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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 03:39:40 UTC

Update Date

2021-09-24 03:39:40 UTC

HMDB ID

HMDB0303662

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Procyanidin C2

Description

Procyanidin c2, also known as C-(4,8)-C-(4,8)-C or procyanidin trimer c2, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Procyanidin c2 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Procyanidin c2 can be found in barley, beer, and common grape, which makes procyanidin c2 a potential biomarker for the consumption of these food products.

Structure

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

Procyanidin trimer C2
  Mrv1572001071617292D          

 63 71  0  0  1  0            999 V2000
   17.8020  -18.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3784  -15.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2257  -21.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2310  -20.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3730  -21.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9441  -18.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8073  -17.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3678  -21.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9493  -18.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7967  -24.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6547  -23.4877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5204  -15.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3744  -19.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3744  -17.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9507  -15.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9507  -14.3481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7980  -22.2501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7981  -20.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0875  -19.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0875  -19.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8020  -20.3616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3730  -18.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3784  -17.2356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7967  -21.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5165  -19.9491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5165  -19.1241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.6639  -16.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3730  -20.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5112  -22.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6586  -19.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0929  -16.8231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0822  -22.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6639  -15.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5112  -23.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6586  -19.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0929  -15.9981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2310  -18.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9494  -17.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7967  -23.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0822  -23.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9402  -22.2501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8073  -15.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2257  -23.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9494  -15.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9402  -23.0751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2349  -16.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2349  -15.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9455  -19.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2310  -17.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6547  -21.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5218  -15.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6599  -18.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8073  -14.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9455  -17.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6599  -17.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2363  -15.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3692  -22.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6547  -21.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5218  -14.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2363  -14.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0836  -21.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3692  -20.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0836  -21.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1 26  1  0  0  0  0
  2 33  1  0  0  0  0
  2 36  1  0  0  0  0
  3 29  1  0  0  0  0
  3 41  1  0  0  0  0
 25  4  1  1  0  0  0
  5 28  1  0  0  0  0
  6 30  1  0  0  0  0
 31  7  1  1  0  0  0
  8 32  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 45 11  1  1  0  0  0
 12 47  1  0  0  0  0
 13 52  1  0  0  0  0
 14 55  1  0  0  0  0
 15 56  1  0  0  0  0
 16 60  1  0  0  0  0
 17 61  1  0  0  0  0
 18 63  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 28  2  0  0  0  0
 20 22  2  0  0  0  0
 21 24  1  6  0  0  0
 21 25  1  0  0  0  0
 23 22  1  6  0  0  0
 22 30  1  0  0  0  0
 23 27  1  0  0  0  0
 23 31  1  0  0  0  0
 24 29  2  0  0  0  0
 24 32  1  0  0  0  0
 25 26  1  0  0  0  0
 26 37  1  6  0  0  0
 27 33  1  0  0  0  0
 27 38  2  0  0  0  0
 28 35  1  0  0  0  0
 29 34  1  0  0  0  0
 30 35  2  0  0  0  0
 31 36  1  0  0  0  0
 32 40  2  0  0  0  0
 33 44  2  0  0  0  0
 34 39  2  0  0  0  0
 34 43  1  0  0  0  0
 36 42  1  6  0  0  0
 37 48  2  0  0  0  0
 37 49  1  0  0  0  0
 38 46  1  0  0  0  0
 39 40  1  0  0  0  0
 41 45  1  0  0  0  0
 41 50  1  6  0  0  0
 42 51  2  0  0  0  0
 42 53  1  0  0  0  0
 43 45  1  0  0  0  0
 44 47  1  0  0  0  0
 46 47  2  0  0  0  0
 48 52  1  0  0  0  0
 49 54  2  0  0  0  0
 50 57  2  0  0  0  0
 50 58  1  0  0  0  0
 51 56  1  0  0  0  0
 52 55  2  0  0  0  0
 53 59  2  0  0  0  0
 54 55  1  0  0  0  0
 56 60  2  0  0  0  0
 57 61  1  0  0  0  0
 58 62  2  0  0  0  0
 59 60  1  0  0  0  0
 61 63  2  0  0  0  0
 62 63  1  0  0  0  0
M  END

HMDB0303662
     RDKit          3D
Procyanidin C2
101109  0  0  0  0  0  0  0  0999 V2000
    3.2705   -5.2474   -2.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596   -3.9728   -1.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762   -3.6310   -1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5343   -2.3725   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407   -2.0698   -0.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -1.4208   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861   -1.7792   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595   -3.0452   -1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862   -0.8329   -0.8034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057    0.0921    0.2332 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7984   -0.3770    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923    0.4938    1.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6407    0.0523    2.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6795   -1.2661    3.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6355   -1.7139    4.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7849   -2.1588    2.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8738   -3.4785    2.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -1.6993    1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4685    0.4116    0.8439 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3565    1.8211    0.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267   -0.0512   -0.0002 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9993    0.1745    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -0.3369    1.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.0518    2.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238   -0.1261    2.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5675    0.5793    1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8663    0.7822    2.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2159    1.0716    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376    0.8857   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    1.4329   -1.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    2.7632   -1.6788 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9464    3.7027   -1.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2681    3.4166   -1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3263    4.2447   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    5.4116   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1678    6.2484   -0.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224    5.7279   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6021    6.8990    0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    4.8676   -0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4059    3.0646   -0.8728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1554    4.0390   -1.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275    1.8140   -0.5186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4997    1.8750   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    2.9893    0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766    4.0832    0.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2977    3.0448    0.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1629    1.9752    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4843    2.0538    1.0863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6736    0.8914    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3361    0.8128   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -0.3644   -1.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -1.5801   -0.4604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2990   -2.7308   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0811   -2.5882   -2.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0082   -3.7275   -3.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484   -4.9909   -2.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -6.1328   -3.8066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -5.1441   -1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086   -6.3973   -1.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384   -3.9899   -0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7836   -1.5227    0.1203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7264   -1.4537    1.5418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5389   -0.2906   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1946   -5.5121   -3.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -4.3866   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5069   -2.7359   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474   -3.3320   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2419    1.0379   -0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7335    1.5452    1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3369    0.7444    3.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871   -2.6813    4.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2693   -4.2186    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1679   -2.4043    1.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963    0.0651    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2699    2.1987    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.5978   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130   -1.4125    3.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -0.5103    3.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0692    0.4061    3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    2.8081   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721    2.5206   -2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424    4.0272   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0482    7.1012    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919    7.2070    0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1929    5.1848   -0.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557    3.5000    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5306    4.5037   -2.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183    1.1929   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    4.9012    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379    3.8888    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8224    2.8705    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7297   -1.8587    0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -1.5947   -3.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8383   -3.6470   -4.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -7.0453   -3.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6733   -6.5046   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6198   -4.1597    0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3356   -2.4519   -0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8015   -1.5503    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4884   -0.1660    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7707   -0.3068   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 10 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37 39  2  0
 31 40  1  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 44 46  1  0
 46 47  2  0
 47 48  1  0
 47 49  1  0
 49 50  2  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  2  0
 54 55  1  0
 55 56  2  0
 56 57  1  0
 56 58  1  0
 58 59  1  0
 58 60  2  0
 52 61  1  0
 61 62  1  0
 61 63  1  0
  8  2  1  0
 18 11  1  0
 29 22  1  0
 39 32  1  0
 50 43  1  0
 60 53  1  0
 21  6  1  0
 42 28  1  0
 63 49  1  0
  1 64  1  0
  3 65  1  0
  5 66  1  0
  8 67  1  0
 10 68  1  6
 12 69  1  0
 13 70  1  0
 15 71  1  0
 17 72  1  0
 18 73  1  0
 19 74  1  1
 20 75  1  0
 21 76  1  6
 24 77  1  0
 25 78  1  0
 27 79  1  0
 31 80  1  6
 33 81  1  0
 34 82  1  0
 36 83  1  0
 38 84  1  0
 39 85  1  0
 40 86  1  1
 41 87  1  0
 42 88  1  6
 45 89  1  0
 46 90  1  0
 48 91  1  0
 52 92  1  1
 54 93  1  0
 55 94  1  0
 57 95  1  0
 59 96  1  0
 60 97  1  0
 61 98  1  1
 62 99  1  0
 63100  1  0
 63101  1  0
M  END

Procyanidin trimer C2
  Mrv1572001071617292D          

 63 71  0  0  1  0            999 V2000
   17.8020  -18.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3784  -15.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2257  -21.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2310  -20.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3730  -21.1866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9441  -18.7116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8073  -17.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3678  -21.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9493  -18.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7967  -24.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6547  -23.4877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5204  -15.5856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3744  -19.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3744  -17.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9507  -15.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9507  -14.3481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7980  -22.2501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7981  -20.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0875  -19.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0875  -19.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8020  -20.3616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3730  -18.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3784  -17.2356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.7967  -21.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5165  -19.9491    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.5165  -19.1241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.6639  -16.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3730  -20.3616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5112  -22.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6586  -19.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0929  -16.8231    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0822  -22.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6639  -15.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5112  -23.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6586  -19.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0929  -15.9981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.2310  -18.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9494  -17.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7967  -23.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0822  -23.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9402  -22.2501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8073  -15.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2257  -23.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9494  -15.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9402  -23.0751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.2349  -16.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2349  -15.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9455  -19.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2310  -17.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6547  -21.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5218  -15.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6599  -18.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8073  -14.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9455  -17.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6599  -17.8866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2363  -15.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3692  -22.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6547  -21.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5218  -14.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2363  -14.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0836  -21.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3692  -20.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0836  -21.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1 26  1  0  0  0  0
  2 33  1  0  0  0  0
  2 36  1  0  0  0  0
  3 29  1  0  0  0  0
  3 41  1  0  0  0  0
 25  4  1  1  0  0  0
  5 28  1  0  0  0  0
  6 30  1  0  0  0  0
 31  7  1  1  0  0  0
  8 32  1  0  0  0  0
  9 38  1  0  0  0  0
 10 39  1  0  0  0  0
 45 11  1  1  0  0  0
 12 47  1  0  0  0  0
 13 52  1  0  0  0  0
 14 55  1  0  0  0  0
 15 56  1  0  0  0  0
 16 60  1  0  0  0  0
 17 61  1  0  0  0  0
 18 63  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 28  2  0  0  0  0
 20 22  2  0  0  0  0
 21 24  1  6  0  0  0
 21 25  1  0  0  0  0
 23 22  1  6  0  0  0
 22 30  1  0  0  0  0
 23 27  1  0  0  0  0
 23 31  1  0  0  0  0
 24 29  2  0  0  0  0
 24 32  1  0  0  0  0
 25 26  1  0  0  0  0
 26 37  1  6  0  0  0
 27 33  1  0  0  0  0
 27 38  2  0  0  0  0
 28 35  1  0  0  0  0
 29 34  1  0  0  0  0
 30 35  2  0  0  0  0
 31 36  1  0  0  0  0
 32 40  2  0  0  0  0
 33 44  2  0  0  0  0
 34 39  2  0  0  0  0
 34 43  1  0  0  0  0
 36 42  1  6  0  0  0
 37 48  2  0  0  0  0
 37 49  1  0  0  0  0
 38 46  1  0  0  0  0
 39 40  1  0  0  0  0
 41 45  1  0  0  0  0
 41 50  1  6  0  0  0
 42 51  2  0  0  0  0
 42 53  1  0  0  0  0
 43 45  1  0  0  0  0
 44 47  1  0  0  0  0
 46 47  2  0  0  0  0
 48 52  1  0  0  0  0
 49 54  2  0  0  0  0
 50 57  2  0  0  0  0
 50 58  1  0  0  0  0
 51 56  1  0  0  0  0
 52 55  2  0  0  0  0
 53 59  2  0  0  0  0
 54 55  1  0  0  0  0
 56 60  2  0  0  0  0
 57 61  1  0  0  0  0
 58 62  2  0  0  0  0
 59 60  1  0  0  0  0
 61 63  2  0  0  0  0
 62 63  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303662

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1CC2=C(O)C=C(O)C([C@H]3[C@H](O)[C@H](OC4=C([C@H]5[C@H](O)[C@H](OC6=CC(O)=CC(O)=C56)C5=CC(O)=C(O)C=C5)C(O)=CC(O)=C34)C3=CC(O)=C(O)C=C3)=C2O[C@@H]1C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41+,42+,43+/m0/s1

> <INCHI_KEY>
MOJZMWJRUKIQGL-WNCKYJNFSA-N

> <FORMULA>
C45H38O18

> <MOLECULAR_WEIGHT>
866.781

> <EXACT_MASS>
866.205814384

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
86.02200987939172

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
4.436383012

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.059902703530739

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.64013483499428

> <JCHEM_PKA_STRONGEST_BASIC>
-5.195437355996721

> <JCHEM_POLAR_SURFACE_AREA>
331.14

> <JCHEM_REFRACTIVITY>
219.0163

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303662
     RDKit          3D
Procyanidin C2
101109  0  0  0  0  0  0  0  0999 V2000
    3.2705   -5.2474   -2.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596   -3.9728   -1.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762   -3.6310   -1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5343   -2.3725   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407   -2.0698   -0.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -1.4208   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861   -1.7792   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595   -3.0452   -1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862   -0.8329   -0.8034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057    0.0921    0.2332 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7984   -0.3770    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923    0.4938    1.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6407    0.0523    2.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6795   -1.2661    3.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6355   -1.7139    4.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7849   -2.1588    2.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8738   -3.4785    2.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -1.6993    1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4685    0.4116    0.8439 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3565    1.8211    0.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267   -0.0512   -0.0002 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9993    0.1745    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -0.3369    1.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.0518    2.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238   -0.1261    2.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5675    0.5793    1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8663    0.7822    2.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2159    1.0716    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376    0.8857   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    1.4329   -1.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    2.7632   -1.6788 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9464    3.7027   -1.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2681    3.4166   -1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3263    4.2447   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    5.4116   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1678    6.2484   -0.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224    5.7279   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6021    6.8990    0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    4.8676   -0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4059    3.0646   -0.8728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1554    4.0390   -1.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275    1.8140   -0.5186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4997    1.8750   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    2.9893    0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766    4.0832    0.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2977    3.0448    0.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1629    1.9752    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4843    2.0538    1.0863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6736    0.8914    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3361    0.8128   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -0.3644   -1.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -1.5801   -0.4604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2990   -2.7308   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0811   -2.5882   -2.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0082   -3.7275   -3.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484   -4.9909   -2.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -6.1328   -3.8066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -5.1441   -1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086   -6.3973   -1.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384   -3.9899   -0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7836   -1.5227    0.1203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7264   -1.4537    1.5418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5389   -0.2906   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1946   -5.5121   -3.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -4.3866   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5069   -2.7359   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474   -3.3320   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2419    1.0379   -0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2699    2.1987    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.5978   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130   -1.4125    3.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -0.5103    3.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0692    0.4061    3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    2.8081   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721    2.5206   -2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424    4.0272   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0482    7.1012    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919    7.2070    0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1929    5.1848   -0.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557    3.5000    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5306    4.5037   -2.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183    1.1929   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    4.9012    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379    3.8888    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8224    2.8705    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7297   -1.8587    0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -1.5947   -3.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8383   -3.6470   -4.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -7.0453   -3.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6733   -6.5046   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6198   -4.1597    0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3356   -2.4519   -0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8015   -1.5503    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4884   -0.1660    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7707   -0.3068   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Procyanidin trimer C2                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      33.230 -34.928   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.573 -29.093   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.888 -40.764   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      35.898 -38.008   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.563 -39.548   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      27.896 -34.928   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      33.240 -32.173   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      30.553 -40.764   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      27.905 -33.713   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      33.221 -45.384   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      38.555 -43.844   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.238 -29.093   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      39.899 -35.698   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      39.899 -32.618   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      37.241 -29.863   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      37.241 -26.783   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      42.556 -41.534   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      42.556 -38.454   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      31.897 -37.238   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.897 -35.698   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.230 -38.008   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.563 -34.928   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      30.573 -32.173   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.221 -40.764   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      34.564 -37.238   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      34.564 -35.698   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.239 -31.403   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.563 -38.008   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      34.554 -41.534   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.229 -35.698   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      31.907 -31.403   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.887 -41.534   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      29.239 -29.863   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      34.554 -43.074   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      29.229 -37.238   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.907 -29.863   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      35.898 -34.928   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      27.906 -32.173   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      33.221 -43.844   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      31.887 -43.074   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      37.222 -41.534   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      33.240 -29.093   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      35.888 -43.844   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      27.906 -29.093   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      37.222 -43.074   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      26.572 -31.403   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      26.572 -29.863   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      37.232 -35.698   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      35.898 -33.388   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      38.555 -40.764   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      34.574 -29.863   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      38.565 -34.928   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      33.240 -27.553   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      37.232 -32.618   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      38.565 -33.388   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      35.908 -29.093   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      39.889 -41.534   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      38.555 -39.224   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      34.574 -26.783   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      35.908 -27.553   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      41.223 -40.764   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      39.889 -38.454   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      41.223 -39.224   0.000  0.00  0.00           C+0
CONECT    1   20   26                                                       
CONECT    2   33   36                                                       
CONECT    3   29   41                                                       
CONECT    4   25                                                            
CONECT    5   28                                                            
CONECT    6   30                                                            
CONECT    7   31                                                            
CONECT    8   32                                                            
CONECT    9   38                                                            
CONECT   10   39                                                            
CONECT   11   45                                                            
CONECT   12   47                                                            
CONECT   13   52                                                            
CONECT   14   55                                                            
CONECT   15   56                                                            
CONECT   16   60                                                            
CONECT   17   61                                                            
CONECT   18   63                                                            
CONECT   19   20   21   28                                                  
CONECT   20    1   19   22                                                  
CONECT   21   19   24   25                                                  
CONECT   22   20   23   30                                                  
CONECT   23   22   27   31                                                  
CONECT   24   21   29   32                                                  
CONECT   25    4   21   26                                                  
CONECT   26    1   25   37                                                  
CONECT   27   23   33   38                                                  
CONECT   28    5   19   35                                                  
CONECT   29    3   24   34                                                  
CONECT   30    6   22   35                                                  
CONECT   31    7   23   36                                                  
CONECT   32    8   24   40                                                  
CONECT   33    2   27   44                                                  
CONECT   34   29   39   43                                                  
CONECT   35   28   30                                                       
CONECT   36    2   31   42                                                  
CONECT   37   26   48   49                                                  
CONECT   38    9   27   46                                                  
CONECT   39   10   34   40                                                  
CONECT   40   32   39                                                       
CONECT   41    3   45   50                                                  
CONECT   42   36   51   53                                                  
CONECT   43   34   45                                                       
CONECT   44   33   47                                                       
CONECT   45   11   41   43                                                  
CONECT   46   38   47                                                       
CONECT   47   12   44   46                                                  
CONECT   48   37   52                                                       
CONECT   49   37   54                                                       
CONECT   50   41   57   58                                                  
CONECT   51   42   56                                                       
CONECT   52   13   48   55                                                  
CONECT   53   42   59                                                       
CONECT   54   49   55                                                       
CONECT   55   14   52   54                                                  
CONECT   56   15   51   60                                                  
CONECT   57   50   61                                                       
CONECT   58   50   62                                                       
CONECT   59   53   60                                                       
CONECT   60   16   56   59                                                  
CONECT   61   17   57   63                                                  
CONECT   62   58   63                                                       
CONECT   63   18   61   62                                                  
MASTER        0    0    0    0    0    0    0    0   63    0  142    0
END

COMPND    HMDB0303662
HETATM    1  O1  UNL     1       3.270  -5.247  -2.072  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.060  -3.973  -1.562  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.776  -3.631  -1.156  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.534  -2.373  -0.645  1.00  0.00           C  
HETATM    5  O2  UNL     1       0.241  -2.070  -0.252  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.523  -1.421  -0.517  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.786  -1.779  -0.925  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.059  -3.045  -1.445  1.00  0.00           C  
HETATM    9  O3  UNL     1       4.786  -0.833  -0.803  1.00  0.00           O  
HETATM   10  C7  UNL     1       4.806   0.092   0.233  1.00  0.00           C  
HETATM   11  C8  UNL     1       5.798  -0.377   1.221  1.00  0.00           C  
HETATM   12  C9  UNL     1       6.692   0.494   1.784  1.00  0.00           C  
HETATM   13  C10 UNL     1       7.641   0.052   2.716  1.00  0.00           C  
HETATM   14  C11 UNL     1       7.679  -1.266   3.070  1.00  0.00           C  
HETATM   15  O4  UNL     1       8.636  -1.714   4.010  1.00  0.00           O  
HETATM   16  C12 UNL     1       6.785  -2.159   2.511  1.00  0.00           C  
HETATM   17  O5  UNL     1       6.874  -3.479   2.913  1.00  0.00           O  
HETATM   18  C13 UNL     1       5.853  -1.699   1.591  1.00  0.00           C  
HETATM   19  C14 UNL     1       3.469   0.412   0.844  1.00  0.00           C  
HETATM   20  O6  UNL     1       3.356   1.821   0.923  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.327  -0.051  -0.000  1.00  0.00           C  
HETATM   22  C16 UNL     1       0.999   0.175   0.573  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.653  -0.337   1.825  1.00  0.00           C  
HETATM   24  O7  UNL     1       1.599  -1.052   2.559  1.00  0.00           O  
HETATM   25  C18 UNL     1      -0.624  -0.126   2.317  1.00  0.00           C  
HETATM   26  C19 UNL     1      -1.568   0.579   1.598  1.00  0.00           C  
HETATM   27  O8  UNL     1      -2.866   0.782   2.118  1.00  0.00           O  
HETATM   28  C20 UNL     1      -1.216   1.072   0.379  1.00  0.00           C  
HETATM   29  C21 UNL     1       0.038   0.886  -0.140  1.00  0.00           C  
HETATM   30  O9  UNL     1       0.342   1.433  -1.422  1.00  0.00           O  
HETATM   31  C22 UNL     1      -0.156   2.763  -1.679  1.00  0.00           C  
HETATM   32  C23 UNL     1       0.946   3.703  -1.323  1.00  0.00           C  
HETATM   33  C24 UNL     1       2.268   3.417  -1.700  1.00  0.00           C  
HETATM   34  C25 UNL     1       3.326   4.245  -1.382  1.00  0.00           C  
HETATM   35  C26 UNL     1       3.094   5.412  -0.664  1.00  0.00           C  
HETATM   36  O10 UNL     1       4.168   6.248  -0.343  1.00  0.00           O  
HETATM   37  C27 UNL     1       1.822   5.728  -0.279  1.00  0.00           C  
HETATM   38  O11 UNL     1       1.602   6.899   0.441  1.00  0.00           O  
HETATM   39  C28 UNL     1       0.777   4.868  -0.618  1.00  0.00           C  
HETATM   40  C29 UNL     1      -1.406   3.065  -0.873  1.00  0.00           C  
HETATM   41  O12 UNL     1      -2.155   4.039  -1.507  1.00  0.00           O  
HETATM   42  C30 UNL     1      -2.128   1.814  -0.519  1.00  0.00           C  
HETATM   43  C31 UNL     1      -3.500   1.875  -0.098  1.00  0.00           C  
HETATM   44  C32 UNL     1      -3.976   2.989   0.556  1.00  0.00           C  
HETATM   45  O13 UNL     1      -3.177   4.083   0.849  1.00  0.00           O  
HETATM   46  C33 UNL     1      -5.298   3.045   0.948  1.00  0.00           C  
HETATM   47  C34 UNL     1      -6.163   1.975   0.684  1.00  0.00           C  
HETATM   48  O14 UNL     1      -7.484   2.054   1.086  1.00  0.00           O  
HETATM   49  C35 UNL     1      -5.674   0.891   0.041  1.00  0.00           C  
HETATM   50  C36 UNL     1      -4.336   0.813  -0.364  1.00  0.00           C  
HETATM   51  O15 UNL     1      -3.929  -0.364  -1.024  1.00  0.00           O  
HETATM   52  C37 UNL     1      -4.425  -1.580  -0.460  1.00  0.00           C  
HETATM   53  C38 UNL     1      -4.299  -2.731  -1.375  1.00  0.00           C  
HETATM   54  C39 UNL     1      -4.081  -2.588  -2.731  1.00  0.00           C  
HETATM   55  C40 UNL     1      -4.008  -3.728  -3.524  1.00  0.00           C  
HETATM   56  C41 UNL     1      -4.148  -4.991  -2.980  1.00  0.00           C  
HETATM   57  O16 UNL     1      -4.071  -6.133  -3.807  1.00  0.00           O  
HETATM   58  C42 UNL     1      -4.366  -5.144  -1.623  1.00  0.00           C  
HETATM   59  O17 UNL     1      -4.509  -6.397  -1.074  1.00  0.00           O  
HETATM   60  C43 UNL     1      -4.438  -3.990  -0.836  1.00  0.00           C  
HETATM   61  C44 UNL     1      -5.784  -1.523   0.120  1.00  0.00           C  
HETATM   62  O18 UNL     1      -5.726  -1.454   1.542  1.00  0.00           O  
HETATM   63  C45 UNL     1      -6.539  -0.291  -0.298  1.00  0.00           C  
HETATM   64  H1  UNL     1       3.195  -5.512  -3.032  1.00  0.00           H  
HETATM   65  H2  UNL     1       1.006  -4.387  -1.262  1.00  0.00           H  
HETATM   66  H3  UNL     1      -0.507  -2.736  -0.334  1.00  0.00           H  
HETATM   67  H4  UNL     1       5.047  -3.332  -1.770  1.00  0.00           H  
HETATM   68  H5  UNL     1       5.242   1.038  -0.211  1.00  0.00           H  
HETATM   69  H6  UNL     1       6.733   1.545   1.564  1.00  0.00           H  
HETATM   70  H7  UNL     1       8.337   0.744   3.151  1.00  0.00           H  
HETATM   71  H8  UNL     1       8.687  -2.681   4.289  1.00  0.00           H  
HETATM   72  H9  UNL     1       6.269  -4.219   2.569  1.00  0.00           H  
HETATM   73  H10 UNL     1       5.168  -2.404   1.168  1.00  0.00           H  
HETATM   74  H11 UNL     1       3.496   0.065   1.873  1.00  0.00           H  
HETATM   75  H12 UNL     1       4.270   2.199   0.953  1.00  0.00           H  
HETATM   76  H13 UNL     1       2.387   0.598  -0.934  1.00  0.00           H  
HETATM   77  H14 UNL     1       1.313  -1.412   3.472  1.00  0.00           H  
HETATM   78  H15 UNL     1      -0.929  -0.510   3.290  1.00  0.00           H  
HETATM   79  H16 UNL     1      -3.069   0.406   3.010  1.00  0.00           H  
HETATM   80  H17 UNL     1      -0.352   2.808  -2.783  1.00  0.00           H  
HETATM   81  H18 UNL     1       2.472   2.521  -2.268  1.00  0.00           H  
HETATM   82  H19 UNL     1       4.342   4.027  -1.667  1.00  0.00           H  
HETATM   83  H20 UNL     1       4.048   7.101   0.170  1.00  0.00           H  
HETATM   84  H21 UNL     1       0.692   7.207   0.765  1.00  0.00           H  
HETATM   85  H22 UNL     1      -0.193   5.185  -0.294  1.00  0.00           H  
HETATM   86  H23 UNL     1      -1.056   3.500   0.102  1.00  0.00           H  
HETATM   87  H24 UNL     1      -1.531   4.504  -2.154  1.00  0.00           H  
HETATM   88  H25 UNL     1      -2.118   1.193  -1.481  1.00  0.00           H  
HETATM   89  H26 UNL     1      -3.523   4.901   1.354  1.00  0.00           H  
HETATM   90  H27 UNL     1      -5.738   3.889   1.467  1.00  0.00           H  
HETATM   91  H28 UNL     1      -7.822   2.871   1.559  1.00  0.00           H  
HETATM   92  H29 UNL     1      -3.730  -1.859   0.418  1.00  0.00           H  
HETATM   93  H30 UNL     1      -3.968  -1.595  -3.150  1.00  0.00           H  
HETATM   94  H31 UNL     1      -3.838  -3.647  -4.585  1.00  0.00           H  
HETATM   95  H32 UNL     1      -4.180  -7.045  -3.381  1.00  0.00           H  
HETATM   96  H33 UNL     1      -4.673  -6.505  -0.066  1.00  0.00           H  
HETATM   97  H34 UNL     1      -4.620  -4.160   0.239  1.00  0.00           H  
HETATM   98  H35 UNL     1      -6.336  -2.452  -0.161  1.00  0.00           H  
HETATM   99  H36 UNL     1      -4.801  -1.550   1.847  1.00  0.00           H  
HETATM  100  H37 UNL     1      -7.488  -0.166   0.233  1.00  0.00           H  
HETATM  101  H38 UNL     1      -6.771  -0.307  -1.394  1.00  0.00           H  
CONECT    1    2   64
CONECT    2    3    3    8
CONECT    3    4   65
CONECT    4    5    6    6
CONECT    5   66
CONECT    6    7   21
CONECT    7    8    8    9
CONECT    8   67
CONECT    9   10
CONECT   10   11   19   68
CONECT   11   12   12   18
CONECT   12   13   69
CONECT   13   14   14   70
CONECT   14   15   16
CONECT   15   71
CONECT   16   17   18   18
CONECT   17   72
CONECT   18   73
CONECT   19   20   21   74
CONECT   20   75
CONECT   21   22   76
CONECT   22   23   23   29
CONECT   23   24   25
CONECT   24   77
CONECT   25   26   26   78
CONECT   26   27   28
CONECT   27   79
CONECT   28   29   29   42
CONECT   29   30
CONECT   30   31
CONECT   31   32   40   80
CONECT   32   33   33   39
CONECT   33   34   81
CONECT   34   35   35   82
CONECT   35   36   37
CONECT   36   83
CONECT   37   38   39   39
CONECT   38   84
CONECT   39   85
CONECT   40   41   42   86
CONECT   41   87
CONECT   42   43   88
CONECT   43   44   44   50
CONECT   44   45   46
CONECT   45   89
CONECT   46   47   47   90
CONECT   47   48   49
CONECT   48   91
CONECT   49   50   50   63
CONECT   50   51
CONECT   51   52
CONECT   52   53   61   92
CONECT   53   54   54   60
CONECT   54   55   93
CONECT   55   56   56   94
CONECT   56   57   58
CONECT   57   95
CONECT   58   59   60   60
CONECT   59   96
CONECT   60   97
CONECT   61   62   63   98
CONECT   62   99
CONECT   63  100  101
END

HMDB0303662
     RDKit          3D
Procyanidin C2
101109  0  0  0  0  0  0  0  0999 V2000
    3.2705   -5.2474   -2.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0596   -3.9728   -1.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762   -3.6310   -1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5343   -2.3725   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2407   -2.0698   -0.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -1.4208   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7861   -1.7792   -0.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0595   -3.0452   -1.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862   -0.8329   -0.8034 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8057    0.0921    0.2332 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7984   -0.3770    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923    0.4938    1.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6407    0.0523    2.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6795   -1.2661    3.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6355   -1.7139    4.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7849   -2.1588    2.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8738   -3.4785    2.9125 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -1.6993    1.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4685    0.4116    0.8439 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3565    1.8211    0.9230 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3267   -0.0512   -0.0002 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9993    0.1745    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -0.3369    1.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.0518    2.5592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6238   -0.1261    2.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5675    0.5793    1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8663    0.7822    2.1182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2159    1.0716    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376    0.8857   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420    1.4329   -1.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    2.7632   -1.6788 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9464    3.7027   -1.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2681    3.4166   -1.6996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3263    4.2447   -1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    5.4116   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1678    6.2484   -0.3429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8224    5.7279   -0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6021    6.8990    0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766    4.8676   -0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4059    3.0646   -0.8728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1554    4.0390   -1.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275    1.8140   -0.5186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4997    1.8750   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758    2.9893    0.5564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1766    4.0832    0.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2977    3.0448    0.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1629    1.9752    0.6844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4843    2.0538    1.0863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6736    0.8914    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3361    0.8128   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9285   -0.3644   -1.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -1.5801   -0.4604 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2990   -2.7308   -1.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0811   -2.5882   -2.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0082   -3.7275   -3.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1484   -4.9909   -2.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -6.1328   -3.8066 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -5.1441   -1.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5086   -6.3973   -1.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4384   -3.9899   -0.8362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7836   -1.5227    0.1203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7264   -1.4537    1.5418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5389   -0.2906   -0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1946   -5.5121   -3.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065   -4.3866   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5069   -2.7359   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474   -3.3320   -1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2419    1.0379   -0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7335    1.5452    1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3369    0.7444    3.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6871   -2.6813    4.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2693   -4.2186    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1679   -2.4043    1.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4963    0.0651    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2699    2.1987    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.5978   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3130   -1.4125    3.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9287   -0.5103    3.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0692    0.4061    3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3518    2.8081   -2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721    2.5206   -2.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3424    4.0272   -1.6668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0482    7.1012    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919    7.2070    0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1929    5.1848   -0.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0557    3.5000    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5306    4.5037   -2.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1183    1.1929   -1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    4.9012    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7379    3.8888    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8224    2.8705    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7297   -1.8587    0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9677   -1.5947   -3.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8383   -3.6470   -4.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -7.0453   -3.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6733   -6.5046   -0.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6198   -4.1597    0.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3356   -2.4519   -0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8015   -1.5503    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4884   -0.1660    0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7707   -0.3068   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
C-(4,8)-C-(4,8)-C	ChEBI
Catechin-(4alpha->8)-catechin-(4alpha->8)-catechin	ChEBI
Procyanidin trimer C2	ChEBI
Catechin-(4a->8)-catechin-(4a->8)-catechin	Generator
Catechin-(4α->8)-catechin-(4α->8)-catechin	Generator

Chemical Formula

C₄₅H₃₈O₁₈

Average Molecular Weight

866.781

Monoisotopic Molecular Weight

866.205814384

IUPAC Name

(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O)C=C(O)C([C@H]3[C@H](O)[C@H](OC4=C([C@H]5[C@H](O)[C@H](OC6=CC(O)=CC(O)=C56)C5=CC(O)=C(O)C=C5)C(O)=CC(O)=C34)C3=CC(O)=C(O)C=C3)=C2O[C@@H]1C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41+,42+,43+/m0/s1

InChI Key

MOJZMWJRUKIQGL-WNCKYJNFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

C-type proanthocyanidin
B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:75644 )
proanthocyanidin (CHEBI:75644 )
hydroxyflavan (CHEBI:75644 )

Ontology

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	3.38	ALOGPS
logP	4.44	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	331.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	219.02 m³·mol⁻¹	ChemAxon
Polarizability	86.02 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	284.232	32859911
AllCCS	[M+H-H2O]+	284.107	32859911
AllCCS	[M+Na]+	284.318	32859911
AllCCS	[M+NH4]+	284.305	32859911
AllCCS	[M-H]-	277.878	32859911
AllCCS	[M+Na-2H]-	282.483	32859911
AllCCS	[M+HCOO]-	287.61	32859911
DeepCCS	[M-2H]-	319.433	30932474
DeepCCS	[M+Na]+	293.405	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 - Procyanidin C2 10V, Positive-QTOF	splash10-014j-0100005690-161c67165e6b61ef57bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 20V, Positive-QTOF	splash10-0005-0100095720-02cbe7a0c9e7f5b22731	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 40V, Positive-QTOF	splash10-005a-0000091310-a37ac8e1536b30e63a1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 10V, Negative-QTOF	splash10-014i-0000000290-d007b6b11a94570a4ea1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 20V, Negative-QTOF	splash10-0f79-0940310530-208f53a241f13af95f6b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 40V, Negative-QTOF	splash10-002r-0970202200-0b6a6c3437423c0f510f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 10V, Positive-QTOF	splash10-014i-0000130390-0956f39193d04ffc022e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 20V, Positive-QTOF	splash10-014j-0230010790-e4739b7dfc06a8ce85c5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 40V, Positive-QTOF	splash10-0gb9-0702021980-2dff9a9ac18d44e0dcb2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 10V, Negative-QTOF	splash10-014i-0000000090-0a49232c23c9595472be	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 20V, Negative-QTOF	splash10-0ap0-0000000490-74cc1981148d556d0a67	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Procyanidin C2 40V, Negative-QTOF	splash10-05br-0420110590-f1ef9f8f904ea2b36f4b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017715

KNApSAcK ID

C00009091

Chemspider ID

9357147

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Procyanidin_C2

METLIN ID

Not Available

PubChem Compound

11182062

PDB ID

Not Available

ChEBI ID

75644

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 Procyanidin C2 (HMDB0303662)

MOL for HMDB0303662 (Procyanidin C2)

3D MOL for HMDB0303662 (Procyanidin C2)

3D SDF for HMDB0303662 (Procyanidin C2)

3D-SDF for HMDB0303662 (Procyanidin C2)

PDB for HMDB0303662 (Procyanidin C2)

3D PDB for HMDB0303662 (Procyanidin C2)

SMILES for HMDB0303662 (Procyanidin C2)

INCHI for HMDB0303662 (Procyanidin C2)

Structure for HMDB0303662 (Procyanidin C2)

3D Structure for HMDB0303662 (Procyanidin C2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra