MiMeDB: Showing metabocard for Glucose 1-phosphate (MMDBc0029673)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:36:58 UTC

Update Date

2024-10-10 00:40:42 UTC

Metabolite ID

MMDBc0029673

Metabolite Identification

Common Name

Glucose 1-phosphate

Description

Glucose 1-phosphate is the direct product of the reaction in which glycogen phosphorylase cleaves off a molecule of glucose from a greater glycogen structure. Glycogen phosphorylase, the product of the glgP Gene, catalyzes glycogen breakdown by removing glucose units from the nonreducing ends in Escherichia coli. It cannot travel down many metabolic pathways and must be interconverted by the enzyme phosphoglucomutase in order to become glucose 6-phosphate. In glycogenesis, free glucose 1-phosphate can also react with UTP to form UDP-glucose, by using the enzyme UDP-glucose pyrophosphorylase. Periplasmic acid glucose-1-phosphatase (G-1-Pase) encoded by gene Agp is necessary for the growth of Escherichia coli in a minimal medium containing glucose-1-phosphate (G-1-P) as the sole source of carbon.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0001586
     RDKit          3D
Glucose 1-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.5555   -0.3068   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285    0.6395   -0.0476 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.7478    0.4664    1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1611    2.2535   -0.5172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125    0.3472    0.2125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6828   -0.3676   -0.7686 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3519    0.4155   -1.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0573    0.9245   -0.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2006    1.7578   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.7971   -1.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -0.1327    0.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.4810    1.8283 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413   -1.2530    1.0180 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5111   -2.3520    1.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -1.6333   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9024   -2.6637   -0.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -0.4781    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2303    2.3527   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -0.6606   -1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    1.5820    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998    2.1531    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8116    1.0281   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    2.6010   -1.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611   -0.5258    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -0.0046    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -0.9789    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -3.0138    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   -1.9112   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695   -3.5176   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  6  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  6
  8 20  1  1
  9 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  6
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END


  Mrv1652304222018242D          

 16 16  0  0  1  0            999 V2000
10039.459210045.7686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10038.738910046.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10039.459210044.9458    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10038.022210045.7686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10038.738910044.5288    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10040.172010044.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10038.022210044.9458    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10037.317210046.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10038.738910043.7062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10037.317210044.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10036.598610045.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10040.173810046.1780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10040.171810047.0066    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10040.999910047.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10039.457310047.4191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10040.586910047.7208    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
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  6  0  0  0
  4  7  1  0  0  0  0
  4  8  1  1  0  0  0
  5  9  1  1  0  0  0
  7 10  1  6  0  0  0
  5  7  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
  1 12  1  6  0  0  0
  8 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029673

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1

> <INCHI_KEY>
HXXFSFRBOHSIMQ-VFUOTHLCSA-N

> <FORMULA>
C6H13O9P

> <MOLECULAR_WEIGHT>
260.1358

> <EXACT_MASS>
260.029718526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.724647975194152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-3.056105249333333

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.2188934582423325

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1553718480897146

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810995814615806

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
46.796299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-D-glucose 1-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001586
     RDKit          3D
Glucose 1-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.5555   -0.3068   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285    0.6395   -0.0476 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.7478    0.4664    1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1611    2.2535   -0.5172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125    0.3472    0.2125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6828   -0.3676   -0.7686 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3519    0.4155   -1.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0573    0.9245   -0.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2006    1.7578   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.7971   -1.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -0.1327    0.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.4810    1.8283 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413   -1.2530    1.0180 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5111   -2.3520    1.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -1.6333   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9024   -2.6637   -0.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -0.4781    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2303    2.3527   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -0.6606   -1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    1.5820    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998    2.1531    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8116    1.0281   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    2.6010   -1.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611   -0.5258    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -0.0046    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -0.9789    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -3.0138    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   -1.9112   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695   -3.5176   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  6  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  6
  8 20  1  1
  9 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  6
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  C   UNK     0    8740.3248752.101   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8738.9798752.866   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8740.3248750.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8737.6428752.101   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8738.9798749.787   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8741.6548749.787   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8737.6428750.566   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8736.3258752.866   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8738.9798748.251   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8736.3258749.787   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8734.9848752.096   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8741.6588752.866   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0    8741.6548754.412   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0    8743.2008754.410   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8740.3208755.182   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8742.4298755.745   0.000  0.00  0.00           O+0
CONECT    1    2    3   12                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    3    9    7                                                  
CONECT    6    3                                                            
CONECT    7    4   10    5                                                  
CONECT    8    4   11                                                       
CONECT    9    5                                                            
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12   13    1                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001586
HETATM    1  O1  UNL     1      -3.556  -0.307  -1.039  1.00  0.00           O  
HETATM    2  P1  UNL     1      -2.929   0.639  -0.048  1.00  0.00           P  
HETATM    3  O2  UNL     1      -3.748   0.466   1.441  1.00  0.00           O  
HETATM    4  O3  UNL     1      -3.161   2.254  -0.517  1.00  0.00           O  
HETATM    5  O4  UNL     1      -1.312   0.347   0.213  1.00  0.00           O  
HETATM    6  C1  UNL     1      -0.683  -0.368  -0.769  1.00  0.00           C  
HETATM    7  O5  UNL     1       0.352   0.416  -1.283  1.00  0.00           O  
HETATM    8  C2  UNL     1       1.057   0.924  -0.197  1.00  0.00           C  
HETATM    9  C3  UNL     1       2.201   1.758  -0.774  1.00  0.00           C  
HETATM   10  O6  UNL     1       1.745   2.797  -1.559  1.00  0.00           O  
HETATM   11  C4  UNL     1       1.671  -0.133   0.666  1.00  0.00           C  
HETATM   12  O7  UNL     1       2.139   0.481   1.828  1.00  0.00           O  
HETATM   13  C5  UNL     1       0.741  -1.253   1.018  1.00  0.00           C  
HETATM   14  O8  UNL     1       1.511  -2.352   1.389  1.00  0.00           O  
HETATM   15  C6  UNL     1      -0.018  -1.633  -0.238  1.00  0.00           C  
HETATM   16  O9  UNL     1      -0.902  -2.664  -0.051  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.852  -0.478   1.693  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.230   2.353  -1.498  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.332  -0.661  -1.613  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.419   1.582   0.440  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.800   2.153   0.058  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.812   1.028  -1.377  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.856   2.601  -1.922  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.561  -0.526   0.137  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.862  -0.005   2.644  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.034  -0.979   1.822  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.584  -3.014   0.648  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.748  -1.911  -0.997  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.370  -3.518  -0.116  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   17
CONECT    4   18
CONECT    5    6
CONECT    6    7   15   19
CONECT    7    8
CONECT    8    9   11   20
CONECT    9   10   21   22
CONECT   10   23
CONECT   11   12   13   24
CONECT   12   25
CONECT   13   14   15   26
CONECT   14   27
CONECT   15   16   28
CONECT   16   29
END

HMDB0001586
     RDKit          3D
Glucose 1-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.5555   -0.3068   -1.0394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285    0.6395   -0.0476 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.7478    0.4664    1.4411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1611    2.2535   -0.5172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125    0.3472    0.2125 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6828   -0.3676   -0.7686 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3519    0.4155   -1.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0573    0.9245   -0.1967 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2006    1.7578   -0.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.7971   -1.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -0.1327    0.6655 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1389    0.4810    1.8283 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413   -1.2530    1.0180 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5111   -2.3520    1.3895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -1.6333   -0.2382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9024   -2.6637   -0.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -0.4781    1.6927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2303    2.3527   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -0.6606   -1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4190    1.5820    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7998    2.1531    0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8116    1.0281   -1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    2.6010   -1.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5611   -0.5258    0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -0.0046    2.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -0.9789    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -3.0138    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   -1.9112   -0.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3695   -3.5176   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  6  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  6
  8 20  1  1
  9 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  6
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  6
 16 29  1  0
M  END

Synonyms

Value	Source
1-O-Phosphono-alpha-D-glucopyranose	ChEBI
alpha-D-Glucopyranosyl phosphate	ChEBI
alpha-D-Glucose-1-phosphate	ChEBI
Cori ester	ChEBI, KEGG
D-Glucose 1-phosphate	ChEBI
D-Glucose alpha-1-phosphate	ChEBI, KEGG
1-O-Phosphono-a-D-glucopyranose	Generator
1-O-Phosphono-α-D-glucopyranose	Generator
Glucose 1-phosphoric acid	Generator
a-D-Glucopyranosyl phosphate	Generator
a-D-Glucopyranosyl phosphoric acid	Generator
alpha-D-Glucopyranosyl phosphoric acid	Generator
α-D-Glucopyranosyl phosphate	Generator
α-D-Glucopyranosyl phosphoric acid	Generator
a-D-Glucose-1-phosphate	Generator
a-D-Glucose-1-phosphoric acid	Generator
alpha-D-Glucose-1-phosphoric acid	Generator
α-D-Glucose-1-phosphate	Generator
α-D-Glucose-1-phosphoric acid	Generator
D-Glucose 1-phosphoric acid	Generator
D-Glucose a-1-phosphate	Generator
D-Glucose a-1-phosphoric acid	Generator
D-Glucose alpha-1-phosphoric acid	Generator
D-Glucose α-1-phosphate	Generator
D-Glucose α-1-phosphoric acid	Generator
alpha-Glucose-1-phosphate	MeSH
alpha-D-Glucose 1-phosphate	KEGG
a-D-Glucose 1-phosphate	Generator
a-D-Glucose 1-phosphoric acid	Generator
alpha-D-Glucose 1-phosphoric acid	Generator
α-D-Glucose 1-phosphoric acid	Generator
Glucose-1-phosphate	MeSH
Glucose 1-phosphate	HMDB
Glucose monophosphate	HMDB
α-D-Glucose 1-phosphate	HMDB

Molecular Formula

C₆H₁₃O₉P

Average Mass

260.1358

Monoisotopic Mass

260.029718526

IUPAC Name

{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional Name

α-D-glucose 1-phosphate

CAS Registry Number

59-56-3

SMILES

OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1

InChI Key

HXXFSFRBOHSIMQ-VFUOTHLCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Alkyl phosphate
Phosphoric acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucopyranose 1-phosphate (CHEBI:29042 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	32.3 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.1	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	1.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.8 m³·mol⁻¹	ChemAxon
Polarizability	20.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces
Fibroblasts
Saliva

Tissue Locations

Fibroblasts

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191790	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	Unknown	P22413	Homo sapiens
MMDBp0191865	Ectonucleotide pyrophosphatase/phosphodiesterase family member 3	Unknown	O14638	Homo sapiens
MMDBp0192037	Glycogen phosphorylase, liver form	Enzyme	P06737	Homo sapiens
MMDBp0192040	Glycogen phosphorylase, muscle form	Enzyme	P11217	Homo sapiens
MMDBp0192042	Glycogen phosphorylase, brain form	Enzyme	P11216	Homo sapiens
MMDBp0192680	UTP--glucose-1-phosphate uridylyltransferase	Enzyme	Q16851	Homo sapiens
MMDBp0192698	Galactose-1-phosphate uridylyltransferase	Unknown	P07902	Homo sapiens
MMDBp0192703	Uridine diphosphate glucose pyrophosphatase	Unknown	O95848	Homo sapiens
MMDBp0191639	Phosphoglucomutase-1	Enzyme	P36871	Escherichia coli
MMDBp0193141	Phosphoacetylglucosamine mutase	Unknown	O95394	Homo sapiens
MMDBp0193267	Glucosylceramidase	Enzyme	P04062	Homo sapiens
MMDBp0193931	Phosphoglucomutase-2	Unknown	Q96G03	Homo sapiens
MMDBp0195900	Glucose 1,6-bisphosphate synthase	Enzyme	Q6PCE3	Homo sapiens
MMDBp0196816	GDP-D-glucose phosphorylase 1	Unknown	Q6ZNW5

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018322	Uridine triphosphate	Uridine diphosphate glucose	UTP--glucose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0018431	Galactose 1-phosphate	Uridine diphosphategalactose	Galactose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0018466	Glucose 6-phosphate	Glucose 1-phosphate	Phosphoglucomutase-1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0018467	Glucose 1-phosphate	ADP-Glucose	Glucose-1-phosphate adenylyltransferase	Reversible transfer of an adenylyl group	PathBank	31602464
MMDBr0018472	Glucose 1-phosphate	Galactose 1-phosphate	Galactose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0018595	Amylose	Glycogen	Maltodextrin phosphorylase	Phosphorylation	PathBank	31602464
MMDBr0018597	Glucose 6-phosphate	Glucose 1-phosphate	Phosphoglucomutase-1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0018598	Glucose 1-phosphate	ADP-Glucose	Glucose-1-phosphate adenylyltransferase	Reversible transfer of an adenylyl group	PathBank	31602464
MMDBr0018605	D-Fructose	Sucrose	Glucosylglycerate phosphorylase	Phosphorylation	PathBank	31602464
MMDBr0018606	Glycogen	Dextrin	Glycogen phosphorylase	Phosphorylation	PathBank	31602464
MMDBr0018608	Maltotetraose	Maltotriose	Maltodextrin phosphorylase	Phosphorylation	PathBank	31602464
MMDBr0018631	Glucose 6-phosphate	Glucose 1-phosphate	Phosphoglucomutase-1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0018639	Uridine triphosphate	Uridine diphosphate glucose	UTP--glucose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0018669	Thymidine 5'-triphosphate	dTDP-D-Glucose	Glucose-1-phosphate thymidylyltransferase 1		PathBank	31602464
MMDBr0018670	Thymidine 5'-triphosphate	dTDP-D-Glucose	Glucose-1-phosphate thymidylyltransferase 2		PathBank	31602464
MMDBr0019238	Thymidine 5'-triphosphate	TDP-Glucose	Glucose-1-phosphate thymidylyltransferase 2		PathBank	31602464
MMDBr0019259	Thymidine 5'-triphosphate	dTDP-D-Glucose	Glucose-1-phosphate thymidylyltransferase 2		PathBank	31602464
MMDBr0019340	Thymidine 5'-triphosphate	dTDP-D-Glucose	Glucose-1-phosphate thymidylyltransferase 1		PathBank	31602464
MMDBr0019464	Glucose 1-phosphate	D-Glucose	Unknown Protein		PathBank	31602464
MMDBr0019490	Galactose 1-phosphate	Uridine diphosphategalactose	Galactose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0019492	Glucose 1-phosphate	Glucose 6-phosphate	Phosphoglucomutase 1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0019493	Uridine triphosphate	Uridine 5'-diphosphate	UTP--glucose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0019561	beta-D-Glucose 6-phosphate	Glucose 1-phosphate	Phosphoglucomutase 1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0019562	Uridine diphosphategalactose	Galactose 1-phosphate	Galactose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0019885	Glyceric acid 1,3-biphosphate	alpha-D-Glucose 1,6-bisphosphate	Phosphoribomutase		PathBank	31602464
MMDBr0019886	Uridine triphosphate	Uridine diphosphate glucose	Probable UTP--glucose-1-phosphate uridylyltransferase	Transfer of an uridylyl group	PathBank	31602464
MMDBr0019894	Glycogen	Amylose	Unknown Protein		PathBank	31602464
MMDBr0024594	Cytidine triphosphate	diphosphate	Probable glucose-1-phosphate cytidylyltransferase	Transfer of a cytidylyl group	RHEA	34755880
MMDBr0025013	Phosphate	Glucose 1-phosphate	Maltodextrin phosphorylase	Phosphorylation	RHEA	34755880
MMDBr0025275	Phosphate	Glucose 1-phosphate	1,2-beta-oligoglucan phosphorylase	Phosphorylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease		Association	Human Saliva	HMDB	23857558
Frontotemporal dementia		Association	Human Saliva	HMDB	23857558

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	12	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; Chicken ; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	431	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	320	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; Chicken ; Human subgingival plaque	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	19	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	149	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	29	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	2	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	7	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	10	Human feces; Human saliva	Unknown
Bacteria/Eubacteria	Cyanobacteria	11
Bacteria/Eubacteria	Deinococcus-thermus	6
Bacteria/Eubacteria	Thermotogae	8
Bacteria/Eubacteria	Gemmatimonadetes	1
Bacteria/Eubacteria	Acidobacteria	1
Bacteria	nah	1
Bacteria	Deinococcus-thermus	1
Bacteria/Eubacteria	Chloroflexi	1
Bacteria/Eubacteria	Nitrospirae	1
Eukaryota/Fungi	Basidiomycota	5
Archaea/Archaea	Crenarchaeota	1		Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	3		Metabolic reconstruction
Eukaryota/Fungi	Microsporidia	1

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Saliva	Detected and Quantified	1.07	0.26	uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Saliva	Detected and Quantified	0.94	0.22	uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Saliva	Detected and Quantified	2.26	2.53	uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Saliva	Detected and Quantified	1.32	0.69	uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Fibroblasts	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001586

DrugBank ID

DB02843

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glucose-1-phosphate

METLIN ID

Not Available

PubChem Compound

65533

PDB ID

Not Available

ChEBI ID

29042

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Lederer B, Van Hoof F, Van den Berghe G, Hers H: Glycogen phosphorylase and its converter enzymes in haemolysates of normal human subjects and of patients with type VI glycogen-storage disease. A study of phosphorylase kinase deficiency. Biochem J. 1975 Apr;147(1):23-35. doi: 10.1042/bj1470023. [PubMed:168880 ]
Krause EG, Will H, Bohm M, Wollenberger A: The assay of glycogen phosphorylase in human blood serum and its application to the diagnosis of myocardial infarction. Clin Chim Acta. 1975 Jan 20;58(2):145-54. doi: 10.1016/s0009-8981(75)80006-4. [PubMed:1122638 ]
Nakashima H, Suo H, Ochiai J, Sugie H, Kawamura Y: [A case of adult onset phosphoglucomutase deficiency]. Rinsho Shinkeigaku. 1992 Jan;32(1):42-7. [PubMed:1385770 ]
Kamei A: Glycation and insolubility of human lens protein. Chem Pharm Bull (Tokyo). 1992 Oct;40(10):2787-91. doi: 10.1248/cpb.40.2787. [PubMed:1464110 ]
Suzuki K, Kayamori Y, Katayama Y: Development of an enzymatic method for the assay of serum magnesium using phosphoglucomutase and glucose-6-phosphate dehydrogenase. Clin Biochem. 1991 Jun;24(3):249-53. doi: 10.1016/0009-9120(91)80015-u. [PubMed:1831412 ]
Kamei A, Kato M: Contribution of glycation to human lens coloration. Chem Pharm Bull (Tokyo). 1991 May;39(5):1272-6. doi: 10.1248/cpb.39.1272. [PubMed:1914002 ]
Yamada Y, Kono N, Nakajima H, Shimizu T, Kiyokawa H, Kawachi M, Ono A, Nishimura T, Kuwajima M, Tarui S: Low glucose-1, 6-bisphosphate and high fructose-2, 6-bisphosphate concentrations in muscles of patients with glycogenosis types VII and V. Biochem Biophys Res Commun. 1991 Apr 15;176(1):7-10. doi: 10.1016/0006-291x(91)90881-7. [PubMed:2018547 ]
Kodentsova VM, Glinka EIu: [Changes in kinetic properties of pyridoxal-dependent enzymes during dietary vitamin B6 deficiency in rats]. Ukr Biokhim Zh (1978). 1990 Jan-Feb;62(1):44-9. [PubMed:2110692 ]
Reinken L, Obladen M, Dockx-Reinken F, Lindemann C: [The effect of osteopenia prevention in very small premature infants on hormonal parameters of calcium metabolism and bone mineralization]. Klin Padiatr. 1989 May-Jun;201(3):177-82. doi: 10.1055/s-2007-1025298. [PubMed:2739343 ]
Arthur PG, Kent JC, Hartmann PE: Microanalysis of the metabolic intermediates of lactose synthesis in human milk and plasma using bioluminescent methods. Anal Biochem. 1989 Feb 1;176(2):449-56. doi: 10.1016/0003-2697(89)90341-2. [PubMed:2742136 ]
Chen YT, Kato T: Liver-specific glucose-6-phosphatase is not present in human placenta. J Inherit Metab Dis. 1985;8(2):92-4. doi: 10.1007/BF01801675. [PubMed:3023746 ]
Pezzarossa A, Cavazzini G, Coscelli C, Butturini U: [Modifications induced by glucose-1-phosphate on carbohydrate utilization curve after venous loading. Results in normal subjects (preliminary note)]. Boll Soc Ital Biol Sper. 1972 Jun 30;48(12):318-21. [PubMed:5070100 ]
Lang A, Groebe H, Hellkuhl B, von Figura K: A new variant of galactosemia: galactose-1-phosphate uridylytransferase sensitive to product inhibition by glucose 1-phosphate. Pediatr Res. 1980 May;14(5):729-34. doi: 10.1203/00006450-198005000-00005. [PubMed:6247691 ]
Gella FJ, Cusso R: Glycogen phosphorylase from normal and leukemic human leucocytes: kinetic parameters of the active form. Rev Esp Fisiol. 1980 Mar;36(1):1-6. [PubMed:7394270 ]
Bollaert PE, Levy B, Nace L, Laterre PF, Larcan A: Hemodynamic and metabolic effects of rapid correction of hypophosphatemia in patients with septic shock. Chest. 1995 Jun;107(6):1698-701. doi: 10.1378/chest.107.6.1698. [PubMed:7781370 ]
Palombi M, Bochicchio O, Gargiulo M, Sammarco M: [Alternative therapy of deep venous thrombosis in patients at hemorrhagic risk]. Minerva Chir. 1994 Mar;49(3):189-94. [PubMed:8028729 ]
Mahadevan-Jansen A, Mitchell MF, Ramanujam N, Malpica A, Thomsen S, Utzinger U, Richards-Kortum R: Near-infrared Raman spectroscopy for in vitro detection of cervical precancers. Photochem Photobiol. 1998 Jul;68(1):123-32. doi: 10.1562/0031-8655(1998)068<0123:nirsfv>2.3.co;2. [PubMed:9679458 ]
Gannon MC, Khan MA, Nuttall FQ: Glucose appearance rate after the ingestion of galactose. Metabolism. 2001 Jan;50(1):93-8. doi: 10.1053/meta.2001.19442. [PubMed:11172481 ]
Leuzzi R, Fulceri R, Marcolongo P, Banhegyi G, Zammarchi E, Stafford K, Burchell A, Benedetti A: Glucose 6-phosphate transport in fibroblast microsomes from glycogen storage disease type 1b patients: evidence for multiple glucose 6-phosphate transport systems. Biochem J. 2001 Jul 15;357(Pt 2):557-62. doi: 10.1042/0264-6021:3570557. [PubMed:11439108 ]
Lai K, Elsas LJ: Structure-function analyses of a common mutation in blacks with transferase-deficiency galactosemia. Mol Genet Metab. 2001 Sep-Oct;74(1-2):264-72. doi: 10.1006/mgme.2001.3230. [PubMed:11592823 ]

Showing metabocard for Glucose 1-phosphate (MMDBc0029673)

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Structure for #<Metabolite:0x00007f9238e3d858>

3D Structure for #<Metabolite:0x00007f9238e3d858>