NP-MRD: Showing NP-Card for (8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate (NP0198750)

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Record Information

Version

1.0

Created at

2022-09-04 17:15:19 UTC

Updated at

2022-09-04 17:15:20 UTC

NP-MRD ID

NP0198750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate

Description

Heteroclitalignan D belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. (8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate is found in Kadsura heteroclita. It was first documented in 2006 (PMID: 16534740). Based on a literature review very few articles have been published on heteroclitalignan D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219152D          

 43 47  0  0  1  0            999 V2000
    4.7112    1.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661    1.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    3.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6140    2.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104    2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0382    1.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    0.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230    1.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337    0.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658    0.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8180    3.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    3.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    3.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    2.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024    2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194    1.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2651    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    1.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    3.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6257    4.6734    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0152    5.2713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218    6.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    6.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6738    6.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057    6.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014    6.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0651    7.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332    7.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376    7.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419    5.0828    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1177    5.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379    4.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3853    5.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8126    5.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473    4.1495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4660    4.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987    4.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9187    5.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8859    4.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  6  0  0  0
 36 39  1  0  0  0  0
  5 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END

     RDKit          3D

 77 81  0  0  0  0  0  0  0  0999 V2000
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   -3.1157    2.0289    2.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4118    1.2569    1.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145    1.8561    0.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0258    1.0919   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0584   -0.2933    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7096   -0.9341    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153   -2.3010    1.1014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -2.9725    1.8513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3961   -0.1398    1.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0724   -0.7723    2.9445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -1.0543    4.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5165   -1.3711   -0.8002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510   -1.5788   -1.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -2.7321   -1.9948 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2884   -5.5784   -2.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -4.9411   -2.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2333   -0.3313   -0.0689 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4416   -0.6046    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111   -1.1821   -0.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7186   -0.2504    1.9106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819    0.3639    2.6816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0949    0.6846    4.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296    0.3849    4.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2876   -0.2372    3.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9729   -0.5515    2.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3985    0.5526   -2.1694 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4553    0.8358   -3.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867    1.7332   -1.3560 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5725    2.9576   -2.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7418    1.8202   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    2.0272   -1.0992 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1102    2.1446   -2.3059 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4603    3.4745   -3.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5655    4.3478   -1.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4547    3.6499    1.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966    3.8190    3.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7500    2.9354    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4061   -2.1637    4.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -2.8951   -2.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0456   -0.3064   -0.5372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7425   -6.0757   -3.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0078   -6.3168   -1.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7563   -1.1645   -1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7929    0.6210    2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3842    1.1666    4.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.6369    5.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2713   -0.4727    4.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786   -1.0354    1.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824    0.3018   -2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    1.0500   -2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5591   -0.1385   -3.8031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    3.0072   -3.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4194    3.8457   -1.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6365    2.8823   -2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4868    2.4719   -0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
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 16 23  1  0
 23 22  1  0
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 17 18  2  0
 18 19  1  0
 19 20  1  0
 14 24  1  0
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 36 38  1  1
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 40 41  1  0
 41 42  1  0
 41 43  2  0
 10  3  1  0
 18 13  1  0
 33 28  1  0
 39  5  1  0
 17 16  1  0
  1 44  1  0
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  4 47  1  0
  9 48  1  0
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  9 50  1  0
 12 51  1  0
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 15 54  1  0
 22 58  1  0
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 24 60  1  6
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 35 68  1  0
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 37 70  1  0
 37 71  1  0
 37 72  1  0
 38 73  1  0
 39 74  1  1
 42 75  1  0
 42 76  1  0
 42 77  1  0
M  END


  Mrv1652309042219152D          

 43 47  0  0  1  0            999 V2000
    4.7112    1.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661    1.7896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393    2.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    2.9379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    3.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6140    2.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104    2.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0382    1.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    0.3235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230    1.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337    0.8119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0658    0.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8180    3.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087    3.8775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4163    3.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8320    3.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4226    2.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024    2.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194    1.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2651    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    1.8415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6397    3.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6257    4.6734    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0152    5.2713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0218    6.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    6.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6738    6.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4057    6.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1014    6.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0651    7.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332    7.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6376    7.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419    5.0828    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1177    5.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1379    4.8658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3853    5.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8126    5.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5473    4.1495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4660    4.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0987    4.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9187    5.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8859    4.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  6  0  0  0
 36 39  1  0  0  0  0
  5 39  1  0  0  0  0
 39 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0198750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(OC)=C1OC)C1=C(C=C3OCOC3=C1OC)[C@H](OC(=O)C1=CC=CC=C1)[C@H](C)[C@](C)(O)[C@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H34O11/c1-16-25(43-31(34)18-11-9-8-10-12-18)19-13-22-27(41-15-40-22)29(39-7)23(19)24-20(30(32(16,3)35)42-17(2)33)14-21(36-4)26(37-5)28(24)38-6/h8-14,16,25,30,35H,15H2,1-7H3/t16-,25+,30-,32-/m0/s1

> <INCHI_KEY>
UJJWRJWLPZAYGS-MLDYHGJLSA-N

> <FORMULA>
C32H34O11

> <MOLECULAR_WEIGHT>
594.613

> <EXACT_MASS>
594.210111915

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.673907860674525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,9S,10S,11R)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate

> <JCHEM_LOGP>
4.152279528666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.588079100769505

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4163742013234177

> <JCHEM_POLAR_SURFACE_AREA>
128.21

> <JCHEM_REFRACTIVITY>
152.67310000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(8S,9S,10S,11R)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.794   3.712   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.217   3.341   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.673   3.944   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.680   5.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.350   6.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.013   5.496   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.006   3.956   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.938   2.314   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.848   0.604   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.336   3.180   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.730   1.516   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.723   0.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.527   5.901   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.763   7.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.777   7.245   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.553   5.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.789   4.577   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.751   4.571   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.343   3.077   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.495   1.532   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.824   3.437   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.228   4.070   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.061   5.601   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.168   8.724   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.028   9.840   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.041  11.411   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.407  12.122   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.258  12.239   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.624  11.528   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.923  12.356   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.855  13.895   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.489  14.605   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.190  13.777   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.505   9.488   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.086  11.077   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.991   9.083   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.453  10.609   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.250  10.129   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       4.755   7.746   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.470   7.914   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.651   9.001   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.315  10.503   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       9.120   8.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   39                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    6   14   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
CONECT   24   14   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   24   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36    5   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₄O₁₁

Average Mass

594.6130 Da

Monoisotopic Mass

594.21011 Da

IUPAC Name

(8S,9S,10S,11R)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate

Traditional Name

(8S,9S,10S,11R)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(OC)=C1OC)C1=C(C=C3OCOC3=C1OC)[C@H](OC(=O)C1=CC=CC=C1)[C@H](C)[C@](C)(O)[C@H]2OC(C)=O

InChI Identifier

InChI=1S/C32H34O11/c1-16-25(43-31(34)18-11-9-8-10-12-18)19-13-22-27(41-15-40-22)29(39-7)23(19)24-20(30(32(16,3)35)42-17(2)33)14-21(36-4)26(37-5)28(24)38-6/h8-14,16,25,30,35H,15H2,1-7H3/t16-,25+,30-,32-/m0/s1

InChI Key

UJJWRJWLPZAYGS-MLDYHGJLSA-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

Species Name	Source	Reference
Kadsura heteroclita	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Dibenzocyclooctane lignan
Benzoate ester
Benzodioxole
Benzoic acid or derivatives
Anisole
Benzoyl
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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
logP	4.15	ChemAxon
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	128.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	152.67 m³·mol⁻¹	ChemAxon
Polarizability	60.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154723703

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang W, Liu J, Liu R, Xu Z, Yang M, Wang W, Liu P, Sabia G, Wang X, Guo D: Four new lignans from the stems of Kadsura heteroclita. Planta Med. 2006 Feb;72(3):284-8. doi: 10.1055/s-2005-916213. [PubMed:16534740 ]
LOTUS database [Link]

Showing NP-Card for (8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate (NP0198750)

MOL for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

3D MOL for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

3D SDF for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

3D-SDF for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

PDB for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

3D PDB for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

SMILES for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

INCHI for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

Structure for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)

3D Structure for NP0198750 ((8s,9s,10s,11r)-8-(acetyloxy)-9-hydroxy-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(12),2(7),3,5,13,18-hexaen-11-yl benzoate)