Identification
YMDB IDYMDB00849
NameD-Asparagine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionD-Asparagine, also known as DSG, belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review a significant number of articles have been published on D-Asparagine.
Structure
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Synonyms
  • (-)-Asparagine
  • (2R)-2-amino-3-carbamoylpropanoic acid
  • (2R)-2,4-diamino-4-oxobutanoic acid
  • (R)-2-amino-3-carbamoylpropanoic acid
  • (S)-2,4-Diamino-4-oxobutanoate
  • (S)-2,4-Diamino-4-oxobutanoic acid
  • (S)-Asparagine
  • 2-Aminosuccinamate
  • 2-Aminosuccinamic acid
  • a-Aminosuccinamate
  • a-Aminosuccinamic acid
  • Agedoite
  • alpha Amminosuccinamate
  • alpha Amminosuccinamic acid
  • alpha-Aminosuccinamate
  • alpha-Aminosuccinamic acid
  • Altheine
  • Asn
  • Asparagine
  • Asparagine acid
  • Asparagine, L-
  • Asparamide
  • Aspartamate
  • Aspartamic acid
  • Aspartic acid amide
  • Aspartic acid b-amide
  • Aspartic acid beta amide
  • B2,4-(S)-diamino-4-oxo-utanoate
  • B2,4-(S)-diamino-4-oxo-utanoic acid
  • D-2-aminosuccinamic acid
  • D-Asparagin
  • D-Asparagine
  • D-aspartic acid beta-amide
  • L-2,4-Diamino-4-oxobutanoate
  • L-2,4-Diamino-4-oxobutanoic acid
  • l-Asparagine
  • L-Aspartamine
  • L-b-Asparagine
  • L-beta-Asparagine
  • DSG
  • (2R)-2,4-Diamino-4-oxobutanoate
  • (2R)-2-Amino-3-carbamoylpropanoate
  • (R)-2-Amino-3-carbamoylpropanoate
  • D-2-Aminosuccinamate
  • D-Aspartate b-amide
  • D-Aspartate beta-amide
  • D-Aspartate β-amide
  • D-Aspartic acid b-amide
  • D-Aspartic acid β-amide
  • (R)-2-Aminosuccinamic acid
  • (R)-2-Aminosuccinic acid 4-amide
  • D-Aspartic acid 4-amide
CAS number2058-58-4
WeightAverage: 132.1179
Monoisotopic: 132.053492132
InChI KeyDCXYFEDJOCDNAF-UWTATZPHSA-N
InChIInChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1
IUPAC Name(2R)-2-amino-3-carbamoylpropanoic acid
Traditional IUPAC NameD-asparagine
Chemical FormulaC4H8N2O3
SMILESN[C@H](CC(N)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine 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 ParentAsparagine and derivatives
Alternative Parents
Substituents
  • Asparagine or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Fatty amide
  • Fatty acyl
  • Fatty acid
  • Carboxamide group
  • Amino acid
  • Primary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point234-235 °C
Experimental Properties
PropertyValueReference
Water Solubility29.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.82 [CHMELIK,J ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility168 g/LALOGPS
logP-3.4ALOGPS
logP-4.3ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.35 m³·mol⁻¹ChemAxon
Polarizability11.77 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 Pathways
Asparagine metabolismPW002274 ThumbThumb?image type=greyscaleThumb?image type=simple
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, Positivesplash10-000f-9100000000-5881591331bd059b7e7dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9200000000-486021baa3768a16df83JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-9700000000-74565d33539905a7f4e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9100000000-439d8b494bcc2c657584JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3d057971482c08a22ae1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4900000000-44107cc9e625603aa1d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0016-9300000000-887eb70e6788b4b7c513JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d76a7af45b6c73471794JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-831feb8b7ce011d73c8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0076-9200000000-1bed3281e3ab973b1841JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b990d7063181be79cb69JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-9300000000-e07b80cc3c9fd3b9281dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-5c032b7eeb69c0213827JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a7471da8aeb0443ffb99JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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 ID28159
HMDB IDHMDB00168
Pubchem Compound ID6267
Kegg IDC01905
ChemSpider ID388679
FOODB IDFDB011935
WikipediaAsparagine
BioCyc IDASN

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