D-Xylose
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Basic Info
Common Name | D-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 ID | F05619 |
CAS Number | 58-86-6 |
PubChem CID | 135191 |
Formula | C5H10O5 |
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 |
Wikipedia | D-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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic oxygen compounds |
Class | Organooxygen compounds |
Subclass | Carbohydrates and carbohydrate conjugates |
Intermediate Tree Nodes | Monosaccharides |
Direct Parent | Pentoses |
Alternative Parents | |
Molecular Framework | Aliphatic heteromonocyclic compounds |
Substituents | Pentose monosaccharide - Oxane - Secondary alcohol - Hemiacetal - Oxacycle - Organoheterocyclic compound - Polyol - Hydrocarbon derivative - Alcohol - Aliphatic heteromonocyclic compound |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 150.13 |
Hydrogen Bond Donor Count | 4 |
Hydrogen Bond Acceptor Count | 5 |
Rotatable Bond Count | 0 |
Complexity | 117 |
Monoisotopic Mass | 150.053 |
Exact Mass | 150.053 |
XLogP | -2.5 |
Formal Charge | 0 |
Heavy Atom Count | 10 |
Defined Atom Stereocenter Count | 3 |
Undefined Atom Stereocenter Count | 1 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB- | 0.5058 |
Human Intestinal Absorption | HIA- | 0.6978 |
Caco-2 Permeability | Caco2- | 0.8326 |
P-glycoprotein Substrate | Non-substrate | 0.6088 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9578 |
Non-inhibitor | 0.9963 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9178 |
Distribution | ||
Subcellular localization | Mitochondria | 0.6529 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8612 |
CYP450 2D6 Substrate | Non-substrate | 0.8864 |
CYP450 3A4 Substrate | Non-substrate | 0.6601 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9791 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9780 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9604 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9760 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9807 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9899 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9815 |
Non-inhibitor | 0.9533 | |
AMES Toxicity | Non AMES toxic | 0.8533 |
Carcinogens | Non-carcinogens | 0.9662 |
Fish Toxicity | Low FHMT | 0.9639 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.8465 |
Honey Bee Toxicity | High HBT | 0.6700 |
Biodegradation | Ready biodegradable | 0.9397 |
Acute Oral Toxicity | IV | 0.4737 |
Carcinogenicity (Three-class) | Non-required | 0.6785 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | 0.4389 | LogS |
Caco-2 Permeability | -0.2683 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.1899 | LD50, mol/kg |
Fish Toxicity | 2.8072 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -1.1294 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Identification of polysaccharides extracted from pea pod by-products andevaluation of their biological and functional properties. | Int J Biol Macromol | 2018 Sep | 29777807 |
Transcriptomic Analysis of Xylan Oligosaccharide Utilization Systems inPediococcus acidilactici Strain BCC-1. | J Agric Food Chem | 2018 May 9 | 29681147 |
Physicochemical, functional, and biological properties of water-solublepolysaccharides from Rosa roxburghii Tratt fruit. | Food Chem | 2018 May 30 | 29407915 |
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 Sci | 2018 May 29 | 29844279 |
Novel Flaxseed Gum Nanocomposites Are Slow Release Iron Supplements. | J Agric Food Chem | 2018 May 23 | 29737167 |
Single-cell Protein and Xylitol Production by a Novel Yeast Strain Candidaintermedia FL023 from Lignocellulosic Hydrolysates and Xylose. | Appl Biochem Biotechnol | 2018 May | 29098561 |
Improving Hydrolysis Characteristics of Xylanases by Site-Directed Mutagenesis inBinding-Site Subsites from Streptomyces L10608. | Int J Mol Sci | 2018 Mar 13 | 29533991 |
Increased sugar yield from pre-milled Douglas-fir forest residuals with lowerenergy consumption by using planetary ball milling. | Bioresour Technol | 2018 Mar | 29272773 |
Differences in Carbohydrates Utilization and Antibiotic Resistance BetweenStreptococcus macedonicus and Streptococcus thermophilus Strains Isolated fromDairy Products in Italy. | Curr Microbiol | 2018 Jun 18 | 29916034 |
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 Prot | 2018 Jun | 29749766 |
The isolation of pentose-assimilating yeasts and their xylose fermentationpotential. | Braz J Microbiol | 2018 Jan - Mar | 28888830 |
Improvement of bread making quality by supplementation with a recombinantxylanase produced by Pichia pastoris. | PLoS One | 2018 Feb 26 | 29481569 |
Restoration of GABA production machinery in Lactobacillus brevis by accessiblecarbohydrates, anaerobiosis and early acidification. | Food Microbiol | 2018 Feb | 28941896 |
Improvement of the catalytic characteristics of a salt-tolerant GH10 xylanasefrom Streptomyce rochei L10904. | Int J Biol Macromol | 2018 Feb | 29030195 |
Pistachio hull water-soluble polysaccharides as a novel prebiotic agent. | Int J Biol Macromol | 2018 Feb | 28928068 |
Disintegration of the agricultural by-product wheat bran under subcriticalconditions. | J Sci Food Agric | 2018 Aug | 29427290 |
Characteristics and intestinal immunomodulating activities of water-solublepectic polysaccharides from Chenpi with different storage periods. | J Sci Food Agric | 2018 Aug | 29330852 |
Enhancement of α,ω-Dicarboxylic Acid Production by the Expression of XyloseReductase for Refactoring Redox Cofactor Regeneration. | J Agric Food Chem | 2018 Apr 4 | 29537267 |
Purification and characterization of novel bi-functional GH3 familyβ-xylosidase/β-glucosidase from Aspergillus niger ADH-11. | Int J Biol Macromol | 2018 Apr 1 | 29174354 |
Anti-fatigue activity of an arabinan-rich pectin from acerola (Malpighiaemarginata). | Int J Biol Macromol | 2018 Apr 1 | 29157904 |
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
- 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
- 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 ]