NP-MRD: Showing NP-Card for (1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate (NP0208365)

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Record Information

Version

2.0

Created at

2022-09-05 05:20:31 UTC

Updated at

2022-09-05 05:20:31 UTC

NP-MRD ID

NP0208365

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate

Description

Methyl (1R,9S,10S,12S,13Z,15S,16S,17R,18S)-18-(acetyloxy)-13-ethylidene-8-methyl-15-oxo-8,15λ⁵-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6-triene-17-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. (1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate is found in Alstonia macrophylla. Based on a literature review very few articles have been published on methyl (1R,9S,10S,12S,13Z,15S,16S,17R,18S)-18-(acetyloxy)-13-ethylidene-8-methyl-15-oxo-8,15λ⁵-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]Nonadeca-2,4,6-triene-17-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207202D          

 31 36  0  0  1  0            999 V2000
   -1.4562   -0.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6264   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032    0.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    0.7507    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    0.5496   -0.1826    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.5603   -0.0062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1025   -0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.1224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7195    0.7631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1696    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0851   -0.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -0.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117   -1.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    1.2630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9206    2.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442    2.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    3.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577    3.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0788    1.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    1.5104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4921    0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0451    0.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1054    0.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -0.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7457   -0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -0.8415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -1.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3739   -0.2955    0.0000 C   0  0  2  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  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  8  1  1  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  1  0  0  0
 10 22  1  0  0  0  0
  5 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 29  1  6  0  0  0
  7 31  1  0  0  0  0
 20 31  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END

     RDKit          3D

 59 64  0  0  0  0  0  0  0  0999 V2000
    5.1919    1.1817   -0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0011    0.6731   -0.7921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8143    0.9237   -0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    1.6757    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340    1.4944    1.2568 N   0  0  1  0  0  4  0  0  0  0  0  0
    0.8515    2.1834    2.3807 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.3046    2.0837    0.1912 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7270    1.6598   -1.1756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6118    0.4218   -0.9940 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9046   -0.5046   -0.0205 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6592   -1.7719   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082   -2.8419   -0.3533 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929   -1.7979    0.3149 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7698   -2.9856    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5299   -0.6443   -0.4232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9030   -2.0011   -0.1796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5064   -2.7765   -1.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -4.1799   -0.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6745   -2.1748   -2.2806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    0.1687    0.6170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5245   -0.2255    1.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9049    0.0904    1.3954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6891    0.0229    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214   -0.8991    1.0323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9727   -0.7349    0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4477    0.3927    0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5603    1.3463   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1986    1.1597   -0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1153    2.0056   -0.4012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0851    3.0060   -1.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0680    1.6508    0.4792 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3531    0.5454    0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625    2.2328    0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0672    1.1501   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369    0.1127   -1.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135    2.7524    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0895    1.2398    1.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3813    3.1812    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922    2.4858   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719    1.5131   -1.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8187   -0.0987   -1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907   -3.6822   -0.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8498   -2.7585    0.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6585   -3.4696    1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -0.3409   -1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003   -4.3100   -0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4245   -4.5502   -0.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5421   -4.8550   -1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5439   -1.3061    2.0764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7914    0.3995    2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -0.3490    2.0337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563   -1.7854    1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7143   -1.4562    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5045    0.5458    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9737    2.2153   -0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1596    2.5489   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9100    3.7562   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    3.6035   -1.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416    2.0768    1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 10 11  1  1
 10 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22  5  1  0
  5  6  1  1
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  3  9  1  0
  9  8  1  0
  8  7  1  0
  7 31  1  0
 31 29  1  0
 29 30  1  0
 29 28  1  0
 28 27  2  0
 27 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 22 10  1  0
  7  5  1  0
 23 28  1  0
  9 10  1  0
 31 20  1  0
 20 23  1  1
 14 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  6
 18 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  1
  4 36  1  0
  4 37  1  0
  2 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  9 41  1  6
  8 39  1  0
  8 40  1  0
  7 38  1  6
 31 59  1  1
 30 56  1  0
 30 57  1  0
 30 58  1  0
 27 55  1  0
 26 54  1  0
 25 53  1  0
 24 52  1  0
M  CHG  2   5   1   6  -1
M  END


  Mrv1652309052207202D          

 31 36  0  0  1  0            999 V2000
   -1.4562   -0.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6264   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032    0.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    0.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    0.7507    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    0.5496   -0.1826    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.5603   -0.0062    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1025   -0.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.1224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7195    0.7631    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1696    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0851   -0.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -0.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117   -1.3547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914    1.2630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9206    2.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442    2.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9598    3.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3577    3.5184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449    0.5168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0788    1.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029    1.5104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4921    0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0451    0.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    0.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1054    0.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -0.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7457   -0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -0.8415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1674   -1.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3739   -0.2955    0.0000 C   0  0  2  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  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  8  1  1  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  1  0  0  0
 10 22  1  0  0  0  0
  5 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 29  1  6  0  0  0
  7 31  1  0  0  0  0
 20 31  1  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
> <DATABASE_ID>
NP0208365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12[C@@H](OC(C)=O)[C@@]34C[C@@H]1[N@@+]1([O-])C\C(=C/C)[C@@H]2C[C@H]1[C@H]3N(C)C1=CC=CC=C41

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O5/c1-5-14-12-26(29)18-10-16(14)24(22(28)30-4)19(26)11-23(21(24)31-13(2)27)15-8-6-7-9-17(15)25(3)20(18)23/h5-9,16,18-21H,10-12H2,1-4H3/b14-5+/t16-,18-,19-,20+,21-,23+,24+,26+/m0/s1

> <INCHI_KEY>
LJZSPOANDHXTKX-AETZWFGQSA-N

> <FORMULA>
C24H28N2O5

> <MOLECULAR_WEIGHT>
424.497

> <EXACT_MASS>
424.19982201

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.897690567286446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9S,10S,12S,13Z,15S,16S,17R,18S)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-15-ium-15-olate

> <JCHEM_LOGP>
1.1484451753333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.8830985854034554

> <JCHEM_POLAR_SURFACE_AREA>
78.89999999999999

> <JCHEM_REFRACTIVITY>
114.2793

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,10S,12S,13Z,15S,16S,17R,18S)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-15-ium-15-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.718  -0.503   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.169  -0.758   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.193   0.198   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.241   1.747   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.802   1.401   0.000  0.00  0.00           N+1
HETATM    6  O   UNK     0       1.026  -0.341   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0       2.913  -0.011   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.058  -1.333   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.792   0.229   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.210   1.425   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.050   0.170   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.759  -0.087   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.832  -1.602   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.062  -2.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.837   2.358   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.452   3.983   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.123   5.538   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.658   6.015   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.268   6.568   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.937   0.965   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.881   2.391   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.432   2.819   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.519   0.694   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.551   1.837   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.057   1.515   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.530   0.049   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.498  -1.094   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.992  -0.771   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       5.637  -1.571   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       5.912  -3.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.431  -0.552   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   22                                             
CONECT    6    5                                                            
CONECT    7    5    8   31                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   15   22                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   23   31                                             
CONECT   21   20   22                                                       
CONECT   22   21   10    5                                                  
CONECT   23   20   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    7   20                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,9S,10S,12S,13Z,15S,16S,17R,18S)-18-(acetyloxy)-13-ethylidene-8-methyl-15-oxo-8,15-diazahexacyclo[14.2.1.0,.0,.0,.0,]nonadeca-2,4,6-triene-17-carboxylic acid	Generator

Chemical Formula

C₂₄H₂₈N₂O₅

Average Mass

424.4970 Da

Monoisotopic Mass

424.19982 Da

IUPAC Name

(1R,9S,10S,12S,13Z,15S,16S,17R,18S)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-15-ium-15-olate

Traditional Name

(1R,9S,10S,12S,13Z,15S,16S,17R,18S)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-15-ium-15-olate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12[C@@H](OC(C)=O)[C@@]34C[C@@H]1[N@@+]1([O-])C\C(=C/C)[C@@H]2C[C@H]1[C@H]3N(C)C1=CC=CC=C41

InChI Identifier

InChI=1S/C24H28N2O5/c1-5-14-12-26(29)18-10-16(14)24(22(28)30-4)19(26)11-23(21(24)31-13(2)27)15-8-6-7-9-17(15)25(3)20(18)23/h5-9,16,18-21H,10-12H2,1-4H3/b14-5+/t16-,18-,19-,20+,21-,23+,24+,26+/m0/s1

InChI Key

LJZSPOANDHXTKX-AETZWFGQSA-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
Beta-carboline
Pyridoindole
Quinolizidine
Indole or derivatives
Piperidinecarboxylic acid
Dialkylarylamine
Quinuclidine
Tertiary aliphatic/aromatic amine
Azepane
Aralkylamine
Dicarboxylic acid or derivatives
Piperidine
Benzenoid
Trialkyl amine oxide
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Trisubstituted n-oxide
N-oxide
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic zwitterion
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	1.15	ChemAxon
pKa (Strongest Basic)	2.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.28 m³·mol⁻¹	ChemAxon
Polarizability	44.9 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

163189026

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate (NP0208365)

MOL for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

3D MOL for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

3D SDF for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

3D-SDF for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

PDB for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

3D PDB for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

SMILES for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

INCHI for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

Structure for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)

3D Structure for NP0208365 ((1r,9s,10s,12s,13z,15s,16s,17r,18s)-18-(acetyloxy)-13-ethylidene-17-(methoxycarbonyl)-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-15-ium-15-olate)