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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:39:01 UTC

Update Date

2022-03-07 02:55:19 UTC

HMDB ID

HMDB0037405

Secondary Accession Numbers

HMDB37405

Metabolite Identification

Common Name

8-Glucopyranosylprocyanidin B2

Description

8-Glucopyranosylprocyanidin B2 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''. 8-Glucopyranosylprocyanidin B2 has been detected, but not quantified in, a few different foods, such as chinese cinnamons (Cinnamomum aromaticum), green vegetables, and herbs and spices. This could make 8-glucopyranosylprocyanidin B2 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 8-Glucopyranosylprocyanidin B2.

Structure

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

  Mrv0541 02241208272D          

 53 59  0  0  0  0            999 V2000
    2.8359    0.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -0.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -2.0991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6925   -1.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    2.8509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    2.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925    1.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    1.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    2.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -4.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -3.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509   -2.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509   -2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654   -1.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -2.9241    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6925   -3.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0220   -2.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0220   -2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -0.8616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.1654   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6503   -1.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0220   -0.4491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.7365    0.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5504   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8799    2.0259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1654    1.6134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4509    2.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    2.8509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7365    3.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365    4.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    2.8509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1654    4.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.8616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -3.3366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943    3.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943    1.6134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 38  1  0  0  0  0
  3  4  1  0  0  0  0
  4 36  2  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6 23  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 24  2  0  0  0  0
 20 21  1  0  0  0  0
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 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 29  1  0  0  0  0
 26 27  2  0  0  0  0
 26 32  1  0  0  0  0
 27 28  1  0  0  0  0
 27 35  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 41 42  1  0  0  0  0
 41 47  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 48  1  0  0  0  0
 45 46  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  6  0  0  0
 29 50  1  6  0  0  0
 20 51  1  6  0  0  0
 30 10  1  6  0  0  0
  5  4  1  6  0  0  0
 25 24  1  1  0  0  0
 47 52  1  1  0  0  0
 41 53  1  6  0  0  0
 42 33  1  1  0  0  0
M  END

HMDB0037405
     RDKit          3D
8-Glucopyranosylprocyanidin B2
 89 95  0  0  0  0  0  0  0  0999 V2000
   -6.4822    0.5712    3.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0461    1.1078    2.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7751    0.1366    1.2414 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7987   -0.8497    1.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493   -1.1206    0.4121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8273   -1.7061    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -2.9631    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -3.6817    1.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2235   -3.4222    0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1772   -2.6741    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177   -3.1356    0.3051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -1.4533   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796   -0.9647   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    0.3306   -0.6914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    1.2963   -0.0780 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1088    2.6530   -0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350    2.9947   -1.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    4.3144   -2.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366    5.3597   -1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6007    6.6467   -1.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115    5.0508   -0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    6.0386    0.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    3.7516    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4831    0.7792   -0.0618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2799    1.7651   -0.6497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131   -0.5107   -0.8070 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7486   -1.1267   -1.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6637   -1.7422   -3.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747   -2.4304   -2.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9942   -2.4981   -2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4832   -0.0341    1.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6095    0.7067    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0884   -1.5486   -0.7174 C   0  0  2  0  0  0  0  0  0  0  0  0
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 51 87  1  0
 52 88  1  1
 53 89  1  0
M  END

  Mrv0541 02241208272D          

 53 59  0  0  0  0            999 V2000
    2.8359    0.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -0.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069   -2.0991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6925   -1.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    2.8509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    2.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925    1.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4069    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    1.6134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359    2.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -4.1616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -3.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4509   -2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6925   -3.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7365   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7365   -0.8616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4509   -0.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6503   -1.5290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0220   -0.4491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0220    0.3759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7365    0.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1654    0.7884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799   -0.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8359   -2.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504   -1.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5504   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2648   -0.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943    0.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8799    2.0259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1654    1.6134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4509    2.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    2.8509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7365    3.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8799    2.8509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1654    3.2634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1654    4.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -0.8616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214   -3.3366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943    3.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943    1.6134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 38  1  0  0  0  0
  3  4  1  0  0  0  0
  4 36  2  0  0  0  0
  5  6  1  0  0  0  0
  5 20  1  0  0  0  0
  6 23  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 22  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 24  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 26  1  0  0  0  0
 25 29  1  0  0  0  0
 26 27  2  0  0  0  0
 26 32  1  0  0  0  0
 27 28  1  0  0  0  0
 27 35  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 41 42  1  0  0  0  0
 41 47  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 48  1  0  0  0  0
 45 46  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  6  0  0  0
 29 50  1  6  0  0  0
 20 51  1  6  0  0  0
 30 10  1  6  0  0  0
  5  4  1  6  0  0  0
 25 24  1  1  0  0  0
 47 52  1  1  0  0  0
 41 53  1  6  0  0  0
 42 33  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0037405

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2O[C@@H]([C@H](O)[C@@H](C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC=C(O)C(O)=C3)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C36H36O17/c37-10-23-28(47)30(49)31(50)36(51-23)26-21(45)9-20(44)25-27(29(48)33(53-35(25)26)12-2-4-15(39)18(42)6-12)24-19(43)8-16(40)13-7-22(46)32(52-34(13)24)11-1-3-14(38)17(41)5-11/h1-6,8-9,22-23,27-33,36-50H,7,10H2/t22-,23-,27+,28-,29-,30+,31-,32-,33-,36+/m1/s1

> <INCHI_KEY>
JBDZOCOBUGXPJW-LYGYLKCLSA-N

> <FORMULA>
C36H36O17

> <MOLECULAR_WEIGHT>
740.6608

> <EXACT_MASS>
740.195249726

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
71.80293604908366

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.3584241086666672

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.041413900182787

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.597723228319344

> <JCHEM_PKA_STRONGEST_BASIC>
-5.176584915395201

> <JCHEM_POLAR_SURFACE_AREA>
310.90999999999997

> <JCHEM_REFRACTIVITY>
179.62630000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037405
     RDKit          3D
8-Glucopyranosylprocyanidin B2
 89 95  0  0  0  0  0  0  0  0999 V2000
   -6.4822    0.5712    3.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0461    1.1078    2.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7751    0.1366    1.2414 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7987   -0.8497    1.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1493   -1.1206    0.4121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8273   -1.7061    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -2.9631    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -3.6817    1.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2235   -3.4222    0.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1772   -2.6741    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177   -3.1356    0.3051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -1.4533   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7796   -0.9647   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    0.3306   -0.6914 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9411    1.2963   -0.0780 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1088    2.6530   -0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2350    2.9947   -1.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959    4.3144   -2.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366    5.3597   -1.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6007    6.6467   -1.8456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115    5.0508   -0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3455    6.0386    0.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    3.7516    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4831    0.7792   -0.0618 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2799    1.7651   -0.6497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5131   -0.5107   -0.8070 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7486   -1.1267   -1.2016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7568   -1.7551   -2.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6637   -1.7422   -3.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747   -2.4304   -2.9397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9942   -2.4981   -2.1900 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1490   -3.1705   -2.6388 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0101   -1.8958   -0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9233   -1.2228   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9916   -0.6141    0.7471 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1416   -0.7423    1.5825 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2445    0.1560    1.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4832   -0.0341    1.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6095    0.7067    1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4618    1.6823    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5733    2.4038   -0.0039 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000    1.8943   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0968    2.8749   -1.1691 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1058    1.1247    0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6406   -2.1703    1.3069 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4994   -2.6608    2.2342 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.0755   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0884   -1.5486   -0.7174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2388   -0.6609   -1.7428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4768   -1.7994   -0.0804 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4172   -2.7138    0.9547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9527   -0.4953    0.5692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4549    0.2699   -0.4965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4585    0.8022    3.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1419    1.7649    2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8694    1.7905    1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2750    0.7494    0.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531    0.0190    0.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4293   -4.5874    1.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683   -4.4115    1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506   -4.0405    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133    1.3721    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092    2.2331   -2.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4942    4.5887   -3.3692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6310    7.4181   -1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4499    7.0110    0.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    3.5053    1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    0.5519    0.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054    2.4020    0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.2389   -1.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284   -1.4131   -3.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8587   -2.8990   -3.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1241   -3.6123   -3.5638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8867   -0.6065    2.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6640   -0.7634    2.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5753    0.5437    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5833    3.1318   -0.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1744    3.0490   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1517    1.3092   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7346   -2.8261    1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1062   -3.3808    1.8831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7077   -3.0628   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9041   -1.2553   -0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7706   -2.5397   -1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3256   -1.1373   -2.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1471   -2.1523   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6523   -2.3215    1.8574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7642   -0.7196    1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8514   -0.3444   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 15 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 40 42  1  0
 42 43  1  0
 42 44  2  0
 36 45  1  0
 45 46  1  0
 45 47  1  0
  5 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 50 52  1  0
 52 53  1  0
 52  3  1  0
 13  6  1  0
 23 16  1  0
 34 27  1  0
 44 37  1  0
 26 12  1  0
 47 33  1  0
  1 54  1  0
  2 55  1  0
  2 56  1  0
  3 57  1  6
  5 58  1  6
  8 59  1  0
  9 60  1  0
 11 61  1  0
 15 62  1  1
 17 63  1  0
 18 64  1  0
 20 65  1  0
 22 66  1  0
 23 67  1  0
 24 68  1  1
 25 69  1  0
 26 70  1  6
 29 71  1  0
 30 72  1  0
 32 73  1  0
 36 74  1  1
 38 75  1  0
 39 76  1  0
 41 77  1  0
 43 78  1  0
 44 79  1  0
 45 80  1  6
 46 81  1  0
 47 82  1  0
 47 83  1  0
 48 84  1  6
 49 85  1  0
 50 86  1  6
 51 87  1  0
 52 88  1  1
 53 89  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       5.294   0.702   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.294  -0.838   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.960  -1.608   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.960  -3.148   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.626  -3.918   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.293  -3.148   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.626   5.322   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.626   3.782   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.293   3.012   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.293   1.472   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.626   0.702   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.960   1.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.960   3.012   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.294   3.782   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.375  -7.768   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.375  -6.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.708  -5.458   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.708  -3.918   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.042  -3.148   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.626  -5.458   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.293  -6.228   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.041  -5.458   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.041  -3.918   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.375  -3.148   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.375  -1.608   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.708  -0.838   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.042  -1.608   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.947  -2.854   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.041  -0.838   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.041   0.702   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.375   1.472   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.708   0.702   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.042   1.472   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.376   0.702   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.376  -0.838   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.294  -3.918   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.627  -3.148   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.627  -1.608   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       7.961  -0.838   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -6.709   1.472   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.376   3.782   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -4.042   3.012   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.708   3.782   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -2.708   5.322   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -1.375   6.092   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -1.375   7.632   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -5.376   5.322   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -4.042   6.092   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -4.042   7.632   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       1.293  -1.608   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       3.960  -6.228   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -6.709   6.092   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -6.709   3.012   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3   36    5                                                  
CONECT    5    6   20    4                                                  
CONECT    6    5   23                                                       
CONECT    7    8                                                            
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    8   12   14                                                  
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18                                                            
CONECT   20    5   21   51                                                  
CONECT   21   20   22                                                       
CONECT   22   16   21   23                                                  
CONECT   23    6   22   24                                                  
CONECT   24   18   23   25                                                  
CONECT   25   26   29   24                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28   35                                                  
CONECT   28   27                                                            
CONECT   29   25   30   50                                                  
CONECT   30   29   31   10                                                  
CONECT   31   30   32                                                       
CONECT   32   26   31   33                                                  
CONECT   33   32   34   42                                                  
CONECT   34   33   35   40                                                  
CONECT   35   27   34                                                       
CONECT   36    4   37                                                       
CONECT   37   36   38                                                       
CONECT   38    2   37   39                                                  
CONECT   39   38                                                            
CONECT   40   34                                                            
CONECT   41   42   47   53                                                  
CONECT   42   41   43   33                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   48                                                  
CONECT   45   44   46                                                       
CONECT   46   45                                                            
CONECT   47   41   48   52                                                  
CONECT   48   44   47   49                                                  
CONECT   49   48                                                            
CONECT   50   29                                                            
CONECT   51   20                                                            
CONECT   52   47                                                            
CONECT   53   41                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

COMPND    HMDB0037405
HETATM    1  O1  UNL     1      -6.482   0.571   3.507  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.046   1.108   2.324  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.775   0.137   1.241  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.799  -0.850   1.581  1.00  0.00           O  
HETATM    5  C3  UNL     1      -4.149  -1.121   0.412  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.827  -1.706   0.369  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.520  -2.963   0.886  1.00  0.00           C  
HETATM    8  O3  UNL     1      -3.566  -3.682   1.405  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.224  -3.422   0.860  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.177  -2.674   0.332  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.118  -3.136   0.305  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.473  -1.453  -0.168  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.780  -0.965  -0.150  1.00  0.00           C  
HETATM   14  O5  UNL     1      -1.864   0.331  -0.691  1.00  0.00           O  
HETATM   15  C10 UNL     1      -0.941   1.296  -0.078  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.109   2.653  -0.599  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.235   2.995  -1.922  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.396   4.314  -2.334  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.437   5.360  -1.426  1.00  0.00           C  
HETATM   20  O6  UNL     1      -1.601   6.647  -1.846  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.312   5.051  -0.114  1.00  0.00           C  
HETATM   22  O7  UNL     1      -1.346   6.039   0.854  1.00  0.00           O  
HETATM   23  C16 UNL     1      -1.154   3.752   0.289  1.00  0.00           C  
HETATM   24  C17 UNL     1       0.483   0.779  -0.062  1.00  0.00           C  
HETATM   25  O8  UNL     1       1.280   1.765  -0.650  1.00  0.00           O  
HETATM   26  C18 UNL     1       0.513  -0.511  -0.807  1.00  0.00           C  
HETATM   27  C19 UNL     1       1.749  -1.127  -1.202  1.00  0.00           C  
HETATM   28  C20 UNL     1       1.757  -1.755  -2.458  1.00  0.00           C  
HETATM   29  O9  UNL     1       0.664  -1.742  -3.277  1.00  0.00           O  
HETATM   30  C21 UNL     1       2.875  -2.430  -2.940  1.00  0.00           C  
HETATM   31  C22 UNL     1       3.994  -2.498  -2.190  1.00  0.00           C  
HETATM   32  O10 UNL     1       5.149  -3.170  -2.639  1.00  0.00           O  
HETATM   33  C23 UNL     1       4.010  -1.896  -0.968  1.00  0.00           C  
HETATM   34  C24 UNL     1       2.923  -1.223  -0.483  1.00  0.00           C  
HETATM   35  O11 UNL     1       2.992  -0.614   0.747  1.00  0.00           O  
HETATM   36  C25 UNL     1       4.142  -0.742   1.582  1.00  0.00           C  
HETATM   37  C26 UNL     1       5.244   0.156   1.144  1.00  0.00           C  
HETATM   38  C27 UNL     1       6.483  -0.034   1.691  1.00  0.00           C  
HETATM   39  C28 UNL     1       7.610   0.707   1.321  1.00  0.00           C  
HETATM   40  C29 UNL     1       7.462   1.682   0.356  1.00  0.00           C  
HETATM   41  O12 UNL     1       8.573   2.404  -0.004  1.00  0.00           O  
HETATM   42  C30 UNL     1       6.200   1.894  -0.216  1.00  0.00           C  
HETATM   43  O13 UNL     1       6.097   2.875  -1.169  1.00  0.00           O  
HETATM   44  C31 UNL     1       5.106   1.125   0.189  1.00  0.00           C  
HETATM   45  C32 UNL     1       4.641  -2.170   1.307  1.00  0.00           C  
HETATM   46  O14 UNL     1       5.499  -2.661   2.234  1.00  0.00           O  
HETATM   47  C33 UNL     1       5.229  -2.075  -0.113  1.00  0.00           C  
HETATM   48  C34 UNL     1      -5.088  -1.549  -0.717  1.00  0.00           C  
HETATM   49  O15 UNL     1      -5.239  -0.661  -1.743  1.00  0.00           O  
HETATM   50  C35 UNL     1      -6.477  -1.799  -0.080  1.00  0.00           C  
HETATM   51  O16 UNL     1      -6.417  -2.714   0.955  1.00  0.00           O  
HETATM   52  C36 UNL     1      -6.953  -0.495   0.569  1.00  0.00           C  
HETATM   53  O17 UNL     1      -7.455   0.270  -0.496  1.00  0.00           O  
HETATM   54  H1  UNL     1      -7.458   0.802   3.672  1.00  0.00           H  
HETATM   55  H2  UNL     1      -5.142   1.765   2.407  1.00  0.00           H  
HETATM   56  H3  UNL     1      -6.869   1.790   1.924  1.00  0.00           H  
HETATM   57  H4  UNL     1      -5.275   0.749   0.411  1.00  0.00           H  
HETATM   58  H5  UNL     1      -3.953   0.019   0.033  1.00  0.00           H  
HETATM   59  H6  UNL     1      -3.429  -4.587   1.803  1.00  0.00           H  
HETATM   60  H7  UNL     1      -0.968  -4.411   1.257  1.00  0.00           H  
HETATM   61  H8  UNL     1       1.351  -4.040   0.662  1.00  0.00           H  
HETATM   62  H9  UNL     1      -1.313   1.372   0.998  1.00  0.00           H  
HETATM   63  H10 UNL     1      -1.209   2.233  -2.681  1.00  0.00           H  
HETATM   64  H11 UNL     1      -1.494   4.589  -3.369  1.00  0.00           H  
HETATM   65  H12 UNL     1      -1.631   7.418  -1.211  1.00  0.00           H  
HETATM   66  H13 UNL     1      -1.450   7.011   0.728  1.00  0.00           H  
HETATM   67  H14 UNL     1      -1.060   3.505   1.333  1.00  0.00           H  
HETATM   68  H15 UNL     1       0.742   0.552   0.990  1.00  0.00           H  
HETATM   69  H16 UNL     1       1.505   2.402   0.036  1.00  0.00           H  
HETATM   70  H17 UNL     1      -0.028  -0.239  -1.789  1.00  0.00           H  
HETATM   71  H18 UNL     1      -0.228  -1.413  -3.208  1.00  0.00           H  
HETATM   72  H19 UNL     1       2.859  -2.899  -3.904  1.00  0.00           H  
HETATM   73  H20 UNL     1       5.124  -3.612  -3.564  1.00  0.00           H  
HETATM   74  H21 UNL     1       3.887  -0.606   2.622  1.00  0.00           H  
HETATM   75  H22 UNL     1       6.664  -0.763   2.449  1.00  0.00           H  
HETATM   76  H23 UNL     1       8.575   0.544   1.760  1.00  0.00           H  
HETATM   77  H24 UNL     1       8.583   3.132  -0.692  1.00  0.00           H  
HETATM   78  H25 UNL     1       5.174   3.049  -1.595  1.00  0.00           H  
HETATM   79  H26 UNL     1       4.152   1.309  -0.271  1.00  0.00           H  
HETATM   80  H27 UNL     1       3.735  -2.826   1.210  1.00  0.00           H  
HETATM   81  H28 UNL     1       6.106  -3.381   1.883  1.00  0.00           H  
HETATM   82  H29 UNL     1       5.708  -3.063  -0.287  1.00  0.00           H  
HETATM   83  H30 UNL     1       5.904  -1.255  -0.272  1.00  0.00           H  
HETATM   84  H31 UNL     1      -4.771  -2.540  -1.131  1.00  0.00           H  
HETATM   85  H32 UNL     1      -5.326  -1.137  -2.610  1.00  0.00           H  
HETATM   86  H33 UNL     1      -7.147  -2.152  -0.864  1.00  0.00           H  
HETATM   87  H34 UNL     1      -6.652  -2.321   1.857  1.00  0.00           H  
HETATM   88  H35 UNL     1      -7.764  -0.720   1.253  1.00  0.00           H  
HETATM   89  H36 UNL     1      -7.851  -0.344  -1.158  1.00  0.00           H  
CONECT    1    2   54
CONECT    2    3   55   56
CONECT    3    4   52   57
CONECT    4    5
CONECT    5    6   48   58
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    8   59
CONECT    9   10   10   60
CONECT   10   11   12
CONECT   11   61
CONECT   12   13   13   26
CONECT   13   14
CONECT   14   15
CONECT   15   16   24   62
CONECT   16   17   17   23
CONECT   17   18   63
CONECT   18   19   19   64
CONECT   19   20   21
CONECT   20   65
CONECT   21   22   23   23
CONECT   22   66
CONECT   23   67
CONECT   24   25   26   68
CONECT   25   69
CONECT   26   27   70
CONECT   27   28   28   34
CONECT   28   29   30
CONECT   29   71
CONECT   30   31   31   72
CONECT   31   32   33
CONECT   32   73
CONECT   33   34   34   47
CONECT   34   35
CONECT   35   36
CONECT   36   37   45   74
CONECT   37   38   38   44
CONECT   38   39   75
CONECT   39   40   40   76
CONECT   40   41   42
CONECT   41   77
CONECT   42   43   44   44
CONECT   43   78
CONECT   44   79
CONECT   45   46   47   80
CONECT   46   81
CONECT   47   82   83
CONECT   48   49   50   84
CONECT   49   85
CONECT   50   51   52   86
CONECT   51   87
CONECT   52   53   88
CONECT   53   89
END

HMDB0037405
     RDKit          3D
8-Glucopyranosylprocyanidin B2
 89 95  0  0  0  0  0  0  0  0999 V2000
   -6.4822    0.5712    3.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-C-Glucopyranosylprocyanidin b2	HMDB

Chemical Formula

C₃₆H₃₆O₁₇

Average Molecular Weight

740.6608

Monoisotopic Molecular Weight

740.195249726

IUPAC Name

(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

CAS Registry Number

103215-58-3

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2O[C@@H]([C@H](O)[C@@H](C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC=C(O)C(O)=C3)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C36H36O17/c37-10-23-28(47)30(49)31(50)36(51-23)26-21(45)9-20(44)25-27(29(48)33(53-35(25)26)12-2-4-15(39)18(42)6-12)24-19(43)8-16(40)13-7-22(46)32(52-34(13)24)11-1-3-14(38)17(41)5-11/h1-6,8-9,22-23,27-33,36-50H,7,10H2/t22-,23-,27+,28-,29-,30+,31-,32-,33-,36+/m1/s1

InChI Key

JBDZOCOBUGXPJW-LYGYLKCLSA-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

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Flavonoid c-glycoside
Flavonoid-8-c-glycoside
Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Flavan
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Oxane
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Polyol
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037405)
Cytoplasm (HMDB: HMDB0037405)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037405)

Source

Exogenous

Exogenous (HMDB: HMDB0037405)

Food

Food (HMDB: HMDB0037405)

Herb and spice

Spice

Chinese cinnamon (FooDB: FOOD00050)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0037405)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037405)

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
Water Solubility	1.17 g/L	ALOGPS
logP	1.21	ALOGPS
logP	0.36	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	310.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	179.63 m³·mol⁻¹	ChemAxon
Polarizability	71.8 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	260.143	30932474
DeepCCS	[M-H]-	258.42	30932474
DeepCCS	[M-2H]-	292.829	30932474
DeepCCS	[M+Na]+	266.472	30932474
AllCCS	[M+H]+	261.4	32859911
AllCCS	[M+H-H2O]+	260.8	32859911
AllCCS	[M+NH4]+	262.0	32859911
AllCCS	[M+Na]+	262.2	32859911
AllCCS	[M-H]-	265.1	32859911
AllCCS	[M+Na-2H]-	269.2	32859911
AllCCS	[M+HCOO]-	273.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Glucopyranosylprocyanidin B2	OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2O[C@@H]([C@H](O)[C@@H](C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC=C(O)C(O)=C3)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1	7358.1	Standard polar	33892256
8-Glucopyranosylprocyanidin B2	OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2O[C@@H]([C@H](O)[C@@H](C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC=C(O)C(O)=C3)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1	6188.0	Standard non polar	33892256
8-Glucopyranosylprocyanidin B2	OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2O[C@@H]([C@H](O)[C@@H](C3=C(O)C=C(O)C4=C3O[C@@H]([C@H](O)C4)C3=CC=C(O)C(O)=C3)C2=C(O)C=C1O)C1=CC=C(O)C(O)=C1	7026.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_1_14) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Glucopyranosylprocyanidin B2 GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Positive-QTOF	splash10-00du-0100080900-22a7764e6930dfcc054b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Positive-QTOF	splash10-02mr-0300593400-0c5be904e4f2160fe01e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Positive-QTOF	splash10-0kg9-0100932100-0ba9d47992cf3eb85404	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Negative-QTOF	splash10-000i-0000022900-05df8dfcbeebd0bcb5fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Negative-QTOF	splash10-0079-3950213400-0738f65d549be4cd0cfd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Negative-QTOF	splash10-00kr-5595013100-0a4c6723ab0efc06de04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Positive-QTOF	splash10-006x-0000000900-41ae947ab44323ae78f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Positive-QTOF	splash10-00dl-0430066900-4235ed27d433e7ac5f7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Positive-QTOF	splash10-05fr-2400039100-80502cb0789c115101bc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 10V, Negative-QTOF	splash10-000i-0000002900-e978dd7b87634cf91d08	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 20V, Negative-QTOF	splash10-0abi-1000039600-0ab288f5818ec21ab301	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Glucopyranosylprocyanidin B2 40V, Negative-QTOF	splash10-000l-3970168700-43cef26667cb764b2a47	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016449

KNApSAcK ID

C00006327

Chemspider ID

10272882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21637579

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 8-Glucopyranosylprocyanidin B2 (HMDB0037405)

MOL for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

3D MOL for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

3D SDF for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

3D-SDF for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

PDB for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

3D PDB for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

SMILES for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

INCHI for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

Structure for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

3D Structure for HMDB0037405 (8-Glucopyranosylprocyanidin B2)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra