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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:32:31 UTC
Update Date2019-07-23 06:14:19 UTC
HMDB IDHMDB0033780
Secondary Accession Numbers
  • HMDB33780
Metabolite Identification
Common NameD-Asparagine
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. D-Asparagine is a very strong basic compound (based on its pKa). Its codons are AAU and AAC (Wikipedia ). It is biosynthesized from ASPARTIC ACID and AMMONIA by asparagine synthetase. It is not an essential amino acid. A non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue.
Structure
Data?1563862459
Synonyms
ValueSource
(2R)-2,4-Diamino-4-oxobutanoic acidChEBI
(2R)-2-Amino-3-carbamoylpropanoic acidChEBI
(R)-2-Amino-3-carbamoylpropanoic acidChEBI
D-2-Aminosuccinamic acidChEBI
D-AsparaginChEBI
D-Aspartic acid beta-amideChEBI
DSGChEBI
(2R)-2,4-Diamino-4-oxobutanoateGenerator
(2R)-2-Amino-3-carbamoylpropanoateGenerator
(R)-2-Amino-3-carbamoylpropanoateGenerator
D-2-AminosuccinamateGenerator
D-Aspartate b-amideGenerator
D-Aspartate beta-amideGenerator
D-Aspartate β-amideGenerator
D-Aspartic acid b-amideGenerator
D-Aspartic acid β-amideGenerator
(R)-2-Aminosuccinamic acidHMDB
(R)-2-Aminosuccinic acid 4-amideHMDB
D-Aspartic acid 4-amideHMDB
Chemical FormulaC4H8N2O3
Average Molecular Weight132.1179
Monoisotopic Molecular Weight132.053492132
IUPAC Name(2R)-2-amino-3-carbamoylpropanoic acid
Traditional NameD-asparagine
CAS Registry Number2058-58-4
SMILES
N[C@H](CC(N)=O)C(O)=O
InChI Identifier
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1
InChI KeyDCXYFEDJOCDNAF-UWTATZPHSA-N
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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9100000000-5881591331bd059b7e7dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-9200000000-486021baa3768a16df83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-015i-9700000000-74565d33539905a7f4e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9100000000-439d8b494bcc2c657584Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-3d057971482c08a22ae1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-4900000000-44107cc9e625603aa1d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0016-9300000000-887eb70e6788b4b7c513Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d76a7af45b6c73471794Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03943
Phenol Explorer Compound IDNot Available
FooDB IDFDB011935
KNApSAcK IDNot Available
Chemspider ID388679
KEGG Compound IDC01905
BioCyc IDCPD-3633
BiGG IDNot Available
Wikipedia LinkAsparagine
METLIN IDNot Available
PubChem Compound439600
PDB IDDSG
ChEBI ID28159
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .