FComEx: L-Valine (PC000024)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:27 UTC

Update date

2017-01-19 02:36:10 UTC

FoodComEx ID

PC000024

FoodDB Record

Not Available

Chemical Information

Name

L-Valine

Description

Widely distributed in nature as one of the principal protein amino acids. Dietary supplement 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.; Many types of inborn errors of BCAA metabolism exist, and are marked by various abnormalities. The most common form is the maple syrup urine disease, marked by a characteristic urinary odor. Other abnormalities are associated with a wide range of symptoms, such as mental retardation, ataxia, hypoglycemia, spinal muscle atrophy, rash, vomiting and excessive muscle movement. Most forms of BCAA metabolism errors are corrected by dietary restriction of BCAA and at least one form is correctable by supplementation with 10 mg of biotin daily. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; L-valine is a branched-chain essential amino acid (BCAA) that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. Valine is one of three branched-chain amino acids (the others are leucine and isoleucine) that enhance energy, increase endurance, and aid in muscle tissue recovery and repair. This group also lowers elevated blood sugar levels and increases growth hormone production. Supplemental valine should always be combined with isoleucine and leucine at a respective milligram ratio of 2:1:2. It is an essential amino acid found in proteins; Valine (abbreviated as Val or V) is an ?-amino acid with the chemical formula HO2CCH(NH2)CH(CH3)2. L-Valine is one of 20 proteinogenic amino acids. Its codons are GUU, GUC, GUA, and GUG. This essential amino acid is classified as nonpolar. Along with leucine and isoleucine, valine is a branched-chain amino acid. It is named after the plant valerian. In sickle-cell disease, valine substitutes for the hydrophilic amino acid glutamic acid in hemoglobin. Because valine is hydrophobic, the hemoglobin does not fold correctly.; Valine is an essential amino acid, hence it must be ingested, usually as a component of proteins. And will flow bood engorged pumps to the penile region. It is synthesized in plants via several steps starting from pyruvic acid. The initial part of the pathway also leads to leucine. The intermediate ?-ketovalerate undergoes reductive amination with glutamate. Enzymes involved in this biosynthesis include:; 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. (http://www.dcnutrition.com).

CAS Number

72-18-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S)-2-amino-3-Methylbutanoate	Generator
(2S)-2-amino-3-Methylbutanoic acid	ChEBI
(S)-2-amino-3-Methyl-butanoate	HMDB
(S)-2-amino-3-Methyl-butanoic acid	HMDB
(S)-2-amino-3-Methylbutanoate	HMDB
(S)-2-amino-3-Methylbutanoic acid	HMDB
(S)-2-amino-3-Methylbutyrate	HMDB
(S)-2-amino-3-Methylbutyric acid	HMDB
(S)-a-amino-b-Methylbutyrate	HMDB
(S)-a-amino-b-Methylbutyric acid	HMDB
(S)-alpha-amino-beta-Methylbutyrate	HMDB
(S)-alpha-amino-beta-Methylbutyric acid	HMDB
(S)-Valine	ChEBI
2-amino-3-Methylbutanoate	HMDB
2-amino-3-Methylbutanoic acid	HMDB
2-amino-3-Methylbutyrate	Generator
2-amino-3-Methylbutyric acid	ChEBI
L-(+)-α-aminoisovaleric acid	biospider
L-(+)-a-Aminoisovalerate	Generator
L-(+)-a-Aminoisovaleric acid	Generator
L-(+)-alpha-Aminoisovalerate	Generator
L-(+)-alpha-Aminoisovaleric acid	ChEBI
L-(+)-α-aminoisovalerate	Generator
L-(+)-α-aminoisovaleric acid	Generator
L-a-amino-b-Methylbutyrate	Generator
L-a-amino-b-Methylbutyric acid	Generator
L-alpha-amino-beta-Methylbutyrate	Generator
L-alpha-amino-beta-Methylbutyric acid	ChEBI
L-iso-C3H7CH(NH2)COOH	biospider
L-Valin	ChEBI
L-α-amino-β-methylbutyrate	Generator
L-α-amino-β-methylbutyric acid	Generator
V	ChEBI
Val	ChEBI
VALINE	ChEBI
Valine; L-form	db_source

Chemical Formula

Not Available

IUPAC name

Not Available

InChI Identifier

InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)

InChI Key

KZSNJWFQEVHDMF-UHFFFAOYSA-N

Isomeric SMILES

CC(C)C(N)C(O)=O

Average Molecular Weight

117.1463

Monoisotopic Molecular Weight

117.078978601

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as valine and derivatives. Valine and derivatives are compounds containing valine or a derivative thereof resulting from reaction of valine 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

Valine and derivatives

Alternative Parents

Substituents

Valine 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:27266 )
branched-chain amino acid (CHEBI:27266 )
Amino fatty acids (LMFA01100046 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-2.26	HANSCH,C ET AL. (1995)
Experimental Water Solubility	58.5 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 315 dec. (sealed tube)	DFC

Foods of Origin