Showing Compound Card for xylan (CDB006125)

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Record Information
Version1.0
Created at2020-06-15 21:22:16 UTC
Updated at2020-11-18 16:40:13 UTC
CannabisDB IDCDB006125
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namexylan
DescriptionXylan is a group of hemicelluloses, representing the third most abundant biopolymer on Earth. It is found in plants, in the secondary cell walls of dicotyledonous plants and in all cell walls of grasses (monocotyledonous). Xylans are polysaccharides made up of β-1,4-linked xylose (a pentose sugar) residues with side branches of α-arabinofuranose and α-glucuronic acids and contribute to cross-linking of cellulose microfibrils and lignin through ferulic acid residues. On the basis of the substituting groups, xylan can be categorized into three classes i) glucuronoxylan (GX) ii) neutral arabinoxylan (AX) and iii) glucuronoarabinoxylan (GAX). The quality of cereal flours and the hardness of dough are largely affected by the amount of xylan. Xylan is one of the foremost anti-nutritional factors in commonly used feedstuff raw materials. It is a major component of plant secondary cell walls which is a major source of renewable energy especially for second generation biofuels. However, since microorganisms like yeast cannot ferment pentoses naturally, xylose (the pentose backbone of xylan) results hard to ferment in biofuel production, reducing its use in renewable energy production (PMID: 18299887 , PMID: 31077637 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC5H10O6
Average Molecular Weight166.13
Monoisotopic Molecular Weight166.0477
IUPAC Name(2R,3R,5S,6S)-oxane-2,3,4,5,6-pentol
Traditional Name(2R,3R,5S,6S)-oxane-2,3,4,5,6-pentol
CAS Registry NumberNot Available
SMILES
[H][C@]1(O)O[C@@]([H])(O)[C@]([H])(O)C([H])(O)[C@]1([H])O
InChI Identifier
InChI=1S/C5H10O6/c6-1-2(7)4(9)11-5(10)3(1)8/h1-10H/t1?,2-,3+,4-,5+
InChI KeyHEHIOFQJTRFOKM-ASQQECOQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point>180°CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.8ALOGPS
logP-2.7ChemAxon
logS0.58ALOGPS
pKa (Strongest Acidic)10.96ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.99 m³·mol⁻¹ChemAxon
Polarizability14.4 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-db3bbca86ffbe5ccb5072016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-8c7369260be1e74215792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9200000000-5510bd4bc1e402672e4e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3900000000-6867c897fc2ef713be702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-6900000000-9607d4adc081c6a76ffc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9000000000-a714e9a7f5c662ae8cf92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ls-0900000000-07b3144a15c464d1dae22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02mv-9300000000-3d627eb196d3246409c62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c04-9100000000-a007f91b535660d38f122021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-711965af16c8cc42b8e02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9000000000-d5147bb994e25710f5042021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b8acd7efa0721e83a8d92021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0301774
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001133
KNApSAcK IDNot Available
Chemspider ID59696179
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound50909243
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Blake AW, Marcus SE, Copeland JE, Blackburn RS, Knox JP: In situ analysis of cell wall polymers associated with phloem fibre cells in stems of hemp, Cannabis sativa L. Planta. 2008 Jun;228(1):1-13. doi: 10.1007/s00425-008-0713-5. Epub 2008 Feb 26. [PubMed:18299887 ]
  2. Oliveira DM, Mota TR, Salatta FV, Marchiosi R, Gomez LD, McQueen-Mason SJ, Ferrarese-Filho O, Dos Santos WD: Designing xylan for improved sustainable biofuel production. Plant Biotechnol J. 2019 Dec;17(12):2225-2227. doi: 10.1111/pbi.13150. Epub 2019 Sep 30. [PubMed:31077637 ]