Record Information
Version2.0
Creation Date2012-05-31 09:57:17 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00098
Identification
Name:D-Xylose
Description:Xylose 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 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.
Structure
Thumb
Synonyms:
  • α-D-xylose
  • a-D-Xylose
  • Alpha-D-Xylose
  • D-(+)-Xylose
  • D-Xylo-pentose
  • D-Xylose
  • Wood sugar
  • Xylo-pfan
  • Xylomed
  • Xylose
  • Xyloside
  • α-D-Xylose
Chemical Formula:C5H10O5
Weight:Average: 150.1299
Monoisotopic: 150.05282343
InChI Key:SRBFZHDQGSBBOR-IOVATXLUSA-N
InChI:InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1
CAS number:58-86-6
IUPAC Name:(3R,4S,5R)-oxane-2,3,4,5-tetrol
Traditional IUPAC Name:d-xylose
SMILES:O[C@@H]1COC(O)[C@H](O)[C@H]1O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
Physical Properties
State:Solid
Charge:0
Melting point:90.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:555.0 mg/mL [MERCK INDEX (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1220.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.96 m3·mol-1ChemAxon
Polarizability13.44 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Starch and sucrose metabolismPW000941 Pw000941Pw000941 greyscalePw000941 simple
KEGG Pathways:
  • ABC transporters ec02010
  • Amino sugar and nucleotide sugar metabolism ec00520
  • Pentose and glucuronate interconversions ec00040
  • Starch and sucrose metabolism ec00500
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-000x-9400000000-f20d1c35a7eeea1609a5View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00g0-9256300000-ae2d57025e3828494249View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-2900000000-5a95e26ce7a03eeb4a1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kr-9200000000-ffce45222cab00a0c302View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udr-5900000000-8d1e329345725c7495d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0900000000-4856e933b915ddbb0554View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900000000-79e8278d7ae6b34a7772View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08os-9100000000-64c106194d5825a11d36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-988a7d2dad8bc555d502View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2900000000-31127350481e63c82ff7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-264c06bc93b8e518bbfbView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Ehrenpreis ED, Salvino M, Craig RM: Improving the serum D-xylose test for the identification of patients with small intestinal malabsorption. J Clin Gastroenterol. 2001 Jul;33(1):36-40. Pubmed: 11418788
  • Horvath K, Horn G, Bingadeem H, Nemes Nagy A, Bodanszky H: [The value of the d-xylose loading test in the diagnosis of malabsorption syndromes] Orv Hetil. 1990 Aug 19;131(33):1803-6, 1809. Pubmed: 2204861
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Kost S, Keinert K, Glaser FH: [D-xylose test of resorption as a method to determine radiation side effects in the small intestine] Strahlenther Onkol. 1998 Sep;174(9):462-7. Pubmed: 9765687
  • Molina JM, Tourneur M, Sarfati C, Chevret S, de Gouvello A, Gobert JG, Balkan S, Derouin F: Fumagillin treatment of intestinal microsporidiosis. N Engl J Med. 2002 Jun 20;346(25):1963-9. Pubmed: 12075057
  • Saliba F, Hagipantelli R, Misset JL, Bastian G, Vassal G, Bonnay M, Herait P, Cote C, Mahjoubi M, Mignard D, Cvitkovic E: Pathophysiology and therapy of irinotecan-induced delayed-onset diarrhea in patients with advanced colorectal cancer: a prospective assessment. J Clin Oncol. 1998 Aug;16(8):2745-51. Pubmed: 9704727
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Wang SC, You RD: [Clinical and experimental study on treatment of anorexy in children with the activating spleen prescription] Zhong Xi Yi Jie He Za Zhi. 1991 Feb;11(2):75-8, 67. Pubmed: 2060054
  • Weiner R, Dietze F, Laue R: Age-dependent alterations of intestinal absorption. II. A clinical study using a modified D-xylose absorption test. Arch Gerontol Geriatr. 1984 Jul;3(2):97-108. Pubmed: 6548110
  • Weiner R, Laue R, Dietze F, Hartig W: A modified D-xylose absorption test. Infusionsther Klin Ernahr. 1984 Dec;11(6):333-7. Pubmed: 6526497
  • Weiner R, Laue R, Dietze F: [Enteral resorption kinetics in the aging process] Z Gesamte Inn Med. 1986 Mar 1;41(5):152-8. Pubmed: 3716508
  • Weiner R: [Characteristics of disease and involution-induced changes in intestinal absorption] ZFA. 1986 Jul-Aug;41(4):219-24. Pubmed: 3751145
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Lavarack, B. P.; Griffin, G.; Rodman, D. Optimizing the autohydrolysis of bagasse to extract D-xylose. Proceedings of the Conference of the Australian Society of Sugar Cane Technologists (1999), 21st 394-400.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15936
HMDB IDHMDB00098
Pubchem Compound ID135191
Kegg IDC00181
ChemSpider ID119104
WikipediaXylose
BioCyc IDXYLOSE
EcoCyc IDXYLOSE

Enzymes

General function:
Involved in xylose isomerase activity
Specific function:
D-xylose = D-xylulose
Gene Name:
xylA
Uniprot ID:
P00944
Molecular weight:
49742
Reactions
D-xylose = D-xylulose.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex XylFGH involved in xylose import. Responsible for energy coupling to the transport system (Probable). The XylFGH system can also transport ribose in absence of xylose
Gene Name:
xylG
Uniprot ID:
P37388
Molecular weight:
56470
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of (1->4)-beta-D-xylans, to remove successive D-xylose residues from the non-reducing termini
Gene Name:
yagH
Uniprot ID:
P77713
Molecular weight:
60825
Reactions
Hydrolysis of (1->4)-beta-D-xylans, to remove successive D-xylose residues from the non-reducing termini.
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for D-xylose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
xylH
Uniprot ID:
P0AGI4
Molecular weight:
41030
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the high-affinity D-xylose membrane transport system. Binds with high affinity to xylose
Gene Name:
xylF
Uniprot ID:
P37387
Molecular weight:
35734

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex XylFGH involved in xylose import. Responsible for energy coupling to the transport system (Probable). The XylFGH system can also transport ribose in absence of xylose
Gene Name:
xylG
Uniprot ID:
P37388
Molecular weight:
56470
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in transmembrane transporter activity
Specific function:
Uptake of D-xylose across the boundary membrane with the concomitant transport of protons into the cell (symport system)
Gene Name:
xylE
Uniprot ID:
P0AGF4
Molecular weight:
53608
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for D-xylose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
xylH
Uniprot ID:
P0AGI4
Molecular weight:
41030
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the high-affinity D-xylose membrane transport system. Binds with high affinity to xylose
Gene Name:
xylF
Uniprot ID:
P37387
Molecular weight:
35734
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368