NP-MRD: Showing NP-Card for bisdehydrotuberostemonine D (NP0042849)

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Record Information

Version

2.0

Created at

2021-06-21 00:24:47 UTC

Updated at

2021-06-30 00:18:11 UTC

NP-MRD ID

NP0042849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

bisdehydrotuberostemonine D

Provided By

JEOL Database JEOL Logo

Description

(14R)-2beta-[(2S)-4alpha-Methyl-5-oxotetrahydrofuran-2alpha-yl]-1,2,12,13-tetradehydrostenine belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. bisdehydrotuberostemonine D is found in Arcyria cinerea, Arcyria denudata, Arcyria nutans, Lycogala epidendrum and Stemona tuberosa. bisdehydrotuberostemonine D was first documented in 2014 (Gao, Y., et al.). Based on a literature review very few articles have been published on (14R)-2beta-[(2S)-4alpha-Methyl-5-oxotetrahydrofuran-2alpha-yl]-1,2,12,13-tetradehydrostenine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102243D          

 56 60  0  0  0  0            999 V2000
   -1.0593    5.0858   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3123    3.7767   -0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8263    2.9522    0.6955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3070    2.5362    0.5216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8002    1.9758    1.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7172    1.0055    1.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3231    0.3742    2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9114    0.9093   -0.0278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3267   -0.4798   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5959    1.4751   -0.5593 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5494   -4.4165   -4.4836 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2687    0.6242   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0  0  0  0
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 12 11  1  0  0  0  0
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  4 10  1  0  0  0  0
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  3 23  1  0  0  0  0
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M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212102243D          

 56 60  0  0  0  0            999 V2000
   -1.0593    5.0858   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3123    3.7767   -0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.3070    2.5362    0.5216 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.7444    4.0226   -0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7211    1.6095   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3597   -0.5486   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0192   -0.9799   -2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5710   -1.9968   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9298   -3.9869   -5.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -2.3176   -5.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0925    2.0709    3.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    0.1452    3.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    0.9895    2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -1.4630    2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1505   -1.7030    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0  0  0  0
 14 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 24  1  0  0  0  0
 21 13  1  0  0  0  0
 20 18  1  0  0  0  0
 18 16  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 21 27  1  0  0  0  0
 23 48  1  6  0  0  0
 13 12  2  0  0  0  0
 14 41  1  1  0  0  0
 24 25  1  0  0  0  0
 16 17  1  0  0  0  0
 12 11  1  0  0  0  0
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  4 10  1  0  0  0  0
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  3 23  1  0  0  0  0
  3  2  1  0  0  0  0
 11 22  2  0  0  0  0
 10  8  1  0  0  0  0
  8  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  1  0  0  0  0
  2  1  1  0  0  0  0
  6  7  2  0  0  0  0
 23 22  1  0  0  0  0
  8  9  1  0  0  0  0
 13 14  1  0  0  0  0
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  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 16 44  1  1  0  0  0
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 15 43  1  0  0  0  0
 17 45  1  0  0  0  0
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  8 35  1  6  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(N2C3=C1[C@@]1([H])[C@]([H])(C(=O)O[C@@]1([H])[C@]([H])(C([H])([H])C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])C([H])([H])C2([H])[H])C([H])([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h10-14,17-18,20H,4-9H2,1-3H3/t11-,12+,13+,14+,17-,18+,20-/m0/s1

> <INCHI_KEY>
RFGMIDHPFYCJDM-GZJVQRGCSA-N

> <FORMULA>
C22H29NO4

> <MOLECULAR_WEIGHT>
371.477

> <EXACT_MASS>
371.209658418

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.42840548434531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R,10R,11S,14R,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2-dien-13-one

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
3.8168443099999996

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.789266330584965

> <JCHEM_POLAR_SURFACE_AREA>
57.53000000000001

> <JCHEM_REFRACTIVITY>
100.7165

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10R,11S,14R,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2-dien-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
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    0.1102    1.2148    2.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3761   -2.3176   -5.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7860    0.6193    2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    2.0709    3.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3702   -1.4630    2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1505   -1.7030    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493    0.0242    0.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
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 25 26  1  0
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  3  2  1  0
 11 22  2  0
 10  8  1  0
  8  6  1  0
  6  5  1  0
  5  4  1  0
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  6  7  2  0
 23 22  1  0
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 13 14  1  0
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  3 33  1  1
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  2 31  1  0
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 16 44  1  1
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 17 45  1  0
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 17 47  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
  9 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.059   5.086  -0.730  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.312   3.777  -0.513  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.826   2.952   0.696  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.307   2.536   0.522  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.800   1.976   1.750  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.717   1.006   1.463  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.323   0.374   2.313  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.911   0.909  -0.028  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.327  -0.480  -0.476  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.596   1.475  -0.559  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.457   0.504  -0.690  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.306  -0.617  -1.538  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.093  -1.227  -1.252  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.513  -2.456  -1.848  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.584  -2.147  -2.872  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.522  -3.366  -3.767  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.993  -3.083  -5.180  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.058  -3.712  -3.694  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.549  -4.417  -4.484  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.501  -3.149  -2.585  0.00  0.00           O+0
HETATM   21  N   UNK     0       0.506  -0.477  -0.260  0.00  0.00           N+0
HETATM   22  C   UNK     0      -0.269   0.624  -0.001  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.119   1.726   0.936  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.110   1.215   2.387  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.352   0.380   2.734  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.502  -0.939   1.967  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.732  -0.775   0.463  0.00  0.00           C+0
HETATM   28  H   UNK     0      -1.095   5.677   0.190  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.083   4.914  -1.076  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.553   5.682  -1.496  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.355   3.187  -1.436  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.744   4.023  -0.349  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.755   3.599   1.581  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.923   3.426   0.343  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.721   1.609  -0.276  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.330  -0.713  -0.101  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.663  -1.257  -0.084  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.360  -0.549  -1.567  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.739   1.954  -1.536  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.019  -0.980  -2.270  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.868  -3.139  -1.067  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.339  -1.239  -3.439  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.571  -1.997  -2.423  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.088  -4.196  -3.328  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.032  -2.741  -5.184  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.930  -3.987  -5.796  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.376  -2.318  -5.664  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.142   2.051   0.705  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.786   0.619   2.598  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.093   2.071   3.073  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.311   0.145   3.805  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.253   0.990   2.589  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.370  -1.463   2.386  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.629  -1.576   2.154  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.151  -1.703   0.066  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.449   0.024   0.243  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1   31   32                                             
CONECT    3    4   23    2   33                                             
CONECT    4    3   10    5   34                                             
CONECT    5    6    4                                                       
CONECT    6    8    5    7                                                  
CONECT    7    6                                                            
CONECT    8   10    6    9   35                                             
CONECT    9    8   36   37   38                                             
CONECT   10    4    8   11   39                                             
CONECT   11   12   22   10                                                  
CONECT   12   13   11   40                                                  
CONECT   13   21   12   14                                                  
CONECT   14   20   15   41   13                                             
CONECT   15   16   14   42   43                                             
CONECT   16   18   15   17   44                                             
CONECT   17   16   45   46   47                                             
CONECT   18   20   16   19                                                  
CONECT   19   18                                                            
CONECT   20   14   18                                                       
CONECT   21   22   13   27                                                  
CONECT   22   21   11   23                                                  
CONECT   23   24   48    3   22                                             
CONECT   24   23   25   49   50                                             
CONECT   25   24   26   51   52                                             
CONECT   26   27   25   53   54                                             
CONECT   27   21   26   55   56                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   12                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   23                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  120    0
END

RDKit          3D

56 60  0  0  0  0  0  0  0  0999 V2000
   -1.0593    5.0858   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3123    3.7767   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8263    2.9522    0.6955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3070    2.5362    0.5216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8002    1.9758    1.7495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7172    1.0055    1.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3231    0.3742    2.3132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9114    0.9093   -0.0278 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3267   -0.4798   -0.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5959    1.4751   -0.5593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4567    0.5042   -0.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063   -0.6170   -1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0933   -1.2268   -1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5134   -2.4563   -1.8481 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5841   -2.1466   -2.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5223   -3.3659   -3.7666 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9928   -3.0831   -5.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0582   -3.7119   -3.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -4.4165   -4.4836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -3.1486   -2.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -0.4766   -0.2601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2687    0.6242   -0.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1189    1.7264    0.9359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1102    1.2148    2.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522    0.3802    2.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5019   -0.9385    1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7325   -0.7746    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0948    5.6769    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0825    4.9142   -1.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5525    5.6824   -1.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3547    3.1872   -1.4362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7444    4.0226   -0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7552    3.5988    1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9230    3.4255    0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7211    1.6095   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3300   -0.7125   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6629   -1.2573   -0.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3597   -0.5486   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7387    1.9539   -1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192   -0.9799   -2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683   -3.1389   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3389   -1.2386   -3.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5710   -1.9968   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0881   -4.1958   -3.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0324   -2.7406   -5.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -3.9869   -5.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761   -2.3176   -5.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    2.0511    0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7860    0.6193    2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    2.0709    3.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    0.1452    3.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2531    0.9895    2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702   -1.4630    2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6289   -1.5762    2.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1505   -1.7030    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4493    0.0242    0.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 14 20  1  0
 22 21  1  0
 23 24  1  0
 21 13  1  0
 20 18  1  0
 18 16  1  0
 16 15  1  0
 15 14  1  0
 21 27  1  0
 23 48  1  6
 13 12  2  0
 14 41  1  1
 24 25  1  0
 16 17  1  0
 12 11  1  0
 18 19  2  0
  4 10  1  0
 27 26  1  0
 25 26  1  0
  3 23  1  0
  3  2  1  0
 11 22  2  0
 10  8  1  0
  8  6  1  0
  6  5  1  0
  5  4  1  0
  2  1  1  0
  6  7  2  0
 23 22  1  0
  8  9  1  0
 13 14  1  0
  4 34  1  6
 10 11  1  0
 10 39  1  6
  3 33  1  1
 12 40  1  0
 24 49  1  0
 24 50  1  0
 27 55  1  0
 27 56  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
  2 31  1  0
  2 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 16 44  1  1
 15 42  1  0
 15 43  1  0
 17 45  1  0
 17 46  1  0
 17 47  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
  9 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(14R)-2b-[(2S)-4a-Methyl-5-oxotetrahydrofuran-2a-yl]-1,2,12,13-tetradehydrostenine	Generator
(14R)-2Β-[(2S)-4α-methyl-5-oxotetrahydrofuran-2α-yl]-1,2,12,13-tetradehydrostenine	Generator

Chemical Formula

C₂₂H₂₉NO₄

Average Mass

371.4770 Da

Monoisotopic Mass

371.20966 Da

IUPAC Name

(9R,10R,11S,14R,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2-dien-13-one

Traditional Name

(9R,10R,11S,14R,15R)-10-ethyl-14-methyl-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-12-oxa-4-azatetracyclo[7.6.1.0^{4,16}.0^{11,15}]hexadeca-1(16),2-dien-13-one

CAS Registry Number

Not Available

SMILES

[H]C1=C(N2C3=C1[C@@]1([H])[C@]([H])(C(=O)O[C@@]1([H])[C@]([H])(C([H])([H])C([H])([H])[H])[C@@]3([H])C([H])([H])C([H])([H])C([H])([H])C2([H])[H])C([H])([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C22H29NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h10-14,17-18,20H,4-9H2,1-3H3/t11-,12+,13+,14+,17-,18+,20-/m0/s1

InChI Key

RFGMIDHPFYCJDM-GZJVQRGCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Arcyria cinerea	Amoebozoa	KNApSAcK
Arcyria denudata	Amoebozoa	KNApSAcK
Arcyria nutans	Amoebozoa	KNApSAcK
Lycogala epidendrum	Amoebozoa	KNApSAcK
Stemona tuberosa	JEOL database	Gao, Y., et al. J. Tetrahedron 70, 967 (2014)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stichoneurine-type alkaloids

Alternative Parents

Substituents

Stichoneurine-type alkaloid
Pyrroloazepine
Indole or derivatives
Azepine
Dicarboxylic acid or derivatives
Gamma butyrolactone
Substituted pyrrole
Oxolane
Pyrrole
Heteroaromatic compound
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.01	ALOGPS
logP	3.82	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.72 m³·mol⁻¹	ChemAxon
Polarizability	41.43 Å³	ChemAxon
Number of Rings	5	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

102126214

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gao, Y., et al. (2014). Gao, Y., et al. J. Tetrahedron 70, 967 (2014). J. Tetrahedron.

Showing NP-Card for bisdehydrotuberostemonine D (NP0042849)

MOL for NP0042849 (bisdehydrotuberostemonine D)

3D MOL for NP0042849 (bisdehydrotuberostemonine D)

3D SDF for NP0042849 (bisdehydrotuberostemonine D)

3D-SDF for NP0042849 (bisdehydrotuberostemonine D)

PDB for NP0042849 (bisdehydrotuberostemonine D)

3D PDB for NP0042849 (bisdehydrotuberostemonine D)

SMILES for NP0042849 (bisdehydrotuberostemonine D)

INCHI for NP0042849 (bisdehydrotuberostemonine D)

Structure for NP0042849 (bisdehydrotuberostemonine D)

3D Structure for NP0042849 (bisdehydrotuberostemonine D)