NP-MRD: Showing NP-Card for (1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate (NP0178938)

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Record Information

Version

2.0

Created at

2022-09-03 17:02:05 UTC

Updated at

2022-09-03 17:02:05 UTC

NP-MRD ID

NP0178938

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate

Description

Merckonine belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. (1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate is found in Aconitum napellus. Based on a literature review very few articles have been published on Merckonine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032219022D          

 44 50  0  0  1  0            999 V2000
   -0.1287   -3.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942   -3.2915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637   -2.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8924   -1.6519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8114   -0.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    0.1357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -0.2772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8126   -0.2766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8678   -0.6751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0234   -0.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456    0.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7699   -1.6440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2504   -1.2684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3719   -0.8139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1623    0.3105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4852   -1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -0.8478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5383   -0.3778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0451   -1.8221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7458   -2.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904   -1.9394    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4154   -2.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -1.1497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9892   -1.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4340   -0.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5669   -0.4739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0823    0.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   -0.5533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7903    0.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3579    1.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330    1.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631    1.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -1.3694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.1351   -3.0521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6397   -3.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4614   -3.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2928   -4.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7677   -5.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208   -5.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5991   -6.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -5.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711   -4.5914    0.0000 C   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12  9  1  6  0  0  0
  4 12  1  0  0  0  0
 13 12  1  6  0  0  0
  7 13  1  0  0  0  0
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 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  0  0  0  0
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 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 20  1  1  0  0  0
 34 35  1  0  0  0  0
 22 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 39 44  1  0  0  0  0
M  END

     RDKit          3D

 85 91  0  0  0  0  0  0  0  0999 V2000
   -5.2729    1.9357    2.2966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4628    1.8914    1.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6073    0.5675    0.6552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7784    0.3917   -0.5749 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8725   -0.9805   -1.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8812   -1.5462   -1.7204 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -1.0742   -1.6937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9203   -1.4927   -0.4024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8927   -0.7158    0.5412 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8995   -1.6523    0.7512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505   -2.1628    2.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5362    0.4160   -1.5560 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1177    1.1155   -2.7219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7054    0.2454   -3.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1650    0.3790   -4.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1259    2.1487   -2.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2477    1.4520   -1.5405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1781    0.9503   -2.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2018    1.0420   -1.2848 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8192    0.8129   -2.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.6903   -1.6095 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1450    1.4398   -2.1533 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6799   -0.7593   -0.6210 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301   -1.1922   -1.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5152   -1.6532   -0.9395 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9820   -2.3704   -2.0350 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570   -1.0359   -0.0739 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7592   -1.4179    1.2576 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8060   -2.6884    1.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -3.0118    3.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5659   -3.6342    0.9796 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4502    0.4608   -0.0541 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7945    1.1154   -0.1754 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7395    0.7192    0.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.6521    1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0825    2.8545    1.3744 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075    1.2575    2.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7848   -0.0444    2.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7461   -0.3817    3.7184 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3439    0.6097    4.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9799    1.9291    4.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204    2.2298    3.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2934    1.6311    1.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0728    1.4489    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3537    1.6843   -3.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    0.1520   -4.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204   -0.2320   -5.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    1.4364   -5.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5712    2.8059   -1.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862    2.7682   -3.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7821    2.2296   -0.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7861   -3.9320    3.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979   -2.2147    3.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6171    2.2073   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197   -0.8229    2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0393   -1.4154    3.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0863    0.3154    5.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4682    2.6674    4.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452    3.2704    3.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  2  0
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  7  8  1  0
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 18 64  1  1
 19 65  1  0
 16 59  1  0
 16 60  1  0
 16 61  1  0
M  END


  Mrv1652309032219022D          

 44 50  0  0  1  0            999 V2000
   -0.1287   -3.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6942   -3.2915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0637   -2.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8924   -1.6519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8114   -0.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    0.1357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -0.2772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8126   -0.2766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8678   -0.6751    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0234   -0.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456    0.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7699   -1.6440    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2504   -1.2684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3719   -0.8139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1623    0.3105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3998    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4852   -1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2990   -0.8478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5383   -0.3778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0451   -1.8221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7458   -2.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6904   -1.9394    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4154   -2.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -1.1497    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9892   -1.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4340   -0.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5669   -0.4739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0823    0.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7045   -0.5533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7903    0.3672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3579    1.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330    1.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631    1.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -1.3694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1909   -2.1596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1351   -3.0521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6397   -3.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4614   -3.6951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2928   -4.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7677   -5.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4208   -5.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5991   -6.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1243   -5.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4711   -4.5914    0.0000 C   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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  6  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 12  9  1  6  0  0  0
  4 12  1  0  0  0  0
 13 12  1  6  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  1  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 20  1  1  0  0  0
 34 35  1  0  0  0  0
 22 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 39 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178938

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@]12C=N[C@@H]3[C@@H]4[C@H](OC)[C@H]1[C@]3([C@@H]1C[C@@]3(O)[C@H](OC(=O)C5=CC=CC=C5)[C@@H]1[C@]4(OC(C)=O)[C@@H](O)[C@@H]3OC)[C@H](C[C@H]2O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H41NO11/c1-15(34)44-32-20-17(12-30(38,27(42-5)25(32)36)26(20)43-28(37)16-9-7-6-8-10-16)31-19(40-3)11-18(35)29(14-39-2)13-33-24(31)21(32)22(41-4)23(29)31/h6-10,13,17-27,35-36,38H,11-12,14H2,1-5H3/t17-,18-,19+,20-,21+,22+,23-,24-,25+,26-,27+,29+,30-,31+,32-/m1/s1

> <INCHI_KEY>
DGRGGRMNHAAVMN-BMTFSNIDSA-N

> <FORMULA>
C32H41NO11

> <MOLECULAR_WEIGHT>
615.676

> <EXACT_MASS>
615.267961144

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
63.43639024249186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4R,5R,6S,7S,8R,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadec-11-en-4-yl benzoate

> <JCHEM_LOGP>
-1.0585897936666653

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.22756514474927

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.532479397845929

> <JCHEM_PKA_STRONGEST_BASIC>
5.845111920808846

> <JCHEM_POLAR_SURFACE_AREA>
162.57

> <JCHEM_REFRACTIVITY>
151.3001999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4R,5R,6S,7S,8R,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadec-11-en-4-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.240  -6.255   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.296  -6.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.986  -4.722   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.666  -3.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.515  -1.300   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.088   0.253   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.045  -0.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.250  -0.516   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.487  -1.260   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.910  -0.213   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.952   1.677   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.304  -3.069   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.201  -2.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.561  -1.519   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.170   0.580   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.746   1.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.906  -2.649   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.558  -1.582   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.005  -0.705   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.684  -3.401   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.992  -4.611   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.755  -3.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.109  -4.510   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.518  -2.146   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.180  -1.983   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.010  -0.634   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.525  -0.885   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.487   0.440   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.915  -1.033   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.075   0.685   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.268   2.051   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.728   2.035   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.024   3.393   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.792  -2.556   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.823  -4.031   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.719  -5.697   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.661  -7.035   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.195  -6.898   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.013  -8.433   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.900  -9.692   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.252 -11.089   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.718 -11.227   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.832  -9.968   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.479  -8.571   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12   18                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    4   13                                                  
CONECT   13   12    7   14   20                                             
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18                                                       
CONECT   18   17    4   19                                                  
CONECT   19   18                                                            
CONECT   20   13   21   34                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   35                                             
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    8   30   34                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   20   35                                                  
CONECT   35   34   22   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₁NO₁₁

Average Mass

615.6760 Da

Monoisotopic Mass

615.26796 Da

IUPAC Name

(1S,2R,3R,4R,5R,6S,7S,8R,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadec-11-en-4-yl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC[C@]12C=N[C@@H]3[C@@H]4[C@H](OC)[C@H]1[C@]3([C@@H]1C[C@@]3(O)[C@H](OC(=O)C5=CC=CC=C5)[C@@H]1[C@]4(OC(C)=O)[C@@H](O)[C@@H]3OC)[C@H](C[C@H]2O)OC

InChI Identifier

InChI=1S/C32H41NO11/c1-15(34)44-32-20-17(12-30(38,27(42-5)25(32)36)26(20)43-28(37)16-9-7-6-8-10-16)31-19(40-3)11-18(35)29(14-39-2)13-33-24(31)21(32)22(41-4)23(29)31/h6-10,13,17-27,35-36,38H,11-12,14H2,1-5H3/t17-,18-,19+,20-,21+,22+,23-,24-,25+,26-,27+,29+,30-,31+,32-/m1/s1

InChI Key

DGRGGRMNHAAVMN-BMTFSNIDSA-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
Aconitum napellus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Azepine
Tetrahydropyridine
Dicarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Azacycle
Ether
Polyol
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Imine
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Alcohol
Organic oxide
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	-1.1	ChemAxon
pKa (Strongest Acidic)	12.53	ChemAxon
pKa (Strongest Basic)	5.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	162.57 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	151.3 m³·mol⁻¹	ChemAxon
Polarizability	63.44 Å³	ChemAxon
Number of Rings	7	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

101945916

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate (NP0178938)

MOL for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

3D MOL for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

3D SDF for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

3D-SDF for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

PDB for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

3D PDB for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

SMILES for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

INCHI for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

Structure for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)

3D Structure for NP0178938 ((1s,2r,3r,4r,5r,6s,7s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-5,7,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadec-11-en-4-yl benzoate)