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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 08:56:26 UTC

Update Date

2021-09-24 08:56:26 UTC

HMDB ID

HMDB0304327

Secondary Accession Numbers

None

Metabolite Identification

Common Name

delphinidin 3-O-(6''-O-malonyl)-beta-glucoside

Description

Delphinidin 3-o-(6''-o-malonyl)-beta-glucoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Delphinidin 3-o-(6''-o-malonyl)-beta-glucoside can be found in a number of food items such as lemon, other soy product, ceylon cinnamon, and gram bean, which makes delphinidin 3-o-(6''-o-malonyl)-beta-glucoside a potential biomarker for the consumption of these food products.

Structure

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

Delphinidin 3-O-(6"-malonyl-glucoside)
  Mrv1652309231717582D          

 39 42  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0012   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2374    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 17 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 29 37  1  0  0  0  0
 15 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  CHG  1  12  -1
M  END

HMDB0304327
     RDKit          3D
delphinidin 3-O-(6''-O-malonyl)-beta-glucoside
 60 63  0  0  0  0  0  0  0  0999 V2000
    5.1660    3.6373    4.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6591    2.5137    3.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081    2.3216    4.2158 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.8509    1.4283    3.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7765    1.4472    1.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540    2.3462    1.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712    0.4707    1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    0.3951   -0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -0.8355   -0.5403 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8471   -0.8055   -0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -0.4219   -0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3765   -0.6778   -0.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497   -0.9275    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -2.2604    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9725   -2.6626    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162   -3.9342    1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426   -4.9027    1.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4503   -4.2515    2.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4688   -3.3208    2.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072   -3.6200    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2494   -2.0415    1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0384   -1.6519    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7768   -0.4705    0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -0.0618    0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912    1.3354   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    2.1008   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    3.3977   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637    4.1743   -0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    3.9162   -1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189    5.1941   -1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    3.1382   -1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.6332   -1.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.8823   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -1.1842   -2.2262 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0600   -2.5418   -1.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531   -0.7213   -2.8471 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2797    0.6618   -3.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248   -1.2391   -1.9439 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2750   -2.6370   -2.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586    0.4349    3.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    1.4686    3.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    1.3203   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9688    0.2359   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314   -1.6521    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560    0.6469   -1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -2.9636    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -4.7873    1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864   -5.2560    2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -1.2984    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5291    1.7568    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    3.8093   -0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    5.7513   -1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2450    4.5691   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7158    1.2838   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -0.9309   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -3.1022   -2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142   -1.2197   -3.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3713    0.9881   -3.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3217   -0.8579   -2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8699   -3.0213   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
 11 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38  9  1  0
 24 13  2  0
 33 25  1  0
 22 15  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 11 45  1  0
 14 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 26 50  1  0
 28 51  1  0
 30 52  1  0
 32 53  1  0
 33 54  1  0
 34 55  1  6
 35 56  1  0
 36 57  1  6
 37 58  1  0
 38 59  1  6
 39 60  1  0
M  CHG  1   3  -1
M  END

Delphinidin 3-O-(6"-malonyl-glucoside)
  Mrv1652309231717582D          

 39 42  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0012   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -1.2374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2374    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 17 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 29 37  1  0  0  0  0
 15 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  CHG  1  12  -1
M  END
> <DATABASE_ID>
HMDB0304327

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(=O)CC([O-])=O)OC(OC2=C(OC3=CC(=O)C=C(O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O15/c25-9-3-11(26)10-5-15(23(37-14(10)4-9)8-1-12(27)19(32)13(28)2-8)38-24-22(35)21(34)20(33)16(39-24)7-36-18(31)6-17(29)30/h1-5,16,20-22,24,26-28,32-35H,6-7H2,(H,29,30)/p-1/t16-,20-,21+,22-,24?/m1/s1

> <INCHI_KEY>
URVJYTCBPQJMHX-XRACCFGSSA-M

> <FORMULA>
C24H21O15

> <MOLECULAR_WEIGHT>
549.4145

> <EXACT_MASS>
549.088045002

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
50.188483343494966

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-{[5-hydroxy-7-oxo-2-(3,4,5-trihydroxyphenyl)-7H-chromen-3-yl]oxy}oxan-2-yl]methoxy}propanoate

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
-1.7235176473454703

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.390320507893656

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5520360068155337

> <JCHEM_PKA_STRONGEST_BASIC>
2.635572164824152

> <JCHEM_POLAR_SURFACE_AREA>
252.79999999999993

> <JCHEM_REFRACTIVITY>
139.59499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-3-{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-{[5-hydroxy-7-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}oxan-2-yl]methoxy}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304327
     RDKit          3D
delphinidin 3-O-(6''-O-malonyl)-beta-glucoside
 60 63  0  0  0  0  0  0  0  0999 V2000
    5.1660    3.6373    4.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6591    2.5137    3.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081    2.3216    4.2158 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.8509    1.4283    3.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7765    1.4472    1.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540    2.3462    1.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712    0.4707    1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    0.3951   -0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -0.8355   -0.5403 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8471   -0.8055   -0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -0.4219   -0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3765   -0.6778   -0.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497   -0.9275    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -2.2604    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9725   -2.6626    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162   -3.9342    1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426   -4.9027    1.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4503   -4.2515    2.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4688   -3.3208    2.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072   -3.6200    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2494   -2.0415    1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0384   -1.6519    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7768   -0.4705    0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -0.0618    0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912    1.3354   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    2.1008   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    3.3977   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637    4.1743   -0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    3.9162   -1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189    5.1941   -1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    3.1382   -1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.6332   -1.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.8823   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -1.1842   -2.2262 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0600   -2.5418   -1.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531   -0.7213   -2.8471 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2797    0.6618   -3.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248   -1.2391   -1.9439 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2750   -2.6370   -2.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586    0.4349    3.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    1.4686    3.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    1.3203   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9688    0.2359   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314   -1.6521    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560    0.6469   -1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -2.9636    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -4.7873    1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864   -5.2560    2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -1.2984    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5291    1.7568    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    3.8093   -0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    5.7513   -1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2450    4.5691   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7158    1.2838   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -0.9309   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -3.1022   -2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142   -1.2197   -3.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3713    0.9881   -3.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3217   -0.8579   -2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8699   -3.0213   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
 11 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38  9  1  0
 24 13  2  0
 33 25  1  0
 22 15  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 11 45  1  0
 14 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 26 50  1  0
 28 51  1  0
 30 52  1  0
 32 53  1  0
 33 54  1  0
 34 55  1  6
 35 56  1  0
 36 57  1  6
 37 58  1  0
 38 59  1  6
 39 60  1  0
M  CHG  1   3  -1
M  END

HEADER    PROTEIN                                 23-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Delphinidin 3-O-(6"-malonyl-glucoside)            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-SEP-17         0                                  
HETATM    1  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.338  -2.310   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0      16.004  -4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16   38                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27   17                                                       
CONECT   29   18   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29                                                       
CONECT   38   15    2   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

COMPND    HMDB0304327
HETATM    1  O1  UNL     1       5.166   3.637   4.152  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.659   2.514   3.927  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.008   2.322   4.216  1.00  0.00           O1-
HETATM    4  C2  UNL     1       4.851   1.428   3.379  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.777   1.447   1.898  1.00  0.00           C  
HETATM    6  O3  UNL     1       5.354   2.346   1.241  1.00  0.00           O  
HETATM    7  O4  UNL     1       4.071   0.471   1.243  1.00  0.00           O  
HETATM    8  C4  UNL     1       3.940   0.395  -0.185  1.00  0.00           C  
HETATM    9  C5  UNL     1       3.099  -0.835  -0.540  1.00  0.00           C  
HETATM   10  O5  UNL     1       1.847  -0.806  -0.040  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.809  -0.422  -0.880  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.377  -0.678  -0.398  1.00  0.00           O  
HETATM   13  C7  UNL     1      -1.550  -0.928   0.077  1.00  0.00           C  
HETATM   14  C8  UNL     1      -1.789  -2.260   0.558  1.00  0.00           C  
HETATM   15  C9  UNL     1      -2.972  -2.663   1.071  1.00  0.00           C  
HETATM   16  C10 UNL     1      -3.216  -3.934   1.535  1.00  0.00           C  
HETATM   17  O7  UNL     1      -2.243  -4.903   1.505  1.00  0.00           O  
HETATM   18  C11 UNL     1      -4.450  -4.252   2.039  1.00  0.00           C  
HETATM   19  C12 UNL     1      -5.469  -3.321   2.095  1.00  0.00           C  
HETATM   20  O8  UNL     1      -6.607  -3.620   2.562  1.00  0.00           O  
HETATM   21  C13 UNL     1      -5.249  -2.041   1.637  1.00  0.00           C  
HETATM   22  C14 UNL     1      -4.038  -1.652   1.119  1.00  0.00           C  
HETATM   23  O9  UNL     1      -3.777  -0.470   0.678  1.00  0.00           O  
HETATM   24  C15 UNL     1      -2.607  -0.062   0.169  1.00  0.00           C  
HETATM   25  C16 UNL     1      -2.591   1.335  -0.256  1.00  0.00           C  
HETATM   26  C17 UNL     1      -1.482   2.101  -0.352  1.00  0.00           C  
HETATM   27  C18 UNL     1      -1.597   3.398  -0.864  1.00  0.00           C  
HETATM   28  O10 UNL     1      -0.464   4.174  -0.962  1.00  0.00           O  
HETATM   29  C19 UNL     1      -2.816   3.916  -1.272  1.00  0.00           C  
HETATM   30  O11 UNL     1      -2.919   5.194  -1.775  1.00  0.00           O  
HETATM   31  C20 UNL     1      -3.946   3.138  -1.172  1.00  0.00           C  
HETATM   32  O12 UNL     1      -5.193   3.633  -1.574  1.00  0.00           O  
HETATM   33  C21 UNL     1      -3.823   1.882  -0.676  1.00  0.00           C  
HETATM   34  C22 UNL     1       0.944  -1.184  -2.226  1.00  0.00           C  
HETATM   35  O13 UNL     1       1.060  -2.542  -1.973  1.00  0.00           O  
HETATM   36  C23 UNL     1       2.253  -0.721  -2.847  1.00  0.00           C  
HETATM   37  O14 UNL     1       2.280   0.662  -3.001  1.00  0.00           O  
HETATM   38  C24 UNL     1       3.325  -1.239  -1.944  1.00  0.00           C  
HETATM   39  O15 UNL     1       3.275  -2.637  -2.025  1.00  0.00           O  
HETATM   40  H1  UNL     1       5.259   0.435   3.708  1.00  0.00           H  
HETATM   41  H2  UNL     1       3.802   1.469   3.785  1.00  0.00           H  
HETATM   42  H3  UNL     1       3.520   1.320  -0.570  1.00  0.00           H  
HETATM   43  H4  UNL     1       4.969   0.236  -0.565  1.00  0.00           H  
HETATM   44  H5  UNL     1       3.631  -1.652   0.081  1.00  0.00           H  
HETATM   45  H6  UNL     1       0.956   0.647  -1.223  1.00  0.00           H  
HETATM   46  H7  UNL     1      -0.974  -2.964   0.500  1.00  0.00           H  
HETATM   47  H8  UNL     1      -1.316  -4.787   1.162  1.00  0.00           H  
HETATM   48  H9  UNL     1      -4.686  -5.256   2.418  1.00  0.00           H  
HETATM   49  H10 UNL     1      -6.055  -1.298   1.679  1.00  0.00           H  
HETATM   50  H11 UNL     1      -0.529   1.757   0.004  1.00  0.00           H  
HETATM   51  H12 UNL     1       0.429   3.809  -0.671  1.00  0.00           H  
HETATM   52  H13 UNL     1      -2.081   5.751  -1.840  1.00  0.00           H  
HETATM   53  H14 UNL     1      -5.245   4.569  -1.939  1.00  0.00           H  
HETATM   54  H15 UNL     1      -4.716   1.284  -0.605  1.00  0.00           H  
HETATM   55  H16 UNL     1       0.064  -0.931  -2.815  1.00  0.00           H  
HETATM   56  H17 UNL     1       0.555  -3.102  -2.611  1.00  0.00           H  
HETATM   57  H18 UNL     1       2.314  -1.220  -3.844  1.00  0.00           H  
HETATM   58  H19 UNL     1       1.371   0.988  -3.214  1.00  0.00           H  
HETATM   59  H20 UNL     1       4.322  -0.858  -2.257  1.00  0.00           H  
HETATM   60  H21 UNL     1       3.870  -3.021  -1.322  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5   40   41
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   42   43
CONECT    9   10   38   44
CONECT   10   11
CONECT   11   12   34   45
CONECT   12   13
CONECT   13   14   24   24
CONECT   14   15   15   46
CONECT   15   16   22
CONECT   16   17   18   18
CONECT   17   47
CONECT   18   19   48
CONECT   19   20   20   21
CONECT   21   22   22   49
CONECT   22   23
CONECT   23   24
CONECT   24   25
CONECT   25   26   26   33
CONECT   26   27   50
CONECT   27   28   29   29
CONECT   28   51
CONECT   29   30   31
CONECT   30   52
CONECT   31   32   33   33
CONECT   32   53
CONECT   33   54
CONECT   34   35   36   55
CONECT   35   56
CONECT   36   37   38   57
CONECT   37   58
CONECT   38   39   59
CONECT   39   60
END

HMDB0304327
     RDKit          3D
delphinidin 3-O-(6''-O-malonyl)-beta-glucoside
 60 63  0  0  0  0  0  0  0  0999 V2000
    5.1660    3.6373    4.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6591    2.5137    3.9271 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081    2.3216    4.2158 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.8509    1.4283    3.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7765    1.4472    1.8978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3540    2.3462    1.2415 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712    0.4707    1.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    0.3951   -0.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -0.8355   -0.5403 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8471   -0.8055   -0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8090   -0.4219   -0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3765   -0.6778   -0.3985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5497   -0.9275    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -2.2604    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9725   -2.6626    1.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162   -3.9342    1.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426   -4.9027    1.5046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4503   -4.2515    2.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4688   -3.3208    2.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6072   -3.6200    2.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2494   -2.0415    1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0384   -1.6519    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7768   -0.4705    0.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6073   -0.0618    0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912    1.3354   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4825    2.1008   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    3.3977   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4637    4.1743   -0.9625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8162    3.9162   -1.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189    5.1941   -1.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    3.1382   -1.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.6332   -1.5739 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.8823   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9442   -1.1842   -2.2262 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0600   -2.5418   -1.9727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531   -0.7213   -2.8471 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2797    0.6618   -3.0007 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3248   -1.2391   -1.9439 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2750   -2.6370   -2.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2586    0.4349    3.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019    1.4686    3.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    1.3203   -0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9688    0.2359   -0.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314   -1.6521    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560    0.6469   -1.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9740   -2.9636    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -4.7873    1.1622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6864   -5.2560    2.4178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0552   -1.2984    1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5291    1.7568    0.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4290    3.8093   -0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0807    5.7513   -1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2450    4.5691   -1.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7158    1.2838   -0.6048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0641   -0.9309   -2.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -3.1022   -2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142   -1.2197   -3.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3713    0.9881   -3.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3217   -0.8579   -2.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8699   -3.0213   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  2  0
 11 34  1  0
 34 35  1  0
 34 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 38  9  1  0
 24 13  2  0
 33 25  1  0
 22 15  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  1
 11 45  1  0
 14 46  1  0
 17 47  1  0
 18 48  1  0
 21 49  1  0
 26 50  1  0
 28 51  1  0
 30 52  1  0
 32 53  1  0
 33 54  1  0
 34 55  1  6
 35 56  1  0
 36 57  1  6
 37 58  1  0
 38 59  1  6
 39 60  1  0
M  CHG  1   3  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-{[(3R,4S,5S,6R)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-oxo-2-(3,4,5-trihydroxyphenyl)-7H-chromen-5-olic acid	Generator

Chemical Formula

C₂₄H₂₁O₁₅

Average Molecular Weight

549.4145

Monoisotopic Molecular Weight

549.088045002

IUPAC Name

3-oxo-3-{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-{[5-hydroxy-7-oxo-2-(3,4,5-trihydroxyphenyl)-7H-chromen-3-yl]oxy}oxan-2-yl]methoxy}propanoate

Traditional Name

3-oxo-3-{[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-{[5-hydroxy-7-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}oxan-2-yl]methoxy}propanoate

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(=O)CC([O-])=O)OC(OC2=C(OC3=CC(=O)C=C(O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C24H22O15/c25-9-3-11(26)10-5-15(23(37-14(10)4-9)8-1-12(27)19(32)13(28)2-8)38-24-22(35)21(34)20(33)16(39-24)7-36-18(31)6-17(29)30/h1-5,16,20-22,24,26-28,32-35H,6-7H2,(H,29,30)/p-1/t16-,20-,21+,22-,24?/m1/s1

InChI Key

URVJYTCBPQJMHX-XRACCFGSSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Plumeran-type alkaloids

Sub Class

Not Available

Direct Parent

Plumeran-type alkaloids

Alternative Parents

Substituents

Plumeran-type alkaloid
Carbazole
Indole or derivatives
Anisole
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Alkyl aryl ether
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Cyclic alcohol
Methyl ester
Tertiary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid ester
Amino acid or derivatives
Carboxylic acid derivative
Azacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	1.22	ALOGPS
logP	-1.7	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	2.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	252.8 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139.6 m³·mol⁻¹	ChemAxon
Polarizability	50.19 Å³	ChemAxon
Number of Rings	4	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]+	218.202	32859911
AllCCS	[M+H-H2O]+	216.502	32859911
AllCCS	[M+Na]+	220.186	32859911
AllCCS	[M+NH4]+	219.748	32859911
AllCCS	[M-H]-	215.4	32859911
AllCCS	[M+Na-2H]-	216.576	32859911
AllCCS	[M+HCOO]-	218.018	32859911
DeepCCS	[M+H]+	211.734	30932474
DeepCCS	[M-H]-	209.621	30932474
DeepCCS	[M-2H]-	242.858	30932474
DeepCCS	[M+Na]+	217.642	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 - delphinidin 3-O-(6''-O-malonyl)-beta-glucoside 10V, Negative-QTOF	splash10-053r-9514170000-d8501d57dc3e1d7f61e4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delphinidin 3-O-(6''-O-malonyl)-beta-glucoside 20V, Negative-QTOF	splash10-0f89-9226130000-a92e20046255132138a9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delphinidin 3-O-(6''-O-malonyl)-beta-glucoside 40V, Negative-QTOF	splash10-0ue9-6889000000-8cf54d284b1aa3ed951f	2019-02-23	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

FDB030808

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

25244104

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-O-(6''-O-malonyl)-beta-glucoside (HMDB0304327)

MOL for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

3D MOL for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

3D SDF for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

3D-SDF for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

PDB for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

3D PDB for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

SMILES for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

INCHI for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

Structure for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

3D Structure for HMDB0304327 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra