NP-MRD: Showing NP-Card for 6-O-trans-p-Coumaroylshanzhiside methyl ester (NP0137976)

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Record Information

Version

2.0

Created at

2022-05-31 16:41:34 UTC

Updated at

2022-05-31 16:41:34 UTC

NP-MRD ID

NP0137976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-O-trans-p-Coumaroylshanzhiside methyl ester

Description

Methyl (1S,4aS,5R,7S,7aS)-7-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Based on a literature review very few articles have been published on methyl (1S,4aS,5R,7S,7aS)-7-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218412D          

 50 53  0  0  1  0            999 V2000
   -0.9083    2.3234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194    1.2687    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    2.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    3.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0321    4.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871    5.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252    4.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702    3.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4399    0.5529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8580   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556   -0.6979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0263   -0.7704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.9354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.9354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990   -4.4104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135   -3.1729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990   -1.9354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845   -3.1729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 31 30  1  1  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  1  0  0  0
 36 37  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  6  0  0  0
 38 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 41 44  1  0  0  0  0
 31 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  1  0  0  0
 25 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
    3.2019    3.5558    2.5923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394    3.0712    2.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732    2.3141    1.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8187    2.0924    0.3653 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4755    1.8180    0.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    2.0996    1.3391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    1.6825    1.0103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9875    0.5232    0.1600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3268    0.4840   -0.2616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0547   -0.5474    0.3219 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7169   -1.2241   -0.6599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0235   -1.5334   -0.4096 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.8327   -3.3753   -1.9506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9064   -0.3286   -0.1672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8575   -0.6881    0.7795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0719    0.8110    0.4005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3962    1.3840   -0.6967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0180    0.1548    1.2839 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6296   -0.7731    2.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0819    0.6768   -1.0003 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3451    1.0375   -0.6212 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9959   -0.3241   -0.5935 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3787   -0.3165   -0.4651 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699   -1.1514    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -1.9169    1.2076 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425   -1.1468    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1913   -0.3679   -0.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6311   -0.2709   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2968    0.5897   -0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6741    0.7111   -0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4210   -0.0513   -0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8100    0.0709   -0.0405 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7571   -0.9155    0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -1.0342    0.7803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696   -0.7963   -2.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9386   -0.4929   -1.9092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5828   -1.7643   -1.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -0.1688   -3.1850 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254    4.3865    3.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016    3.9710    1.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8505    2.7650    3.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247    2.6926    2.2492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968   -0.3193    0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282   -1.1846    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0846   -2.2851    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4119   -1.5499   -2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6432   -2.4110   -1.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8014   -3.9657   -1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4441   -0.0079   -1.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5525   -0.0031    0.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6736    1.5495    0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6125    2.3278   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4905    0.9450    1.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0625   -0.3148    2.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4506    1.5953   -1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7851    1.5570   -1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4806   -1.0309    0.0983 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9223   -1.7890    1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6526    0.2595   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7486    1.2183   -1.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2021    1.3954   -1.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4257   -0.4850   -0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3705   -1.5028    1.4708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9296   -1.7420    1.4812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7709   -1.8577   -2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -0.1789   -2.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5368   -1.9744   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4252    0.8114   -3.2555 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 23  1  0
 23 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  1  6
 37 21  1  0
 21 22  1  0
 22  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
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 19 20  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  1  0
 35 29  1  0
 22 23  1  0
 19 10  1  0
  8 21  1  0
 27 59  1  0
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 39 71  1  0
 21 56  1  6
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  6 43  1  0
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 12 46  1  1
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 16 51  1  0
 17 52  1  1
 18 53  1  0
 19 54  1  1
 20 55  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  END


  Mrv1652305312218412D          

 50 53  0  0  1  0            999 V2000
   -0.9083    2.3234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194    1.2687    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3292    2.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    3.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0321    4.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2871    5.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2252    4.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702    3.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4399    0.5529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8580   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1921   -2.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556   -0.6979    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0263   -0.7704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.9354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.9354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -3.9979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990   -4.4104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2135   -3.1729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4990   -1.9354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845   -3.1729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 31 30  1  1  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  1  0  0  0
 36 37  1  0  0  0  0
 34 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  6  0  0  0
 38 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 41 44  1  0  0  0  0
 31 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  1  0  0  0
 25 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137976

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)O[C@]1([H])C[C@](C)(O)[C@]2([H])[C@@]1([H])C(=CO[C@@]2([H])O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O13/c1-26(34)9-15(37-17(29)8-5-12-3-6-13(28)7-4-12)18-14(23(33)35-2)11-36-24(19(18)26)39-25-22(32)21(31)20(30)16(10-27)38-25/h3-8,11,15-16,18-22,24-25,27-28,30-32,34H,9-10H2,1-2H3/b8-5+/t15-,16-,18+,19-,20-,21+,22-,24+,25+,26+/m1/s1

> <INCHI_KEY>
ZGUUHRZMAAUFHL-OKHNFGPGSA-N

> <FORMULA>
C26H32O13

> <MOLECULAR_WEIGHT>
552.529

> <EXACT_MASS>
552.18429109

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.39013561473403

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4aS,5R,7S,7aS)-7-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_LOGP>
-0.31169587800000015

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.205520950774224

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.39793568486894

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760192835

> <JCHEM_POLAR_SURFACE_AREA>
201.67

> <JCHEM_REFRACTIVITY>
130.3777

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aS,5R,7S,7aS)-7-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      -1.696   4.337   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -2.726   3.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.232   3.513   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0      -5.263   2.368   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      -4.708   4.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.215   5.297   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.690   6.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.660   7.907   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.136   9.371   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.154   7.586   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.678   6.122   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.281   0.583   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.744   1.408   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       0.821   1.032   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.602  -3.319   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.358  -3.956   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       2.530  -1.303   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      -0.049  -1.438   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.864  -2.073   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.197  -3.613   0.000  0.00  0.00           H+0
HETATM   30  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       3.864  -3.613   0.000  0.00  0.00           H+0
HETATM   33  O   UNK     0       3.864  -6.693   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.198  -7.463   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0       6.531  -8.233   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0       5.198  -9.003   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.864  -9.773   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.531  -6.693   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0       7.865  -5.923   0.000  0.00  0.00           H+0
HETATM   40  O   UNK     0       7.865  -7.463   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0       6.531  -3.613   0.000  0.00  0.00           H+0
HETATM   43  O   UNK     0       7.865  -4.383   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0       5.198  -5.923   0.000  0.00  0.00           H+0
HETATM   46  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       2.530   1.777   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       1.197   2.547   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       3.864   2.547   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       5.198   1.777   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   23                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23   28                                             
CONECT   22   21                                                            
CONECT   23   21   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   47                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   21   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33   44                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36   38                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
CONECT   38   34   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41   31   45   46                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   25   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,4as,5R,7S,7as)-7-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-7-methyl-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-4-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₂O₁₃

Average Mass

552.5290 Da

Monoisotopic Mass

552.18429 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1246012-26-9

SMILES

[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)O[C@]1([H])C[C@](C)(O)[C@]2([H])[C@@]1([H])C(=CO[C@@]2([H])O[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C(=O)OC

InChI Identifier

InChI=1S/C26H32O13/c1-26(34)9-15(37-17(29)8-5-12-3-6-13(28)7-4-12)18-14(23(33)35-2)11-36-24(19(18)26)39-25-22(32)21(31)20(30)16(10-27)38-25/h3-8,11,15-16,18-22,24-25,27-28,30-32,34H,9-10H2,1-2H3/b8-5+/t15-,16-,18+,19-,20-,21+,22-,24+,25+,26+/m1/s1

InChI Key

ZGUUHRZMAAUFHL-OKHNFGPGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
Cinnamic acid ester
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Aromatic monoterpenoid
Monoterpenoid
Bicyclic monoterpenoid
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Oxane
Vinylogous ester
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28424481

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91895356

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6-O-trans-p-Coumaroylshanzhiside methyl ester (NP0137976)

MOL for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

3D MOL for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

3D SDF for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

3D-SDF for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

PDB for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

3D PDB for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

SMILES for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

INCHI for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

Structure for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)

3D Structure for NP0137976 (6-O-trans-p-Coumaroylshanzhiside methyl ester)