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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:45:00 UTC

Update Date

2021-09-24 03:45:00 UTC

HMDB ID

HMDB0303674

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vacciniin

Description

Vacciniin, also known as 6-O-benzoyl-D-glucopyranoside, is a member of the class of compounds known as benzoic acid esters. Benzoic acid esters are ester derivatives of benzoic acid. Vacciniin is soluble (in water) and a very weakly acidic compound (based on its pKa). Vacciniin can be found in american cranberry, which makes vacciniin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303674
     RDKit          3D
Vacciniin
 36 37  0  0  0  0  0  0  0  0999 V2000
    2.2697   -0.7495    2.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -0.4488    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209   -0.5675    0.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275   -1.0253    1.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4420   -1.0493    0.2319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5727   -1.4800    0.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -0.5016    1.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0837    0.4234    2.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    0.1856   -0.1276 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1904   -0.3640   -0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.1996   -1.2162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0974    1.2870   -2.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    0.2542   -0.5019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5601    0.3528   -1.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847    0.0243    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461    0.3555   -1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.8006   -1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4598    0.9119   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6085    0.5836    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5059    0.1358    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -0.2832    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -2.0243    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -1.8232   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3997   -1.0120    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820   -0.0158    2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    1.2603    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3609   -1.1811   -0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984   -0.7712   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018    0.9891   -2.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    1.1327    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.2803   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856    0.2646   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570    1.0669   -2.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3072    1.2531   -1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5616    0.6659    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5972   -0.1305    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  5  1  0
 20 15  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  7 24  1  1
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  6
 12 29  1  0
 13 30  1  1
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv1533007131516372D          

 25 26  0  0  1  0            999 V2000
   -3.5724   -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
   -4.2868    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
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4302    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  1  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13 11  1  0  0  0  0
  9 14  1  6  0  0  0
 10 15  1  6  0  0  0
 11 16  1  6  0  0  0
 17 12  2  0  0  0  0
 13 18  1  1  0  0  0
 19  6  1  0  0  0  0
 19 12  1  0  0  0  0
 20  8  1  0  0  0  0
 20 13  1  0  0  0  0
  8 21  1  6  0  0  0
  9 22  1  1  0  0  0
 10 23  1  6  0  0  0
 11 24  1  1  0  0  0
 13 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0303674

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(O)O[C@]([H])(COC(=O)C2=CC=CC=C2)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O7/c14-9-8(20-13(18)11(16)10(9)15)6-19-12(17)7-4-2-1-3-5-7/h1-5,8-11,13-16,18H,6H2/t8-,9-,10+,11-,13-/m1/s1

> <INCHI_KEY>
MRDRXKCKIMVUHN-BZNQNGANSA-N

> <FORMULA>
C13H16O7

> <MOLECULAR_WEIGHT>
284.264

> <EXACT_MASS>
284.089602855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.26225569519362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl benzoate

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-0.4372393693333334

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.692118057207125

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.298285318132871

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649083918254459

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
65.7454

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303674
     RDKit          3D
Vacciniin
 36 37  0  0  0  0  0  0  0  0999 V2000
    2.2697   -0.7495    2.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -0.4488    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209   -0.5675    0.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275   -1.0253    1.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4420   -1.0493    0.2319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5727   -1.4800    0.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -0.5016    1.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0837    0.4234    2.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    0.1856   -0.1276 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1904   -0.3640   -0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.1996   -1.2162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0974    1.2870   -2.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    0.2542   -0.5019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5601    0.3528   -1.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847    0.0243    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461    0.3555   -1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.8006   -1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4598    0.9119   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6085    0.5836    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5059    0.1358    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -0.2832    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -2.0243    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -1.8232   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3997   -1.0120    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820   -0.0158    2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    1.2603    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3609   -1.1811   -0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984   -0.7712   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018    0.9891   -2.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    1.1327    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.2803   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856    0.2646   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570    1.0669   -2.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3072    1.2531   -1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5616    0.6659    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5972   -0.1305    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  5  1  0
 20 15  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  7 24  1  1
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  6
 12 29  1  0
 13 30  1  1
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.003   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002   9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0     -10.669  10.780   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0     -13.337   9.240   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -13.337   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -10.669   6.160   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      -8.002   7.700   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -9.336  10.010   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0     -10.669   7.700   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0     -12.003  10.010   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0     -13.337   7.700   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    8   19                                                       
CONECT    7    4    5   12                                                  
CONECT    8    6    9   20   21                                             
CONECT    9    8   10   14   22                                             
CONECT   10    9   11   15   23                                             
CONECT   11   10   13   16   24                                             
CONECT   12    7   17   19                                                  
CONECT   13   11   18   20   25                                             
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    6   12                                                       
CONECT   20    8   13                                                       
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   13                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0303674
HETATM    1  O1  UNL     1       2.270  -0.750   2.229  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.156  -0.449   1.032  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.921  -0.567   0.437  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.227  -1.025   1.157  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.442  -1.049   0.232  1.00  0.00           C  
HETATM    6  O3  UNL     1      -2.573  -1.480   0.868  1.00  0.00           O  
HETATM    7  C4  UNL     1      -3.509  -0.502   1.115  1.00  0.00           C  
HETATM    8  O4  UNL     1      -3.084   0.423   2.086  1.00  0.00           O  
HETATM    9  C5  UNL     1      -3.999   0.186  -0.128  1.00  0.00           C  
HETATM   10  O5  UNL     1      -5.190  -0.364  -0.601  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.946   0.200  -1.216  1.00  0.00           C  
HETATM   12  O6  UNL     1      -3.097   1.287  -2.073  1.00  0.00           O  
HETATM   13  C7  UNL     1      -1.595   0.254  -0.502  1.00  0.00           C  
HETATM   14  O7  UNL     1      -0.560   0.353  -1.437  1.00  0.00           O  
HETATM   15  C8  UNL     1       3.285   0.024   0.240  1.00  0.00           C  
HETATM   16  C9  UNL     1       3.146   0.356  -1.090  1.00  0.00           C  
HETATM   17  C10 UNL     1       4.236   0.801  -1.812  1.00  0.00           C  
HETATM   18  C11 UNL     1       5.460   0.912  -1.200  1.00  0.00           C  
HETATM   19  C12 UNL     1       5.608   0.584   0.128  1.00  0.00           C  
HETATM   20  C13 UNL     1       4.506   0.136   0.849  1.00  0.00           C  
HETATM   21  H1  UNL     1      -0.396  -0.283   1.964  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.010  -2.024   1.545  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.187  -1.823  -0.551  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.400  -1.012   1.569  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.182  -0.016   2.989  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.182   1.260   0.144  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.361  -1.181  -0.070  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.998  -0.771  -1.750  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.602   0.989  -2.870  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.638   1.133   0.162  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.219   1.280  -1.382  1.00  0.00           H  
HETATM   32  H12 UNL     1       2.186   0.265  -1.558  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.157   1.067  -2.854  1.00  0.00           H  
HETATM   34  H14 UNL     1       6.307   1.253  -1.743  1.00  0.00           H  
HETATM   35  H15 UNL     1       6.562   0.666   0.621  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.597  -0.130   1.901  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   15
CONECT    3    4
CONECT    4    5   21   22
CONECT    5    6   13   23
CONECT    6    7
CONECT    7    8    9   24
CONECT    8   25
CONECT    9   10   11   26
CONECT   10   27
CONECT   11   12   13   28
CONECT   12   29
CONECT   13   14   30
CONECT   14   31
CONECT   15   16   16   20
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   20   36
END

HMDB0303674
     RDKit          3D
Vacciniin
 36 37  0  0  0  0  0  0  0  0999 V2000
    2.2697   -0.7495    2.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -0.4488    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209   -0.5675    0.4369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275   -1.0253    1.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4420   -1.0493    0.2319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5727   -1.4800    0.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088   -0.5016    1.1152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0837    0.4234    2.0856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988    0.1856   -0.1276 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1904   -0.3640   -0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9461    0.1996   -1.2162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0974    1.2870   -2.0728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950    0.2542   -0.5019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5601    0.3528   -1.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2847    0.0243    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461    0.3555   -1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2364    0.8006   -1.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4598    0.9119   -1.1995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6085    0.5836    0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5059    0.1358    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -0.2832    1.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0101   -2.0243    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1869   -1.8232   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3997   -1.0120    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1820   -0.0158    2.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824    1.2603    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3609   -1.1811   -0.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984   -0.7712   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018    0.9891   -2.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6375    1.1327    0.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2187    1.2803   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1856    0.2646   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570    1.0669   -2.8541 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3072    1.2531   -1.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5616    0.6659    0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5972   -0.1305    1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13  5  1  0
 20 15  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  6
  7 24  1  1
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  6
 12 29  1  0
 13 30  1  1
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(2R,3S,4S,5R,6R)-3,4,5,6-Tetrahydroxyoxan-2-yl]methyl benzoic acid	Generator
6-O-Benzoyl-D-glucopyranoside	MeSH
Vacciniin	MeSH

Chemical Formula

C₁₃H₁₆O₇

Average Molecular Weight

284.264

Monoisotopic Molecular Weight

284.089602855

IUPAC Name

[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl benzoate

Traditional Name

[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(O)O[C@]([H])(COC(=O)C2=CC=CC=C2)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C13H16O7/c14-9-8(20-13(18)11(16)10(9)15)6-19-12(17)7-4-2-1-3-5-7/h1-5,8-11,13-16,18H,6H2/t8-,9-,10+,11-,13-/m1/s1

InChI Key

MRDRXKCKIMVUHN-BZNQNGANSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Monosaccharide
Oxane
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

American cranberry (FooDB: FOOD00192)

Process

Not Available

Role

Not Available

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	-0.54	ALOGPS
logP	-0.44	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.75 m³·mol⁻¹	ChemAxon
Polarizability	27.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	166.06	32859911
AllCCS	[M+H-H2O]+	162.665	32859911
AllCCS	[M+Na]+	170.111	32859911
AllCCS	[M+NH4]+	169.207	32859911
AllCCS	[M-H]-	163.636	32859911
AllCCS	[M+Na-2H]-	163.571	32859911
AllCCS	[M+HCOO]-	163.616	32859911
DeepCCS	[M+H]+	158.524	30932474
DeepCCS	[M-H]-	156.129	30932474
DeepCCS	[M-2H]-	189.324	30932474
DeepCCS	[M+Na]+	165.217	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 10V, Positive-QTOF	splash10-07br-0890000000-54064fa3034c45a29944	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 20V, Positive-QTOF	splash10-0bta-1920000000-195ac3390c20cbc854f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 40V, Positive-QTOF	splash10-0a4i-3900000000-430c94baf3a1b031dcf2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 10V, Negative-QTOF	splash10-00e9-2970000000-c68b1718fee94cdbad48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 20V, Negative-QTOF	splash10-00di-4910000000-899cca42502b19790f36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 40V, Negative-QTOF	splash10-00fr-9800000000-8a4042d4a192cefd3953	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 10V, Negative-QTOF	splash10-01qc-1950000000-6f1e281c0de57d01c814	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 20V, Negative-QTOF	splash10-00b9-9800000000-0740d90166d04909c6ef	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 40V, Negative-QTOF	splash10-004i-9300000000-3ad5d4f5f1bb1e216057	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 10V, Positive-QTOF	splash10-00ks-0390000000-bfcbd713d94e17a3d91b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 20V, Positive-QTOF	splash10-0cfs-0910000000-92b9456c9e136138771d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vacciniin 40V, Positive-QTOF	splash10-056s-4900000000-5e84790b6f2f0542636b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB017864

KNApSAcK ID

Not Available

Chemspider ID

16736084

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for Vacciniin (HMDB0303674)

MOL for HMDB0303674 (Vacciniin)

3D MOL for HMDB0303674 (Vacciniin)

3D SDF for HMDB0303674 (Vacciniin)

3D-SDF for HMDB0303674 (Vacciniin)

PDB for HMDB0303674 (Vacciniin)

3D PDB for HMDB0303674 (Vacciniin)

SMILES for HMDB0303674 (Vacciniin)

INCHI for HMDB0303674 (Vacciniin)

Structure for HMDB0303674 (Vacciniin)

3D Structure for HMDB0303674 (Vacciniin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra