Human Metabolome Database Version 3.5

Showing metabocard for D-Fructose (HMDB00660)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:02 -0700
HMDB ID HMDB00660
Secondary Accession Numbers None
Metabolite Identification
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).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. beta-D-Arabino-hexulose
  2. beta-D-Fructofuranose
  3. beta-D-Fructose
  4. beta-delta-Arabino-hexulose
  5. beta-delta-Fructofuranose
  6. beta-delta-Fructose
  7. beta-Fruit sugar
  8. beta-Levulose
  9. D-(-)-Fructose
  10. D-Fructose
  11. delta-(-)-Fructose
  12. delta-Fructose
  13. FRU
  14. Fructon
  15. Fructose
  16. Levulose
Chemical Formula C6H12O6
Average Molecular Weight 180.1559
Monoisotopic Molecular Weight 180.063388116
IUPAC Name (2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Traditional IUPAC Name fructose
CAS Registry Number 53188-23-1
SMILES OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O
InChI Identifier InChI=1S/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
InChI Key RFSUNEUAIZKAJO-ARQDHWQXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Pentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • D-fructofuranose(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxolane
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Pentoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 119 - 122 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 778 mg/mL at 20 °C YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1110 g/L ALOGPS
LogP -2.45 ALOGPS
LogP -2.8 ChemAxon
LogS 0.79 ALOGPS
pKa (strongest acidic) 10.28 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 110.38 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 36.36 ChemAxon
Polarizability 16.52 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Liver
  • Prostate
  • Sperm
Pathways
Name SMPDB Link KEGG Link
Starch and Sucrose Metabolism SMP00058 map00500 Link_out
Galactose Metabolism SMP00043 map00052 Link_out
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Amino Sugar Metabolism SMP00045 map00520 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
31.0 +/- 3.0 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
48.0 +/- 16.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
240.0 (220.0 -260.0) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
160 +/- 91 uM Not Specified Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
70.38 +/- 107.54 umol/mmol creatinine Infant (0-1 year old) Not Specified Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 12.00 +/- 3.8 uM Adult (>18 years old) Both Diabetes
Urine Detected and Quantified 8.4 +/- 7.0 umol/mmol creatinine Adult (>18 years old) Both Diabetes
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  • Kawasaki T, Akanuma H, Yamanouchi T: Increased fructose concentrations in blood and urine in patients with diabetes. Diabetes Care. 2002 Feb;25(2):353-7. Pubmed: 11815509 Link_out
      Associated OMIM IDs
      • 125853 Link_out (Diabetes mellitus type 2)
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012528
      KNApSAcK ID C00033848 Link_out
      Chemspider ID 388775 Link_out
      KEGG Compound ID C02336 Link_out
      BioCyc ID CPD-535 Link_out
      BiGG ID 33835 Link_out
      Wikipedia Link FRU Link_out
      NuGOwiki Link HMDB00660 Link_out
      Metagene Link HMDB00660 Link_out
      METLIN ID 135 Link_out
      PubChem Compound 439709 Link_out
      PDB ID FRU Link_out
      ChEBI ID 28645 Link_out
      References
      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.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Vicari E, La Vignera S, Castiglione R, Calogero AE: Sperm parameter abnormalities, low seminal fructose and reactive oxygen species overproduction do not discriminate patients with unilateral or bilateral post-infectious inflammatory prostato-vesiculo-epididymitis. J Endocrinol Invest. 2006 Jan;29(1):18-25. Pubmed: 16553029 Link_out
      2. Bar A: Characteristics and significance of D-tagatose-induced liver enlargement in rats: An interpretative review. Regul Toxicol Pharmacol. 1999 Apr;29(2 Pt 2):S83-93. Pubmed: 10341166 Link_out
      3. Andrade-Rocha FT: Semen analysis in an infertile man with seminal vesicles cysts associated with ipsilateral renal agenesis. Int Urol Nephrol. 2006;38(1):101-3. Pubmed: 16502061 Link_out
      4. Andrade-Rocha FT: Seminal fructose levels in male infertility: relationship with sperm characteristics. Int Urol Nephrol. 1999;31(1):107-11. Pubmed: 10408311 Link_out
      5. Gonzales GF, Villena A: True corrected seminal fructose level: a better marker of the function of seminal vesicles in infertile men. Int J Androl. 2001 Oct;24(5):255-60. Pubmed: 11554981 Link_out
      6. Buemann B, Gesmar H, Astrup A, Quistorff B: Effects of oral D-tagatose, a stereoisomer of D-fructose, on liver metabolism in man as examined by 31P-magnetic resonance spectroscopy. Metabolism. 2000 Oct;49(10):1335-9. Pubmed: 11079825 Link_out
      7. Koca Y, Ozdal OL, Celik M, Unal S, Balaban N: Antioxidant activity of seminal plasma in fertile and infertile men. Arch Androl. 2003 Sep-Oct;49(5):355-9. Pubmed: 12893512 Link_out
      8. Williams AC, Ford WC: The role of glucose in supporting motility and capacitation in human spermatozoa. J Androl. 2001 Jul-Aug;22(4):680-95. Pubmed: 11451366 Link_out
      9. 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

      Enzymes
      Name: Hexokinase-3
      Reactions:
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Gene Name: HK3
      Uniprot ID: P52790 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Hexokinase-2
      Reactions:
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Gene Name: HK2
      Uniprot ID: P52789 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Hexokinase-1
      Reactions:
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Gene Name: HK1
      Uniprot ID: P19367 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Sucrase-isomaltase, intestinal
      Reactions:
      Sucrose + Water unknown D-Fructose + D-Glucose details
      Sucrose + Water unknown D-Fructose + Alpha-D-Glucose details
      Neohancoside D + Water unknown D-Fructose + D-Glucose details
      Neohancoside D + Water unknown D-Fructose + Alpha-D-Glucose details
      Gene Name: SI
      Uniprot ID: P14410 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Sorbitol dehydrogenase
      Reactions:
      Sorbitol + NAD unknown D-Fructose + NADH + Hydrogen Ion details
      Gene Name: SORD
      Uniprot ID: Q00796 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ketohexokinase
      Reactions:
      Adenosine triphosphate + D-Fructose unknown ADP + D-fructose 1-phosphate details
      Gene Name: KHK
      Uniprot ID: P50053 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lysosomal alpha-glucosidase
      Reactions:
      Sucrose + Water unknown D-Fructose + D-Glucose details
      Sucrose + Water unknown D-Fructose + Alpha-D-Glucose details
      Gene Name: GAA
      Uniprot ID: P10253 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Maltase-glucoamylase, intestinal
      Reactions:
      Sucrose + Water unknown D-Fructose + D-Glucose details
      Sucrose + Water unknown D-Fructose + Alpha-D-Glucose details
      Neohancoside D + Water unknown D-Fructose + D-Glucose details
      Neohancoside D + Water unknown D-Fructose + Alpha-D-Glucose details
      Gene Name: MGAM
      Uniprot ID: O43451 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Neutral alpha-glucosidase C
      Reactions:
      Sucrose + Water unknown D-Fructose + D-Glucose details
      Sucrose + Water unknown D-Fructose + Alpha-D-Glucose details
      Gene Name: GANC
      Uniprot ID: Q8TET4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 14 kDa phosphohistidine phosphatase
      Reactions:
      Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric acid details
      Gene Name: PHPT1
      Uniprot ID: Q9NRX4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Putative hexokinase HKDC1
      Reactions:
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphate details
      Gene Name: HKDC1
      Uniprot ID: Q2TB90 Link_out
      Protein Sequence: FASTA
      Name: Myotubularin-related protein 1
      Reactions:
      Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric acid details
      Gene Name: MTMR1
      Uniprot ID: Q13613 Link_out
      Name: Myotubularin-related protein 2
      Reactions:
      Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric acid details
      Gene Name: MTMR2
      Uniprot ID: Q13614 Link_out
      Name: Myotubularin-related protein 6
      Reactions:
      Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric acid details
      Gene Name: MTMR6
      Uniprot ID: Q9Y217 Link_out
      Name: Myotubularin-related protein 7
      Reactions:
      Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric acid details
      Gene Name: MTMR7
      Uniprot ID: Q9Y216 Link_out