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Showing NP-Card for D-Fructose (NP0000381)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:33 UTC
NP-MRD IDNP0000381
Secondary Accession NumbersNone
Natural Product 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 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).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000381 (D-Fructose)

 
  Mrv1652309042000052D          
 
 12 12  0  0  1  0            999 V2000
   13.7615   -8.7825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5106   -9.5454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0777   -8.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3388   -8.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5175   -9.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6790   -9.5454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9951  -10.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4110   -8.7654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0914   -8.5385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1979  -10.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6240   -8.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1292   -9.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  6  0  0  0
  8 11  1  1  0  0  0
 11 12  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000381 (D-Fructose)

HMDB0000660
     RDKit          3D
D-Fructose
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.9336   -0.0753    0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    0.4308   -0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1034    0.3993   -0.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119    1.1351    0.1680 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115    0.5630    0.3915 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9193    0.0682    1.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9061    1.5817    0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679    1.0558    0.4120 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -0.6137   -0.5490 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6968   -1.6385   -0.0155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5324   -0.9868   -0.6560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7933   -1.7821   -1.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.7097    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9211    1.4848   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -0.1402   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990    0.7793   -1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4113   -0.7905    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481    2.3685    0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8251    2.0988   -0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2273    0.0879    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -0.3029   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142   -2.4160   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048   -1.4215    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872   -2.5953   -1.3980 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
  5  6  1  1
  5  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  6
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  6
 10 22  1  0
 11 23  1  1
 12 24  1  0
M  END
Download

3D SDF for NP0000381 (D-Fructose)

 
  Mrv1652309042000052D          
 
 12 12  0  0  1  0            999 V2000
   13.7615   -8.7825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5106   -9.5454    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0777   -8.2877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3388   -8.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5175   -9.0575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6790   -9.5454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9951  -10.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4110   -8.7654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.0914   -8.5385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1979  -10.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6240   -8.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1292   -9.1811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  6  0  0  0
  8 11  1  1  0  0  0
 11 12  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000381

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C6H12O6

> <MOLECULAR_WEIGHT>
180.1559

> <EXACT_MASS>
180.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.264519672327737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol

> <ALOGPS_LOGP>
-2.45

> <JCHEM_LOGP>
-2.7579993179999995

> <ALOGPS_LOGS>
0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.727992395711098

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.284334729790022

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981428882582282

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
36.3608

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fructose

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000381 (D-Fructose)

HMDB0000660
     RDKit          3D
D-Fructose
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.9336   -0.0753    0.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5965    0.4308   -0.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1034    0.3993   -0.7540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4119    1.1351    0.1680 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115    0.5630    0.3915 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9193    0.0682    1.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9061    1.5817    0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1679    1.0558    0.4120 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -0.6137   -0.5490 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6968   -1.6385   -0.0155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5324   -0.9868   -0.6560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7933   -1.7821   -1.7328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.7097    1.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9211    1.4848   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -0.1402   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990    0.7793   -1.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4113   -0.7905    1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7481    2.3685    0.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8251    2.0988   -0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2273    0.0879    0.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -0.3029   -1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142   -2.4160   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8048   -1.4215    0.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872   -2.5953   -1.3980 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
  5  6  1  1
  5  7  1  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  6
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  9 21  1  6
 10 22  1  0
 11 23  1  1
 12 24  1  0
M  END
Download

PDB for NP0000381 (D-Fructose)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      25.688 -16.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.220 -17.818   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      24.412 -15.470   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      26.766 -15.291   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      27.099 -16.907   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.667 -17.818   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      26.124 -19.075   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      23.167 -16.362   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      28.171 -15.939   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.769 -19.082   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      21.698 -15.900   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      20.775 -17.138   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8                                                       
CONECT    4    1    9                                                       
CONECT    5    1                                                            
CONECT    6    2   10    8                                                  
CONECT    7    2                                                            
CONECT    8    3   11    6                                                  
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    8   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for NP0000381 (D-Fructose)

COMPND    HMDB0000660
HETATM    1  O1  UNL     1      -2.934  -0.075   0.691  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.596   0.431  -0.562  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.103   0.399  -0.754  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.412   1.135   0.168  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.812   0.563   0.391  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.919   0.068   1.691  1.00  0.00           O  
HETATM    7  C4  UNL     1       1.906   1.582   0.198  1.00  0.00           C  
HETATM    8  O4  UNL     1       3.168   1.056   0.412  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.954  -0.614  -0.549  1.00  0.00           C  
HETATM   10  O5  UNL     1       1.697  -1.638  -0.015  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.532  -0.987  -0.656  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.793  -1.782  -1.733  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.217   0.710   1.255  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.921   1.485  -0.673  1.00  0.00           H  
HETATM   15  H3  UNL     1      -3.059  -0.140  -1.389  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.899   0.779  -1.787  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.411  -0.791   1.689  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.748   2.369   0.965  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.825   2.099  -0.785  1.00  0.00           H  
HETATM   20  H8  UNL     1       3.227   0.088   0.361  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.277  -0.303  -1.565  1.00  0.00           H  
HETATM   22  H10 UNL     1       1.614  -2.416  -0.622  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.805  -1.422   0.327  1.00  0.00           H  
HETATM   24  H12 UNL     1      -1.287  -2.595  -1.398  1.00  0.00           H  
CONECT    1    2   13
CONECT    2    3   14   15
CONECT    3    4   11   16
CONECT    4    5
CONECT    5    6    7    9
CONECT    6   17
CONECT    7    8   18   19
CONECT    8   20
CONECT    9   10   11   21
CONECT   10   22
CONECT   11   12   23
CONECT   12   24
END
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SMILES for NP0000381 (D-Fructose)

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

INCHI for NP0000381 (D-Fructose)

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
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View in JSmol
Synonyms
ValueSource
beta-D-Arabino-hexuloseChEBI
beta-D-FructoseChEBI
beta-Fruit sugarChEBI
beta-LevuloseChEBI
FRUCTOSEChEBI
b-D-Arabino-hexuloseGenerator
Β-D-arabino-hexuloseGenerator
b-D-FructoseGenerator
Β-D-fructoseGenerator
b-Fruit sugarGenerator
Β-fruit sugarGenerator
b-LevuloseGenerator
Β-levuloseGenerator
beta-D-FructofuranoseHMDB
beta-delta-Arabino-hexuloseHMDB
beta-delta-FructofuranoseHMDB
beta-delta-FructoseHMDB
D-(-)-FructoseHMDB
delta-(-)-FructoseHMDB
delta-FructoseHMDB
FRUHMDB
FructonHMDB
LevuloseHMDB
Braun brand OF fructoseHMDB
Fleboplast levulosaHMDB
Fresenius kabi brand OF fructoseHMDB
Instituto farmacologico brand OF fructoseHMDB
LevulosaHMDB
Levulosa ifeHMDB
Grifols brand OF fructoseHMDB
Levulosa baxterHMDB
Levulosado braunHMDB
Ern brand OF fructoseHMDB
Levulosa grifolsHMDB
Levulosa meinHMDB
Levulosado vituliaHMDB
Apir levulosaHMDB
Baxter brand OF fructoseHMDB
Bieffe brand OF fructoseHMDB
Levulosa braunHMDB
Levulosa ibysHMDB
Levulosa, apirHMDB
Levulosa, fleboplastHMDB
Levulosado bieffe meditHMDB
Plast apyr levulosa meinHMDB
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
IUPAC Name(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
Traditional 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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 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 Available2021-08-11View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anser anserFooDB
Anthriscus cerefoliumFooDB
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaPlant
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
    • Graeme A. King, Kate G. Henderson, Erin M. O'Donoghue, Wilhelmina Martin, Ross E. Lill. Flavour a...
AstacideaFooDB
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Belone beloneFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
Borago officinalisFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
BrachyuraFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Bubalus bubalisFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Canarium ovatumFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Centaurea bracteata Scop.Plant
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
ClupeinaeFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
CoregonusFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crassostrea virginicaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
CyclopteridaeFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Daphnia pulexLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • David M. Alabran, and Ahmed F. Mabrouk. Carrot flavor. Sugars and free nitrogenous compounds in f...
Detarium microcarpumLOTUS Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
EngraulidaeFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
EucheumaFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gallus gallusFooDB
Garcinia mangostanaFooDB
GastropodaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoidesFooDB
Homarus americanusFooDB
Homo sapiens (Serum)Animalia
Homo sapiens (Urine)Animalia
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Ictalurus punctatusFooDB
Illicium verumFooDB
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Lagopus mutaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
LeporidaeFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Limanda limandaFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Lota lotaFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Marsdenia tomentosaPlant
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Melanitta fuscaFooDB
Melanogrammus aeglefinusFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Micromesistius poutassouFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantiaFooDB
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
MytilidaeFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
NephropidaeFooDB
Nephrops norvegicusFooDB
Numida meleagrisFooDB
Nuphar luteaFooDB
Nyctanthes arbor-tristis Linn.Plant
Ocimum basilicumFooDB
Octopus vulgarisFooDB
OdocoileusFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Ovis ariesFooDB
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
PapaverFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
Pediomelum esculentumFooDB
PerciformesFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllanthus sellowianusPlant
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Piper nigrum L.FooDB
Piper retrofractum Vahl.Plant
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectidaeFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Polygonum alpinumFooDB
Polytrichum communePlant
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumPlant
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
RanidaeFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Rhodiola crenulataPlant
Rhodiola kirilowiiPlant
Rhodiola roseaPlant
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
Ruellia patulaLOTUS Database
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Saccharina japonicaFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
SalmonidaeFooDB
SalvelinusFooDB
Salvelinus namaycushFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sander luciopercaFooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
ScombridaeFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
SebastesFooDB
Sebastes alutusFooDB
Sebastes viviparusFooDB
Sebertia acuminataPlant
Secale cerealeFooDB
Sechium eduleFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
SiluriformesFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
SoleidaeFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Squalus acanthiasFooDB
Stenodus leucichthysFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiPlant
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
ThelespermaFooDB
Theobroma cacaoFooDB
ThunnusFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Pentose monosaccharide
  • Monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point119 - 122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility778 mg/mL at 20 °CYalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189.
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1110 g/LALOGPS
logP-2.4ALOGPS
logP-2.8ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.26 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000660
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031286
KNApSAcK IDC00001117
Chemspider ID388775
KEGG Compound IDC02336
BioCyc IDBETA-D-FRUCTOSE
BiGG ID33835
Wikipedia LinkFructose
METLIN ID135
PubChem Compound439709
PDB IDFRU
ChEBI ID28645
Good Scents IDNot Available
References
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 ]
  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 ]
  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 ]
  4. Andrade-Rocha FT: Seminal fructose levels in male infertility: relationship with sperm characteristics. Int Urol Nephrol. 1999;31(1):107-11. [PubMed:10408311 ]
  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 ]
  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 ]
  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 ]
  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 ]