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Identification
YMDB IDYMDB01000
NameD-Valine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Valine, also known as (R)-valine or D-valin, 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. D-Valine is a very strong basic compound (based on its pKa). D-Valine may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (2R)-2-amino-3-methylbutanoic acid
  • (R)-2-Amino-3-methylbutyric acid
  • (R)-Valine
  • ACV
  • D-Valin
  • D-Valine
  • delta-(L-2-Aminoadipyl)-L-cysteinyl-D-valine
  • L-delta-(alpha-Aminoadipoyl)-L-cysteinyl-D-valine
  • N-[L-5-Amino-5-carboxypentanoyl]-L-cysteinyl-D-valine
  • Valine
  • Valine, D-
  • DVA
  • (2R)-2-Amino-3-methylbutanoate
  • (R)-2-Amino-3-methylbutyrate
CAS number640-68-6
WeightAverage: 117.1463
Monoisotopic: 117.078978601
InChI KeyKZSNJWFQEVHDMF-SCSAIBSYSA-N
InChIInChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m1/s1
IUPAC Name(2R)-2-amino-3-methylbutanoic acid
Traditional IUPAC NameD-valine
Chemical FormulaC5H11NO2
SMILESCC(C)[C@@H](N)C(O)=O
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.
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
  • D-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
Physical Properties
StateSolid
Charge0
Melting point295-300 °C
Experimental Properties
PropertyValueReference
Water Solubility58.5 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-2.26 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9000000000-602d1e01bc7567493e4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9500000000-bb54662a5fd1dd142d90JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-1f7d9c10db4226a383c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9000000000-f6d7e45bb3f3436e5eb7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-f5c404ed60b91c5f9cb9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-5900000000-b6ba2bbf6fc32d3451e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-0374f01d56dca105471aJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Yow, G. Y., Uo, T., Yoshimura, T., Esaki, N. (2004). "D-amino acid N-acetyltransferase of Saccharomyces cerevisiae: a close homologue of histone acetyltransferase Hpa2p acting exclusively on free D-amino acids." Arch Microbiol 182:396-403.15375647
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID27477
HMDB IDNot Available
Pubchem Compound ID71563
Kegg IDC05556
ChemSpider ID64635
FOODB IDNot Available
WikipediaValine
BioCyc IDNot Available

Enzymes

General function:
Involved in N-acetyltransferase activity
Specific function:
N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:
HPA3
Uniprot ID:
P39979
Molecular weight:
20698.5
Reactions
acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid