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Record Information
Version2.0
Created at2020-11-23 18:25:09 UTC
Updated at2024-09-03 04:16:52 UTC
NP-MRD IDNP0002608
Natural Product DOIhttps://doi.org/10.57994/0839
Secondary Accession NumbersNone
Natural Product Identification
Common NameAdonitol
Provided ByBMRBBMRB logo
DescriptionD-Xylitol, also known as xylit or xylo-pentitol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. D-Xylitol is a drug. D-Xylitol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. D-Xylitol, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and hepatocellular carcinoma; D-xylitol has also been linked to the inborn metabolic disorder ribose-5-phosphate isomerase deficiency. Adonitol was first documented in 2000 (PMID: 10747122). Based on a literature review very few articles have been published on D-Xylitol (PMID: 11695131).
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4S)-Pentane-1,2,3,4,5-pentaolChEBI
XylitChEBI
XyliteChEBI
Xylo-pentitolHMDB
XylitolHMDB
D-XYLITOLChEBI
Chemical FormulaC5H12O5
Average Mass152.1458 Da
Monoisotopic Mass152.06847 Da
IUPAC Name(2R,3r,4S)-pentane-1,2,3,4,5-pentol
Traditional Namexylitol
CAS Registry NumberNot Available
SMILES
OC[C@H](O)[C@@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+
InChI KeyHEBKCHPVOIAQTA-SCDXWVJYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduNot AvailableNot Available2023-08-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-14View Spectrum
Species
Species of Origin
Species NameSourceReference
Cannabis sativaCannabisDB
      Not Available
Citrus sinensisKNApSAcK Database
Murraya paniculataKNApSAcK Database
Prunus aviumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point93.00 to 97.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point216.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-2.649 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP-2.5ALOGPS
logP-3.1ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)12.76ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability14.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002917
DrugBank IDDB01904
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001134
KNApSAcK IDC00052270
Chemspider ID6646
KEGG Compound IDC00379
BioCyc IDXYLITOL
BiGG IDNot Available
Wikipedia LinkXylitol
METLIN IDNot Available
PubChem Compound6912
PDB IDNot Available
ChEBI ID17151
Good Scents IDrw1297141
References
General References
  1. Yeo SF, Zhang Y, Schafer D, Campbell S, Wong B: A rapid, automated enzymatic fluorometric assay for determination of D-arabinitol in serum. J Clin Microbiol. 2000 Apr;38(4):1439-43. [PubMed:10747122 ]
  2. Sundaram G, Bartlett D: Preventative measures for bulimic patients with dental erosion. Eur J Prosthodont Restor Dent. 2001 Mar;9(1):25-9. [PubMed:11695131 ]