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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 15:45:05 UTC
NP-MRD IDNP0001416
Secondary Accession NumbersNone
Natural Product 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 human nutrition, the others being galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. (Wikipedia). Xylose in the urine is a biomarker for the consumption of apples and other fruits.
Structure
Thumb
Synonyms
ValueSource
(3R,4S,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetrolChEBI
D-(+)-XyloseChEBI
D-XylopentoseChEBI
Wood sugarChEBI
WURCS=2.0/1,1,0/[a212h-1x_1-5]/1/ChEBI
Xylo-pfanKegg
D-Xylo-pentoseHMDB
XylomedHMDB
XyloseHMDB
XylosideHMDB
XylopyranoseHMDB
D XyloseHMDB
D-XylopyranoseHMDB
Aldehydo-D-xyloseHMDB
D-XyloseChEBI
Chemical FormulaC5H10O5
Average Mass150.1299 Da
Monoisotopic Mass150.05282 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-07-15View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia tortuosaKNApSAcK Database
Allium cepaFooDB
Allium sativumFooDB
Aloe veraKNApSAcK Database
Anacardium occidentaleFooDB
Anagallis arvensisLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apium graveolensFooDB
Arabidopsis thalianaKNApSAcK Database
Artemisia dracunculusFooDB
Ascoseira mirabilisLOTUS Database
Averrhoa carambolaKNApSAcK Database
Beta vulgarisLOTUS Database
Bison bisonFooDB
Bombax ceibaLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
Bubalus bubalisFooDB
Cajanus cajanLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carum carviFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Codonopsis canescensKNApSAcK Database
Codonopsis pilosulaKNApSAcK Database
Codonopsis subglobosaKNApSAcK Database
Codonopsis tangshenKNApSAcK Database
Codonopsis tubulosaKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Diospyros kakiLOTUS Database
Dromaius novaehollandiaeFooDB
Elliottia paniculataLOTUS Database
Equus caballusFooDB
Ficus caricaFooDB
Gallus gallusFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
Hibiscus sabbariffaFooDB
Homo sapiensLOTUS Database
Jatropha gossypifoliaLOTUS Database
Lagopus mutaFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Linum usitatissimumFooDB
Lyonia ovalifoliaLOTUS Database
Malus pumilaFooDB
Matricaria recutitaFooDB
Medicago lupulinaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Moringa oleiferaFooDB
Musa x paradisiacaFooDB
Numida meleagrisFooDB
Ocimum basilicumFooDB
OdocoileusFooDB
OryctolagusFooDB
Oryza sativaFooDB
Ovis ariesFooDB
Panax ginsengKNApSAcK Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaLOTUS Database
Phytolacca americanaFooDB
Prunus armeniacaFooDB
Prunus aviumKNApSAcK Database
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Psidium guajavaFooDB
Ramalina fraxineaLOTUS Database
Rubus idaeusFooDB
Saccharum officinarumLOTUS Database
Sebertia acuminataKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Tamarindus indicaFooDB
Tamarix aphyllaLOTUS Database
Taraxacum officinaleFooDB
Tecoma stansLOTUS Database
Theobroma cacaoFooDB
Trigonella foenum-graecumFooDB
Triticum aestivumFooDB
Typha angustifoliaKNApSAcK Database
Vaccinium oxycoccosLOTUS Database
Vachellia tortuosaLOTUS Database
Vigna radiataFooDB
Vitis vinifera L.FooDB
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90.5 °CNot Available
Boiling Point275.00 to 276.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility555 mg/mLNot Available
LogP5.563 (est)The Good Scents Company Information System
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
HMDB IDHMDB0000098
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005944
KNApSAcK IDC00007290
Chemspider ID119104
KEGG Compound IDC00181
BioCyc IDNot Available
BiGG ID34162
Wikipedia LinkXylose
METLIN ID314
PubChem Compound135191
PDB IDNot Available
ChEBI ID53455
Good Scents IDrw1548081
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Weiner R: [Characteristics of disease and involution-induced changes in intestinal absorption]. Z Alternsforsch. 1986 Jul-Aug;41(4):219-24. [PubMed:3751145 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]