NP-MRD: Showing NP-Card for (1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0141359)

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Record Information

Version

1.0

Created at

2022-09-01 19:25:42 UTC

Updated at

2022-09-01 19:25:42 UTC

NP-MRD ID

NP0141359

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate

Description

Indaconitine belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. (1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate is found in Aconitum balfourii, Aconitum chasmanthum, Aconitum transsectum and Aconitum violaceum. It was first documented in 2020 (PMID: 33031866). Based on a literature review a significant number of articles have been published on Indaconitine (PMID: 35662724) (PMID: 35222676) (PMID: 34581046) (PMID: 34225245).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309012221252D          

 45 51  0  0  1  0            999 V2000
   -1.5611   -3.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834   -2.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6275   -1.5697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    0.3484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1463    1.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448    2.0069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691    2.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3864    0.3404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1461   -1.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610   -1.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -1.0270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0108   -1.0264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0942   -0.0351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7844   -0.4896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1088   -1.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068   -2.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -0.4558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6639   -1.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8888    0.5185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5896    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.6359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3105    1.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425   -0.1538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8414   -0.2564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3507   -0.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4107   -0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.7502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6866   -1.6281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2629   -2.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0677   -2.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175   -3.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822    0.0658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0347    0.8560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9847    1.7465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4654    2.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927    3.2188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892    2.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    3.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    3.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367    2.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4857    1.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6619    1.7016    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
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 13 10  1  1  0  0  0
 13 14  1  0  0  0  0
 14  3  1  1  0  0  0
 15 14  1  1  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  6  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 22  1  6  0  0  0
 35 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
M  END


  Mrv1652309012221252D          

 45 51  0  0  1  0            999 V2000
   -1.5611   -3.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834   -2.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6275   -1.5697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3448   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638    0.3484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1463    1.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5448    2.0069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3691    2.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3864    0.3404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2884   -0.6284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1461   -1.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610   -1.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -1.0270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0108   -1.0264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0942   -0.0351    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7844   -0.4896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1088   -1.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068   -2.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6710    0.1158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8572   -0.4558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6639   -1.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8888    0.5185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5896    1.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341    0.6359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3105    1.0154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9425   -0.1538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8414   -0.2564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3507   -0.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4107   -0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -0.7502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6866   -1.6281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2629   -2.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0677   -2.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175   -3.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822    0.0658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0347    0.8560    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9847    1.7465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4654    2.4828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0927    3.2188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892    2.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    3.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    3.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9367    2.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4857    1.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6619    1.7016    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
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 13 10  1  1  0  0  0
 13 14  1  0  0  0  0
 14  3  1  1  0  0  0
 15 14  1  1  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  6  0  0  0
 15 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 30 35  1  0  0  0  0
 35 22  1  6  0  0  0
 35 36  1  0  0  0  0
 24 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 40 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0141359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(COC)[C@H]3[C@@H](OC)[C@H]4[C@@H]1[C@@]3([C@@H]1C[C@@]3(O)[C@H](OC(=O)C5=CC=CC=C5)[C@@H]1[C@@]4(C[C@@H]3OC)OC(C)=O)[C@H](C[C@H]2O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C34H47NO10/c1-7-35-16-31(17-40-3)21(37)13-22(41-4)34-20-14-32(39)23(42-5)15-33(45-18(2)36,25(28(34)35)26(43-6)27(31)34)24(20)29(32)44-30(38)19-11-9-8-10-12-19/h8-12,20-29,37,39H,7,13-17H2,1-6H3/t20-,21-,22+,23+,24-,25+,26+,27-,28-,29-,31+,32+,33-,34+/m1/s1

> <INCHI_KEY>
PHDZNMWTZQPAEW-IOZYTHHVSA-N

> <FORMULA>
C34H47NO10

> <MOLECULAR_WEIGHT>
629.747

> <EXACT_MASS>
629.319996717

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
67.81509329768375

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4R,5S,6S,8R,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
0.14707429399999986

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.504677074617657

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.853312441962245

> <JCHEM_PKA_STRONGEST_BASIC>
10.054929722857114

> <JCHEM_POLAR_SURFACE_AREA>
133.22000000000003

> <JCHEM_REFRACTIVITY>
160.70759999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4R,5S,6S,8R,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-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                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.914  -5.836   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.649  -4.751   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.171  -2.930   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -2.510  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.359   0.650   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.140   2.333   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.884   3.746   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.422   3.806   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.721   0.635   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.538  -1.173   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.139  -2.030   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.847  -1.982   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.225  -1.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.020  -1.916   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.176  -0.066   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.464  -0.914   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.070  -2.882   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.573  -3.949   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.119   0.216   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.467  -0.851   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.973  -2.055   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.659   0.968   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.967   2.178   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.730   1.187   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.180   1.895   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.493  -0.287   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.171  -0.479   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.121  -1.759   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.500  -1.549   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.890  -1.400   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.148  -3.039   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.224  -4.205   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.726  -3.866   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.766  -5.675   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.767   0.123   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.798   1.598   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.705   3.260   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.602   4.634   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.906   6.008   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       6.140   4.550   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.982   5.840   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.519   5.755   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.215   4.381   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.373   3.092   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.836   3.176   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   20                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   15                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   30                                                  
CONECT   14   13    3   15                                                  
CONECT   15   14    9   16   22                                             
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19    5   21                                                  
CONECT   21   20                                                            
CONECT   22   15   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26   36                                             
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   13   31   35                                             
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   22   36                                                  
CONECT   36   35   24   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   40                                                       
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₄₇NO₁₀

Average Mass

629.7470 Da

Monoisotopic Mass

629.32000 Da

IUPAC Name

(1S,2R,3R,4R,5S,6S,8R,9R,10R,13R,14R,16S,17S,18R)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(COC)[C@H]3[C@@H](OC)[C@H]4[C@@H]1[C@@]3([C@@H]1C[C@@]3(O)[C@H](OC(=O)C5=CC=CC=C5)[C@@H]1[C@@]4(C[C@@H]3OC)OC(C)=O)[C@H](C[C@H]2O)OC

InChI Identifier

InChI=1S/C34H47NO10/c1-7-35-16-31(17-40-3)21(37)13-22(41-4)34-20-14-32(39)23(42-5)15-33(45-18(2)36,25(28(34)35)26(43-6)27(31)34)24(20)29(32)44-30(38)19-11-9-8-10-12-19/h8-12,20-29,37,39H,7,13-17H2,1-6H3/t20-,21-,22+,23+,24-,25+,26+,27-,28-,29-,31+,32+,33-,34+/m1/s1

InChI Key

PHDZNMWTZQPAEW-IOZYTHHVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum balfourii	LOTUS Database	35616633
Aconitum chasmanthum	LOTUS Database	35616633
Aconitum transsectum	LOTUS Database	35616633
Aconitum violaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Benzoate ester
Quinolidine
Benzoic acid or derivatives
Alkaloid or derivatives
Benzoyl
Azepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Piperidine
Cyclic alcohol
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Organic oxide
Amine
Carbonyl group
Alcohol
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Terpenoid alkaloids (C08691 )

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	2.18	ALOGPS
logP	0.15	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	10.05	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	11	ChemAxon
Refractivity	160.71 m³·mol⁻¹	ChemAxon
Polarizability	67.82 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

C00001647

Chemspider ID

34991047

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60208143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen ZY, Wei XY, Qiu ZD, Huang Y, Tan T, Feng YL, Guo J, Cui GH, Huang LQ, Lai CJ: Compatibility of Fuzi and Ginseng Significantly Increase the Exposure of Aconitines. Front Pharmacol. 2022 Apr 26;13:883898. doi: 10.3389/fphar.2022.883898. eCollection 2022. [PubMed:35662724 ]
Wang Y, Tao P, Wang YJ: Attenuated Structural Transformation of Indaconitine during Sand Frying Process and Anti-Arrhythmic Effects of Its Transformed Products. Evid Based Complement Alternat Med. 2022 Feb 17;2022:8606459. doi: 10.1155/2022/8606459. eCollection 2022. [PubMed:35222676 ]
Xie CY, Huang S, Chen L, Gao F, Zhou XL: [Diterpenoid alkaloids from roots of Aconitum kongboense]. Zhongguo Zhong Yao Za Zhi. 2021 Sep;46(17):4424-4432. doi: 10.19540/j.cnki.cjcmm.20210622.201. [PubMed:34581046 ]
Yu X, Liu H, Xu X, Hu Y, Wang X, Wen C: Pharmacokinetics of yunaconitine and indaconitine in mouse blood by UPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Aug 1;1179:122840. doi: 10.1016/j.jchromb.2021.122840. Epub 2021 Jun 19. [PubMed:34225245 ]
Si Y, Ding X, Adelakuna TA, Zhang Y, Hao XJ: Acotarines A-G, new diterpenoid alkaloids from Aconitum taronense induce lysosomal biogenesis. Fitoterapia. 2020 Nov;147:104738. doi: 10.1016/j.fitote.2020.104738. Epub 2020 Oct 5. [PubMed:33031866 ]

Showing NP-Card for (1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0141359)

MOL for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D MOL for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D SDF for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D-SDF for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

PDB for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D PDB for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

SMILES for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

INCHI for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

Structure for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D Structure for NP0141359 ((1s,2r,3r,4r,5s,6s,8r,9r,10r,13r,14r,16s,17s,18r)-8-(acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)