCH,C ET AL. (1995)
Experimental Water Solubility	34.4 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 285-286° dec.	DFC

Foods of Origin