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Human Metabolome Database Version 3.5

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Showing metabocard for Gluconolactone (HMDB00150)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:59 -0700
HMDB ID HMDB00150
Secondary Accession Numbers None
Metabolite Identification
Common Name Gluconolactone
Description Gluconolactone 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H10O6
Average Molecular Weight 178.14
Monoisotopic Molecular Weight 178.047738052
IUPAC Name (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Traditional IUPAC Name gluconolactone
CAS Registry Number 90-80-2
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 Key PHOQVHQSTUBQQK-SQOUGZDYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
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 Parent Hexoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 151 - 155 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 590.0 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 586 g/L ALOGPS
LogP -2.16 ALOGPS
LogP -2.7 ChemAxon
LogS 0.52 ALOGPS
pKa (strongest acidic) 11.62 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 107.22 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 34.78 ChemAxon
Polarizability 15.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.5 (0.0-1.0) uM Adult (>18 years old) Both Prostate Cancer Estimated concentration
Associated Disorders and Diseases
Disease References
Prostate cancer
  • 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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB001245
    KNApSAcK ID Not Available
    Chemspider ID 6760 Link_out
    KEGG Compound ID C00198 Link_out
    BioCyc ID GLC-D-LACTONE Link_out
    BiGG ID Not Available
    Wikipedia Link Gluconolactone Link_out
    NuGOwiki Link HMDB00150 Link_out
    Metagene Link HMDB00150 Link_out
    METLIN ID 353 Link_out
    PubChem Compound 7027 Link_out
    PDB ID LGC Link_out
    ChEBI ID 16217 Link_out
    References
    Synthesis Reference Chu, 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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    Enzymes
    Name: 6-phosphogluconolactonase
    Reactions:
    • 6-phospho-D-glucono-1,5-lactone + H2O = 6-phospho-D-gluconate [RN:R02035]
    Gene Name: PGLS
    Uniprot ID: O95336 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glucose-6-phosphate 1-dehydrogenase
    Reactions:
    • D-glucose 6-phosphate + NADP+ = D-glucono-1,5-lactone 6-phosphate + NADPH + H+ [RN:R00835]
    Gene Name: G6PD
    Uniprot ID: P11413 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: GDH/6PGL endoplasmic bifunctional protein
    Reactions:
    • 6-phospho-D-glucono-1,5-lactone + H2O = 6-phospho-D-gluconate [RN:R02035]
    Gene Name: H6PD
    Uniprot ID: O95479 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycogen phosphorylase, liver form
    Reactions:
    • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
    Gene Name: PYGL
    Uniprot ID: P06737 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycogen phosphorylase, muscle form
    Reactions:
    • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
    Gene Name: PYGM
    Uniprot ID: P11217 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycogen phosphorylase, brain form
    Reactions:
    • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
    Gene Name: PYGB
    Uniprot ID: P11216 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA