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Record Information
Version1.0
Creation Date2016-07-13 19:41:36 UTC
Update Date2016-07-20 20:55:23 UTC
LmdbLMDB00065
Secondary Accession NumbersNone
Metabolite Identification
Common NameGluconolactone
DescriptionGluconolactone, also known as fujiglucon or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Gluconolactone exists in all living organisms, ranging from bacteria to humans. Within humans, gluconolactone participates in a number of enzymatic reactions. In particular, gluconolactone can be biosynthesized from β-D-glucose 6-phosphate; which is mediated by the enzyme glucose-6-phosphate 1-dehydrogenase. In addition, gluconolactone can be converted into 6-phosphogluconic acid; which is mediated by the enzyme 6-phosphogluconolactonase. An aldono-1,5-lactone obtained from D-gluconic acid. In humans, gluconolactone is involved in the metabolic disorder called the glucose-6-phosphate dehydrogenase deficiency pathway. Gluconolactone is an odorless tasting compound. Outside of the human body,.
Structure
Thumb
Synonyms
ValueSource
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-oneChEBI
1,5-D-GluconolactoneChEBI
1,5-GluconolactoneChEBI
D-AldonolactoneChEBI
D-Gluconic acid delta-lactoneChEBI
D-Gluconic acid lactoneChEBI
D-GluconolactoneChEBI
D-threo-aldono-1,5-LactoneChEBI
delta-D-GluconolactoneChEBI
delta-GluconolactoneChEBI
GlucarolactoneChEBI
Gluconic acid lactoneChEBI
Gluconic delta-lactoneChEBI
Gluconic lactoneChEBI
D-Gluconate delta-lactoneGenerator
D-Gluconate δ-lactoneGenerator
D-Gluconic acid δ-lactoneGenerator
D-Gluconate lactoneGenerator
δ-D-gluconolactoneGenerator
δ-GluconolactoneGenerator
Gluconate lactoneGenerator
Gluconic δ-lactoneGenerator
1,5-delta-GluconolactoneHMDB
3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-oneHMDB
D-(+)-Gluconic acid D-lactoneHMDB
D-(+)-Gluconic acid-delta lactoneHMDB
D-delta-GluconolactoneHMDB
D-Gluconic acid 1,5-lactoneHMDB
D-Gluconic acid D-lactoneHMDB
D-Gluconic acid-1,5-lactoneHMDB
D-Gluconic acid-delta-lactoneHMDB
D-Gluconic delta-lactoneHMDB
D-Glucono-1,5-lactoneHMDB
D-glucono-D-LactoneHMDB
delta-(+)-Gluconic acid D-lactoneHMDB
delta-AldonolactoneHMDB
delta-Gluconic acid 1,5-lactoneHMDB
delta-Gluconic acid D-lactoneHMDB
delta-Gluconic acid lactoneHMDB
delta-Gluconic acid-1,5-lactoneHMDB
delta-Glucono-1,5-lactoneHMDB
FujigluconHMDB
Gluconate, lactoneHMDB
Glucono 1,5-lactoneHMDB
Glucono delta lactoneHMDB
Glucono delta-lactoneHMDB
GDL (Gluconate)MeSH, HMDB
Glucono-delta-lactoneMeSH
(3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-oneHMDB
D-(+)-Gluconic acid delta-lactoneHMDB
D-(+)-Gluconic acid δ-lactoneHMDB
D-(+)-Glucono-1,5-lactoneHMDB
D-(+)-Glucono-delta-lactoneHMDB
D-(+)-Glucono-δ-lactoneHMDB
D-(+)-Glucose delta-lactoneHMDB
D-(+)-Glucose δ-lactoneHMDB
D-Glucono-delta-lactoneHMDB
D-Glucono-δ-lactoneHMDB
Glucono-δ-lactoneHMDB
GluconolactoneHMDB
LysactoneHMDB
Chemical FormulaC6H10O6
Average Molecular Weight178.14
Monoisotopic Molecular Weight178.047738052
IUPAC Name(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Traditional Namegluconolactone
CAS Registry Number90-80-2
SMILES
OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1
InChI KeyPHOQVHQSTUBQQK-SQOUGZDYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGluconolactones
Alternative Parents
Substituents
  • Gluconolactone
  • Delta valerolactone
  • Delta_valerolactone
  • Oxane
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.2ALOGPS
logP-2.7ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.78 m³·mol⁻¹ChemAxon
Polarizability15.53 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0932000000-0b9d34fd1930d30adac9Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-005a-0920000000-48470ef74f46934597a0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014j-0950000000-483acf515b56ae5dc886Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fvi-1952000000-f92fb779cdb5daa45f09Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fvi-1952000000-f92fb779cdb5daa45f09Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-11bi-9500000000-59fc28b889280c7c2a5cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0kki-7239300000-aa269ca53fc88c5847e7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-001i-5900000000-443ab6dcdad04641cb49Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0avl-9000000000-5aba2e27767b74e7e315Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-052f-9000000000-081648ead7bc8b21d941Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-054t-9200000000-f80b44237ec36658430aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 28V, Negativesplash10-004i-9800000000-3c2752fe8b35c2f72850Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9000000000-05bc27806ac72dbcec47Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-1f7ea9822812efafd66eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-9000000000-32e4789569e5ebdb0a57Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5c93d1197ecefd3faca0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0avj-9000000000-56d207c80751c4bc3c09Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-06ei-9300000000-b4b9842c0062ae80b789Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0900000000-7a99fa6e5ac000ab06f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-3900000000-7f96bedb201e601e238eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-c51e82de843b7755c5b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-b80e81f6d02c1d0116a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-6900000000-590a75b51bd97402a88dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-ea7b9a23b7a07d266c68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-0900000000-061a17370d3f9bfa1c13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tl-9500000000-549c20b0fb39634d8731Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08mm-9100000000-44352cf8b9847abddc99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-4498d74e012d572e6493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-6900000000-2d15c7e5cc6967914c93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-1f0b910b13e645939f4cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB04564
HMDB IDHMDB0000150
FooDB IDFDB001245
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDGLC-D-LACTONE
METLIN ID353
PDB IDNot Available
Wikipedia LinkGluconolactone
Chemspider ID6760
ChEBI ID16217
PubChem Compound ID7027
Kegg Compound IDC00198
YMDB IDNot Available
ECMDB IDECMDB00150
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available