MiMeDB: Showing metabocard for Glucose 6-phosphate (MMDBc0029643)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:35:49 UTC

Update Date

2024-04-30 19:39:58 UTC

Metabolite ID

MMDBc0029643

Metabolite Identification

Common Name

Glucose 6-phosphate

Description

Glucose 6 phosphate (alpha-D-glucose 6 phosphate or G6P) is the alpha-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer Glucose-6-phosphate is a phosphorylated glucose molecule on carbon 6. When glucose enters a cell, it is immediately phosphorylated to G6P. This is catalyzed with hexokinase enzymes, thus consuming one ATP. A major reason for immediate phosphorylation of the glucose is so that it cannot diffuse out of the cell. The phosphorylation adds a charged group so the G6P cannot easily cross cell membranes. G6P can travel down two metabolic pathways, glycolysis and the pentose phosphate pathway. Note, the molecule now has 2 phosphoryl groups attached. The addition of the 2nd phosphoryl group is an irreversible step, so once this happens G6P will enter glycolysis and be turned into pyruvate (ATP production occurs). After being converted to G6P, phosphoglucose mutase (isomerase) can turn the molecule into glucose-1-phosphate. Glucose-1-phosphate can then be combined with uridine triphosphate (UTP) to form UDP-glucose. This reaction is driven by the hydrolysis of pyrophosphate that is released in the reaction. (Wikipedia )

Structure

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

HMDB0001401
     RDKit          3D
Glucose 6-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.7621   -0.8900   -1.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -0.5530   -0.1389 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.5887    1.1337   -0.0092 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -1.1940    1.3564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -1.2043   -0.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3219   -0.5737    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -0.0543   -0.4876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6994   -1.1139   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0091   -0.7023   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0752    0.3912   -1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382   -0.4421    0.2649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9015    0.1105    0.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7559    0.4130    1.1214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2828   -0.3243    2.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554    0.9618    0.4031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8594    2.1059   -0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793    1.3914    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -1.0770    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171   -1.2361    1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    0.3310    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487    0.4088   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713   -1.5202   -1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345    0.8575   -1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7587   -1.4466    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0866    0.6124    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    1.2636    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -1.2536    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425    1.3274    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0509    2.2770   -0.9155 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
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  6
  9 22  1  0
 10 23  1  0
 11 24  1  1
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END


  Mrv1652309042000222D          

 16 16  0  0  1  0            999 V2000
   -1.8588    1.2102    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330    1.2102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6845    1.2162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    0.3904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708    2.0359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116    0.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -0.0030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1472   -0.8198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8498    0.4144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8648   -1.2281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5555   -1.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705    0.0120    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
    1.5764   -0.8107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8708   -2.0509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2791    0.4294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2942   -1.2191    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  2  0  0  0  0
  2  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  6  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  1  0  0  0
 12 15  1  4  0  0  0
 13 16  1  6  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029643

> <DATABASE_NAME>
MIME

> <SMILES>
OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O

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

> <INCHI_KEY>
NBSCHQHZLSJFNQ-GASJEMHNSA-N

> <FORMULA>
C6H13O9P

> <MOLECULAR_WEIGHT>
260.1358

> <EXACT_MASS>
260.029718526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
21.0042642444784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-2.06

> <JCHEM_LOGP>
-3.056105249333333

> <ALOGPS_LOGS>
-0.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.248752256962443

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.222936327751123

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64935696086094

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
46.796299999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glucose 6-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001401
     RDKit          3D
Glucose 6-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.7621   -0.8900   -1.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -0.5530   -0.1389 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.5887    1.1337   -0.0092 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -1.1940    1.3564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -1.2043   -0.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3219   -0.5737    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -0.0543   -0.4876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6994   -1.1139   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0091   -0.7023   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0752    0.3912   -1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382   -0.4421    0.2649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9015    0.1105    0.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7559    0.4130    1.1214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2828   -0.3243    2.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554    0.9618    0.4031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8594    2.1059   -0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793    1.3914    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -1.0770    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171   -1.2361    1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    0.3310    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487    0.4088   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713   -1.5202   -1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345    0.8575   -1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7587   -1.4466    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0866    0.6124    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    1.2636    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -1.2536    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425    1.3274    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0509    2.2770   -0.9155 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
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  6
  9 22  1  0
 10 23  1  0
 11 24  1  1
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  P   UNK     0      -3.470   2.259   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0      -1.928   2.259   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -5.011   2.270   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.492   0.729   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.492   3.800   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.328   0.852   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.258  -0.006   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.275  -1.530   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.586   0.774   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.614  -2.292   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.037  -2.321   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.932   0.022   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.943  -1.513   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.625  -3.828   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.254   0.802   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.283  -2.276   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7   10   11                                                  
CONECT    9    7   12                                                       
CONECT   10    8   13   14                                                  
CONECT   11    8                                                            
CONECT   12    9   15   13                                                  
CONECT   13   10   16   12                                                  
CONECT   14   10                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001401
HETATM    1  O1  UNL     1       4.762  -0.890  -1.231  1.00  0.00           O  
HETATM    2  P1  UNL     1       3.766  -0.553  -0.139  1.00  0.00           P  
HETATM    3  O2  UNL     1       3.589   1.134  -0.009  1.00  0.00           O  
HETATM    4  O3  UNL     1       4.245  -1.194   1.356  1.00  0.00           O  
HETATM    5  O4  UNL     1       2.244  -1.204  -0.529  1.00  0.00           O  
HETATM    6  C1  UNL     1       1.322  -0.574   0.292  1.00  0.00           C  
HETATM    7  C2  UNL     1       0.118  -0.054  -0.488  1.00  0.00           C  
HETATM    8  O5  UNL     1      -0.699  -1.114  -0.830  1.00  0.00           O  
HETATM    9  C3  UNL     1      -2.009  -0.702  -1.086  1.00  0.00           C  
HETATM   10  O6  UNL     1      -2.075   0.391  -1.932  1.00  0.00           O  
HETATM   11  C4  UNL     1      -2.638  -0.442   0.265  1.00  0.00           C  
HETATM   12  O7  UNL     1      -3.901   0.110   0.141  1.00  0.00           O  
HETATM   13  C5  UNL     1      -1.756   0.413   1.121  1.00  0.00           C  
HETATM   14  O8  UNL     1      -1.283  -0.324   2.210  1.00  0.00           O  
HETATM   15  C6  UNL     1      -0.555   0.962   0.403  1.00  0.00           C  
HETATM   16  O9  UNL     1      -0.859   2.106  -0.352  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.579   1.391   0.948  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.227  -1.077   1.481  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.917  -1.236   1.083  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.751   0.331   0.793  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.449   0.409  -1.452  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.571  -1.520  -1.563  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.934   0.857  -1.760  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.759  -1.447   0.744  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.087   0.612   0.968  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.319   1.264   1.537  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.615  -1.254   2.215  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.142   1.327   1.199  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.051   2.277  -0.916  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   19   20
CONECT    7    8   15   21
CONECT    8    9
CONECT    9   10   11   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

HMDB0001401
     RDKit          3D
Glucose 6-phosphate
 29 29  0  0  0  0  0  0  0  0999 V2000
    4.7621   -0.8900   -1.2314 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7664   -0.5530   -0.1389 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.5887    1.1337   -0.0092 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2449   -1.1940    1.3564 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2442   -1.2043   -0.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3219   -0.5737    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -0.0543   -0.4876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6994   -1.1139   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0091   -0.7023   -1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0752    0.3912   -1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382   -0.4421    0.2649 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9015    0.1105    0.1409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7559    0.4130    1.1214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2828   -0.3243    2.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554    0.9618    0.4031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8594    2.1059   -0.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5793    1.3914    0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273   -1.0770    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9171   -1.2361    1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    0.3310    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4487    0.4088   -1.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713   -1.5202   -1.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9345    0.8575   -1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7587   -1.4466    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0866    0.6124    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3191    1.2636    1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6149   -1.2536    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425    1.3274    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0509    2.2770   -0.9155 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
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15  7  1  0
  3 17  1  0
  4 18  1  0
  6 19  1  0
  6 20  1  0
  7 21  1  6
  9 22  1  0
 10 23  1  0
 11 24  1  1
 12 25  1  0
 13 26  1  1
 14 27  1  0
 15 28  1  1
 16 29  1  0
M  END

Synonyms

Value	Source
6-O-Phosphono-D-glucopyranose	ChEBI
D-Glucose 6-phosphate	ChEBI
GLC6p	ChEBI
Robison ester	ChEBI
D-Glucose 6-phosphoric acid	Generator
Glucose 6-phosphoric acid	Generator
a-D-Glucose 6- phosphate	HMDB
alpha-D-Glucose 6- phosphate	HMDB
alpha-D-Glucose 6-phosphate	HMDB
alpha-D-Hexose 6-phosphate	HMDB
D(+)-Glucopyranose 6-phosphate	HMDB
D-Glucose-6-dihydrogen phosphate	HMDB
D-Hexose 6-phosphate	HMDB
Glucose-6-phosphate	HMDB
Glucose 6-phosphate	KEGG
D-Glucopyranose 6-phosphoric acid	Generator

Molecular Formula

C₆H₁₃O₉P

Average Mass

260.1358

Monoisotopic Mass

260.029718526

IUPAC Name

{[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid

Traditional Name

glucose 6-phosphate

CAS Registry Number

56-73-5

SMILES

OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

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

InChI Key

NBSCHQHZLSJFNQ-GASJEMHNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexose phosphates

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-hexopyranose 6-phosphate (CHEBI:4170 )
D-glucose 6-phosphate (CHEBI:4170 )

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Property	Value	Source
Water Solubility	31.4 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.1	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	-3.6	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	21 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

Endoplasmic reticulum

Biospecimen Locations

Adipose Tissue
Adrenal Gland
Blood
Cellular Cytoplasm
Feces
Fibroblasts
Kidney
Liver
Placenta
Saliva
Skeletal Muscle
Urine

Tissue Locations

Adipose Tissue
Adrenal Gland
Fibroblasts
Kidney
Liver
Placenta
Skeletal Muscle

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191880	Glucokinase	Enzyme	P35557	Homo sapiens
MMDBp0191882	Hexokinase-3	Enzyme	P52790	Homo sapiens
MMDBp0191883	Hexokinase-2	Enzyme	P52789	Homo sapiens
MMDBp0191885	Hexokinase-1	Enzyme	P19367	Homo sapiens
MMDBp0191997	Glucose-6-phosphate 1-dehydrogenase	Enzyme	P11413	Homo sapiens
MMDBp0191998	GDH/6PGL endoplasmic bifunctional protein	Unknown	O95479	Homo sapiens
MMDBp0192036	ADP-dependent glucokinase	Unknown	Q9BRR6	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
MMDBp0192043	Glucose-6-phosphatase	Enzyme	P35575	Homo sapiens
MMDBp0192426	Glucose-6-phosphate isomerase	Enzyme	P06744	Homo sapiens
MMDBp0191639	Phosphoglucomutase-1	Enzyme	P36871	Escherichia coli
MMDBp0193314	Glucose-6-phosphate translocase	Enzyme	O43826	Homo sapiens
MMDBp0193724	Glucokinase regulatory protein	Enzyme	Q14397	Homo sapiens
MMDBp0193931	Phosphoglucomutase-2	Unknown	Q96G03	Homo sapiens
MMDBp0193991	Glucose-6-phosphatase 3	Enzyme	Q9BUM1	Homo sapiens
MMDBp0193992	Glucose-6-phosphatase 2	Enzyme	Q9NQR9	Homo sapiens
MMDBp0194020	Inositol-3-phosphate synthase 1	Unknown	Q9NPH2	Homo sapiens
MMDBp0196842	Putative hexokinase HKDC1	Unknown	Q2TB90

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018466	Glucose 6-phosphate	Glucose 1-phosphate	Phosphoglucomutase-1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0018597	Glucose 6-phosphate	Glucose 1-phosphate	Phosphoglucomutase-1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0018600	Glucose 6-phosphate	Uridine 5'-diphosphate	Trehalose-6-phosphate synthase	Synthesis	PathBank	31602464
MMDBr0018631	Glucose 6-phosphate	Glucose 1-phosphate	Phosphoglucomutase-1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0019337	Glucose 6-phosphate	Uridine 5'-diphosphate	Trehalose-6-phosphate synthase	Synthesis	PathBank	31602464
MMDBr0019361	beta-D-Glucopyranuronic acid	Glucose 6-phosphate	Glucokinase	Phosphorylation	PathBank	31602464
MMDBr0019455	D-Glucose	Glucose 6-phosphate	Putative glucokinase-2	Phosphorylation	PathBank	31602464
MMDBr0019456	alpha-D-Glucose	Glucose 6-phosphate	Putative glucokinase-2	Phosphorylation	PathBank	31602464
MMDBr0019459	Fructose 6-phosphate	Glucose 6-phosphate	Glucose-6-phosphate isomerase	Isomerization	PathBank	31602464
MMDBr0019479	alpha-D-Glucose	Glucose 6-phosphate	Putative glucokinase-2	Phosphorylation	PathBank	31602464
MMDBr0019480	Glucose 6-phosphate	beta-D-Fructofuranose 6-phosphate	Glucose-6-phosphate isomerase	Isomerization	PathBank	31602464
MMDBr0019492	Glucose 1-phosphate	Glucose 6-phosphate	Phosphoglucomutase 1	Intramolecular transfer of functional group	PathBank	31602464
MMDBr0019882	beta-D-Fructose 6-phosphate	Glucose 6-phosphate	Glucose-6-phosphate isomerase	Isomerization	PathBank	31602464
MMDBr0019883	alpha-D-Glucose	Glucose 6-phosphate	Putative glucokinase-2	Phosphorylation	PathBank	31602464
MMDBr0019896	Sucrose-6-phosphate	D-Fructose	Invertase		PathBank	31602464
MMDBr0019899	Glucose 6-phosphate	Uridine 5'-diphosphate	Trehalose-phosphatase	Dephosphorylation	PathBank	31602464
MMDBr0020006	Glucose 6-phosphate	1D-myo-inositol 3-phosphate	Unknown Protein		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	Association	Human Saliva	HMDB	23857558
Frontotemporal dementia	Association	Human Saliva	HMDB	23857558
Eosinophilic esophagitis	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	11	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	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	367	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	212	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	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	15	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	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	114	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	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	28	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	1	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	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Saliva	Detected and Quantified	4.06	0.96			uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Saliva	Detected and Quantified	5.51	3.94			uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Saliva	Detected and Quantified	7.79	8.06			uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Cellular cytoplasm	Detected and Quantified	38.0		26.0	50.0	uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Saliva	Detected and Quantified	6.88	3.72			uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Urine	Detected and Quantified	44.163				umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	29.1	6.8			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	4.52	8.7			uM	Newborn (0-30 days old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	1.60	1.19			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	1.73	1.28			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	2.23	5.59			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	2.42	1.55			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Adipose tissue	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001401

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

D-glucose-6-phosphate

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

4170

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Benkoel L, Chamlian A, Barrat E, Laffargue P: The use of ferricyanide for the electron microscopic demonstration of dehydrogenases in human steroidogenic cells. J Histochem Cytochem. 1976 Nov;24(11):1194-203. doi: 10.1177/24.11.1002973. [PubMed:1002973 ]
Vaag A, Damsbo P, Hother-Nielsen O, Beck-Nielsen H: Hyperglycaemia compensates for the defects in insulin-mediated glucose metabolism and in the activation of glycogen synthase in the skeletal muscle of patients with type 2 (non-insulin-dependent) diabetes mellitus. Diabetologia. 1992 Jan;35(1):80-8. doi: 10.1007/BF00400856. [PubMed:1541385 ]
Schalin-Jantti C, Harkonen M, Groop LC: Impaired activation of glycogen synthase in people at increased risk for developing NIDDM. Diabetes. 1992 May;41(5):598-604. doi: 10.2337/diab.41.5.598. [PubMed:1568529 ]
Boden G, Jadali F, White J, Liang Y, Mozzoli M, Chen X, Coleman E, Smith C: Effects of fat on insulin-stimulated carbohydrate metabolism in normal men. J Clin Invest. 1991 Sep;88(3):960-6. doi: 10.1172/JCI115399. [PubMed:1885781 ]
Cigolini M, Bonora E, Querena M, Moghetti P, Cacciatori V, Zancanaro C, Benati D, Muggeo M: Differences in glucose metabolic enzyme activities in human adipose tissue from abdominal and gluteal regions. Metabolism. 1988 Sep;37(9):820-3. doi: 10.1016/0026-0495(88)90114-x. [PubMed:3419322 ]
Boden G, Chen X, Ruiz J, White JV, Rossetti L: Mechanisms of fatty acid-induced inhibition of glucose uptake. J Clin Invest. 1994 Jun;93(6):2438-46. doi: 10.1172/JCI117252. [PubMed:8200979 ]
Lehto M, Xiang K, Stoffel M, Espinosa R 3rd, Groop LC, Le Beau MM, Bell GI: Human hexokinase II: localization of the polymorphic gene to chromosome 2. Diabetologia. 1993 Dec;36(12):1299-302. doi: 10.1007/BF00400809. [PubMed:8307259 ]
Chang PY, Jensen J, Printz RL, Granner DK, Ivy JL, Moller DE: Overexpression of hexokinase II in transgenic mice. Evidence that increased phosphorylation augments muscle glucose uptake. J Biol Chem. 1996 Jun 21;271(25):14834-9. [PubMed:8662926 ]
Vestergaard H, Bjorbaek C, Hansen T, Larsen FS, Granner DK, Pedersen O: Impaired activity and gene expression of hexokinase II in muscle from non-insulin-dependent diabetes mellitus patients. J Clin Invest. 1995 Dec;96(6):2639-45. doi: 10.1172/JCI118329. [PubMed:8675629 ]
Roussel R, Carlier PG, Wary C, Velho G, Bloch G: Evidence for 100% 13C NMR visibility of glucose in human skeletal muscle. Magn Reson Med. 1997 Jun;37(6):821-4. doi: 10.1002/mrm.1910370604. [PubMed:9178231 ]
Villar-Palasi C, Guinovart JJ: The role of glucose 6-phosphate in the control of glycogen synthase. FASEB J. 1997 Jun;11(7):544-58. [PubMed:9212078 ]
Foster JD, Pederson BA, Nordlie RC: Glucose-6-phosphatase structure, regulation, and function: an update. Proc Soc Exp Biol Med. 1997 Sep;215(4):314-32. doi: 10.3181/00379727-215-44142. [PubMed:9270716 ]
Petersen KF, Hendler R, Price T, Perseghin G, Rothman DL, Held N, Amatruda JM, Shulman GI: 13C/31P NMR studies on the mechanism of insulin resistance in obesity. Diabetes. 1998 Mar;47(3):381-6. doi: 10.2337/diabetes.47.3.381. [PubMed:9519743 ]
Cline GW, Petersen KF, Krssak M, Shen J, Hundal RS, Trajanoski Z, Inzucchi S, Dresner A, Rothman DL, Shulman GI: Impaired glucose transport as a cause of decreased insulin-stimulated muscle glycogen synthesis in type 2 diabetes. N Engl J Med. 1999 Jul 22;341(4):240-6. doi: 10.1056/NEJM199907223410404. [PubMed:10413736 ]
Price TB, Laurent D, Petersen KF: 13C/31P NMR studies on the role of glucose transport/phosphorylation in human glycogen supercompensation. Int J Sports Med. 2003 May;24(4):238-44. doi: 10.1055/s-2003-39501. [PubMed:12784164 ]
Roden M: How free fatty acids inhibit glucose utilization in human skeletal muscle. News Physiol Sci. 2004 Jun;19:92-6. doi: 10.1152/nips.01459.2003. [PubMed:15143200 ]
Turvey EA, Heigenhauser GJ, Parolin M, Peters SJ: Elevated n-3 fatty acids in a high-fat diet attenuate the increase in PDH kinase activity but not PDH activity in human skeletal muscle. J Appl Physiol (1985). 2005 Jan;98(1):350-5. doi: 10.1152/japplphysiol.00604.2004. [PubMed:15591305 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Brehm A, Krssak M, Schmid AI, Nowotny P, Waldhausl W, Roden M: Increased lipid availability impairs insulin-stimulated ATP synthesis in human skeletal muscle. Diabetes. 2006 Jan;55(1):136-40. [PubMed:16380486 ]
Fortpied J, Maliekal P, Vertommen D, Van Schaftingen E: Magnesium-dependent phosphatase-1 is a protein-fructosamine-6-phosphatase potentially involved in glycation repair. J Biol Chem. 2006 Jul 7;281(27):18378-85. doi: 10.1074/jbc.M513208200. Epub 2006 May 1. [PubMed:16670083 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Glucose 6-phosphate (MMDBc0029643)

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