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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:39:28 UTC

Update Date

2022-03-07 02:56:08 UTC

HMDB ID

HMDB0039264

Secondary Accession Numbers

HMDB39264

Metabolite Identification

Common Name

Heterophylliin A

Description

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

Structure

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


  Mrv0541 09121200392D          

 56 61  0  0  0  0            999 V2000
   -2.3662   -0.9331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -1.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6329   -2.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -2.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337   -1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -0.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6329   -0.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0326    0.5994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3653   -3.3993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6321   -2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323   -3.3993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660   -2.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660   -2.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323   -1.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6321   -2.1325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3653   -1.7329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3653   -0.8660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6321   -0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323   -0.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660   -0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1660    0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3653    0.8660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6321    0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    0.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323    1.7993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323   -4.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661   -1.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661   -0.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0990   -1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994   -2.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7661    0.4660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661   -0.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337   -0.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337    0.4660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997    1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0996    1.7329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651   -0.2668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3653   -1.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651   -1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -0.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -0.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -2.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1654   -2.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5651   -3.0655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326    2.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660    3.7988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4331    3.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329    2.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329    1.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7667    2.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9660    2.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674    3.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5671    4.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 28  1  0  0  0  0
  6  7  1  0  0  0  0
  6 35  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 21  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  2  0  0  0  0
 12 13  2  0  0  0  0
 12 27  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 24  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 34  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 44  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 53  1  0  0  0  0
 39 42  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 46  2  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 51  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 55  2  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END

HMDB0039264
     RDKit          3D
Heterophylliin A
 82 87  0  0  0  0  0  0  0  0999 V2000
    3.1249   -2.9940   -2.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046   -2.8785   -1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4913   -2.1145   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.4724    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177   -1.8957    1.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5264   -0.9740    1.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.6571    1.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.9048    0.6475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828   -2.4376    0.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333   -3.6874   -0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0142   -1.8791    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8062   -2.6087    1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1176   -2.3346    1.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8290   -3.1120    2.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7045   -1.2711    1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0609   -0.9679    1.3536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9922   -0.5262    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6913    0.5082   -0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6254   -0.8197   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0639    0.0841   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716    0.9386   -1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6862    1.7567   -2.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331    1.7384   -3.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0928    2.5730   -4.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095    0.8977   -3.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2605    0.8940   -4.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8064    0.0996   -2.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9295   -0.7566   -2.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    1.1688    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233    2.4006    0.4785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629    0.3984    0.7045 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0496   -0.1447    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    0.7871   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524    1.8862    0.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    3.1701    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809    3.3135   -0.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    4.3416    1.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372    4.2422    2.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5116    5.3959    3.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    5.3367    4.6157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469    6.6519    2.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4378    7.7503    3.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009    6.7572    1.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    7.9896    0.7297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254    5.5848    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4707    0.0181   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625    0.5075    0.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1939   -3.5413   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179   -3.4764   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3389   -4.1055   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2851   -4.0583    0.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6427   -4.8381   -1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8663   -5.4860   -1.4206 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7442   -4.9220   -2.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0301   -5.6546   -3.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -4.2772   -2.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -1.7279   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8831   -0.3155    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3707   -0.9189    2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -2.4862    2.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4028   -3.4964    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3751   -3.8853    3.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5474   -1.5462    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6310    0.7372   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.4694   -2.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6905    2.5062   -5.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0537    0.3586   -4.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4802   -0.7827   -3.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.8719   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    1.1581   -1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    3.2569    2.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8772    4.4290    5.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    8.6720    3.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647    8.8643    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293    5.7066   -0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9674    0.2127   -1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.1522    1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8987   -2.9080    0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1972   -3.5708    1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1223   -6.0254   -2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -5.7241   -4.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8251   -4.3547   -3.1246 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
 27 28  1  0
 21 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  2  0
 33 46  1  0
 46 47  1  0
  2 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  1  0
 50 52  2  0
 52 53  1  0
 52 54  1  0
 54 55  1  0
 54 56  2  0
 46  4  1  0
 56 48  1  0
 32  6  1  0
 45 37  1  0
 19 11  1  0
 27 20  1  0
  4 57  1  0
  6 58  1  0
  7 59  1  0
  7 60  1  0
 12 61  1  0
 14 62  1  0
 16 63  1  0
 18 64  1  0
 22 65  1  0
 24 66  1  0
 26 67  1  0
 28 68  1  0
 32 69  1  0
 33 70  1  0
 38 71  1  0
 40 72  1  0
 42 73  1  0
 44 74  1  0
 45 75  1  0
 46 76  1  0
 47 77  1  0
 49 78  1  0
 51 79  1  0
 53 80  1  0
 55 81  1  0
 56 82  1  0
M  END


  Mrv0541 09121200392D          

 56 61  0  0  0  0            999 V2000
   -2.3662   -0.9331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325   -1.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6329   -2.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8337   -2.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337   -1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0039264

> <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)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)55-29-27(47)34(56-31(49)9-3-14(37)22(42)15(38)4-9)53-18-7-52-32(50)10-5-16(39)23(43)25(45)19(10)20-11(33(51)54-28(18)29)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-47H,7H2

> <INCHI_KEY>
NLDMNSXOCDLTTB-UHFFFAOYSA-N

> <FORMULA>
C34H26O22

> <MOLECULAR_WEIGHT>
786.557

> <EXACT_MASS>
786.091572516

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
69.51102292201519

> <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-11-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-13-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.679855862666666

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.799629718361862

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.340445346425418

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0536715944347295

> <JCHEM_POLAR_SURFACE_AREA>
377.4200000000001

> <JCHEM_REFRACTIVITY>
178.0604

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.87e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039264
     RDKit          3D
Heterophylliin A
 82 87  0  0  0  0  0  0  0  0999 V2000
    3.1249   -2.9940   -2.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4913   -2.1145   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.4724    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177   -1.8957    1.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5264   -0.9740    1.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.6571    1.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.9048    0.6475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828   -2.4376    0.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333   -3.6874   -0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0142   -1.8791    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8062   -2.6087    1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1176   -2.3346    1.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6862    1.7567   -2.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2524    1.8862    0.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    3.1701    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809    3.3135   -0.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    4.3416    1.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1009    6.7572    1.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    7.9896    0.7297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254    5.5848    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4707    0.0181   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625    0.5075    0.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1939   -3.5413   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179   -3.4764   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3389   -4.1055   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8663   -5.4860   -1.4206 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8772    4.4290    5.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    8.6720    3.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8251   -4.3547   -3.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  6  1  0
  6  7  1  0
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  9 10  2  0
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 43 45  2  0
 33 46  1  0
 46 47  1  0
  2 48  1  0
 48 49  2  0
 49 50  1  0
 50 51  1  0
 50 52  2  0
 52 53  1  0
 52 54  1  0
 54 55  1  0
 54 56  2  0
 46  4  1  0
 56 48  1  0
 32  6  1  0
 45 37  1  0
 19 11  1  0
 27 20  1  0
  4 57  1  0
  6 58  1  0
  7 59  1  0
  7 60  1  0
 12 61  1  0
 14 62  1  0
 16 63  1  0
 18 64  1  0
 22 65  1  0
 24 66  1  0
 26 67  1  0
 28 68  1  0
 32 69  1  0
 33 70  1  0
 38 71  1  0
 40 72  1  0
 42 73  1  0
 44 74  1  0
 45 75  1  0
 46 76  1  0
 47 77  1  0
 49 78  1  0
 51 79  1  0
 53 80  1  0
 55 81  1  0
 56 82  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      -4.417  -1.742   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.541  -3.235   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.048  -4.478   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.556  -4.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.810  -3.109   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.556  -1.866   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.048  -1.866   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.292  -0.623   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.794   1.119   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0     -10.015  -6.345   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -8.647  -5.474   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.154  -6.345   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.910  -5.474   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.910  -3.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.154  -3.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.647  -3.981   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.015  -3.235   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0     -10.015  -1.617   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -8.647  -0.623   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.154  -1.617   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.910  -0.623   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.910   0.870   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -10.015   1.617   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -8.647   0.870   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.154   1.617   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -7.154   3.359   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.154  -7.962   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.683  -3.109   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.430  -1.866   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.923  -1.866   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.918  -3.109   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.172  -4.478   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.430   0.870   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.683  -0.498   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.810  -0.498   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.556   0.870   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.426   2.861   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.919   3.235   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       8.521  -0.498   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      10.015  -3.109   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       8.521  -3.109   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.775  -1.866   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.283  -1.866   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.536  -3.109   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.283  -4.478   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       7.775  -4.478   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       8.521  -5.722   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       2.674   4.229   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       1.803   7.091   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       0.808   6.096   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       1.181   4.602   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.061   3.484   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -1.431   3.857   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -1.803   5.349   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -0.686   6.469   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -1.059   7.962   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11   10   12   16                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14    2   13   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   11   15   17                                                  
CONECT   17   16                                                            
CONECT   18   19                                                            
CONECT   19   18   20   24                                                  
CONECT   20   15   19   21                                                  
CONECT   21    8   20   22                                                  
CONECT   22   21   25                                                       
CONECT   23   24                                                            
CONECT   24   19   23   25                                                  
CONECT   25   22   24   26                                                  
CONECT   26   25                                                            
CONECT   27   12                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   44                                                  
CONECT   32   31                                                            
CONECT   33   34                                                            
CONECT   34   29   33   35                                                  
CONECT   35    6   34   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   53                                                  
CONECT   38   37                                                            
CONECT   39   42                                                            
CONECT   40   41                                                            
CONECT   41   40   42   46                                                  
CONECT   42   39   41   43                                                  
CONECT   43   42   44                                                       
CONECT   44   31   43   45                                                  
CONECT   45   44   46                                                       
CONECT   46   41   45   47                                                  
CONECT   47   46                                                            
CONECT   48   51                                                            
CONECT   49   50                                                            
CONECT   50   49   51   55                                                  
CONECT   51   48   50   52                                                  
CONECT   52   51   53                                                       
CONECT   53   37   52   54                                                  
CONECT   54   53   55                                                       
CONECT   55   50   54   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  122    0
END

COMPND    HMDB0039264
HETATM    1  O1  UNL     1       3.125  -2.994  -2.092  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.905  -2.879  -1.125  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.491  -2.115  -0.039  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.230  -1.472   0.008  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.418  -1.896   1.013  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.526  -0.974   1.469  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.799  -1.657   1.872  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.446  -1.905   0.648  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.683  -2.438   0.389  1.00  0.00           C  
HETATM   10  O5  UNL     1      -2.633  -3.687  -0.069  1.00  0.00           O  
HETATM   11  C6  UNL     1      -4.014  -1.879   0.532  1.00  0.00           C  
HETATM   12  C7  UNL     1      -4.806  -2.609   1.442  1.00  0.00           C  
HETATM   13  C8  UNL     1      -6.118  -2.335   1.727  1.00  0.00           C  
HETATM   14  O6  UNL     1      -6.829  -3.112   2.648  1.00  0.00           O  
HETATM   15  C9  UNL     1      -6.704  -1.271   1.075  1.00  0.00           C  
HETATM   16  O7  UNL     1      -8.061  -0.968   1.354  1.00  0.00           O  
HETATM   17  C10 UNL     1      -5.992  -0.526   0.181  1.00  0.00           C  
HETATM   18  O8  UNL     1      -6.691   0.508  -0.408  1.00  0.00           O  
HETATM   19  C11 UNL     1      -4.625  -0.820  -0.107  1.00  0.00           C  
HETATM   20  C12 UNL     1      -4.064   0.084  -1.128  1.00  0.00           C  
HETATM   21  C13 UNL     1      -2.972   0.939  -1.062  1.00  0.00           C  
HETATM   22  C14 UNL     1      -2.686   1.757  -2.195  1.00  0.00           C  
HETATM   23  C15 UNL     1      -3.433   1.738  -3.340  1.00  0.00           C  
HETATM   24  O9  UNL     1      -3.093   2.573  -4.425  1.00  0.00           O  
HETATM   25  C16 UNL     1      -4.509   0.898  -3.409  1.00  0.00           C  
HETATM   26  O10 UNL     1      -5.261   0.894  -4.589  1.00  0.00           O  
HETATM   27  C17 UNL     1      -4.806   0.100  -2.329  1.00  0.00           C  
HETATM   28  O11 UNL     1      -5.930  -0.757  -2.437  1.00  0.00           O  
HETATM   29  C18 UNL     1      -2.067   1.169   0.031  1.00  0.00           C  
HETATM   30  O12 UNL     1      -2.123   2.401   0.478  1.00  0.00           O  
HETATM   31  O13 UNL     1      -1.163   0.398   0.704  1.00  0.00           O  
HETATM   32  C19 UNL     1       0.050  -0.145   0.262  1.00  0.00           C  
HETATM   33  C20 UNL     1       1.158   0.787  -0.055  1.00  0.00           C  
HETATM   34  O14 UNL     1       1.252   1.886   0.821  1.00  0.00           O  
HETATM   35  C21 UNL     1       1.099   3.170   0.290  1.00  0.00           C  
HETATM   36  O15 UNL     1       0.881   3.314  -0.925  1.00  0.00           O  
HETATM   37  C22 UNL     1       1.190   4.342   1.142  1.00  0.00           C  
HETATM   38  C23 UNL     1       1.437   4.242   2.502  1.00  0.00           C  
HETATM   39  C24 UNL     1       1.512   5.396   3.253  1.00  0.00           C  
HETATM   40  O16 UNL     1       1.758   5.337   4.616  1.00  0.00           O  
HETATM   41  C25 UNL     1       1.347   6.652   2.689  1.00  0.00           C  
HETATM   42  O17 UNL     1       1.438   7.750   3.518  1.00  0.00           O  
HETATM   43  C26 UNL     1       1.101   6.757   1.336  1.00  0.00           C  
HETATM   44  O18 UNL     1       0.930   7.990   0.730  1.00  0.00           O  
HETATM   45  C27 UNL     1       1.025   5.585   0.573  1.00  0.00           C  
HETATM   46  C28 UNL     1       2.471   0.018  -0.062  1.00  0.00           C  
HETATM   47  O19 UNL     1       3.262   0.508   0.945  1.00  0.00           O  
HETATM   48  C29 UNL     1       5.194  -3.541  -1.176  1.00  0.00           C  
HETATM   49  C30 UNL     1       6.118  -3.476  -0.155  1.00  0.00           C  
HETATM   50  C31 UNL     1       7.339  -4.106  -0.204  1.00  0.00           C  
HETATM   51  O20 UNL     1       8.285  -4.058   0.801  1.00  0.00           O  
HETATM   52  C32 UNL     1       7.643  -4.838  -1.339  1.00  0.00           C  
HETATM   53  O21 UNL     1       8.866  -5.486  -1.421  1.00  0.00           O  
HETATM   54  C33 UNL     1       6.744  -4.922  -2.372  1.00  0.00           C  
HETATM   55  O22 UNL     1       7.030  -5.655  -3.527  1.00  0.00           O  
HETATM   56  C34 UNL     1       5.525  -4.277  -2.293  1.00  0.00           C  
HETATM   57  H1  UNL     1       1.717  -1.728  -0.967  1.00  0.00           H  
HETATM   58  H2  UNL     1       0.883  -0.316   2.277  1.00  0.00           H  
HETATM   59  H3  UNL     1      -1.371  -0.919   2.480  1.00  0.00           H  
HETATM   60  H4  UNL     1      -0.482  -2.486   2.479  1.00  0.00           H  
HETATM   61  H5  UNL     1      -4.403  -3.496   1.968  1.00  0.00           H  
HETATM   62  H6  UNL     1      -6.375  -3.885   3.113  1.00  0.00           H  
HETATM   63  H7  UNL     1      -8.547  -1.546   2.020  1.00  0.00           H  
HETATM   64  H8  UNL     1      -7.631   0.737  -0.245  1.00  0.00           H  
HETATM   65  H9  UNL     1      -1.866   2.469  -2.197  1.00  0.00           H  
HETATM   66  H10 UNL     1      -3.691   2.506  -5.236  1.00  0.00           H  
HETATM   67  H11 UNL     1      -6.054   0.359  -4.800  1.00  0.00           H  
HETATM   68  H12 UNL     1      -6.480  -0.783  -3.250  1.00  0.00           H  
HETATM   69  H13 UNL     1      -0.135  -0.872  -0.542  1.00  0.00           H  
HETATM   70  H14 UNL     1       0.969   1.158  -1.104  1.00  0.00           H  
HETATM   71  H15 UNL     1       1.562   3.257   2.921  1.00  0.00           H  
HETATM   72  H16 UNL     1       1.877   4.429   5.035  1.00  0.00           H  
HETATM   73  H17 UNL     1       1.321   8.672   3.134  1.00  0.00           H  
HETATM   74  H18 UNL     1       0.965   8.864   1.177  1.00  0.00           H  
HETATM   75  H19 UNL     1       0.829   5.707  -0.499  1.00  0.00           H  
HETATM   76  H20 UNL     1       2.967   0.213  -1.029  1.00  0.00           H  
HETATM   77  H21 UNL     1       3.686  -0.152   1.522  1.00  0.00           H  
HETATM   78  H22 UNL     1       5.899  -2.908   0.744  1.00  0.00           H  
HETATM   79  H23 UNL     1       8.197  -3.571   1.671  1.00  0.00           H  
HETATM   80  H24 UNL     1       9.122  -6.025  -2.228  1.00  0.00           H  
HETATM   81  H25 UNL     1       6.376  -5.724  -4.291  1.00  0.00           H  
HETATM   82  H26 UNL     1       4.825  -4.355  -3.125  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   48
CONECT    3    4
CONECT    4    5   46   57
CONECT    5    6
CONECT    6    7   32   58
CONECT    7    8   59   60
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   19
CONECT   12   13   61
CONECT   13   14   15   15
CONECT   14   62
CONECT   15   16   17
CONECT   16   63
CONECT   17   18   19   19
CONECT   18   64
CONECT   19   20
CONECT   20   21   21   27
CONECT   21   22   29
CONECT   22   23   23   65
CONECT   23   24   25
CONECT   24   66
CONECT   25   26   27   27
CONECT   26   67
CONECT   27   28
CONECT   28   68
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   33   69
CONECT   33   34   46   70
CONECT   34   35
CONECT   35   36   36   37
CONECT   37   38   38   45
CONECT   38   39   71
CONECT   39   40   41   41
CONECT   40   72
CONECT   41   42   43
CONECT   42   73
CONECT   43   44   45   45
CONECT   44   74
CONECT   45   75
CONECT   46   47   76
CONECT   47   77
CONECT   48   49   49   56
CONECT   49   50   78
CONECT   50   51   52   52
CONECT   51   79
CONECT   52   53   54
CONECT   53   80
CONECT   54   55   56   56
CONECT   55   81
CONECT   56   82
END

HMDB0039264
     RDKit          3D
Heterophylliin A
 82 87  0  0  0  0  0  0  0  0999 V2000
    3.1249   -2.9940   -2.0924 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046   -2.8785   -1.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4913   -2.1145   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.4724    0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177   -1.8957    1.0135 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5264   -0.9740    1.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7992   -1.6571    1.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462   -1.9048    0.6475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828   -2.4376    0.3895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333   -3.6874   -0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0142   -1.8791    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8062   -2.6087    1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1176   -2.3346    1.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8290   -3.1120    2.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7045   -1.2711    1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0609   -0.9679    1.3536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9922   -0.5262    0.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6913    0.5082   -0.4082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6254   -0.8197   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0639    0.0841   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716    0.9386   -1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6862    1.7567   -2.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4331    1.7384   -3.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0928    2.5730   -4.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5095    0.8977   -3.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2605    0.8940   -4.5888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8064    0.0996   -2.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9295   -0.7566   -2.4370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667    1.1688    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233    2.4006    0.4785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629    0.3984    0.7045 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0496   -0.1447    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    0.7871   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2524    1.8862    0.8206 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986    3.1701    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8809    3.3135   -0.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    4.3416    1.1418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372    4.2422    2.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5116    5.3959    3.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    5.3367    4.6157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469    6.6519    2.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4378    7.7503    3.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009    6.7572    1.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296    7.9896    0.7297 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254    5.5848    0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4707    0.0181   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625    0.5075    0.9446 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1939   -3.5413   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1179   -3.4764   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3389   -4.1055   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2851   -4.0583    0.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6427   -4.8381   -1.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8663   -5.4860   -1.4206 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7442   -4.9220   -2.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0301   -5.6546   -3.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5249   -4.2772   -2.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -1.7279   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8831   -0.3155    2.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3707   -0.9189    2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -2.4862    2.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4028   -3.4964    1.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3751   -3.8853    3.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5474   -1.5462    2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6310    0.7372   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.4694   -2.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6905    2.5062   -5.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0537    0.3586   -4.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4802   -0.7827   -3.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352   -0.8719   -0.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689    1.1581   -1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622    3.2569    2.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8772    4.4290    5.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    8.6720    3.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647    8.8643    1.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8293    5.7066   -0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9674    0.2127   -1.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.1522    1.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8987   -2.9080    0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1972   -3.5708    1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1223   -6.0254   -2.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3757   -5.7241   -4.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8251   -4.3547   -3.1246 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
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3-Di-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-a-D-glucopyranose	HMDB
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 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₃₄H₂₆O₂₂

Average Molecular Weight

786.557

Monoisotopic Molecular Weight

786.091572516

IUPAC Name

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

Traditional Name

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

CAS Registry Number

87687-52-3

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)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(48)55-29-27(47)34(56-31(49)9-3-14(37)22(42)15(38)4-9)53-18-7-52-32(50)10-5-16(39)23(43)25(45)19(10)20-11(33(51)54-28(18)29)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-47H,7H2

InChI Key

NLDMNSXOCDLTTB-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0039264)

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	1.87 g/L	ALOGPS
logP	2.67	ALOGPS
logP	2.68	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.34	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	377.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	178.06 m³·mol⁻¹	ChemAxon
Polarizability	69.51 Å³	ChemAxon
Number of Rings	6	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]+	259.806	30932474
DeepCCS	[M-H]-	258.016	30932474
DeepCCS	[M-2H]-	292.049	30932474
DeepCCS	[M+Na]+	265.985	30932474
AllCCS	[M+H]+	253.6	32859911
AllCCS	[M+H-H2O]+	253.4	32859911
AllCCS	[M+NH4]+	253.8	32859911
AllCCS	[M+Na]+	253.9	32859911
AllCCS	[M-H]-	253.9	32859911
AllCCS	[M+Na-2H]-	256.6	32859911
AllCCS	[M+HCOO]-	259.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heterophylliin A	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)C1=CC(O)=C(O)C(O)=C1	8970.3	Standard polar	33892256
Heterophylliin A	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)C1=CC(O)=C(O)C(O)=C1	6020.0	Standard non polar	33892256
Heterophylliin A	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)C1=CC(O)=C(O)C(O)=C1	7326.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0903074000-4f711d18e968c3f1e630	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heterophylliin A GC-MS (TMS_1_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 10V, Positive-QTOF	splash10-0g4i-0900001300-052fea7a18e0053f2018	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 20V, Positive-QTOF	splash10-0udi-0900000100-d733329fa7c3c5f4a29a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 40V, Positive-QTOF	splash10-0ufr-0900100100-391c88a7f1cff5ff30e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 10V, Negative-QTOF	splash10-014r-0900001400-c865c1f847b730d79528	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 20V, Negative-QTOF	splash10-014i-0921001100-8bf8e9d4f7fd396de3ed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 40V, Negative-QTOF	splash10-014i-0903000000-8c2b0515add3f7f0a8c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 10V, Negative-QTOF	splash10-000i-0300001900-f192731bc54b72fc9578	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 20V, Negative-QTOF	splash10-0gdi-0900003700-f71706ba0cfc0ccf0c3e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 40V, Negative-QTOF	splash10-00or-3900001200-5157baa34313794cb378	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 10V, Positive-QTOF	splash10-014r-0900007200-0ad5c93e540729ce10c7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 20V, Positive-QTOF	splash10-0udr-1900104300-03ba33a25b96eded9ad7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heterophylliin A 40V, Positive-QTOF	splash10-0ufr-4902001400-c593c0fe1cf784e61f74	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

FDB018805

KNApSAcK ID

Not Available

Chemspider ID

413780

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

471120

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 A (HMDB0039264)

MOL for HMDB0039264 (Heterophylliin A)

3D MOL for HMDB0039264 (Heterophylliin A)

3D SDF for HMDB0039264 (Heterophylliin A)

3D-SDF for HMDB0039264 (Heterophylliin A)

PDB for HMDB0039264 (Heterophylliin A)

3D PDB for HMDB0039264 (Heterophylliin A)

SMILES for HMDB0039264 (Heterophylliin A)

INCHI for HMDB0039264 (Heterophylliin A)

Structure for HMDB0039264 (Heterophylliin A)

3D Structure for HMDB0039264 (Heterophylliin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra