NP-MRD: Showing NP-Card for (1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0226911)

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Record Information

Version

2.0

Created at

2022-09-06 06:06:03 UTC

Updated at

2022-09-06 06:06:03 UTC

NP-MRD ID

NP0226911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate

Description

Pyroaconitine 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,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate was first documented in 2010 (PMID: 20506817). Based on a literature review a small amount of articles have been published on Pyroaconitine (PMID: 24452459) (PMID: 34733344).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062208062D          

 42 48  0  0  1  0            999 V2000
    3.0342    3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514    2.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    1.5110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    0.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.4071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2401   -1.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8936   -2.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -2.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988   -0.3991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0968    0.5698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2160    1.1725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3126    1.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    0.9683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9334    0.6915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7958    0.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127    1.5532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276    0.0952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2156    0.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7092    0.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.6945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6059   -1.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9747   -1.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2740   -0.5772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8674   -0.1245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4198   -0.9147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4354   -1.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623   -2.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -2.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4491   -3.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609   -3.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -4.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227   -4.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2109   -3.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -3.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -0.0235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6008    0.4310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1778    1.2722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7758    1.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -0.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5279    0.3971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8154    1.0772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    0.9677    0.0000 C   0  0  2  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  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 13 10  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 24 23  1  1  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 35 23  1  1  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  1  0  0  0
 35 42  1  0  0  0  0
 13 42  1  0  0  0  0
 42  3  1  6  0  0  0
M  END


  Mrv1652309062208062D          

 42 48  0  0  1  0            999 V2000
    3.0342    3.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514    2.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7576    1.5110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    0.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1213   -0.4071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2401   -1.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8936   -2.0787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -2.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9988   -0.3991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0968    0.5698    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2160    1.1725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3126    1.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0416    0.9683    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9334    0.6915    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7958    0.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127    1.5532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3276    0.0952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2156    0.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7092    0.8970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.6945    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6059   -1.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9747   -1.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2740   -0.5772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8674   -0.1245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4198   -0.9147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4354   -1.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623   -2.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6873   -2.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4491   -3.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8609   -3.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4477   -4.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227   -4.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2109   -3.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241   -3.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4793   -0.0235    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6008    0.4310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1778    1.2722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7758    1.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7141   -0.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5279    0.3971    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8154    1.0772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3960    0.9677    0.0000 C   0  0  2  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  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 13 10  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 24 23  1  1  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 35 23  1  1  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 36 39  1  0  0  0  0
 39 40  1  0  0  0  0
  5 40  1  0  0  0  0
 40 41  1  1  0  0  0
 35 42  1  0  0  0  0
 13 42  1  0  0  0  0
 42  3  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0226911

> <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@@H]4C(=O)[C@@H]3OC)[C@H](C[C@H]2O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H43NO9/c1-6-33-14-30(15-38-2)18(34)12-19(39-3)32-17-13-31(37)27(42-29(36)16-10-8-7-9-11-16)20(17)21(23(35)28(31)41-5)22(26(32)33)24(40-4)25(30)32/h7-11,17-22,24-28,34,37H,6,12-15H2,1-5H3/t17-,18-,19+,20+,21+,22+,24+,25-,26-,27-,28+,30+,31-,32+/m1/s1

> <INCHI_KEY>
RMTJALKWXOBAMX-BYJXHDAOSA-N

> <FORMULA>
C32H43NO9

> <MOLECULAR_WEIGHT>
585.694

> <EXACT_MASS>
585.293781969

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
62.358449584933716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3S,4R,5R,6R,8S,9R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

> <JCHEM_LOGP>
0.3837162996666661

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.368583872228804

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.662313283053507

> <JCHEM_PKA_STRONGEST_BASIC>
9.237420476798485

> <JCHEM_POLAR_SURFACE_AREA>
123.99000000000001

> <JCHEM_REFRACTIVITY>
150.86719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,4R,5R,6R,8S,9R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-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                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       5.664   6.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.136   4.662   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.148   2.821   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.809   1.023   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.960  -0.760   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.182  -2.431   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.535  -3.880   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.003  -4.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.598  -0.745   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.781   1.064   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.137   2.189   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.450   2.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.544   1.808   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.209   1.291   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.819   1.439   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.410   2.899   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.812   0.178   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.469   0.393   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.391   1.674   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.049  -1.296   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.331  -2.360   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.286  -2.288   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.978  -1.077   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.086  -0.232   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.117  -1.707   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.146  -3.349   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.943  -4.732   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.483  -4.734   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.172  -6.065   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.940  -7.399   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.169  -8.732   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.629  -8.731   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.860  -7.397   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.632  -6.064   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.495  -0.044   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.855   0.805   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.932   2.375   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.048   3.644   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.200  -0.326   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.852   0.741   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       1.522   2.011   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.339   1.806   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   40                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10   35                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   42                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22   25                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   35                                                  
CONECT   24   23   14   25                                                  
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   23    9   36   42                                             
CONECT   36   35   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   40                                                       
CONECT   40   39    5   41                                                  
CONECT   41   40                                                            
CONECT   42   35   13    3                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₃NO₉

Average Mass

585.6940 Da

Monoisotopic Mass

585.29378 Da

IUPAC Name

(1S,2R,3S,4R,5R,6R,8S,9R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl benzoate

Traditional Name

(1S,2R,3S,4R,5R,6R,8S,9R,10R,13R,14R,16S,17S,18R)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-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(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@@H]4C(=O)[C@@H]3OC)[C@H](C[C@H]2O)OC

InChI Identifier

InChI=1S/C32H43NO9/c1-6-33-14-30(15-38-2)18(34)12-19(39-3)32-17-13-31(37)27(42-29(36)16-10-8-7-9-11-16)20(17)21(23(35)28(31)41-5)22(26(32)33)24(40-4)25(30)32/h7-11,17-22,24-28,34,37H,6,12-15H2,1-5H3/t17-,18-,19+,20+,21+,22+,24+,25-,26-,27-,28+,30+,31-,32+/m1/s1

InChI Key

RMTJALKWXOBAMX-BYJXHDAOSA-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

Not Available

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
Quinolidine
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Benzoyl
Azepane
Benzenoid
Piperidine
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ketone
Carboxylic acid ester
Amino acid or derivatives
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
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	0.38	ChemAxon
pKa (Strongest Acidic)	12.66	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	123.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	150.87 m³·mol⁻¹	ChemAxon
Polarizability	62.36 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

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

101425662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Borcsa B, Fodor L, Csupor D, Forgo P, Molnar A 5th, Hohmann J: Diterpene alkaloids from the roots of Aconitum moldavicum and assessment of Nav 1.2 sodium channel activity of aconitum alkaloids. Planta Med. 2014 Feb;80(2-3):231-6. doi: 10.1055/s-0033-1360278. Epub 2014 Jan 22. [PubMed:24452459 ]
Wang YJ, Tao P, Wang Y: Attenuated Structural Transformation of Aconitine during Sand Frying Process and Antiarrhythmic Effect of Its Converted Products. Evid Based Complement Alternat Med. 2021 Oct 25;2021:7243052. doi: 10.1155/2021/7243052. eCollection 2021. [PubMed:34733344 ]
Wang Y, Zhang J, Tian H, Zeng C, Yao Z, Zhang Y: [Study on processing principle of Aconitum pendulum]. Zhongguo Zhong Yao Za Zhi. 2010 Mar;35(5):588-92. doi: 10.4268/cjcmm20100510. [PubMed:20506817 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0226911)

MOL for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D MOL for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D SDF for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D-SDF for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

PDB for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D PDB for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

SMILES for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

INCHI for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

Structure for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D Structure for NP0226911 ((1s,2r,3s,4r,5r,6r,8s,9r,10r,13r,14r,16s,17s,18r)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-7-oxo-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)