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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:56 UTC
Update Date2021-09-14 15:19:57 UTC
HMDB IDHMDB0002541
Secondary Accession Numbers
  • HMDB02541
Metabolite Identification
Common NameGalactonolactone
DescriptionGalactonolactone has been determined in human urine by reversed-phase HPLC for the specific evaluation of metabolic by-products in the urine of galactosemic patients and based on the simultaneous determination of gluconolactone, galactonolactone and galactitol. (PMID: 1797843 ). Patients with galactose-1-phosphate uridyltransferase (GALT) deficiency, given a load of galactose have been shown to excrete six times as much galactonate in their urine as normal subjects exposed to the same experimental conditions. The production of galactonate occurs through the activity of a soluble NAD+-dependent galactose dehydrogenase, catalyzing the conversion of galactose to D-galactonolactone (D-galactose: NAD+ oxidoreductase, EC 1.1.1.48). (OMMBID).
Structure
Data?1582752252
Synonyms
ValueSource
Galactonolactone, (D)-isomerMeSH
Galactonolactone, (L)-isomerMeSH
D-galactono-1,4-LactoneHMDB
D-galactono-1,5-LactoneHMDB
D-galactono-8-LactoneHMDB
D-GalactonolactoneHMDB
delta-galactono-1,4-LactoneHMDB
delta-galactono-1,5-LactoneHMDB
delta-galactono-8-LactoneHMDB
delta-GalactonolactoneHMDB
gamma-D-GalactonolactoneHMDB
gamma-delta-GalactonolactoneHMDB
GalactonolactoneMeSH
Chemical FormulaC6H10O6
Average Molecular Weight178.14
Monoisotopic Molecular Weight178.047738052
IUPAC Name(3R,4S,5S,6R)-3,4,5,6-tetrahydroxyoxepan-2-one
Traditional Namegalactonolactone
CAS Registry Number2426-46-2
SMILES
O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C6H10O6/c7-2-1-12-6(11)5(10)4(9)3(2)8/h2-5,7-10H,1H2/t2-,3+,4+,5-/m1/s1
InChI KeyWTXGYGWMPUGBAL-MGCNEYSASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassNot Available
Direct ParentLactones
Alternative Parents
Substituents
  • Caprolactone
  • Oxepane
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility583 g/LALOGPS
logP10(-2.3) g/LALOGPS
logP10(-2.7) g/LChemAxon
logS10(0.51) g/LALOGPS
pKa (Strongest Acidic)11.61ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.78 m³·mol⁻¹ChemAxon
Polarizability14.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.08531661259
DarkChem[M-H]-134.09431661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Galactonolactone,1TMS,#1C[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O1655.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,1TMS,#2C[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O)[C@H](O)[C@@H]1O1690.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,1TMS,#3C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)COC(=O)[C@@H]1O1705.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,1TMS,#4C[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@H](O)[C@H]1O1692.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TMS,#1C[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O1771.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TMS,#2C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O[Si](C)(C)C)COC(=O)[C@@H]1O1769.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TMS,#3C[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C1740.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TMS,#4C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)OC[C@H]1O1786.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TMS,#5C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)COC(=O)[C@@H]1O[Si](C)(C)C1758.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TMS,#6C[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@H](O)[C@H]1O[Si](C)(C)C1768.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TMS,#1C[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O1830.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TMS,#2C[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O[Si](C)(C)C)COC(=O)[C@@H]1O[Si](C)(C)C1832.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TMS,#3C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)COC(=O)[C@H](O)[C@H]1O[Si](C)(C)C1795.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TMS,#4C[Si](C)(C)O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)OC[C@H]1O1836.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,4TMS,#1C[Si](C)(C)O[C@@H]1[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)OC[C@H]1O[Si](C)(C)C1867.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O1921.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,1TBDMS,#2CC(C)(C)[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O)[C@H](O)[C@@H]1O1924.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,1TBDMS,#3CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)COC(=O)[C@@H]1O1945.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,1TBDMS,#4CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@H](O)[C@H]1O1947.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O2236.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TBDMS,#2CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)COC(=O)[C@@H]1O2223.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TBDMS,#3CC(C)(C)[Si](C)(C)O[C@@H]1COC(=O)[C@H](O)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2209.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TBDMS,#4CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)OC[C@H]1O2255.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TBDMS,#5CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O)COC(=O)[C@@H]1O[Si](C)(C)C(C)(C)C2204.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,2TBDMS,#6CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)COC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2226.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H]1C(=O)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2507.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TBDMS,#2CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)COC(=O)[C@@H]1O[Si](C)(C)C(C)(C)C2493.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TBDMS,#3CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)COC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2478.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,3TBDMS,#4CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)OC[C@H]1O2494.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Galactonolactone,4TBDMS,#1CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)OC[C@H]1O[Si](C)(C)C(C)(C)C2707.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Galactonolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rl-9400000000-9e4502053b3fe09f123e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galactonolactone GC-MS (4 TMS) - 70eV, Positivesplash10-0kou-3279300000-1418a34fa3efbbb205d12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Galactonolactone 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 - Galactonolactone 10V, Positive-QTOFsplash10-01t9-0900000000-685a5dbb4f8a7102dcc52015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 20V, Positive-QTOFsplash10-03fr-2900000000-83611a0f9b640623ac242015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 40V, Positive-QTOFsplash10-0a4i-9200000000-fbfa10412acfeb6c48112015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 10V, Negative-QTOFsplash10-004i-1900000000-61baef021fc455ee67ea2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 20V, Negative-QTOFsplash10-056r-2900000000-9c6963bd735f92051d972015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 40V, Negative-QTOFsplash10-0a4i-9100000000-4f71f72cc2972d6c238b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 10V, Positive-QTOFsplash10-004i-0900000000-4af21996c208dcba14ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 20V, Positive-QTOFsplash10-03fu-9500000000-ac5d2741d49de16a664a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 40V, Positive-QTOFsplash10-0btc-9000000000-0a9b1531d89f4242cbcb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 10V, Negative-QTOFsplash10-004i-1900000000-9622261df6835436c4f02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 20V, Negative-QTOFsplash10-0abc-9200000000-3d5e0ea9ad8151fc6cc02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Galactonolactone 40V, Negative-QTOFsplash10-0a4l-9000000000-8c8e168512fbb0f52fa32021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDFDB023025
KNApSAcK IDNot Available
Chemspider ID133098
KEGG Compound IDC03383
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6712
PubChem Compound151006
PDB IDNot Available
ChEBI ID15895
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChiocconi Alejandro; Marino Carla; Otal Eugenio; de Lederkremer Rosa M Photoinduced electron transfer and chemical alpha-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides. Carbohydrate research (2002), 337(21-23), 2119-26.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rakotomanga S, Baillet A, Pellerin F, Baylocq-Ferrier D: Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia. J Chromatogr. 1991 Oct 4;570(2):277-84. [PubMed:1797843 ]
  2. Gates SC, Sweeley CC, Krivit W, DeWitt D, Blaisdell BE: Automated metabolic profiling of organic acids in human urine. II. Analysis of urine samples from "healthy" adults, sick children, and children with neuroblastoma. Clin Chem. 1978 Oct;24(10):1680-9. [PubMed:699273 ]