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Showing NP-Card for L-Fucose (NP0001115)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-07-15 17:06:58 UTC
NP-MRD IDNP0001115
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Fucose
DescriptionFucose 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 sub-unit 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 (PMID: 2311216 ) (PMID: 8488966 ). 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
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001115 (L-Fucose)


  Mrv1652307301920042D          

 16 16  0  0  1  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
 10  6  1  0  0  0  0
  2 11  1  0  0  0  0
 11  6  1  0  0  0  0
  2 12  1  1  0  0  0
  3 13  1  1  0  0  0
  4 14  1  1  0  0  0
  5 15  1  6  0  0  0
 16  6  1  0  0  0  0
M  END
Download

3D MOL for NP0001115 (L-Fucose)

NP0001115
     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    2.5740    0.5912    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.6105   -0.2066 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3069    1.2929    0.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    1.4069   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7010    2.4207    0.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778    0.0416    0.0719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8408    0.1869   -0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7429   -0.9023   -0.7645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1544   -2.2024   -0.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -0.7857   -0.5049 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1006   -1.6166    0.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931    1.0429   -0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.2098    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761   -0.4484    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826    1.1948   -1.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670    1.5556   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652    2.5076   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -0.2701    1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -0.6975   -0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -0.7014   -1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -2.8329   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654   -1.1282   -1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4880   -2.4759    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  4 16  1  0
  5 17  1  0
  6 18  1  1
  7 19  1  0
  8 20  1  6
  9 21  1  0
 10 22  1  6
 11 23  1  0
M  END
Download

3D SDF for NP0001115 (L-Fucose)


  Mrv1652307301920042D          

 16 16  0  0  1  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
 10  6  1  0  0  0  0
  2 11  1  0  0  0  0
 11  6  1  0  0  0  0
  2 12  1  1  0  0  0
  3 13  1  1  0  0  0
  4 14  1  1  0  0  0
  5 15  1  6  0  0  0
 16  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C)OC([H])(O)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1

> <INCHI_KEY>
SHZGCJCMOBCMKK-DHVFOXMCSA-N

> <FORMULA>
C6H12O5

> <MOLECULAR_WEIGHT>
164.1565

> <EXACT_MASS>
164.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
15.345932686336555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol

> <JCHEM_LOGP>
-1.885629251333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.724419195509512

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.30218058050956

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121738272477764

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
34.3797

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
L-fucose

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001115 (L-Fucose)

NP0001115
     RDKit          3D

 23 23  0  0  0  0  0  0  0  0999 V2000
    2.5740    0.5912    0.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1813    0.6105   -0.2066 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3069    1.2929    0.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988    1.4069   -0.0141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7010    2.4207    0.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5778    0.0416    0.0719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8408    0.1869   -0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7429   -0.9023   -0.7645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1544   -2.2024   -0.4530 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -0.7857   -0.5049 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1006   -1.6166    0.5546 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2931    1.0429   -0.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.2098    1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761   -0.4484    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826    1.1948   -1.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6670    1.5556   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652    2.5076   -0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6332   -0.2701    1.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2319   -0.6975   -0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -0.7014   -1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -2.8329   -1.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2654   -1.1282   -1.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4880   -2.4759    0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  6
  4 16  1  0
  5 17  1  0
  6 18  1  1
  7 19  1  0
  8 20  1  6
  9 21  1  0
 10 22  1  6
 11 23  1  0
M  END
Download

PDB for NP0001115 (L-Fucose)

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   11   12                                             
CONECT    3    2    4    7   13                                             
CONECT    4    3    5    8   14                                             
CONECT    5    4    6    9   15                                             
CONECT    6    5   10   11   16                                             
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    2    6                                                       
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    4                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END
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3D PDB for NP0001115 (L-Fucose)

COMPND    NP0001115
HETATM    1  C1  UNL     1       2.574   0.591   0.355  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.181   0.610  -0.207  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.307   1.293   0.652  1.00  0.00           O  
HETATM    4  C3  UNL     1      -0.899   1.407  -0.014  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.701   2.421   0.459  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.578   0.042   0.072  1.00  0.00           C  
HETATM    7  O3  UNL     1      -2.841   0.187  -0.478  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.743  -0.902  -0.764  1.00  0.00           C  
HETATM    9  O4  UNL     1      -1.154  -2.202  -0.453  1.00  0.00           O  
HETATM   10  C6  UNL     1       0.723  -0.786  -0.505  1.00  0.00           C  
HETATM   11  O5  UNL     1       1.101  -1.617   0.555  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.293   1.043  -0.378  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.638   1.210   1.279  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.876  -0.448   0.636  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.183   1.195  -1.161  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.667   1.556  -1.095  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.465   2.508  -0.174  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.633  -0.270   1.128  1.00  0.00           H  
HETATM   19  H8  UNL     1      -3.232  -0.697  -0.729  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.023  -0.701  -1.831  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.693  -2.833  -1.076  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.265  -1.128  -1.423  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.488  -2.476   0.245  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   10   15
CONECT    3    4
CONECT    4    5    6   16
CONECT    5   17
CONECT    6    7    8   18
CONECT    7   19
CONECT    8    9   10   20
CONECT    9   21
CONECT   10   11   22
CONECT   11   23
END
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SMILES for NP0001115 (L-Fucose)

[H][C@@]1(C)OC([H])(O)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])O
Download

INCHI for NP0001115 (L-Fucose)

InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1
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View in JSmol
Synonyms
ValueSource
(-)-L-FucoseChEBI
(3S,4R,5R,6S)-6-Methyloxane-2,3,4,5-tetrolChEBI
(3S,4R,5R,6S)-6-Methyltetrahydropyran-2,3,4,5-tetrolChEBI
(3S,4R,5S,6S)-6-Methyloxane-2,3,4,5-tetrolChEBI
6-Deoxy-L-galactoseChEBI
WURCS=2.0/1,1,0/[a1221m-1x_1-5]/1/ChEBI
(-)-FucoseHMDB
6-Deoxy-L-galactopyranoseHMDB
6-DesoxygalactoseHMDB
6-Methyloxane-2,3,4,5-tetrolHMDB
6-Methyltetrahydropyran-2,3,4,5-tetraolHMDB
FucoseHMDB, MeSH
IsodulcitHMDB
L-(-)-FucoseHMDB
L-FucopyranoseHMDB
L-GalactomethyloseHMDB
RhodeoseHMDB
alpha FucoseMeSH, HMDB
alpha-FucoseMeSH, HMDB
DeoxygalactoseMeSH, HMDB
Chemical FormulaC6H12O5
Average Mass164.1565 Da
Monoisotopic Mass164.06847 Da
IUPAC Name(3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional NameL-fucose
CAS Registry Number2438-80-4
SMILES
C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1
InChI KeySHZGCJCMOBCMKK-DHVFOXMCSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-07-15View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Arabidopsis thalianaPlant
Ascoseira mirabilisLOTUS Database
Averrhoa carambolaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Carum carviFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Fucus spp.Plant
Gallus gallusFooDB
Homo sapiens (Urine)Animalia
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Linum usitatissimumFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Prunus aviumKNApSAcK Database
Saccharina japonicaPlant
Solanum lycopersicumFooDB
Solanum lycopersicum L.KNApSAcK Database
Solanum tuberosumFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vigna radiataFooDB
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling Point323.90 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility985 mg/mLNot Available
LogP-0.340 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility827 g/LALOGPS
logP-1.9ChemAxon
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020543
KNApSAcK IDC00035100
Chemspider ID16190
KEGG Compound IDC01019
BioCyc IDL-FUCOSE
BiGG IDNot Available
Wikipedia LinkL-Fucose
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID2181
Good Scents IDrw1687501
References
General References
  1. Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. [PubMed:3757018 ]
  2. Condaminet B, Peguet-Navarro J, Stahl PD, Dalbiez-Gauthier C, Schmitt D, Berthier-Vergnes O: Human epidermal Langerhans cells express the mannose-fucose binding receptor. Eur J Immunol. 1998 Nov;28(11):3541-51. [PubMed:9842897 ]
  3. Havenaar EC, Hoff RC, van den Eijnden DH, van Dijk W: Sialyl Lewis(x) epitopes do not occur on acute phase proteins in mice: relationship to the absence of alpha3-fucosyltransferase in the liver. Glycoconj J. 1998 Apr;15(4):389-95. [PubMed:9613826 ]
  4. Roelfzema H, van Erp PE: Studies on the plasma membrane of normal and psoriatic keratinocytes. 6. Cell surface and shed glycoproteins. J Invest Dermatol. 1983 Jan;80(1):24-6. [PubMed:6184420 ]
  5. Wiese TJ, Dunlap JA, Yorek MA: Effect of L-fucose and D-glucose concentration on L-fucoprotein metabolism in human Hep G2 cells and changes in fucosyltransferase and alpha-L-fucosidase activity in liver of diabetic rats. Biochim Biophys Acta. 1997 Apr 17;1335(1-2):61-72. [PubMed:9133643 ]
  6. Isnard N, Fodil-Bourahla I, Robert AM, Robert L: Pharmacology of skin aging. Stimulation of glycosaminoglycan biosynthesis by L-fucose and fucose-rich polysaccharides, effect of in vitro aging of fibroblasts. Biomed Pharmacother. 2004 Apr;58(3):202-4. [PubMed:15082343 ]
  7. Rizzi M, Tonetti M, Vigevani P, Sturla L, Bisso A, Flora AD, Bordo D, Bolognesi M: GDP-4-keto-6-deoxy-D-mannose epimerase/reductase from Escherichia coli, a key enzyme in the biosynthesis of GDP-L-fucose, displays the structural characteristics of the RED protein homology superfamily. Structure. 1998 Nov 15;6(11):1453-65. [PubMed:9817848 ]
  8. Gheri G, Sgambati E, Thyrion GD, Vichi D, Orlandini GE: The oligosaccharidic content of the glycoconjugates of the prepubertal descended and undescended testis: lectin histochemical study. Ital J Anat Embryol. 2004 Apr-Jun;109(2):69-84. [PubMed:15481156 ]
  9. Fediv OI, Kolomoiets' MIu: [Role of cytokines in the metabolism of the extracellular matrix carbohydrate-protein components in patients of various ages with gastroduodenal ulcer]. Lik Sprava. 2001 Jul-Aug;(4):181-2. [PubMed:11692712 ]
  10. Hutchinson WL, Du MQ, Johnson PJ, Williams R: Fucosyltransferases: differential plasma and tissue alterations in hepatocellular carcinoma and cirrhosis. Hepatology. 1991 Apr;13(4):683-8. [PubMed:1849114 ]
  11. Fleischer M, Przondo-Mordarska A: [Adhesins of Acinetobacter strains]. Med Dosw Mikrobiol. 1998;50(3-4):229-37. [PubMed:10222738 ]
  12. Gohlke M, Baude G, Nuck R, Grunow D, Kannicht C, Bringmann P, Donner P, Reutter W: O-linked L-fucose is present in Desmodus rotundus salivary plasminogen activator. J Biol Chem. 1996 Mar 29;271(13):7381-6. [PubMed:8631761 ]
  13. Chien CM, Cheng JL, Chang WT, Tien MH, Tsao CM, Chang YH, Chang HY, Hsieh JF, Wong CH, Chen ST: Polysaccharides of Ganoderma lucidum alter cell immunophenotypic expression and enhance CD56+ NK-cell cytotoxicity in cord blood. Bioorg Med Chem. 2004 Nov 1;12(21):5603-9. [PubMed:15465338 ]
  14. Hanisch FG, Heimbuchel G, Baldus SE, Uhlenbruck G, Schmits R, Pfreundschuh M, Schwonzen M, Vierbuchen M, Bara J, Peter-Katalinic J: Monoclonal antibody FW6 defines an epitope on alpha 3/4-monofucosylated polylactosaminoglycans expressed by fetal and colon carcinoma-associated mucins. Cancer Res. 1993 Sep 15;53(18):4367-75. [PubMed:8364932 ]
  15. Tonetti M, Sturla L, Bisso A, Zanardi D, Benatti U, De Flora A: The metabolism of 6-deoxyhexoses in bacterial and animal cells. Biochimie. 1998 Nov;80(11):923-31. [PubMed:9893952 ]
  16. Sato T, Sato M, Kiyohara K, Sogabe M, Shikanai T, Kikuchi N, Togayachi A, Ishida H, Ito H, Kameyama A, Gotoh M, Narimatsu H: Molecular cloning and characterization of a novel human beta1,3-glucosyltransferase, which is localized at the endoplasmic reticulum and glucosylates O-linked fucosylglycan on thrombospondin type 1 repeat domain. Glycobiology. 2006 Dec;16(12):1194-206. Epub 2006 Aug 9. [PubMed:16899492 ]
  17. Coyne MJ, Reinap B, Lee MM, Comstock LE: Human symbionts use a host-like pathway for surface fucosylation. Science. 2005 Mar 18;307(5716):1778-81. [PubMed:15774760 ]
  18. Quirk S, Seley KL: Substrate discrimination by the human GTP fucose pyrophosphorylase. Biochemistry. 2005 Aug 16;44(32):10854-63. [PubMed:16086588 ]
  19. Bathi RJ, Nandimath K, Kannan N, Shetty P: Evaluation of glycoproteins as prognosticators in head and neck malignancy. Indian J Dent Res. 2001 Apr-Jun;12(2):93-9. [PubMed:11665403 ]
  20. Sakai T, Yamamoto K, Yokota H, Hakozaki-Usui K, Hino F, Kato I: Rapid, simple enzymatic assay of free L-fucose in serum and urine, and its use as a marker for cancer, cirrhosis, and gastric ulcers. Clin Chem. 1990 Mar;36(3):474-6. [PubMed:2311216 ]
  21. Yamauchi M, Kimura K, Maezawa Y, Ohata M, Mizuhara Y, Hirakawa J, Nakajima H, Toda G: Urinary level of L-fucose as a marker of alcoholic liver disease. Alcohol Clin Exp Res. 1993 Apr;17(2):268-71. [PubMed:8488966 ]
  22. Sustic T, Van Coillie J, Larsen MD, Derksen NIL, Szittner Z, Nouta J, Wang W, Damelang T, Rebergen I, Linty F, Visser R, Mok JY, Geerdes DM, van Esch WJE, de Taeye SW, van Gils MJ, van de Watering L, van der Schoot CE, Wuhrer M, Rispens T, Vidarsson G: Immunoassay for quantification of antigen-specific IgG fucosylation. EBioMedicine. 2022 Jun 22;81:104109. doi: 10.1016/j.ebiom.2022.104109. [PubMed:35752106 ]