NP-MRD: Showing NP-Card for (1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate (NP0256100)

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Record Information

Version

2.0

Created at

2022-09-07 20:49:17 UTC

Updated at

2022-09-07 20:49:17 UTC

NP-MRD ID

NP0256100

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate

Description

N-Deacetyllappaconitine 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. (1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate is found in Aconitum barbatum, Aconitum leucostomum, Aconitum orientale, Aconitum septentrionale, Aconitum sinomontanum and Delphinium cashmerianum. (1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate was first documented in 2004 (PMID: 15548242). Based on a literature review a small amount of articles have been published on N-Deacetyllappaconitine (PMID: 28104561) (PMID: 16238304) (PMID: 35739330).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222492D          

 39 45  0  0  1  0            999 V2000
   -1.4010    0.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774    0.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069   -0.0868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.6016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0643   -1.8895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -2.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5656   -3.2286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9746   -2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118   -3.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849   -4.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208   -3.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3836   -2.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6105   -2.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -1.6519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0580   -2.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4081   -1.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6885    0.4063    0.0000 C   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  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
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 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
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  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
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 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
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  3 22  1  0  0  0  0
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  5 25  1  0  0  0  0
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 33 34  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
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 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

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    3.8724    1.0379   -0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4949    1.5031   -1.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6877    1.0037    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9240    1.4262    1.9699 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1586    2.8011    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0752    0.0747    0.8829 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9569   -0.9213    1.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  4  1  0
  4  5  1  0
  5 16  1  0
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  5  6  1  6
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 10 47  1  0
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 15 51  1  0
 15 52  1  0
M  END


  Mrv1652309072222492D          

 39 45  0  0  1  0            999 V2000
   -1.4010    0.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774    0.6504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2069   -0.0868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538   -0.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.6016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0643   -1.8895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2015   -2.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9746   -2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118   -3.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849   -4.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3836   -2.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6105   -2.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733   -1.6519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7469   -2.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2722   -2.0163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0767   -2.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207   -2.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612   -1.1556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7487   -0.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250    0.0210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3169   -0.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081   -1.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2326   -0.2113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2339    0.6137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0465   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6656   -0.5916    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4651   -0.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -1.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5718   -2.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -1.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3162   -1.0433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0733   -0.7155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9615   -1.7836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8892   -2.6054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5648   -3.0789    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  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
  5 25  1  0  0  0  0
 21 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  6  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256100

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(CC[C@H](OC)[C@@]34C5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@@H](CC23)C14)OC(=O)C1=CC=CC=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C30H42N2O7/c1-5-32-15-27(39-26(33)16-8-6-7-9-19(16)31)11-10-23(37-3)29-21(27)13-18(24(29)32)28(34)14-20(36-2)17-12-22(29)30(28,35)25(17)38-4/h6-9,17-18,20-25,34-35H,5,10-15,31H2,1-4H3/t17-,18+,20+,21?,22?,23+,24?,25+,27-,28+,29+,30+/m1/s1

> <INCHI_KEY>
VSUODASNSRJNCP-WUOZJDCCSA-N

> <FORMULA>
C30H42N2O7

> <MOLECULAR_WEIGHT>
542.673

> <EXACT_MASS>
542.2992017

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.21092726076501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,4S,5R,6S,8S,9S,13S,16S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl 2-aminobenzoate

> <JCHEM_LOGP>
1.212518876666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.109702596463958

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.514235436314099

> <JCHEM_PKA_STRONGEST_BASIC>
9.038636403622274

> <JCHEM_POLAR_SURFACE_AREA>
123.71000000000002

> <JCHEM_REFRACTIVITY>
143.926

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,4S,5R,6S,8S,9S,13S,16S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl 2-aminobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.615   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.078   1.214   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.386  -0.162   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.220  -1.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.543  -2.990   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.987  -3.527   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.243  -5.046   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.056  -6.027   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.686  -5.583   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.942  -7.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.385  -7.639   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.572  -6.658   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.316  -5.140   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.873  -4.602   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -4.617  -3.084   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -0.108  -4.529   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.394  -4.958   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.375  -3.764   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.877  -4.105   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.332  -5.576   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.981  -2.157   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.398  -0.333   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.473   0.039   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.591  -0.598   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.762  -2.285   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.167  -0.394   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.170   1.146   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.687  -0.011   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.842  -1.104   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.335  -0.724   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.752   0.758   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.329  -2.683   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.801  -4.005   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.442  -2.953   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.324  -1.947   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.737  -1.336   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.528  -3.329   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.393  -4.863   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.654  -5.747   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16   25                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16    5   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   25   34                                             
CONECT   22   21    3   23                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24    5   21                                                  
CONECT   26   23   27   28   35                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   21   35                                                  
CONECT   35   34   26   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   32   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂N₂O₇

Average Mass

542.6730 Da

Monoisotopic Mass

542.29920 Da

IUPAC Name

(1S,3S,4S,5R,6S,8S,9S,13S,16S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl 2-aminobenzoate

Traditional Name

(1S,3S,4S,5R,6S,8S,9S,13S,16S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl 2-aminobenzoate

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(CC[C@H](OC)[C@@]34C5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@@H](CC23)C14)OC(=O)C1=CC=CC=C1N

InChI Identifier

InChI=1S/C30H42N2O7/c1-5-32-15-27(39-26(33)16-8-6-7-9-19(16)31)11-10-23(37-3)29-21(27)13-18(24(29)32)28(34)14-20(36-2)17-12-22(29)30(28,35)25(17)38-4/h6-9,17-18,20-25,34-35H,5,10-15,31H2,1-4H3/t17-,18+,20+,21?,22?,23+,24?,25+,27-,28+,29+,30+/m1/s1

InChI Key

VSUODASNSRJNCP-WUOZJDCCSA-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 barbatum	LOTUS Database	35616633
Aconitum leucostomum	LOTUS Database	35616633
Aconitum orientale	LOTUS Database	35616633
Aconitum septentrionale	LOTUS Database	35616633
Aconitum sinomontanum	LOTUS Database	35616633
Delphinium cashmerianum	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
Aminobenzoic acid or derivatives
Alkaloid or derivatives
Benzoic acid or derivatives
Aniline or substituted anilines
Benzoyl
Azepane
Benzenoid
Piperidine
Monocyclic benzene moiety
Vinylogous amide
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
1,2-diol
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
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	1.21	ChemAxon
pKa (Strongest Acidic)	12.51	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	123.71 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	143.93 m³·mol⁻¹	ChemAxon
Polarizability	58.21 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

C00028652

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

139292110

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bello-Ramirez AM, Nava-Ocampo AA: A QSAR analysis of toxicity of Aconitum alkaloids. Fundam Clin Pharmacol. 2004 Dec;18(6):699-704. doi: 10.1111/j.1472-8206.2004.00280.x. [PubMed:15548242 ]
Nie J, Wang F, Ji T, Zhao J, Zhao F: Assessment of in vitro cardiotoxicity of extract fractions and diterpene alkaloids from Aconitum leucostomum Worosch: A short communication. J Pharm Biomed Anal. 2017 Apr 15;137:84-89. doi: 10.1016/j.jpba.2017.01.003. Epub 2017 Jan 3. [PubMed:28104561 ]
Taber DF, Liang JL, Chen B, Cai L: A model study toward the total synthesis of N-deacetyllappaconitine. J Org Chem. 2005 Oct 28;70(22):8739-42. doi: 10.1021/jo051155y. [PubMed:16238304 ]
Tsorin IB, Teplov IY, Zinchenko VP, Vititnova MB, Tsyrlina EM, Yunusov MS, Kryzhanovskii SA: Analysis of Electrophysiological Mechanisms of N-Deacetyllapaconitine Monochlorhydrate, the Main Metabolite of Lappaconitine Hydrobromide. Bull Exp Biol Med. 2022 Jun;173(2):219-223. doi: 10.1007/s10517-022-05522-2. Epub 2022 Jun 24. [PubMed:35739330 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate (NP0256100)

MOL for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

3D MOL for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

3D SDF for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

3D-SDF for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

PDB for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

3D PDB for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

SMILES for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

INCHI for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

Structure for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)

3D Structure for NP0256100 ((1s,3s,4s,5r,6s,8s,9s,13s,16s)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl 2-aminobenzoate)