NP-MRD: Showing NP-Card for stemona-amine D (NP0042658)

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Record Information

Version

2.0

Created at

2021-06-21 00:16:05 UTC

Updated at

2021-06-30 00:17:52 UTC

NP-MRD ID

NP0042658

Secondary Accession Numbers

None

Natural Product Identification

Common Name

stemona-amine D

Provided By

JEOL Database JEOL Logo

Description

Stemona-amine D 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. stemona-amine D is found in Stemona tuberosa. stemona-amine D was first documented in 2013 (Hitotsuyanagi, Y., et al.). Based on a literature review very few articles have been published on Stemona-amine D.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102163D          

 61 65  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102163D          

 61 65  0  0  0  0            999 V2000
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    0.6685    1.3799   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
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 26 27  1  0  0  0  0
 18 24  1  0  0  0  0
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 12 28  1  0  0  0  0
 28 27  1  0  0  0  0
  3  4  1  0  0  0  0
 12 13  1  0  0  0  0
 24 22  1  0  0  0  0
 22 20  1  0  0  0  0
 20 19  1  0  0  0  0
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 11 12  1  0  0  0  0
 11 40  1  1  0  0  0
 13 14  1  0  0  0  0
  4 35  1  1  0  0  0
 11  4  1  0  0  0  0
  8 10  1  6  0  0  0
 16 15  1  0  0  0  0
  3  2  1  0  0  0  0
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 28 61  1  1  0  0  0
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 18 49  1  6  0  0  0
  5  6  1  0  0  0  0
 20 21  1  0  0  0  0
  6  8  1  0  0  0  0
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 17 48  1  6  0  0  0
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 22 23  2  0  0  0  0
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  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042658

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C(=O)O[C@]2([H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]3([H])[C@@]4([H])N(C([H])([H])C([H])([H])C([H])([H])[C@@]3([H])[C@]12[H])[C@@]([H])(C([H])([H])C4([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO5/c1-4-12-17-13(18-19(12)28-21(25)22(18,3)26)6-5-9-23-14(7-8-15(17)23)16-10-11(2)20(24)27-16/h11-19,26H,4-10H2,1-3H3/t11-,12-,13+,14-,15-,16-,17-,18-,19+,22-/m0/s1

> <INCHI_KEY>
PMKAPBDTZVDGSB-VWXKGAOLSA-N

> <FORMULA>
C22H33NO5

> <MOLECULAR_WEIGHT>
391.508

> <EXACT_MASS>
391.235873167

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.243829482196425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5S,10R,11S,12S,15R,16S)-16-ethyl-12-hydroxy-12-methyl-5-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-14-oxa-6-azatetracyclo[8.6.0.0^{2,6}.0^{11,15}]hexadecan-13-one

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.134933020509655

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.328680336579755

> <JCHEM_PKA_STRONGEST_BASIC>
11.296706106142567

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
102.10990000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,10R,11S,12S,15R,16S)-16-ethyl-12-hydroxy-12-methyl-5-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-14-oxa-6-azatetracyclo[8.6.0.0^{2,6}.0^{11,15}]hexadecan-13-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
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   -1.4826   -0.7398    1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
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 28  3  1  0
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 11  4  1  0
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 22 23  2  0
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  6  7  2  0
 25 26  1  0
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  1 30  1  0
  1 31  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       1.349   0.315   4.406  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.402  -0.286   3.375  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.050   0.736   2.319  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.943   1.842   2.899  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.292   3.108   2.722  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.138   3.986   2.114  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.827   5.109   1.747  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.524   3.374   1.981  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.380   3.851   3.154  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.187   3.720   0.778  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.212   1.886   2.064  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.857   1.174   0.739  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.129   0.628   0.081  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.914  -0.114  -1.230  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.078  -1.385  -1.096  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.636  -1.216  -1.064  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.010  -0.741  -2.310  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.027  -1.777  -3.449  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.582  -3.142  -3.087  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.020  -3.668  -4.439  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.139  -4.687  -4.339  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.445  -2.398  -5.130  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.170  -2.319  -6.107  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.866  -1.320  -4.520  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.365  -0.262  -1.856  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.054   0.367  -0.513  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.006  -0.565   0.092  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.889   0.066   1.195  0.00  0.00           C+0
HETATM   29  H   UNK     0       1.677  -0.458   5.109  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.239   0.731   3.922  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.869   1.109   4.983  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.470  -0.708   3.890  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.916  -1.120   2.885  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.849   1.201   1.900  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.161   1.717   3.965  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.548   4.933   3.094  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.915   3.639   4.122  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.368   3.378   3.130  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.054   4.680   0.651  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.011   1.327   2.569  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.358   1.870   0.056  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.823   1.453  -0.114  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.652  -0.040   0.779  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.504   0.568  -1.981  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.904  -0.405  -1.607  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.329  -2.041  -1.939  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.399  -1.952  -0.213  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.526   0.151  -2.687  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.985  -1.887  -3.862  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.162  -3.784  -2.606  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.442  -3.065  -2.412  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.166  -4.082  -4.987  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.430  -5.040  -5.335  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.826  -5.553  -3.749  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.034  -4.258  -3.874  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.807   0.462  -2.549  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.075  -1.086  -1.724  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.669   1.380  -0.666  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.958   0.430   0.102  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.551  -1.374   0.585  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.483  -0.740   1.652  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1   32   33                                             
CONECT    3   28    4    2   34                                             
CONECT    4    3   35   11    5                                             
CONECT    5    4    6                                                       
CONECT    6    5    8    7                                                  
CONECT    7    6                                                            
CONECT    8   10    6   11    9                                             
CONECT    9    8   36   37   38                                             
CONECT   10    8   39                                                       
CONECT   11   12   40    4    8                                             
CONECT   12   28   13   11   41                                             
CONECT   13   12   14   42   43                                             
CONECT   14   13   15   44   45                                             
CONECT   15   16   14   46   47                                             
CONECT   16   15   27   17                                                  
CONECT   17   18   48   16   25                                             
CONECT   18   24   19   17   49                                             
CONECT   19   20   18   50   51                                             
CONECT   20   22   19   21   52                                             
CONECT   21   20   53   54   55                                             
CONECT   22   24   20   23                                                  
CONECT   23   22                                                            
CONECT   24   18   22                                                       
CONECT   25   17   26   56   57                                             
CONECT   26   27   25   58   59                                             
CONECT   27   26   28   16   60                                             
CONECT   28    3   12   27   61                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   25                                                            
CONECT   57   25                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   27                                                            
CONECT   61   28                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  130    0
END

RDKit          3D

61 65  0  0  0  0  0  0  0  0999 V2000
    1.3493    0.3145    4.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4018   -0.2856    3.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    0.7357    2.3189 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9429    1.8422    2.8987 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2923    3.1076    2.7224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376    3.9863    2.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8268    5.1094    1.7470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5244    3.3739    1.9806 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3800    3.8511    3.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1867    3.7198    0.7779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118    1.8863    2.0640 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8570    1.1735    0.7393 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1293    0.6278    0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -0.1137   -1.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781   -1.3855   -1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6362   -1.2162   -1.0637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0098   -0.7414   -2.3096 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0271   -1.7769   -3.4494 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5822   -3.1418   -3.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203   -3.6678   -4.4389 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1395   -4.6867   -4.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449   -2.3977   -5.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1704   -2.3189   -6.1069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663   -1.3201   -4.5196 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3652   -0.2622   -1.8563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    0.3665   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058   -0.5649    0.0922 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8892    0.0663    1.1954 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6772   -0.4580    5.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2389    0.7309    3.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8685    1.1090    4.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4695   -0.7084    3.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9164   -1.1199    2.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8487    1.2009    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1607    1.7170    3.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483    4.9329    3.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    3.6391    4.1225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3681    3.3781    3.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543    4.6800    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    1.3274    2.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3576    1.8697    0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8231    1.4533   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6522   -0.0398    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040    0.5681   -1.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9035   -0.4048   -1.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286   -2.0406   -1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3994   -1.9525   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258    0.1509   -2.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9846   -1.8865   -3.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1621   -3.7838   -2.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416   -3.0646   -2.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1664   -4.0820   -4.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -5.0396   -5.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -5.5535   -3.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0339   -4.2580   -3.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068    0.4615   -2.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750   -1.0857   -1.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6685    1.3799   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    0.4304    0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -1.3743    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826   -0.7398    1.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 27  1  0
 18 24  1  0
 28  3  1  0
 12 28  1  0
 28 27  1  0
  3  4  1  0
 12 13  1  0
 24 22  1  0
 22 20  1  0
 20 19  1  0
 19 18  1  0
 17 18  1  0
 11 12  1  0
 11 40  1  1
 13 14  1  0
  4 35  1  1
 11  4  1  0
  8 10  1  6
 16 15  1  0
  3  2  1  0
 14 15  1  0
 28 61  1  1
 27 16  1  0
 27 60  1  1
  4  5  1  0
 18 49  1  6
  5  6  1  0
 20 21  1  0
  6  8  1  0
 12 41  1  6
  8 11  1  0
  8  9  1  0
 17 48  1  6
 16 17  1  0
 22 23  2  0
 17 25  1  0
  6  7  2  0
 25 26  1  0
  2  1  1  0
  3 34  1  6
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 20 52  1  6
 19 50  1  0
 19 51  1  0
 10 39  1  0
  2 32  1  0
  2 33  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₅

Average Mass

391.5080 Da

Monoisotopic Mass

391.23587 Da

IUPAC Name

(1R,2S,5S,10R,11S,12S,15R,16S)-16-ethyl-12-hydroxy-12-methyl-5-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-14-oxa-6-azatetracyclo[8.6.0.0^{2,6}.0^{11,15}]hexadecan-13-one

Traditional Name

(1R,2S,5S,10R,11S,12S,15R,16S)-16-ethyl-12-hydroxy-12-methyl-5-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-14-oxa-6-azatetracyclo[8.6.0.0^{2,6}.0^{11,15}]hexadecan-13-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C(=O)O[C@]2([H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]3([H])[C@@]4([H])N(C([H])([H])C([H])([H])C([H])([H])[C@@]3([H])[C@]12[H])[C@@]([H])(C([H])([H])C4([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H33NO5/c1-4-12-17-13(18-19(12)28-21(25)22(18,3)26)6-5-9-23-14(7-8-15(17)23)16-10-11(2)20(24)27-16/h11-19,26H,4-10H2,1-3H3/t11-,12-,13+,14-,15-,16-,17-,18-,19+,22-/m0/s1

InChI Key

PMKAPBDTZVDGSB-VWXKGAOLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona tuberosa	JEOL database	Hitotsuyanagi, Y., et al, Tetrahedron Lett. 54, 6995 (2013)

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
Azepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
N-alkylpyrrolidine
Oxolane
Pyrrolidine
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Lactone
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Alcohol
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.56	ALOGPS
logP	2.13	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.33	ChemAxon
pKa (Strongest Basic)	11.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.11 m³·mol⁻¹	ChemAxon
Polarizability	43.24 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

34485498

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102219916

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hitotsuyanagi, Y., et al. (2013). Hitotsuyanagi, Y., et al, Tetrahedron Lett. 54, 6995 (2013). Tetrahedron Lett.

Showing NP-Card for stemona-amine D (NP0042658)

MOL for NP0042658 (stemona-amine D)

3D MOL for NP0042658 (stemona-amine D)

3D SDF for NP0042658 (stemona-amine D)

3D-SDF for NP0042658 (stemona-amine D)

PDB for NP0042658 (stemona-amine D)

3D PDB for NP0042658 (stemona-amine D)

SMILES for NP0042658 (stemona-amine D)

INCHI for NP0042658 (stemona-amine D)

Structure for NP0042658 (stemona-amine D)

3D Structure for NP0042658 (stemona-amine D)