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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:17:25 UTC

Update Date

2022-03-07 02:56:42 UTC

HMDB ID

HMDB0040714

Secondary Accession Numbers

HMDB40714

Metabolite Identification

Common Name

Vitilagin

Description

Vitilagin belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Vitilagin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, vitilagin is found, on average, in the highest concentration in common grapes. vitilagin has also been detected, but not quantified in, alcoholic beverages and fruits. This could make vitilagin a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 05061312042D          

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M  END

HMDB0040714
     RDKit          3D
Vitilagin
 83 89  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv0541 05061312042D          

 57 63  0  0  0  0            999 V2000
   -1.0677    5.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0040714

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=CC(=O)C4(O)OC5=C(O)C(O)=CC(=C5C3C4(O)O)C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H26O23/c35-12-1-8(2-13(36)21(12)41)28(45)55-27-24(44)32(56-29(46)9-3-14(37)22(42)15(38)4-9)53-17-7-52-30(47)11-6-18(40)34(51)33(49,50)20(11)19-10(31(48)54-25(17)27)5-16(39)23(43)26(19)57-34/h1-6,17,20,24-25,27,32,35-39,41-44,49-51H,7H2

> <INCHI_KEY>
XPOXLICDNPVKBQ-UHFFFAOYSA-N

> <FORMULA>
C34H26O23

> <MOLECULAR_WEIGHT>
802.5564

> <EXACT_MASS>
802.086487138

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
71.38505771228606

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,11,18,19,23,23-hexahydroxy-2,5,15-trioxo-12-(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16(21),17,19-tetraen-10-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.3426514973333334

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.804784453315074

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.68627986919303

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548940930615129

> <JCHEM_POLAR_SURFACE_AREA>
383.49000000000007

> <JCHEM_REFRACTIVITY>
175.71339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,11,18,19,23,23-hexahydroxy-2,5,15-trioxo-12-(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16(21),17,19-tetraen-10-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040714
     RDKit          3D
Vitilagin
 83 89  0  0  0  0  0  0  0  0999 V2000
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    4.0333   -0.0011    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
  7 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 22 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 37 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  1  0
 41 43  2  0
 43 44  1  0
 43 45  1  0
 45 46  2  0
 46 47  1  0
 47 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  2  0
 50 52  1  0
 52 53  1  0
 52 54  1  0
 52 55  1  0
 55 56  1  0
 55 57  1  0
 48  2  1  0
 35  5  1  0
 46 39  1  0
 55 47  1  0
 19 11  1  0
 34 26  1  0
 54 45  1  0
  4 58  1  0
  4 59  1  0
  5 60  1  0
  7 61  1  0
 12 62  1  0
 14 63  1  0
 16 64  1  0
 18 65  1  0
 19 66  1  0
 20 67  1  0
 21 68  1  0
 22 69  1  0
 27 70  1  0
 29 71  1  0
 31 72  1  0
 33 73  1  0
 34 74  1  0
 35 75  1  0
 40 76  1  0
 42 77  1  0
 44 78  1  0
 47 79  1  0
 49 80  1  0
 53 81  1  0
 56 82  1  0
 57 83  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  O   UNK     0      -1.993  10.056   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.265   8.515   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.996   7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.996   6.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.355   5.344   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.805   4.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.046   5.440   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.345   7.066   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.805   8.007   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.530   9.422   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.416  -8.311   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.550  -6.777   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.288  -5.894   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.422  -4.360   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.818  -3.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.079  -4.592   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.945  -6.126   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.207  -7.009   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.701   5.924   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.307   5.270   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.090   3.766   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.197   2.577   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.905   1.358   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.167   0.475   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.896   7.137   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.572   6.810   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.533   5.979   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.765  -4.127   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.160  -3.476   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.294  -1.942   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.033  -1.059   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.637  -1.710   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.503  -3.244   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.475  -3.941   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -3.493   0.668   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.896   2.087   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.972   2.998   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.382   2.378   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.624   3.289   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.456   4.820   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -7.698   5.730   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.490   0.707   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.624  -0.827   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.020  -1.478   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.154  -3.012   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.892  -3.895   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -8.034   2.669   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -7.469  -2.548   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -6.207  -3.431   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -4.811  -2.780   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -3.550  -3.663   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -3.684  -5.197   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -5.079  -5.848   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -6.341  -4.965   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -7.737  -5.616   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -5.213  -7.382   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -1.307   1.938   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    7   37                                                  
CONECT    7    6    8   40                                                  
CONECT    8    7    9                                                       
CONECT    9    2    8   10   26                                             
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   12   16   18                                                  
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20    4   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   42                                                  
CONECT   24   23   31                                                       
CONECT   25   26                                                            
CONECT   26    5    9   25   27                                             
CONECT   27   26                                                            
CONECT   28   29                                                            
CONECT   29   14   28   30                                                  
CONECT   30   29   31                                                       
CONECT   31   24   30   32                                                  
CONECT   32   31   33   43                                                  
CONECT   33   32                                                            
CONECT   34   16                                                            
CONECT   35   36                                                            
CONECT   36   35   37   57                                                  
CONECT   37    6   36   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   47                                                  
CONECT   40    7   39   41                                                  
CONECT   41   40                                                            
CONECT   42   23   43   57                                                  
CONECT   43   32   42   44                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   51                                                  
CONECT   46   45                                                            
CONECT   47   39                                                            
CONECT   48   49                                                            
CONECT   49   48   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   45   50   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   56                                                  
CONECT   54   49   53   55                                                  
CONECT   55   54                                                            
CONECT   56   53                                                            
CONECT   57   36   42                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  126    0
END

COMPND    HMDB0040714
HETATM    1  O1  UNL     1       1.893   1.394  -3.423  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.207   0.291  -2.788  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.470  -0.801  -2.944  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.379  -1.480  -2.562  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.083  -1.336  -1.121  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.253  -2.036  -1.022  1.00  0.00           O  
HETATM    7  C4  UNL     1      -2.160  -1.631  -0.086  1.00  0.00           C  
HETATM    8  O4  UNL     1      -3.190  -2.559  -0.030  1.00  0.00           O  
HETATM    9  C5  UNL     1      -3.489  -3.301   1.096  1.00  0.00           C  
HETATM   10  O5  UNL     1      -2.768  -3.086   2.079  1.00  0.00           O  
HETATM   11  C6  UNL     1      -4.589  -4.257   1.071  1.00  0.00           C  
HETATM   12  C7  UNL     1      -4.902  -5.006   2.188  1.00  0.00           C  
HETATM   13  C8  UNL     1      -5.928  -5.914   2.202  1.00  0.00           C  
HETATM   14  O6  UNL     1      -6.212  -6.650   3.350  1.00  0.00           O  
HETATM   15  C9  UNL     1      -6.705  -6.118   1.072  1.00  0.00           C  
HETATM   16  O7  UNL     1      -7.749  -7.033   1.067  1.00  0.00           O  
HETATM   17  C10 UNL     1      -6.398  -5.374  -0.046  1.00  0.00           C  
HETATM   18  O8  UNL     1      -7.118  -5.508  -1.223  1.00  0.00           O  
HETATM   19  C11 UNL     1      -5.362  -4.462  -0.048  1.00  0.00           C  
HETATM   20  C12 UNL     1      -2.566  -0.231  -0.463  1.00  0.00           C  
HETATM   21  O9  UNL     1      -2.899  -0.174  -1.801  1.00  0.00           O  
HETATM   22  C13 UNL     1      -1.360   0.613  -0.117  1.00  0.00           C  
HETATM   23  O10 UNL     1      -1.521   1.978  -0.397  1.00  0.00           O  
HETATM   24  C14 UNL     1      -1.555   2.973   0.562  1.00  0.00           C  
HETATM   25  O11 UNL     1      -1.431   2.606   1.750  1.00  0.00           O  
HETATM   26  C15 UNL     1      -1.726   4.346   0.151  1.00  0.00           C  
HETATM   27  C16 UNL     1      -1.868   4.743  -1.152  1.00  0.00           C  
HETATM   28  C17 UNL     1      -2.026   6.081  -1.485  1.00  0.00           C  
HETATM   29  O12 UNL     1      -2.169   6.473  -2.813  1.00  0.00           O  
HETATM   30  C18 UNL     1      -2.045   7.050  -0.517  1.00  0.00           C  
HETATM   31  O13 UNL     1      -2.204   8.410  -0.840  1.00  0.00           O  
HETATM   32  C19 UNL     1      -1.904   6.683   0.807  1.00  0.00           C  
HETATM   33  O14 UNL     1      -1.919   7.629   1.803  1.00  0.00           O  
HETATM   34  C20 UNL     1      -1.746   5.340   1.135  1.00  0.00           C  
HETATM   35  C21 UNL     1      -0.049   0.060  -0.647  1.00  0.00           C  
HETATM   36  O15 UNL     1       0.945   0.401   0.209  1.00  0.00           O  
HETATM   37  C22 UNL     1       1.633   0.095   1.311  1.00  0.00           C  
HETATM   38  O16 UNL     1       1.164  -0.430   2.408  1.00  0.00           O  
HETATM   39  C23 UNL     1       3.098   0.315   1.463  1.00  0.00           C  
HETATM   40  C24 UNL     1       3.527   0.871   2.687  1.00  0.00           C  
HETATM   41  C25 UNL     1       4.859   1.113   2.948  1.00  0.00           C  
HETATM   42  O17 UNL     1       5.248   1.663   4.165  1.00  0.00           O  
HETATM   43  C26 UNL     1       5.763   0.789   1.961  1.00  0.00           C  
HETATM   44  O18 UNL     1       7.109   1.048   2.260  1.00  0.00           O  
HETATM   45  C27 UNL     1       5.386   0.242   0.749  1.00  0.00           C  
HETATM   46  C28 UNL     1       4.033  -0.001   0.488  1.00  0.00           C  
HETATM   47  C29 UNL     1       3.722  -0.598  -0.828  1.00  0.00           C  
HETATM   48  C30 UNL     1       3.384   0.317  -1.922  1.00  0.00           C  
HETATM   49  C31 UNL     1       4.279   1.277  -2.177  1.00  0.00           C  
HETATM   50  C32 UNL     1       5.727   0.995  -2.022  1.00  0.00           C  
HETATM   51  O19 UNL     1       6.618   1.791  -2.324  1.00  0.00           O  
HETATM   52  C33 UNL     1       6.102  -0.335  -1.464  1.00  0.00           C  
HETATM   53  O20 UNL     1       7.194  -0.875  -2.145  1.00  0.00           O  
HETATM   54  O21 UNL     1       6.426  -0.024  -0.123  1.00  0.00           O  
HETATM   55  C34 UNL     1       4.988  -1.324  -1.368  1.00  0.00           C  
HETATM   56  O22 UNL     1       4.637  -1.897  -2.575  1.00  0.00           O  
HETATM   57  O23 UNL     1       5.309  -2.265  -0.395  1.00  0.00           O  
HETATM   58  H1  UNL     1       0.564  -2.585  -2.787  1.00  0.00           H  
HETATM   59  H2  UNL     1      -0.563  -1.292  -3.158  1.00  0.00           H  
HETATM   60  H3  UNL     1       0.664  -1.922  -0.505  1.00  0.00           H  
HETATM   61  H4  UNL     1      -1.658  -1.614   0.904  1.00  0.00           H  
HETATM   62  H5  UNL     1      -4.316  -4.876   3.097  1.00  0.00           H  
HETATM   63  H6  UNL     1      -5.647  -6.508   4.186  1.00  0.00           H  
HETATM   64  H7  UNL     1      -7.925  -7.547   1.914  1.00  0.00           H  
HETATM   65  H8  UNL     1      -7.879  -6.169  -1.242  1.00  0.00           H  
HETATM   66  H9  UNL     1      -5.112  -3.872  -0.921  1.00  0.00           H  
HETATM   67  H10 UNL     1      -3.390   0.155   0.200  1.00  0.00           H  
HETATM   68  H11 UNL     1      -3.798   0.198  -1.970  1.00  0.00           H  
HETATM   69  H12 UNL     1      -1.278   0.543   1.000  1.00  0.00           H  
HETATM   70  H13 UNL     1      -1.859   4.020  -1.941  1.00  0.00           H  
HETATM   71  H14 UNL     1      -2.284   7.424  -3.076  1.00  0.00           H  
HETATM   72  H15 UNL     1      -2.219   9.121  -0.140  1.00  0.00           H  
HETATM   73  H16 UNL     1      -1.817   7.353   2.759  1.00  0.00           H  
HETATM   74  H17 UNL     1      -1.638   5.059   2.163  1.00  0.00           H  
HETATM   75  H18 UNL     1       0.107   0.697  -1.577  1.00  0.00           H  
HETATM   76  H19 UNL     1       2.801   1.125   3.480  1.00  0.00           H  
HETATM   77  H20 UNL     1       4.521   1.870   4.832  1.00  0.00           H  
HETATM   78  H21 UNL     1       7.789   0.821   1.558  1.00  0.00           H  
HETATM   79  H22 UNL     1       2.980  -1.395  -0.655  1.00  0.00           H  
HETATM   80  H23 UNL     1       3.978   2.258  -2.500  1.00  0.00           H  
HETATM   81  H24 UNL     1       8.004  -0.744  -1.623  1.00  0.00           H  
HETATM   82  H25 UNL     1       4.931  -2.860  -2.559  1.00  0.00           H  
HETATM   83  H26 UNL     1       4.836  -2.141   0.444  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   48
CONECT    3    4
CONECT    4    5   58   59
CONECT    5    6   35   60
CONECT    6    7
CONECT    7    8   20   61
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   19
CONECT   12   13   62
CONECT   13   14   15   15
CONECT   14   63
CONECT   15   16   17
CONECT   16   64
CONECT   17   18   19   19
CONECT   18   65
CONECT   19   66
CONECT   20   21   22   67
CONECT   21   68
CONECT   22   23   35   69
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   27   34
CONECT   27   28   70
CONECT   28   29   30   30
CONECT   29   71
CONECT   30   31   32
CONECT   31   72
CONECT   32   33   34   34
CONECT   33   73
CONECT   34   74
CONECT   35   36   75
CONECT   36   37
CONECT   37   38   38   39
CONECT   39   40   40   46
CONECT   40   41   76
CONECT   41   42   43   43
CONECT   42   77
CONECT   43   44   45
CONECT   44   78
CONECT   45   46   46   54
CONECT   46   47
CONECT   47   48   55   79
CONECT   48   49   49
CONECT   49   50   80
CONECT   50   51   51   52
CONECT   52   53   54   55
CONECT   53   81
CONECT   55   56   57
CONECT   56   82
CONECT   57   83
END

HMDB0040714
     RDKit          3D
Vitilagin
 83 89  0  0  0  0  0  0  0  0999 V2000
    1.8926    1.3943   -3.4227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    0.2906   -2.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4703   -0.8015   -2.9437 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3791   -1.4796   -2.5624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -1.3358   -1.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2533   -2.0360   -1.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1605   -1.6313   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1898   -2.5591   -0.0300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4890   -3.3010    1.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681   -3.0863    2.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5887   -4.2569    1.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9017   -5.0056    2.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9277   -5.9138    2.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2115   -6.6500    3.3498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7052   -6.1184    1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7485   -7.0333    1.0667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3979   -5.3740   -0.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1176   -5.5076   -1.2235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3623   -4.4622   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663   -0.2315   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991   -0.1741   -1.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598    0.6130   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212    1.9784   -0.3968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5546    2.9730    0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    2.6064    1.7504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7259    4.3464    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8676    4.7430   -1.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0257    6.0809   -1.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1691    6.4731   -2.8127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    7.0502   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043    8.4096   -0.8400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    6.6829    0.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    7.6291    1.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7462    5.3399    1.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0493    0.0599   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9452    0.4012    0.2093 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6325    0.0948    1.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1636   -0.4297    2.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0976    0.3147    1.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5274    0.8709    2.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8590    1.1128    2.9475 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2477    1.6625    4.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7630    0.7885    1.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1094    1.0481    2.2599 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3863    0.2424    0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0333   -0.0011    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7220   -0.5979   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    0.3171   -1.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2789    1.2773   -2.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7267    0.9953   -2.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181    1.7907   -2.3245 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1023   -0.3346   -1.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1940   -0.8747   -2.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4256   -0.0236   -0.1232 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9878   -1.3239   -1.3677 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6365   -1.8968   -2.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3088   -2.2645   -0.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5641   -2.5850   -2.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -1.2923   -3.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6643   -1.9218   -0.5052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6576   -1.6136    0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164   -4.8765    3.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6467   -6.5081    4.1864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9247   -7.5472    1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8789   -6.1691   -1.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1119   -3.8722   -0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895    0.1547    0.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7981    0.1981   -1.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    0.5433    1.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8590    4.0204   -1.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2837    7.4240   -3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2191    9.1209   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8166    7.3535    2.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6376    5.0586    2.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1070    0.6966   -1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010    1.1245    3.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5209    1.8698    4.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7892    0.8209    1.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9798   -1.3955   -0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782    2.2583   -2.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0037   -0.7436   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310   -2.8598   -2.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8361   -2.1409    0.4436 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
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,11,18,19,23,23-Hexahydroxy-2,5,15-trioxo-10-(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16,18,20-tetraen-12-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₃₄H₂₆O₂₃

Average Molecular Weight

802.5564

Monoisotopic Molecular Weight

802.086487138

IUPAC Name

1,11,18,19,23,23-hexahydroxy-2,5,15-trioxo-12-(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]tetracosa-3,16(21),17,19-tetraen-10-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

85200-63-1

SMILES

OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=CC(=O)C4(O)OC5=C(O)C(O)=CC(=C5C3C4(O)O)C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C34H26O23/c35-12-1-8(2-13(36)21(12)41)28(45)55-27-24(44)32(56-29(46)9-3-14(37)22(42)15(38)4-9)53-17-7-52-30(47)11-6-18(40)34(51)33(49,50)20(11)19-10(31(48)54-25(17)27)5-16(39)23(43)26(19)57-34/h1-6,17,20,24-25,27,32,35-39,41-44,49-51H,7H2

InChI Key

XPOXLICDNPVKBQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Tetracarboxylic acid or derivatives
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzopyran
1-benzopyran
Benzoate ester
Chromane
Benzenetriol
Pyrogallol derivative
Benzoic acid or derivatives
Benzoyl
Cyclohexenone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Hemiacetal
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carbonyl hydrate
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040714)
Cytoplasm (HMDB: HMDB0040714)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040714)

Source

Exogenous

Food

Food (HMDB: HMDB0040714)

Fruit

Berry

Common grape (FooDB: FOOD00204)

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0040714)

Not Available

Nutrient (HMDB: HMDB0040714)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	220 - 228 °C	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
Water Solubility	5.09 g/L	ALOGPS
logP	1.63	ALOGPS
logP	1.34	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.69	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	383.49 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	175.71 m³·mol⁻¹	ChemAxon
Polarizability	71.39 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	259.825	30932474
DeepCCS	[M-H]-	257.93	30932474
DeepCCS	[M-2H]-	291.888	30932474
DeepCCS	[M+Na]+	265.908	30932474
AllCCS	[M+H]+	250.6	32859911
AllCCS	[M+H-H2O]+	250.5	32859911
AllCCS	[M+NH4]+	250.7	32859911
AllCCS	[M+Na]+	250.7	32859911
AllCCS	[M-H]-	250.8	32859911
AllCCS	[M+Na-2H]-	253.7	32859911
AllCCS	[M+HCOO]-	257.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vitilagin	OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=CC(=O)C4(O)OC5=C(O)C(O)=CC(=C5C3C4(O)O)C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C1	8457.6	Standard polar	33892256
Vitilagin	OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=CC(=O)C4(O)OC5=C(O)C(O)=CC(=C5C3C4(O)O)C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C1	5851.8	Standard non polar	33892256
Vitilagin	OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=CC(=O)C4(O)OC5=C(O)C(O)=CC(=C5C3C4(O)O)C(=O)OC2C1OC(=O)C1=CC(O)=C(O)C(O)=C1	7020.6	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 - Vitilagin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vitilagin GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-10-19	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 - Vitilagin 10V, Positive-QTOF	splash10-0uk9-0900002110-731c04c39ffa3504f5fe	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 20V, Positive-QTOF	splash10-0udi-0900001100-d0b6b6dcc6feb4a129f6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 40V, Positive-QTOF	splash10-0ufr-0900100100-1991595f89ba7591901c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 10V, Negative-QTOF	splash10-0uxr-0900001130-b5590bd57883d4d8286a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 20V, Negative-QTOF	splash10-016r-0922001100-fce5ecb816e387c847a6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 40V, Negative-QTOF	splash10-014i-0903000000-d69e16f6aa32d933983b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 10V, Negative-QTOF	splash10-0udi-0300101090-3ea464e07cb1875cc14a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 20V, Negative-QTOF	splash10-0ue9-0901202420-af0676266fe5231d2cee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 40V, Negative-QTOF	splash10-0g2c-2901001410-e0b3967fb31e0a0cd8ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 10V, Positive-QTOF	splash10-0f8i-0800009120-e98898ea2c6d9203970b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 20V, Positive-QTOF	splash10-0udi-0900005460-8bbbca8515f1a6c9494c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vitilagin 40V, Positive-QTOF	splash10-0w29-2701020900-319e6396e544e5485052	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020520

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752915

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Vitilagin (HMDB0040714)

MOL for HMDB0040714 (Vitilagin)

3D MOL for HMDB0040714 (Vitilagin)

3D SDF for HMDB0040714 (Vitilagin)

3D-SDF for HMDB0040714 (Vitilagin)

PDB for HMDB0040714 (Vitilagin)

3D PDB for HMDB0040714 (Vitilagin)

SMILES for HMDB0040714 (Vitilagin)

INCHI for HMDB0040714 (Vitilagin)

Structure for HMDB0040714 (Vitilagin)

3D Structure for HMDB0040714 (Vitilagin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra