NP-MRD: Showing NP-Card for methyl (1r,4s,7s,14r,20r,21s,24e,25s,26s,38s,39s)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1³,¹⁵.1⁴,⁷.1⁷,¹¹.1²¹,²⁵.0¹,²⁰.0⁴,¹⁴.0²⁰,²⁷.0²⁸,³³.0¹⁴,³⁸.0¹⁹,³⁷]nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate (NP0260633)

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Record Information

Version

2.0

Created at

2022-09-08 02:51:32 UTC

Updated at

2022-09-08 02:51:32 UTC

NP-MRD ID

NP0260633

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,4s,7s,14r,20r,21s,24e,25s,26s,38s,39s)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1³,¹⁵.1⁴,⁷.1⁷,¹¹.1²¹,²⁵.0¹,²⁰.0⁴,¹⁴.0²⁰,²⁷.0²⁸,³³.0¹⁴,³⁸.0¹⁹,³⁷]nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate

Description

Methyl (1R,4S,7S,14R,20R,21S,24E,25S,26S,38S,39S)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1³,¹⁵.1⁴,⁷.1⁷,¹¹.1²¹,²⁵.0¹,²⁰.0⁴,¹⁴.0²⁰,²⁷.0²⁸,³³.0¹⁴,³⁸.0¹⁹,³⁷]Nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate belongs to the class of organic compounds known as pleiocarpaman alkaloids. These are alkaloids with a structure that is based on the pleiocarpaman skeleton. These alkaloids arise from the cyclization of a corynantheine precursor via C-16 to N-1. methyl (1r,4s,7s,14r,20r,21s,24e,25s,26s,38s,39s)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1³,¹⁵.1⁴,⁷.1⁷,¹¹.1²¹,²⁵.0¹,²⁰.0⁴,¹⁴.0²⁰,²⁷.0²⁸,³³.0¹⁴,³⁸.0¹⁹,³⁷]nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate is found in Hunteria congolana. Based on a literature review very few articles have been published on methyl (1R,4S,7S,14R,20R,21S,24E,25S,26S,38S,39S)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1³,¹⁵.1⁴,⁷.1⁷,¹¹.1²¹,²⁵.0¹,²⁰.0⁴,¹⁴.0²⁰,²⁷.0²⁸,³³.0¹⁴,³⁸.0¹⁹,³⁷]Nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204512D          

 46 57  0  0  1  0            999 V2000
   -3.5569   -4.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4770   -4.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945   -3.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2440   -3.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086   -2.8136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1231   -2.4523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9389   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333   -2.8519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257   -3.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8350   -4.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -5.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996   -5.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2944   -4.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247   -3.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1850   -3.2572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7974   -3.5002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1389   -4.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241   -4.3324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8629   -3.5133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7647   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6933   -2.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -3.5097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2227   -3.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0566   -3.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -2.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9751   -1.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968   -0.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100   -0.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4016   -1.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -3.6908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4986   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -4.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7824   -4.4092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -4.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -3.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5105   -2.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223   -2.9013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8838   -2.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594   -1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4015   -2.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7888   -2.3297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3544   -1.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3665   -3.6719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  1  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
  8 32  1  6  0  0  0
 33 12  1  1  0  0  0
 33 34  1  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
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 10  1  6  0  0  0
 33 43  1  0  0  0  0
 43 44  1  0  0  0  0
 40 44  1  0  0  0  0
 44 45  1  1  0  0  0
 40 46  1  0  0  0  0
 46 36  1  6  0  0  0
 33 46  1  0  0  0  0
M  END

     RDKit          3D

 92103  0  0  0  0  0  0  0  0999 V2000
    6.4059    0.9605   -3.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7284    1.6982   -2.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5987    1.4035   -1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995    2.2520   -0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133    2.1560   -0.2720 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086    2.4284    1.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1371    1.1733    1.9116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    0.2719    1.2937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2729    0.8614    1.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107    0.4053    0.6238 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9202   -0.5717   -0.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403   -1.2410   -0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204   -2.2451   -1.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -2.5285   -2.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -1.8293   -1.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720   -0.8236   -0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    0.0022   -0.1191 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8231    1.2138   -0.9191 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4786    0.7065   -2.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8787    0.1673   -1.8178 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7557   -0.8661   -0.7758 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0115   -1.0026    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1575   -0.9289   -0.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732   -1.2167    1.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1620   -1.3434    2.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -0.8917    0.0340 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149   -1.7138    1.1352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795   -2.9963    1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0624   -3.5988    2.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1493   -2.9169    3.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518   -1.6508    3.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -1.0594    1.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300   -0.6633   -0.1419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8535   -1.5828    0.8485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3376   -1.7188    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5446   -0.8984   -0.6356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7552   -0.2842   -0.8874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8019    1.1105   -1.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4693    1.8065   -1.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5264    1.2264   -0.6142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8122    1.3813    0.8588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4727    1.1581    1.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6694    0.6264    0.4140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0828    1.6382   -0.6339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4097    1.6156   -1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3436   -0.2513   -1.0054 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9277    0.1587   -3.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7168    1.7130   -3.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4168    0.6464   -2.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2043    2.6343   -1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3280    3.3273   -0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    1.9867    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9962    3.0701    1.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2881    3.0288    1.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    1.4505    2.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    0.6771    1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333    1.9430    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    0.4988    2.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6770   -2.7851   -2.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3392   -3.3256   -2.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512   -2.1159   -1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731    1.7164   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6347    1.5873   -2.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9024   -0.0145   -2.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2091   -0.2599   -2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7631   -1.8636   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9053   -1.8834    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5915   -0.3464    2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9952   -1.9525    3.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957   -3.5347    0.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3475   -4.5937    2.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7161   -3.3568    4.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0181   -1.0929    3.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6994   -1.3623    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5327   -2.7896    0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9941   -1.5697    1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3230   -0.9100   -1.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4116   -0.3690    0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4111    1.7635   -0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3307    1.2333   -2.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1308    1.6767   -2.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6160    2.9111   -1.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1224    2.4610    0.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0570    2.1562    1.8159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0194    2.6742   -0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550    1.0133   -2.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3660    1.2735   -1.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389    2.6479   -2.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2180   -0.3330   -2.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 17 16  1  6
 17 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
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 31 32  2  0
 12 33  1  0
 33 34  1  1
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 40 39  1  6
 40 41  1  0
 41 42  1  0
 43 42  1  1
 43 44  1  0
 44 45  1  0
 40 46  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 26 21  1  0
 32 27  1  0
 43 33  1  0
  3 20  1  0
 17 18  1  0
 46 33  1  0
 17  8  1  0
 46 36  1  0
 32  8  1  0
 44 40  1  0
 43 10  1  0
 16 11  1  0
 25 67  1  0
 25 68  1  0
 25 69  1  0
 21 66  1  6
 20 65  1  6
 19 63  1  0
 19 64  1  0
 18 62  1  6
  6 53  1  0
  6 54  1  0
  7 55  1  0
  7 56  1  0
  9 57  1  0
  9 58  1  0
 13 59  1  0
 14 60  1  0
 15 61  1  0
 28 70  1  0
 29 71  1  0
 30 72  1  0
 31 73  1  0
 34 74  1  0
 34 75  1  0
 35 76  1  0
 35 77  1  0
 37 78  1  0
 37 79  1  0
 38 80  1  0
 38 81  1  0
 39 82  1  0
 39 83  1  0
 41 84  1  0
 41 85  1  0
 42 86  1  0
 42 87  1  0
 44 88  1  1
 45 89  1  0
 45 90  1  0
 45 91  1  0
 46 92  1  6
  4 51  1  0
  4 52  1  0
  2 50  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
M  END


  Mrv1652309082204512D          

 46 57  0  0  1  0            999 V2000
   -3.5569   -4.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4770   -4.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945   -3.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2440   -3.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5086   -2.8136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -1.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762   -1.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1231   -2.4523    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9389   -2.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5333   -2.8519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2257   -3.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8350   -4.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -5.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8996   -5.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2944   -4.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247   -3.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1850   -3.2572    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7974   -3.5002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1389   -4.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241   -4.3324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8629   -3.5133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7647   -3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6933   -2.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -3.5097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2227   -3.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0566   -3.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -2.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9751   -1.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968   -0.9560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0100   -0.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4016   -1.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5800   -2.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -3.6908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4986   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1875   -4.9929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7824   -4.4092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -4.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010   -3.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5105   -2.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6223   -2.9013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8838   -2.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0594   -1.8885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4015   -2.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7888   -2.3297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3544   -1.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3665   -3.6719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  1  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
  8 32  1  6  0  0  0
 33 12  1  1  0  0  0
 33 34  1  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
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 10  1  6  0  0  0
 33 43  1  0  0  0  0
 43 44  1  0  0  0  0
 40 44  1  0  0  0  0
 44 45  1  1  0  0  0
 40 46  1  0  0  0  0
 46 36  1  6  0  0  0
 33 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260633

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@@]45CN6C7=C(C=CC=C7[C@@]34N1C1=CC=CC=C51)[C@@]13CCN4CCC[C@@]5(CC[C@@]61[C@H]5C)[C@@H]34)C\C2=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C40H46N4O2/c1-4-25-22-42-19-16-37-23-43-33-28(38-17-20-41-18-8-13-36(35(38)41)14-15-39(38,43)24(36)2)10-7-11-29(33)40(37)31(42)21-26(25)32(34(45)46-3)44(40)30-12-6-5-9-27(30)37/h4-7,9-12,24,26,31-32,35H,8,13-23H2,1-3H3/b25-4-/t24-,26-,31-,32-,35-,36-,37-,38+,39-,40+/m0/s1

> <INCHI_KEY>
NHYWHOQGRJLYBG-HKIMRKGLSA-N

> <FORMULA>
C40H46N4O2

> <MOLECULAR_WEIGHT>
614.834

> <EXACT_MASS>
614.362076737

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
70.2872972941717

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,4S,7S,14R,20R,21S,24E,25S,26S,38S,39S)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1^{3,15}.1^{4,7}.1^{7,11}.1^{21,25}.0^{1,20}.0^{4,14}.0^{20,27}.0^{28,33}.0^{14,38}.0^{19,37}]nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate

> <JCHEM_LOGP>
5.374299104666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.400239239582884

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
181.26389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4S,7S,14R,20R,21S,24E,25S,26S,38S,39S)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1^{3,15}.1^{4,7}.1^{7,11}.1^{21,25}.0^{1,20}.0^{4,14}.0^{20,27}.0^{28,33}.0^{14,38}.0^{19,37}]nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.640  -9.288   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.490  -7.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.843  -7.152   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.189  -5.675   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.816  -5.252   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.159  -3.491   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.516  -3.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.230  -4.578   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.753  -4.247   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.862  -5.324   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.288  -6.792   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.425  -7.762   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.096  -9.342   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.679  -9.917   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.550  -8.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.793  -7.265   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.345  -6.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.489  -6.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.126  -8.157   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.592  -8.087   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.477  -6.558   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.161  -5.923   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.027  -4.195   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.656  -6.551   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.882  -5.620   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -1.972  -5.680   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -2.551  -4.328   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.687  -3.288   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.354  -1.785   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.885  -1.321   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.750  -2.361   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.083  -3.865   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.770  -6.890   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.664  -8.505   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.950  -9.320   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       7.060  -8.231   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       8.619  -8.124   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.335  -6.751   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.420  -5.481   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.762  -5.416   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.250  -4.018   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.711  -3.525   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.483  -5.200   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.206  -4.349   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.395  -2.834   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.284  -6.854   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17   32                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   43                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    8   18   26                                             
CONECT   18   17    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   21   17   27                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   27    8                                                  
CONECT   33   12   34   43   46                                             
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   46                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   44   46                                             
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   10   33   44                                             
CONECT   44   43   40   45                                                  
CONECT   45   44                                                            
CONECT   46   40   36   33                                                  
MASTER        0    0    0    0    0    0    0    0   46    0  114    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,4S,7S,14R,20R,21S,24E,25S,26S,38S,39S)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1,.1,.1,.1,.0,.0,.0,.0,.0,.0,]nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylic acid	Generator

Chemical Formula

C₄₀H₄₆N₄O₂

Average Mass

614.8340 Da

Monoisotopic Mass

614.36208 Da

IUPAC Name

methyl (1R,4S,7S,14R,20R,21S,24E,25S,26S,38S,39S)-24-ethylidene-39-methyl-3,11,22,27-tetraazadodecacyclo[20.11.2.1^{3,15}.1^{4,7}.1^{7,11}.1^{21,25}.0^{1,20}.0^{4,14}.0^{20,27}.0^{28,33}.0^{14,38}.0^{19,37}]nonatriaconta-15(37),16,18,28,30,32-hexaene-26-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1[C@H]2C[C@@H]3N(CC[C@@]45CN6C7=C(C=CC=C7[C@@]34N1C1=CC=CC=C51)[C@@]13CCN4CCC[C@@]5(CC[C@@]61[C@H]5C)[C@@H]34)C\C2=C\C

InChI Identifier

InChI=1S/C40H46N4O2/c1-4-25-22-42-19-16-37-23-43-33-28(38-17-20-41-18-8-13-36(35(38)41)14-15-39(38,43)24(36)2)10-7-11-29(33)40(37)31(42)21-26(25)32(34(45)46-3)44(40)30-12-6-5-9-27(30)37/h4-7,9-12,24,26,31-32,35H,8,13-23H2,1-3H3/b25-4-/t24-,26-,31-,32-,35-,36-,37-,38+,39-,40+/m0/s1

InChI Key

NHYWHOQGRJLYBG-HKIMRKGLSA-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
Hunteria congolana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pleiocarpaman alkaloids. These are alkaloids with a structure that is based on the pleiocarpaman skeleton. These alkaloids arise from the cyclization of a corynantheine precursor via C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Pleiocarpaman alkaloids

Sub Class

Not Available

Direct Parent

Pleiocarpaman alkaloids

Alternative Parents

Substituents

Pleiocarpaman skeleton
Aspidosperma alkaloid
Neolignan skeleton
Indolo[3,2-1de][1,5]naphthyridine
Alpha-amino acid ester
Beta-carboline
Carbazole
Pyridoindole
2,3-cyclopentanoindoline
Aminoquinoline
4-aminoquinoline
Naphthyridine
Aromatic monoterpenoid
Alpha-amino acid or derivatives
Monoterpenoid
Diazanaphthalene
Quinolizidine
Tetrahydroquinoline
Norbornane monoterpenoid
Quinolidine
Azaspirodecane
Indole or derivatives
Piperidinecarboxylic acid
Indolizidine
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Methyl ester
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid ester
Amino acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organopnictogen compound
Amine
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	5.37	ChemAxon
pKa (Strongest Basic)	10.4	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	181.26 m³·mol⁻¹	ChemAxon
Polarizability	70.29 Å³	ChemAxon
Number of Rings	12	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	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

163189030

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]