CHEBI:53455 - D-xylopyranose

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ChEBI Name D-xylopyranose
ChEBI ID CHEBI:53455
ChEBI ASCII Name D-xylopyranose
Definition D-Xylose in its pyranose form.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB52519899, eMolecules:512347, eMolecules:29535916
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Xylose (cf. Ancient Greek: ξύλον, xylon, "wood") is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is derived from hemicellulose, one of the main constituents of biomass. Like most sugars, it can adopt several structures depending on conditions. With its free aldehyde group, it is a reducing sugar.
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Formula C5H10O5
Net Charge 0
Average Mass 150.130
Monoisotopic Mass 150.05282
InChI InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3+,4-,5?/m1/s1
InChIKey SRBFZHDQGSBBOR-IOVATXLUSA-N
SMILES O[C@@H]1COC(O)[C@H](O)[C@H]1O
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via xylose )
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ChEBI Ontology
Outgoing D-xylopyranose (CHEBI:53455) is a D-xylose (CHEBI:65327)
Incoming α-D-Glcp-(1→4)-D-Xylp (CHEBI:153794) has functional parent D-xylopyranose (CHEBI:53455)
β-D-Galp-(1→3)-D-Xylp (CHEBI:148319) has functional parent D-xylopyranose (CHEBI:53455)
β-D-Galp-(1→4)-D-Xylp (CHEBI:148937) has functional parent D-xylopyranose (CHEBI:53455)
β-D-Glcp-(1→2)-D-Xylp (CHEBI:150673) has functional parent D-xylopyranose (CHEBI:53455)
β-D-Glcp-(1→4)-D-Xylp (CHEBI:148105) has functional parent D-xylopyranose (CHEBI:53455)
β-D-GlcpA-(1→4)-D-Xylp (CHEBI:150112) has functional parent D-xylopyranose (CHEBI:53455)
D-Glcp-(1↔1)-D-Xylp (CHEBI:156608) has functional parent D-xylopyranose (CHEBI:53455)
α-D-xylose (CHEBI:28518) is a D-xylopyranose (CHEBI:53455)
β-D-xylose (CHEBI:28161) is a D-xylopyranose (CHEBI:53455)
IUPAC Name
D-xylopyranose
Synonyms Sources
(3R,4S,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrol IUPAC
D-(+)-xylose HMDB
D-xylopentose HMDB
D-xylose ChEBI
D-xylose UniProt
Wood sugar HMDB
Wood sugar KEGG COMPOUND
WURCS=2.0/1,1,0/[a212h-1x_1-5]/1/ GlyTouCan
Manual Xrefs Databases
2854 DrugCentral
C00007290 KNApSAcK
C00181 KEGG COMPOUND
D06346 KEGG DRUG
G53308XG GlyGen
G53308XG GlyTouCan
HMDB0000098 HMDB
Xylose Wikipedia
View more database links
Registry Numbers Types Sources
1280757 Reaxys Registry Number Reaxys
58-86-6 CAS Registry Number KEGG COMPOUND
Citations
Ravi G, Venkatesh YP (2014)
Recognition of riboflavin and the capsular polysaccharide of Haemophilus influenzae type b by antibodies generated to the haptenic epitope D-ribitol.
Glycoconjugate journal 31, 247-258 [PubMed:24643482]
[show Abstract]
Ravi G, Venkatesh YP (2014)
Recognition of flavin mononucleotide, Haemophilus influenzae type b and its capsular polysaccharide vaccines by antibodies specific to D-ribitol-5-phosphate.
Glycoconjugate journal 31, 573-585 [PubMed:25108762]
[show Abstract]
Hector RE, Dien BS, Cotta MA, Mertens JA (2013)
Growth and fermentation of D-xylose by Saccharomyces cerevisiae expressing a novel D-xylose isomerase originating from the bacterium Prevotella ruminicola TC2-24.
Biotechnology for biofuels 6, 84 [PubMed:23721368]
[show Abstract]
Hricovíniová Z (2013)
Xylans are a valuable alternative resource: production of D-xylose, D-lyxose and furfural under microwave irradiation.
Carbohydrate polymers 98, 1416-1421 [PubMed:24053822]
[show Abstract]
Wu T, Bound MJ, Zhao BR, Standfield SD, Bellon M, Jones KL, Horowitz M, Rayner CK (2013)
Effects of a D-xylose preload with or without sitagliptin on gastric emptying, glucagon-like peptide-1, and postprandial glycemia in type 2 diabetes.
Diabetes care 36, 1913-1918 [PubMed:23359361]
[show Abstract]
Brat D, Boles E (2013)
Isobutanol production from D-xylose by recombinant Saccharomyces cerevisiae.
FEMS yeast research 13, 241-244 [PubMed:23279585]
[show Abstract]
Morais CG, Cadete RM, Uetanabaro AP, Rosa LH, Lachance MA, Rosa CA (2013)
D-xylose-fermenting and xylanase-producing yeast species from rotting wood of two Atlantic Rainforest habitats in Brazil.
Fungal genetics and biology : FG & B 60, 19-28 [PubMed:23872280]
[show Abstract]
Peña I, Mata S, Martín A, Cabezas C, Daly AM, Alonso JL (2013)
Conformations of D-xylose: the pivotal role of the intramolecular hydrogen-bonding.
Physical chemistry chemical physics : PCCP 15, 18243-18248 [PubMed:24065156]
[show Abstract]
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
Sreenath K, Venkatesh YP (2007)
Reductively aminated D-xylose-albumin conjugate as the immunogen for generation of IgG and IgE antibodies specific to D-xylitol, a haptenic allergen.
Bioconjugate chemistry 18, 1995-2003 [PubMed:17979222]
[show Abstract]
Mizobe T, Ando M, Yamasaki H, Onoue K, Misaki A (1995)
Purification and characterization of the serotype-specific polysaccharide antigen of Trichosporon cutaneum serotype II: a disease-related antigen of Japanese summer-type hypersensitivity pneumonitis.
Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 25, 265-272 [PubMed:7540499]
[show Abstract]
WENNIG F (1956)
[Metabolic studies on D-xylose, a pentose sugar].
Wiener klinische Wochenschrift 68, 248-251 [PubMed:13338266]
Last Modified
02 August 2021