Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2018-05-28 23:01:47 UTC
Primary IDFDB000465
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Valine
DescriptionWidely 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 Number72-18-4
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-3-methylbutanoic acidChEBI
(S)-ValineChEBI
2-Amino-3-methylbutyric acidChEBI
L-(+)-alpha-Aminoisovaleric acidChEBI
L-alpha-Amino-beta-methylbutyric acidChEBI
L-ValinChEBI
VChEBI
ValChEBI
VALINEChEBI
(2S)-2-Amino-3-methylbutanoateGenerator
2-Amino-3-methylbutyrateGenerator
L-(+)-a-AminoisovalerateGenerator
L-(+)-a-Aminoisovaleric acidGenerator
L-(+)-alpha-AminoisovalerateGenerator
L-(+)-Α-aminoisovalerateGenerator
L-(+)-Α-aminoisovaleric acidGenerator
L-a-Amino-b-methylbutyrateGenerator
L-a-Amino-b-methylbutyric acidGenerator
L-alpha-Amino-beta-methylbutyrateGenerator
L-Α-amino-β-methylbutyrateGenerator
L-Α-amino-β-methylbutyric acidGenerator
(S)-2-Amino-3-methyl-butanoateHMDB
(S)-2-Amino-3-methyl-butanoic acidHMDB
(S)-2-Amino-3-methylbutanoateHMDB
(S)-2-Amino-3-methylbutanoic acidHMDB
(S)-2-Amino-3-methylbutyrateHMDB
(S)-2-Amino-3-methylbutyric acidHMDB
(S)-a-Amino-b-methylbutyrateHMDB
(S)-a-Amino-b-methylbutyric acidHMDB
(S)-alpha-Amino-beta-methylbutyrateHMDB
(S)-alpha-Amino-beta-methylbutyric acidHMDB
2-Amino-3-methylbutanoateHMDB
2-Amino-3-methylbutanoic acidHMDB
L ValineHMDB
(2S)-2-amino-3-MethylbutanoateGenerator
(2S)-2-amino-3-Methylbutanoic acidChEBI
(S)-2-amino-3-Methyl-butanoateHMDB
(S)-2-amino-3-Methyl-butanoic acidHMDB
(S)-2-amino-3-MethylbutanoateHMDB
(S)-2-amino-3-Methylbutanoic acidHMDB
(S)-2-amino-3-MethylbutyrateHMDB
(S)-2-amino-3-Methylbutyric acidHMDB
(S)-a-amino-b-MethylbutyrateHMDB
(S)-a-amino-b-Methylbutyric acidHMDB
(S)-alpha-amino-beta-MethylbutyrateHMDB
(S)-alpha-amino-beta-Methylbutyric acidHMDB
2-amino-3-MethylbutanoateHMDB
2-amino-3-Methylbutanoic acidHMDB
2-amino-3-MethylbutyrateGenerator
2-amino-3-Methylbutyric acidChEBI
L-(+)-α-aminoisovaleric acidbiospider
L-(+)-α-aminoisovalerateGenerator
L-(+)-α-aminoisovaleric acidGenerator
L-a-amino-b-MethylbutyrateGenerator
L-a-amino-b-Methylbutyric acidGenerator
L-alpha-amino-beta-MethylbutyrateGenerator
L-alpha-amino-beta-Methylbutyric acidChEBI
L-iso-C3H7CH(NH2)COOHbiospider
L-α-amino-β-methylbutyrateGenerator
L-α-amino-β-methylbutyric acidGenerator
Valine; L-formdb_source
Predicted Properties
PropertyValueSource
Water Solubility214 g/LALOGPS
logP-2.3ALOGPS
logP-2ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.49 m³·mol⁻¹ChemAxon
Polarizability12.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H11NO2
IUPAC name(2S)-2-amino-3-methylbutanoic acid
InChI IdentifierInChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)
InChI KeyKZSNJWFQEVHDMF-UHFFFAOYSA-N
Isomeric SMILESCC(C)C(N)C(O)=O
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
Classification
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentValine and derivatives
Alternative Parents
Substituents
  • Valine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 51.26%; H 9.46%; N 11.96%; O 27.31%DFC
Melting PointMp 315 dec. (sealed tube)DFC
Boiling PointNot Available
Experimental Water Solubility58.5 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-2.26HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.62 (NH2)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +27.6 (6M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9700000000-35c8f68fc18cba6ca71bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-1d38e555320c66c0bc39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-2fc024f8ab683584b0afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-4ad5443627bf82645ba0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9800000000-25bc658f0bf7a3fab578View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-fb2df4de077abdb8a31bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-5d10fb7acd70b2f43368View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID6050
ChEMBL IDCHEMBL43068
KEGG Compound IDC00183
Pubchem Compound ID6287
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00161
HMDB IDHMDB00883
CRC / DFC (Dictionary of Food Compounds) IDBCP95-Z:BCQ10-B
EAFUS ID3824
Dr. Duke IDVALINE
BIGG ID34167
KNApSAcK IDC00001398
HET IDVAL
Flavornet IDNot Available
GoodScent IDrw1055601
SuperScent IDNot Available
Wikipedia IDValine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti encephalopathic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
essentialDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
Enzymes
NameGene NameUniProt ID
Propionyl-CoA carboxylase beta chain, mitochondrialPCCBP05166
Branched-chain-amino-acid aminotransferase, cytosolicBCAT1P54687
Branched-chain-amino-acid aminotransferase, mitochondrialBCAT2O15382
Valine--tRNA ligaseVARSP26640
Valine--tRNA ligase, mitochondrialVARS2Q5ST30
Pathways
NameSMPDB LinkKEGG Link
Propanoate MetabolismSMP00016 map00640
Transcription/TranslationSMP00019 Not Available
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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).