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Record Information
Version1.0
Creation Date2016-07-13 19:41:06 UTC
Update Date2016-09-23 18:44:33 UTC
LmdbLMDB00042
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Xylose
DescriptionXylose or wood sugar is an aldopentose - a monosaccharide containing five carbon atoms and an aldehyde functional group. It has chemical formula C5H10O5 and is 40% as sweet as sucrose. Xylose is found in the embryos of most edible plants. The polysaccharide xylan, which is closely associated with cellulose, consists practically entirely of d-xylose. Corncobs, cottonseed hulls, pecan shells, and straw contain considerable amounts of this sugar. Xylose is also found in mucopolysaccharides of connective tissue and sometimes in the urine. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore xylose is involved in the biosythetic pathways of most anionic polysaccharides such as heparan sulphate and chondroitin sulphate. In medicine, xylose is used to test for malabsorption by administering a xylose solution to the patient after fasting. If xylose is detected in the blood and/or urine within the next few hours, it has been absorbed by the intestines. Xylose is said to be one of eight sugars which are essential for animal nutrition, the others being galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. (Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(3R,4S,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetrolChEBI
D-(+)-XyloseChEBI
D-XylopentoseChEBI
Wood sugarChEBI
Xylo-pfanKegg
D-xylo-PentoseHMDB
XylomedHMDB
XyloseHMDB, MeSH
XylosideHMDB
XylopyranoseMeSH, HMDB
D XyloseMeSH, HMDB
D-XylopyranoseMeSH, HMDB
D-XyloseChEBI
Aldehydo-D-xyloseHMDB
(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI
D-DulcitolChEBI
D-GalactitolChEBI
DulcitolChEBI
DulcoseChEBI
EuonymitChEBI
L-GalactitolChEBI
MelampyrinChEBI
MelampyritChEBI
Ambap5938HMDB
DulciteHMDB
HexitolHMDB
MelampyriteHMDB
MelampyrumHMDB
Meso-galactitolHMDB
CMPChEBI
CMPChEBI
Cytidine-5'-monophosphateChEBI
Cytidine-5'-monophosphateChEBI
CytidylateChEBI
CytidylateChEBI
Cytidylic acidChEBI
Cytidylic acidChEBI
pCChEBI
pCChEBI
Cytidine-5'-monophosphoric acidGenerator
Cytidine-5'-monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphoric acidHMDB
Cytidine 5'-monophosphoric acidHMDB
5'-CMPHMDB
5'-CMPHMDB
5-CytidylateHMDB
5-CytidylateHMDB
5-Cytidylic acidHMDB
5-Cytidylic acidHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine mono(dihydrogen phosphate)HMDB
Cytidine mono(dihydrogen phosphate)HMDB
Acid, cytidylicHMDB
Acid, cytidylicHMDB
monoPhosphate, cytidineHMDB
monoPhosphate, cytidineHMDB
2' CMPHMDB
2' CMPHMDB
2'-CMPHMDB
2'-CMPHMDB
3' CMPHMDB
3' CMPHMDB
Acids, cytidylicHMDB
Acids, cytidylicHMDB
Cytidylic acidsHMDB
Cytidylic acidsHMDB
3'-CMPHMDB
3'-CMPHMDB
CMPChEBI
CMPChEBI
Cytidine-5'-monophosphateChEBI
Cytidine-5'-monophosphateChEBI
CytidylateChEBI
CytidylateChEBI
Cytidylic acidChEBI
Cytidylic acidChEBI
pCChEBI
pCChEBI
Cytidine-5'-monophosphoric acidGenerator
Cytidine-5'-monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphoric acidHMDB
Cytidine 5'-monophosphoric acidHMDB
5'-CMPHMDB
5'-CMPHMDB
5-CytidylateHMDB
5-CytidylateHMDB
5-Cytidylic acidHMDB
5-Cytidylic acidHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine mono(dihydrogen phosphate)HMDB
Cytidine mono(dihydrogen phosphate)HMDB
Acid, cytidylicHMDB
Acid, cytidylicHMDB
monoPhosphate, cytidineHMDB
monoPhosphate, cytidineHMDB
2' CMPHMDB
2' CMPHMDB
2'-CMPHMDB
2'-CMPHMDB
3' CMPHMDB
3' CMPHMDB
Acids, cytidylicHMDB
Acids, cytidylicHMDB
Cytidylic acidsHMDB
Cytidylic acidsHMDB
3'-CMPHMDB
3'-CMPHMDB
CMPChEBI
Cytidine-5'-monophosphateChEBI
CytidylateChEBI
Cytidylic acidChEBI
pCChEBI
Cytidine-5'-monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphoric acidHMDB
5'-CMPHMDB
5-CytidylateHMDB
5-Cytidylic acidHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine mono(dihydrogen phosphate)HMDB
Acid, cytidylicHMDB
monoPhosphate, cytidineHMDB
2' CMPHMDB
2'-CMPHMDB
3' CMPHMDB
Acids, cytidylicHMDB
Cytidylic acidsHMDB
3'-CMPHMDB
CMPChEBI
Cytidine-5'-monophosphateChEBI
CytidylateChEBI
Cytidylic acidChEBI
pCChEBI
Cytidine-5'-monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphoric acidHMDB
5'-CMPHMDB
5-CytidylateHMDB
5-Cytidylic acidHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine mono(dihydrogen phosphate)HMDB
Acid, cytidylicHMDB
monoPhosphate, cytidineHMDB
2' CMPHMDB
2'-CMPHMDB
3' CMPHMDB
Acids, cytidylicHMDB
Cytidylic acidsHMDB
3'-CMPHMDB
(e)-3-(Methoxycarbonyl)pent-2-enedioic acidGenerator
Chemical FormulaC5H10O5
Average Molecular Weight150.1299
Monoisotopic Molecular Weight150.05282343
IUPAC Name(3R,4S,5R)-oxane-2,3,4,5-tetrol
Traditional Named-xylose
CAS Registry Number58-86-6
SMILES
O[C@@H]1COC(O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1
InChI KeySRBFZHDQGSBBOR-IOVATXLUSA-N
Chemical Taxonomy
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
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.91ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-53943f97f7f99da85d3bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0920000000-c093331f073f56253951Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-53943f97f7f99da85d3bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0920000000-c093331f073f56253951Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9400000000-f20d1c35a7eeea1609a5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00g0-9256300000-ae2d57025e3828494249Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-2900000000-5a95e26ce7a03eeb4a1cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9200000000-ffce45222cab00a0c302Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udr-5900000000-8d1e329345725c7495d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0900000000-4856e933b915ddbb0554Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900000000-79e8278d7ae6b34a7772Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08os-9100000000-64c106194d5825a11d36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-988a7d2dad8bc555d502Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2900000000-31127350481e63c82ff7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-264c06bc93b8e518bbfbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Plasma
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDNot Available
HMDB IDHMDB0060254
FooDB IDFDB005944
Phenol Explorer IDNot Available
KNApSAcK IDC00007290
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkXylose
Chemspider IDNot Available
ChEBI ID53455
PubChem Compound IDNot Available
Kegg Compound IDC00181
YMDB IDYMDB00779
ECMDB IDECMDB00098
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available