Record Information
Version1.0
Creation date2011-09-21 00:18:08 UTC
Update date2019-11-26 03:21:05 UTC
Primary IDFDB022698
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Xylulose
DescriptionD-xylulose is a monosaccharide containing five carbon atoms. D-xylulose is converted from xylitol by the enzyme NAD+-linked xylitol dehydrogenase (EC 1.1.1.9) in the glucuronate pathway, the most important xylitol-handling metabolic pathway in mammals. This activity has been described in human erythrocytes. Most likely, D-xylulose (as well as D-arabinose or D-ribulose) is a precursor of the pentiol D-arabitol, since pentitols are derived from their corresponding pentose phosphate precursors via pentoses. This pathway can play a role in inherited metabolic disorders underlying the accumulation of pentitols e.g., ribose 5-phosphate isomerase deficiency and transaldolase deficiency. Although pentitols are present in all living organisms, knowledge concerning their metabolism is limited. (PMID: 15234337, Mol Genet Metabolite 2004 Jul;82(3):231-7.) [HMDB]. D-Xylulose is found in many foods, some of which are garden onion, american cranberry, cucumber, and radish.
CAS Number551-84-8
Structure
Thumb
Synonyms
SynonymSource
D-LyxuloseChEBI
D-Threo-pentuloseChEBI
D-XulChEBI
LyxuloseMeSH
Xylulose, (D-threo)-isomerMeSH
XyluloseMeSH
Xylulose, (L-threo)-isomerMeSH
D-threo-Pentulosehmdb
D-Xylulosehmdb
Predicted Properties
PropertyValueSource
Water Solubility678 g/LALOGPS
logP-2.2ALOGPS
logP-2.6ChemAxon
logS0.65ALOGPS
pKa (Strongest Acidic)10.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.6 m³·mol⁻¹ChemAxon
Polarizability13.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H10O5
IUPAC name(3S,4R)-1,3,4,5-tetrahydroxypentan-2-one
InChI IdentifierInChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1
InChI KeyZAQJHHRNXZUBTE-WUJLRWPWSA-N
Isomeric SMILESOC[C@@H](O)[C@H](O)C(=O)CO
Average Molecular Weight150.1299
Monoisotopic Molecular Weight150.05282343
Classification
Description Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSD-Xylulose, non-derivatized, GC-MS Spectrumsplash10-00kb-0930000000-c3a525ee2ad524114f0dSpectrum
Predicted GC-MSD-Xylulose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-9100000000-1304cf35b8860cd7a456Spectrum
Predicted GC-MSD-Xylulose, TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00g3-9127300000-b6aed5448276d0184bc2Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014r-4900000000-0a4d51584b79dc230edbSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-2131da3ca52caffed55fSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-305f431957b24a5b888aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-3e1ebc07944b3d190ec8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-9be7fcf2c9ec6f8829c7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-931753afec5aa068bca8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-1c39b6f316e1745d355cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-9100000000-095c1d8c10895109ecb1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-5ea417513158cb617f30Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID4451524
ChEMBL IDCHEMBL195094
KEGG Compound IDC00310
Pubchem Compound ID5289590
Pubchem Substance IDNot Available
ChEBI ID17140
Phenol-Explorer IDNot Available
DrugBank IDDB03947
HMDB IDHMDB01644
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34575
KNApSAcK IDNot Available
HET IDXUL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDXylulose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Xylulose kinaseXYLBO75191
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference