Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2018-01-23 19:25:02 UTC
Primary IDFDB012740
Secondary Accession NumbersNot Available
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
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
DL-α-aminoisovaleric acidbiospider
FEMA 3444db_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 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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0006-0910000000-23bfcf2795f71f458bdaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0006-0920000000-7892bb9d4d9afcc23410View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0006-0910000000-f2491152816b9c5dc7edView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0znj-1900000000-7c976d7c11a402db399fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dl-8910000000-78e8ee971ad7298c23cdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-9200000000-805e6724e5181af78c81View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0006-0910000000-a212771a5ea868139d5aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-059t-0900000000-7b8e4e98ac9158bf26d9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0910000000-9079324093be9a14d47aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0910000000-23bfcf2795f71f458bdaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0920000000-7892bb9d4d9afcc23410View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0910000000-f2491152816b9c5dc7edView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0znj-1900000000-7c976d7c11a402db399fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-000i-2920000000-1628d46d5520c5f20de8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dl-8910000000-78e8ee971ad7298c23cdView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-9200000000-805e6724e5181af78c81View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-0910000000-a212771a5ea868139d5aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9000000000-602d1e01bc7567493e4cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9500000000-a758682a7aafbd0d553eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-67498a3295a1fe788c4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-fb359f44fcf1b83ee14dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-8e5f620c04615765a062View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014r-0900000000-619d80cc41221405e0bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-17ab53cec2e6b727c3e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-0dfbcc85d6423af91edaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014l-4900000000-c50d79ba3a5013bcf29fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0900000000-67a7784963ec75cecaa0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-9000000000-4569516f23d8a712b434View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-d928cac1226f19b8edc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-34059351f2cbd94a8accView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-a36d8d68a6705027415fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-1a5d8f4c1b293de18fedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-0900000000-b410df2c18dfc8ab7165View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0gi0-6900000000-c87ff036e3a5d15b7670View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9000000000-561b3b28fa82e0b10658View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-05fr-9000000000-11e7c0a3d5cf8e4dedfeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-6a6f8cd9629b0f09469cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-4518f691bbda5739c0f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-014i-0900000000-a931cfc8207edac33775View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-9000000000-430332b13b8c6368136bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-ffb286a8ae38a0a3e6d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9500000000-bb54662a5fd1dd142d90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-1f7d9c10db4226a383c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-f6d7e45bb3f3436e5eb7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-05fr-9000000000-5d10fb7acd70b2f43368View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).