NP-MRD: Showing NP-Card for (1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0230806)

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Record Information

Version

2.0

Created at

2022-09-06 11:22:51 UTC

Updated at

2022-09-06 11:22:51 UTC

NP-MRD ID

NP0230806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Delphinine 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,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate is found in Clematis sibirica and Consolida hellespontica. (1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate was first documented in 2018 (PMID: 29932096). Based on a literature review very few articles have been published on Delphinine (PMID: 30915419).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062213222D          

 43 49  0  0  1  0            999 V2000
   -0.6323   -1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6828   -1.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0329   -0.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9331   -0.5608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6335   -1.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1830   -1.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0144   -1.7557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8169   -2.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8276   -3.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -0.9215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5216    0.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217    0.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556    0.1910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3497    1.0422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4746    1.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
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 11 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
  4 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062213222D          

 43 49  0  0  1  0            999 V2000
   -0.6323   -1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6335   -1.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1830   -1.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0144   -1.7557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8169   -2.6252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8276   -3.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -0.9215    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5216    0.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217    0.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556    0.1910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3497    1.0422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4746    1.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -0.6538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9006   -0.4090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1087    0.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5712    1.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5263    0.7899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7565   -0.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1983   -1.1652    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0883   -1.1209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7431   -0.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7055   -1.9068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3643   -2.4669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7061   -2.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0980   -1.5792    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7350   -1.2231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1848   -2.0742    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2561   -2.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288   -3.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4509   -3.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -4.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5093   -5.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386   -5.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2165   -5.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8651   -5.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359   -4.3411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7437    0.6736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2197    1.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9904    0.2804    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
  4  3  1  6  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  1  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 16 13  1  1  0  0  0
  4 16  1  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 29 28  1  1  0  0  0
 10 29  1  0  0  0  0
 30 29  1  1  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 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
 35 40  1  0  0  0  0
 11 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
  4 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0230806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@@]12CC[C@H](OC)[C@@]34[C@@H]5C[C@@]6(O)[C@H](OC(=O)C7=CC=CC=C7)[C@@H]5[C@@](C[C@@H]6OC)(OC(C)=O)C([C@H](OC)[C@H]13)C4N(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24?,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1

> <INCHI_KEY>
REVYTWNGZDPRKE-DBMGXYMYSA-N

> <FORMULA>
C33H45NO9

> <MOLECULAR_WEIGHT>
599.721

> <EXACT_MASS>
599.309432033

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.66007875138132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.0938714123333309

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.863595191645889

> <JCHEM_PKA_STRONGEST_BASIC>
10.198317290800727

> <JCHEM_POLAR_SURFACE_AREA>
112.99

> <JCHEM_REFRACTIVITY>
154.4870999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4R,5S,6S,8R,13S,16S,17R,18R)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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      -1.180  -3.411   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.274  -1.874   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.061  -0.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.742  -1.047   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.182  -2.514   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.208  -3.691   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.760  -3.277   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.391  -4.900   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.412  -6.514   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.441  -1.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.707   0.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.827   0.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.837   0.357   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.519   1.945   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.886   2.354   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.274  -1.220   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.281  -0.763   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.670   0.890   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.852   1.952   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.533   3.458   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.316   1.474   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.879  -0.817   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.703  -2.175   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.365  -2.092   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.587  -1.010   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.784  -3.559   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.013  -4.605   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.918  -4.339   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.783  -2.948   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.972  -2.283   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.812  -3.872   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.945  -5.490   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.640  -6.967   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.175  -7.096   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.762  -8.232   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.417  -9.625   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.539 -10.890   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.004 -10.761   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.348  -9.368   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.227  -8.103   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0       3.255   1.257   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0       4.143   2.663   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.849   0.523   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16   43                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   16   29                                             
CONECT   11   10   12   41                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    4   10                                                  
CONECT   17   12   18   22   30                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28   31                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   10   30                                                  
CONECT   30   29   17   31                                                  
CONECT   31   30   26   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   11   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    4                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₅NO₉

Average Mass

599.7210 Da

Monoisotopic Mass

599.30943 Da

IUPAC Name

(1S,2R,3R,4R,5S,6S,8R,13S,16S,17R,18R)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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,3R,4R,5S,6S,8R,13S,16S,17R,18R)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-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

COC[C@@]12CC[C@H](OC)[C@@]34[C@@H]5C[C@@]6(O)[C@H](OC(=O)C7=CC=CC=C7)[C@@H]5[C@@](C[C@@H]6OC)(OC(C)=O)C([C@H](OC)[C@H]13)C4N(C)C2

InChI Identifier

InChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24?,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1

InChI Key

REVYTWNGZDPRKE-DBMGXYMYSA-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
Clematis sibirica	LOTUS Database	35616633
Consolida hellespontica	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
Quinolidine
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Benzoyl
Azepane
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
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	1.09	ChemAxon
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	154.49 m³·mol⁻¹	ChemAxon
Polarizability	64.66 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

C00001613

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Delphinine

METLIN ID

Not Available

PubChem Compound

118701199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dinis-Oliveira RJ: Portugal's first major forensic case and the genesis of forensic toxicology: 10 years of research to reconstruct the event. Forensic Sci Res. 2018 Nov 20;4(1):69-81. doi: 10.1080/20961790.2018.1534538. eCollection 2019. [PubMed:30915419 ]
Vicentini CB, Manfredini S, Contini C: Ancient treatment for lice: a source of suggestions for carriers of other infectious diseases? Infez Med. 2018 Jun 1;26(2):181-192. [PubMed:29932096 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate (NP0230806)

MOL for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D MOL for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D SDF for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D-SDF for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

PDB for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D PDB for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

SMILES for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

INCHI for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

Structure for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)

3D Structure for NP0230806 ((1s,2r,3r,4r,5s,6s,8r,13s,16s,17r,18r)-8-(acetyloxy)-5-hydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl benzoate)