NP-MRD: Showing NP-Card for (1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol (NP0320331)

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Record Information

Version

2.0

Created at

2022-09-11 21:55:25 UTC

Updated at

2022-09-11 21:55:25 UTC

NP-MRD ID

NP0320331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol

Description

Delbrunine 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,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol is found in Delphinium brunonianum. (1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol was first documented in 2010 (PMID: 20550959). Based on a literature review a small amount of articles have been published on Delbrunine (PMID: 35408656) (PMID: 35127798).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112223552D          

 33 39  0  0  1  0            999 V2000
   -1.3519    1.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -0.0057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293   -0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826   -1.5068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1232   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3470   -2.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284   -2.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -2.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985   -1.9170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7940   -2.4935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -1.0585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6765   -0.0883    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2563    0.1463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2746    1.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5442    0.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.0680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0546    0.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746   -0.5388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5497   -0.4980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1869   -1.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3753   -1.3647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5312   -2.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992   -1.4627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2796   -0.9223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9194   -1.6708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5628   -2.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2445   -0.2565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6808    0.1255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707    0.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -1.1495    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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14  3  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 13 26  1  0  0  0  0
 27 26  1  1  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  6  0  0  0
 15 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 33 30  1  1  0  0  0
  5 33  1  0  0  0  0
 13 33  1  0  0  0  0
M  END


  Mrv1652309112223552D          

 33 39  0  0  1  0            999 V2000
   -1.3519    1.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1563   -0.0057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7293   -0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826   -1.5068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1232   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3470   -2.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7651   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284   -2.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -2.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985   -1.9170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7940   -2.4935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877   -1.0585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6765   -0.0883    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2563    0.1463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2746    1.0132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5442    0.7170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954   -0.0680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0546    0.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746   -0.5388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5497   -0.4980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1869   -1.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3753   -1.3647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5312   -2.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7992   -1.4627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2796   -0.9223    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9194   -1.6708    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5628   -2.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2445   -0.2565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6808    0.1255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5707    0.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -1.1495    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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14  3  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 13 26  1  0  0  0  0
 27 26  1  1  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  6  0  0  0
 15 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 33 30  1  1  0  0  0
  5 33  1  0  0  0  0
 13 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC)CC[C@H](O)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@@]5(C[C@@H]6OC)OCO[C@]5([C@@H](OC)[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO7/c1-5-26-10-22(11-29-2)7-6-16(27)24-14-8-13-15(30-3)9-23(17(14)18(13)28)25(21(24)26,33-12-32-23)20(31-4)19(22)24/h13-21,27-28H,5-12H2,1-4H3/t13-,14-,15+,16+,17-,18+,19-,20+,21+,22+,23-,24+,25-/m1/s1

> <INCHI_KEY>
MSIFWQXGXCPJTR-DIZROUMASA-N

> <FORMULA>
C25H39NO7

> <MOLECULAR_WEIGHT>
465.587

> <EXACT_MASS>
465.2726526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.51259750827434

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5S,6S,8R,12S,13S,16S,19S,20R,21S)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-4,19-diol

> <JCHEM_LOGP>
-0.8533076203333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.87178055179514

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.261380240089085

> <JCHEM_PKA_STRONGEST_BASIC>
9.520110356093756

> <JCHEM_POLAR_SURFACE_AREA>
89.85000000000002

> <JCHEM_REFRACTIVITY>
117.9067

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5S,6S,8R,12S,13S,16S,19S,20R,21S)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-4,19-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.524   2.647   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.358   1.523   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.292  -0.011   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.361  -1.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.714  -2.813   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.097  -3.792   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.514  -5.336   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.428  -6.427   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.240  -4.362   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.272  -4.789   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.237  -3.578   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.349  -4.655   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.844  -1.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.263  -0.165   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.345   0.273   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.379   1.891   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.788   2.520   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.749   1.338   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.098  -0.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.702   0.074   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.859  -1.006   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.493  -0.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.682  -1.958   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.301  -2.547   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.725  -3.800   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.358  -2.730   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.255  -1.722   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.450  -3.119   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.651  -4.328   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.456  -0.479   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.271   0.234   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.932   0.208   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.594  -2.146   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   33                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   26   33                                             
CONECT   14   13    3   15                                                  
CONECT   15   14   16   19   30                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20   27                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   13   27                                                  
CONECT   27   26   19   28                                                  
CONECT   28   27   24   29                                                  
CONECT   29   28                                                            
CONECT   30   15   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30    5   13                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₉NO₇

Average Mass

465.5870 Da

Monoisotopic Mass

465.27265 Da

IUPAC Name

(1S,2R,3R,4S,5S,6S,8R,12S,13S,16S,19S,20R,21S)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-4,19-diol

Traditional Name

(1S,2R,3R,4S,5S,6S,8R,12S,13S,16S,19S,20R,21S)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-4,19-diol

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC)CC[C@H](O)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@@]5(C[C@@H]6OC)OCO[C@]5([C@@H](OC)[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C25H39NO7/c1-5-26-10-22(11-29-2)7-6-16(27)24-14-8-13-15(30-3)9-23(17(14)18(13)28)25(21(24)26,33-12-32-23)20(31-4)19(22)24/h13-21,27-28H,5-12H2,1-4H3/t13-,14-,15+,16+,17-,18+,19-,20+,21+,22+,23-,24+,25-/m1/s1

InChI Key

MSIFWQXGXCPJTR-DIZROUMASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delphinium brunonianum	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
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Meta-dioxolane
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.85	ChemAxon
pKa (Strongest Acidic)	14.26	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.85 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.91 m³·mol⁻¹	ChemAxon
Polarizability	50.51 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00028155

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

101986490

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma H, Ma Y, Dawa Z, Yao Y, Wang M, Zhang K, Zhu C, Liu F, Lin C: Diterpenoid Alkaloids Isolated from Delphinium brunonianum and Their Inhibitory Effects on Hepatocytes Lipid Accumulation. Molecules. 2022 Mar 30;27(7). pii: molecules27072257. doi: 10.3390/molecules27072257. [PubMed:35408656 ]
Tang Q, Chen S, Rizvi SAH, Qu J, Wang L, Wang S, Ma C, Liu L, Kang W: Two Alkaloids From Delphinium brunonianum Royle, Their Anti-inflammatory and Anti-oxidative Stress Activity via NF-kappaB Signaling Pathway. Front Nutr. 2022 Jan 20;8:826957. doi: 10.3389/fnut.2021.826957. eCollection 2021. [PubMed:35127798 ]
He YQ, Ma ZY, Wei XM, Du BZ, Jing ZX, Yao BH, Gao LM: Chemical constituents from Delphinium chrysotrichum and their biological activity. Fitoterapia. 2010 Oct;81(7):929-31. doi: 10.1016/j.fitote.2010.06.008. Epub 2010 Jun 13. [PubMed:20550959 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol (NP0320331)

MOL for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

3D MOL for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

3D SDF for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

3D-SDF for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

PDB for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

3D PDB for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

SMILES for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

INCHI for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

Structure for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)

3D Structure for NP0320331 ((1s,2r,3r,4s,5s,6s,8r,12s,13s,16s,19s,20r,21s)-14-ethyl-6,21-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-4,19-diol)