Showing Compound Card for D-Xylose (CDB000141)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:26:18 UTC
Updated at2020-11-18 16:34:50 UTC
CannabisDB IDCDB000141
Secondary Accession NumbersNot Available
Cannabis Compound 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. It is a white powder with a smoky odor and a smoky sweet salty coffee taste ( Ref:DOI ). The polysaccharide xylan, a hemi-cellulose, consists almost entirely of D-xylose. Xylan is found in 30 % of most plants. Xylose, though, is pervasive as it is found in the embryos of most edible plants. Corncobs, cottonseed hulls, pecan shells, and straw contain considerable amounts of this sugar as well as the plants of apple, apricot, caper, celery, fenugreek and wheat. It is found in apple, banana, grape, guava, orange, raspberry and plum ( Ref:DOI ). Xylose in the urine is a biomarker for the consumption of apples and other fruits. Xylose is also found in mucopolysaccharides of connective tissue. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore, xylose is involved in the biosynthetic 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 including galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. Being part of the cell wall of most plants, xylan and xylose are also found in Cannabis sativa tissue (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC5H10O5
Average Molecular Weight150.13
Monoisotopic Molecular Weight150.0528
IUPAC Name(2R,3R,4S,5R)-oxane-2,3,4,5-tetrol
Traditional Nameβ-D-xylose
CAS Registry Number2460-44-8
SMILES
O[C@@H]1CO[C@@H](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-KKQCNMDGSA-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
Not Available
Physical Properties
StateSolid
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSD-Xylose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000x-9400000000-f20d1c35a7eeea1609a5Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0900000000-4856e933b915ddbb05542017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0900000000-79e8278d7ae6b34a77722017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08os-9100000000-64c106194d5825a11d362017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-988a7d2dad8bc555d5022017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-2900000000-31127350481e63c82ff72017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-264c06bc93b8e518bbfb2017-10-06View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0062087
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031294
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02096
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound125409
PDB IDNot Available
ChEBI ID28161
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]