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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:45:00 UTC

Update Date

2021-09-26 22:54:18 UTC

HMDB ID

HMDB0245694

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-O,6-O-Benzylidene-alpha-D-glucopyranose

Description

4,6-Benzylidene-D-glucose, also known as benzylidene glucopyranose, belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring. 4,6-Benzylidene-D-glucose has been detected, but not quantified in, figs (Ficus carica). This could make 4,6-benzylidene-D-glucose a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4,6-Benzylidene-D-glucose. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-o,6-o-benzylidene-alpha-d-glucopyranose is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-O,6-O-Benzylidene-alpha-D-glucopyranose is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0245694
     RDKit          3D
4-O,6-O-Benzylidene-alpha-D-glucopyranose
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.7454   -0.7145    0.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    0.1114    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.6495    0.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916    0.1031    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4817   -0.8738    1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019   -0.3409    1.6536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -0.1595    0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    0.0088    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6410   -0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5487   -0.4704   -1.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2789    0.3560   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5993    1.0097    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2436    0.8377    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    0.9810   -0.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    0.8878    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    0.3414   -1.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.9981   -1.4002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1355    0.5423   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029    1.8507   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725   -0.2640   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823    0.9336    0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.7934    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7720   -1.1872    2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -1.7546    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6738   -1.0855   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -1.2949   -1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1023   -0.9829   -1.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3496    0.4744   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1635    1.6595    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    1.3603    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    1.9353    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    0.9497   -2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -1.5669   -1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6664   -0.0888   -1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    2.3130   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  2  1  0
 15  4  1  0
 13  8  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END

  Mrv0541 02241220522D          

 19 21  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  4 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245694

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1OC2COC(OC2C(O)C1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O6/c14-9-10(15)12(16)18-8-6-17-13(19-11(8)9)7-4-2-1-3-5-7/h1-5,8-16H,6H2

> <INCHI_KEY>
FOLRUCXBTYDAQK-UHFFFAOYSA-N

> <FORMULA>
C13H16O6

> <MOLECULAR_WEIGHT>
268.2625

> <EXACT_MASS>
268.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.502515479423586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-6,7,8-triol

> <ALOGPS_LOGP>
-0.30

> <JCHEM_LOGP>
0.23254003366666665

> <ALOGPS_LOGS>
-0.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.89490397748919

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.305527916433396

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6855384552543775

> <JCHEM_POLAR_SURFACE_AREA>
88.38000000000001

> <JCHEM_REFRACTIVITY>
62.807000000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-6,7,8-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245694
     RDKit          3D
4-O,6-O-Benzylidene-alpha-D-glucopyranose
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.7454   -0.7145    0.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    0.1114    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.6495    0.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916    0.1031    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4817   -0.8738    1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019   -0.3409    1.6536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -0.1595    0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    0.0088    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6410   -0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5487   -0.4704   -1.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2789    0.3560   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5993    1.0097    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2436    0.8377    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    0.9810   -0.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    0.8878    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    0.3414   -1.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.9981   -1.4002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1355    0.5423   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029    1.8507   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725   -0.2640   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823    0.9336    0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.7934    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7720   -1.1872    2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -1.7546    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6738   -1.0855   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -1.2949   -1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1023   -0.9829   -1.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3496    0.4744   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1635    1.6595    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    1.3603    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    1.9353    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    0.9497   -2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -1.5669   -1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6664   -0.0888   -1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    2.3130   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  2  1  0
 15  4  1  0
 13  8  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10    4                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    1                                                       
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0245694
HETATM    1  O1  UNL     1       4.745  -0.714   0.135  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.613   0.111   0.250  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.632  -0.649   0.864  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.492   0.103   1.160  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.482  -0.874   1.724  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.802  -0.341   1.654  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.047  -0.160   0.272  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.498   0.009   0.078  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.190  -0.641  -0.924  1.00  0.00           C  
HETATM   10  C7  UNL     1      -4.549  -0.470  -1.089  1.00  0.00           C  
HETATM   11  C8  UNL     1      -5.279   0.356  -0.262  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.599   1.010   0.742  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.244   0.838   0.904  1.00  0.00           C  
HETATM   14  O4  UNL     1      -0.370   0.981  -0.101  1.00  0.00           O  
HETATM   15  C11 UNL     1       0.987   0.888   0.004  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.633   0.341  -1.270  1.00  0.00           C  
HETATM   17  O5  UNL     1       1.355  -0.998  -1.400  1.00  0.00           O  
HETATM   18  C13 UNL     1       3.136   0.542  -1.110  1.00  0.00           C  
HETATM   19  O6  UNL     1       3.503   1.851  -1.308  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.472  -0.264  -0.383  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.882   0.934   0.911  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.752   0.793   2.009  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.772  -1.187   2.728  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.488  -1.755   1.031  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.674  -1.085  -0.209  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.643  -1.295  -1.587  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.102  -0.983  -1.881  1.00  0.00           H  
HETATM   28  H9  UNL     1      -6.350   0.474  -0.412  1.00  0.00           H  
HETATM   29  H10 UNL     1      -5.164   1.660   1.395  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.708   1.360   1.704  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.389   1.935   0.099  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.290   0.950  -2.125  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.136  -1.567  -1.236  1.00  0.00           H  
HETATM   34  H15 UNL     1       3.666  -0.089  -1.876  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.794   2.313  -0.492  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3   18   21
CONECT    3    4
CONECT    4    5   15   22
CONECT    5    6   23   24
CONECT    6    7
CONECT    7    8   14   25
CONECT    8    9    9   13
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   30
CONECT   14   15
CONECT   15   16   31
CONECT   16   17   18   32
CONECT   17   33
CONECT   18   19   34
CONECT   19   35
END

HMDB0245694
     RDKit          3D
4-O,6-O-Benzylidene-alpha-D-glucopyranose
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.7454   -0.7145    0.1348 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6127    0.1114    0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -0.6495    0.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916    0.1031    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4817   -0.8738    1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019   -0.3409    1.6536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468   -0.1595    0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    0.0088    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.6410   -0.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5487   -0.4704   -1.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2789    0.3560   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5993    1.0097    0.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2436    0.8377    0.9041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3704    0.9810   -0.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    0.8878    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    0.3414   -1.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.9981   -1.4002 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1355    0.5423   -1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5029    1.8507   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4725   -0.2640   -0.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8823    0.9336    0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520    0.7934    2.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7720   -1.1872    2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -1.7546    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6738   -1.0855   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -1.2949   -1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1023   -0.9829   -1.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3496    0.4744   -0.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1635    1.6595    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083    1.3603    1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3892    1.9353    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    0.9497   -2.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -1.5669   -1.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6664   -0.0888   -1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7936    2.3130   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  2  1  0
 15  4  1  0
 13  8  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Benzylidene glucopyranose	MeSH
Benzylidene glucose	MeSH

Chemical Formula

C₁₃H₁₆O₆

Average Molecular Weight

268.2625

Monoisotopic Molecular Weight

268.094688244

IUPAC Name

2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-6,7,8-triol

Traditional Name

2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-6,7,8-triol

CAS Registry Number

Not Available

SMILES

OC1OC2COC(OC2C(O)C1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H16O6/c14-9-10(15)12(16)18-8-6-17-13(19-11(8)9)7-4-2-1-3-5-7/h1-5,8-16H,6H2

InChI Key

FOLRUCXBTYDAQK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyranodioxins

Sub Class

Not Available

Direct Parent

Pyranodioxins

Alternative Parents

Substituents

Pyranodioxin
Meta-dioxane
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
1,2-diol
Secondary alcohol
Hemiacetal
Oxacycle
Polyol
Acetal
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (FooDB: )

Food

Fruit

Other fruit

Fig (FooDB: FOOD00081)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Carcinostatic (FooDB: )

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.3	ALOGPS
logP	0.23	ChemAxon
logS	-0.69	ALOGPS
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.81 m³·mol⁻¹	ChemAxon
Polarizability	26.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	156.79	30932474
DeepCCS	[M-H]-	154.433	30932474
DeepCCS	[M-2H]-	187.359	30932474
DeepCCS	[M+Na]+	162.884	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.6	32859911
AllCCS	[M+NH4]+	167.6	32859911
AllCCS	[M+Na]+	168.6	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-O,6-O-Benzylidene-alpha-D-glucopyranose	OC1OC2COC(OC2C(O)C1O)C1=CC=CC=C1	3458.0	Standard polar	33892256
4-O,6-O-Benzylidene-alpha-D-glucopyranose	OC1OC2COC(OC2C(O)C1O)C1=CC=CC=C1	2362.2	Standard non polar	33892256
4-O,6-O-Benzylidene-alpha-D-glucopyranose	OC1OC2COC(OC2C(O)C1O)C1=CC=CC=C1	2379.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zgr-2890000000-0e374ec0cff7d0f59360	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 10V, Positive-QTOF	splash10-014i-1290000000-a77fa3cbb7ba34396941	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 20V, Positive-QTOF	splash10-0hka-0920000000-ea9aad27f89ee436fcec	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 40V, Positive-QTOF	splash10-0006-9200000000-ddd7a7bcb9c89c444ad2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 10V, Negative-QTOF	splash10-014i-1790000000-11262f83042cb466a21b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 20V, Negative-QTOF	splash10-08fu-3910000000-e402c0a40543b6ac78fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 40V, Negative-QTOF	splash10-0a4i-5900000000-297135de5d90b9950b5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 10V, Positive-QTOF	splash10-014i-0090000000-894c47a2960853171a7d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 20V, Positive-QTOF	splash10-016u-0390000000-0e5c4f5f3aaa9c4e34a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 40V, Positive-QTOF	splash10-00kf-9820000000-608d4cde27194267d278	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 10V, Negative-QTOF	splash10-014i-0090000000-3da515d4f1f3d3226d84	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 20V, Negative-QTOF	splash10-004i-2940000000-5d0b91531dff98a1b712	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O,6-O-Benzylidene-alpha-D-glucopyranose 40V, Negative-QTOF	splash10-056r-9720000000-84246a29d98b79d60b16	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005447

KNApSAcK ID

Not Available

Chemspider ID

90445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100089

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-O,6-O-Benzylidene-alpha-D-glucopyranose (HMDB0245694)

MOL for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

3D MOL for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

3D SDF for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

3D-SDF for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

PDB for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

3D PDB for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

SMILES for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

INCHI for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

Structure for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

3D Structure for HMDB0245694 (4-O,6-O-Benzylidene-alpha-D-glucopyranose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra