Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:02 UTC
HMDB IDHMDB00660
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Fructose
DescriptionFructose, 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
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 FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Traditional IUPAC Namefructose
CAS Registry Number53188-23-1
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 KeyRFSUNEUAIZKAJO-ARQDHWQXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassPentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • D-fructofuranose(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxolane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentPentoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 - 122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility778 mg/mL at 20 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility1110 g/LALOGPS
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.79ALOGPS
pKa (strongest acidic)10.28ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count5ChemAxon
polar surface area110.38ChemAxon
rotatable bond count2ChemAxon
refractivity36.36ChemAxon
polarizability16.52ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Liver
  • Prostate
  • Sperm
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
Fructose and Mannose DegradationSMP00064map00051
Galactose MetabolismSMP00043map00052
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified31.0 +/- 3.0 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified48.0 +/- 16.0 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified240.0 (220.0 -260.0) uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified160 +/- 91 uMNot SpecifiedBothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified70.38 +/- 107.54 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified12.00 +/- 3.8 uMAdult (>18 years old)BothDiabetes
UrineDetected and Quantified8.4 +/- 7.0 umol/mmol creatinineAdult (>18 years old)BothDiabetes
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
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012528
KNApSAcK IDC00033848
Chemspider ID388775
KEGG Compound IDC02336
BioCyc IDCPD-535
BiGG ID33835
Wikipedia LinkFRU
NuGOwiki LinkHMDB00660
Metagene LinkHMDB00660
METLIN ID135
PubChem Compound439709
PDB IDFRU
ChEBI ID28645
References
Synthesis ReferenceLiu, 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)Not Available
General References
  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
  2. 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
  3. 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
  4. 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
  5. Andrade-Rocha FT: Seminal fructose levels in male infertility: relationship with sperm characteristics. Int Urol Nephrol. 1999;31(1):107-11. Pubmed: 10408311
  6. 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
  7. 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
  8. 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
  9. 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

Enzymes

Gene Name:
HK3
Uniprot ID:
P52790
Reactions
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Gene Name:
HK2
Uniprot ID:
P52789
Reactions
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Gene Name:
HK1
Uniprot ID:
P19367
Reactions
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Gene Name:
SI
Uniprot ID:
P14410
Reactions
Sucrose + Water unknown D-Fructose + D-Glucosedetails
Sucrose + Water unknown D-Fructose + Alpha-D-Glucosedetails
Neohancoside D + Water unknown D-Fructose + D-Glucosedetails
Neohancoside D + Water unknown D-Fructose + Alpha-D-Glucosedetails
Gene Name:
SORD
Uniprot ID:
Q00796
Reactions
Sorbitol + NAD unknown D-Fructose + NADH + Hydrogen Iondetails
Gene Name:
KHK
Uniprot ID:
P50053
Reactions
Adenosine triphosphate + D-Fructose unknown ADP + D-fructose 1-phosphatedetails
Gene Name:
GAA
Uniprot ID:
P10253
Reactions
Sucrose + Water unknown D-Fructose + D-Glucosedetails
Sucrose + Water unknown D-Fructose + Alpha-D-Glucosedetails
Gene Name:
MGAM
Uniprot ID:
O43451
Reactions
Sucrose + Water unknown D-Fructose + D-Glucosedetails
Sucrose + Water unknown D-Fructose + Alpha-D-Glucosedetails
Neohancoside D + Water unknown D-Fructose + D-Glucosedetails
Neohancoside D + Water unknown D-Fructose + Alpha-D-Glucosedetails
Gene Name:
GANC
Uniprot ID:
Q8TET4
Reactions
Sucrose + Water unknown D-Fructose + D-Glucosedetails
Sucrose + Water unknown D-Fructose + Alpha-D-Glucosedetails
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Reactions
Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric aciddetails
Gene Name:
HKDC1
Uniprot ID:
Q2TB90
Reactions
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Adenosine triphosphate + D-Fructose unknown ADP + Beta-D-Fructose 6-phosphatedetails
Gene Name:
MTMR1
Uniprot ID:
Q13613
Reactions
Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric aciddetails
Gene Name:
MTMR2
Uniprot ID:
Q13614
Reactions
Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric aciddetails
Gene Name:
MTMR6
Uniprot ID:
Q9Y217
Reactions
Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric aciddetails
Gene Name:
MTMR7
Uniprot ID:
Q9Y216
Reactions
Beta-D-Fructose 2-phosphate + Water unknown D-Fructose + Phosphoric aciddetails