NP-MRD: Showing NP-Card for (1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl 4-methoxybenzoate (NP0266925)

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Record Information

Version

2.0

Created at

2022-09-08 11:32:04 UTC

Updated at

2022-09-08 11:32:04 UTC

NP-MRD ID

NP0266925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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

8-Deacetylyunaconitine 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,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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. (1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl 4-methoxybenzoate was first documented in 2013 (PMID: 23784883). Based on a literature review very few articles have been published on 8-Deacetylyunaconitine (PMID: 34814080).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082213322D          

 44 50  0  0  1  0            999 V2000
   -0.4129   -3.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397   -2.5440    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
   -1.1349    1.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    2.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    2.1023    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  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.2324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1635   -1.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -1.0270    0.0000 C   0  0  0  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
   -0.7881   -1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0272   -1.8750    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
   -2.6892   -1.0891    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
    3.2567    1.1105    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
    3.8323   -0.2603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.9956    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
    1.6710   -1.6034    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
    2.0417    1.7424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016    2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131    3.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    2.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7622    3.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5867    3.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    2.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998    2.3714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1883    1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392    1.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    1.7259    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  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  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
 30 32  1  0  0  0  0
 32 22  1  6  0  0  0
 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  2  0  0  0  0
 37 44  1  0  0  0  0
M  END


  Mrv1652309082213322D          

 44 50  0  0  1  0            999 V2000
   -0.4129   -3.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6397   -2.5440    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
   -1.1349    1.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784    2.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    2.1023    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  0  0  0  0  0  0  0  0  0  0
   -1.2726   -1.2324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1635   -1.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564   -1.0270    0.0000 C   0  0  0  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
   -0.7881   -1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0272   -1.8750    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
   -2.6892   -1.0891    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
    3.2567    1.1105    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
    3.8323   -0.2603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2600   -0.9956    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
    1.6710   -1.6034    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
    2.0417    1.7424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016    2.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131    3.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261    2.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7622    3.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5867    3.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9752    2.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998    2.3714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1883    1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392    1.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    1.7259    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  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  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
 30 32  1  0  0  0  0
 32 22  1  6  0  0  0
 32 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  2  0  0  0  0
 37 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(COC)[C@H]3C(OC)C4[C@@H]1[C@@]3([C@@H]1C[C@@]3(O)[C@H](OC(=O)C5=CC=C(OC)C=C5)[C@@H]1[C@]4(O)C[C@@H]3OC)[C@H](C[C@H]2O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C33H47NO10/c1-7-34-15-30(16-39-2)20(35)12-21(41-4)33-19-13-31(37)22(42-5)14-32(38,24(27(33)34)25(43-6)26(30)33)23(19)28(31)44-29(36)17-8-10-18(40-3)11-9-17/h8-11,19-28,35,37-38H,7,12-16H2,1-6H3/t19-,20-,21+,22+,23-,24?,25?,26-,27-,28-,30+,31+,32-,33+/m1/s1

> <INCHI_KEY>
DHVYLCVNTWPXSI-HIUSHPNESA-N

> <FORMULA>
C33H47NO10

> <MOLECULAR_WEIGHT>
617.736

> <EXACT_MASS>
617.319996717

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
66.90061848139996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4R,5S,6S,8R,10R,13R,14R,16S,17S)-11-ethyl-5,8,14-trihydroxy-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 4-methoxybenzoate

> <JCHEM_LOGP>
-0.45172238200000203

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.943930019789644

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.825309108329286

> <JCHEM_PKA_STRONGEST_BASIC>
9.781664185204223

> <JCHEM_POLAR_SURFACE_AREA>
136.38

> <JCHEM_REFRACTIVITY>
158.0192999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4R,5S,6S,8R,10R,13R,14R,16S,17S)-11-ethyl-5,8,14-trihydroxy-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 4-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.771  -6.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.194  -4.749   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      -2.118   2.312   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.760   3.760   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.291   3.924   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      -2.376  -2.301   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.038  -2.093   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      -1.471  -2.283   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.051  -3.500   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      -5.020  -2.033   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       6.079   2.073   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       7.154  -0.486   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.952  -1.858   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       3.119  -2.993   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.767   0.123   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.798   1.598   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.811   3.252   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.670   4.631   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.944   5.990   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.209   4.580   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.023   5.888   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.562   5.836   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.287   4.478   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.826   4.427   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      11.551   3.068   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.473   3.171   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.934   3.222   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   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26   33                                             
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   13   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   22   33                                                  
CONECT   33   32   24   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   44                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44                                                       
CONECT   44   43   37                                                       
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₇NO₁₀

Average Mass

617.7360 Da

Monoisotopic Mass

617.32000 Da

IUPAC Name

(1S,2R,3R,4R,5S,6S,8R,10R,13R,14R,16S,17S)-11-ethyl-5,8,14-trihydroxy-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 4-methoxybenzoate

Traditional Name

(1S,2R,3R,4R,5S,6S,8R,10R,13R,14R,16S,17S)-11-ethyl-5,8,14-trihydroxy-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 4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(COC)[C@H]3C(OC)C4[C@@H]1[C@@]3([C@@H]1C[C@@]3(O)[C@H](OC(=O)C5=CC=C(OC)C=C5)[C@@H]1[C@]4(O)C[C@@H]3OC)[C@H](C[C@H]2O)OC

InChI Identifier

InChI=1S/C33H47NO10/c1-7-34-15-30(16-39-2)20(35)12-21(41-4)33-19-13-31(37)22(42-5)14-32(38,24(27(33)34)25(43-6)26(30)33)23(19)28(31)44-29(36)17-8-10-18(40-3)11-9-17/h8-11,19-28,35,37-38H,7,12-16H2,1-6H3/t19-,20-,21+,22+,23-,24?,25?,26-,27-,28-,30+,31+,32-,33+/m1/s1

InChI Key

DHVYLCVNTWPXSI-HIUSHPNESA-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

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
Quinolidine
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Anisole
Azepane
Alkyl aryl ether
Benzenoid
Piperidine
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Polyol
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
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	-0.45	ChemAxon
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	136.38 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	158.02 m³·mol⁻¹	ChemAxon
Polarizability	66.9 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

113606339

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

137706281

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang YF, He F, Cui H, Zhang YY, Yang HY, Liang ZS, Dai W, Cheng CS, Xie Y, Liu L, Liu ZQ, Zhou H: Systematic investigation on the distribution of four hidden toxic Aconitum alkaloids in commonly used Aconitum herbs and their acute toxicity. J Pharm Biomed Anal. 2022 Jan 20;208:114471. doi: 10.1016/j.jpba.2021.114471. Epub 2021 Nov 16. [PubMed:34814080 ]
Shu XK, Li J, Liu F, Lin XJ, Wang X, Song CX: Accelerated solvent extraction and pH-zone-refining counter-current chromatographic purification of yunaconitine and 8-deacetylyunaconitine from Aconitum vilmorinianum Kom. J Sep Sci. 2013 Aug;36(16):2680-5. doi: 10.1002/jssc.201300472. Epub 2013 Jul 19. [PubMed:23784883 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl 4-methoxybenzoate (NP0266925)

MOL for NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-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 NP0266925 ((1s,2r,3r,4r,5s,6s,8r,10r,13r,14r,16s,17s)-11-ethyl-5,8,14-trihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl 4-methoxybenzoate)