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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:59 UTC
HMDB IDHMDB00150
Secondary Accession NumbersNone
Metabolite Identification
Common NameGluconolactone
DescriptionGluconolactone is a lactone or oxidized derivative of glucose. Gluconolactone is a polyhydroxy acid (PHA) that is capable of chelating metals and may also function by scavenging free radicals, thereby protecting skin from some of the damaging effects of UV radiation. Also used as a pheromone by the oriental cockroach.
Structure
Thumb
Synonyms
  1. 1,5-D-Gluconolactone
  2. 1,5-delta-Gluconolactone
  3. 1,5-Gluconolactone
  4. 3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
  5. beta-Glucono-1,5-Lactone
  6. D(+)-Gluconic acid gamma-lactone
  7. D-(+)-Gluconic acid D-lactone
  8. D-(+)-Gluconic acid-delta lactone
  9. D-Aldonolactone
  10. D-delta-Gluconolactone
  11. D-Gluconic acid 1,5-lactone
  12. D-Gluconic acid D-lactone
  13. D-Gluconic acid delta-lactone
  14. D-Gluconic acid lactone
  15. D-Gluconic acid-1,5-lactone
  16. D-Gluconic acid-delta-lactone
  17. D-Gluconic delta-lactone
  18. D-Glucono-1,5-lactone
  19. D-Glucono-D-lactone
  20. D-Gluconolactone
  21. delta-(+)-Gluconic acid D-lactone
  22. delta-(+)-Gluconic acid-delta lactone
  23. delta-Aldonolactone
  24. delta-D-Gluconolactone
  25. delta-delta-Gluconolactone
  26. delta-Gluconic acid 1,5-lactone
  27. delta-Gluconic acid D-lactone
  28. delta-Gluconic acid delta-lactone
  29. delta-Gluconic acid lactone
  30. delta-Gluconic acid-1,5-lactone
  31. delta-Gluconic acid-delta-lactone
  32. delta-Gluconic delta-lactone
  33. delta-Glucono-1,5-lactone
  34. delta-Glucono-delta-lactone
  35. delta-Gluconolactone
  36. Fujiglucon
  37. gamma-Gluconolactone
  38. Glucarolactone
  39. Gluconate, lactone
  40. Gluconic acid lactone
  41. Gluconic delta-lactone
  42. Gluconic lactone
  43. Glucono 1,5-lactone
  44. Glucono delta lactone
  45. Glucono delta-lactone
  46. Glucono gamma-lactone
  47. Gluconolactone
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 IUPAC 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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • gluconolactone(ChEBI)
Substituents
  • 1,2 Diol
  • Carboxylic Acid Ester
  • Delta Valerolactone
  • Lactone
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point151 - 155 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility590.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted 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 area107.22ChemAxon
rotatable bond count1ChemAxon
refractivity34.78ChemAxon
polarizability15.42ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pentose Phosphate PathwaySMP00031map00030
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Prostate 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. Pubmed: 19212411
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001245
KNApSAcK IDNot Available
Chemspider ID6760
KEGG Compound IDC00198
BioCyc IDGLC-D-LACTONE
BiGG IDNot Available
Wikipedia LinkGluconolactone
NuGOwiki LinkHMDB00150
Metagene LinkHMDB00150
METLIN ID353
PubChem Compound7027
PDB IDLGC
ChEBI ID16217
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
Beta-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