General Information of MET (ID: META00293)
Name Fructose
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Apir levulosa; Baxter brand OF fructose; Bieffe brand OF fructose; Braun brand OF fructose; D-(-)-Fructose; Ern brand OF fructose; FRU; FRUCTOSE; Fleboplast levulosa; Fresenius kabi brand OF fructose; Fructon; Grifols brand OF fructose; Instituto farmacologico brand OF fructose; Levulosa; Levulosa baxter; Levulosa braun; Levulosa grifols; Levulosa ibys; Levulosa ife; Levulosa mein; Levulosa, apir; Levulosa, fleboplast; Levulosado bieffe medit; Levulosado braun; Levulosado vitulia; Levulose; Plast apyr levulosa mein; beta-D-Arabino-hexulose; beta-D-Fructofuranose; beta-D-Fructose; beta-Fruit sugar; beta-Levulose; beta-delta-Arabino-hexulose; beta-delta-Fructofuranose; beta-delta-Fructose; delta-(-)-Fructose; delta-Fructose
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Drug;Toxins/Pollutant;Microbial
Structure Type   Carbohydrates and carbohydrate conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic oxygen compounds
Organooxygen compounds
Carbohydrates and carbohydrate conjugates
PubChem CID
439709
HMDB ID
HMDB0000660
Formula
C6H12O6
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=439709"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C02336
ChEBI ID
28645
FooDB ID
FDB031286
ChemSpider ID
388775
METLIN ID
135
Physicochemical Properties Molecular Weight 180.16 Topological Polar Surface Area 110
XlogP -2.3 Complexity 162
Heavy Atom Count 12 Rotatable Bond Count 2
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 6
Function
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 therefore 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).
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR secretin (GPCR-2)
            Glucagon receptor (GCGR) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of Gcgr
                      Induced Change Fructose concentration: decrease (FC = 1.4)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Type 2 diabetes mellitus [ICD-11: 5A11]
                      Details It is reported that knockout of GCGR leads to the decrease of fructose levels compared with control group.
      Hydrolases (EC 3)
            Alpha-N-acetylglucosaminidase (NAGLU) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of Naglu
                      Induced Change Fructose concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Lysosomal storage diseases [ICD-11: 5C56]
                      Details It is reported that knockout of Naglu leads to the decrease of fructose levels compared with control group.
      Sugar transporter (ST)
            Glucose transporter type 14 (GLUT-14) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Overexpression of SLC2A14
                      Induced Change Fructose concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Inflammatory bowel disease [ICD-11: DD72]
                      Details It is reported that overexpression of SLC2A14 leads to the increase of fructose levels compared with control group.
            Glucose transporter type 2 (GLUT-2) Click to Show/Hide the Full List of Regulating Pair(s):   3 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Mutation (I322V) of SLC2A2
                      Induced Change Fructose concentration: decrease (FC = 0.60)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (I322V) of SLC2A2 leads to the decrease of fructose levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Mutation (p.277-279 HVA>QLS) of SLC2A2
                      Induced Change Fructose concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (p.277-279 HVA>QLS) of SLC2A2 leads to the decrease of fructose levels compared with control group.
               Regulating Pair (3) Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Overexpression of SLC2A2
                      Induced Change Fructose concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC2A2 leads to the increase of fructose levels compared with control group.
            Glucose transporter type 3 (GLUT-3) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Mutation (p.277-279 HVA>QLS) of SLC2A3
                      Induced Change Fructose concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (p.277-279 HVA>QLS) of SLC2A3 leads to the decrease of fructose levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [6]
                      Introduced Variation Knockdown (siRNA) of SLC2A3
                      Induced Change Fructose concentration: decrease (FC = 0.72)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Insulin-resistance syndromes [ICD-11: 5A44]
                      Details It is reported that knockdown of SLC2A3 leads to the decrease of fructose levels compared with control group.
            Glucose transporter type 5 (GLUT-5) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Overexpression of SLC2A5
                      Induced Change Fructose concentration: increase (FC = 8 - 9)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC2A5 leads to the increase of fructose levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [7]
                      Introduced Variation Mutation (I296V) of SLC2A5
                      Induced Change Fructose concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (I296V) of SLC2A5 leads to the decrease of fructose levels compared with control group.
            Glucose transporter type 7 (GLUT-7) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [7]
                      Introduced Variation Mutation (I314V) of SLC2A7
                      Induced Change Fructose concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that mutation (I314V) of SLC2A7 leads to the decrease of fructose levels compared with control group.
            Glucose transporter type 9 (GLUT-9) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Overexpression of SLC2A9
                      Induced Change Fructose concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC2A9 leads to the decrease of fructose levels compared with control group.
            HepG2 glucose transporter (SLC2A1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [6]
                      Introduced Variation Knockdown (siRNA) of SLC2A1
                      Induced Change Fructose concentration: decrease (FC = 0.65)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Insulin-resistance syndromes [ICD-11: 5A44]
                      Details It is reported that knockdown of SLC2A1 leads to the decrease of fructose levels compared with control group.
References
1 Polyomic profiling reveals significant hepatic metabolic alterations in glucagon-receptor (GCGR) knockout mice: implications on anti-glucagon therapies for diabetes. BMC Genomics. 2011 Jun 1;12:281.
2 Near-Complete Correction of Profound Metabolomic Impairments Corresponding to Functional Benefit in MPS IIIB Mice after IV rAAV9-hNAGLU Gene Delivery. Mol Ther. 2017 Mar 1;25(3):792-802.
3 The SLC2A14 gene, encoding the novel glucose/dehydroascorbate transporter GLUT14, is associated with inflammatory bowel disease. Am J Clin Nutr. 2017 Dec;106(6):1508-1513.
4 Reassessment of GLUT7 and GLUT9 as Putative Fructose and Glucose Transporters. J Membr Biol. 2017 Apr;250(2):171-182.
5 QLS motif in transmembrane helix VII of the glucose transporter family interacts with the C-1 position of D-glucose and is involved in substrate selection at the exofacial binding site. Biochemistry. 1998 Feb 3;37(5):1322-6.
6 Transendothelial glucose transport is not restricted by extracellular hyperglycaemia. Vascul Pharmacol. 2016 Dec;87:219-229.
7 Identification of a hydrophobic residue as a key determinant of fructose transport by the facilitative hexose transporter SLC2A7 (GLUT7). J Biol Chem. 2005 Dec 30;280(52):42978-83.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.