Basic Info

Common NameD-Xylose(F05619)
2D Structure
Description

Xylose 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).

FRCD IDF05619
CAS Number58-86-6
PubChem CID135191
FormulaC5H10O5
IUPAC Name

(3R,4S,5R)-oxane-2,3,4,5-tetrol

InChI Key

SRBFZHDQGSBBOR-IOVATXLUSA-N

InChI

InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1

Canonical SMILES

C1C(C(C(C(O1)O)O)O)O

Isomeric SMILES

C1[C@H]([C@@H]([C@H](C(O1)O)O)O)O

WikipediaD-Xylose
Synonyms
        
            D-Xylopyranose
        
            (3R,4S,5R)-oxane-2,3,4,5-tetrol
        
            D-Xylose
        
            Xylose
        
            Xyloside
        
            Wood sugar
        
            Xylopyranose
        
            D-xylopentose
        
            CHEBI:53455
        
            Xylopyranoside
        
Classifies
                

                  
                    Plant Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbohydrates and carbohydrate conjugates
Intermediate Tree NodesMonosaccharides
Direct ParentPentoses
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsPentose monosaccharide - Oxane - Secondary alcohol - Hemiacetal - Oxacycle - Organoheterocyclic compound - Polyol - Hydrocarbon derivative - Alcohol - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Properties

Property NameProperty Value
Molecular Weight150.13
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Complexity117
Monoisotopic Mass150.053
Exact Mass150.053
XLogP-2.5
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.5058
Human Intestinal AbsorptionHIA-0.6978
Caco-2 PermeabilityCaco2-0.8326
P-glycoprotein SubstrateNon-substrate0.6088
P-glycoprotein InhibitorNon-inhibitor0.9578
Non-inhibitor0.9963
Renal Organic Cation TransporterNon-inhibitor0.9178
Distribution
Subcellular localizationMitochondria0.6529
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8612
CYP450 2D6 SubstrateNon-substrate0.8864
CYP450 3A4 SubstrateNon-substrate0.6601
CYP450 1A2 InhibitorNon-inhibitor0.9791
CYP450 2C9 InhibitorNon-inhibitor0.9780
CYP450 2D6 InhibitorNon-inhibitor0.9604
CYP450 2C19 InhibitorNon-inhibitor0.9760
CYP450 3A4 InhibitorNon-inhibitor0.9807
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9899
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9815
Non-inhibitor0.9533
AMES ToxicityNon AMES toxic0.8533
CarcinogensNon-carcinogens0.9662
Fish ToxicityLow FHMT0.9639
Tetrahymena Pyriformis ToxicityLow TPT0.8465
Honey Bee ToxicityHigh HBT0.6700
BiodegradationReady biodegradable0.9397
Acute Oral ToxicityIV0.4737
Carcinogenicity (Three-class)Non-required0.6785

Model Value Unit
Absorption
Aqueous solubility0.4389LogS
Caco-2 Permeability-0.2683LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.1899LD50, mol/kg
Fish Toxicity2.8072pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.1294pIGC50, ug/L

References

TitleJournalDatePubmed ID
Identification of polysaccharides extracted from pea pod by-products andevaluation of their biological and functional properties.Int J Biol Macromol2018 Sep29777807
Transcriptomic Analysis of Xylan Oligosaccharide Utilization Systems inPediococcus acidilactici Strain BCC-1.J Agric Food Chem2018 May 929681147
Physicochemical, functional, and biological properties of water-solublepolysaccharides from Rosa roxburghii Tratt fruit.Food Chem2018 May 3029407915
UDP-Glucose 4-Epimerase and β-1,4-Galactosyltransferase from the Oyster Magallanagigas as Valuable Biocatalysts for the Production of Galactosylated Products.Int J Mol Sci2018 May 2929844279
Novel Flaxseed Gum Nanocomposites Are Slow Release Iron Supplements.J Agric Food Chem2018 May 2329737167
Single-cell Protein and Xylitol Production by a Novel Yeast Strain Candidaintermedia FL023 from Lignocellulosic Hydrolysates and Xylose.Appl Biochem Biotechnol2018 May29098561
Improving Hydrolysis Characteristics of Xylanases by Site-Directed Mutagenesis inBinding-Site Subsites from Streptomyces L10608.Int J Mol Sci2018 Mar 1329533991
Increased sugar yield from pre-milled Douglas-fir forest residuals with lowerenergy consumption by using planetary ball milling.Bioresour Technol2018 Mar29272773
Differences in Carbohydrates Utilization and Antibiotic Resistance BetweenStreptococcus macedonicus and Streptococcus thermophilus Strains Isolated fromDairy Products in Italy.Curr Microbiol2018 Jun 1829916034
Evaluation of the Impact of Varied Carvacrol Concentrations on SalmonellaRecovery in Oregano and How Corn Oil Can Minimize the Effect of Carvacrol during Preenrichment.J Food Prot2018 Jun29749766
The isolation of pentose-assimilating yeasts and their xylose fermentationpotential.Braz J Microbiol2018 Jan - Mar28888830
Improvement of bread making quality by supplementation with a recombinantxylanase produced by Pichia pastoris.PLoS One2018 Feb 2629481569
Restoration of GABA production machinery in Lactobacillus brevis by accessiblecarbohydrates, anaerobiosis and early acidification.Food Microbiol2018 Feb28941896
Improvement of the catalytic characteristics of a salt-tolerant GH10 xylanasefrom Streptomyce rochei L10904.Int J Biol Macromol2018 Feb29030195
Pistachio hull water-soluble polysaccharides as a novel prebiotic agent.Int J Biol Macromol2018 Feb28928068
Disintegration of the agricultural by-product wheat bran under subcriticalconditions.J Sci Food Agric2018 Aug29427290
Characteristics and intestinal immunomodulating activities of water-solublepectic polysaccharides from Chenpi with different storage periods.J Sci Food Agric2018 Aug29330852
Enhancement of α,ω-Dicarboxylic Acid Production by the Expression of XyloseReductase for Refactoring Redox Cofactor Regeneration.J Agric Food Chem2018 Apr 429537267
Purification and characterization of novel bi-functional GH3 familyβ-xylosidase/β-glucosidase from Aspergillus niger ADH-11.Int J Biol Macromol2018 Apr 129174354
Anti-fatigue activity of an arabinan-rich pectin from acerola (Malpighiaemarginata).Int J Biol Macromol2018 Apr 129157904

Targets

General Function:
Zinc ion binding
Specific Function:
The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor isoform B (PRB) is involved activation of c-SRC/MAPK signaling on hormone stimulation.Isoform A: inactive in stimulating c-Src/MAPK signaling on hormone stimulation.Isoform 4: Increases mitochondrial membrane potential and cellular respiration upon stimulation by progesterone.
Gene Name:
PGR
Uniprot ID:
P06401
Molecular Weight:
98979.96 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]