General Information of MET (ID: META00188)
Name Fucose
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(-)-Fucose; (-)-L-Fucose; 6-Deoxy-L-galactopyranose; 6-Deoxy-L-galactose; 6-Desoxygalactose; 6-Methyloxane-2,3,4,5-tetrol; 6-Methyltetrahydropyran-2,3,4,5-tetraol; Deoxygalactose; Fucose; Isodulcit; L-(-)-Fucose; L-Fucopyranose; L-Galactomethylose; Rhodeose; alpha Fucose; alpha-Fucose
Source Aliphatic heteromonocyclic compounds
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
17106
HMDB ID
HMDB0000174
Formula
C6H12O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C01019
ChEBI ID
2181
FooDB ID
FDB020543
ChemSpider ID
16190
METLIN ID
268
Physicochemical Properties Molecular Weight 164.16 Topological Polar Surface Area 90.2
XlogP -2.1 Complexity 139
Heavy Atom Count 11 Rotatable Bond Count N.A.
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Function
Fucose (CAS: 2438-80-4) is a hexose deoxy sugar with the chemical formula C6H12O5. L-Fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells. It is the fundamental subunit of the fucoidan polysaccharide. As a free sugar, L-fucose is normally found at very low levels in mammals. It is unique in that it is the only levorotatory sugar synthesized and utilized by mammals. Fucose polymers are synthesized by fucosyltransferases. All fucosyltransferases utilize a nucleotide-activated form of fucose, GDP-fucose, as a fucose donor in the construction of fucosylated oligosaccharides. The ABO blood group antigens are among the most well known fucosylated glycans. The alpha-1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. Fucose is metabolized by an enzyme called alpha-fucosidase. Fucose is secreted in urine when the liver is damaged. Free L-fucose in serum and urine can be used as a marker for cancer, cirrhosis, alcoholic liver disease and gastric ulcers. Elevated levels of serum fucose have been reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes, and cardiovascular disease. It has been shown that feeding rats a diet high in L-fucose induces neuropathy similar to that seen in diabetics.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      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 [1]
                      Introduced Variation Knockout of Naglu
                      Induced Change Fucose 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 fucose levels compared with control group.
      Interleukin (IL)
            Interleukin-10 (IL10) 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 IL10
                      Induced Change Fucose concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Crohn disease [ICD-11: DD70]
                      Details It is reported that knockout of IL10 leads to the increase of fucose levels compared with control group.
References
1 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.
2 Nontargeted urinary metabolite profiling of a mouse model of Crohn&#39;s disease. J Proteome Res. 2009 Apr;8(4):2045-57.

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