NP-MRD: Showing NP-Card for voacalgine C (NP0042779)

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Record Information

Version

2.0

Created at

2021-06-21 00:21:15 UTC

Updated at

2021-06-30 00:18:04 UTC

NP-MRD ID

NP0042779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

voacalgine C

Provided By

JEOL Database JEOL Logo

Description

Voacalgine C belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. voacalgine C is found in Voacanga grandifolia. voacalgine C was first documented in 2013 (Hirasawa, Y., et al.). Based on a literature review very few articles have been published on Voacalgine C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102213D          

 66 72  0  0  0  0            999 V2000
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    3.0166    1.0910    0.1285 N   0  0  2  0  0  0  0  0  0  0  0  0
    2.9014    1.0023    1.6054 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102213D          

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M  END
> <DATABASE_ID>
NP0042779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])O[C@]11O[C@@]2(OC([H])([H])[C@@]3([H])[C@@]4([H])N(C([H])([H])[H])[C@]([H])(C5=C(C6=C(C([H])=C([H])C([H])=C6[H])N5C([H])([H])[H])C4([H])[H])C([H])([H])[C@@]3([H])[C@]2([H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H34N2O4/c1-25-19(13-26(32-25)23(29)9-6-10-30-26)16-11-22-24-17(12-21(27(22)2)18(16)14-31-25)15-7-4-5-8-20(15)28(24)3/h4-5,7-8,16,18-19,21-23,29H,6,9-14H2,1-3H3/t16-,18-,19+,21+,22+,23+,25+,26-/m1/s1

> <INCHI_KEY>
VBDQTJIQJAGBJF-RLHFXQFGSA-N

> <FORMULA>
C26H34N2O4

> <MOLECULAR_WEIGHT>
438.568

> <EXACT_MASS>
438.251857583

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.1219006204594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3'S,12S,13R,16S,18R,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazaspiro[hexacyclo[10.10.1.0^{2,10}.0^{4,9}.0^{13,21}.0^{16,20}]tricosane-18,2'-oxane]-2(10),4(9),5,7-tetraen-3'-ol

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.9573592856666666

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.241507135940495

> <JCHEM_PKA_STRONGEST_BASIC>
7.359480749943999

> <JCHEM_POLAR_SURFACE_AREA>
56.09000000000001

> <JCHEM_REFRACTIVITY>
122.2238

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3'S,12S,13R,16S,18R,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazaspiro[hexacyclo[10.10.1.0^{2,10}.0^{4,9}.0^{13,21}.0^{16,20}]tricosane-18,2'-oxane]-2(10),4(9),5,7-tetraen-3'-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 17 52  1  0
 17 53  1  0
 14 50  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       4.396   0.929  -0.328  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.017   1.091   0.129  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.901   1.002   1.605  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.508   1.544   1.985  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.351   0.789   1.287  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.003   1.476   1.540  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.176   0.512   1.391  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.351   1.474   1.270  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.767   1.805   2.609  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.816   2.774   2.635  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.065   2.258   1.934  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.745   1.796   0.514  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.541   0.853   0.501  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.939  -0.396   1.089  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.853   2.638   0.606  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.415   2.567   0.542  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.913   3.967   0.880  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.079   2.217  -0.799  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.288   1.862  -0.994  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.630   0.584  -0.219  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.086   0.127  -0.517  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.326  -1.374  -0.133  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.767  -1.522   1.285  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.054  -0.419   2.065  0.00  0.00           C+0
HETATM   25  N   UNK     0       3.454  -0.863   3.298  0.00  0.00           N+0
HETATM   26  C   UNK     0       3.843  -0.042   4.423  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.437  -2.248   3.321  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.769  -3.156   4.341  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.653  -4.523   4.072  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.222  -4.974   2.829  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.896  -4.066   1.817  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.003  -2.683   2.063  0.00  0.00           C+0
HETATM   33  H   UNK     0       4.833  -0.045  -0.083  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.033   1.705   0.109  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.452   1.059  -1.415  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.660   1.644   2.068  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.366   1.485   3.072  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.475   2.608   1.732  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.297  -0.203   1.756  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.033   1.871   2.565  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.257  -0.165   2.248  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.073  -0.091   0.482  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.468   3.713   2.191  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.045   2.981   3.686  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.470   1.411   2.500  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.837   3.034   1.915  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.626   1.296   0.095  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.533   2.672  -0.111  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.261   0.653  -0.540  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.926  -0.265   2.055  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.240   4.272   1.881  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.173   4.062   0.823  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.329   4.696   0.174  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.415   1.685  -2.067  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.939   2.704  -0.737  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.055  -0.195  -0.580  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.213   0.191  -1.607  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.425  -1.969  -0.316  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.119  -1.778  -0.776  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.566   0.999   4.250  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.926  -0.125   4.546  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.325  -0.402   5.316  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.108  -2.817   5.315  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.903  -5.244   4.848  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.139  -6.041   2.639  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.563  -4.426   0.848  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3   21    1                                                  
CONECT    3    2    4   24   36                                             
CONECT    4    3    5   37   38                                             
CONECT    5    4   20    6   39                                             
CONECT    6    5   16    7   40                                             
CONECT    7    6    8   41   42                                             
CONECT    8    9   13    7   15                                             
CONECT    9    8   10                                                       
CONECT   10   11    9   43   44                                             
CONECT   11   12   10   45   46                                             
CONECT   12   13   11   47   48                                             
CONECT   13   12    8   14   49                                             
CONECT   14   13   50                                                       
CONECT   15    8   16                                                       
CONECT   16   18    6   15   17                                             
CONECT   17   16   51   52   53                                             
CONECT   18   16   19                                                       
CONECT   19   20   18   54   55                                             
CONECT   20   21    5   19   56                                             
CONECT   21    2   20   22   57                                             
CONECT   22   21   23   58   59                                             
CONECT   23   24   22   32                                                  
CONECT   24   25   23    3                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   60   61   62                                             
CONECT   27   28   32   25                                                  
CONECT   28   27   29   63                                                  
CONECT   29   30   28   64                                                  
CONECT   30   31   29   65                                                  
CONECT   31   32   30   66                                                  
CONECT   32   27   31   23                                                  
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    7                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   17                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
CONECT   60   26                                                            
CONECT   61   26                                                            
CONECT   62   26                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  144    0
END

RDKit          3D

66 72  0  0  0  0  0  0  0  0999 V2000
    4.3960    0.9285   -0.3284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166    1.0910    0.1285 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9014    1.0023    1.6054 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5082    1.5441    1.9850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    0.7892    1.2870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0026    1.4762    1.5396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1757    0.5120    1.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3513    1.4741    1.2700 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7665    1.8053    2.6093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8162    2.7738    2.6352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    2.2580    1.9337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7454    1.7959    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5408    0.8525    0.5008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9389   -0.3960    1.0886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8527    2.6379    0.6062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4147    2.5667    0.5421 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9127    3.9675    0.8803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0785    2.2172   -0.7991 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2883    1.8624   -0.9937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6300    0.5843   -0.2190 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0860    0.1265   -0.5173 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3262   -1.3741   -0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7672   -1.5219    1.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0536   -0.4186    2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.8625    3.2977 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432   -0.0422    4.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -2.2484    3.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689   -3.1559    4.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6526   -4.5231    4.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2223   -4.9742    2.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -4.0655    1.8167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0033   -2.6825    2.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8329   -0.0445   -0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    1.7054    0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4516    1.0590   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6604    1.6441    2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656    1.4849    3.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4752    2.6085    1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2970   -0.2027    1.7562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334    1.8715    2.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2575   -0.1647    2.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728   -0.0905    0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4685    3.7135    2.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0453    2.9811    3.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4702    1.4107    2.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8373    3.0340    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6259    1.2958    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5333    2.6718   -0.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609    0.6525   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9263   -0.2653    2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2398    4.2716    1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1727    4.0624    0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3286    4.6960    0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149    1.6853   -2.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391    2.7039   -0.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0550   -0.1947   -0.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2127    0.1907   -1.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247   -1.9693   -0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1192   -1.7781   -0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5660    0.9987    4.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9260   -0.1252    4.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251   -0.4016    5.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1076   -2.8168    5.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9032   -5.2435    4.8476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -6.0412    2.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5632   -4.4260    0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
  3  2  1  0
 21  2  1  0
 25 24  1  0
  8  9  1  1
 13 12  1  0
  3  4  1  0
 21 20  1  0
  4  5  1  0
 20  5  1  0
 23 24  2  0
 24  3  1  0
 12 11  1  0
 21 22  1  0
 20 19  1  0
  5  6  1  0
 16 18  1  0
 18 19  1  0
 22 23  1  0
 20 56  1  6
 11 10  1  0
  5 39  1  1
 10  9  1  0
  3 36  1  1
 27 32  2  0
 21 57  1  6
 25 26  1  0
 32 31  1  0
  2  1  1  0
 16  6  1  0
 23 32  1  0
 31 30  2  0
  8 13  1  0
 30 29  1  0
  6  7  1  0
  7  8  1  0
  8 15  1  0
 15 16  1  0
 27 25  1  0
 16 17  1  1
 29 28  2  0
 13 14  1  0
 13 49  1  6
 12 47  1  0
 12 48  1  0
 11 45  1  0
 11 46  1  0
 10 43  1  0
 10 44  1  0
 22 58  1  0
 22 59  1  0
 31 66  1  0
 30 65  1  0
 29 64  1  0
 28 63  1  0
  4 37  1  0
  4 38  1  0
 19 54  1  0
 19 55  1  0
 26 60  1  0
 26 61  1  0
 26 62  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  6 40  1  1
  7 41  1  0
  7 42  1  0
 17 51  1  0
 17 52  1  0
 17 53  1  0
 14 50  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄N₂O₄

Average Mass

438.5680 Da

Monoisotopic Mass

438.25186 Da

IUPAC Name

(1S,3'S,12S,13R,16S,18R,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazaspiro[hexacyclo[10.10.1.0^{2,10}.0^{4,9}.0^{13,21}.0^{16,20}]tricosane-18,2'-oxane]-2(10),4(9),5,7-tetraen-3'-ol

Traditional Name

(1S,3'S,12S,13R,16S,18R,20S,21R)-3,16,23-trimethyl-15,17-dioxa-3,23-diazaspiro[hexacyclo[10.10.1.0^{2,10}.0^{4,9}.0^{13,21}.0^{16,20}]tricosane-18,2'-oxane]-2(10),4(9),5,7-tetraen-3'-ol

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])O[C@]11O[C@@]2(OC([H])([H])[C@@]3([H])[C@@]4([H])N(C([H])([H])[H])[C@]([H])(C5=C(C6=C(C([H])=C([H])C([H])=C6[H])N5C([H])([H])[H])C4([H])[H])C([H])([H])[C@@]3([H])[C@]2([H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C26H34N2O4/c1-25-19(13-26(32-25)23(29)9-6-10-30-26)16-11-22-24-17(12-21(27(22)2)18(16)14-31-25)15-7-4-5-8-20(15)28(24)3/h4-5,7-8,16,18-19,21-23,29H,6,9-14H2,1-3H3/t16-,18-,19+,21+,22+,23+,25+,26-/m1/s1

InChI Key

VBDQTJIQJAGBJF-RLHFXQFGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Voacanga grandifolia	JEOL database	Hirasawa, Y., et. al, Tetrahedron 69, 10869 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Beta-carboline
Pyridoindole
3-alkylindole
N-alkylindole
Furopyran
Indole
Indole or derivatives
Ketal
Aralkylamine
Oxane
Benzenoid
Piperidine
Substituted pyrrole
Pyran
N-methylpyrrole
Heteroaromatic compound
Furan
Oxolane
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.35	ALOGPS
logP	2.96	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	7.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	122.22 m³·mol⁻¹	ChemAxon
Polarizability	49.12 Å³	ChemAxon
Number of Rings	7	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

102225984

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hirasawa, Y., et al. (2013). Hirasawa, Y., et. al, Tetrahedron 69, 10869 (2013). Tetrahedron.

Showing NP-Card for voacalgine C (NP0042779)

MOL for NP0042779 (voacalgine C)

3D MOL for NP0042779 (voacalgine C)

3D SDF for NP0042779 (voacalgine C)

3D-SDF for NP0042779 (voacalgine C)

PDB for NP0042779 (voacalgine C)

3D PDB for NP0042779 (voacalgine C)

SMILES for NP0042779 (voacalgine C)

INCHI for NP0042779 (voacalgine C)

Structure for NP0042779 (voacalgine C)

3D Structure for NP0042779 (voacalgine C)