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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:25 UTC

Update Date

2022-03-07 02:52:39 UTC

HMDB ID

HMDB0030685

Secondary Accession Numbers

HMDB30685

Metabolite Identification

Common Name

Cycloheterophyllin

Description

Cycloheterophyllin belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. Thus, cycloheterophyllin is considered to be a flavonoid. Cycloheterophyllin has been detected, but not quantified in, fruits and jackfruits (Artocarpus heterophyllus). This could make cycloheterophyllin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cycloheterophyllin.

Structure

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


  Mrv0541 05061305262D          

 37 41  0  0  0  0            999 V2000
    1.5434    4.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    4.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    2.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4054    3.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5342    3.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9398    2.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -0.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8345    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    4.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1287    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379    2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271    2.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400   -0.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416    0.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5342    0.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471    0.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563    1.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3177    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253    3.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0142    2.1076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7324   -0.2949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3453   -0.6381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0326    0.0483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    1.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250    2.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 10  9  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  2  0  0  0  0
 20 19  1  0  0  0  0
 21 13  1  0  0  0  0
 21 18  2  0  0  0  0
 22 11  1  0  0  0  0
 23 22  1  0  0  0  0
 25 16  2  0  0  0  0
 25 24  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 16  1  0  0  0  0
 27 17  2  0  0  0  0
 28 17  1  0  0  0  0
 28 24  2  0  0  0  0
 29 18  1  0  0  0  0
 29 23  2  0  0  0  0
 30  5  1  0  0  0  0
 30  6  1  0  0  0  0
 30 10  1  0  0  0  0
 31 19  1  0  0  0  0
 32 20  1  0  0  0  0
 33 25  1  0  0  0  0
 34 26  2  0  0  0  0
 35 21  1  0  0  0  0
 35 22  1  0  0  0  0
 36 28  1  0  0  0  0
 36 29  1  0  0  0  0
 37 27  1  0  0  0  0
 37 30  1  0  0  0  0
M  END

HMDB0030685
     RDKit          3D
Cycloheterophyllin
 67 71  0  0  0  0  0  0  0  0999 V2000
   -3.8548    3.6614    0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039    2.3583    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431    1.6345    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227    1.9846   -0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    0.8270   -1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -0.1886   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590   -1.1200   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9566   -2.1106    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -2.1740    0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -3.1211    1.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161   -1.2675    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848   -1.3336    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0763   -2.2278    1.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -0.3936   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7968    0.5791   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    0.5886   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901   -0.2804   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6010    1.5598   -1.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569    2.5280   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073    3.4192   -3.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3630    4.3898   -3.9702 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781    3.3470   -3.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947    4.2526   -3.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8212    2.3693   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674    1.4778   -1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    0.5034   -0.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7973   -0.4774   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181   -0.5286    1.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9416   -1.5173    1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3976   -2.6720    1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3213   -1.4785    3.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593   -3.0641    1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1611   -2.9361    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547   -1.8980    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5120   -2.6056   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7013   -1.0724    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8327   -1.0435   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8244    3.3900    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0438    4.2160   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122    4.2008    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923    0.8540    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6449    1.2127    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541    2.3320    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3731    2.7185   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381    0.3141   -2.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    1.1952   -2.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -3.8162    2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965    2.6144   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966    4.5242   -4.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7686    4.9862   -4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8996    2.3204   -2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.4614   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    0.2741    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663   -3.1654    0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8847   -3.4056    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105   -2.3335    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4108   -1.4952    3.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595   -2.3512    3.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933   -0.5656    3.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -3.8340    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8351   -3.6276    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -3.1921   -1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2175   -3.3039   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9708   -1.8341   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1247   -0.7931    2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5583   -1.7480    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9887   -0.1953    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
  8 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
 17  6  1  0
 25 18  1  0
 37  7  1  0
 17 11  2  0
 27 14  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
 10 47  1  0
 19 48  1  0
 21 49  1  0
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 30 54  1  0
 30 55  1  0
 30 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 35 62  1  0
 35 63  1  0
 35 64  1  0
 36 65  1  0
 36 66  1  0
 36 67  1  0
M  END


  Mrv0541 05061305262D          

 37 41  0  0  0  0            999 V2000
    1.5434    4.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    4.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407    2.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4054    3.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5342    3.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9398    2.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9213    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5158    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -0.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8345    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3361    4.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1287    1.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379    2.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6363    1.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6271    2.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308    0.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400   -0.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3545    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416    0.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5342    0.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1471    0.1627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    1.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    1.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1563    1.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3177    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253    3.2517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0142    2.1076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7324   -0.2949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3453   -0.6381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0326    0.0483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    1.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250    2.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 10  9  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  7  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  2  0  0  0  0
 20 19  1  0  0  0  0
 21 13  1  0  0  0  0
 21 18  2  0  0  0  0
 22 11  1  0  0  0  0
 23 22  1  0  0  0  0
 25 16  2  0  0  0  0
 25 24  1  0  0  0  0
 26 23  1  0  0  0  0
 26 24  1  0  0  0  0
 27 16  1  0  0  0  0
 27 17  2  0  0  0  0
 28 17  1  0  0  0  0
 28 24  2  0  0  0  0
 29 18  1  0  0  0  0
 29 23  2  0  0  0  0
 30  5  1  0  0  0  0
 30  6  1  0  0  0  0
 30 10  1  0  0  0  0
 31 19  1  0  0  0  0
 32 20  1  0  0  0  0
 33 25  1  0  0  0  0
 34 26  2  0  0  0  0
 35 21  1  0  0  0  0
 35 22  1  0  0  0  0
 36 28  1  0  0  0  0
 36 29  1  0  0  0  0
 37 27  1  0  0  0  0
 37 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030685

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H30O7/c1-14(2)7-8-17-27-16(9-10-30(5,6)37-27)25(33)24-26(34)23-22(11-15(3)4)35-21-13-20(32)19(31)12-18(21)29(23)36-28(17)24/h7,9-13,22,31-33H,8H2,1-6H3

> <INCHI_KEY>
ZZPIXEJZTXAVCX-UHFFFAOYSA-N

> <FORMULA>
C30H30O7

> <MOLECULAR_WEIGHT>
502.555

> <EXACT_MASS>
502.199153314

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
55.475746013568425

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7,15-trihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-13-one

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
6.232577830333334

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.902958907052914

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.226891882982681

> <JCHEM_PKA_STRONGEST_BASIC>
-4.572761241534584

> <JCHEM_POLAR_SURFACE_AREA>
105.45

> <JCHEM_REFRACTIVITY>
144.6722

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cycloheterophyllin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030685
     RDKit          3D
Cycloheterophyllin
 67 71  0  0  0  0  0  0  0  0999 V2000
   -3.8548    3.6614    0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039    2.3583    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431    1.6345    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227    1.9846   -0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    0.8270   -1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -0.1886   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590   -1.1200   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9566   -2.1106    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -2.1740    0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -3.1211    1.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161   -1.2675    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848   -1.3336    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0763   -2.2278    1.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -0.3936   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7968    0.5791   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    0.5886   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901   -0.2804   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6010    1.5598   -1.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569    2.5280   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073    3.4192   -3.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3630    4.3898   -3.9702 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781    3.3470   -3.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947    4.2526   -3.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8212    2.3693   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674    1.4778   -1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    0.5034   -0.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7973   -0.4774   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181   -0.5286    1.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9416   -1.5173    1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3976   -2.6720    1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3213   -1.4785    3.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593   -3.0641    1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1611   -2.9361    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547   -1.8980    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5120   -2.6056   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7013   -1.0724    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8327   -1.0435   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8244    3.3900    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0438    4.2160   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122    4.2008    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923    0.8540    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6449    1.2127    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541    2.3320    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3731    2.7185   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381    0.3141   -2.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    1.1952   -2.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -3.8162    2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965    2.6144   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966    4.5242   -4.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7686    4.9862   -4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8996    2.3204   -2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.4614   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    0.2741    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663   -3.1654    0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8847   -3.4056    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105   -2.3335    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4108   -1.4952    3.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595   -2.3512    3.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933   -0.5656    3.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -3.8340    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8351   -3.6276    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -3.1921   -1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2175   -3.3039   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9708   -1.8341   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1247   -0.7931    2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5583   -1.7480    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9887   -0.1953    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
  8 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
 17  6  1  0
 25 18  1  0
 37  7  1  0
 17 11  2  0
 27 14  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
 10 47  1  0
 19 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 35 62  1  0
 35 63  1  0
 35 64  1  0
 36 65  1  0
 36 66  1  0
 36 67  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.881   8.419   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.470   9.060   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.818  -4.395   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -2.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.596   4.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.223   5.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.731   6.497   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.621   5.429   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.320   1.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.429   2.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.078  -1.832   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.558   4.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.777   2.012   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.361   7.992   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.188  -2.900   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.840   2.012   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.991   3.934   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.188   2.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.037   4.575   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.147   3.507   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.297   1.585   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.448  -0.337   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.662   0.731   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.251   1.371   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.731   0.944   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.141   0.304   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.470   3.507   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.881   2.866   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.292   2.226   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.060   4.148   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.407   6.070   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -5.627   3.934   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.100  -0.550   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.511  -1.191   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.928   0.090   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.401   3.294   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.580   4.575   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5   30                                                            
CONECT    6   30                                                            
CONECT    7    8   14                                                       
CONECT    8    7   17                                                       
CONECT    9   10   16                                                       
CONECT   10    9   30                                                       
CONECT   11   15   22                                                       
CONECT   12   18   19                                                       
CONECT   13   20   21                                                       
CONECT   14    1    2    7                                                  
CONECT   15    3    4   11                                                  
CONECT   16    9   25   27                                                  
CONECT   17    8   27   28                                                  
CONECT   18   12   21   29                                                  
CONECT   19   12   20   31                                                  
CONECT   20   13   19   32                                                  
CONECT   21   13   18   35                                                  
CONECT   22   11   23   35                                                  
CONECT   23   22   26   29                                                  
CONECT   24   25   26   28                                                  
CONECT   25   16   24   33                                                  
CONECT   26   23   24   34                                                  
CONECT   27   16   17   37                                                  
CONECT   28   17   24   36                                                  
CONECT   29   18   23   36                                                  
CONECT   30    5    6   10   37                                             
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   25                                                            
CONECT   34   26                                                            
CONECT   35   21   22                                                       
CONECT   36   28   29                                                       
CONECT   37   27   30                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

COMPND    HMDB0030685
HETATM    1  C1  UNL     1      -3.855   3.661   0.558  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.104   2.358   0.247  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.643   1.635   1.435  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.923   1.985  -0.976  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.266   0.827  -1.581  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.677  -0.189  -0.704  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.459  -1.120  -0.036  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.957  -2.111   0.775  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.600  -2.174   0.927  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.011  -3.121   1.712  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.216  -1.268   0.282  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.585  -1.334   0.437  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.076  -2.228   1.172  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.349  -0.394  -0.238  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.797   0.579  -1.039  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.469   0.589  -1.147  1.00  0.00           O  
HETATM   17  C14 UNL     1      -0.290  -0.280  -0.527  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.601   1.560  -1.743  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.057   2.528  -2.540  1.00  0.00           C  
HETATM   20  C17 UNL     1       2.907   3.419  -3.171  1.00  0.00           C  
HETATM   21  O4  UNL     1       2.363   4.390  -3.970  1.00  0.00           O  
HETATM   22  C18 UNL     1       4.278   3.347  -3.011  1.00  0.00           C  
HETATM   23  O5  UNL     1       5.095   4.253  -3.656  1.00  0.00           O  
HETATM   24  C19 UNL     1       4.821   2.369  -2.206  1.00  0.00           C  
HETATM   25  C20 UNL     1       3.967   1.478  -1.575  1.00  0.00           C  
HETATM   26  O6  UNL     1       4.485   0.503  -0.775  1.00  0.00           O  
HETATM   27  C21 UNL     1       3.797  -0.477  -0.064  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.218  -0.529   1.351  1.00  0.00           C  
HETATM   29  C23 UNL     1       4.942  -1.517   1.851  1.00  0.00           C  
HETATM   30  C24 UNL     1       5.398  -2.672   1.026  1.00  0.00           C  
HETATM   31  C25 UNL     1       5.321  -1.479   3.308  1.00  0.00           C  
HETATM   32  C26 UNL     1      -2.859  -3.064   1.449  1.00  0.00           C  
HETATM   33  C27 UNL     1      -4.161  -2.936   1.249  1.00  0.00           C  
HETATM   34  C28 UNL     1      -4.755  -1.898   0.394  1.00  0.00           C  
HETATM   35  C29 UNL     1      -5.512  -2.606  -0.718  1.00  0.00           C  
HETATM   36  C30 UNL     1      -5.701  -1.072   1.246  1.00  0.00           C  
HETATM   37  O7  UNL     1      -3.833  -1.044  -0.199  1.00  0.00           O  
HETATM   38  H1  UNL     1      -4.824   3.390   1.023  1.00  0.00           H  
HETATM   39  H2  UNL     1      -4.044   4.216  -0.367  1.00  0.00           H  
HETATM   40  H3  UNL     1      -3.212   4.201   1.285  1.00  0.00           H  
HETATM   41  H4  UNL     1      -3.392   0.854   1.759  1.00  0.00           H  
HETATM   42  H5  UNL     1      -1.645   1.213   1.406  1.00  0.00           H  
HETATM   43  H6  UNL     1      -2.654   2.332   2.347  1.00  0.00           H  
HETATM   44  H7  UNL     1      -3.373   2.718  -1.734  1.00  0.00           H  
HETATM   45  H8  UNL     1      -3.038   0.314  -2.248  1.00  0.00           H  
HETATM   46  H9  UNL     1      -1.515   1.195  -2.338  1.00  0.00           H  
HETATM   47  H10 UNL     1      -0.496  -3.816   2.215  1.00  0.00           H  
HETATM   48  H11 UNL     1       0.997   2.614  -2.688  1.00  0.00           H  
HETATM   49  H12 UNL     1       1.397   4.524  -4.148  1.00  0.00           H  
HETATM   50  H13 UNL     1       4.769   4.986  -4.252  1.00  0.00           H  
HETATM   51  H14 UNL     1       5.900   2.320  -2.085  1.00  0.00           H  
HETATM   52  H15 UNL     1       4.116  -1.461  -0.522  1.00  0.00           H  
HETATM   53  H16 UNL     1       3.924   0.274   2.008  1.00  0.00           H  
HETATM   54  H17 UNL     1       4.566  -3.165   0.487  1.00  0.00           H  
HETATM   55  H18 UNL     1       5.885  -3.406   1.697  1.00  0.00           H  
HETATM   56  H19 UNL     1       6.211  -2.333   0.324  1.00  0.00           H  
HETATM   57  H20 UNL     1       6.411  -1.495   3.434  1.00  0.00           H  
HETATM   58  H21 UNL     1       4.859  -2.351   3.842  1.00  0.00           H  
HETATM   59  H22 UNL     1       4.893  -0.566   3.762  1.00  0.00           H  
HETATM   60  H23 UNL     1      -2.463  -3.834   2.078  1.00  0.00           H  
HETATM   61  H24 UNL     1      -4.835  -3.628   1.736  1.00  0.00           H  
HETATM   62  H25 UNL     1      -4.734  -3.192  -1.280  1.00  0.00           H  
HETATM   63  H26 UNL     1      -6.217  -3.304  -0.254  1.00  0.00           H  
HETATM   64  H27 UNL     1      -5.971  -1.834  -1.351  1.00  0.00           H  
HETATM   65  H28 UNL     1      -5.125  -0.793   2.163  1.00  0.00           H  
HETATM   66  H29 UNL     1      -6.558  -1.748   1.495  1.00  0.00           H  
HETATM   67  H30 UNL     1      -5.989  -0.195   0.663  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3    4    4
CONECT    3   41   42   43
CONECT    4    5   44
CONECT    5    6   45   46
CONECT    6    7    7   17
CONECT    7    8   37
CONECT    8    9    9   32
CONECT    9   10   11
CONECT   10   47
CONECT   11   12   17   17
CONECT   12   13   13   14
CONECT   14   15   15   27
CONECT   15   16   18
CONECT   16   17
CONECT   18   19   19   25
CONECT   19   20   48
CONECT   20   21   22   22
CONECT   21   49
CONECT   22   23   24
CONECT   23   50
CONECT   24   25   25   51
CONECT   25   26
CONECT   26   27
CONECT   27   28   52
CONECT   28   29   29   53
CONECT   29   30   31
CONECT   30   54   55   56
CONECT   31   57   58   59
CONECT   32   33   33   60
CONECT   33   34   61
CONECT   34   35   36   37
CONECT   35   62   63   64
CONECT   36   65   66   67
END

HMDB0030685
     RDKit          3D
Cycloheterophyllin
 67 71  0  0  0  0  0  0  0  0999 V2000
   -3.8548    3.6614    0.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1039    2.3583    0.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6431    1.6345    1.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227    1.9846   -0.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660    0.8270   -1.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -0.1886   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4590   -1.1200   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9566   -2.1106    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6004   -2.1740    0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114   -3.1211    1.7122 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161   -1.2675    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5848   -1.3336    0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0763   -2.2278    1.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -0.3936   -0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7968    0.5791   -1.0392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    0.5886   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901   -0.2804   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6010    1.5598   -1.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569    2.5280   -2.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073    3.4192   -3.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3630    4.3898   -3.9702 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781    3.3470   -3.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0947    4.2526   -3.6557 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8212    2.3693   -2.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674    1.4778   -1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849    0.5034   -0.7753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7973   -0.4774   -0.0638 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181   -0.5286    1.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9416   -1.5173    1.8512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3976   -2.6720    1.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3213   -1.4785    3.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8593   -3.0641    1.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1611   -2.9361    1.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547   -1.8980    0.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5120   -2.6056   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7013   -1.0724    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8327   -1.0435   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8244    3.3900    1.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0438    4.2160   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122    4.2008    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3923    0.8540    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6449    1.2127    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6541    2.3320    2.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3731    2.7185   -1.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0381    0.3141   -2.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    1.1952   -2.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4960   -3.8162    2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9965    2.6144   -2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3966    4.5242   -4.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7686    4.9862   -4.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8996    2.3204   -2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.4614   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    0.2741    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663   -3.1654    0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8847   -3.4056    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2105   -2.3335    0.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4108   -1.4952    3.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595   -2.3512    3.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8933   -0.5656    3.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629   -3.8340    2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8351   -3.6276    1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -3.1921   -1.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2175   -3.3039   -0.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9708   -1.8341   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1247   -0.7931    2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5583   -1.7480    1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9887   -0.1953    0.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  3
 29 30  1  0
 29 31  1  0
  8 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 34 36  1  0
 34 37  1  0
 17  6  1  0
 25 18  1  0
 37  7  1  0
 17 11  2  0
 27 14  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  3 41  1  0
  3 42  1  0
  3 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
 10 47  1  0
 19 48  1  0
 21 49  1  0
 23 50  1  0
 24 51  1  0
 27 52  1  0
 28 53  1  0
 30 54  1  0
 30 55  1  0
 30 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 33 61  1  0
 35 62  1  0
 35 63  1  0
 35 64  1  0
 36 65  1  0
 36 66  1  0
 36 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3,8-Trihydroxy-11,11-dimethyl-13-(3-methyl-2-butenyl)-6-(2-methyl-1-propenyl)-6H,7H,11H-bis[1]benzopyrano[4,3-b:6',7'-e]pyran-7-one, 9ci	HMDB

Chemical Formula

C₃₀H₃₀O₇

Average Molecular Weight

502.555

Monoisotopic Molecular Weight

502.199153314

IUPAC Name

6,7,15-trihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-13-one

Traditional Name

cycloheterophyllin

CAS Registry Number

36545-53-6

SMILES

CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O

InChI Identifier

InChI=1S/C30H30O7/c1-14(2)7-8-17-27-16(9-10-30(5,6)37-27)25(33)24-26(34)23-22(11-15(3)4)35-21-13-20(32)19(31)12-18(21)29(23)36-28(17)24/h7,9-13,22,31-33H,8H2,1-6H3

InChI Key

ZZPIXEJZTXAVCX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ether
Polyol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110921 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0030685)

Cellular substructure

Membrane (HMDB: HMDB0030685)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030685)

Source

Endogenous

Endogenous (HMDB: HMDB0030685)

Plant

Plant (HMDB: HMDB0030685)

Exogenous

Food

Food (HMDB: HMDB0030685)

Fruit

Tropical fruit

Jackfruit (FooDB: FOOD00384)

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 - 206 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0036 g/L	ALOGPS
logP	5.18	ALOGPS
logP	6.23	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	144.67 m³·mol⁻¹	ChemAxon
Polarizability	55.48 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	219.155	31661259
DarkChem	[M-H]-	215.912	31661259
DeepCCS	[M+H]+	219.487	30932474
DeepCCS	[M-H]-	217.091	30932474
DeepCCS	[M-2H]-	249.977	30932474
DeepCCS	[M+Na]+	225.4	30932474
AllCCS	[M+H]+	220.4	32859911
AllCCS	[M+H-H2O]+	218.3	32859911
AllCCS	[M+NH4]+	222.3	32859911
AllCCS	[M+Na]+	222.8	32859911
AllCCS	[M-H]-	212.7	32859911
AllCCS	[M+Na-2H]-	212.9	32859911
AllCCS	[M+HCOO]-	213.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cycloheterophyllin	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O	5525.5	Standard polar	33892256
Cycloheterophyllin	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O	4284.7	Standard non polar	33892256
Cycloheterophyllin	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C(OC3=C1C=C(O)C(O)=C3)C=C(C)C)C2=O	4137.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cycloheterophyllin,1TMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O)C=C21	3931.7	Semi standard non polar	33892256
Cycloheterophyllin,1TMS,isomer #2	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C)C=C21	3938.6	Semi standard non polar	33892256
Cycloheterophyllin,1TMS,isomer #3	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O)C=C21	3952.8	Semi standard non polar	33892256
Cycloheterophyllin,2TMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C)C=C21	3832.5	Semi standard non polar	33892256
Cycloheterophyllin,2TMS,isomer #2	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O)C=C21	3852.6	Semi standard non polar	33892256
Cycloheterophyllin,2TMS,isomer #3	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	3875.9	Semi standard non polar	33892256
Cycloheterophyllin,3TMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C21	3804.9	Semi standard non polar	33892256
Cycloheterophyllin,1TBDMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O)C=C21	4165.2	Semi standard non polar	33892256
Cycloheterophyllin,1TBDMS,isomer #2	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C21	4173.8	Semi standard non polar	33892256
Cycloheterophyllin,1TBDMS,isomer #3	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C21	4189.8	Semi standard non polar	33892256
Cycloheterophyllin,2TBDMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C21	4230.7	Semi standard non polar	33892256
Cycloheterophyllin,2TBDMS,isomer #2	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C21	4249.7	Semi standard non polar	33892256
Cycloheterophyllin,2TBDMS,isomer #3	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C21	4280.0	Semi standard non polar	33892256
Cycloheterophyllin,3TBDMS,isomer #1	CC(C)=CCC1=C2OC(C)(C)C=CC2=C(O[Si](C)(C)C(C)(C)C)C2=C1OC1=C(C2=O)C(C=C(C)C)OC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C21	4346.1	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 - Cycloheterophyllin GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1210900000-2b9348571f9c2ede2c21	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cycloheterophyllin GC-MS (2 TMS) - 70eV, Positive	splash10-001i-2100029000-1a10b698dc6f89f727b5	2017-10-06	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 - Cycloheterophyllin 10V, Positive-QTOF	splash10-0udi-1301890000-3a9668040559528c86dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Positive-QTOF	splash10-07bb-3103910000-3e34e7b9d27e80266f15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Positive-QTOF	splash10-0pxr-9501100000-7f051663aa9661ab0611	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 10V, Negative-QTOF	splash10-0udi-0000190000-684986bbcc1af6b7bb2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Negative-QTOF	splash10-0udi-1002960000-ab6c73fca49f7aae21e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Negative-QTOF	splash10-0apj-1445900000-e6a2476407cfa534cc22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 10V, Negative-QTOF	splash10-0udi-0000090000-27a32bd6c97a965edc44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Negative-QTOF	splash10-0udi-0000090000-27a32bd6c97a965edc44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Negative-QTOF	splash10-0a4r-0090010000-7e9d5fac0bdd16aa0613	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 10V, Positive-QTOF	splash10-0udi-0000090000-db49500cd3a1fa636786	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 20V, Positive-QTOF	splash10-0udi-0000090000-db49500cd3a1fa636786	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cycloheterophyllin 40V, Positive-QTOF	splash10-0f79-0090250000-7dd066fbdb79c38212a8	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

FDB002604

KNApSAcK ID

C00004064

Chemspider ID

4475345

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316250

PDB ID

Not Available

ChEBI ID

563917

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

Lin CN, Lu CM, Lin HC, Fang SC, Shieh BJ, Hsu MF, Wang JP, Ko FN, Teng CM: Novel antiplatelet constituents from formosan moraceous plants. J Nat Prod. 1996 Sep;59(9):834-8. [PubMed:8864236 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Cycloheterophyllin → 6-{[6,15-dihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-13-oxo-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4,6,8,15,17,21-octaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Cycloheterophyllin → 6-{[7,15-dihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-13-oxo-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4,6,8,15,17,21-octaen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Cycloheterophyllin → 6-{[6,7-dihydroxy-19,19-dimethyl-22-(3-methylbut-2-en-1-yl)-11-(2-methylprop-1-en-1-yl)-13-oxo-2,10,20-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(14),3(12),4(9),5,7,15,17,21-octaen-15-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Cycloheterophyllin (HMDB0030685)

MOL for HMDB0030685 (Cycloheterophyllin)

3D MOL for HMDB0030685 (Cycloheterophyllin)

3D SDF for HMDB0030685 (Cycloheterophyllin)

3D-SDF for HMDB0030685 (Cycloheterophyllin)

PDB for HMDB0030685 (Cycloheterophyllin)

3D PDB for HMDB0030685 (Cycloheterophyllin)

SMILES for HMDB0030685 (Cycloheterophyllin)

INCHI for HMDB0030685 (Cycloheterophyllin)

Structure for HMDB0030685 (Cycloheterophyllin)

3D Structure for HMDB0030685 (Cycloheterophyllin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions