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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-02-04 10:13:48 UTC
Update Date2021-09-14 15:19:57 UTC
HMDB IDHMDB0011676
Secondary Accession Numbers
  • HMDB11676
Metabolite Identification
Common 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).
Structure
Data?1582752937
Synonyms
ValueSource
D-XylonolactoneChEBI
XylonolactoneHMDB
Chemical FormulaC5H8O5
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
IUPAC Name(3R,4S,5R)-3,4,5-trihydroxyoxan-2-one
Traditional NameD-xylonolactone
CAS Registry NumberNot Available
SMILES
O[C@@H]1COC(=O)[C@H](O)[C@H]1O
InChI Identifier
InChI=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
Chemical Taxonomy
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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.84331661259
DarkChem[M-H]-126.79731661259
DeepCCS[M+H]+134.17330932474
DeepCCS[M-H]-132.05730932474
DeepCCS[M-2H]-167.0630932474
DeepCCS[M+Na]+140.99230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-Xylono-1,5-lactoneO[C@@H]1COC(=O)[C@H](O)[C@H]1O2724.9Standard polar33892256
D-Xylono-1,5-lactoneO[C@@H]1COC(=O)[C@H](O)[C@H]1O1343.0Standard non polar33892256
D-Xylono-1,5-lactoneO[C@@H]1COC(=O)[C@H](O)[C@H]1O1516.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Xylono-1,5-lactone,1TMS,isomer #1C[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@H]1O1461.3Semi standard non polar33892256
D-Xylono-1,5-lactone,1TMS,isomer #2C[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O)[C@@H]1O1499.2Semi standard non polar33892256
D-Xylono-1,5-lactone,1TMS,isomer #3C[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@@H]1O1493.5Semi standard non polar33892256
D-Xylono-1,5-lactone,2TMS,isomer #1C[Si](C)(C)O[C@@H]1COC(=O)[C@H](O[Si](C)(C)C)[C@H]1O1574.7Semi standard non polar33892256
D-Xylono-1,5-lactone,2TMS,isomer #2C[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@H]1O[Si](C)(C)C1533.6Semi standard non polar33892256
D-Xylono-1,5-lactone,2TMS,isomer #3C[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@@H]1O[Si](C)(C)C1561.9Semi standard non polar33892256
D-Xylono-1,5-lactone,3TMS,isomer #1C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)COC(=O)[C@@H]1O[Si](C)(C)C1608.1Semi standard non polar33892256
D-Xylono-1,5-lactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@H]1O1717.6Semi standard non polar33892256
D-Xylono-1,5-lactone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O)[C@@H]1O1731.6Semi standard non polar33892256
D-Xylono-1,5-lactone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@@H]1O1733.7Semi standard non polar33892256
D-Xylono-1,5-lactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2008.1Semi standard non polar33892256
D-Xylono-1,5-lactone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C1977.3Semi standard non polar33892256
D-Xylono-1,5-lactone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@@H]1O[Si](C)(C)C(C)(C)C1982.9Semi standard non polar33892256
D-Xylono-1,5-lactone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)COC(=O)[C@@H]1O[Si](C)(C)C(C)(C)C2255.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - D-Xylono-1,5-lactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9200000000-9be356e915f5897a84572017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Xylono-1,5-lactone GC-MS (3 TMS) - 70eV, Positivesplash10-0umr-5393000000-7965b784b3d72826f0d82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Xylono-1,5-lactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 10V, Positive-QTOFsplash10-000t-0900000000-76be85e7ac9842da922d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 20V, Positive-QTOFsplash10-001j-0900000000-6503dfb28a322525b19b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 40V, Positive-QTOFsplash10-0006-9000000000-6d2c25a921117df43c232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 10V, Negative-QTOFsplash10-0002-1900000000-553611cef4b5ef504aaa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 20V, Negative-QTOFsplash10-0092-4900000000-6160c263002249bb27982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 40V, Negative-QTOFsplash10-0006-9000000000-778239485e740a0bac202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 10V, Negative-QTOFsplash10-0002-3900000000-e1d13fcaf4a10f71b0672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 20V, Negative-QTOFsplash10-052f-9000000000-6244519c64b48d4535652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 40V, Negative-QTOFsplash10-0a4l-9000000000-66b1430247d75367a1832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 10V, Positive-QTOFsplash10-01x0-4900000000-2a8ed88211a98056f83b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 20V, Positive-QTOFsplash10-00di-9000000000-824a8872c2d8c7415b9f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Xylono-1,5-lactone 40V, Positive-QTOFsplash10-0006-9000000000-1f8660ec1076805bcc2d2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028364
KNApSAcK IDNot Available
Chemspider ID388758
KEGG Compound IDC02266
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439692
PDB IDNot Available
ChEBI ID15867
Food Biomarker OntologyNot Available
VMH IDM01757
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
DHDH
Uniprot ID:
Q9UQ10
Molecular weight:
36381.705
Reactions
D-Xylose + NADP → D-Xylono-1,5-lactone + NADPHdetails
D-Xylose + NADP → D-Xylono-1,5-lactone + NADPH + Hydrogen Iondetails