D-Xylose (CED0001339)

Record Information
Version1.0
Creation Date2014-09-11 05:22:47 UTC
Update Date2026-05-14 19:05:57 UTC
Accession NumberCHEM003882
Identification
Common NameD-Xylose
ClassSmall Molecule
Description
D-Xylose belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. This exogenous compound has the chemical formula C5H10O5 and an average molecular weight of 150.13 g/mol. At room temperature, it exists as a solid. In the body, it has been detected in the small intestine and erythrocytes. Its recorded protein targets include the progesterone receptor (PGR) and the androgen receptor (AR). D-Xylose is found in 18 recorded sources. These include drinking water and water supply, as well as building and construction materials such as fencing. It is associated with food, food processing, and cookware, including the preparation of wine or sparkling wine, preparation of vinegar, preparation of malt, molasses and treatment of molasses, and agglomerated sugar products. It is also found in electrical and electronic equipment, such as video games, antennas, amplifiers, sparking plugs, and line transmission systems, as well as household cleaning and consumer products, including tobacco product cases, other smoking requisites, and non electric simulated smoking devices. The recorded exposure route for this compound is oral. Industrially, D-Xylose is used as a deodorizer, humectant, flavouring and nutrient, and as a softener and conditioner (PMC9049632). Additionally, it serves as a nutrient in environmental contexts (PMC9049632).
Contaminant Type
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
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
XylosideHMDB
XylopyranoseHMDB
D XyloseHMDB
D-XylopyranoseHMDB
Aldehydo-D-xyloseHMDB
D-XyloseChEBI
Chemical FormulaC5H10O5
Average Molecular Mass150.130 g/mol
Monoisotopic Mass150.053 g/mol
CAS Registry Number58-86-6
IUPAC Name(3R,4S,5R)-oxane-2,3,4,5-tetrol
Traditional Named-xylose
SMILESO[C@@H]1COC(O)[C@H](O)[C@H]1O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Erythrocyte
  • Small Intestine
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point90.5 °C
Boiling PointNot Available
Solubility555.0 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility1220 g/LALOGPS
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 KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0udi-0920000000-53943f97f7f99da85d3bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uxr-0920000000-c093331f073f56253951Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-0920000000-53943f97f7f99da85d3bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0uxr-0920000000-c093331f073f56253951Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000x-9400000000-f20d1c35a7eeea1609a5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00g0-9256300000-ae2d57025e3828494249Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2900000000-5a95e26ce7a03eeb4a1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kr-9200000000-ffce45222cab00a0c302Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udr-5900000000-8d1e329345725c7495d0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0c09-9300000000-68bb5f7897018aa0f358Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-f76bfc808747fe9aad84Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-a7b4fd29d3979cb7bf06Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9100000000-509fbbf4a256fe9f3700Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-9200000000-7c094cf44853525b1af6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-b22a8f9c232e806e5c66Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-0900000000-4856e933b915ddbb0554Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0900000000-79e8278d7ae6b34a7772Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08os-9100000000-64c106194d5825a11d36Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1900000000-988a7d2dad8bc555d502Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-2900000000-31127350481e63c82ff7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-264c06bc93b8e518bbfbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gc0-1900000000-e784a3fdca89dcb59c12Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0m4p-9100000000-fc295e2732f55a0a18c1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-9000000000-ba5f29c2c79df8d0956fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-7900000000-524214992b29f1ff9b80Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-f758a7d33dac04b06275Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-4b3e154b12c2ee07bf58Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6622.0Log mg/kg[3700:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
496FencingBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAlpha-galactosidase CQ9UUZ4Aspergillus nigerPredicted (SEA)2.49118
Click to view 3D structureBeta-galactosidaseP29853Aspergillus nigerPredicted (SEA)1.16774
Lysosomal alpha-glucosidase structureClick to view 3D structureLysosomal alpha-glucosidaseP10253HumansPredicted (SEA)6.85073
Maltase-glucoamylase structureClick to view 3D structureMaltase-glucoamylaseO43451HumansPredicted (SEA)12.2223
Click to view 3D structureSucrase-isomaltase, intestinalP23739Rattus norvegicusPredicted (SEA)8.56341
Sucrase-isomaltase, intestinal structureClick to view 3D structureSucrase-isomaltase, intestinalP14410HumansPredicted (SEA)6.15009
Lysosomal acid glucosylceramidase structureClick to view 3D structureLysosomal acid glucosylceramidaseP04062HumansPredicted (SEA)28.9599
Click to view 3D structureGlycogen debranching enzymeP35573HumansPredicted (SEA)4.35956
Click to view 3D structureLysosomal alpha-glucosidaseQ6P7A9Rattus norvegicusPredicted (SEA)8.87481
Click to view 3D structureNeutral alpha-glucosidase CQ8BVW0Mus musculusPredicted (SEA)3.42537
Click to view 3D structureLactase/phlorizin hydrolaseQ02401Rattus norvegicusPredicted (SEA)3.97031
Click to view 3D structurePlasma alpha-L-fucosidaseQ9BTY2HumansPredicted (SEA)2.72472
Click to view 3D structureAlpha-glucosidaseQ9LGC6Oryza sativa Japonica GroupPredicted (SEA)4.7488
Click to view 3D structureAlpha-mannosidase 2C1P21139Rattus norvegicusPredicted (SEA)1.40129
Click to view 3D structureAlpha-galactosidaseQ42656Coffea arabicaPredicted (SEA)10.9767
Click to view 3D structureNon-lysosomal glucosylceramidaseQ69ZF3Mus musculusPredicted (SEA)9.18621
Click to view 3D structureAlpha-1,2-mannosidase (BT_3990)Q8A0N1Bacteroides thetaiotaomicronPredicted (SEA)4.35956
Click to view 3D structureNon-lysosomal glucosylceramidaseQ9HCG7HumansPredicted (SEA)55.8179
Tissue alpha-L-fucosidase structureClick to view 3D structureTissue alpha-L-fucosidaseP04066HumansPredicted (SEA)5.2159
Click to view 3D structureGlycogen debranching enzymeP35574Oryctolagus cuniculusPredicted (SEA)4.7488
Click to view 3D structureAlpha-glucosidase MAL62P07265Saccharomyces cerevisiaePredicted (SEA)4.35956
Click to view 3D structureBeta-galactosidaseQ58D55Bos taurusPredicted (SEA)27.5586
Click to view 3D structureCeramide glucosyltransferaseO88693Mus musculusPredicted (SEA)65.6269
Click to view 3D structureTrehalaseO43280HumansPredicted (SEA)14.7135
Click to view 3D structureBeta-galactosidaseD3ZUM4Rattus norvegicusPredicted (SEA)4.12601
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansKnownNot Available
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0000098
FooDB IDFDB005944
Phenol Explorer IDNot Available
KNApSAcK IDC00007290
BiGG ID34162
BioCyc IDNot Available
METLIN ID314
PDB IDNot Available
Wikipedia LinkXylose
Chemspider ID119104
ChEBI ID53455
PubChem Compound ID135191
Kegg Compound IDC00181
YMDB IDYMDB00779
ECMDB IDECMDB00098
References
Synthesis ReferenceLavarack, 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.
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13338266
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17979222
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23279585
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23359361
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23721368
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23872280
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24053822
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24065156
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24643482
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=25108762
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=7540499
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. Weiner R, Laue R, Dietze F: [Enteral resorption kinetics in the aging process]. Z Gesamte Inn Med. 1986 Mar 1;41(5):152-8.
21. 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.
22. Weiner R: [Characteristics of disease and involution-induced changes in intestinal absorption]. Z Alternsforsch. 1986 Jul-Aug;41(4):219-24.
23. Weiner R, Laue R, Dietze F, Hartig W: A modified D-xylose absorption test. Infusionsther Klin Ernahr. 1984 Dec;11(6):333-7.
24. 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.
25. 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.
26. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.