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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:28:15 UTC

Update Date

2021-09-23 03:28:15 UTC

HMDB ID

HMDB0301899

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Delphinidin 3-caffeoylglucoside

Description

Delphinidin 3-caffeoylglucoside is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Delphinidin 3-caffeoylglucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Delphinidin 3-caffeoylglucoside can be found in common grape, which makes delphinidin 3-caffeoylglucoside a potential biomarker for the consumption of this food product.

Structure

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


  Mrv0541 02241212192D          

 45 49  0  0  0  0            999 V2000
   -3.2411    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    0.2652    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.8121   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313    1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832    1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6700    0.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -2.2098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602   -0.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602    1.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313    2.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -2.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -3.4473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3832   -3.8598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3313   -3.4473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3313   -2.6223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3832   -2.2098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3832   -1.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457   -2.2098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -3.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832   -4.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458   -3.8598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -8.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -8.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -7.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -7.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -7.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -8.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -8.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -9.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -6.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -5.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -5.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -4.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -4.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
  4 18  1  0  0  0  0
  9 28  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 12 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  1  1  0  0  0
 25 24  1  0  0  0  0
 24 31  1  6  0  0  0
 25 26  1  0  0  0  0
 25 32  1  1  0  0  0
 26 27  1  0  0  0  0
 26 29  1  6  0  0  0
 27 28  1  1  0  0  0
 30 45  1  0  0  0  0
 33 34  2  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 39  1  0  0  0  0
 33 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
M  CHG  1   7   1
M  END

HMDB0301899
     RDKit          3D
Delphinidin 3-caffeoylglucoside
 72 76  0  0  0  0  0  0  0  0999 V2000
    4.1764   -0.1011   -3.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135   -0.1465   -2.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7938   -0.1663   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484   -0.2082   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924   -0.2310    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691   -0.2672    1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8316   -0.2902    2.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9581   -0.2794    1.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2105   -0.3049    1.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8068   -0.2440   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9189   -0.2322   -0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5137   -0.2204   -0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3304   -0.1747   -1.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9836   -0.1487   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748   -0.2027   -0.5857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2607   -0.1629   -0.9202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -0.3034    0.1526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4605   -0.2286   -0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.6517    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355    1.7319    1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093    2.6207    1.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    3.7074    2.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479    3.8686    2.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    4.6069    2.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0840    4.3895    2.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0644    5.2986    2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3576    3.3248    1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3715    2.4090    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    1.4135    0.1203 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.7186    0.4935   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1816   -0.5640   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -1.5462   -1.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -2.5563   -2.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267   -3.5350   -2.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2070   -2.5636   -2.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6446   -3.5933   -3.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0343   -1.5811   -2.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3660   -1.5789   -2.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5120   -0.5868   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947   -1.5862    0.9193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7626   -1.6398    1.9953 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281   -1.5186    1.4747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8681   -2.6403    2.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -1.3966    0.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7803   -1.4183    0.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020   -0.1467   -2.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212   -0.2261    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6946   -0.2755    2.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -0.3192    3.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0363   -0.2975    1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8801   -0.2073   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4590   -0.1928   -1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9020    0.8639   -2.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246   -0.9553   -2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    0.7007    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    0.5135    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526    1.8873    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    4.6417    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894    5.4398    3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5860    5.0908    3.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500    3.1534    0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369   -1.6175   -1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3786   -4.2630   -3.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5906   -3.6683   -3.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7804   -2.2653   -3.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2211    0.1550   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297   -2.4931    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4888   -1.0055    2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105   -0.5694    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311   -2.8192    2.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.3271   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800   -1.0959    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 17 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 12  5  1  0
 44 15  1  0
 30 19  1  0
 39 31  1  0
 28 21  1  0
  3 46  1  0
  4 47  1  0
  6 48  1  0
  7 49  1  0
  9 50  1  0
 11 51  1  0
 12 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  1
 17 56  1  1
 20 57  1  0
 23 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 32 62  1  0
 34 63  1  0
 36 64  1  0
 38 65  1  0
 39 66  1  0
 40 67  1  6
 41 68  1  0
 42 69  1  1
 43 70  1  0
 44 71  1  6
 45 72  1  0
M  CHG  1  29   1
M  END


  Mrv0541 02241212192D          

 45 49  0  0  0  0            999 V2000
   -3.2411    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121    0.2652    0.0000 O   0  3  0  0  0  0  0  0  0  0  0  0
   -1.8121   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313    1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832    1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6700    0.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7602   -0.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7602    1.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3313    2.3277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -2.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0977   -3.4473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3832   -3.8598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3313   -3.4473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3313   -2.6223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3832   -2.2098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3832   -1.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457   -2.2098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -3.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3832   -4.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458   -3.8598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -8.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -8.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -7.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -7.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -7.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -8.3973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -8.8098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -9.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -6.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -5.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -5.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2411   -4.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8121   -4.6848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
  4 18  1  0  0  0  0
  9 28  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 12 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  1  1  0  0  0
 25 24  1  0  0  0  0
 24 31  1  6  0  0  0
 25 26  1  0  0  0  0
 25 32  1  1  0  0  0
 26 27  1  0  0  0  0
 26 29  1  6  0  0  0
 27 28  1  1  0  0  0
 30 45  1  0  0  0  0
 33 34  2  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 34 39  1  0  0  0  0
 33 40  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
M  CHG  1   7   1
M  END
> <DATABASE_ID>
HMDB0301899

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O15/c31-14-8-17(33)15-10-22(29(43-21(15)9-14)13-6-19(35)25(38)20(36)7-13)44-30-28(41)27(40)26(39)23(45-30)11-42-24(37)4-2-12-1-3-16(32)18(34)5-12/h1-10,23,26-28,30,39-41H,11H2,(H6-,31,32,33,34,35,36,37,38)/p+1/t23-,26-,27+,28-,30-/m1/s1

> <INCHI_KEY>
CPESTIBYQUOXSA-LHRGPQAGSA-O

> <FORMULA>
C30H27O15

> <MOLECULAR_WEIGHT>
627.5264

> <EXACT_MASS>
627.134995194

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
61.07287704152896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
3.231899999999999

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.288909534904704

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.365985583394704

> <JCHEM_PKA_STRONGEST_BASIC>
-3.95430753631397

> <JCHEM_POLAR_SURFACE_AREA>
260.2

> <JCHEM_REFRACTIVITY>
161.7679

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301899
     RDKit          3D
Delphinidin 3-caffeoylglucoside
 72 76  0  0  0  0  0  0  0  0999 V2000
    4.1764   -0.1011   -3.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135   -0.1465   -2.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7938   -0.1663   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484   -0.2082   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924   -0.2310    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691   -0.2672    1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8316   -0.2902    2.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9581   -0.2794    1.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2105   -0.3049    1.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8068   -0.2440   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9189   -0.2322   -0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5137   -0.2204   -0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3304   -0.1747   -1.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9836   -0.1487   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748   -0.2027   -0.5857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2607   -0.1629   -0.9202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -0.3034    0.1526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4605   -0.2286   -0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.6517    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355    1.7319    1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093    2.6207    1.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    3.7074    2.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479    3.8686    2.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    4.6069    2.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0840    4.3895    2.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0644    5.2986    2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3576    3.3248    1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3715    2.4090    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    1.4135    0.1203 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.7186    0.4935   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1816   -0.5640   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -1.5462   -1.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -2.5563   -2.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267   -3.5350   -2.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2070   -2.5636   -2.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6446   -3.5933   -3.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0343   -1.5811   -2.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3660   -1.5789   -2.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5120   -0.5868   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947   -1.5862    0.9193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7626   -1.6398    1.9953 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281   -1.5186    1.4747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8681   -2.6403    2.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -1.3966    0.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7803   -1.4183    0.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020   -0.1467   -2.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212   -0.2261    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6946   -0.2755    2.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -0.3192    3.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0363   -0.2975    1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8801   -0.2073   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4590   -0.1928   -1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9020    0.8639   -2.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246   -0.9553   -2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    0.7007    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    0.5135    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526    1.8873    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    4.6417    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894    5.4398    3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5860    5.0908    3.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500    3.1534    0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369   -1.6175   -1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3786   -4.2630   -3.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5906   -3.6683   -3.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7804   -2.2653   -3.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2211    0.1550   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297   -2.4931    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4888   -1.0055    2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105   -0.5694    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311   -2.8192    2.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.3271   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800   -1.0959    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 17 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 12  5  1  0
 44 15  1  0
 30 19  1  0
 39 31  1  0
 28 21  1  0
  3 46  1  0
  4 47  1  0
  6 48  1  0
  7 49  1  0
  9 50  1  0
 11 51  1  0
 12 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  1
 17 56  1  1
 20 57  1  0
 23 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 32 62  1  0
 34 63  1  0
 36 64  1  0
 38 65  1  0
 39 66  1  0
 40 67  1  6
 41 68  1  0
 42 69  1  1
 43 70  1  0
 44 71  1  6
 45 72  1  0
M  CHG  1  29   1
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      -6.050   0.495   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.384  -0.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.384  -1.815   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.050  -2.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.716  -1.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.716  -0.275   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.383   0.495   0.000  0.00  0.00           O+1
HETATM    8  C   UNK     0      -3.383  -2.585   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.049  -1.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.049  -0.275   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.715   0.495   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.618   2.805   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.715   2.035   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.618  -0.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.952   0.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.952   2.035   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.717   0.495   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.050  -4.125   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.286  -0.275   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.286   2.805   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.618   4.345   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.049  -4.895   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.049  -6.435   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.715  -7.205   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.618  -6.435   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.618  -4.895   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.715  -4.125   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.715  -2.585   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.952  -4.125   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.383  -7.205   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.715  -8.745   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.952  -7.205   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -6.050 -16.445   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.716 -15.675   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.716 -14.135   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.050 -13.365   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -7.384 -14.135   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.384 -15.675   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.383 -16.445   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -6.050 -17.985   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -6.050 -11.825   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.716 -11.055   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.716  -9.515   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.050  -8.745   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -3.383  -8.745   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   21                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   12   15   20                                                  
CONECT   17    2                                                            
CONECT   18    4                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   12                                                            
CONECT   22   23   27                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   29                                                  
CONECT   27   22   26   28                                                  
CONECT   28    9   27                                                       
CONECT   29   26                                                            
CONECT   30   23   45                                                       
CONECT   31   24                                                            
CONECT   32   25                                                            
CONECT   33   34   38   40                                                  
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   33   37                                                       
CONECT   39   34                                                            
CONECT   40   33                                                            
CONECT   41   36   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   30   43                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

COMPND    HMDB0301899
HETATM    1  O1  UNL     1       4.176  -0.101  -3.372  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.414  -0.146  -2.140  1.00  0.00           C  
HETATM    3  C2  UNL     1       5.794  -0.166  -1.685  1.00  0.00           C  
HETATM    4  C3  UNL     1       6.048  -0.208  -0.396  1.00  0.00           C  
HETATM    5  C4  UNL     1       7.392  -0.231   0.151  1.00  0.00           C  
HETATM    6  C5  UNL     1       7.569  -0.267   1.535  1.00  0.00           C  
HETATM    7  C6  UNL     1       8.832  -0.290   2.036  1.00  0.00           C  
HETATM    8  C7  UNL     1       9.958  -0.279   1.239  1.00  0.00           C  
HETATM    9  O2  UNL     1      11.211  -0.305   1.840  1.00  0.00           O  
HETATM   10  C8  UNL     1       9.807  -0.244  -0.120  1.00  0.00           C  
HETATM   11  O3  UNL     1      10.919  -0.232  -0.947  1.00  0.00           O  
HETATM   12  C9  UNL     1       8.514  -0.220  -0.643  1.00  0.00           C  
HETATM   13  O4  UNL     1       3.330  -0.175  -1.288  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.984  -0.149  -1.789  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.075  -0.203  -0.586  1.00  0.00           C  
HETATM   16  O5  UNL     1      -0.261  -0.163  -0.920  1.00  0.00           O  
HETATM   17  C12 UNL     1      -1.119  -0.303   0.153  1.00  0.00           C  
HETATM   18  O6  UNL     1      -2.461  -0.229  -0.175  1.00  0.00           O  
HETATM   19  C13 UNL     1      -3.431   0.652   0.180  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.136   1.732   1.024  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.109   2.621   1.384  1.00  0.00           C  
HETATM   22  C16 UNL     1      -3.842   3.707   2.225  1.00  0.00           C  
HETATM   23  O7  UNL     1      -2.548   3.869   2.694  1.00  0.00           O  
HETATM   24  C17 UNL     1      -4.819   4.607   2.592  1.00  0.00           C  
HETATM   25  C18 UNL     1      -6.084   4.389   2.091  1.00  0.00           C  
HETATM   26  O8  UNL     1      -7.064   5.299   2.464  1.00  0.00           O  
HETATM   27  C19 UNL     1      -6.358   3.325   1.264  1.00  0.00           C  
HETATM   28  C20 UNL     1      -5.372   2.409   0.888  1.00  0.00           C  
HETATM   29  O9  UNL     1      -5.608   1.413   0.120  1.00  0.00           O1+
HETATM   30  C21 UNL     1      -4.719   0.494  -0.285  1.00  0.00           C  
HETATM   31  C22 UNL     1      -5.182  -0.564  -1.159  1.00  0.00           C  
HETATM   32  C23 UNL     1      -4.390  -1.546  -1.644  1.00  0.00           C  
HETATM   33  C24 UNL     1      -4.872  -2.556  -2.483  1.00  0.00           C  
HETATM   34  O10 UNL     1      -4.027  -3.535  -2.951  1.00  0.00           O  
HETATM   35  C25 UNL     1      -6.207  -2.564  -2.838  1.00  0.00           C  
HETATM   36  O11 UNL     1      -6.645  -3.593  -3.679  1.00  0.00           O  
HETATM   37  C26 UNL     1      -7.034  -1.581  -2.363  1.00  0.00           C  
HETATM   38  O12 UNL     1      -8.366  -1.579  -2.711  1.00  0.00           O  
HETATM   39  C27 UNL     1      -6.512  -0.587  -1.524  1.00  0.00           C  
HETATM   40  C28 UNL     1      -0.895  -1.586   0.919  1.00  0.00           C  
HETATM   41  O13 UNL     1      -1.763  -1.640   1.995  1.00  0.00           O  
HETATM   42  C29 UNL     1       0.528  -1.519   1.475  1.00  0.00           C  
HETATM   43  O14 UNL     1       0.868  -2.640   2.199  1.00  0.00           O  
HETATM   44  C30 UNL     1       1.432  -1.397   0.269  1.00  0.00           C  
HETATM   45  O15 UNL     1       2.780  -1.418   0.600  1.00  0.00           O  
HETATM   46  H1  UNL     1       6.602  -0.147  -2.385  1.00  0.00           H  
HETATM   47  H2  UNL     1       5.221  -0.226   0.329  1.00  0.00           H  
HETATM   48  H3  UNL     1       6.695  -0.276   2.180  1.00  0.00           H  
HETATM   49  H4  UNL     1       8.986  -0.319   3.124  1.00  0.00           H  
HETATM   50  H5  UNL     1      12.036  -0.298   1.272  1.00  0.00           H  
HETATM   51  H6  UNL     1      10.880  -0.207  -1.942  1.00  0.00           H  
HETATM   52  H7  UNL     1       8.459  -0.193  -1.721  1.00  0.00           H  
HETATM   53  H8  UNL     1       1.902   0.864  -2.282  1.00  0.00           H  
HETATM   54  H9  UNL     1       1.825  -0.955  -2.511  1.00  0.00           H  
HETATM   55  H10 UNL     1       1.289   0.701   0.019  1.00  0.00           H  
HETATM   56  H11 UNL     1      -0.862   0.514   0.851  1.00  0.00           H  
HETATM   57  H12 UNL     1      -2.153   1.887   1.402  1.00  0.00           H  
HETATM   58  H13 UNL     1      -2.316   4.642   3.304  1.00  0.00           H  
HETATM   59  H14 UNL     1      -4.589   5.440   3.242  1.00  0.00           H  
HETATM   60  H15 UNL     1      -7.586   5.091   3.307  1.00  0.00           H  
HETATM   61  H16 UNL     1      -7.350   3.153   0.872  1.00  0.00           H  
HETATM   62  H17 UNL     1      -3.337  -1.617  -1.420  1.00  0.00           H  
HETATM   63  H18 UNL     1      -4.379  -4.263  -3.556  1.00  0.00           H  
HETATM   64  H19 UNL     1      -7.591  -3.668  -3.980  1.00  0.00           H  
HETATM   65  H20 UNL     1      -8.780  -2.265  -3.303  1.00  0.00           H  
HETATM   66  H21 UNL     1      -7.221   0.155  -1.188  1.00  0.00           H  
HETATM   67  H22 UNL     1      -1.030  -2.493   0.316  1.00  0.00           H  
HETATM   68  H23 UNL     1      -1.489  -1.006   2.700  1.00  0.00           H  
HETATM   69  H24 UNL     1       0.611  -0.569   2.042  1.00  0.00           H  
HETATM   70  H25 UNL     1       0.131  -2.819   2.840  1.00  0.00           H  
HETATM   71  H26 UNL     1       1.255  -2.327  -0.348  1.00  0.00           H  
HETATM   72  H27 UNL     1       2.980  -1.096   1.502  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   46
CONECT    4    5   47
CONECT    5    6    6   12
CONECT    6    7   48
CONECT    7    8    8   49
CONECT    8    9   10
CONECT    9   50
CONECT   10   11   12   12
CONECT   11   51
CONECT   12   52
CONECT   13   14
CONECT   14   15   53   54
CONECT   15   16   44   55
CONECT   16   17
CONECT   17   18   40   56
CONECT   18   19
CONECT   19   20   20   30
CONECT   20   21   57
CONECT   21   22   22   28
CONECT   22   23   24
CONECT   23   58
CONECT   24   25   25   59
CONECT   25   26   27
CONECT   26   60
CONECT   27   28   28   61
CONECT   28   29
CONECT   29   30   30
CONECT   30   31
CONECT   31   32   32   39
CONECT   32   33   62
CONECT   33   34   35   35
CONECT   34   63
CONECT   35   36   37
CONECT   36   64
CONECT   37   38   39   39
CONECT   38   65
CONECT   39   66
CONECT   40   41   42   67
CONECT   41   68
CONECT   42   43   44   69
CONECT   43   70
CONECT   44   45   71
CONECT   45   72
END

HMDB0301899
     RDKit          3D
Delphinidin 3-caffeoylglucoside
 72 76  0  0  0  0  0  0  0  0999 V2000
    4.1764   -0.1011   -3.3716 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135   -0.1465   -2.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7938   -0.1663   -1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0484   -0.2082   -0.3958 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3924   -0.2310    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5691   -0.2672    1.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8316   -0.2902    2.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9581   -0.2794    1.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2105   -0.3049    1.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8068   -0.2440   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9189   -0.2322   -0.9474 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5137   -0.2204   -0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3304   -0.1747   -1.2877 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9836   -0.1487   -1.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0748   -0.2027   -0.5857 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2607   -0.1629   -0.9202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1185   -0.3034    0.1526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4605   -0.2286   -0.1753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.6517    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1355    1.7319    1.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093    2.6207    1.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    3.7074    2.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5479    3.8686    2.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189    4.6069    2.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0840    4.3895    2.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0644    5.2986    2.4640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3576    3.3248    1.2642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3715    2.4090    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6081    1.4135    0.1203 O   0  0  0  0  0  3  0  0  0  0  0  0
   -4.7186    0.4935   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1816   -0.5640   -1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3898   -1.5462   -1.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8721   -2.5563   -2.4828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267   -3.5350   -2.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2070   -2.5636   -2.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6446   -3.5933   -3.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0343   -1.5811   -2.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3660   -1.5789   -2.7105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5120   -0.5868   -1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8947   -1.5862    0.9193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7626   -1.6398    1.9953 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5281   -1.5186    1.4747 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8681   -2.6403    2.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319   -1.3966    0.2685 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7803   -1.4183    0.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020   -0.1467   -2.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2212   -0.2261    0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6946   -0.2755    2.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -0.3192    3.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0363   -0.2975    1.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8801   -0.2073   -1.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4590   -0.1928   -1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9020    0.8639   -2.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246   -0.9553   -2.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2889    0.7007    0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8621    0.5135    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526    1.8873    1.4023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    4.6417    3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5894    5.4398    3.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5860    5.0908    3.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500    3.1534    0.8719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3369   -1.6175   -1.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3786   -4.2630   -3.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5906   -3.6683   -3.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7804   -2.2653   -3.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2211    0.1550   -1.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297   -2.4931    0.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4888   -1.0055    2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6105   -0.5694    2.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311   -2.8192    2.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549   -2.3271   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800   -1.0959    1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 17 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 12  5  1  0
 44 15  1  0
 30 19  1  0
 39 31  1  0
 28 21  1  0
  3 46  1  0
  4 47  1  0
  6 48  1  0
  7 49  1  0
  9 50  1  0
 11 51  1  0
 12 52  1  0
 14 53  1  0
 14 54  1  0
 15 55  1  1
 17 56  1  1
 20 57  1  0
 23 58  1  0
 24 59  1  0
 26 60  1  0
 27 61  1  0
 32 62  1  0
 34 63  1  0
 36 64  1  0
 38 65  1  0
 39 66  1  0
 40 67  1  6
 41 68  1  0
 42 69  1  1
 43 70  1  0
 44 71  1  6
 45 72  1  0
M  CHG  1  29   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₀H₂₇O₁₅

Average Molecular Weight

627.5264

Monoisotopic Molecular Weight

627.134995194

IUPAC Name

3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

Traditional Name

3-{[(2S,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=O)\C=C\C2=CC(O)=C(O)C=C2)O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C30H26O15/c31-14-8-17(33)15-10-22(29(43-21(15)9-14)13-6-19(35)25(38)20(36)7-13)44-30-28(41)27(40)26(39)23(45-30)11-42-24(37)4-2-12-1-3-16(32)18(34)5-12/h1-10,23,26-28,30,39-41H,11H2,(H6-,31,32,33,34,35,36,37,38)/p+1/t23-,26-,27+,28-,30-/m1/s1

InChI Key

CPESTIBYQUOXSA-LHRGPQAGSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin 3-O-6-p-coumaroyl glycosides

Alternative Parents

Substituents

Anthocyanidin 3-o-6-p-coumaroyl-glycoside
Anthocyanidin-3-o-glycoside
Anthocyanin
Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Hydroxycinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Pyrogallol derivative
Benzenetriol
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthocyanidin glycoside (CHEBI:80474 )
Anthocyanidins (C16367 )
Anthocyanidins and anthocyanins (C16367 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301899)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

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	2.85	ALOGPS
logP	3.23	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	260.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	161.77 m³·mol⁻¹	ChemAxon
Polarizability	61.07 Å³	ChemAxon
Number of Rings	5	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
AllCCS	[M+H]+	237.553	32859911
AllCCS	[M+H-H2O]+	236.412	32859911
AllCCS	[M+Na]+	238.859	32859911
AllCCS	[M+NH4]+	238.573	32859911
AllCCS	[M-H]-	231.745	32859911
AllCCS	[M+Na-2H]-	233.753	32859911
AllCCS	[M+HCOO]-	236.098	32859911
DeepCCS	[M+H]+	234.873	30932474
DeepCCS	[M-H]-	232.971	30932474
DeepCCS	[M-2H]-	266.379	30932474
DeepCCS	[M+Na]+	240.786	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Delphinidin 3-caffeoylglucoside,3TMS,isomer #86	C[Si](C)(C)OC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[C@@H]2O[C@H](COC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC(O)=C1O	5682.7	Semi standard non polar	33892256
Delphinidin 3-caffeoylglucoside,3TMS,isomer #86	C[Si](C)(C)OC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[C@@H]2O[C@H](COC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC(O)=C1O	5516.0	Standard non polar	33892256
Delphinidin 3-caffeoylglucoside,3TMS,isomer #86	C[Si](C)(C)OC1=CC(C2=[O+]C3=CC(O)=CC(O)=C3C=C2O[C@@H]2O[C@H](COC(=O)/C=C/C3=CC=C(O)C(O)=C3)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC(O)=C1O	7454.8	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Delphinidin 3-caffeoylglucoside 10V, Positive-QTOF	splash10-004i-0000009000-8a94407bd2bba4d2ab26	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Delphinidin 3-caffeoylglucoside 20V, Positive-QTOF	splash10-000i-0000009000-607a71afb6ecaebdb575	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Delphinidin 3-caffeoylglucoside 40V, Positive-QTOF	splash10-0171-0923016000-31eebb6cd79999d81a6f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Delphinidin 3-caffeoylglucoside 10V, Negative-QTOF	splash10-004i-0000009000-2c35f6dfe3af6f4fadde	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Delphinidin 3-caffeoylglucoside 20V, Negative-QTOF	splash10-004i-1000009000-168e30b9e9440504cee8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Delphinidin 3-caffeoylglucoside 40V, Negative-QTOF	splash10-056r-7920001000-45839c93986a2e845596	2016-08-03	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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 Delphinidin 3-caffeoylglucoside (HMDB0301899)

MOL for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

3D MOL for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

3D SDF for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

3D-SDF for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

PDB for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

3D PDB for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

SMILES for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

INCHI for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

Structure for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

3D Structure for HMDB0301899 (Delphinidin 3-caffeoylglucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra