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Bovine Metabolome Database



Showing metabocard for Gluconolactone (BMDB00150)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:43
Accession Number BMDB00150
Common Name Gluconolactone
Description 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.
Synonyms
  1. 1,5-Gluconolactone
  2. 3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
  3. Beta-Glucono-1,5-Lactone
  4. D(+)-Gluconic acid gamma-lactone
  5. D-(+)-Gluconic acid d-lactone
  6. D-(+)-Gluconic acid-delta lactone
  7. D-Gluconic acid 1,5-lactone
  8. D-Gluconic acid d-lactone
  9. D-Gluconic acid delta-lactone
  10. D-Gluconic acid lactone
  11. D-Gluconic acid-1,5-lactone
  12. D-Glucono-1,5-lactone
  13. D-Glucono-d-lactone
  14. D-Gluconolactone
  15. Fujiglucon
  16. Glucarolactone
  17. Gluconic acid lactone
  18. Gluconic lactone
  19. Glucono 1,5-lactone
  20. Glucono delta lactone
  21. Glucono gamma-lactone
  22. Gluconolactone
  23. d-Aldonolactone
  24. delta-Gluconolactone
  25. gamma-Gluconolactone
  26. delta-(+)-Gluconic acid d-lactone
  27. delta-(+)-Gluconic acid-delta lactone
  28. delta-Gluconic acid 1,5-lactone
  29. delta-Gluconic acid d-lactone
  30. delta-Gluconic acid delta-lactone
  31. delta-Gluconic acid lactone
  32. delta-Gluconic acid-1,5-lactone
  33. delta-Glucono-1,5-lactone
  34. delta-Glucono-delta-lactone
  35. delta-Aldonolactone
Chemical IUPAC Name 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Chemical Formula C6H10O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Monosaccharides
Family
  • Mammalian_Metabolite
Species
  • primary alcohol; secondary alcohol; 1,2-diol; carboxylic acid ester; lactone; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 178.140
Monoisotopic Molecular Weight 178.047745
Isomeric SMILES OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
Canonical SMILES OCC1OC(=O)C(O)C(O)C1O
KEGG Compound ID C00198 Link Image
BioCyc ID GLC-D-LACTONE Link Image
BiGG ID Not Available
Wikipedia Link Gluconolactone Link Image
METLIN ID 353 Link Image
PubChem Compound 7027 Link Image
PubChem Substance 7888635 Link Image
ChEBI ID 16217 Link Image
CAS Registry Number 90-80-2
InChI Identifier InChI=1/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
Synthesis Reference Chu, Lijia. Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China) (1985), 66 13-14.
Melting Point (Experimental) 151-155 oC
Experimental Water Solubility 590.0 mg/mL [MERCK INDEX (1996)] Source: PhysProp
Predicted Water Solubility 586.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.16 [Predicted by ALOGPS]; -1.8 [Predicted by PubChem via XLOGP]; -1.98 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
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2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Download Spectrum
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Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Show Image
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BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Pentose Pathway
HMDB Pathways
Name Pentose Pathway
Image Show Link Image
KEGG Pathways
Name Pentose Pathway
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SimCell Pathways
Name Pentose Pathway
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Graph Show Link Image
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General References
  1. Wikipedia Link Image