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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-13 11:44:34 UTC
Update Date2023-02-21 17:29:00 UTC
HMDB IDHMDB0041862
Secondary Accession Numbers
  • HMDB41862
Metabolite Identification
Common NameD-Glucaro-1,4-lactone
DescriptionD-Glucaro-1,4-lactone, also known as D-saccharolactone or 1,4-D-glucarolactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. D-Glucaro-1,4-lactone has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make D-glucaro-1,4-lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on D-Glucaro-1,4-lactone.
Structure
Data?1677000540
Synonyms
ValueSource
1,4-D-GlucarolactoneChEBI
1,4-GlucarolactoneChEBI
D-SaccharolactoneChEBI
SaccharolactoneChEBI
Saccharolactone, monocalcium salt, (D)-isomerHMDB
Saccharolactone, (D)-isomerHMDB
Saccharolactone, monosodium salt, (D)-isomerHMDB
Glucarate-1,4-lactoneHMDB
Chemical FormulaC6H8O7
Average Molecular Weight192.1235
Monoisotopic Molecular Weight192.02700261
IUPAC Name(2S)-2-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid
Traditional Name(S)-[(2S,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl](hydroxy)acetic acid
CAS Registry Number5027-63-4
SMILES
[H][C@@](O)(C(O)=O)[C@@]1([H])OC(=O)[C@]([H])(O)[C@@]1([H])O
InChI Identifier
InChI=1S/C6H8O7/c7-1-2(8)6(12)13-4(1)3(9)5(10)11/h1-4,7-9H,(H,10,11)/t1-,2-,3+,4+/m1/s1
InChI KeyXECPAIJNBXCOBO-MMPJQOAZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Hydroxy acid
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility159 g/LALOGPS
logP-1.9ALOGPS
logP-2.4ChemAxon
logS-0.08ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity34.65 m³·mol⁻¹ChemAxon
Polarizability15.62 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]+144.20931661259
DarkChem[M-H]-138.72931661259
DeepCCS[M+H]+135.51630932474
DeepCCS[M-H]-133.18730932474
DeepCCS[M-2H]-167.93530932474
DeepCCS[M+Na]+142.50630932474
AllCCS[M+H]+142.332859911
AllCCS[M+H-H2O]+138.232859911
AllCCS[M+NH4]+146.132859911
AllCCS[M+Na]+147.232859911
AllCCS[M-H]-131.932859911
AllCCS[M+Na-2H]-132.532859911
AllCCS[M+HCOO]-133.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-Glucaro-1,4-lactone[H][C@@](O)(C(O)=O)[C@@]1([H])OC(=O)[C@]([H])(O)[C@@]1([H])O3154.9Standard polar33892256
D-Glucaro-1,4-lactone[H][C@@](O)(C(O)=O)[C@@]1([H])OC(=O)[C@]([H])(O)[C@@]1([H])O1711.4Standard non polar33892256
D-Glucaro-1,4-lactone[H][C@@](O)(C(O)=O)[C@@]1([H])OC(=O)[C@]([H])(O)[C@@]1([H])O1677.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Glucaro-1,4-lactone,1TMS,isomer #1C[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O)[C@H]1O1790.7Semi standard non polar33892256
D-Glucaro-1,4-lactone,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O1700.0Semi standard non polar33892256
D-Glucaro-1,4-lactone,1TMS,isomer #3C[Si](C)(C)O[C@H]1C(=O)O[C@H]([C@H](O)C(=O)O)[C@@H]1O1822.4Semi standard non polar33892256
D-Glucaro-1,4-lactone,1TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](O)C(=O)O[C@@H]1[C@H](O)C(=O)O1791.5Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@H](O)[C@H]1O1784.7Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TMS,isomer #2C[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@H]1O1902.1Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TMS,isomer #3C[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C1882.1Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@H]1O1837.6Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TMS,isomer #5C[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C1827.4Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TMS,isomer #6C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)C(=O)O[C@@H]1[C@H](O)C(=O)O1863.2Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@H]1O1921.4Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C1899.2Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TMS,isomer #3C[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1942.5Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TMS,isomer #4C[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1924.6Semi standard non polar33892256
D-Glucaro-1,4-lactone,4TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C)[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1963.4Semi standard non polar33892256
D-Glucaro-1,4-lactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O)[C@H]1O2040.0Semi standard non polar33892256
D-Glucaro-1,4-lactone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O1958.1Semi standard non polar33892256
D-Glucaro-1,4-lactone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1C(=O)O[C@H]([C@H](O)C(=O)O)[C@@H]1O2085.8Semi standard non polar33892256
D-Glucaro-1,4-lactone,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)C(=O)O[C@@H]1[C@H](O)C(=O)O2055.8Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)[C@H](O)[C@H]1O2266.5Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2354.4Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2336.0Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2321.3Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2306.0Semi standard non polar33892256
D-Glucaro-1,4-lactone,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[C@@H]1[C@H](O)C(=O)O2318.5Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2585.3Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2569.5Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](C(=O)O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2610.7Semi standard non polar33892256
D-Glucaro-1,4-lactone,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2603.6Semi standard non polar33892256
D-Glucaro-1,4-lactone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2820.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - D-Glucaro-1,4-lactone GC-MS (4 TMS)splash10-014i-1971000000-6bc480f6132ff3b4f3a82014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glucaro-1,4-lactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i9-9300000000-3036b01985ecba9285d82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glucaro-1,4-lactone GC-MS (4 TMS) - 70eV, Positivesplash10-01di-6258900000-672b193020e251e416682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glucaro-1,4-lactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Glucaro-1,4-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-Glucaro-1,4-lactone 10V, Positive-QTOFsplash10-004l-1900000000-2ec6e385ad66bb32dbf62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 20V, Positive-QTOFsplash10-05r1-2900000000-8b979b3c9f43a65b913f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 40V, Positive-QTOFsplash10-00du-9000000000-6d6b84a7185d89c6f9122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 10V, Negative-QTOFsplash10-00tg-4900000000-21eb31d409626b01009c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 20V, Negative-QTOFsplash10-016s-2900000000-f8f32d204349bf2013662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 40V, Negative-QTOFsplash10-0603-9300000000-96973bb25faba1a35f092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 10V, Positive-QTOFsplash10-004i-0900000000-cc5bb18d1664b93a313a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 20V, Positive-QTOFsplash10-00os-6900000000-1ba0094376fd3554d23c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 40V, Positive-QTOFsplash10-01ox-9000000000-ca8224ed70a4c6b3efbe2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 10V, Negative-QTOFsplash10-00bc-6900000000-b6467151416eacaa1e102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 20V, Negative-QTOFsplash10-056r-9100000000-2c5aa67ce4b96aaedd102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Glucaro-1,4-lactone 40V, Negative-QTOFsplash10-0a6u-9000000000-fe8344a8a3a320b12c812021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB098184
KNApSAcK IDNot Available
Chemspider ID109061
KEGG Compound IDNot Available
BioCyc IDCPD-17141
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound122306
PDB IDNot Available
ChEBI ID85805
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available