MiMeDB: Showing metabocard for D-Fructose 2,6-bisphosphate (MMDBc0032902)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:20:46 UTC

Update Date

2022-08-31 21:45:25 UTC

Metabolite ID

MMDBc0032902

Metabolite Identification

Common Name

D-Fructose 2,6-bisphosphate

Description

D-Fructose 2,6-bisphosphate, also known as phosphofructokinase activator, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. A D-fructofuranose 2,6-bisphosphate with a beta-configuration at the anomeric centre. D-Fructose 2,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. D-fructose 2,6-bisphosphate can be converted into fructose 6-phosphate; which is mediated by the enzyme 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1. In humans, D-fructose 2,6-bisphosphate is involved in the metabolic disorder called fructosuria.

Structure

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

HMDB0001047
     RDKit          3D
D-Fructose 2,6-bisphosphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.7742   -2.1374    1.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -0.6901    0.8552 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3255    0.0615    2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6570   -0.7019    0.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941    0.1007   -0.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7845   -0.5616    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    0.0699   -0.6699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4980   -0.6273   -0.4493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695    0.2079   -0.5142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5574   -0.1941   -1.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -0.1818   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163    0.2725    0.6575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591   -1.1773    1.1398 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0799   -2.3635    0.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4705   -1.4571    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -1.1034    2.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0613    1.6154   -0.7657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7804    2.5620   -0.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592    1.4747   -0.1976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2043    2.4206   -0.7602 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -0.3555    2.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6452   -0.1611   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028   -0.6171    1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -1.6057   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    0.1509   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -1.2161   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512    0.4582   -1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806   -0.5677   -2.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476   -2.3046    0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -0.1780    3.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884    1.8385   -1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303    3.3729    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.5246    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458    2.0713   -1.0871 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
  9 12  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
  9 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  6
 10 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  6
 18 32  1  0
 19 33  1  1
 20 34  1  0
M  END


  Mrv1652307232018072D          

 20 20  0  0  0  0            999 V2000
10001.8007 9999.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.5163 9999.8712    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10002.103310000.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.2318 9999.4585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.927210000.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.700610000.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.700610001.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2346 9998.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4489 9998.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.938110000.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.225410000.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.512810000.5365    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.924710001.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.798110000.1246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.100910001.2512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.323410000.6191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.990810000.1341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.7359 9999.3495    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9109 9999.3495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.656010000.1341    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  6  7  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17  1  1  1  0  0  0
 17  6  1  0  0  0  0
 18  8  1  1  0  0  0
 19  9  1  6  0  0  0
 20 10  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032902

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1

> <INCHI_KEY>
YXWOAJXNVLXPMU-ZXXMMSQZSA-N

> <FORMULA>
C6H14O12P2

> <MOLECULAR_WEIGHT>
340.1157

> <EXACT_MASS>
339.996048936

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.243417387291053

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.50

> <JCHEM_LOGP>
-3.0051313806666666

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.3703815262407373

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.6839676218192321

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4678657648404636

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
58.1066

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fructose-2,6-diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001047
     RDKit          3D
D-Fructose 2,6-bisphosphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.7742   -2.1374    1.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -0.6901    0.8552 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3255    0.0615    2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6570   -0.7019    0.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941    0.1007   -0.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7845   -0.5616    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    0.0699   -0.6699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4980   -0.6273   -0.4493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695    0.2079   -0.5142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5574   -0.1941   -1.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -0.1818   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163    0.2725    0.6575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591   -1.1773    1.1398 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0799   -2.3635    0.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4705   -1.4571    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -1.1034    2.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0613    1.6154   -0.7657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7804    2.5620   -0.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592    1.4747   -0.1976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2043    2.4206   -0.7602 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -0.3555    2.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6452   -0.1611   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028   -0.6171    1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -1.6057   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    0.1509   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -1.2161   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512    0.4582   -1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806   -0.5677   -2.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476   -2.3046    0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -0.1780    3.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884    1.8385   -1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303    3.3729    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.5246    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458    2.0713   -1.0871 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
  9 12  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
  9 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  6
 10 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  6
 18 32  1  0
 19 33  1  1
 20 34  1  0
M  END

HEADER    PROTEIN                                 23-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUL-20         0                                  
HETATM    1  O   UNK     0    8670.0288665.660   0.000  0.00  0.00           O+0
HETATM    2  P   UNK     0    8671.3648666.426   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0    8670.5938667.757   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8672.6998665.656   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.1318667.757   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8669.8418667.668   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8669.8418669.206   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8668.9718664.217   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8665.6388664.202   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8664.6848667.668   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8663.3548666.899   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0    8662.0248667.668   0.000  0.00  0.00           P+0
HETATM   13  O   UNK     0    8662.7938669.002   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8660.6908666.899   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8661.2558669.002   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8667.2708667.822   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8668.5168666.917   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.0408665.452   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.5008665.452   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0258666.917   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    7   17                                                       
CONECT    7    6                                                            
CONECT    8   18                                                            
CONECT    9   19                                                            
CONECT   10   11   20                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   17   20                                                       
CONECT   17   18   16    1    6                                             
CONECT   18   17   19    8                                                  
CONECT   19   18   20    9                                                  
CONECT   20   19   16   10                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0001047
HETATM    1  O1  UNL     1       3.774  -2.137   1.119  1.00  0.00           O  
HETATM    2  P1  UNL     1       4.165  -0.690   0.855  1.00  0.00           P  
HETATM    3  O2  UNL     1       4.326   0.062   2.370  1.00  0.00           O  
HETATM    4  O3  UNL     1       5.657  -0.702   0.078  1.00  0.00           O  
HETATM    5  O4  UNL     1       2.994   0.101  -0.064  1.00  0.00           O  
HETATM    6  C1  UNL     1       1.785  -0.562   0.116  1.00  0.00           C  
HETATM    7  C2  UNL     1       0.659   0.070  -0.670  1.00  0.00           C  
HETATM    8  O5  UNL     1      -0.498  -0.627  -0.449  1.00  0.00           O  
HETATM    9  C3  UNL     1      -1.569   0.208  -0.514  1.00  0.00           C  
HETATM   10  C4  UNL     1      -2.557  -0.194  -1.618  1.00  0.00           C  
HETATM   11  O6  UNL     1      -1.974  -0.182  -2.863  1.00  0.00           O  
HETATM   12  O7  UNL     1      -2.316   0.272   0.658  1.00  0.00           O  
HETATM   13  P2  UNL     1      -2.959  -1.177   1.140  1.00  0.00           P  
HETATM   14  O8  UNL     1      -2.080  -2.363   0.854  1.00  0.00           O  
HETATM   15  O9  UNL     1      -4.470  -1.457   0.429  1.00  0.00           O  
HETATM   16  O10 UNL     1      -3.228  -1.103   2.826  1.00  0.00           O  
HETATM   17  C5  UNL     1      -1.061   1.615  -0.766  1.00  0.00           C  
HETATM   18  O11 UNL     1      -1.780   2.562  -0.062  1.00  0.00           O  
HETATM   19  C6  UNL     1       0.359   1.475  -0.198  1.00  0.00           C  
HETATM   20  O12 UNL     1       1.204   2.421  -0.760  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.091  -0.355   2.832  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.645  -0.161  -0.732  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.503  -0.617   1.180  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.888  -1.606  -0.254  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.950   0.151  -1.741  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.916  -1.216  -1.319  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.451   0.458  -1.540  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.081  -0.568  -2.800  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.848  -2.305   0.772  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.358  -0.178   3.135  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.988   1.838  -1.839  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.230   3.373   0.012  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.319   1.525   0.901  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.046   2.071  -1.087  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   12   17
CONECT   10   11   26   27
CONECT   11   28
CONECT   12   13
CONECT   13   14   14   15   16
CONECT   15   29
CONECT   16   30
CONECT   17   18   19   31
CONECT   18   32
CONECT   19   20   33
CONECT   20   34
END

HMDB0001047
     RDKit          3D
D-Fructose 2,6-bisphosphate
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.7742   -2.1374    1.1187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -0.6901    0.8552 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.3255    0.0615    2.3701 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6570   -0.7019    0.0781 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941    0.1007   -0.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7845   -0.5616    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    0.0699   -0.6699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4980   -0.6273   -0.4493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695    0.2079   -0.5142 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5574   -0.1941   -1.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741   -0.1818   -2.8633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163    0.2725    0.6575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9591   -1.1773    1.1398 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.0799   -2.3635    0.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4705   -1.4571    0.4287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -1.1034    2.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0613    1.6154   -0.7657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7804    2.5620   -0.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3592    1.4747   -0.1976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2043    2.4206   -0.7602 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -0.3555    2.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6452   -0.1611   -0.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028   -0.6171    1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -1.6057   -0.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    0.1509   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -1.2161   -1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512    0.4582   -1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0806   -0.5677   -2.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476   -2.3046    0.7725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -0.1780    3.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884    1.8385   -1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303    3.3729    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3193    1.5246    0.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458    2.0713   -1.0871 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
  9 12  1  1
 12 13  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
  9 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  6
 10 26  1  0
 10 27  1  0
 11 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  6
 18 32  1  0
 19 33  1  1
 20 34  1  0
M  END

Synonyms

Value	Source
2,6-Di-O-phosphono-beta-D-fructofuranose	ChEBI
2,6-Di-O-phosphono-b-D-fructofuranose	Generator
2,6-Di-O-phosphono-β-D-fructofuranose	Generator
D-Fructose 2,6-bisphosphoric acid	Generator
b-D-Fructose 2,6-bisphosphate	HMDB
beta-D-Fructose 2,6-bisphosphate	HMDB
Fru 2,6-P2, fructose 2,6-diphosphate	HMDB
Fructose 2,6-bisphosphate	HMDB
Fructose 2,6-biphosphate	MeSH, HMDB
Fructose 2,6-diphosphate	MeSH, HMDB
Phosphofructokinase activation factor	MeSH, HMDB
Phosphofructokinase activator	MeSH, HMDB
Fructose-2,6-diphosphate	MeSH, HMDB
D-Fructose 2,6-diphosphate	HMDB
beta-D-Fructose 2,6-diphosphate	HMDB
β-D-Fructose 2,6-diphosphate	HMDB

Molecular Formula

C₆H₁₄O₁₂P₂

Average Mass

340.1157

Monoisotopic Mass

339.996048936

IUPAC Name

{[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid

Traditional Name

fructose-2,6-diphosphate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6+/m1/s1

InChI Key

YXWOAJXNVLXPMU-ZXXMMSQZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose 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

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
C-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Alkyl phosphate
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose 2,6-bisphosphate (CHEBI:28602 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	15.8 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-3	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	0.68	ChemAxon
pKa (Strongest Basic)	-3.5	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	6	ChemAxon
Refractivity	58.11 m³·mol⁻¹	ChemAxon
Polarizability	25.24 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01dj-0963000000-090736f476a618727455	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00tb-0972000000-e47c74a14376eaabd8c3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01dj-0963000000-090736f476a618727455	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00tb-0972000000-e47c74a14376eaabd8c3	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9512000000-82418e0e398490357c5e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-2190010000-53cf738181713979e181	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
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, negative	splash10-000i-0019000000-7b58b1d6169f22e732a8	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, negative	splash10-000m-2496000000-40ad2c4944ae5c0701f3	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, negative	splash10-0002-9830000000-a9cbb8a3dba391a8858b	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, negative	splash10-002b-9200000000-6dcaff4e5eee3799656f	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 50V, negative	splash10-004j-9100000000-9851b59e56acb7c5802c	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-3797000000-cb11e27ce8d0be902a39	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9132000000-b908246df46f54e31180	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dm-9600000000-19262e5981934144e1aa	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-7409000000-0240bd8771cde252759c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-8930f98e412f1b68e30b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-fb204edc71835bcbaaad	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0393000000-f7f716e45f745f0bec68	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1920000000-f0eccbb835449758a67c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-9410000000-f9f76bd919e86701aaff	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9008000000-d519306c146482d051d0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9001000000-2d0e9375a49babbe9d93	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-bc05f33d90e2bf18235c	2021-09-24	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)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192416	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3	Enzyme	Q16875	Homo sapiens
MMDBp0192418	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 4	Enzyme	Q16877	Homo sapiens
MMDBp0192419	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1	Enzyme	P16118	Homo sapiens
MMDBp0192424	6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2	Enzyme	O60825	Homo sapiens
MMDBp0196993	Fructose-2,6-bisphosphatase TIGAR	Unknown	Q9NQ88

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001208	D-Fructose 2,6-bisphosphate	Fructose 6-phosphate	fructose-1,6-bisphosphatase 1		VMH; KEGG	30371894
MMDBr0001918	Fructose 6-phosphate	D-Fructose 2,6-bisphosphate	Not Available		VMH; KEGG	30371894

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
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Bacteria	Proteobacteria	1	Human feces	Metabolic reconstruction

Exposure Sources

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

External Links

HMDB ID

HMDB0001047

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Fructose_2,6-bisphosphate

METLIN ID

5964

PubChem Compound

105021

PDB ID

Not Available

ChEBI ID

28602

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for D-Fructose 2,6-bisphosphate (MMDBc0032902)

MOL for #<Metabolite:0x00007fdb3433e408>

3D MOL for #<Metabolite:0x00007fdb3433e408>

3D SDF for #<Metabolite:0x00007fdb3433e408>

3D-SDF for #<Metabolite:0x00007fdb3433e408>

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3D PDB for #<Metabolite:0x00007fdb3433e408>

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Structure for #<Metabolite:0x00007fdb3433e408>

3D Structure for #<Metabolite:0x00007fdb3433e408>