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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:39:47 UTC

Update Date

2022-03-07 02:56:08 UTC

HMDB ID

HMDB0039268

Secondary Accession Numbers

HMDB39268

Metabolite Identification

Common Name

Heterophylliin E

Description

Heterophylliin E 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. Heterophylliin E is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, heterophylliin e has been detected, but not quantified in, nuts. This could make heterophylliin e a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 09121200392D          

 65 72  0  0  0  0            999 V2000
    0.6640    0.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    0.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4867   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640   -1.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747   -1.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5383   -2.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438   -3.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -2.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -1.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790    1.5499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790    0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832    0.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790   -0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790   -2.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -2.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -3.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790   -3.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8790   -4.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3345    0.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6386    0.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6386   -0.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3345   -0.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3345   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6386   -2.4993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6386   -3.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3345   -3.7017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -2.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -1.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8790   -1.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -1.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3345   -1.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3345   -3.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -2.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9421   -3.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9421   -4.0183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968    1.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398    0.9172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7524    3.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    2.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195    2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605    1.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7909    2.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706    3.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7909    3.8280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313    3.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743    4.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313    0.9172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743    1.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0313    2.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743    3.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968    3.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7398    2.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    2.3726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -2.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6135   -1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2463   -1.1074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    0.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605    1.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747   -0.6641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747    0.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3605   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5504   -0.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -1.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0564   -1.9297    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 61  1  0  0  0  0
  3  4  1  0  0  0  0
  3 57  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 62  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 21  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 64  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  2  0  0  0  0
 15 16  2  0  0  0  0
 15 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 28 29  2  0  0  0  0
 28 35  1  0  0  0  0
 29 30  1  0  0  0  0
 29 56  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 37 49  2  0  0  0  0
 37 53  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 44  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 59  1  0  0  0  0
 43 44  2  0  0  0  0
 43 50  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 51  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  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
 55 56  2  0  0  0  0
 56 57  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
M  END

HMDB0039268
     RDKit          3D
Heterophylliin E
 93100  0  0  0  0  0  0  0  0999 V2000
    0.4439    5.3099    2.8816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327    5.5999    1.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    4.5398    0.7927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119    3.1733    1.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    2.7259    1.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062    1.5282    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7899    0.4448    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -0.2359    1.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017   -0.0607    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0410    0.6843    1.4916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4784   -0.5983   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3403    0.2040   -1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452   -0.1749   -2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7951    0.6554   -3.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6763   -1.4843   -2.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2457   -1.8833   -3.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8276   -2.3008   -2.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6242   -3.5610   -2.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2229   -1.8682   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2912   -2.8677   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098   -2.7792   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -3.8880    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9332   -5.0500    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -6.0910    1.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717   -5.1263    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9718   -6.2635    0.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9166   -4.0497    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3186   -4.1966   -0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0257   -1.7081   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0327   -2.2502   -1.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646   -0.4090   -0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210    0.8344   -0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7868    0.9548    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966    0.3392   -0.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6540   -0.5944   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7233   -0.9289    1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -1.2249   -1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4994   -0.0695   -1.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3953    0.0390   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8329    1.0574    0.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6395   -1.3611   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6418   -1.8871    0.6219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7307   -3.1619    0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6901   -3.6677    1.5362 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7071   -4.0071    0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7533   -5.3670    0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7536   -6.2271    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8399   -7.5866    0.6635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6878   -5.6930   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506   -6.4741   -0.7620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -4.3189   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990   -3.7578   -1.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505   -3.4608   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634   -2.1062   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    2.4461    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569    2.5612    0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789    6.9918    1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107    8.0021    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    9.3334    1.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   10.3374    2.7223 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    9.6927    0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0344   11.0134    0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    8.6615   -0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2223    8.9824   -1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    7.3543   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    3.1887    2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    1.6171    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.2279    1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122    0.9544    2.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5489    1.2305   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9952    1.5806   -2.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6977   -2.0010   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0502   -3.8787   -3.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2023   -3.9073    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -6.9584    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -7.0420    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7981   -5.0190    0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    1.5080   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8967    0.5814    1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -1.6180   -2.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263   -0.4047   -2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.8287   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6212   -5.7348    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -8.2649    0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -7.4599   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006   -4.2559   -1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197    2.8621   -0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4449    1.9143    1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    7.8192    3.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   11.3148    2.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114   11.8140    0.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113    8.2313   -2.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 09121200392D          

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M  END
> <DATABASE_ID>
HMDB0039268

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C1OC(=O)C1CC(=O)C2=C1C1=C(C=C(O)C(O)=C1O)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C40H28O25/c41-13-1-8(2-14(42)24(13)47)35(55)65-40-31(54)34(64-39(59)12-6-18(46)32-23(12)22-11(37(57)62-32)5-17(45)27(50)30(22)53)33-19(61-40)7-60-36(56)9-3-15(43)25(48)28(51)20(9)21-10(38(58)63-33)4-16(44)26(49)29(21)52/h1-5,12,19,31,33-34,40-45,47-54H,6-7H2

> <INCHI_KEY>
AQPVGKAQOQGNBT-UHFFFAOYSA-N

> <FORMULA>
C40H28O25

> <MOLECULAR_WEIGHT>
908.6353

> <EXACT_MASS>
908.091966446

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
79.09440970934097

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-13-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-11-yl 7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylate

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.174049889333333

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.388910599684263

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.584351111961479

> <JCHEM_PKA_STRONGEST_BASIC>
-6.1733818880770075

> <JCHEM_POLAR_SURFACE_AREA>
420.79

> <JCHEM_REFRACTIVITY>
205.8342

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-13-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-11-yl 7,8,9-trihydroxy-3,5-dioxo-1H,2H-cyclopenta[c]isochromene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039268
     RDKit          3D
Heterophylliin E
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    2.6506   -6.4741   -0.7620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -4.3189   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990   -3.7578   -1.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505   -3.4608   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634   -2.1062   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    2.4461    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569    2.5612    0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789    6.9918    1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107    8.0021    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    9.3334    1.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   10.3374    2.7223 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    9.6927    0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0344   11.0134    0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    8.6615   -0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2223    8.9824   -1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    7.3543   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    3.1887    2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    1.6171    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.2279    1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122    0.9544    2.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5489    1.2305   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9952    1.5806   -2.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6977   -2.0010   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0502   -3.8787   -3.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2023   -3.9073    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -6.9584    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -7.0420    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7981   -5.0190    0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    1.5080   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8967    0.5814    1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -1.6180   -2.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263   -0.4047   -2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.8287   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6212   -5.7348    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -8.2649    0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -7.4599   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006   -4.2559   -1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197    2.8621   -0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4449    1.9143    1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    7.8192    3.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   11.3148    2.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114   11.8140    0.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113    8.2313   -2.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039    6.6014   -0.8284 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  1  0
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  9 10  2  0
  9 11  1  0
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 65 93  1  0
M  END

HEADER    PROTEIN                                 12-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-12         0                                  
HETATM    1  O   UNK     0       1.239   1.358   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.239   0.058   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.775  -1.476   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.239  -3.130   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.886  -3.130   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.005  -4.548   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.948  -5.846   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.540  -4.548   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.540  -3.130   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -5.374   2.893   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.374   1.358   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.075   0.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.075  -1.004   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.374  -1.713   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.374  -3.839   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.075  -4.548   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.075  -6.083   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.374  -6.910   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.374  -8.446   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -8.091   1.358   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -6.792   0.531   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.792  -1.004   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.091  -1.831   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.091  -3.956   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -6.792  -4.665   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.792  -6.083   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.091  -6.910   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.074  -5.138   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.074  -3.602   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.374  -2.775   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.792  -3.602   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.091  -2.775   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.091  -5.965   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.792  -5.138   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.492  -5.965   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.492  -7.501   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.421   3.130   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.248   1.712   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.138   6.201   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -3.721   5.492   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.956   3.956   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.540   3.248   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.476   4.429   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.185   5.729   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -1.476   7.146   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       0.058   7.146   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       0.885   8.446   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       0.058   1.712   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       0.885   3.130   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.058   4.429   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.885   5.729   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.421   5.846   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.248   4.429   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       4.783   4.429   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       1.948  -4.430   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       3.012  -3.484   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       4.193  -2.067   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      -3.721   1.358   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -2.540   2.066   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -0.886  -1.240   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0      -0.886   0.058   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -2.540  -1.476   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      -2.894  -0.296   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      -4.075  -2.185   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      -3.839  -3.602   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   61                                                  
CONECT    3    2    4   57                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   62                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   64                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16   25                                                  
CONECT   16    8   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   11   20   22                                                  
CONECT   22   14   21   23                                                  
CONECT   23   22                                                            
CONECT   24   25                                                            
CONECT   25   15   24   26                                                  
CONECT   26   18   25   27                                                  
CONECT   27   26                                                            
CONECT   28   29   35                                                       
CONECT   29   28   30   56                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   34                                                  
CONECT   32   31                                                            
CONECT   33   34                                                            
CONECT   34   31   33   35                                                  
CONECT   35   28   34   36                                                  
CONECT   36   35                                                            
CONECT   37   38   49   53                                                  
CONECT   38   37                                                            
CONECT   39   40                                                            
CONECT   40   39   41   44                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   59                                                  
CONECT   43   42   44   50                                                  
CONECT   44   40   43   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   51                                                  
CONECT   47   46                                                            
CONECT   48   49                                                            
CONECT   49   37   48   50                                                  
CONECT   50   43   49   51                                                  
CONECT   51   46   50   52                                                  
CONECT   52   51   53                                                       
CONECT   53   37   52   54                                                  
CONECT   54   53                                                            
CONECT   55   56                                                            
CONECT   56   29   55   57                                                  
CONECT   57    3   56                                                       
CONECT   58   59                                                            
CONECT   59   42   58   60                                                  
CONECT   60   59   61                                                       
CONECT   61    2   60   62                                                  
CONECT   62    5   61   63                                                  
CONECT   63   62   64                                                       
CONECT   64   13   63   65                                                  
CONECT   65   64                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  144    0
END

COMPND    HMDB0039268
HETATM    1  O1  UNL     1       0.444   5.310   2.882  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.233   5.600   1.676  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.055   4.540   0.793  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.112   3.173   1.237  1.00  0.00           C  
HETATM    5  O3  UNL     1      -1.177   2.726   1.202  1.00  0.00           O  
HETATM    6  C3  UNL     1      -1.506   1.528   0.774  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.790   0.445   1.816  1.00  0.00           C  
HETATM    8  O4  UNL     1      -2.958  -0.236   1.569  1.00  0.00           O  
HETATM    9  C5  UNL     1      -4.102  -0.061   0.909  1.00  0.00           C  
HETATM   10  O5  UNL     1      -5.041   0.684   1.492  1.00  0.00           O  
HETATM   11  C6  UNL     1      -4.478  -0.598  -0.407  1.00  0.00           C  
HETATM   12  C7  UNL     1      -5.340   0.204  -1.159  1.00  0.00           C  
HETATM   13  C8  UNL     1      -5.945  -0.175  -2.323  1.00  0.00           C  
HETATM   14  O6  UNL     1      -6.795   0.655  -3.041  1.00  0.00           O  
HETATM   15  C9  UNL     1      -5.676  -1.484  -2.801  1.00  0.00           C  
HETATM   16  O7  UNL     1      -6.246  -1.883  -3.922  1.00  0.00           O  
HETATM   17  C10 UNL     1      -4.828  -2.301  -2.083  1.00  0.00           C  
HETATM   18  O8  UNL     1      -4.624  -3.561  -2.605  1.00  0.00           O  
HETATM   19  C11 UNL     1      -4.223  -1.868  -0.895  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.291  -2.868  -0.317  1.00  0.00           C  
HETATM   21  C13 UNL     1      -1.910  -2.779  -0.096  1.00  0.00           C  
HETATM   22  C14 UNL     1      -1.273  -3.888   0.491  1.00  0.00           C  
HETATM   23  C15 UNL     1      -1.933  -5.050   0.852  1.00  0.00           C  
HETATM   24  O9  UNL     1      -1.196  -6.091   1.431  1.00  0.00           O  
HETATM   25  C16 UNL     1      -3.272  -5.126   0.626  1.00  0.00           C  
HETATM   26  O10 UNL     1      -3.972  -6.264   0.967  1.00  0.00           O  
HETATM   27  C17 UNL     1      -3.917  -4.050   0.053  1.00  0.00           C  
HETATM   28  O11 UNL     1      -5.319  -4.197  -0.168  1.00  0.00           O  
HETATM   29  C18 UNL     1      -1.026  -1.708  -0.569  1.00  0.00           C  
HETATM   30  O12 UNL     1      -0.033  -2.250  -1.271  1.00  0.00           O  
HETATM   31  O13 UNL     1      -0.965  -0.409  -0.485  1.00  0.00           O  
HETATM   32  C19 UNL     1      -0.621   0.834  -0.235  1.00  0.00           C  
HETATM   33  C20 UNL     1       0.787   0.955   0.310  1.00  0.00           C  
HETATM   34  O14 UNL     1       1.697   0.339  -0.551  1.00  0.00           O  
HETATM   35  C21 UNL     1       2.654  -0.594  -0.203  1.00  0.00           C  
HETATM   36  O15 UNL     1       2.723  -0.929   1.010  1.00  0.00           O  
HETATM   37  C22 UNL     1       3.606  -1.225  -1.169  1.00  0.00           C  
HETATM   38  C23 UNL     1       4.499  -0.069  -1.639  1.00  0.00           C  
HETATM   39  C24 UNL     1       5.395   0.039  -0.433  1.00  0.00           C  
HETATM   40  O16 UNL     1       5.833   1.057   0.110  1.00  0.00           O  
HETATM   41  C25 UNL     1       5.639  -1.361  -0.034  1.00  0.00           C  
HETATM   42  O17 UNL     1       6.642  -1.887   0.622  1.00  0.00           O  
HETATM   43  C26 UNL     1       6.731  -3.162   0.908  1.00  0.00           C  
HETATM   44  O18 UNL     1       7.690  -3.668   1.536  1.00  0.00           O  
HETATM   45  C27 UNL     1       5.707  -4.007   0.494  1.00  0.00           C  
HETATM   46  C28 UNL     1       5.753  -5.367   0.768  1.00  0.00           C  
HETATM   47  C29 UNL     1       4.754  -6.227   0.367  1.00  0.00           C  
HETATM   48  O19 UNL     1       4.840  -7.587   0.664  1.00  0.00           O  
HETATM   49  C30 UNL     1       3.688  -5.693  -0.325  1.00  0.00           C  
HETATM   50  O20 UNL     1       2.651  -6.474  -0.762  1.00  0.00           O  
HETATM   51  C31 UNL     1       3.650  -4.319  -0.597  1.00  0.00           C  
HETATM   52  O21 UNL     1       2.599  -3.758  -1.289  1.00  0.00           O  
HETATM   53  C32 UNL     1       4.650  -3.461  -0.195  1.00  0.00           C  
HETATM   54  C33 UNL     1       4.563  -2.106  -0.494  1.00  0.00           C  
HETATM   55  C34 UNL     1       1.080   2.446   0.399  1.00  0.00           C  
HETATM   56  O22 UNL     1       2.357   2.561   0.973  1.00  0.00           O  
HETATM   57  C35 UNL     1       0.179   6.992   1.251  1.00  0.00           C  
HETATM   58  C36 UNL     1       0.311   8.002   2.188  1.00  0.00           C  
HETATM   59  C37 UNL     1       0.261   9.333   1.760  1.00  0.00           C  
HETATM   60  O23 UNL     1       0.394  10.337   2.722  1.00  0.00           O  
HETATM   61  C38 UNL     1       0.086   9.693   0.448  1.00  0.00           C  
HETATM   62  O24 UNL     1       0.034  11.013   0.008  1.00  0.00           O  
HETATM   63  C39 UNL     1      -0.042   8.662  -0.461  1.00  0.00           C  
HETATM   64  O25 UNL     1      -0.222   8.982  -1.816  1.00  0.00           O  
HETATM   65  C40 UNL     1       0.005   7.354  -0.055  1.00  0.00           C  
HETATM   66  H1  UNL     1       0.393   3.189   2.329  1.00  0.00           H  
HETATM   67  H2  UNL     1      -2.509   1.617   0.228  1.00  0.00           H  
HETATM   68  H3  UNL     1      -0.894  -0.228   1.881  1.00  0.00           H  
HETATM   69  H4  UNL     1      -1.812   0.954   2.794  1.00  0.00           H  
HETATM   70  H5  UNL     1      -5.549   1.230  -0.773  1.00  0.00           H  
HETATM   71  H6  UNL     1      -6.995   1.581  -2.712  1.00  0.00           H  
HETATM   72  H7  UNL     1      -6.698  -2.001  -4.686  1.00  0.00           H  
HETATM   73  H8  UNL     1      -5.050  -3.879  -3.419  1.00  0.00           H  
HETATM   74  H9  UNL     1      -0.202  -3.907   0.697  1.00  0.00           H  
HETATM   75  H10 UNL     1      -1.567  -6.958   1.724  1.00  0.00           H  
HETATM   76  H11 UNL     1      -3.510  -7.042   1.384  1.00  0.00           H  
HETATM   77  H12 UNL     1      -5.798  -5.019   0.076  1.00  0.00           H  
HETATM   78  H13 UNL     1      -0.632   1.508  -1.147  1.00  0.00           H  
HETATM   79  H14 UNL     1       0.897   0.581   1.349  1.00  0.00           H  
HETATM   80  H15 UNL     1       3.127  -1.618  -2.056  1.00  0.00           H  
HETATM   81  H16 UNL     1       5.026  -0.405  -2.531  1.00  0.00           H  
HETATM   82  H17 UNL     1       3.894   0.829  -1.741  1.00  0.00           H  
HETATM   83  H18 UNL     1       6.621  -5.735   1.318  1.00  0.00           H  
HETATM   84  H19 UNL     1       4.166  -8.265   0.410  1.00  0.00           H  
HETATM   85  H20 UNL     1       2.618  -7.460  -0.601  1.00  0.00           H  
HETATM   86  H21 UNL     1       1.801  -4.256  -1.642  1.00  0.00           H  
HETATM   87  H22 UNL     1       1.120   2.862  -0.636  1.00  0.00           H  
HETATM   88  H23 UNL     1       2.445   1.914   1.721  1.00  0.00           H  
HETATM   89  H24 UNL     1       0.452   7.819   3.223  1.00  0.00           H  
HETATM   90  H25 UNL     1       0.376  11.315   2.556  1.00  0.00           H  
HETATM   91  H26 UNL     1       0.111  11.814   0.633  1.00  0.00           H  
HETATM   92  H27 UNL     1      -0.311   8.231  -2.462  1.00  0.00           H  
HETATM   93  H28 UNL     1      -0.104   6.601  -0.828  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   57
CONECT    3    4
CONECT    4    5   55   66
CONECT    5    6
CONECT    6    7   32   67
CONECT    7    8   68   69
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   19
CONECT   12   13   70
CONECT   13   14   15   15
CONECT   14   71
CONECT   15   16   17
CONECT   16   72
CONECT   17   18   19   19
CONECT   18   73
CONECT   19   20
CONECT   20   21   21   27
CONECT   21   22   29
CONECT   22   23   23   74
CONECT   23   24   25
CONECT   24   75
CONECT   25   26   27   27
CONECT   26   76
CONECT   27   28
CONECT   28   77
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   33   78
CONECT   33   34   55   79
CONECT   34   35
CONECT   35   36   36   37
CONECT   37   38   54   80
CONECT   38   39   81   82
CONECT   39   40   40   41
CONECT   41   42   54   54
CONECT   42   43
CONECT   43   44   44   45
CONECT   45   46   46   53
CONECT   46   47   83
CONECT   47   48   49   49
CONECT   48   84
CONECT   49   50   51
CONECT   50   85
CONECT   51   52   53   53
CONECT   52   86
CONECT   53   54
CONECT   55   56   87
CONECT   56   88
CONECT   57   58   58   65
CONECT   58   59   89
CONECT   59   60   61   61
CONECT   60   90
CONECT   61   62   63
CONECT   62   91
CONECT   63   64   65   65
CONECT   64   92
CONECT   65   93
END

HMDB0039268
     RDKit          3D
Heterophylliin E
 93100  0  0  0  0  0  0  0  0999 V2000
    0.4439    5.3099    2.8816 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327    5.5999    1.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    4.5398    0.7927 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119    3.1733    1.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1767    2.7259    1.2024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5062    1.5282    0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7899    0.4448    1.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9582   -0.2359    1.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1017   -0.0607    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0410    0.6843    1.4916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4784   -0.5983   -0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3403    0.2040   -1.1592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9452   -0.1749   -2.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7951    0.6554   -3.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6763   -1.4843   -2.8015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2457   -1.8833   -3.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8276   -2.3008   -2.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6242   -3.5610   -2.6051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2229   -1.8682   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2912   -2.8677   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098   -2.7792   -0.0960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -3.8880    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9332   -5.0500    0.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -6.0910    1.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717   -5.1263    0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9718   -6.2635    0.9669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9166   -4.0497    0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3186   -4.1966   -0.1677 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0257   -1.7081   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0327   -2.2502   -1.2707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646   -0.4090   -0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210    0.8344   -0.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7868    0.9548    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966    0.3392   -0.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6540   -0.5944   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7233   -0.9289    1.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -1.2249   -1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4994   -0.0695   -1.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3953    0.0390   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8329    1.0574    0.1101 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6395   -1.3611   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6418   -1.8871    0.6219 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7307   -3.1619    0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6901   -3.6677    1.5362 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7071   -4.0071    0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7533   -5.3670    0.7684 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7536   -6.2271    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8399   -7.5866    0.6635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6878   -5.6930   -0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6506   -6.4741   -0.7620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6502   -4.3189   -0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5990   -3.7578   -1.2895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505   -3.4608   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5634   -2.1062   -0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0803    2.4461    0.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3569    2.5612    0.9731 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1789    6.9918    1.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107    8.0021    2.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    9.3334    1.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   10.3374    2.7223 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    9.6927    0.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0344   11.0134    0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420    8.6615   -0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2223    8.9824   -1.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    7.3543   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    3.1887    2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    1.6171    0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938   -0.2279    1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122    0.9544    2.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5489    1.2305   -0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9952    1.5806   -2.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6977   -2.0010   -4.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0502   -3.8787   -3.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2023   -3.9073    0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -6.9584    1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -7.0420    1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7981   -5.0190    0.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6317    1.5080   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8967    0.5814    1.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1269   -1.6180   -2.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263   -0.4047   -2.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.8287   -1.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6212   -5.7348    1.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -8.2649    0.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6182   -7.4599   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006   -4.2559   -1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1197    2.8621   -0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4449    1.9143    1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    7.8192    3.2230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3758   11.3148    2.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114   11.8140    0.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
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  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  1  0
  8  9  1  0
  9 10  2  0
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 15 16  1  0
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 64 92  1  0
 65 93  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4,5,12,21,22,23-Heptahydroxy-8,18-dioxo-13-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylic acid	Generator

Chemical Formula

C₄₀H₂₈O₂₅

Average Molecular Weight

908.6353

Monoisotopic Molecular Weight

908.091966446

IUPAC Name

3,4,5,12,21,22,23-heptahydroxy-8,18-dioxo-13-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-11-yl 7,8,9-trihydroxy-3,5-dioxo-1H,2H,3H,5H-cyclopenta[c]isochromene-1-carboxylate

Traditional Name

CAS Registry Number

135309-00-1

SMILES

OC1C(OC(=O)C2=CC(O)=C(O)C(O)=C2)OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(O)C(O)=C(O)C=C3C(=O)OC2C1OC(=O)C1CC(=O)C2=C1C1=C(C=C(O)C(O)=C1O)C(=O)O2

InChI Identifier

InChI=1S/C40H28O25/c41-13-1-8(2-14(42)24(13)47)35(55)65-40-31(54)34(64-39(59)12-6-18(46)32-23(12)22-11(37(57)62-32)5-17(45)27(50)30(22)53)33-19(61-40)7-60-36(56)9-3-15(43)25(48)28(51)20(9)21-10(38(58)63-33)4-16(44)26(49)29(21)52/h1-5,12,19,31,33-34,40-45,47-54H,6-7H2

InChI Key

AQPVGKAQOQGNBT-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
Saccharolipid
Tetracarboxylic acid or derivatives
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Isocoumarin
2-benzopyran
Benzoate ester
Benzopyran
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
Aryl ketone
Aryl alkyl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Pyran
Oxane
Monocyclic benzene moiety
Monosaccharide
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Polyol
Carboxylic acid derivative
Acetal
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0039268)

Nuts (FooDB: FOOD00869)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.02 g/L	ALOGPS
logP	3.03	ALOGPS
logP	2.17	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	420.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	205.83 m³·mol⁻¹	ChemAxon
Polarizability	79.09 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	274.977	30932474
DeepCCS	[M-H]-	273.241	30932474
DeepCCS	[M-2H]-	307.274	30932474
DeepCCS	[M+Na]+	281.294	30932474
AllCCS	[M+H]+	265.5	32859911
AllCCS	[M+H-H2O]+	265.8	32859911
AllCCS	[M+NH4]+	265.2	32859911
AllCCS	[M+Na]+	265.1	32859911
AllCCS	[M-H]-	265.2	32859911
AllCCS	[M+Na-2H]-	268.6	32859911
AllCCS	[M+HCOO]-	272.5	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 - Heterophylliin E 10V, Positive-QTOF	splash10-0fk9-0910000111-3aa1e82eb6cc02626b2e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 20V, Positive-QTOF	splash10-0ufr-0910000120-e310688030d269d4278f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 40V, Positive-QTOF	splash10-0fi0-0940100020-755cbc65ec596e8fabec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 10V, Negative-QTOF	splash10-0ldi-0910000113-a32cd51999006663eb45	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 20V, Negative-QTOF	splash10-016r-0941000110-355f980f3b036308c863	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 40V, Negative-QTOF	splash10-002g-0494000010-67838c70378e98b415d3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 10V, Positive-QTOF	splash10-000i-0210000912-963ffe7d568d1a8ae22e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 20V, Positive-QTOF	splash10-004i-0390000211-71079cc7b90cfa361d09	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 40V, Positive-QTOF	splash10-0v00-5914411041-f5062cf8a23eddd4417e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 10V, Negative-QTOF	splash10-0a4i-0370000109-f833cd7bad520bb37554	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 20V, Negative-QTOF	splash10-0zi9-0913000263-42d71d62b31805ecc63f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin E 40V, Negative-QTOF	splash10-004j-1742000490-26bddf6133126fbc420f	2021-09-22	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

FDB018810

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14824938

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Heterophylliin E (HMDB0039268)

MOL for HMDB0039268 (Heterophylliin E)

3D MOL for HMDB0039268 (Heterophylliin E)

3D SDF for HMDB0039268 (Heterophylliin E)

3D-SDF for HMDB0039268 (Heterophylliin E)

PDB for HMDB0039268 (Heterophylliin E)

3D PDB for HMDB0039268 (Heterophylliin E)

SMILES for HMDB0039268 (Heterophylliin E)

INCHI for HMDB0039268 (Heterophylliin E)

Structure for HMDB0039268 (Heterophylliin E)

3D Structure for HMDB0039268 (Heterophylliin E)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra