Record Information
Version1.0
Creation date2011-09-21 01:38:38 UTC
Update date2015-07-21 06:59:23 UTC
Primary IDFDB028364
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Xylono-1,5-lactone
DescriptionD-xylonolactone is a lactone derivative of xylonic acid. It is an intermediate in the pentose and glucuronate interconversion pathway and can be formed from either D-xylonic acid or D-xylose. D-xylose is a simple 5 carbon sugar that is found in a variety of edible plants. It is also frequently used in intestinal absorption tests to help diagnose problems that prevent the small intestine from absorbing nutrients in food. Xylose is also the first saccharide added to the serine or threonine in the proteoglycan type O-glycosylation and so it is the first saccharide in biosynthetic pathways of most anionic polysaccharides such as heparan sulfate and chondroitin sulfate. D-xylose is normally easily absorbed by the intestines where it can be converted to D-xylonolactone by intestinal D-xylose 1-dehydrogenase (EC 1.1.1.175). [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
D-XylonolactoneChEBI
XylonolactoneHMDB
Predicted Properties
PropertyValueSource
Water Solubility830 g/LALOGPS
logP-2.1ALOGPS
logP-2.1ChemAxon
logS0.75ALOGPS
pKa (Strongest Acidic)11.63ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.82 m³·mol⁻¹ChemAxon
Polarizability12.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O5
IUPAC name(3R,4S,5R)-3,4,5-trihydroxyoxan-2-one
InChI IdentifierInChI=1S/C5H8O5/c6-2-1-10-5(9)4(8)3(2)7/h2-4,6-8H,1H2/t2-,3+,4-/m1/s1
InChI KeyXXBSUZSONOQQGK-FLRLBIABSA-N
Isomeric SMILESO[C@@H]1COC(=O)[C@H](O)[C@H]1O
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
Classification
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassDelta valerolactones
Direct ParentDelta valerolactones
Alternative Parents
Substituents
  • Delta valerolactone
  • Delta_valerolactone
  • Oxane
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSD-Xylono-1,5-lactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9200000000-9be356e915f5897a8457Spectrum
Predicted GC-MSD-Xylono-1,5-lactone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0umr-5393000000-7965b784b3d72826f0d8Spectrum
Predicted GC-MSD-Xylono-1,5-lactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-76be85e7ac9842da922dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0900000000-6503dfb28a322525b19bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6d2c25a921117df43c23Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-553611cef4b5ef504aaaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0092-4900000000-6160c263002249bb2798Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-778239485e740a0bac20Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3900000000-e1d13fcaf4a10f71b067Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-9000000000-6244519c64b48d453565Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-66b1430247d75367a183Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01x0-4900000000-2a8ed88211a98056f83bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-824a8872c2d8c7415b9fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-1f8660ec1076805bcc2dSpectrum
NMRNot Available
ChemSpider ID388758
ChEMBL IDNot Available
KEGG Compound IDC02266
Pubchem Compound ID439692
Pubchem Substance IDNot Available
ChEBI ID15867
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11676
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenaseDHDHQ9UQ10
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference