NP-MRD: Showing NP-Card for methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate (NP0326707)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 08:32:46 UTC

Updated at

2022-09-12 08:32:47 UTC

NP-MRD ID

NP0326707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

Description

Methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]Nonadeca-3(8),4,6-triene-19-carboxylate belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate is found in Alstonia macrophylla. Methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]Nonadeca-3(8),4,6-triene-19-carboxylate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507092D          

 43 49  0  0  0  0            999 V2000
    0.4266   -1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149   -1.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694   -0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356   -1.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    0.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3134   -1.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7113   -0.7040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536   -2.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2248   -3.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093   -3.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1804   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6114   -3.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826   -4.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693   -5.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269   -3.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -3.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -3.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558   -2.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4584   -0.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5605    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0021    1.6148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098    1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    0.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983   -0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427    1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982    0.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6310    0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938    0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3795   -0.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2024   -0.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2768    0.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139    1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911    1.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960    2.1024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    1.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322    2.2240    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 10 21  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 24 42  1  0  0  0  0
 32 42  1  0  0  0  0
 42 43  1  0  0  0  0
 30 43  1  0  0  0  0
M  END

     RDKit          3D

 79 85  0  0  0  0  0  0  0  0999 V2000
   -1.7213   -3.3633   -3.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -3.7882   -2.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1033   -3.2315   -1.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -3.7330   -0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3562   -3.1857    0.8893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600   -2.2186    1.4767 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5721   -1.0915    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2146   -0.5645    0.2151 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0574    0.8727    0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7530    1.9919    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4079    3.2462    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213    4.3726    0.3761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7994    5.6402    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3646    3.3881    1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6710    2.2607    2.0158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138    1.0052    1.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4476   -0.3045    1.7362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4136   -1.2079    1.3040 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4021   -1.4802    2.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0294   -2.6169    0.9678 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2327   -2.6430   -0.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1221   -2.1429   -1.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6873   -0.7958   -1.1816 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6060    0.2534   -1.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5454    0.1203   -0.7338 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346    0.9708   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886    1.8933   -1.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8610    0.8666   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201    1.8511   -0.2633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0246    1.8517    0.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0046    2.8134    0.2297 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7085    3.8694   -0.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2918    0.8153    1.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5037    0.8001    1.9575 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7176    1.4212    3.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -0.1815    1.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6795   -1.1822    2.3976 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8200   -2.2564    2.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -0.1261    0.8119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7899   -0.5026   -2.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052    0.6043   -2.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8414   -1.3350   -2.4400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8506   -0.9743   -3.3530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1827   -2.4240   -4.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9047   -4.0866   -4.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6177   -3.3113   -3.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -4.6120   -2.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6552   -4.8569   -0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683   -3.5903   -0.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1380   -2.6147    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2314   -0.3871    1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1201   -1.5811   -0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5863    1.9905   -0.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7110    5.8431    0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3114    6.4297    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0315    5.7730    1.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    4.3802    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1585    2.3499    2.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4871   -0.5107    2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4505   -3.0283    1.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6831   -2.0917   -0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -3.7176   -0.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4230   -2.0604   -2.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0018    1.2840   -1.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3733    0.2218   -2.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    2.6782   -0.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7445    4.3185   -0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5323    3.3424   -1.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5137    4.6106   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9254    2.5116    3.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8827    1.2955    3.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6494    0.9862    3.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884   -1.8419    2.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680   -2.6398    3.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8834   -3.0920    1.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4654   -0.9024    0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7916   -1.5996   -4.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768    0.0726   -3.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8518   -1.1224   -2.9150 H   0  0  0  0  0  0  0  0  0  0  0  0
 43 42  1  0
 42 40  1  0
 40 41  2  0
 23 40  1  6
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  1  0
 37 38  1  0
 36 39  2  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 18 17  1  1
 18 19  1  0
  8 23  1  0
 18  8  1  0
 39 28  1  0
  3 22  1  0
 19  6  1  0
 18 20  1  0
 16  9  1  0
 43 77  1  0
 43 78  1  0
 43 79  1  0
 24 64  1  0
 24 65  1  0
 29 66  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 38 73  1  0
 38 74  1  0
 38 75  1  0
 39 76  1  0
 22 63  1  6
 21 61  1  0
 21 62  1  0
 20 60  1  1
  4 48  1  0
  4 49  1  0
  2 47  1  0
  1 44  1  0
  1 45  1  0
  1 46  1  0
  6 50  1  1
  7 51  1  0
  7 52  1  0
 10 53  1  0
 13 54  1  0
 13 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 17 59  1  0
M  END


  Mrv1533004161507092D          

 43 49  0  0  0  0            999 V2000
    0.4266   -1.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5149   -1.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2694   -0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9356   -1.2450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3578    0.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1423   -0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3134   -1.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7113   -0.7040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -2.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0536   -2.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2248   -3.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093   -3.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1804   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6114   -3.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826   -4.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1693   -5.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8269   -3.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -3.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4291   -3.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558   -2.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4584   -0.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5605    0.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5754    1.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0021    1.6148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7098    1.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280    0.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983   -0.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    1.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427    1.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982    0.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6310    0.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0938    0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    0.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3795   -0.5604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2024   -0.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2768    0.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139    1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911    1.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3960    2.1024    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    1.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0322    2.2240    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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
 10 21  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 24 42  1  0  0  0  0
 32 42  1  0  0  0  0
 42 43  1  0  0  0  0
 30 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(COC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C2CC3N(C\C2=C\C)C2CC11C4=CC(OC)=CC=C4NC31O2

> <INCHI_IDENTIFIER>
InChI=1S/C32H36N2O9/c1-7-17-15-34-25-13-20(17)30(29(36)41-6,16-42-28(35)18-10-23(38-3)27(40-5)24(11-18)39-4)31-14-26(34)43-32(25,31)33-22-9-8-19(37-2)12-21(22)31/h7-12,20,25-26,33H,13-16H2,1-6H3/b17-7-

> <INCHI_KEY>
JIBNKPQBEIZZCU-IDUWFGFVSA-N

> <FORMULA>
C32H36N2O9

> <MOLECULAR_WEIGHT>
592.645

> <EXACT_MASS>
592.242080747

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
60.85111645259123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.4921289293333326

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.093689761957286

> <JCHEM_PKA_STRONGEST_BASIC>
4.664694996340211

> <JCHEM_POLAR_SURFACE_AREA>
114.02000000000001

> <JCHEM_REFRACTIVITY>
156.24899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.796  -3.570   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.961  -2.039   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.370  -1.416   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.613  -2.324   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.534   0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.999  -0.361   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.318  -1.868   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.783  -2.344   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.928  -1.314   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.102  -3.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.567  -4.327   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.886  -5.834   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.351  -6.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.670  -7.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.741  -6.864   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.061  -8.370   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.916  -9.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.277  -6.387   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.132  -7.417   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.668  -6.941   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.957  -4.881   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.856  -0.053   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.046   1.071   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.074   2.578   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       0.004   3.014   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -1.325   1.990   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.799   0.421   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.863  -0.692   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.432  -2.170   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.931   2.365   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.813   2.771   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.357   1.545   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.911   1.393   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.775   0.118   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.311   0.229   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.175  -1.046   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.711  -0.935   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.983   1.614   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.119   2.889   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.583   2.778   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       4.472   3.925   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       2.883   3.276   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.927   4.152   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22   32                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   10                                                       
CONECT   22    5   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   42                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31   43                                                  
CONECT   31   30   32                                                       
CONECT   32   31    5   33   42                                             
CONECT   33   32   34   40                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   33   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   24   32   43                                             
CONECT   43   42   30                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Value	Source
Methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1,.0,.0,.0,]nonadeca-3(8),4,6-triene-19-carboxylic acid	Generator
Methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3(8),4,6-triene-19-carboxylic acid	Generator

Chemical Formula

C₃₂H₃₆N₂O₉

Average Mass

592.6450 Da

Monoisotopic Mass

592.24208 Da

IUPAC Name

methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

Traditional Name

methyl (14E)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(COC(=O)C2=CC(OC)=C(OC)C(OC)=C2)C2CC3N(C\C2=C\C)C2CC11C4=CC(OC)=CC=C4NC31O2

InChI Identifier

InChI=1S/C32H36N2O9/c1-7-17-15-34-25-13-20(17)30(29(36)41-6,16-42-28(35)18-10-23(38-3)27(40-5)24(11-18)39-4)31-14-26(34)43-32(25,31)33-22-9-8-19(37-2)12-21(22)31/h7-12,20,25-26,33H,13-16H2,1-6H3/b17-7-

InChI Key

JIBNKPQBEIZZCU-IDUWFGFVSA-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
Alstonia macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Pyridoindole
Carbazole
Beta-carboline
Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
P-methoxybenzoic acid or derivatives
Benzoate ester
Quinolizidine
Benzoic acid or derivatives
Indole or derivatives
Dihydroindole
Anisole
Methoxybenzene
Benzoyl
Phenoxy compound
Phenol ether
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Piperidine
Oxazolidine
Tetrahydrofuran
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Hemiaminal
Organoheterocyclic compound
Azacycle
Oxacycle
Ether
Secondary amine
Carboxylic acid derivative
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
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	3.18	ALOGPS
logP	3.49	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	4.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.02 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	156.25 m³·mol⁻¹	ChemAxon
Polarizability	60.85 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

56678277

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate (NP0326707)

MOL for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D MOL for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D SDF for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D-SDF for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

PDB for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D PDB for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

SMILES for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

INCHI for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

Structure for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D Structure for NP0326707 (methyl (14e)-14-ethylidene-6-methoxy-19-[(3,4,5-trimethoxybenzoyloxy)methyl]-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)