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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:53 UTC

Update Date

2022-03-07 02:52:37 UTC

HMDB ID

HMDB0030602

Secondary Accession Numbers

HMDB30602

Metabolite Identification

Common Name

Vescalagin

Description

Vescalagin, also known as vescalene or castalagin, 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. Castalagin thus forms from a pentagalloyl-glucose structure. After conversion of casuarictin to pedunculagin, the pyranose ring of the glucose opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, vescalagin and vescalin forms. Vescalagin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, vescalagin has been detected, but not quantified in, a few different foods, such as european chestnuts, nuts, and pomegranates. This could make vescalagin a potential biomarker for the consumption of these foods. Vescalagin is one of the most abundant ellagitannins extracted from oak wood using white wine. Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides. During aging of alcohols in oak barrels, vescalagin can be extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin II and casuarictin formations). Castalagin and vescalagin (1,2,3,5-nonahydroxytriphenoyl-4,6-hexahydroxydiphenoyl-glucoses) can be further polymerized in their corresponding dimers roburin A and roburin D, and 33-carboxy-33-deoxyvescalagin. Castalagin is the (33beta)-isomer of vescalagin. Grandinin is a castalagin glycoside by binding of the pentose lyxose. The flavono-ellagitannin known as acutissimin A is created when the oak tannin vescalagin interacts with a flavonoid in wine.

Structure

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


  Mrv0541 02241217182D          

 67 75  0  0  0  0            999 V2000
   -3.1597   -4.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034   -3.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5034   -3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -2.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -2.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1081   -3.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8618   -4.6378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8987    3.3238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597    2.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597    2.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9805    1.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853    4.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4214    3.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7644    2.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927    2.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5853    1.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718    2.0105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6007    1.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255    1.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1900    0.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469    0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752   -0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9436    4.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6974    3.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6154    2.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4362    2.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108    2.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9135    2.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1597    3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    3.3238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    1.1897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692    0.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2867   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2867   -0.8614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3692   -1.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081   -0.9439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329    2.0105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873    1.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2048    2.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436    3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799    3.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543    4.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    4.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    5.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108    4.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7644    3.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5853    3.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315    4.5553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927   -3.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3543   -3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081   -2.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873   -2.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3692   -2.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -3.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -3.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0255   -4.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -4.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1597   -2.0111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389   -1.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1745   -1.0258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181   -0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1900    0.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3537    0.9433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    1.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8315    0.9433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7644   -4.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -5.1299    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 66  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 59  1  0  0  0  0
  5  6  1  0  0  0  0
  5 53  1  0  0  0  0
  6  7  1  0  0  0  0
  6 66  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  0  0  0  0
 10 11  1  0  0  0  0
 10 16  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 40  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 32  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 43  1  0  0  0  0
 25 26  1  0  0  0  0
 25 39  1  0  0  0  0
 26 27  2  0  0  0  0
 26 46  1  0  0  0  0
 27 28  1  0  0  0  0
 27 64  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 47  1  0  0  0  0
 31 32  1  0  0  0  0
 31 38  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 62  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 52  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 43 44  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 50 55  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 57  1  0  0  0  0
 55 56  1  0  0  0  0
 58 59  2  0  0  0  0
 59 60  1  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  2  0  0  0  0
 66 67  1  0  0  0  0
M  END

HMDB0030602
     RDKit          3D
Vescalagin
 93101  0  0  0  0  0  0  0  0999 V2000
    4.7554   -1.8695   -2.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249   -1.0337   -1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9119   -0.6549   -2.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868   -1.0287   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4518   -0.5513   -2.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909   -1.5588   -1.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566   -2.6214   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7972   -2.8733   -0.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2899   -3.6244   -0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664   -4.9121   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313   -6.0008   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9329   -7.2798   -0.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8274   -5.8342    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6047   -6.9462    0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -4.5727   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7075   -4.5707    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385   -3.4215   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4415   -2.1881   -0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806   -2.3506   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0209   -3.5424   -1.7940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7073   -1.4122   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9156   -1.7004   -1.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4491   -0.2175   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4720    0.7357   -0.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2621    0.0264    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815   -0.9422    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024   -0.6582    0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -0.8891    1.9519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7091   -0.1776    0.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991    0.8119   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.7427   -1.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927    1.1344   -1.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635    1.8806   -2.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920    2.2302   -3.5351 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    2.4249   -1.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578    3.5853   -2.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735    4.1999   -1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2903    5.3714   -2.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3592    3.5877   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4773    4.1927    0.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8385    2.4313    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757    1.8846    1.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894    1.8046   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2169    0.5926    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9410   -0.6415   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537   -1.7176    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238   -1.6074    1.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3300   -2.7159    2.7378 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.3950    2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -0.1769    3.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719    0.6693    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303    1.9271    2.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397    2.0769    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9839    2.3932   -1.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    1.6224   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012    0.8705   -2.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    1.9851    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    1.4061    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5372    1.8554    1.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7653    1.3300    2.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9674    2.8488    2.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    3.2713    3.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637    3.3573    2.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850    4.3517    2.9178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    2.9222    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582    3.3076    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661    4.4568    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770   -0.5976   -4.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4833   -2.1124   -3.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748   -0.3284   -3.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979   -5.1601   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132   -7.4772   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5544   -6.8153    0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3763   -3.9003    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -3.7160   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7052   -1.1241   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3234    0.5547   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746    0.4805    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550    1.4828   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283    4.1067   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
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 66 92  1  0
 67 93  1  0
M  END


  Mrv0541 02241217182D          

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M  END
> <DATABASE_ID>
HMDB0030602

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(C=C(O)C(O)=C1O)C(=O)OC1COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)OC1C2OC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2

> <INCHI_KEY>
UDYKDZHZAKSYCO-UHFFFAOYSA-N

> <FORMULA>
C41H26O26

> <MOLECULAR_WEIGHT>
934.6295

> <EXACT_MASS>
934.071231004

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
81.95412395344825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
16

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
2.0259335789999997

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.563872995015127

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.139480581657935

> <JCHEM_PKA_STRONGEST_BASIC>
-6.177204321276062

> <JCHEM_POLAR_SURFACE_AREA>
455.1800000000001

> <JCHEM_REFRACTIVITY>
212.68650000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030602
     RDKit          3D
Vescalagin
 93101  0  0  0  0  0  0  0  0999 V2000
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    0.7488    0.7427   -1.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927    1.1344   -1.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6578    3.5853   -2.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735    4.1999   -1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3300   -2.7159    2.7378 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8777   -0.1769    3.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4303    1.9271    2.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397    2.0769    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9839    2.3932   -1.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    1.6224   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012    0.8705   -2.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    1.9851    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    1.4061    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5372    1.8554    1.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7653    1.3300    2.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9674    2.8488    2.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    3.2713    3.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637    3.3573    2.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850    4.3517    2.9178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    2.9222    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582    3.3076    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661    4.4568    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770   -0.5976   -4.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4833   -2.1124   -3.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748   -0.3284   -3.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0132   -7.4772   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5544   -6.8153    0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3763   -3.9003    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -3.7160   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7052   -1.1241   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3234    0.5547   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746    0.4805    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550    1.4828   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283    4.1067   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0923    5.7934   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9299    3.7939    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2534    2.1450    1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823   -2.7356    0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385   -3.6075    2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -0.9874    4.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4071    2.0121    3.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    1.5322    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1559    1.6735    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1505    3.9840    4.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915    4.7491    3.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545    3.5077    1.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012    5.1445    0.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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      -5.898  -8.351   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.673  -7.431   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.673  -5.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.600  -4.826   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.068  -5.439   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.068  -6.971   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.609  -8.657   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.278   6.204   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.898   5.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.898   3.907   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.430   3.447   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.826   7.737   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.520   6.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.294   5.285   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.906   3.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.826   3.140   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.374   3.753   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.988   2.680   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.914   2.221   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.221   0.995   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.448   0.384   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.060  -1.608   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.761   8.503   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.302   7.124   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.149   5.439   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.681   5.132   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.753   4.060   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.439   4.519   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.898   5.899   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.430   6.204   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.078   2.221   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.689   0.841   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.535  -0.076   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.535  -1.608   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.689  -2.375   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.068  -1.762   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.995   3.753   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.536   3.600   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.382   5.132   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.761   5.899   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.456   7.431   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.528   8.503   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.076   7.891   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.078   9.576   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -3.753   8.656   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -3.294   6.664   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -4.826   7.124   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -5.285   8.503   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       3.906  -6.206   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       2.528  -5.899   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.068  -4.367   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.536  -4.060   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -0.689  -4.979   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.078  -6.511   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       1.456  -6.971   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       1.914  -8.351   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -0.078  -8.044   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      -5.898  -3.754   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -4.366  -3.447   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -4.059  -1.915   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -2.834  -1.149   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -2.221   0.230   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -2.527   1.761   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -3.906   2.527   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      -5.285   1.761   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      -3.294  -7.891   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      -3.141  -9.576   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   66                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   59                                                  
CONECT    5    4    6   53                                                  
CONECT    6    5    7   66                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10   13                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    9   12   14                                                  
CONECT   14   13   15   40                                                  
CONECT   15   14   16   18                                                  
CONECT   16   10   15   21                                                  
CONECT   17   18                                                            
CONECT   18   15   17   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   16   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24   23   25   43                                                  
CONECT   25   24   26   39                                                  
CONECT   26   25   27   46                                                  
CONECT   27   26   28   64                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   47                                                  
CONECT   30   29                                                            
CONECT   31   32   38                                                       
CONECT   32   20   31   33                                                  
CONECT   33   32   34   62                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   52                                                  
CONECT   36   35                                                            
CONECT   37   38                                                            
CONECT   38   31   37   39                                                  
CONECT   39   25   38   40                                                  
CONECT   40   14   39   41                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   24   41   44                                                  
CONECT   44   43                                                            
CONECT   45   46                                                            
CONECT   46   26   45   47                                                  
CONECT   47   29   46   48                                                  
CONECT   48   47                                                            
CONECT   49   50                                                            
CONECT   50   49   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   35   51   53                                                  
CONECT   53    5   52   54                                                  
CONECT   54   53   55   57                                                  
CONECT   55   50   54   56                                                  
CONECT   56   55                                                            
CONECT   57   54                                                            
CONECT   58   59                                                            
CONECT   59    4   58   60                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   33   61   63                                                  
CONECT   63   62   64                                                       
CONECT   64   27   63   65                                                  
CONECT   65   64                                                            
CONECT   66    2    6   67                                                  
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  150    0
END

COMPND    HMDB0030602
HETATM    1  O1  UNL     1       4.755  -1.870  -2.091  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.825  -1.034  -1.722  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.912  -0.655  -2.658  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.687  -1.029  -3.094  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.452  -0.551  -2.294  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.091  -1.559  -1.654  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.257  -2.621  -0.916  1.00  0.00           C  
HETATM    8  O4  UNL     1       0.797  -2.873  -0.132  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.290  -3.624  -0.702  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.766  -4.912  -0.624  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.531  -6.001  -0.263  1.00  0.00           C  
HETATM   12  O5  UNL     1      -0.933  -7.280  -0.209  1.00  0.00           O  
HETATM   13  C8  UNL     1      -2.827  -5.834   0.033  1.00  0.00           C  
HETATM   14  O6  UNL     1      -3.605  -6.946   0.405  1.00  0.00           O  
HETATM   15  C9  UNL     1      -3.387  -4.573  -0.029  1.00  0.00           C  
HETATM   16  O7  UNL     1      -4.708  -4.571   0.337  1.00  0.00           O  
HETATM   17  C10 UNL     1      -2.639  -3.421  -0.411  1.00  0.00           C  
HETATM   18  C11 UNL     1      -3.441  -2.188  -0.501  1.00  0.00           C  
HETATM   19  C12 UNL     1      -4.681  -2.351  -1.097  1.00  0.00           C  
HETATM   20  O8  UNL     1      -5.021  -3.542  -1.794  1.00  0.00           O  
HETATM   21  C13 UNL     1      -5.707  -1.412  -1.117  1.00  0.00           C  
HETATM   22  O9  UNL     1      -6.916  -1.700  -1.745  1.00  0.00           O  
HETATM   23  C14 UNL     1      -5.449  -0.217  -0.493  1.00  0.00           C  
HETATM   24  O10 UNL     1      -6.472   0.736  -0.494  1.00  0.00           O  
HETATM   25  C15 UNL     1      -4.262   0.026   0.097  1.00  0.00           C  
HETATM   26  C16 UNL     1      -3.182  -0.942   0.126  1.00  0.00           C  
HETATM   27  C17 UNL     1      -1.802  -0.658   0.656  1.00  0.00           C  
HETATM   28  O11 UNL     1      -1.517  -0.889   1.952  1.00  0.00           O  
HETATM   29  O12 UNL     1      -0.709  -0.178   0.005  1.00  0.00           O  
HETATM   30  C18 UNL     1       0.299   0.812  -0.097  1.00  0.00           C  
HETATM   31  C19 UNL     1       0.749   0.743  -1.587  1.00  0.00           C  
HETATM   32  O13 UNL     1       1.993   1.134  -1.826  1.00  0.00           O  
HETATM   33  C20 UNL     1       2.964   1.881  -2.274  1.00  0.00           C  
HETATM   34  O14 UNL     1       2.992   2.230  -3.535  1.00  0.00           O  
HETATM   35  C21 UNL     1       4.112   2.425  -1.546  1.00  0.00           C  
HETATM   36  C22 UNL     1       4.658   3.585  -2.051  1.00  0.00           C  
HETATM   37  C23 UNL     1       5.773   4.200  -1.519  1.00  0.00           C  
HETATM   38  O15 UNL     1       6.290   5.371  -2.059  1.00  0.00           O  
HETATM   39  C24 UNL     1       6.359   3.588  -0.410  1.00  0.00           C  
HETATM   40  O16 UNL     1       7.477   4.193   0.133  1.00  0.00           O  
HETATM   41  C25 UNL     1       5.839   2.431   0.117  1.00  0.00           C  
HETATM   42  O17 UNL     1       6.476   1.885   1.200  1.00  0.00           O  
HETATM   43  C26 UNL     1       4.689   1.805  -0.430  1.00  0.00           C  
HETATM   44  C27 UNL     1       4.217   0.593   0.242  1.00  0.00           C  
HETATM   45  C28 UNL     1       3.941  -0.641  -0.309  1.00  0.00           C  
HETATM   46  C29 UNL     1       3.654  -1.718   0.559  1.00  0.00           C  
HETATM   47  C30 UNL     1       3.624  -1.607   1.929  1.00  0.00           C  
HETATM   48  O18 UNL     1       3.330  -2.716   2.738  1.00  0.00           O  
HETATM   49  C31 UNL     1       3.885  -0.395   2.480  1.00  0.00           C  
HETATM   50  O19 UNL     1       3.878  -0.177   3.864  1.00  0.00           O  
HETATM   51  C32 UNL     1       4.172   0.669   1.645  1.00  0.00           C  
HETATM   52  O20 UNL     1       4.430   1.927   2.240  1.00  0.00           O  
HETATM   53  C33 UNL     1      -0.240   2.077   0.199  1.00  0.00           C  
HETATM   54  O21 UNL     1      -0.984   2.393  -1.096  1.00  0.00           O  
HETATM   55  C34 UNL     1      -2.158   1.622  -1.032  1.00  0.00           C  
HETATM   56  O22 UNL     1      -2.401   0.870  -2.049  1.00  0.00           O  
HETATM   57  C35 UNL     1      -2.745   1.985   0.239  1.00  0.00           C  
HETATM   58  C36 UNL     1      -3.980   1.406   0.668  1.00  0.00           C  
HETATM   59  C37 UNL     1      -4.537   1.855   1.811  1.00  0.00           C  
HETATM   60  O23 UNL     1      -5.765   1.330   2.265  1.00  0.00           O  
HETATM   61  C38 UNL     1      -3.967   2.849   2.624  1.00  0.00           C  
HETATM   62  O24 UNL     1      -4.582   3.271   3.775  1.00  0.00           O  
HETATM   63  C39 UNL     1      -2.764   3.357   2.184  1.00  0.00           C  
HETATM   64  O25 UNL     1      -2.085   4.352   2.918  1.00  0.00           O  
HETATM   65  C40 UNL     1      -2.181   2.922   1.025  1.00  0.00           C  
HETATM   66  C41 UNL     1      -0.658   3.308   0.855  1.00  0.00           C  
HETATM   67  O26 UNL     1      -0.666   4.457   0.088  1.00  0.00           O  
HETATM   68  H1  UNL     1       1.577  -0.598  -4.153  1.00  0.00           H  
HETATM   69  H2  UNL     1       1.483  -2.112  -3.273  1.00  0.00           H  
HETATM   70  H3  UNL     1      -0.275  -0.328  -3.189  1.00  0.00           H  
HETATM   71  H4  UNL     1       0.298  -5.160  -0.841  1.00  0.00           H  
HETATM   72  H5  UNL     1       0.013  -7.477  -0.413  1.00  0.00           H  
HETATM   73  H6  UNL     1      -4.554  -6.815   0.621  1.00  0.00           H  
HETATM   74  H7  UNL     1      -5.376  -3.900   0.507  1.00  0.00           H  
HETATM   75  H8  UNL     1      -5.875  -3.716  -2.235  1.00  0.00           H  
HETATM   76  H9  UNL     1      -7.705  -1.124  -1.827  1.00  0.00           H  
HETATM   77  H10 UNL     1      -7.323   0.555  -0.919  1.00  0.00           H  
HETATM   78  H11 UNL     1       1.175   0.481   0.514  1.00  0.00           H  
HETATM   79  H12 UNL     1       0.055   1.483  -2.103  1.00  0.00           H  
HETATM   80  H13 UNL     1       4.228   4.107  -2.928  1.00  0.00           H  
HETATM   81  H14 UNL     1       7.092   5.793  -1.658  1.00  0.00           H  
HETATM   82  H15 UNL     1       7.930   3.794   0.926  1.00  0.00           H  
HETATM   83  H16 UNL     1       7.253   2.145   1.706  1.00  0.00           H  
HETATM   84  H17 UNL     1       3.482  -2.736   0.185  1.00  0.00           H  
HETATM   85  H18 UNL     1       3.138  -3.608   2.299  1.00  0.00           H  
HETATM   86  H19 UNL     1       3.665  -0.987   4.461  1.00  0.00           H  
HETATM   87  H20 UNL     1       4.407   2.012   3.245  1.00  0.00           H  
HETATM   88  H21 UNL     1      -1.057   1.532   0.967  1.00  0.00           H  
HETATM   89  H22 UNL     1      -6.156   1.673   3.107  1.00  0.00           H  
HETATM   90  H23 UNL     1      -4.151   3.984   4.339  1.00  0.00           H  
HETATM   91  H24 UNL     1      -2.391   4.749   3.764  1.00  0.00           H  
HETATM   92  H25 UNL     1      -0.255   3.508   1.851  1.00  0.00           H  
HETATM   93  H26 UNL     1      -0.001   5.144   0.382  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   45
CONECT    3    4
CONECT    4    5   68   69
CONECT    5    6   31   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   18
CONECT   18   19   19   26
CONECT   19   20   21
CONECT   20   75
CONECT   21   22   23   23
CONECT   22   76
CONECT   23   24   25
CONECT   24   77
CONECT   25   26   26   58
CONECT   26   27
CONECT   27   28   28   29
CONECT   29   30
CONECT   30   31   53   78
CONECT   31   32   79
CONECT   32   33
CONECT   33   34   34   35
CONECT   35   36   36   43
CONECT   36   37   80
CONECT   37   38   39   39
CONECT   38   81
CONECT   39   40   41
CONECT   40   82
CONECT   41   42   43   43
CONECT   42   83
CONECT   43   44
CONECT   44   45   45   51
CONECT   45   46
CONECT   46   47   47   84
CONECT   47   48   49
CONECT   48   85
CONECT   49   50   51   51
CONECT   50   86
CONECT   51   52
CONECT   52   87
CONECT   53   54   66   88
CONECT   54   55
CONECT   55   56   56   57
CONECT   57   58   58   65
CONECT   58   59
CONECT   59   60   61   61
CONECT   60   89
CONECT   61   62   63
CONECT   62   90
CONECT   63   64   65   65
CONECT   64   91
CONECT   65   66
CONECT   66   67   92
CONECT   67   93
END

HMDB0030602
     RDKit          3D
Vescalagin
 93101  0  0  0  0  0  0  0  0999 V2000
    4.7554   -1.8695   -2.0905 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8249   -1.0337   -1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9119   -0.6549   -2.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868   -1.0287   -3.0941 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4518   -0.5513   -2.2941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0909   -1.5588   -1.6543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2566   -2.6214   -0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7972   -2.8733   -0.1324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2899   -3.6244   -0.7022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7664   -4.9121   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5313   -6.0008   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9329   -7.2798   -0.2094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8274   -5.8342    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6047   -6.9462    0.4052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -4.5727   -0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7075   -4.5707    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6385   -3.4215   -0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4415   -2.1881   -0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6806   -2.3506   -1.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0209   -3.5424   -1.7940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7073   -1.4122   -1.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9156   -1.7004   -1.7452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4491   -0.2175   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4720    0.7357   -0.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2621    0.0264    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815   -0.9422    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024   -0.6582    0.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -0.8891    1.9519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7091   -0.1776    0.0055 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991    0.8119   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488    0.7427   -1.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9927    1.1344   -1.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635    1.8806   -2.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9920    2.2302   -3.5351 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124    2.4249   -1.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578    3.5853   -2.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7735    4.1999   -1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2903    5.3714   -2.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3592    3.5877   -0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4773    4.1927    0.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8385    2.4313    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757    1.8846    1.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894    1.8046   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2169    0.5926    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9410   -0.6415   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537   -1.7176    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238   -1.6074    1.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3300   -2.7159    2.7378 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8852   -0.3950    2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8777   -0.1769    3.8642 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719    0.6693    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4303    1.9271    2.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2397    2.0769    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9839    2.3932   -1.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    1.6224   -1.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4012    0.8705   -2.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    1.9851    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    1.4061    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5372    1.8554    1.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7653    1.3300    2.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9674    2.8488    2.6241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5819    3.2713    3.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7637    3.3573    2.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850    4.3517    2.9178 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811    2.9222    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582    3.3076    0.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6661    4.4568    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770   -0.5976   -4.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4833   -2.1124   -3.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748   -0.3284   -3.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2979   -5.1601   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0132   -7.4772   -0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5544   -6.8153    0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3763   -3.9003    0.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8754   -3.7160   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7052   -1.1241   -1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3234    0.5547   -0.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1746    0.4805    0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550    1.4828   -2.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2283    4.1067   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0923    5.7934   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9299    3.7939    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2534    2.1450    1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823   -2.7356    0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385   -3.6075    2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -0.9874    4.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4071    2.0121    3.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0569    1.5322    0.9670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1559    1.6735    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1505    3.9840    4.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915    4.7491    3.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545    3.5077    1.8509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012    5.1445    0.3816 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
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 39 40  1  0
 39 41  1  0
 41 42  1  0
 41 43  2  0
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 49 51  2  0
 51 52  1  0
 30 53  1  0
 53 54  1  0
 54 55  1  0
 55 56  2  0
 55 57  1  0
 57 58  2  0
 58 59  1  0
 59 60  1  0
 59 61  2  0
 61 62  1  0
 61 63  1  0
 63 64  1  0
 63 65  2  0
 65 66  1  0
 66 67  1  0
 45  2  1  0
 66 53  1  0
 31  5  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Vescalagin, (33beta)-isomer	HMDB
Vescalene	HMDB
Castalagin	HMDB
Vescalin	HMDB
Vescalagin	MeSH

Chemical Formula

C₄₁H₂₆O₂₆

Average Molecular Weight

934.6295

Monoisotopic Molecular Weight

934.071231004

IUPAC Name

7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

Traditional Name

CAS Registry Number

36001-47-5

SMILES

OC1C2OC(=O)C3=C(C(O)=C(O)C(O)=C13)C1=C3C(=C(O)C(O)=C1O)C1=C(C=C(O)C(O)=C1O)C(=O)OC1COC(=O)C4=C(C(O)=C(O)C(O)=C4)C4=C(C=C(O)C(O)=C4O)C(=O)OC1C2OC3=O

InChI Identifier

InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2

InChI Key

UDYKDZHZAKSYCO-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

Substituents

Hydrolyzable tannin
Pentacarboxylic acid or derivatives
Gallic acid or derivatives
Benzopyran
Isochromane
2-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030602)

Cellular substructure

Membrane (HMDB: HMDB0030602)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030602)

Source

Exogenous

Food

Food (HMDB: HMDB0030602)

Nut

Nuts (FooDB: FOOD00869)

Endogenous

Plant

Plant (HMDB: HMDB0030602)

Not Available

Nutrient (HMDB: HMDB0030602)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 °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	5.79 g/L	ALOGPS
logP	2.74	ALOGPS
logP	2.03	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	16	ChemAxon
Polar Surface Area	455.18 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	212.69 m³·mol⁻¹	ChemAxon
Polarizability	81.95 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]-	308.496	30932474
DeepCCS	[M+Na]+	282.516	30932474
AllCCS	[M+H]+	276.2	32859911
AllCCS	[M+H-H2O]+	276.3	32859911
AllCCS	[M+NH4]+	276.0	32859911
AllCCS	[M+Na]+	275.9	32859911
AllCCS	[M-H]-	289.3	32859911
AllCCS	[M+Na-2H]-	293.4	32859911
AllCCS	[M+HCOO]-	298.0	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 - Vescalagin 10V, Positive-QTOF	splash10-00kr-0007012009-9da62c3e2ae215440173	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 20V, Positive-QTOF	splash10-0670-0033020019-e883a97efaffe1502c97	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 40V, Positive-QTOF	splash10-004j-0094821300-1e5e799461b5c0ffd72e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 10V, Negative-QTOF	splash10-001i-0000000039-cd0022e4de6c8b55d0f3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 20V, Negative-QTOF	splash10-015i-0110022298-a10d22f9bbb15c24e4f7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 40V, Negative-QTOF	splash10-01di-3961020052-0c74da69e60fd6821efd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 10V, Positive-QTOF	splash10-000i-0000000009-00a3c50acb8675dad0f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 20V, Positive-QTOF	splash10-000i-0000000009-f51a832392fb6922f744	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 40V, Positive-QTOF	splash10-0040-0000000090-a07de417abcfa5eca9d9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 10V, Negative-QTOF	splash10-001i-0000000009-3f4336f1c91b5b42acb6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 20V, Negative-QTOF	splash10-001i-0000000039-96f075acd790a775fd0a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vescalagin 40V, Negative-QTOF	splash10-002b-0000000091-28610e79b51e05a00230	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB018931

KNApSAcK ID

Not Available

Chemspider ID

147097

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Castalagin

METLIN ID

Not Available

PubChem Compound

168165

PDB ID

Not Available

ChEBI ID

704619

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 Vescalagin (HMDB0030602)

MOL for HMDB0030602 (Vescalagin)

3D MOL for HMDB0030602 (Vescalagin)

3D SDF for HMDB0030602 (Vescalagin)

3D-SDF for HMDB0030602 (Vescalagin)

PDB for HMDB0030602 (Vescalagin)

3D PDB for HMDB0030602 (Vescalagin)

SMILES for HMDB0030602 (Vescalagin)

INCHI for HMDB0030602 (Vescalagin)

Structure for HMDB0030602 (Vescalagin)

3D Structure for HMDB0030602 (Vescalagin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra