Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:58:23 UTC
Update Date2021-10-13 04:48:33 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 has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make L-erythrulose a potential biomarker for the consumption of these foods. L-Erythrulose is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L-Erythrulose.
Structure
Data?1582752379
Synonyms
ValueSource
L-Glycero-tetruloseChEBI
(3S)-1,3,4-Trihydroxybutan-2-oneHMDB
ErythruloseMeSH, HMDB
Erythrulose, (R)-isomerMeSH, HMDB
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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility300300 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.70331661259
DarkChem[M-H]-120.28531661259
DeepCCS[M+H]+121.05430932474
DeepCCS[M-H]-117.39730932474
DeepCCS[M-2H]-154.49930932474
DeepCCS[M+Na]+129.70430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-ErythruloseOC[C@H](O)C(=O)CO2195.6Standard polar33892256
L-ErythruloseOC[C@H](O)C(=O)CO1122.5Standard non polar33892256
L-ErythruloseOC[C@H](O)C(=O)CO1163.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Erythrulose,1TMS,isomer #1C[Si](C)(C)OC[C@H](O)C(=O)CO1272.1Semi standard non polar33892256
L-Erythrulose,1TMS,isomer #2C[Si](C)(C)O[C@@H](CO)C(=O)CO1243.4Semi standard non polar33892256
L-Erythrulose,1TMS,isomer #3C[Si](C)(C)OCC(=O)[C@@H](O)CO1290.5Semi standard non polar33892256
L-Erythrulose,1TMS,isomer #4C[Si](C)(C)OC(CO)=C(O)CO1311.7Semi standard non polar33892256
L-Erythrulose,1TMS,isomer #5C[Si](C)(C)OC(=CO)[C@@H](O)CO1318.1Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #1C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(=O)CO1361.4Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #2C[Si](C)(C)OCC(=O)[C@@H](O)CO[Si](C)(C)C1393.9Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #3C[Si](C)(C)OCC(O)=C(CO)O[Si](C)(C)C1401.1Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #4C[Si](C)(C)OC[C@H](O)C(=CO)O[Si](C)(C)C1365.3Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #5C[Si](C)(C)OCC(=O)[C@H](CO)O[Si](C)(C)C1374.2Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #6C[Si](C)(C)OC(CO)=C(CO)O[Si](C)(C)C1386.9Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #7C[Si](C)(C)OC(=CO)[C@H](CO)O[Si](C)(C)C1370.4Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #8C[Si](C)(C)OCC(O[Si](C)(C)C)=C(O)CO1430.9Semi standard non polar33892256
L-Erythrulose,2TMS,isomer #9C[Si](C)(C)OC=C(O[Si](C)(C)C)[C@@H](O)CO1405.5Semi standard non polar33892256
L-Erythrulose,3TMS,isomer #1C[Si](C)(C)OCC(=O)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C1443.1Semi standard non polar33892256
L-Erythrulose,3TMS,isomer #2C[Si](C)(C)OCC(O[Si](C)(C)C)=C(CO)O[Si](C)(C)C1503.6Semi standard non polar33892256
L-Erythrulose,3TMS,isomer #3C[Si](C)(C)OC[C@H](O[Si](C)(C)C)C(=CO)O[Si](C)(C)C1443.1Semi standard non polar33892256
L-Erythrulose,3TMS,isomer #4C[Si](C)(C)OCC(O)=C(CO[Si](C)(C)C)O[Si](C)(C)C1551.2Semi standard non polar33892256
L-Erythrulose,3TMS,isomer #5C[Si](C)(C)OC=C(O[Si](C)(C)C)[C@@H](O)CO[Si](C)(C)C1517.9Semi standard non polar33892256
L-Erythrulose,3TMS,isomer #6C[Si](C)(C)OC=C(O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C1511.0Semi standard non polar33892256
L-Erythrulose,4TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)O[Si](C)(C)C1612.4Semi standard non polar33892256
L-Erythrulose,4TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)O[Si](C)(C)C1586.7Standard non polar33892256
L-Erythrulose,4TMS,isomer #1C[Si](C)(C)OCC(O[Si](C)(C)C)=C(CO[Si](C)(C)C)O[Si](C)(C)C1417.0Standard polar33892256
L-Erythrulose,4TMS,isomer #2C[Si](C)(C)OC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C1564.7Semi standard non polar33892256
L-Erythrulose,4TMS,isomer #2C[Si](C)(C)OC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C1491.6Standard non polar33892256
L-Erythrulose,4TMS,isomer #2C[Si](C)(C)OC=C(O[Si](C)(C)C)[C@H](CO[Si](C)(C)C)O[Si](C)(C)C1478.3Standard polar33892256
L-Erythrulose,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](O)C(=O)CO1514.1Semi standard non polar33892256
L-Erythrulose,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H](CO)C(=O)CO1516.1Semi standard non polar33892256
L-Erythrulose,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC(=O)[C@@H](O)CO1531.6Semi standard non polar33892256
L-Erythrulose,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(CO)=C(O)CO1587.3Semi standard non polar33892256
L-Erythrulose,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CO)[C@@H](O)CO1551.1Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(=O)CO1805.0Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(=O)[C@@H](O)CO[Si](C)(C)C(C)(C)C1798.0Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC(O)=C(CO)O[Si](C)(C)C(C)(C)C1911.6Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC[C@H](O)C(=CO)O[Si](C)(C)C(C)(C)C1844.1Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OCC(=O)[C@H](CO)O[Si](C)(C)C(C)(C)C1822.0Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(CO)=C(CO)O[Si](C)(C)C(C)(C)C1906.1Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=CO)[C@H](CO)O[Si](C)(C)C(C)(C)C1858.1Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)=C(O)CO1909.8Semi standard non polar33892256
L-Erythrulose,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO1861.1Semi standard non polar33892256
L-Erythrulose,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(=O)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2097.1Semi standard non polar33892256
L-Erythrulose,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)=C(CO)O[Si](C)(C)C(C)(C)C2178.0Semi standard non polar33892256
L-Erythrulose,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)C(=CO)O[Si](C)(C)C(C)(C)C2107.7Semi standard non polar33892256
L-Erythrulose,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OCC(O)=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2197.0Semi standard non polar33892256
L-Erythrulose,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@@H](O)CO[Si](C)(C)C(C)(C)C2129.5Semi standard non polar33892256
L-Erythrulose,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C2143.8Semi standard non polar33892256
L-Erythrulose,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2403.2Semi standard non polar33892256
L-Erythrulose,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2288.5Standard non polar33892256
L-Erythrulose,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(O[Si](C)(C)C(C)(C)C)=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1985.5Standard polar33892256
L-Erythrulose,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2356.4Semi standard non polar33892256
L-Erythrulose,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2220.3Standard non polar33892256
L-Erythrulose,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=C(O[Si](C)(C)C(C)(C)C)[C@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1988.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Erythrulose GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-2cb7e66fe6145a66daf92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Erythrulose GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9262000000-6c3f26333dcbcf65e84a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Erythrulose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 10V, Negative-QTOFsplash10-066r-6900000000-a1f6a9b9c72a812741482017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 20V, Negative-QTOFsplash10-0aor-9500000000-ef69b474a20dfaca964b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 40V, Negative-QTOFsplash10-0a4i-9000000000-00aeaeeccfe34e308f162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 10V, Negative-QTOFsplash10-0ul0-9500000000-f38d81dfb9e7b278efba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 20V, Negative-QTOFsplash10-0a4i-9000000000-8110ee6cac7e5a51605d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 40V, Negative-QTOFsplash10-0a4i-9000000000-e19c5b01906b0f9f51352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 10V, Positive-QTOFsplash10-00di-1900000000-d7c8a475b881347f256f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 20V, Positive-QTOFsplash10-0r6r-9500000000-2db5fb9734add52a2c7f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 40V, Positive-QTOFsplash10-052o-9000000000-dad4040d50c9149852fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 10V, Positive-QTOFsplash10-000i-9200000000-a9a8d9113d5cf36859162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 20V, Positive-QTOFsplash10-000i-9100000000-1fce97582b1fa9206aec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Erythrulose 40V, Positive-QTOFsplash10-0006-9000000000-f65c9209ee34e46da4c72021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1595171
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 ]