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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:54:17 UTC

Update Date

2022-03-07 02:55:26 UTC

HMDB ID

HMDB0037654

Secondary Accession Numbers

HMDB37654

Metabolite Identification

Common Name

Ephedrannin A

Description

Ephedrannin A belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Ephedrannin A has been detected, but not quantified in, fruits. This could make ephedrannin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Ephedrannin A.

Structure

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


  Mrv1652302282012312D          

 41 47  0  0  0  0            999 V2000
   -5.6179    3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3323    2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3323    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6179    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9034    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9034    2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    3.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    1.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4745    2.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7599    3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455    4.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455    2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3311    3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3311    3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -0.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288   -0.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288   -1.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -2.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998   -1.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998   -0.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -2.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6577   -1.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722   -2.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3722   -2.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6577   -3.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -2.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0866   -3.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -2.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    0.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0853   -2.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    1.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6179    0.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0468    3.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    1.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    1.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6166    4.2625    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5 36  1  0  0  0  0
 36  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 18 22  1  0  0  0  0
 27 22  2  0  0  0  0
 23 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 29  1  0  0  0  0
 21 32  1  0  0  0  0
 16 21  2  0  0  0  0
 31 16  1  0  0  0  0
 30 31  2  0  0  0  0
 32 33  2  0  0  0  0
 30 33  1  0  0  0  0
 20 34  2  0  0  0  0
 32 35  1  0  0  0  0
 30 40  1  0  0  0  0
  4 37  1  0  0  0  0
  2 38  1  0  0  0  0
  8 39  1  1  0  0  0
  9 40  1  6  0  0  0
 15 41  1  0  0  0  0
 36 31  1  6  0  0  0
M  END

HMDB0037654
     RDKit          3D
Ephedrannin A
 61 67  0  0  0  0  0  0  0  0999 V2000
    2.3219    3.6222   -2.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2155    2.6826   -2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    2.2092   -1.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    2.8272   -1.7290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2501    1.1830   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065    0.6323    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    1.2138    0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7140    0.6104    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833   -0.6015    1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6924   -1.1391    2.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3376   -1.2165    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -0.6124    0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524    0.6290   -0.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.0629   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4625   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    0.8793   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    1.9129   -2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1629    2.5500   -2.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    3.5904   -3.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    2.1099   -1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438    0.2262   -0.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.3076    0.4924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8811    0.4292    1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054    0.9986    2.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8624    1.6861    2.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    1.8229    2.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1478    2.5175    2.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1460    1.2642    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0828    0.5887    0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673   -1.6917    0.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0678   -2.4166   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392   -3.5855   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -4.3335   -1.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -5.5029   -2.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2128   -3.8847   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585   -2.7030   -0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743   -2.2761   -1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841   -1.9304   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530   -0.6804    0.3577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4963   -0.2638    1.2920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5641   -1.1981    2.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6423    3.5675   -2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413    2.1707   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6664    1.1085    0.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7091   -2.0341    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242   -2.1696    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2952   -1.0777    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522    2.2369   -2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    3.9208   -3.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    0.9029    2.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7894    2.1329    3.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1725    3.5252    2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0529    1.3556    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1432    0.1352   -0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4645   -3.9239   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -5.8187   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5623   -4.4570   -2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -2.8421   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5836   -0.8272    0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909    0.7726    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -2.0455    2.1292 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
  3  5  2  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  2  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  1
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 22 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 20  2  1  0
 40 22  1  0
 12  6  1  0
 20 14  1  0
 29 23  1  0
 38 31  1  0
 39 15  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 17 48  1  0
 19 49  1  0
 24 50  1  0
 25 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 32 55  1  0
 34 56  1  0
 35 57  1  0
 37 58  1  0
 39 59  1  1
 40 60  1  1
 41 61  1  0
M  END


  Mrv1652302282012312D          

 41 47  0  0  0  0            999 V2000
   -5.6179    3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3323    2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3323    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6179    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9034    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9034    2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    3.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4745    1.7875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4745    2.6125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7599    3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455    4.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455    2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3311    3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3311    3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -0.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288   -0.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2288   -1.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -2.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998   -1.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998   -0.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -2.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3722   -2.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6577   -3.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -2.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0866   -3.2862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143   -2.8737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    0.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854   -0.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0854    0.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0853   -2.0487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.8111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1889    1.3750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6179    0.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0468    3.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7599    1.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998    1.6638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6166    4.2625    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5 36  1  0  0  0  0
 36  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 12 10  2  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 18 22  1  0  0  0  0
 27 22  2  0  0  0  0
 23 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 29  1  0  0  0  0
 21 32  1  0  0  0  0
 16 21  2  0  0  0  0
 31 16  1  0  0  0  0
 30 31  2  0  0  0  0
 32 33  2  0  0  0  0
 30 33  1  0  0  0  0
 20 34  2  0  0  0  0
 32 35  1  0  0  0  0
 30 40  1  0  0  0  0
  4 37  1  0  0  0  0
  2 38  1  0  0  0  0
  8 39  1  1  0  0  0
  9 40  1  6  0  0  0
 15 41  1  0  0  0  0
 36 31  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0037654

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C30H20O11/c31-14-5-1-12(2-6-14)27-26(37)25(36)22-18(35)11-20-23(28(22)39-27)24-21-17(34)9-16(33)10-19(21)40-30(41-20,29(24)38)13-3-7-15(32)8-4-13/h1-11,24,29,31-35,37-38H/t24-,29-,30+/m0/s1

> <INCHI_KEY>
GPBSBBVDERLESN-QZFRTWIZSA-N

> <FORMULA>
C30H20O11

> <MOLECULAR_WEIGHT>
556.4732

> <EXACT_MASS>
556.100561482

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
54.54784110938584

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
4.558855188666667

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.299883314368577

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.165066351673676

> <JCHEM_PKA_STRONGEST_BASIC>
-3.883854989685802

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
143.09700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037654
     RDKit          3D
Ephedrannin A
 61 67  0  0  0  0  0  0  0  0999 V2000
    2.3219    3.6222   -2.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2155    2.6826   -2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    2.2092   -1.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    2.8272   -1.7290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2501    1.1830   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065    0.6323    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    1.2138    0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7140    0.6104    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833   -0.6015    1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6924   -1.1391    2.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3376   -1.2165    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -0.6124    0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524    0.6290   -0.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.0629   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4625   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    0.8793   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    1.9129   -2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1629    2.5500   -2.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    3.5904   -3.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    2.1099   -1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438    0.2262   -0.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.3076    0.4924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8811    0.4292    1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054    0.9986    2.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8624    1.6861    2.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    1.8229    2.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1478    2.5175    2.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1460    1.2642    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0828    0.5887    0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673   -1.6917    0.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0678   -2.4166   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392   -3.5855   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -4.3335   -1.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -5.5029   -2.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2128   -3.8847   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585   -2.7030   -0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743   -2.2761   -1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841   -1.9304   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530   -0.6804    0.3577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4963   -0.2638    1.2920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5641   -1.1981    2.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6423    3.5675   -2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413    2.1707   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6664    1.1085    0.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7091   -2.0341    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242   -2.1696    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2952   -1.0777    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522    2.2369   -2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    3.9208   -3.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    0.9029    2.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7894    2.1329    3.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1725    3.5252    2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0529    1.3556    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1432    0.1352   -0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4645   -3.9239   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -5.8187   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5623   -4.4570   -2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -2.8421   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5836   -0.8272    0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909    0.7726    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -2.0455    2.1292 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
  3  5  2  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  2  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  1
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 22 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 20  2  1  0
 40 22  1  0
 12  6  1  0
 20 14  1  0
 29 23  1  0
 38 31  1  0
 39 15  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 17 48  1  0
 19 49  1  0
 24 50  1  0
 25 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 32 55  1  0
 34 56  1  0
 35 57  1  0
 37 58  1  0
 39 59  1  1
 40 60  1  1
 41 61  1  0
M  END

HEADER    PROTEIN                                 28-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-FEB-20         0                                  
HETATM    1  C   UNK     0     -10.487   5.647   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.820   4.877   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.820   3.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.487   2.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.153   3.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.153   4.877   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.819   5.647   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.486   3.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.486   4.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.152   5.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.818   7.957   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.152   7.187   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.818   4.877   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.485   5.647   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.485   7.187   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.693  -0.744   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.027  -1.514   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.027  -3.054   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.693  -3.824   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.360  -3.054   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.360  -1.514   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.361  -3.824   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.694  -3.054   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.028  -3.824   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.028  -5.364   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.694  -6.134   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.361  -5.364   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -11.362  -6.134   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.693  -5.364   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.360   1.566   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.693   0.796   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.026  -0.744   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.026   0.796   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.026  -3.824   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.692  -1.514   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.819   2.567   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -10.487   1.027   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -13.154   5.647   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.152   2.567   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.360   3.106   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.151   7.957   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   37                                                  
CONECT    5    4    6   36                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6    9                                                       
CONECT    8   36    9   39                                                  
CONECT    9    8    7   10   40                                             
CONECT   10    9   12   13                                                  
CONECT   11   12   15                                                       
CONECT   12   10   11                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   41                                                  
CONECT   16   17   21   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   32   16                                                  
CONECT   22   18   27   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   22   26                                                       
CONECT   28   25                                                            
CONECT   29   19                                                            
CONECT   30   31   33   40                                                  
CONECT   31   16   30   36                                                  
CONECT   32   21   33   35                                                  
CONECT   33   32   30                                                       
CONECT   34   20                                                            
CONECT   35   32                                                            
CONECT   36    5    8   31                                                  
CONECT   37    4                                                            
CONECT   38    2                                                            
CONECT   39    8                                                            
CONECT   40   30    9                                                       
CONECT   41   15                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

COMPND    HMDB0037654
HETATM    1  O1  UNL     1       2.322   3.622  -2.873  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.216   2.683  -2.065  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.352   2.209  -1.421  1.00  0.00           C  
HETATM    4  O2  UNL     1       4.566   2.827  -1.729  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.250   1.183  -0.535  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.407   0.632   0.173  1.00  0.00           C  
HETATM    7  C5  UNL     1       5.631   1.214   0.227  1.00  0.00           C  
HETATM    8  C6  UNL     1       6.714   0.610   0.882  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.583  -0.601   1.500  1.00  0.00           C  
HETATM   10  O3  UNL     1       7.692  -1.139   2.126  1.00  0.00           O  
HETATM   11  C8  UNL     1       5.338  -1.217   1.460  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.285  -0.612   0.815  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.052   0.629  -0.285  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.996   1.063  -0.879  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.213   0.462  -0.586  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.383   0.879  -1.178  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.334   1.913  -2.080  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.163   2.550  -2.416  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.060   3.590  -3.315  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.001   2.110  -1.802  1.00  0.00           C  
HETATM   21  O6  UNL     1      -2.544   0.226  -0.821  1.00  0.00           O  
HETATM   22  C16 UNL     1      -2.779  -0.308   0.492  1.00  0.00           C  
HETATM   23  C17 UNL     1      -3.881   0.429   1.108  1.00  0.00           C  
HETATM   24  C18 UNL     1      -3.805   0.999   2.358  1.00  0.00           C  
HETATM   25  C19 UNL     1      -4.862   1.686   2.921  1.00  0.00           C  
HETATM   26  C20 UNL     1      -6.050   1.823   2.227  1.00  0.00           C  
HETATM   27  O7  UNL     1      -7.148   2.517   2.771  1.00  0.00           O  
HETATM   28  C21 UNL     1      -6.146   1.264   0.981  1.00  0.00           C  
HETATM   29  C22 UNL     1      -5.083   0.589   0.449  1.00  0.00           C  
HETATM   30  O8  UNL     1      -3.067  -1.692   0.326  1.00  0.00           O  
HETATM   31  C23 UNL     1      -2.068  -2.417  -0.334  1.00  0.00           C  
HETATM   32  C24 UNL     1      -2.439  -3.586  -0.972  1.00  0.00           C  
HETATM   33  C25 UNL     1      -1.498  -4.333  -1.636  1.00  0.00           C  
HETATM   34  O9  UNL     1      -1.876  -5.503  -2.273  1.00  0.00           O  
HETATM   35  C26 UNL     1      -0.213  -3.885  -1.640  1.00  0.00           C  
HETATM   36  C27 UNL     1       0.158  -2.703  -0.993  1.00  0.00           C  
HETATM   37  O10 UNL     1       1.474  -2.276  -1.016  1.00  0.00           O  
HETATM   38  C28 UNL     1      -0.784  -1.930  -0.313  1.00  0.00           C  
HETATM   39  C29 UNL     1      -0.353  -0.680   0.358  1.00  0.00           C  
HETATM   40  C30 UNL     1      -1.496  -0.264   1.292  1.00  0.00           C  
HETATM   41  O11 UNL     1      -1.564  -1.198   2.314  1.00  0.00           O  
HETATM   42  H1  UNL     1       4.642   3.567  -2.376  1.00  0.00           H  
HETATM   43  H2  UNL     1       5.841   2.171  -0.210  1.00  0.00           H  
HETATM   44  H3  UNL     1       7.666   1.108   0.904  1.00  0.00           H  
HETATM   45  H4  UNL     1       7.709  -2.034   2.615  1.00  0.00           H  
HETATM   46  H5  UNL     1       5.224  -2.170   1.949  1.00  0.00           H  
HETATM   47  H6  UNL     1       3.295  -1.078   0.771  1.00  0.00           H  
HETATM   48  H7  UNL     1      -2.252   2.237  -2.545  1.00  0.00           H  
HETATM   49  H8  UNL     1      -0.900   3.921  -3.773  1.00  0.00           H  
HETATM   50  H9  UNL     1      -2.882   0.903   2.915  1.00  0.00           H  
HETATM   51  H10 UNL     1      -4.789   2.133   3.916  1.00  0.00           H  
HETATM   52  H11 UNL     1      -7.173   3.525   2.557  1.00  0.00           H  
HETATM   53  H12 UNL     1      -7.053   1.356   0.426  1.00  0.00           H  
HETATM   54  H13 UNL     1      -5.143   0.135  -0.557  1.00  0.00           H  
HETATM   55  H14 UNL     1      -3.465  -3.924  -0.956  1.00  0.00           H  
HETATM   56  H15 UNL     1      -2.838  -5.819  -2.260  1.00  0.00           H  
HETATM   57  H16 UNL     1       0.562  -4.457  -2.160  1.00  0.00           H  
HETATM   58  H17 UNL     1       2.147  -2.842  -1.510  1.00  0.00           H  
HETATM   59  H18 UNL     1       0.584  -0.827   0.944  1.00  0.00           H  
HETATM   60  H19 UNL     1      -1.291   0.773   1.686  1.00  0.00           H  
HETATM   61  H20 UNL     1      -1.116  -2.046   2.129  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4    5    5
CONECT    4   42
CONECT    5    6   13
CONECT    6    7    7   12
CONECT    7    8   43
CONECT    8    9    9   44
CONECT    9   10   11
CONECT   10   45
CONECT   11   12   12   46
CONECT   12   47
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   39
CONECT   16   17   17   21
CONECT   17   18   48
CONECT   18   19   20   20
CONECT   19   49
CONECT   21   22
CONECT   22   23   30   40
CONECT   23   24   24   29
CONECT   24   25   50
CONECT   25   26   26   51
CONECT   26   27   28
CONECT   27   52
CONECT   28   29   29   53
CONECT   29   54
CONECT   30   31
CONECT   31   32   32   38
CONECT   32   33   55
CONECT   33   34   35   35
CONECT   34   56
CONECT   35   36   57
CONECT   36   37   38   38
CONECT   37   58
CONECT   38   39
CONECT   39   40   59
CONECT   40   41   60
CONECT   41   61
END

HMDB0037654
     RDKit          3D
Ephedrannin A
 61 67  0  0  0  0  0  0  0  0999 V2000
    2.3219    3.6222   -2.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2155    2.6826   -2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    2.2092   -1.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5663    2.8272   -1.7290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2501    1.1830   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4065    0.6323    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311    1.2138    0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7140    0.6104    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5833   -0.6015    1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6924   -1.1391    2.1263 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3376   -1.2165    1.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854   -0.6124    0.8145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524    0.6290   -0.2847 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.0629   -0.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4625   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827    0.8793   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    1.9129   -2.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1629    2.5500   -2.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    3.5904   -3.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    2.1099   -1.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5438    0.2262   -0.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.3076    0.4924 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8811    0.4292    1.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054    0.9986    2.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8624    1.6861    2.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0502    1.8229    2.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1478    2.5175    2.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1460    1.2642    0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0828    0.5887    0.4492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0673   -1.6917    0.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0678   -2.4166   -0.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392   -3.5855   -0.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -4.3335   -1.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -5.5029   -2.2735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2128   -3.8847   -1.6395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585   -2.7030   -0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743   -2.2761   -1.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7841   -1.9304   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3530   -0.6804    0.3577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4963   -0.2638    1.2920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5641   -1.1981    2.3142 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6423    3.5675   -2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413    2.1707   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6664    1.1085    0.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7091   -2.0341    2.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242   -2.1696    1.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2952   -1.0777    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2522    2.2369   -2.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9001    3.9208   -3.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    0.9029    2.9151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7894    2.1329    3.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1725    3.5252    2.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0529    1.3556    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1432    0.1352   -0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4645   -3.9239   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381   -5.8187   -2.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5623   -4.4570   -2.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -2.8421   -1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5836   -0.8272    0.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909    0.7726    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -2.0455    2.1292 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
  3  5  2  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  2  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21 22  1  0
 22 23  1  1
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 22 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 20  2  1  0
 40 22  1  0
 12  6  1  0
 20 14  1  0
 29 23  1  0
 38 31  1  0
 39 15  1  0
  4 42  1  0
  7 43  1  0
  8 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 17 48  1  0
 19 49  1  0
 24 50  1  0
 25 51  1  0
 27 52  1  0
 28 53  1  0
 29 54  1  0
 32 55  1  0
 34 56  1  0
 35 57  1  0
 37 58  1  0
 39 59  1  1
 40 60  1  1
 41 61  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavone	HMDB
3,5,11,13,15-Pentahydroxy-2,8-bis(4-hydroxyphenyl)-8,14-methano-4H,14H-1-benzopyrano[7,8-D][1,3]benzodioxocin-4-one, 9ci	HMDB
ent-Epiafzelechin(2a->o-7,4a->8)kaempferol	HMDB
Ephedrannin a	MeSH

Chemical Formula

C₃₀H₂₀O₁₁

Average Molecular Weight

556.4732

Monoisotopic Molecular Weight

556.100561482

IUPAC Name

(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

Traditional Name

(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

CAS Registry Number

82001-39-6

SMILES

O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O

InChI Identifier

InChI=1S/C30H20O11/c31-14-5-1-12(2-6-14)27-26(37)25(36)22-18(35)11-20-23(28(22)39-27)24-21-17(34)9-16(33)10-19(21)40-30(41-20,29(24)38)13-3-7-15(32)8-4-13/h1-11,24,29,31-35,37-38H/t24-,29-,30+/m0/s1

InChI Key

GPBSBBVDERLESN-QZFRTWIZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
Pyranoflavonoid
3-hydroxyflavone
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Flavone
Hydroxyflavonoid
Flavan
Pyranochromene
Chromone
Chromane
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037654)

Cellular substructure

Membrane (HMDB: HMDB0037654)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037654)

Source

Exogenous

Food

Food (HMDB: HMDB0037654)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0037654)

Not Available

Nutrient (HMDB: HMDB0037654)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	360 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.67 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	3.31	ALOGPS
logP	4.56	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.17	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	143.1 m³·mol⁻¹	ChemAxon
Polarizability	54.55 Å³	ChemAxon
Number of Rings	7	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]+	226.56	31661259
DarkChem	[M-H]-	226.358	31661259
DeepCCS	[M+H]+	217.514	30932474
DeepCCS	[M-H]-	215.619	30932474
DeepCCS	[M-2H]-	249.009	30932474
DeepCCS	[M+Na]+	223.183	30932474
AllCCS	[M+H]+	232.8	32859911
AllCCS	[M+H-H2O]+	231.0	32859911
AllCCS	[M+NH4]+	234.5	32859911
AllCCS	[M+Na]+	235.0	32859911
AllCCS	[M-H]-	219.4	32859911
AllCCS	[M+Na-2H]-	220.1	32859911
AllCCS	[M+HCOO]-	221.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ephedrannin A	O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O	7365.3	Standard polar	33892256
Ephedrannin A	O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O	4866.1	Standard non polar	33892256
Ephedrannin A	O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O	5577.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ephedrannin A,1TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H]2C3=C(O)C=C(O)C=C3O[C@]1(C1=CC=C(O)C=C1)OC1=CC(O)=C3C(=O)C(O)=C(C4=CC=C(O)C=C4)OC3=C12	5487.9	Semi standard non polar	33892256
Ephedrannin A,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C(O)=C(C1=CC=C(O)C=C1)O3)[C@@H]1C3=C(O)C=C(O)C=C3O[C@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5494.3	Semi standard non polar	33892256
Ephedrannin A,1TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O	5456.6	Semi standard non polar	33892256
Ephedrannin A,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5536.9	Semi standard non polar	33892256
Ephedrannin A,1TMS,isomer #5	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5545.9	Semi standard non polar	33892256
Ephedrannin A,1TMS,isomer #6	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5542.1	Semi standard non polar	33892256
Ephedrannin A,1TMS,isomer #7	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5515.3	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5383.7	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #10	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O[Si](C)(C)C)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5398.9	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #11	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5412.3	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #12	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5320.7	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #13	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5360.4	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #14	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O[Si](C)(C)C)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5340.9	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #15	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5313.0	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #16	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5410.9	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #17	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5411.5	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #18	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5401.6	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #19	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5435.4	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O[Si](C)(C)C	5369.9	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #20	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5422.5	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #21	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5409.3	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5393.3	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C(O)=C(C1=CC=C(O)C=C1)O3)[C@@H]1C3=C(O)C=C(O)C=C3O[C@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5332.8	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #5	C[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O[Si](C)(C)C	5291.3	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5362.3	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5387.5	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #8	C[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O[Si](C)(C)C)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O	5323.2	Semi standard non polar	33892256
Ephedrannin A,2TMS,isomer #9	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O[Si](C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5388.9	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5215.9	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #10	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5194.5	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #11	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5146.0	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #12	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5180.7	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #13	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5154.0	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #14	C[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O[Si](C)(C)C)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O[Si](C)(C)C	5123.8	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #15	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5109.9	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #16	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5148.1	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #17	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5203.8	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #18	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5190.0	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #19	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5225.2	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O[Si](C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5222.1	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #20	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5199.3	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #21	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O[Si](C)(C)C)=C4C(=O)C(O[Si](C)(C)C)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5154.8	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #22	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O[Si](C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5183.2	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #23	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@H]1C3=C(C=C(O[Si](C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5214.6	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #24	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5264.4	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #25	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5221.6	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #26	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5163.4	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #27	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5148.9	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #28	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5157.9	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #29	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5185.6	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5165.1	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #30	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5196.0	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #31	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5161.7	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #32	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5205.5	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #33	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5243.6	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #34	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5222.5	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #35	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5251.9	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5222.3	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #5	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5265.0	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #6	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5196.2	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #7	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O[Si](C)(C)C)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O[Si](C)(C)C	5145.3	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #8	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O[Si](C)(C)C)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O[Si](C)(C)C	5123.5	Semi standard non polar	33892256
Ephedrannin A,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5163.9	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@H]1C3=C(C=C(O[Si](C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5028.9	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #10	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5077.0	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #11	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	4989.8	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #12	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5003.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #13	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	4981.9	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #14	C[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O[Si](C)(C)C)=C4C(=O)C(O[Si](C)(C)C)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O[Si](C)(C)C	4962.7	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #15	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	4958.6	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #16	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	4969.7	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #17	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5010.9	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #18	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	4997.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #19	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	4992.3	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5025.1	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #20	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	4970.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #21	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5008.5	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #22	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	4993.5	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #23	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5013.8	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #24	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5044.8	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #25	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5052.7	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #26	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5023.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #27	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5020.0	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #28	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5056.0	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #29	C[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@H]1C3=C(C=C(O[Si](C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	4996.9	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5047.6	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #30	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5055.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #31	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	4996.6	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #32	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5034.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #33	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	4997.0	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #34	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5034.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #35	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C)C=C6)OC6=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5047.6	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5078.8	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O[Si](C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C	5041.4	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5063.1	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #7	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5094.6	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #8	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C)C=C1	5031.9	Semi standard non polar	33892256
Ephedrannin A,4TMS,isomer #9	C[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C)C5=O)O2)[C@@H]3O[Si](C)(C)C)C=C1	5060.2	Semi standard non polar	33892256
Ephedrannin A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H]2C3=C(O)C=C(O)C=C3O[C@]1(C1=CC=C(O)C=C1)OC1=CC(O)=C3C(=O)C(O)=C(C4=CC=C(O)C=C4)OC3=C12	5685.0	Semi standard non polar	33892256
Ephedrannin A,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C(O)=C(C1=CC=C(O)C=C1)O3)[C@@H]1C3=C(O)C=C(O)C=C3O[C@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5723.0	Semi standard non polar	33892256
Ephedrannin A,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O	5702.0	Semi standard non polar	33892256
Ephedrannin A,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5748.0	Semi standard non polar	33892256
Ephedrannin A,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5750.9	Semi standard non polar	33892256
Ephedrannin A,1TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5751.4	Semi standard non polar	33892256
Ephedrannin A,1TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5730.8	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C(C)(C)C	5840.8	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5862.1	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C(C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5879.5	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5829.7	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C(C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5840.6	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5826.4	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5812.8	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C(C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5900.9	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #17	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5881.9	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #18	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5871.6	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5897.4	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O[Si](C)(C)C(C)(C)C	5806.9	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #20	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5879.9	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #21	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5869.0	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C(C)(C)C)C=C1	5824.8	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C(O)=C(C1=CC=C(O)C=C1)O3)[C@@H]1C3=C(O)C=C(O)C=C3O[C@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C(C)(C)C	5787.1	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O[Si](C)(C)C(C)(C)C	5771.5	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C(C)(C)C)C=C1	5812.2	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5866.8	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O	5810.4	Semi standard non polar	33892256
Ephedrannin A,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O[Si](C)(C)C(C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5860.6	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C(C)(C)C	5862.4	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C(C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C(C)(C)C)C=C1	5859.1	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C(C)(C)C)C5=O)O2)[C@@H]3O[Si](C)(C)C(C)(C)C)C=C1	5785.3	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C(C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C(C)(C)C)C=C1	5865.2	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C(C)(C)C)C=C1	5824.7	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C=C2)OC2=C3C(=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O)O[C@@]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2[C@@H]3[C@@H]1O[Si](C)(C)C(C)(C)C	5732.2	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C(C)(C)C)C=C1	5757.2	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5814.0	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #17	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C(C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5936.4	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #18	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5925.1	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5903.9	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O[Si](C)(C)C(C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C(C)(C)C	5865.6	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #20	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C(C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C(C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5854.3	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #21	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O	5812.2	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #22	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O[Si](C)(C)C(C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5816.4	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #23	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@H]1C3=C(C=C(O[Si](C)(C)C(C)(C)C)C4=C3OC(C3=CC=C(O)C=C3)=C(O)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5892.9	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #24	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C(C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5939.4	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #25	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O[Si](C)(C)C(C)(C)C)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5947.4	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #26	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C(C)(C)C)C=C6)OC6=CC(O)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5859.8	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #27	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5826.4	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #28	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5830.3	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #29	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C(C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5863.6	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O[Si](C)(C)C(C)(C)C	5783.9	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #30	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O[Si](C)(C)C(C)(C)C)C5=O)O2)[C@@H]3O)C=C1	5858.1	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #31	CC(C)(C)[Si](C)(C)OC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@H]1C3=C(C=C(O)C4=C3OC(C3=CC=C(O)C=C3)=C(O[Si](C)(C)C(C)(C)C)C4=O)O[C@@](C3=CC=C(O)C=C3)(O2)[C@H]1O	5807.1	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #32	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C(C)(C)C)C=C6)OC6=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5941.9	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #33	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O[Si](C)(C)C(C)(C)C)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5941.5	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #34	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O)C=C1	5904.0	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #35	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O)C=C1	5935.0	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C(C)(C)C)C=C1	5879.4	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C(C)(C)C)C=C1	5899.8	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@]23OC4=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C4[C@@H](C4=C(C=C(O)C5=C4OC(C4=CC=C(O)C=C4)=C(O)C5=O)O2)[C@@H]3O[Si](C)(C)C(C)(C)C)C=C1	5859.8	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O[Si](C)(C)C(C)(C)C)=C4C(=O)C(O)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O[Si](C)(C)C(C)(C)C	5805.8	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)O[C@]1(C3=CC=C(O)C=C3)OC3=CC(O)=C4C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C5=CC=C(O)C=C5)OC4=C3[C@H]2[C@@H]1O[Si](C)(C)C(C)(C)C	5735.8	Semi standard non polar	33892256
Ephedrannin A,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C4O[C@@]5(C6=CC=C(O)C=C6)OC6=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C6[C@@H](C4=C3O2)[C@@H]5O[Si](C)(C)C(C)(C)C)C=C1	5834.3	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 - Ephedrannin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-002r-0030290000-afbe0568fb9d4a9bd8b5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (1 TMS) - 70eV, Positive	splash10-009i-9000043000-5e9de233dd1d4d447257	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS ("Ephedrannin A,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ephedrannin A GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-15	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 - Ephedrannin A 10V, Positive-QTOF	splash10-0a4i-0000090000-c9e2c206ef81ca356562	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 20V, Positive-QTOF	splash10-0ap0-0020090000-4da7fbd03d990273711f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 40V, Positive-QTOF	splash10-0002-9211010000-bb8a33f5767669710730	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 10V, Negative-QTOF	splash10-0a4i-0010190000-ec195d53109cff7da707	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 20V, Negative-QTOF	splash10-0a4i-0130290000-00196a1994a008185194	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 40V, Negative-QTOF	splash10-00pi-1950010000-5e560630a0e079428932	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 10V, Negative-QTOF	splash10-0a4i-0000090000-8fca8045555f7d8ab006	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 20V, Negative-QTOF	splash10-0a4i-0000490000-dc667195cb5d0205763f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 40V, Negative-QTOF	splash10-05gi-2302930000-c718c69f96b57d9589a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 10V, Positive-QTOF	splash10-0a4i-0000090000-487941680bf9ccc20dd2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 20V, Positive-QTOF	splash10-0a4i-0000090000-012c3f7567cf53d63268	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ephedrannin A 40V, Positive-QTOF	splash10-05fr-2000940000-2013fe3e7da1452ec6da	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

FDB016776

KNApSAcK ID

C00009274

Chemspider ID

10290141

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21676348

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1862951

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 Ephedrannin A (HMDB0037654)

MOL for HMDB0037654 (Ephedrannin A)

3D MOL for HMDB0037654 (Ephedrannin A)

3D SDF for HMDB0037654 (Ephedrannin A)

3D-SDF for HMDB0037654 (Ephedrannin A)

PDB for HMDB0037654 (Ephedrannin A)

3D PDB for HMDB0037654 (Ephedrannin A)

SMILES for HMDB0037654 (Ephedrannin A)

INCHI for HMDB0037654 (Ephedrannin A)

Structure for HMDB0037654 (Ephedrannin A)

3D Structure for HMDB0037654 (Ephedrannin A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra