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(±)-Valine (FDB012740)

Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2019-11-26 03:07:30 UTC
Primary IDFDB012740
Secondary Accession Numbers
  • FDB000465
Chemical Information
FooDB Name(±)-Valine
DescriptionFlavouring ingredient 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; 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). (±)-Valine is found in many foods, some of which are green bell pepper, green zucchini, italian sweet red pepper, and red bell pepper.
CAS Number516-06-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
Polarizability12.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H11NO2
IUPAC name2-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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 51.26%; H 9.46%; N 11.96%; O 27.31%DFC
Melting PointMp 298 dec. (sealed tube)DFC
Boiling PointNot Available
Experimental Water Solubility74.4 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-2.26HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.62 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-5d10fb7acd70b2f433682014-09-20View Spectrum
Predicted GC-MSL-Valine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9000000000-b385a34b355e27f372f2Spectrum
Predicted GC-MSL-Valine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Valine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4i-9000000000-12c0c153853040e5f2402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4i-9000000000-4bcd1882caae0637c2192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9500000000-afc0dce1f70c0dda87ad2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00xr-9500000000-caf607c62eb6d53c869d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-00di-9000000000-93d5343b3c2a960bcc522021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00xr-9400000000-798c3e9aabf77defea1e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-9010000000-3fcf5945d13cf669aab92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-00xs-9660000000-f656a2da18f3c179f0662021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 85V, Positivesplash10-00xr-9700000000-3f03a996f8ff55877d272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 65V, Positivesplash10-00xr-9700000000-dc0111101c029fe7adfb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00xr-9630000000-b24c03a401b4fc9099b82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 70V, Positivesplash10-00xr-9700000000-d40488c0a479b9fa7cee2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-5c937e87602950557d6b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-00xr-9730000000-031952152065adfa03582021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00xr-9500000000-8f08e0ea98fccf412a7d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4i-9000000000-ef8c1d90edfa1bdafc1d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 25V, Positivesplash10-05fr-9000000000-05b391e6cf755709eb5e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01b9-5900000000-cb4e7bfd595dddb153812021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-9627600a36c89ee0f9592021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9700000000-35c8f68fc18cba6ca71b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-1d38e555320c66c0bc392015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-2fc024f8ab683584b0af2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-4ad5443627bf82645ba02015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9800000000-25bc658f0bf7a3fab5782015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-fb2df4de077abdb8a31b2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 22.5 MHz, D2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBCP95-Z:HKL28-F
EAFUS ID1070
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1036191
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).