NP-MRD: Showing NP-Card for 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 4-methoxybenzoate (NP0223789)

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Record Information

Version

2.0

Created at

2022-09-06 01:58:52 UTC

Updated at

2022-09-06 01:58:52 UTC

NP-MRD ID

NP0223789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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 4-methoxybenzoate

Description

Yunaconitine 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. 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 4-methoxybenzoate is found in Aconitum balfourii, Aconitum bulleyanum, Aconitum forrestii, Aconitum hemsleyanum, Aconitum kusnezoffii, Aconitum nagarum, Aconitum piepunense, Aconitum sungpanense and Aconitum transsectum. Yunaconitine is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241519492D          

 47 53  0  0  0  0            999 V2000
   -0.2168    1.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5115    0.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -2.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651   -1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -0.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448   -0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -0.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3846   -1.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9548   -1.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3785   -2.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240   -2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -2.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1238   -3.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8381   -4.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8379   -4.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1234   -5.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090   -4.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -4.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -6.2297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086   -6.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -0.2840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9971    0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866    0.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959    1.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1647    2.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536    0.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468    0.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407   -3.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -3.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -3.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645   -1.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -1.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -1.0555    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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
  3 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 33  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  8 42  1  0  0  0  0
 42 43  1  0  0  0  0
  6 44  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END


  Mrv1533004241519492D          

 47 53  0  0  0  0            999 V2000
   -0.2168    1.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5115    0.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -0.0965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6588   -0.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975   -1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658   -2.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -2.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2651   -1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -1.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4024   -1.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -0.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3214    0.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448   -0.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -0.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6610   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3846   -1.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5644   -2.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378   -1.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9548   -1.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3785   -2.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240   -2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -2.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1238   -3.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8381   -4.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8379   -4.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1234   -5.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090   -4.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092   -4.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232   -6.2297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4086   -6.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5215   -0.2840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9971    0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866    0.7411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5959    1.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1647    2.1987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206    1.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5536    0.1847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468    0.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3407   -3.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -3.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -3.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645   -1.9454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0281   -1.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -1.0555    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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
  3 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 33  1  0  0  0  0
 16 34  1  0  0  0  0
 34 35  1  0  0  0  0
 14 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
  8 42  1  0  0  0  0
 42 43  1  0  0  0  0
  6 44  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223789

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1CC2(COC)C3C(OC)C4C1C3(C1CC3(O)C(OC(=O)C5=CC=C(OC)C=C5)C1C4(CC3OC)OC(C)=O)C(CC2O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C35H49NO11/c1-8-36-16-32(17-41-3)22(38)13-23(43-5)35-21-14-33(40)24(44-6)15-34(47-18(2)37,26(29(35)36)27(45-7)28(32)35)25(21)30(33)46-31(39)19-9-11-20(42-4)12-10-19/h9-12,21-30,38,40H,8,13-17H2,1-7H3

> <INCHI_KEY>
LLEMSCWAKNQHHA-UHFFFAOYSA-N

> <FORMULA>
C35H49NO11

> <MOLECULAR_WEIGHT>
659.773

> <EXACT_MASS>
659.330561402

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.02521398176135

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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 4-methoxybenzoate

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
-0.010596971666667815

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.504677074615767

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.853312441881297

> <JCHEM_PKA_STRONGEST_BASIC>
10.054929722856984

> <JCHEM_POLAR_SURFACE_AREA>
142.45

> <JCHEM_REFRACTIVITY>
167.17079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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 4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.405   3.103   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.955   1.583   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.182  -0.180   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.230  -1.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.555  -2.953   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.123  -4.494   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.379  -4.926   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.361  -3.733   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.970  -2.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.751  -2.251   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.584  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.467   0.070   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.390  -0.301   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.160  -0.366   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.680   0.015   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.834  -1.081   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.318  -2.659   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787  -3.979   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.431  -2.924   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.314  -1.920   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.516  -3.304   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.307  -4.665   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.698  -5.469   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.032  -4.699   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.698  -7.009   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.031  -7.779   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.031  -9.319   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.697 -10.089   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.363  -9.318   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.364  -7.778   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.697 -11.629   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.363 -12.398   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.892  -3.370   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       8.440  -0.530   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.328   0.800   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.082   1.383   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.846   2.791   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.041   4.104   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.385   2.832   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.033   0.345   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -2.701   0.522   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.503  -5.644   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.202  -7.112   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.997  -5.942   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.174  -3.631   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -3.786  -3.400   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -4.358  -1.970   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   45                                             
CONECT    6    5    7   44                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   42                                                  
CONECT    9    8   10   13   19                                             
CONECT   10    9    5   11                                                  
CONECT   11   10   12   40                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    9    3                                                  
CONECT   14   12   15   20   36                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16   18   21   33                                             
CONECT   18   17   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20   17   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28   32                                                       
CONECT   32   31                                                            
CONECT   33   17                                                            
CONECT   34   16   35                                                       
CONECT   35   34                                                            
CONECT   36   14   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   11   41                                                       
CONECT   41   40                                                            
CONECT   42    8   43                                                       
CONECT   43   42                                                            
CONECT   44    6                                                            
CONECT   45    5   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  106    0
END

View in JSmol

Synonyms

Value	Source
Isoaconitine	MeSH
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 4-methoxybenzoic acid	Generator
8-(Acetyloxy)-11-ethyl-5,14-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-4-yl 4-methoxybenzoic acid	Generator

Chemical Formula

C₃₅H₄₉NO₁₁

Average Mass

659.7730 Da

Monoisotopic Mass

659.33056 Da

IUPAC Name

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 4-methoxybenzoate

Traditional Name

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 4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

CCN1CC2(COC)C3C(OC)C4C1C3(C1CC3(O)C(OC(=O)C5=CC=C(OC)C=C5)C1C4(CC3OC)OC(C)=O)C(CC2O)OC

InChI Identifier

InChI=1S/C35H49NO11/c1-8-36-16-32(17-41-3)22(38)13-23(43-5)35-21-14-33(40)24(44-6)15-34(47-18(2)37,26(29(35)36)27(45-7)28(32)35)25(21)30(33)46-31(39)19-9-11-20(42-4)12-10-19/h9-12,21-30,38,40H,8,13-17H2,1-7H3

InChI Key

LLEMSCWAKNQHHA-UHFFFAOYSA-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 balfourii	LOTUS Database	35616633
Aconitum bulleyanum	LOTUS Database	35616633
Aconitum forrestii	LOTUS Database	35616633
Aconitum hemsleyanum	LOTUS Database	35616633
Aconitum kusnezoffii	LOTUS Database	35616633
Aconitum nagarum	LOTUS Database	35616633
Aconitum piepunense	LOTUS Database	35616633
Aconitum sungpanense	LOTUS Database	35616633
Aconitum transsectum	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
P-methoxybenzoic acid or derivatives
Benzoate ester
Quinolidine
Benzoic acid or derivatives
Alkaloid or derivatives
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
Azepane
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Piperidine
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Tertiary amine
Organoheterocyclic compound
Ether
Dialkyl ether
Azacycle
Carboxylic acid derivative
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organonitrogen compound
Alcohol
Organooxygen compound
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	2.23	ALOGPS
logP	-0.011	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	10.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	142.45 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	167.17 m³·mol⁻¹	ChemAxon
Polarizability	70.03 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

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

155569

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 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 4-methoxybenzoate (NP0223789)

MOL for NP0223789 (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 4-methoxybenzoate)

3D MOL for NP0223789 (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 4-methoxybenzoate)

3D SDF for NP0223789 (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 4-methoxybenzoate)

3D-SDF for NP0223789 (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 4-methoxybenzoate)

PDB for NP0223789 (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 4-methoxybenzoate)

3D PDB for NP0223789 (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 4-methoxybenzoate)

SMILES for NP0223789 (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 4-methoxybenzoate)

INCHI for NP0223789 (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 4-methoxybenzoate)

Structure for NP0223789 (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 4-methoxybenzoate)

3D Structure for NP0223789 (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 4-methoxybenzoate)