Showing metabocard for beta-D-Fructofuranose 6-phosphate (MMDBc0047844)

Microbial
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 15:45:32 UTC
Update Date2025-10-07 16:08:05 UTC
Metabolite IDMMDBc0047844
Metabolite Identification
Common Namebeta-D-Fructofuranose 6-phosphate
Descriptionbeta-D-Fructofuranose 6-phosphate is a carbohydrate metabolite belonging to the class of phosphorylated sugars. Its chemical structure features a fructofuranose ring with a phosphate group at the 6-position, which plays a crucial role in various metabolic pathways. This compound is an intermediate in the fructose metabolism pathway, where it is involved in the conversion of fructose to glucose-6-phosphate, linking it to glycolysis and gluconeogenesis. Additionally, beta-D-Fructofuranose 6-phosphate can participate in the synthesis of nucleotides and nucleic acids, highlighting its importance in cellular energy metabolism and biosynthetic processes. The preparation of its carbocyclic analog has been documented, showcasing the compound's relevance in synthetic organic chemistry (PMID:2073635 ). Understanding the chemical properties and biological roles of beta-D-Fructofuranose 6-phosphate enhances our knowledge of carbohydrate metabolism and its implications in health and disease.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fae00e2ab70>

      
  Mrv1652303082008122D          

 16 16  0  0  0  0            999 V2000
    0.3278    0.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395    0.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    0.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242    0.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374   -0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7800    0.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -0.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757   -0.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -1.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2253   -1.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    0.1424    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1352   -0.4096    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.9495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506   -0.6646    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  5  9  1  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  1  0  0  0  0
  9 10  1  0  0  0  0
  7 13  1  0  0  0  0
 13 15  2  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
M  CHG  2  14  -1  16  -1
M  END
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3D MOL for #<Metabolite:0x00007fae00e2ab70>

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3D SDF for #<Metabolite:0x00007fae00e2ab70>
      
  Mrv1652303082008122D          

 16 16  0  0  0  0            999 V2000
    0.3278    0.6697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3395    0.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7404   -0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9953    0.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242    0.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374   -0.1124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7800    0.4395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5788   -0.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757   -0.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5696   -1.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2253   -1.2674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    0.1424    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1352   -0.4096    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.6937    0.9495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506   -0.6646    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  5  9  1  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  1  0  0  0  0
  9 10  1  0  0  0  0
  7 13  1  0  0  0  0
 13 15  2  0  0  0  0
 13 14  1  0  0  0  0
 13 16  1  0  0  0  0
M  CHG  2  14  -1  16  -1
M  END
> <DATABASE_ID>
MMDBc0047844

> <DATABASE_NAME>
MIME

> <SMILES>
OCC1(O)OC(COP([O-])([O-])=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/p-2

> <INCHI_KEY>
BGWGXPAPYGQALX-UHFFFAOYSA-L

> <FORMULA>
C6H11O9P

> <MOLECULAR_WEIGHT>
258.12

> <EXACT_MASS>
258.015166092

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.445679907528756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl phosphate

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-2.881565349333333

> <ALOGPS_LOGS>
-0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.247455552280461

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.221675286190254

> <JCHEM_PKA_STRONGEST_BASIC>
-3.450967575782875

> <JCHEM_POLAR_SURFACE_AREA>
162.57000000000002

> <JCHEM_REFRACTIVITY>
44.9903

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fae00e2ab70>
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PDB for #<Metabolite:0x00007fae00e2ab70>
HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  O   UNK     0       0.612   1.250   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.634   0.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.158  -1.120   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.382  -1.120   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.858   0.345   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.099   0.820   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.243  -0.210   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.323   0.820   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.947  -0.744   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.435  -0.346   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.063  -2.366   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.287  -2.366   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      -4.708   0.266   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      -5.852  -0.765   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0      -5.028   1.772   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.388  -1.241   0.000  0.00  0.00           O-1
CONECT    1    2    5                                                       
CONECT    2    3    6    1                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    9    1    8                                             
CONECT    6    2    7                                                       
CONECT    7    6   13                                                       
CONECT    8    5                                                            
CONECT    9    5   10                                                       
CONECT   10    9                                                            
CONECT   11    3                                                            
CONECT   12    4                                                            
CONECT   13    7   15   14   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for #<Metabolite:0x00007fae00e2ab70>
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SMILES for #<Metabolite:0x00007fae00e2ab70>
OCC1(O)OC(COP([O-])([O-])=O)C(O)C1O
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INCHI for #<Metabolite:0x00007fae00e2ab70>
InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/p-2
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Synonyms
ValueSource
Β-D-fructofuranose 6-phosphoric acidGenerator
Molecular FormulaC6H11O9P
Average Mass258.12
Monoisotopic Mass258.015166092
IUPAC Name[3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl phosphate
Traditional Name[3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl phosphate
CAS Registry NumberNot Available
SMILES
OCC1(O)OC(COP([O-])([O-])=O)C(O)C1O
InChI Identifier
InChI=1S/C6H13O9P/c7-2-6(10)5(9)4(8)3(15-6)1-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/p-2
InChI KeyBGWGXPAPYGQALX-UHFFFAOYSA-L