NP-MRD: Showing NP-Card for n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid (NP0220243)

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Record Information

Version

2.0

Created at

2022-09-05 21:29:56 UTC

Updated at

2022-09-05 21:29:56 UTC

NP-MRD ID

NP0220243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid

Description

Ranaconitine 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. n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid is found in Aconitum laeve. n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid was first documented in 2006 (PMID: 16931429). Based on a literature review a significant number of articles have been published on Ranaconitine (PMID: 31927015) (PMID: 35469829) (PMID: 35424499) (PMID: 28104561) (PMID: 32563055) (PMID: 29461247).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223292D          

 43 49  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
   -3.1092   -1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720   -0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823   -1.4142    0.0000 O   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
    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  1  0  0  0  0  0  0  0  0  0
    0.4081   -1.2240    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
    1.3250    0.0210    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2937    0.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.1786    0.0000 C   0  0  1  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  2  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
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29  3  1  6  0  0  0
 24 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  1  0  0  0
 24 38  1  0  0  0  0
 38 39  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  1  0  0  0  0
M  END


  Mrv1652309052223292D          

 43 49  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
   -3.1092   -1.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9720   -0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823   -1.4142    0.0000 O   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
    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  1  0  0  0  0  0  0  0  0  0
    0.4081   -1.2240    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
    1.3250    0.0210    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2937    0.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7487   -0.1786    0.0000 C   0  0  1  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  2  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
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29  3  1  6  0  0  0
 24 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  1  0  0  0
 38 37  1  1  0  0  0
 24 38  1  0  0  0  0
 38 39  1  0  0  0  0
 30 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@@](O)(C[C@H]23)[C@@H]14)OC(=O)C1=CC=CC=C1N=C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C32H44N2O9/c1-6-34-16-28(43-26(36)18-9-7-8-10-20(18)33-17(2)35)12-11-24(41-4)31-22-13-19-21(40-3)14-30(38,32(22,39)25(19)42-5)29(37,27(31)34)15-23(28)31/h7-10,19,21-25,27,37-39H,6,11-16H2,1-5H3,(H,33,35)/t19-,21+,22+,23-,24+,25+,27-,28-,29-,30+,31-,32+/m1/s1

> <INCHI_KEY>
XTSVKUJYTUPYRJ-FUIAWOLXSA-N

> <FORMULA>
C32H44N2O9

> <MOLECULAR_WEIGHT>
600.709

> <EXACT_MASS>
600.304681005

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
63.5522025536377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[2-({[(1S,2S,3S,4S,5R,6S,8S,9R,10S,13S,16S,17S)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid

> <JCHEM_LOGP>
-2.0986022893025806

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.132196226810391

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.2692641384996515

> <JCHEM_PKA_STRONGEST_BASIC>
8.637963846044824

> <JCHEM_POLAR_SURFACE_AREA>
150.51

> <JCHEM_REFRACTIVITY>
156.0856

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-({[(1S,2S,3S,4S,5R,6S,8S,9R,10S,13S,16S,17S)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-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      -5.804  -2.102   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.548  -0.584   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -7.247  -2.640   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.108  -4.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.394  -4.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.375  -3.764   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.877  -4.105   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.332  -5.576   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.981  -2.157   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       0.591  -0.598   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.473   0.039   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.415   1.578   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.398  -0.333   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.167  -0.394   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.170   1.146   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.687  -0.011   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.842  -1.104   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.335  -0.724   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.752   0.758   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.329  -2.683   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.801  -4.005   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.442  -2.953   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.324  -1.947   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       5.737  -1.336   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.528  -3.329   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.393  -4.863   0.000  0.00  0.00           O+0
HETATM   43  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   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19   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   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    5   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   29   38                                             
CONECT   25   24    5   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27    3   24                                                  
CONECT   30   27   31   32   39                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   24   39                                                  
CONECT   39   38   30   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   36   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₄N₂O₉

Average Mass

600.7090 Da

Monoisotopic Mass

600.30468 Da

IUPAC Name

N-[2-({[(1S,2S,3S,4S,5R,6S,8S,9R,10S,13S,16S,17S)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](OC)[C@]5(O)[C@](O)(C[C@@H]6OC)[C@@](O)(C[C@H]23)[C@@H]14)OC(=O)C1=CC=CC=C1N=C(C)O

InChI Identifier

InChI=1S/C32H44N2O9/c1-6-34-16-28(43-26(36)18-9-7-8-10-20(18)33-17(2)35)12-11-24(41-4)31-22-13-19-21(40-3)14-30(38,32(22,39)25(19)42-5)29(37,27(31)34)15-23(28)31/h7-10,19,21-25,27,37-39H,6,11-16H2,1-5H3,(H,33,35)/t19-,21+,22+,23-,24+,25+,27-,28-,29-,30+,31-,32+/m1/s1

InChI Key

XTSVKUJYTUPYRJ-FUIAWOLXSA-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 laeve	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
Acylaminobenzoic acid or derivatives
Acetanilide
Benzoate ester
Quinolidine
N-acetylarylamine
Benzoic acid or derivatives
Alkaloid or derivatives
Anilide
Benzoyl
N-arylamide
Azepane
Piperidine
Monocyclic benzene moiety
Benzenoid
Cyclic alcohol
Tertiary alcohol
Acetamide
Vinylogous amide
Carboxylic acid ester
Secondary carboxylic acid amide
Amino acid or derivatives
Tertiary amine
Tertiary aliphatic amine
Carboxamide group
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Dialkyl ether
Ether
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
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	-2.1	ChemAxon
pKa (Strongest Acidic)	5.27	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.51 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	156.09 m³·mol⁻¹	ChemAxon
Polarizability	63.55 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

62765432

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98055304

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jiang GY, Qin LL, Gao F, Huang S, Zhou XL: Fifteen new diterpenoid alkaloids from the roots of Aconitum kirinense Nakai. Fitoterapia. 2020 Mar;141:104477. doi: 10.1016/j.fitote.2020.104477. Epub 2020 Jan 10. [PubMed:31927015 ]
Zhang L, Miao X, Li Y, Hu F, Ma D, Zhang Z, Sun Q, Zhu Y, Zhu Q: Traditional processing, uses, phytochemistry, pharmacology and toxicology of Aconitum sinomontanum Nakai: A comprehensive review. J Ethnopharmacol. 2022 Jul 15;293:115317. doi: 10.1016/j.jep.2022.115317. Epub 2022 Apr 22. [PubMed:35469829 ]
Yan Y, Li X, Wang Z, Yang X, Yin T: C18-diterpenoid alkaloids in tribe Delphineae (Ranunculaceae): phytochemistry, chemotaxonomy, and bioactivities. RSC Adv. 2021 Dec 22;12(1):395-405. doi: 10.1039/d1ra08132b. eCollection 2021 Dec 20. [PubMed:35424499 ]
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 ]
Zhang L, Miao X, Li Y, Dai H, Shang X, Hu F, Fan Q: Toxic and active material basis of Aconitum sinomontanum Nakai based on biological activity guidance and UPLC-Q/TOF-MS technology. J Pharm Biomed Anal. 2020 Sep 5;188:113374. doi: 10.1016/j.jpba.2020.113374. Epub 2020 May 31. [PubMed:32563055 ]
Tan JJ, Tan CH, Ruan BQ, Jiang SH, Zhu DY: Two new 18-carbon norditerpenoid alkaloids from Aconitum sinomontanum. J Asian Nat Prod Res. 2006 Sep;8(6):535-9. doi: 10.1080/10286020500175643. [PubMed:16931429 ]
Kintsurashvili L, Mshvildadze V, Suladze T: [ALKALOIDS OF UNDERGROUND PARTS OF GEORGIAN FLORA'S ACONITUM ORIENTALE MILL. AND ACONITUM NASUTUM FISCH. EX REICHEMB AND THEIR BIOLOGICAL ACTIVITY]. Georgian Med News. 2018 Jan;(274):164-167. [PubMed:29461247 ]
Guo T, Zhang Y, Zhao J, Zhu C, Feng N: Nanostructured lipid carriers for percutaneous administration of alkaloids isolated from Aconitum sinomontanum. J Nanobiotechnology. 2015 Jul 10;13:47. doi: 10.1186/s12951-015-0107-3. [PubMed:26156035 ]
Li Y, Zhou JH, Han GJ, Wang MJ, Sun WJ, Zhao Y: X-ray crystallographic study of ranaconitine. Nat Prod Commun. 2011 Nov;6(11):1589-90. [PubMed:22224266 ]
Zhou JH, Li Y, Zhang L, Wang DQ: X-ray structure study of ranaconitine hydrobromide. Nat Prod Res. 2012;26(15):1451-3. doi: 10.1080/14786419.2011.603319. Epub 2011 Oct 11. [PubMed:21988549 ]
LOTUS database [Link]

Showing NP-Card for n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid (NP0220243)

MOL for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

3D MOL for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

3D SDF for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

3D-SDF for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

PDB for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

3D PDB for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

SMILES for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

INCHI for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

Structure for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)

3D Structure for NP0220243 (n-[2-({[(1s,2s,3s,4s,5r,6s,8s,9r,10s,13s,16s,17s)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-13-yl]oxy}carbonyl)phenyl]ethanimidic acid)