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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:37:45 UTC

Update Date

2022-03-07 02:55:18 UTC

HMDB ID

HMDB0037384

Secondary Accession Numbers

HMDB37384

Metabolite Identification

Common Name

Granatin B

Description

Granatin B belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Granatin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, granatin b has been detected, but not quantified in, fruits and pomegranates. This could make granatin b a potential biomarker for the consumption of these foods. Granatin B is an ellagitannin found in the fruit of Punica granatum (pomegranate). It is a molecule having an enantiomeric dehydrohexahydroxydiphenoyl group. It is a highly active carbonic anhydrase inhibitor.

Structure

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


  Mrv0541 02241211062D          

 68 76  0  0  0  0            999 V2000
    3.6502    0.1264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2693   -0.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -0.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363   -0.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2534   -1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1423   -1.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4124   -1.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0311   -3.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060   -3.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519   -2.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900   -2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900   -1.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8886   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155    2.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614    2.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598    3.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6668   -6.3485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7301   -5.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954   -5.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6029   -5.5236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900   -5.9676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -5.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3805   -4.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9519   -3.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6502   -4.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7141   -5.0788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0788   -5.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2060   -6.2852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284   -6.1580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284   -5.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550   -4.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9205   -4.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859   -4.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4124   -5.4597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853   -3.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763   -3.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3646   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -0.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7301    1.0791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1587    1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7934    1.2693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -2.0315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2380   -0.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2853   -0.7620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6035   -0.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -1.4603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1423   -2.7300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998    3.8087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013    3.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9838    2.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950    2.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763    3.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376    3.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1900    3.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343    4.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172    4.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7614    5.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3013    5.6502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917    4.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9205    4.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1583    6.3485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    4.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9205    5.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5396    3.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2226    4.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0321    3.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 45  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 49  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 25  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 48  1  0  0  0  0
 14 15  1  0  0  0  0
 14 39  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 56  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 31  1  0  0  0  0
 20 21  1  0  0  0  0
 20 34  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 24 32  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 35  1  0  0  0  0
 28 29  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 37  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 47  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 53  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 51 64  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 67  1  0  0  0  0
 55 56  1  0  0  0  0
 55 62  2  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 61  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 64 67  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
M  END

HMDB0037384
     RDKit          3D
Granatin B
 96104  0  0  0  0  0  0  0  0999 V2000
   -1.1008    0.2510   -3.6459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4943    0.2490   -2.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    1.2779   -1.7250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3096    1.1825   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2909    2.3599    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6580    3.3880    0.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936    4.6689   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    4.9075   -0.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    5.7482    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    5.5779    0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5081    6.6381    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960    6.4483    1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2091    7.8928    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400    8.8981    0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0321    8.0731   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360    9.3182   -0.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909    7.0054   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767    2.0677    1.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    0.8892    1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4978    0.3950    2.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -0.0689    1.6380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694    0.3163    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321    1.5689    0.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7809   -0.4930   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469    0.1646   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586   -0.4180   -2.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1936    0.3513   -3.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1598   -1.7626   -2.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8371   -2.4584   -3.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182   -2.4870   -1.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2169   -3.8229   -2.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -1.8431   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -2.8291   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804   -2.9335   -0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236   -4.0395    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699   -4.9525    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8382   -6.0269    1.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266   -4.8227    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5730   -5.7695    1.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4304   -3.7832    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8332   -3.7655    0.6095 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3310   -2.2002   -1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596   -3.0199   -1.8413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592   -0.9526   -1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096    0.1217   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752   -0.1356    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -1.3989    1.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8292   -1.8948    1.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6821   -2.9378    2.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905   -1.4236    1.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -1.0614    2.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253   -0.6465    2.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -0.2989    4.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8335   -0.5814    1.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1770   -0.1420    1.8452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799   -0.9167    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9275   -1.3446    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5494   -1.6937   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4456   -0.7824   -1.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -0.8979   -2.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7209   -1.4393   -2.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6447   -1.4155   -3.5819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9522   -2.0811   -1.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0202   -2.8765   -1.3393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186   -0.8635   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6374   -2.8039   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2163   -3.3568   -2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6410   -3.6587   -0.1343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267    0.9754    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1646    2.7201   -0.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8504    4.5979    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    7.2250    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9475    9.8262    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770    9.4912   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    7.1572   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2121    1.2891    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004   -0.5871    2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488    0.9486    3.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953    1.2557   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7299    0.0275   -4.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4484   -1.9150   -4.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6657   -4.3487   -2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526   -4.2318    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -6.1331    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0787   -6.5118    2.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3517   -3.0431    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
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 11 12  1  0
 11 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
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 66 58  1  0
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 46 19  1  0
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 32 24  1  0
 40 33  1  0
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 10 71  1  0
 12 72  1  0
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 60 93  1  0
 64 94  1  0
 67 95  1  0
 68 96  1  0
M  END


  Mrv0541 02241211062D          

 68 76  0  0  0  0            999 V2000
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 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037384

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC3C2OC(=O)C2=CC(O)=C(O)C4=C2C2C(=CC(=O)C(O)(O4)C2(O)O)C(=O)OC13

> <INCHI_IDENTIFIER>
InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-37(57)11-5-17(46)27(51)31-22(11)23-12(38(58)66-33)6-19(47)41(61,68-31)40(23,59)60)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2

> <INCHI_KEY>
OYPBFXPEIVEPRY-UHFFFAOYSA-N

> <FORMULA>
C41H28O27

> <MOLECULAR_WEIGHT>
952.6448

> <EXACT_MASS>
952.08179569

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
84.33211420977902

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,16,17,18,21,22,23,34,35,39,39-undecahydroxy-2,5,13,26,31-pentaoxo-6,9,12,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁸.0¹⁰,²⁹.0¹⁴,¹⁹.0²⁰,²⁵.0³²,³⁷]tetraconta-3,14,16,18,20,22,24,32,34,36-decaen-8-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.2012349269999993

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.455675185115912

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.651842780861121

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5547113132851935

> <JCHEM_POLAR_SURFACE_AREA>
450.2500000000001

> <JCHEM_REFRACTIVITY>
210.55630000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,16,17,18,21,22,23,34,35,39,39-undecahydroxy-2,5,13,26,31-pentaoxo-6,9,12,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁸.0¹⁰,²⁹.0¹⁴,¹⁹.0²⁰,²⁵.0³²,³⁷]tetraconta-3,14,16,18,20,22,24,32,34,36-decaen-8-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037384
     RDKit          3D
Granatin B
 96104  0  0  0  0  0  0  0  0999 V2000
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    0.2909    2.3599    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6580    3.3880    0.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6390    5.5779    0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5081    6.6381    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8321    1.5689    0.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6030   -1.8431   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -2.8291   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3951   -0.8979   -2.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7209   -1.4393   -2.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6410   -3.6587   -0.1343 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7299    0.0275   -4.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6526   -4.2318    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0787   -6.5118    2.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3517   -3.0431    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837    0.6964   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2878   -1.1391    3.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6685   -2.3808   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -0.5986   -4.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8862   -3.8338   -1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246   -3.7059   -2.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -4.5131   -0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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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       6.814   0.236   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.103  -0.830   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.444  -0.238   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.614  -1.778   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.206  -2.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.866  -3.319   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.814  -2.370   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.236  -2.726   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -7.525  -5.925   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -5.985  -5.925   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.510  -4.503   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.088  -4.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.088  -2.607   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.392  -1.422   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.629   3.792   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.155   5.213   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.458   5.925   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.245 -11.851   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.363 -10.429   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.178  -9.718   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.125 -10.311   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.088 -11.140   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.444  -9.600   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.444  -8.177   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.510  -7.348   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.814  -8.059   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.933  -9.480   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.747 -10.311   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.985 -11.732   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.666 -11.495   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.666  -9.718   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.903  -8.177   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.718  -7.584   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.534  -8.414   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.236 -10.191   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.533  -6.518   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.889  -6.400   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.547  -4.978   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.088  -0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.836  -0.119   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.363   2.014   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.296   2.962   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.481   2.369   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       2.429  -3.792   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       2.311  -1.303   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       0.533  -1.422   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -1.127  -1.303   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.192  -2.726   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       5.866  -5.096   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       3.733   7.110   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       2.429   6.636   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       1.836   5.213   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       0.177   4.621   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.889   5.806   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -2.310   6.636   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -4.088   6.280   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -4.917   7.584   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -4.325   8.888   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -5.155   9.954   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      -2.429  10.547   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -2.785   9.124   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -1.718   8.058   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       0.295  11.851   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       1.007   7.939   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0       1.718   9.362   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0       1.007   6.754   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0      -0.416   7.702   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      -0.060   6.043   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   45                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   49                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   48                                                  
CONECT   14   13   15   39                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   56                                                  
CONECT   17   16                                                            
CONECT   18   19                                                            
CONECT   19   18   20   31                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   22   24   28                                                  
CONECT   24   23   25   32                                                  
CONECT   25   10   24   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   23   27   29                                                  
CONECT   29   28                                                            
CONECT   30   31                                                            
CONECT   31   19   30   32                                                  
CONECT   32   24   31   33                                                  
CONECT   33   32   34   37                                                  
CONECT   34   20   33                                                       
CONECT   35   27                                                            
CONECT   36   37                                                            
CONECT   37   33   36   38                                                  
CONECT   38   37   39                                                       
CONECT   39   14   38   40                                                  
CONECT   40   39   41   47                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   53                                                  
CONECT   43   42                                                            
CONECT   44   45                                                            
CONECT   45    4   44   46                                                  
CONECT   46   45   47                                                       
CONECT   47   40   46   48                                                  
CONECT   48   13   47                                                       
CONECT   49    6                                                            
CONECT   50   51                                                            
CONECT   51   50   52   64                                                  
CONECT   52   51   53                                                       
CONECT   53   42   52   54                                                  
CONECT   54   53   55   67                                                  
CONECT   55   54   56   62                                                  
CONECT   56   16   55   57                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   61                                                  
CONECT   59   58                                                            
CONECT   60   61                                                            
CONECT   61   58   60   62                                                  
CONECT   62   55   61   63                                                  
CONECT   63   62   64                                                       
CONECT   64   51   63   65   67                                             
CONECT   65   64                                                            
CONECT   66   67                                                            
CONECT   67   54   64   66   68                                             
CONECT   68   67                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  152    0
END

COMPND    HMDB0037384
HETATM    1  O1  UNL     1      -1.101   0.251  -3.646  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.494   0.249  -2.368  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.864   1.278  -1.725  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.310   1.182  -0.531  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.291   2.360   0.196  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.658   3.388   0.389  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.494   4.669  -0.093  1.00  0.00           C  
HETATM    8  O4  UNL     1       0.561   4.907  -0.731  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.447   5.748   0.087  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.639   5.578   0.774  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.508   6.638   0.914  1.00  0.00           C  
HETATM   12  O5  UNL     1      -4.696   6.448   1.605  1.00  0.00           O  
HETATM   13  C8  UNL     1      -3.209   7.893   0.372  1.00  0.00           C  
HETATM   14  O6  UNL     1      -4.140   8.898   0.562  1.00  0.00           O  
HETATM   15  C9  UNL     1      -2.032   8.073  -0.310  1.00  0.00           C  
HETATM   16  O7  UNL     1      -1.736   9.318  -0.847  1.00  0.00           O  
HETATM   17  C10 UNL     1      -1.191   7.005  -0.433  1.00  0.00           C  
HETATM   18  O8  UNL     1       0.777   2.068   1.511  1.00  0.00           O  
HETATM   19  C11 UNL     1       1.516   0.889   1.478  1.00  0.00           C  
HETATM   20  C12 UNL     1       2.498   0.395   2.365  1.00  0.00           C  
HETATM   21  O9  UNL     1       3.619  -0.069   1.638  1.00  0.00           O  
HETATM   22  C13 UNL     1       4.369   0.316   0.586  1.00  0.00           C  
HETATM   23  O10 UNL     1       4.832   1.569   0.570  1.00  0.00           O  
HETATM   24  C14 UNL     1       4.781  -0.493  -0.602  1.00  0.00           C  
HETATM   25  C15 UNL     1       5.647   0.165  -1.454  1.00  0.00           C  
HETATM   26  C16 UNL     1       6.359  -0.418  -2.506  1.00  0.00           C  
HETATM   27  O11 UNL     1       7.194   0.351  -3.288  1.00  0.00           O  
HETATM   28  C17 UNL     1       6.160  -1.763  -2.682  1.00  0.00           C  
HETATM   29  O12 UNL     1       6.837  -2.458  -3.719  1.00  0.00           O  
HETATM   30  C18 UNL     1       5.318  -2.487  -1.887  1.00  0.00           C  
HETATM   31  O13 UNL     1       5.217  -3.823  -2.157  1.00  0.00           O  
HETATM   32  C19 UNL     1       4.603  -1.843  -0.824  1.00  0.00           C  
HETATM   33  C20 UNL     1       3.690  -2.829  -0.187  1.00  0.00           C  
HETATM   34  C21 UNL     1       2.280  -2.934  -0.235  1.00  0.00           C  
HETATM   35  C22 UNL     1       1.724  -4.040   0.475  1.00  0.00           C  
HETATM   36  C23 UNL     1       2.470  -4.952   1.159  1.00  0.00           C  
HETATM   37  O14 UNL     1       1.838  -6.027   1.843  1.00  0.00           O  
HETATM   38  C24 UNL     1       3.827  -4.823   1.179  1.00  0.00           C  
HETATM   39  O15 UNL     1       4.573  -5.770   1.883  1.00  0.00           O  
HETATM   40  C25 UNL     1       4.430  -3.783   0.519  1.00  0.00           C  
HETATM   41  O16 UNL     1       5.833  -3.765   0.610  1.00  0.00           O  
HETATM   42  C26 UNL     1       1.331  -2.200  -1.015  1.00  0.00           C  
HETATM   43  O17 UNL     1       0.660  -3.020  -1.841  1.00  0.00           O  
HETATM   44  O18 UNL     1       0.859  -0.953  -1.224  1.00  0.00           O  
HETATM   45  C27 UNL     1       0.710   0.122  -0.479  1.00  0.00           C  
HETATM   46  C28 UNL     1       0.575  -0.136   1.031  1.00  0.00           C  
HETATM   47  O19 UNL     1       0.385  -1.399   1.384  1.00  0.00           O  
HETATM   48  C29 UNL     1      -0.829  -1.895   1.879  1.00  0.00           C  
HETATM   49  O20 UNL     1      -0.682  -2.938   2.634  1.00  0.00           O  
HETATM   50  C30 UNL     1      -2.190  -1.424   1.679  1.00  0.00           C  
HETATM   51  C31 UNL     1      -2.833  -1.061   2.903  1.00  0.00           C  
HETATM   52  C32 UNL     1      -4.125  -0.647   2.946  1.00  0.00           C  
HETATM   53  O21 UNL     1      -4.713  -0.299   4.159  1.00  0.00           O  
HETATM   54  C33 UNL     1      -4.833  -0.581   1.753  1.00  0.00           C  
HETATM   55  O22 UNL     1      -6.177  -0.142   1.845  1.00  0.00           O  
HETATM   56  C34 UNL     1      -4.280  -0.917   0.556  1.00  0.00           C  
HETATM   57  C35 UNL     1      -2.927  -1.345   0.507  1.00  0.00           C  
HETATM   58  C36 UNL     1      -2.549  -1.694  -0.863  1.00  0.00           C  
HETATM   59  C37 UNL     1      -2.446  -0.782  -1.987  1.00  0.00           C  
HETATM   60  C38 UNL     1      -3.395  -0.898  -2.990  1.00  0.00           C  
HETATM   61  C39 UNL     1      -4.721  -1.439  -2.775  1.00  0.00           C  
HETATM   62  O23 UNL     1      -5.645  -1.416  -3.582  1.00  0.00           O  
HETATM   63  C40 UNL     1      -4.952  -2.081  -1.431  1.00  0.00           C  
HETATM   64  O24 UNL     1      -6.020  -2.877  -1.339  1.00  0.00           O  
HETATM   65  O25 UNL     1      -5.019  -0.863  -0.628  1.00  0.00           O  
HETATM   66  C41 UNL     1      -3.637  -2.804  -1.197  1.00  0.00           C  
HETATM   67  O26 UNL     1      -3.216  -3.357  -2.379  1.00  0.00           O  
HETATM   68  O27 UNL     1      -3.641  -3.659  -0.134  1.00  0.00           O  
HETATM   69  H1  UNL     1      -1.227   0.975   0.158  1.00  0.00           H  
HETATM   70  H2  UNL     1       1.165   2.720  -0.388  1.00  0.00           H  
HETATM   71  H3  UNL     1      -2.850   4.598   1.186  1.00  0.00           H  
HETATM   72  H4  UNL     1      -5.335   7.225   1.709  1.00  0.00           H  
HETATM   73  H5  UNL     1      -3.948   9.826   0.176  1.00  0.00           H  
HETATM   74  H6  UNL     1      -0.877   9.491  -1.357  1.00  0.00           H  
HETATM   75  H7  UNL     1      -0.257   7.157  -0.978  1.00  0.00           H  
HETATM   76  H8  UNL     1       2.212   1.289   0.584  1.00  0.00           H  
HETATM   77  H9  UNL     1       2.100  -0.587   2.829  1.00  0.00           H  
HETATM   78  H10 UNL     1       2.749   0.949   3.308  1.00  0.00           H  
HETATM   79  H11 UNL     1       5.795   1.256  -1.317  1.00  0.00           H  
HETATM   80  H12 UNL     1       7.730   0.028  -4.048  1.00  0.00           H  
HETATM   81  H13 UNL     1       7.448  -1.915  -4.294  1.00  0.00           H  
HETATM   82  H14 UNL     1       5.666  -4.349  -2.837  1.00  0.00           H  
HETATM   83  H15 UNL     1       0.653  -4.232   0.500  1.00  0.00           H  
HETATM   84  H16 UNL     1       0.851  -6.133   1.837  1.00  0.00           H  
HETATM   85  H17 UNL     1       4.079  -6.512   2.348  1.00  0.00           H  
HETATM   86  H18 UNL     1       6.352  -3.043   0.187  1.00  0.00           H  
HETATM   87  H19 UNL     1       1.684   0.696  -0.732  1.00  0.00           H  
HETATM   88  H20 UNL     1      -0.446   0.322   1.412  1.00  0.00           H  
HETATM   89  H21 UNL     1      -2.288  -1.139   3.865  1.00  0.00           H  
HETATM   90  H22 UNL     1      -4.183  -0.355   4.996  1.00  0.00           H  
HETATM   91  H23 UNL     1      -6.577   0.105   2.735  1.00  0.00           H  
HETATM   92  H24 UNL     1      -1.669  -2.381  -0.757  1.00  0.00           H  
HETATM   93  H25 UNL     1      -3.216  -0.599  -4.009  1.00  0.00           H  
HETATM   94  H26 UNL     1      -5.886  -3.834  -1.261  1.00  0.00           H  
HETATM   95  H27 UNL     1      -3.925  -3.706  -2.952  1.00  0.00           H  
HETATM   96  H28 UNL     1      -3.214  -4.513  -0.387  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   59
CONECT    3    4
CONECT    4    5   45   69
CONECT    5    6   18   70
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   17
CONECT   10   11   71
CONECT   11   12   13   13
CONECT   12   72
CONECT   13   14   15
CONECT   14   73
CONECT   15   16   17   17
CONECT   16   74
CONECT   17   75
CONECT   18   19
CONECT   19   20   46   76
CONECT   20   21   77   78
CONECT   21   22
CONECT   22   23   23   24
CONECT   24   25   25   32
CONECT   25   26   79
CONECT   26   27   28   28
CONECT   27   80
CONECT   28   29   30
CONECT   29   81
CONECT   30   31   32   32
CONECT   31   82
CONECT   32   33
CONECT   33   34   34   40
CONECT   34   35   42
CONECT   35   36   36   83
CONECT   36   37   38
CONECT   37   84
CONECT   38   39   40   40
CONECT   39   85
CONECT   40   41
CONECT   41   86
CONECT   42   43   43   44
CONECT   44   45
CONECT   45   46   87
CONECT   46   47   88
CONECT   47   48
CONECT   48   49   49   50
CONECT   50   51   51   57
CONECT   51   52   89
CONECT   52   53   54   54
CONECT   53   90
CONECT   54   55   56
CONECT   55   91
CONECT   56   57   57   65
CONECT   57   58
CONECT   58   59   66   92
CONECT   59   60   60
CONECT   60   61   93
CONECT   61   62   62   63
CONECT   63   64   65   66
CONECT   64   94
CONECT   66   67   68
CONECT   67   95
CONECT   68   96
END

HMDB0037384
     RDKit          3D
Granatin B
 96104  0  0  0  0  0  0  0  0999 V2000
   -1.1008    0.2510   -3.6459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4943    0.2490   -2.3684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    1.2779   -1.7250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3096    1.1825   -0.5311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2909    2.3599    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6580    3.3880    0.3885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4936    4.6689   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    4.9075   -0.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    5.7482    0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6390    5.5779    0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5081    6.6381    0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6960    6.4483    1.6052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2091    7.8928    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400    8.8981    0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0321    8.0731   -0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7360    9.3182   -0.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909    7.0054   -0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767    2.0677    1.5109 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5163    0.8892    1.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4978    0.3950    2.3652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6190   -0.0689    1.6380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3694    0.3163    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8321    1.5689    0.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7809   -0.4930   -0.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6469    0.1646   -1.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586   -0.4180   -2.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1936    0.3513   -3.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1598   -1.7626   -2.6819 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8371   -2.4584   -3.7189 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182   -2.4870   -1.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2169   -3.8229   -2.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6030   -1.8431   -0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -2.8291   -0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2804   -2.9335   -0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236   -4.0395    0.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4699   -4.9525    1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8382   -6.0269    1.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266   -4.8227    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5730   -5.7695    1.8829 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4304   -3.7832    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8332   -3.7655    0.6095 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3310   -2.2002   -1.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596   -3.0199   -1.8413 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8592   -0.9526   -1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7096    0.1217   -0.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752   -0.1356    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3854   -1.3989    1.3845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8292   -1.8948    1.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6821   -2.9378    2.6344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905   -1.4236    1.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8328   -1.0614    2.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253   -0.6465    2.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7127   -0.2989    4.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8335   -0.5814    1.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1770   -0.1420    1.8452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799   -0.9167    0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9275   -1.3446    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5494   -1.6937   -0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4456   -0.7824   -1.9873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3951   -0.8979   -2.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7209   -1.4393   -2.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6447   -1.4155   -3.5819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9522   -2.0811   -1.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0202   -2.8765   -1.3393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0186   -0.8635   -0.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6374   -2.8039   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2163   -3.3568   -2.3788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6410   -3.6587   -0.1343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2267    0.9754    0.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1646    2.7201   -0.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8504    4.5979    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3352    7.2250    1.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9475    9.8262    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8770    9.4912   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566    7.1572   -0.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2121    1.2891    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004   -0.5871    2.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7488    0.9486    3.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7953    1.2557   -1.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7299    0.0275   -4.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4484   -1.9150   -4.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6657   -4.3487   -2.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526   -4.2318    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511   -6.1331    1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0787   -6.5118    2.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3517   -3.0431    0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837    0.6964   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4464    0.3220    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878   -1.1391    3.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826   -0.3548    4.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5773    0.1053    2.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6685   -2.3808   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -0.5986   -4.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8862   -3.8338   -1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246   -3.7059   -2.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -4.5131   -0.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  5 18  1  0
 18 19  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,16,17,18,21,22,23,34,35,39,39-Undecahydroxy-2,5,13,26,31-pentaoxo-6,9,12,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁸.0¹⁰,²⁹.0¹⁴,¹⁹.0²⁰,²⁵.0³²,³⁷]tetraconta-3,14,16,18,20,22,24,32,34,36-decaen-8-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₄₁H₂₈O₂₇

Average Molecular Weight

952.6448

Monoisotopic Molecular Weight

952.08179569

IUPAC Name

1,16,17,18,21,22,23,34,35,39,39-undecahydroxy-2,5,13,26,31-pentaoxo-6,9,12,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁸.0¹⁰,²⁹.0¹⁴,¹⁹.0²⁰,²⁵.0³²,³⁷]tetraconta-3,14,16,18,20,22,24,32,34,36-decaen-8-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

77322-54-4

SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC3C2OC(=O)C2=CC(O)=C(O)C4=C2C2C(=CC(=O)C(O)(O4)C2(O)O)C(=O)OC13

InChI Identifier

InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-37(57)11-5-17(46)27(51)31-22(11)23-12(38(58)66-33)6-19(47)41(61,68-31)40(23,59)60)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2

InChI Key

OYPBFXPEIVEPRY-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037384)
Cytoplasm (HMDB: HMDB0037384)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037384)

Source

Exogenous

Food

Food (HMDB: HMDB0037384)

Fruit

Tropical fruit

Pomegranate (FooDB: FOOD00151)

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0037384)

Not Available

Nutrient (HMDB: HMDB0037384)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	285 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.7 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.2	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.65	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	22	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	450.25 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	210.56 m³·mol⁻¹	ChemAxon
Polarizability	84.33 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
DeepCCS	[M-2H]-	311.094	30932474
DeepCCS	[M+Na]+	284.998	30932474
AllCCS	[M+H]+	267.9	32859911
AllCCS	[M+H-H2O]+	268.3	32859911
AllCCS	[M+NH4]+	267.3	32859911
AllCCS	[M+Na]+	267.2	32859911
AllCCS	[M-H]-	267.1	32859911
AllCCS	[M+Na-2H]-	270.7	32859911
AllCCS	[M+HCOO]-	274.8	32859911

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 - Granatin B 10V, Positive-QTOF	splash10-0uk9-0902002102-9ce298519d685ec06419	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 20V, Positive-QTOF	splash10-0udi-0910000101-967e080b1159e99e9c63	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 40V, Positive-QTOF	splash10-0fki-0249000000-a3efd189e07782ad7754	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 10V, Negative-QTOF	splash10-0uxr-0900000206-d53825a89fd872a09745	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 20V, Negative-QTOF	splash10-014i-0900001402-ed294724b96389864aaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 40V, Negative-QTOF	splash10-0693-1975000200-7df866c31c90a2dfd3b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 10V, Positive-QTOF	splash10-0ue9-0000000609-2641da5ba2dcdb8d3bc0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 20V, Positive-QTOF	splash10-0uej-2900000666-ff3a2263668fdf34bacc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 40V, Positive-QTOF	splash10-0kar-0100000911-c590af1cbb8730526dce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 10V, Negative-QTOF	splash10-0ue9-0500000609-44bd568f5a7e308c0971	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 20V, Negative-QTOF	splash10-0udi-0700000339-73ba405cc9423c986c50	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granatin B 40V, Negative-QTOF	splash10-0fr5-4200000942-3b6cfba9aeda744c97f5	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

FDB016424

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Granatin B

METLIN ID

Not Available

PubChem Compound

131752181

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.. .

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

Granatin B → 1,8,16,17,18,21,22,23,34,35,39,39-dodecahydroxy-6,9,12,27,30,40-hexaoxaoctacyclo[34.3.1.0⁴,³⁸.0⁷,²⁸.0¹⁰,²⁹.0¹⁴,¹⁹.0²⁰,²⁵.0³²,³⁷]tetraconta-3,14,16,18,20,22,24,32,34,36-decaene-2,5,13,26,31-pentone	details

Showing metabocard for Granatin B (HMDB0037384)

MOL for HMDB0037384 (Granatin B)

3D MOL for HMDB0037384 (Granatin B)

3D SDF for HMDB0037384 (Granatin B)

3D-SDF for HMDB0037384 (Granatin B)

PDB for HMDB0037384 (Granatin B)

3D PDB for HMDB0037384 (Granatin B)

SMILES for HMDB0037384 (Granatin B)

INCHI for HMDB0037384 (Granatin B)

Structure for HMDB0037384 (Granatin B)

3D Structure for HMDB0037384 (Granatin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra

Enzymes

Reactions