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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:58:23 UTC
Update Date2020-02-26 21:26:19 UTC
HMDB IDHMDB0006293
Secondary Accession Numbers
  • HMDB06293
Metabolite Identification
Common NameL-Erythrulose
DescriptionL-Erythrulose belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. L-Erythrulose is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Erythrulose is an extremely reactive ketose, which rapidly glycates and crosslinks proteins, and therefore may mediate the(L-ascorbate) AsA-dependent modification of protein (ascorbylation) seen in vitro, and also proposed to occur in vivo in human lens during diabetic and age-onset cataract formation.
Structure
Data?1582752379
Synonyms
ValueSource
L-Glycero-tetruloseChEBI
(3S)-1,3,4-Trihydroxybutan-2-oneHMDB
ErythruloseHMDB
Erythrulose, (R)-isomerHMDB
Chemical FormulaC4H8O4
Average Molecular Weight120.1039
Monoisotopic Molecular Weight120.042258744
IUPAC Name(3S)-1,3,4-trihydroxybutan-2-one
Traditional NameL-erythrulose
CAS Registry Number533-50-6
SMILES
OC[C@H](O)C(=O)CO
InChI Identifier
InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m0/s1
InChI KeyUQPHVQVXLPRNCX-VKHMYHEASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy ketone
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility915 g/LALOGPS
logP-2ALOGPS
logP-2ChemAxon
logS0.88ALOGPS
pKa (Strongest Acidic)12.32ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity25.64 m³·mol⁻¹ChemAxon
Polarizability10.95 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, Positivesplash10-0a4i-9000000000-2cb7e66fe6145a66daf9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9262000000-6c3f26333dcbcf65e84aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-d7c8a475b881347f256fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r6r-9500000000-2db5fb9734add52a2c7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-9000000000-dad4040d50c9149852fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-6900000000-a1f6a9b9c72a81274148Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9500000000-ef69b474a20dfaca964bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-00aeaeeccfe34e308f16Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023881
KNApSAcK IDNot Available
Chemspider ID4573719
KEGG Compound IDC02045
BioCyc IDERYTHRULOSE
BiGG ID38964
Wikipedia LinkErythrulose
METLIN IDNot Available
PubChem Compound5460032
PDB IDLER
ChEBI ID27913
Food Biomarker OntologyNot Available
VMH IDERYTH
MarkerDB ID
References
Synthesis ReferenceMuller, H.; Montigel, C.; Reichstein, T. Pure l-erythrulose (1,2-ketotetrose). Helvetica Chimica Acta (1937), 20 1468-73.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Simpson GL, Ortwerth BJ: The non-oxidative degradation of ascorbic acid at physiological conditions. Biochim Biophys Acta. 2000 Apr 15;1501(1):12-24. [PubMed:10727845 ]