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Identification
YMDB IDYMDB00822
NameD-2-aminopentanoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionNorvaline, also known as (.+-.)-norvaline or D-ape, belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. Norvaline is a very strong basic compound (based on its pKa).
Structure
Thumb
Synonyms
  • (R)-norvaline
  • D-2-Aminopentanoic acid
  • D-2-Aminovaleric acid
  • D-Ape
  • D-Norvaline
  • D-Nva
  • D-2-Aminovalerate
  • D-2-Aminopentanoate
  • (.+-.)-norvaline
  • (.+/-.)-norvaline
  • 2-Amino-DL-valeric acid
  • 2-Aminopentanoic acids
  • 2-Aminovaleric acid
  • 2-Aminovaleric acids
  • alpha -DL-Aminopentanoic acid
  • alpha-Aminopentanoic acid
  • alpha-Aminovaleric acid
  • alpha-DL-Aminopentanoic acid
  • DL-2-Aminopentanoic acid
  • DL-alpha -Aminovaleric acid
  • DL-alpha-Amino-N-valenic acid
  • DL-alpha-Aminovaleric acid
  • DL-Norvaline
  • Norvaline (acd/name 4.0)
  • Norvalines
CAS number2013-12-9
WeightAverage: 117.1463
Monoisotopic: 117.078978601
InChI KeySNDPXSYFESPGGJ-SCSAIBSYSA-N
InChIInChI=1S/C5H11NO2/c1-2-3-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1
IUPAC Name(2R)-2-aminopentanoic acid
Traditional IUPAC NameD-(-)-norvaline
Chemical FormulaC5H11NO2
SMILESCCC[C@@H](N)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • 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
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility212 g/LALOGPS
logP-2ALOGPS
logP-1.9ChemAxon
logS0.26ALOGPS
pKa (Strongest Acidic)2.71ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.62 m³·mol⁻¹ChemAxon
Polarizability12.51 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, Positivesplash10-00fu-9000000000-463db7a51bc96eebb0fcJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9400000000-0b48fca984c779b8df56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9600000000-2f35fd2b5cbb04e2b774JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-37a67ae027626a67be6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b4ab8ccafd1a67b71b08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-13e844a45f41a4d61e38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9600000000-b57d7c5c40031d4c9b27JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-554519282162f7a95cd6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-92555825d99a6154218cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-5c84a32ca88953c60c8cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5a2e317c643a4b5b9221JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-9000000000-0accde1cfaabd04695a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-eceb07db0f395719c1ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9000000000-dd0b01b18824186f0dafJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00fu-9000000000-d9017cdaf64cae833eb2JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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 ID28804
HMDB IDHMDB0013716
Pubchem Compound ID439575
Kegg IDC01799
ChemSpider ID388660
FOODB IDNot Available
Wikipedia IDNorvaline
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