MiMeDB: Showing metabocard for alpha-D-Glucose 1,6-bisphosphate (MMDBc0029719)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:38:53 UTC

Update Date

2024-04-30 19:41:10 UTC

Metabolite ID

MMDBc0029719

Metabolite Identification

Common Name

alpha-D-Glucose 1,6-bisphosphate

Description

Alpha-D-glucose 1,6-bisphosphate is considered to be a major regulator of carbohydrate metabolism. Glucose 1,6-diphosphate (G 1,6-P2) have been recognized as a regulatory signal implicated in the control of metabolism, oxygen affinity of red cells and other cellular functions. G 1,6-P2 is a potent allosteric activator of phosphofructokinase.

Structure

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

HMDB0003514
     RDKit          3D
alpha-D-Glucose 1,6-bisphosphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.5028    0.6581    0.9082 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3237    1.0427    0.0316 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.9091    2.6647    0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7538    0.7867   -1.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767    0.0809    0.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8422    0.8749    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109    0.0605    0.5157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5316    0.7984    0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718    0.1115    0.0702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7166    0.7070    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8601    1.4167   -0.2292 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5489    1.1773   -1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    3.0969    0.0235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3699    0.7437    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6806   -1.3434    0.3827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1213   -1.5798    1.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -2.0658    0.0924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5817   -3.1288   -0.8052 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692   -1.0755   -0.4936 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8215   -1.6248   -0.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6029    2.8076    1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.1427   -1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    1.2653   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    1.7081    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6503   -0.3396    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    0.2827   -1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307    3.5458   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3197   -0.2318    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734   -1.8200   -0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757   -2.4980    1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -2.4535    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -2.9040   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.6487   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458   -1.9733   -1.6147 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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
  9 26  1  6
 13 27  1  0
 14 28  1  0
 15 29  1  6
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  1  0
M  END


  Mrv1652309042000292D          

 20 20  0  0  0  0            999 V2000
    0.5582    1.0063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1562    1.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5582    0.1812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2727   -0.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8707    0.1812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5852   -0.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1562   -0.2313    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1562   -1.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8707    1.0063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5852    1.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    1.0063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    1.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    0.1813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    1.0063    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497    1.0063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    1.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    2.2437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    0.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0977    1.4188    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.9227    1.4188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0  0  0  0
  2  1  1  0  0  0  0
  9  5  1  0  0  0  0
  5  7  1  0  0  0  0
  7  3  1  0  0  0  0
  3  1  1  0  0  0  0
  1 16  1  6  0  0  0
  3  4  1  6  0  0  0
  5  6  1  6  0  0  0
  7  8  1  1  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 14  1  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 19  1  0  0  0  0
 19 17  2  0  0  0  0
 19 18  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029719

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1

> <INCHI_KEY>
RWHOZGRAXYWRNX-VFUOTHLCSA-N

> <FORMULA>
C6H14O12P2

> <MOLECULAR_WEIGHT>
340.1157

> <EXACT_MASS>
339.996048936

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.959614359562895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-3.1796712806666663

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.4915079093370291

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8867658416836726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649397555635149

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
57.669200000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.60e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003514
     RDKit          3D
alpha-D-Glucose 1,6-bisphosphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.5028    0.6581    0.9082 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3237    1.0427    0.0316 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.9091    2.6647    0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7538    0.7867   -1.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767    0.0809    0.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8422    0.8749    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109    0.0605    0.5157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5316    0.7984    0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718    0.1115    0.0702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7166    0.7070    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8601    1.4167   -0.2292 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5489    1.1773   -1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    3.0969    0.0235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3699    0.7437    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6806   -1.3434    0.3827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1213   -1.5798    1.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -2.0658    0.0924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5817   -3.1288   -0.8052 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692   -1.0755   -0.4936 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8215   -1.6248   -0.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6029    2.8076    1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.1427   -1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    1.2653   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    1.7081    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6503   -0.3396    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    0.2827   -1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307    3.5458   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3197   -0.2318    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734   -1.8200   -0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757   -2.4980    1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -2.4535    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -2.9040   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.6487   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458   -1.9733   -1.6147 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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
  9 26  1  6
 13 27  1  0
 14 28  1  0
 15 29  1  6
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  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  C   UNK     0       1.042   1.878   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.292   2.648   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.042   0.338   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.376  -0.432   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.625   0.338   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.959  -0.432   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.292  -0.432   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.292  -1.972   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.625   1.878   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.959   2.648   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.293   1.878   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.833   3.418   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.833   0.338   0.000  0.00  0.00           O+0
HETATM   14  P   UNK     0      -5.833   1.878   0.000  0.00  0.00           P+0
HETATM   15  O   UNK     0      -7.373   1.878   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.376   2.648   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.916   4.188   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.916   1.108   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0       3.916   2.648   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0       5.456   2.648   0.000  0.00  0.00           O+0
CONECT    1    2    3   16                                                  
CONECT    2    9    1                                                       
CONECT    3    7    1    4                                                  
CONECT    4    3                                                            
CONECT    5    9    7    6                                                  
CONECT    6    5                                                            
CONECT    7    5    3    8                                                  
CONECT    8    7                                                            
CONECT    9    2    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   14                                                       
CONECT   12   14                                                            
CONECT   13   14                                                            
CONECT   14   11   12   13   15                                             
CONECT   15   14                                                            
CONECT   16    1   19                                                       
CONECT   17   19                                                            
CONECT   18   19                                                            
CONECT   19   16   17   18   20                                             
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0003514
HETATM    1  O1  UNL     1       5.503   0.658   0.908  1.00  0.00           O  
HETATM    2  P1  UNL     1       4.324   1.043   0.032  1.00  0.00           P  
HETATM    3  O2  UNL     1       3.909   2.665   0.250  1.00  0.00           O  
HETATM    4  O3  UNL     1       4.754   0.787  -1.602  1.00  0.00           O  
HETATM    5  O4  UNL     1       2.977   0.081   0.377  1.00  0.00           O  
HETATM    6  C1  UNL     1       1.842   0.875   0.219  1.00  0.00           C  
HETATM    7  C2  UNL     1       0.611   0.061   0.516  1.00  0.00           C  
HETATM    8  O5  UNL     1      -0.532   0.798   0.374  1.00  0.00           O  
HETATM    9  C3  UNL     1      -1.672   0.111   0.070  1.00  0.00           C  
HETATM   10  O6  UNL     1      -2.717   0.707   0.783  1.00  0.00           O  
HETATM   11  P2  UNL     1      -3.860   1.417  -0.229  1.00  0.00           P  
HETATM   12  O7  UNL     1      -3.549   1.177  -1.690  1.00  0.00           O  
HETATM   13  O8  UNL     1      -3.942   3.097   0.024  1.00  0.00           O  
HETATM   14  O9  UNL     1      -5.370   0.744   0.151  1.00  0.00           O  
HETATM   15  C4  UNL     1      -1.681  -1.343   0.383  1.00  0.00           C  
HETATM   16  O10 UNL     1      -2.121  -1.580   1.706  1.00  0.00           O  
HETATM   17  C5  UNL     1      -0.408  -2.066   0.092  1.00  0.00           C  
HETATM   18  O11 UNL     1      -0.582  -3.129  -0.805  1.00  0.00           O  
HETATM   19  C6  UNL     1       0.569  -1.075  -0.494  1.00  0.00           C  
HETATM   20  O12 UNL     1       1.822  -1.625  -0.711  1.00  0.00           O  
HETATM   21  H1  UNL     1       3.603   2.808   1.164  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.069  -0.143  -1.711  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.790   1.265  -0.814  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.884   1.708   0.959  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.650  -0.340   1.550  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.902   0.283  -1.004  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.131   3.546  -0.307  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.320  -0.232   0.071  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.473  -1.820  -0.256  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.976  -2.498   1.979  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.017  -2.454   1.048  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.152  -2.904  -1.662  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.117  -0.649  -1.421  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.946  -1.973  -1.615  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4    5
CONECT    3   21
CONECT    4   22
CONECT    5    6
CONECT    6    7   23   24
CONECT    7    8   19   25
CONECT    8    9
CONECT    9   10   15   26
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   27
CONECT   14   28
CONECT   15   16   17   29
CONECT   16   30
CONECT   17   18   19   31
CONECT   18   32
CONECT   19   20   33
CONECT   20   34
END

HMDB0003514
     RDKit          3D
alpha-D-Glucose 1,6-bisphosphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    5.5028    0.6581    0.9082 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3237    1.0427    0.0316 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.9091    2.6647    0.2503 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7538    0.7867   -1.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9767    0.0809    0.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8422    0.8749    0.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109    0.0605    0.5157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5316    0.7984    0.3738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6718    0.1115    0.0702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7166    0.7070    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8601    1.4167   -0.2292 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.5489    1.1773   -1.6903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9421    3.0969    0.0235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3699    0.7437    0.1509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6806   -1.3434    0.3827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1213   -1.5798    1.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083   -2.0658    0.0924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5817   -3.1288   -0.8052 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5692   -1.0755   -0.4936 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8215   -1.6248   -0.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6029    2.8076    1.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -0.1427   -1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7896    1.2653   -0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8845    1.7081    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6503   -0.3396    1.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9020    0.2827   -1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1307    3.5458   -0.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3197   -0.2318    0.0706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734   -1.8200   -0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757   -2.4980    1.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -2.4535    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -2.9040   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -0.6487   -1.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9458   -1.9733   -1.6147 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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  9 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  7  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  1
  9 26  1  6
 13 27  1  0
 14 28  1  0
 15 29  1  6
 16 30  1  0
 17 31  1  1
 18 32  1  0
 19 33  1  6
 20 34  1  0
M  END

Synonyms

Value	Source
alpha-D-Glucose 1,6-biphosphate	ChEBI
D-Glucose 1,6-biphosphate	ChEBI
D-Glucose 1,6-bisphosphate	Kegg
a-D-Glucose 1,6-biphosphate	Generator
a-D-Glucose 1,6-biphosphoric acid	Generator
alpha-D-Glucose 1,6-biphosphoric acid	Generator
Α-D-glucose 1,6-biphosphate	Generator
Α-D-glucose 1,6-biphosphoric acid	Generator
D-Glucose 1,6-biphosphoric acid	Generator
D-Glucose 1,6-bisphosphoric acid	Generator
a-D-Glucose 1,6-bisphosphate	Generator
a-D-Glucose 1,6-bisphosphoric acid	Generator
alpha-D-Glucose 1,6-bisphosphoric acid	Generator
Α-D-glucose 1,6-bisphosphate	Generator
Α-D-glucose 1,6-bisphosphoric acid	Generator
a-D-Glucose 1,6-bis(dihydrogen phosphate)	HMDB
a-D-Glucose 1,6-diphosphate	HMDB
alpha-D-1,6-Bis(dihydrogen phosphate) glucopyranose	HMDB
alpha-D-Glucose 1,6-bis(dihydrogen phosphate)	HMDB
alpha-D-Glucose 1,6-diphosphate	HMDB
alpha-delta-1,6-Bis(dihydrogen phosphate) glucopyranose	HMDB
alpha-delta-Glucose 1,6-bis(dihydrogen phosphate)	HMDB
alpha-delta-Glucose 1,6-bisphosphate	HMDB
alpha-delta-Glucose 1,6-diphosphate	HMDB
D-Glucose 1,6-diphosphate	HMDB
delta-Glucose 1,6-diphosphate	HMDB
Glucose 1,6-bisphosphate	HMDB
Glucose 1,6-diphosphate	HMDB
beta-D-Glucose 1,6-(bis)phosphate	HMDB
Glucose-1,6-diphosphate	HMDB
Glucose-1,6-bisphosphate	HMDB
alpha-Glucose 1,6-diphosphate	HMDB
Α-D-glucose 1,6-diphosphate	HMDB
Α-glucose 1,6-diphosphate	HMDB
alpha-D-Glucose 1,6-bisphosphate	HMDB

Molecular Formula

C₆H₁₄O₁₂P₂

Average Mass

340.1157

Monoisotopic Mass

339.996048936

IUPAC Name

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

Traditional Name

[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxyphosphonic acid

CAS Registry Number

10139-18-1

SMILES

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

InChI Identifier

InChI=1S/C6H14O12P2/c7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15/h2-9H,1H2,(H2,10,11,12)(H2,13,14,15)/t2-,3-,4+,5-,6-/m1/s1

InChI Key

RWHOZGRAXYWRNX-VFUOTHLCSA-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
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucose 1,6-bisphosphate (CHEBI:18148 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	16 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-3.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.89	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.67 m³·mol⁻¹	ChemAxon
Polarizability	24.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9422000000-7bfff1b0b2d51cca5dff	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0fr5-7922130000-d6ba2057c5f43a10b976	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002f-9182000000-23bca820b90a45f17acb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-00dl-0089000000-14b2732dbc26e1c46650	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-03di-0090000000-eff1032954c312ffe781	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-03di-0019000000-b6e1680b5b949ae7c8f6	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-03xr-0069000000-63772b51257cee2af15a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-014i-0092000000-65fab63b500e60a0ea01	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-014i-0190000000-bfbcf573cf5f756927f9	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, positive	splash10-01b9-0790000000-757dcf8e67df0907f65a	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, positive	splash10-00di-0920000000-18f7c04ce401fda68354	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-014i-0090000000-e9698a8c472de2ec65b3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-00fr-0930000000-7f0cb15d50e589a9640f	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-0002-0910000000-4a92067b100f48729122	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-0002-0390000000-c8d4b6af4a7e1dbc6766	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-004i-0069000000-b2d82f85ee47b9928a9c	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 23V, positive	splash10-004i-0091000000-e9e211cdeab0d7aab3ab	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-014i-0000900000-386775c642a8d4f6b7b3	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-014i-0004900000-249416017fe86caa0eb1	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-014i-0109200000-91fd1405fb3d3ce23e3d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-014i-0309000000-71838f11ad810bfe78ac	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-2169000000-7496db21481f5c6646f1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-8194000000-0ab11c338e7462b1784e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9710000000-04febc887536086e1a99	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-7319000000-8f0f5f6bb5550e944766	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-e67858a197b35311ba75	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-44fd1ff1d686ff20aa4f	2015-09-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0193156	Phosphomannomutase 2	Enzyme	O15305	Homo sapiens
MMDBp0193820	Cytochrome c oxidase subunit 5A, mitochondrial	Unknown	P20674	Homo sapiens
MMDBp0193931	Phosphoglucomutase-2	Unknown	Q96G03	Homo sapiens
MMDBp0195900	Glucose 1,6-bisphosphate synthase	Enzyme	Q6PCE3	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010644	Glyceric acid 1,3-biphosphate	3-Phospho-D-glycerate	Phosphoglucomutase 2-like 1	3-Phospho-D-Glyceroyl-Phosphate:Alpha-D-Glucose-1-Phosphate 6-Phosphotransferase	VMH; KEGG	30371894
MMDBr0010677	alpha-D-Glucose 1,6-bisphosphate	alpha-D-Glucose 1,6-bisphosphate	Not Available	HMR_9187	VMH	30371894
MMDBr0010850	Glyceric acid 1,3-biphosphate	3-Phospho-D-glycerate	Not Available	3 phospho D glyceroyl phosphate alpha D glucose 1 phosphate 6 phosphotransferase	VMH	30371894
MMDBr0010904	Glucose 1-phosphate	D-Glucose	Not Available	D Glucose 1 phosphate D glucose 1 phosphate 6 phosphotransferase	VMH	30371894
MMDBr0010943	Glyceric acid 1,3-biphosphate	3-Phospho-D-glycerate	Not Available	3 phospho D glyceroyl phosphate alpha D glucose 1 phosphate 6 phosphotransferase	VMH	30371894
MMDBr0019885	Glyceric acid 1,3-biphosphate	alpha-D-Glucose 1,6-bisphosphate	Phosphoribomutase		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	76	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Pig	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	203	Pig ; Human feces; Human ; Human stool; Human subgingival plaque; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	55	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Bacteroidetes	61	Human feces; Human appendix biopsy; Human ; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque; Human stool	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	4	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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 Blood	Detected and Quantified	98.0	17.0	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 Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0003514

DrugBank ID

DB02835

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023185

KNApSAcK ID

Not Available

Chemspider ID

74362

KEGG Compound ID

C01231

BioCyc ID

ALPHA-GLUCOSE-16-BISPHOSPHATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

82400

PDB ID

Not Available

ChEBI ID

18148

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Cadefau JA, Andres V, Carreras J, Vernet M, Grau JM, Urbano-Marquez A, Cusso R: Glucose 1,6-bisphosphate and fructose 2,6-bisphosphate in muscle from healthy humans and chronic alcoholic patients. Alcohol Alcohol. 1992 May;27(3):253-6. [PubMed:1449560 ]
Katz A, Sahlin K, Broberg S: Regulation of glucose utilization in human skeletal muscle during moderate dynamic exercise. Am J Physiol. 1991 Mar;260(3 Pt 1):E411-5. doi: 10.1152/ajpendo.1991.260.3.E411. [PubMed:2003594 ]
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 ]
Katz A: G-1,6-P2, glycolysis, and energy metabolism during circulatory occlusion in human skeletal muscle. Am J Physiol. 1988 Aug;255(2 Pt 1):C140-4. doi: 10.1152/ajpcell.1988.255.2.C140. [PubMed:3407759 ]
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Showing metabocard for alpha-D-Glucose 1,6-bisphosphate (MMDBc0029719)

MOL for #<Metabolite:0x00007fa4e1ddbb10>

3D MOL for #<Metabolite:0x00007fa4e1ddbb10>

3D SDF for #<Metabolite:0x00007fa4e1ddbb10>

3D-SDF for #<Metabolite:0x00007fa4e1ddbb10>

PDB for #<Metabolite:0x00007fa4e1ddbb10>

3D PDB for #<Metabolite:0x00007fa4e1ddbb10>

SMILES for #<Metabolite:0x00007fa4e1ddbb10>

INCHI for #<Metabolite:0x00007fa4e1ddbb10>

Structure for #<Metabolite:0x00007fa4e1ddbb10>

3D Structure for #<Metabolite:0x00007fa4e1ddbb10>