NP-MRD: Showing NP-Card for (5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0262770)

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Record Information

Version

2.0

Created at

2022-09-08 05:44:23 UTC

Updated at

2022-09-08 05:44:23 UTC

NP-MRD ID

NP0262770

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate

Description

(5R,6S,8R,13S)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl benzoate belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position. (5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate is found in Aconitum japonicum, Aconitum karakolicum and Aconitum kusnezoffii. Based on a literature review very few articles have been published on (5R,6S,8R,13S)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-4-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082207442D          

 44 50  0  0  1  0            999 V2000
    0.7903   -3.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484   -1.5670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -0.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   -0.0814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0500    0.3632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801    0.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844    0.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474    1.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340    2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839   -0.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    0.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0011    0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5555    0.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2936    1.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3046    2.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 13 38  1  0  0  0  0
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 29 40  1  0  0  0  0
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 40 42  1  0  0  0  0
 16 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
M  END

     RDKit          3D

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  7 52  1  0
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M  END


  Mrv1652309082207442D          

 44 50  0  0  1  0            999 V2000
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    0.6451   -2.5613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484   -1.5670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -0.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482   -0.0814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0500    0.3632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945    1.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801    0.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844    0.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106    0.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6474    1.2283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340    2.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -0.5249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839   -0.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6107    0.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310   -0.2387    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2960   -0.0863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0011    0.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5555    0.9178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2936    1.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3046    2.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0025    0.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7224    1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4313    0.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4202    0.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7003   -0.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9914    0.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570   -0.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746   -1.4672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2109   -2.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5912   -2.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7692   -3.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8045   -2.6641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673   -1.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586   -1.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6049   -1.9458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3106   -2.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4484   -0.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7907   -1.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0889   -1.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6017   -2.3311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7071   -1.0844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5473   -1.4526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0443   -2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 18 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 35 38  1  0  0  0  0
 13 38  1  0  0  0  0
  5 38  1  0  0  0  0
 34 39  1  0  0  0  0
  3 39  1  0  0  0  0
 13 39  1  0  0  0  0
 29 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 16 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262770

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(CCC(OC)C34C5C[C@@]6(O)C(OC(=O)C7=CC=CC=C7)C5[C@@](OC(C)=O)(C(C(OC)C23)C14)C(O)[C@@H]6OC)OC

> <INCHI_IDENTIFIER>
InChI=1S/C33H45NO10/c1-7-34-16-30(42-6)14-13-20(39-3)32-19-15-31(38)27(43-29(37)18-11-9-8-10-12-18)21(19)33(44-17(2)35,26(36)28(31)41-5)22(25(32)34)23(40-4)24(30)32/h8-12,19-28,36,38H,7,13-16H2,1-6H3/t19?,20?,21?,22?,23?,24?,25?,26?,27?,28-,30+,31+,32?,33+/m0/s1

> <INCHI_KEY>
LKLPHWDWSQCGRK-DMMNHLJFSA-N

> <FORMULA>
C33H45NO10

> <MOLECULAR_WEIGHT>
615.72

> <EXACT_MASS>
615.304346653

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
64.41247116471364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6S,8R,13S)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <JCHEM_LOGP>
0.6233656846666684

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.250540296685841

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.539223265583342

> <JCHEM_PKA_STRONGEST_BASIC>
9.88398955140943

> <JCHEM_POLAR_SURFACE_AREA>
133.22000000000003

> <JCHEM_REFRACTIVITY>
155.51229999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6S,8R,13S)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.475  -6.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.204  -4.781   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.770  -2.925   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.723  -1.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.397  -0.152   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.093   0.678   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.923   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.830   1.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.331   1.821   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.313   0.627   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.942   2.293   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.544   3.906   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.923  -0.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.383  -0.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.740   0.873   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.271  -0.446   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.886  -0.161   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.469   0.198   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.504   1.713   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.881   2.484   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.902   4.024   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.205   1.697   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.548   2.449   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.872   1.661   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.851   0.121   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.507  -0.631   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.184   0.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.266  -1.186   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.113  -2.739   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.994  -4.378   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.837  -5.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.169  -6.941   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.368  -4.973   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.419  -3.175   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.536  -2.541   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.129  -3.632   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.580  -3.774   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.704  -0.854   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.343  -2.804   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.633  -3.120   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.590  -4.351   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.787  -2.024   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      10.355  -2.712   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      11.283  -4.026   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8   38                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   38   39                                             
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18   42                                             
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22                                                       
CONECT   28   18   14   29                                                  
CONECT   29   28   30   34   40                                             
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   29   35   39                                                  
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   13    5                                                  
CONECT   39   34    3   13                                                  
CONECT   40   29   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   16   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Value	Source
(5R,6S,8R,13S)-8-(Acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-4-yl benzoic acid	Generator

Chemical Formula

C₃₃H₄₅NO₁₀

Average Mass

615.7200 Da

Monoisotopic Mass

615.30435 Da

IUPAC Name

(5R,6S,8R,13S)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

Traditional Name

(5R,6S,8R,13S)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(CCC(OC)C34C5C[C@@]6(O)C(OC(=O)C7=CC=CC=C7)C5[C@@](OC(C)=O)(C(C(OC)C23)C14)C(O)[C@@H]6OC)OC

InChI Identifier

InChI=1S/C33H45NO10/c1-7-34-16-30(42-6)14-13-20(39-3)32-19-15-31(38)27(43-29(37)18-11-9-8-10-12-18)21(19)33(44-17(2)35,26(36)28(31)41-5)22(25(32)34)23(40-4)24(30)32/h8-12,19-28,36,38H,7,13-16H2,1-6H3/t19?,20?,21?,22?,23?,24?,25?,26?,27?,28-,30+,31+,32?,33+/m0/s1

InChI Key

LKLPHWDWSQCGRK-DMMNHLJFSA-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
Aconitum japonicum	LOTUS Database	35616633
Aconitum karakolicum	LOTUS Database	35616633
Aconitum kusnezoffii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lappaconitine-type diterpenoid alkaloids. These are c18-bisnorditerpenoid alkaloids with a structure based on the heptacyclic lappaconitine skeleton. Lappaconitine similar to aconitane, with the difference that the former lacks a carbon atom at the 18-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Lappaconitine-type diterpenoid alkaloids

Alternative Parents

Substituents

Lappaconitine-type diterpenoid alkaloid
Quinolidine
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Benzoyl
Azepane
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	0.62	ChemAxon
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	9.88	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	133.22 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	155.51 m³·mol⁻¹	ChemAxon
Polarizability	64.41 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

4475582

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316549

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0262770)

MOL for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D MOL for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D SDF for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D-SDF for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

PDB for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D PDB for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

SMILES for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

INCHI for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

Structure for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D Structure for NP0262770 ((5r,6s,8r,13s)-8-(acetyloxy)-11-ethyl-5,7-dihydroxy-6,13,16,18-tetramethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)