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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:48 UTC
HMDB IDHMDB0000150
Secondary Accession Numbers
  • HMDB00150
Metabolite Identification
Common NameGluconolactone
DescriptionGluconolactone, also known as glucono-delta-lactone or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids (PHAs) containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is a lactone of D-gluconic acid. Gluconolactone can be produced by enzymatic oxidation of D-glucose via the enzyme glucose oxidase. It is a fundamental metabolite found in all organisms ranging from bacteria to plants to animals. Gluconolactone has metal chelating, moisturizing and antioxidant activities. Its ability in free radicals scavenging accounts for its antioxidant properties. Gluconolactone, is also used as a food additive with the E-number E575. In foods it is used as a sequestrant, an acidifier or a curing, pickling, or leavening agent. Gluconolactone is also used as a coagulant in tofu processing. Gluconolactone is widely used as a skin exfoliant in cosmetic products, where it is noted for its mild exfoliating and hydrating properties. Pure gluconolactone is a white odorless crystalline powder. It is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods. Gluconic acid has roughly a third of the sourness of citric acid. One gram of gluconolactone yields roughly the same amount of metabolic energy as one gram of sugar.
Structure
Data?1600446526
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
Physiological effect

Adverse health effect

Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point151 - 155 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility590 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available130.589http://allccs.zhulab.cn/database/detail?ID=AllCCS00000372
[M+H]+Not Available127.642http://allccs.zhulab.cn/database/detail?ID=AllCCS00000372
Predicted Molecular Properties
PropertyValueSource
Water Solubility586 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.74731661259
DarkChem[M-H]-133.24531661259
AllCCS[M+H]+139.86932859911
AllCCS[M-H]-130.8232859911
DeepCCS[M+H]+138.2130932474
DeepCCS[M-H]-135.81730932474
DeepCCS[M-2H]-170.24430932474
DeepCCS[M+Na]+144.55730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GluconolactoneOC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O3157.3Standard polar33892256
GluconolactoneOC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O1752.4Standard non polar33892256
GluconolactoneOC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O1668.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Gluconolactone,1TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O1668.7Semi standard non polar33892256
Gluconolactone,1TMS,isomer #2C[Si](C)(C)O[C@H]1C(=O)O[C@H](CO)[C@@H](O)[C@@H]1O1680.4Semi standard non polar33892256
Gluconolactone,1TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](O)C(=O)O[C@H](CO)[C@H]1O1679.8Semi standard non polar33892256
Gluconolactone,1TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O1663.2Semi standard non polar33892256
Gluconolactone,2TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O1722.4Semi standard non polar33892256
Gluconolactone,2TMS,isomer #2C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O1718.1Semi standard non polar33892256
Gluconolactone,2TMS,isomer #3C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C1716.0Semi standard non polar33892256
Gluconolactone,2TMS,isomer #4C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)C(=O)O[C@@H]1CO1712.7Semi standard non polar33892256
Gluconolactone,2TMS,isomer #5C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)C(=O)O[C@H](CO)[C@H]1O1701.1Semi standard non polar33892256
Gluconolactone,2TMS,isomer #6C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C1694.8Semi standard non polar33892256
Gluconolactone,3TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O1769.7Semi standard non polar33892256
Gluconolactone,3TMS,isomer #2C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C1793.1Semi standard non polar33892256
Gluconolactone,3TMS,isomer #3C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1770.8Semi standard non polar33892256
Gluconolactone,3TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)C(=O)O[C@H](CO)[C@H]1O[Si](C)(C)C1760.9Semi standard non polar33892256
Gluconolactone,4TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1839.8Semi standard non polar33892256
Gluconolactone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O1922.6Semi standard non polar33892256
Gluconolactone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C(=O)O[C@H](CO)[C@@H](O)[C@@H]1O1941.3Semi standard non polar33892256
Gluconolactone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)C(=O)O[C@H](CO)[C@H]1O1929.1Semi standard non polar33892256
Gluconolactone,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O1921.9Semi standard non polar33892256
Gluconolactone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O2201.1Semi standard non polar33892256
Gluconolactone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2204.7Semi standard non polar33892256
Gluconolactone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2185.5Semi standard non polar33892256
Gluconolactone,2TBDMS,isomer #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)O[C@@H]1CO2195.3Semi standard non polar33892256
Gluconolactone,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[C@H](CO)[C@H]1O2178.5Semi standard non polar33892256
Gluconolactone,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)OC(=O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2183.8Semi standard non polar33892256
Gluconolactone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2474.2Semi standard non polar33892256
Gluconolactone,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2485.9Semi standard non polar33892256
Gluconolactone,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2471.6Semi standard non polar33892256
Gluconolactone,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C2455.4Semi standard non polar33892256
Gluconolactone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2701.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Gluconolactone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0932000000-0b9d34fd1930d30adac92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gluconolactone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-005a-0920000000-48470ef74f46934597a02014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gluconolactone GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014j-0950000000-483acf515b56ae5dc8862014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gluconolactone GC-MS (4 TMS)splash10-0fvi-1952000000-f92fb779cdb5daa45f092014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized)splash10-0fvi-1952000000-f92fb779cdb5daa45f092017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-11bi-9500000000-59fc28b889280c7c2a5c2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (4 TMS) - 70eV, Positivesplash10-0kki-7239300000-aa269ca53fc88c5847e72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gluconolactone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-001i-5900000000-443ab6dcdad04641cb492012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-0avl-9000000000-5aba2e27767b74e7e3152012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-052f-9000000000-081648ead7bc8b21d9412012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 10V, Negative-QTOFsplash10-054t-9200000000-f80b44237ec36658430a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 28V, Negative-QTOFsplash10-004i-9800000000-3c2752fe8b35c2f728502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 20V, Negative-QTOFsplash10-0ab9-9000000000-05bc27806ac72dbcec472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 40V, Negative-QTOFsplash10-052f-9000000000-1f7ea9822812efafd66e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 35V, Negative-QTOFsplash10-0002-9000000000-32e4789569e5ebdb0a572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 40V, Positive-QTOFsplash10-0006-9000000000-5c93d1197ecefd3faca02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 20V, Positive-QTOFsplash10-0avj-9000000000-56d207c80751c4bc3c092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gluconolactone 10V, Positive-QTOFsplash10-06ei-9300000000-b4b9842c0062ae80b7892021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 10V, Positive-QTOFsplash10-01t9-0900000000-7a99fa6e5ac000ab06f12017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 20V, Positive-QTOFsplash10-03fu-3900000000-7f96bedb201e601e238e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 40V, Positive-QTOFsplash10-006x-9200000000-c51e82de843b7755c5b62017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 10V, Negative-QTOFsplash10-004i-3900000000-b80e81f6d02c1d0116a22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 20V, Negative-QTOFsplash10-0adi-6900000000-590a75b51bd97402a88d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 40V, Negative-QTOFsplash10-052f-9000000000-ea7b9a23b7a07d266c682017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 10V, Positive-QTOFsplash10-01tc-0900000000-061a17370d3f9bfa1c132021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 20V, Positive-QTOFsplash10-01tl-9500000000-549c20b0fb39634d87312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 40V, Positive-QTOFsplash10-08mm-9100000000-44352cf8b9847abddc992021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 10V, Negative-QTOFsplash10-004i-0900000000-4498d74e012d572e64932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 20V, Negative-QTOFsplash10-0a6r-6900000000-2d15c7e5cc6967914c932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gluconolactone 40V, Negative-QTOFsplash10-0abc-9000000000-1f0b910b13e645939f4c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate Cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Prostate cancer
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Associated OMIM IDs
DrugBank IDDB04564
Phenol Explorer Compound IDNot Available
FooDB IDFDB001245
KNApSAcK IDNot Available
Chemspider ID6760
KEGG Compound IDC00198
BioCyc IDGLC-D-LACTONE
BiGG IDNot Available
Wikipedia LinkGluconolactone
METLIN ID353
PubChem Compound7027
PDB IDNot Available
ChEBI ID16217
Food Biomarker OntologyNot Available
VMH IDG15LAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceChu, Lijia. Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China) (1985), 66 13-14.
Material Safety Data Sheet (MSDS)Download (PDF)
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. Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. [PubMed:3128683 ]
  3. Hunt MJ, Barnetson RS: A comparative study of gluconolactone versus benzoyl peroxide in the treatment of acne. Australas J Dermatol. 1992;33(3):131-4. [PubMed:1303072 ]
  4. Steinberg KK, Needham LL: A comparison of two methods for quantifying D-glucaric acid. J Anal Toxicol. 1986 Jul-Aug;10(4):139-41. [PubMed:3747452 ]
  5. Friedrich T, Strohdeicher M, Hofhaus G, Preis D, Sahm H, Weiss H: The same domain motif for ubiquinone reduction in mitochondrial or chloroplast NADH dehydrogenase and bacterial glucose dehydrogenase. FEBS Lett. 1990 Jun 4;265(1-2):37-40. [PubMed:2142103 ]
  6. Puri RN, Zhou FX, Colman RF, Colman RW: Plasmin-induced platelet aggregation is accompanied by cleavage of aggregin and indirectly mediated by calpain. Am J Physiol. 1990 Dec;259(6 Pt 1):C862-8. [PubMed:2148055 ]
  7. van Weely S, Brandsma M, Strijland A, Tager JM, Aerts JM: Demonstration of the existence of a second, non-lysosomal glucocerebrosidase that is not deficient in Gaucher disease. Biochim Biophys Acta. 1993 Mar 24;1181(1):55-62. [PubMed:8457606 ]
  8. MacNeil ML, Steinberg KK, Yeager PR, Smith SJ: A semiautomated procedure for urinary D-glucaric acid using a centrifugal analyzer. J Anal Toxicol. 1986 Jan-Feb;10(1):15-7. [PubMed:3951202 ]

Enzymes

General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Hydrolysis of 6-phosphogluconolactone to 6-phosphogluconate.
Gene Name:
PGLS
Uniprot ID:
O95336
Molecular weight:
27546.495
General function:
Involved in glucose-6-phosphate dehydrogenase activity
Specific function:
Produces pentose sugars for nucleic acid synthesis and main producer of NADPH reducing power.
Gene Name:
G6PD
Uniprot ID:
P11413
Molecular weight:
62467.88
General function:
Involved in 6-phosphogluconolactonase activity
Specific function:
Oxidizes glucose-6-phosphate and glucose, as well as other hexose-6-phosphates.
Gene Name:
H6PD
Uniprot ID:
O95479
Molecular weight:
88891.99
Reactions
D-Glucose + NAD(P)(+) → Gluconolactone + NAD(P)Hdetails
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGM
Uniprot ID:
P11217
Molecular weight:
87316.355
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGB
Uniprot ID:
P11216
Molecular weight:
96695.18
General function:
Involved in calcium ion binding
Specific function:
Gluconolactonase with low activity towards other sugar lactones, including gulonolactone and galactonolactone. Can also hydrolyze diisopropyl phosphorofluoridate and phenylacetate (in vitro). Calcium-binding protein. Modulates Ca(2+) signaling, and Ca(2+)-dependent cellular processes and enzyme activities (By similarity).
Gene Name:
RGN
Uniprot ID:
Q15493
Molecular weight:
33252.53
Reactions
Gluconolactone + Water → Gluconic aciddetails