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Bovine Rumen Metabolome Database



Showing metabocard for D-Fructose (RMDB00660)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-21 16:49:33
Accession Number RMDB00660
Common Name D-Fructose
Description Fructose, or levulose, is a levorotatory monosaccharide and an isomer of glucose (C6H12O6). The chemical composition of fructose is (C6H12O6). Pure fructose has a sweet taste similar to cane sugar, but with a "fruity" aroma. Although fructose is a hexose (6 carbon sugar), it generally exists as a 5-member hemiketal ring (a furanose). This structure is responsible for the long metabolic pathway and high reactivity compared to glucose. Fructose is found in many foods and is one of the three most important blood sugars along with glucose and galactose. Honey; tree fruits; berries; melons; and some root vegetables, such as beets, sweet potatoes, parsnips and onions, contain fructose, usually in combination with sucrose and glucose. Fructose is also derived from the digestion of sucrose, a disaccharide consisting of glucose and fructose that is broken down by enzymes during digestion. Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose. It is used as a preservative and an intravenous infusion in parenteral feeding. Fructose is a reducing sugar, as are all monosaccharides. The spontaneous addition of single sugar molecules to proteins, known as glycation, is a significant cause of damage in diabetics. Fructose appears to be as dangerous as glucose in this regard and so does not seem to be the answer for diabetes (McPherson et al, 1988). This may be an important contribution to senescence and many age-related chronic diseases (Levi & Werman 1998).
Synonyms
  1. Beta-d-arabino-hexulose
  2. Beta-d-fructofuranose
  3. Beta-d-fructose
  4. Beta-fruit sugar
  5. Beta-levulose
  6. D-Fructose
  7. FRU
  8. Fructon
  9. Fructose
  10. Levulose
  11. D-(-)-Fructose
  12. Beta-delta-arabino-hexulose
  13. Beta-delta-fructofuranose
  14. Beta-delta-fructose
  15. delta-Fructose
  16. delta-(-)-Fructose
Chemical IUPAC Name (2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Chemical Formula C6H12O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Monosaccharides
Family
  • Mammalian_Metabolite
Species
  • hemiacetal; primary alcohol; secondary alcohol; 1,2-diol; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 180.156
Monoisotopic Molecular Weight 180.063385
Isomeric SMILES OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
Canonical SMILES OCC1OC(O)(CO)C(O)C1O
KEGG Compound ID C02336; C00095 Link Image
BioCyc ID CPD-535 Link Image
BiGG ID 33835 Link Image
Wikipedia Link FRU Link Image
METLIN ID 135 Link Image
PubChem Compound 439709 Link Image
PubChem Substance 17436399 Link Image
ChEBI ID 15946 Link Image
CAS Registry Number 53188-23-1
InChI Identifier InChI=1/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1
Synthesis Reference Liu, Hong; Han, Dong; Meng, Xiang-bao; Li, Zhong-jun. Improved synthesis of fructose-derived 1,3,4-oxadiazole as novel antitumor agents. Journal of Chinese Pharmaceutical Sciences (2005), 14(4), 209-212.
Melting Point (Experimental) 119-122oC
Experimental Water Solubility 778 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 778.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 1.11e+03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.4 [Predicted by PubChem via XLOGP]; -2.45 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1AF6 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
  • Extracellular
Biofluid Location
  • Cow_Milk
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 763.813 +/- 751.731 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image