NP-MRD: Showing NP-Card for 14-Deacetylnudicauline (NP0050780)

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Record Information

Version

2.0

Created at

2022-04-27 22:06:37 UTC

Updated at

2025-02-11 15:46:09 UTC

NP-MRD ID

NP0050780

Natural Product DOI

https://doi.org/10.57994/0443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-Deacetylnudicauline

Description

119347-24-9, Also known as 14-DAN, 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. 14-Deacetylnudicauline is found in Delphinium andersonii, Delphinium barbeyi, Delphinium barbeyi Huth, Delphinium elatum, Delphinium elatum L.var.'black night', Delphinium macrocentrum, Delphinium nuttallianum, Delphinium pentagynum, Delphinium scabriflorum, Delphinium semibarbatum and Delphinium stapeliosum . 14-Deacetylnudicauline was first documented in 2023 (PMID: 36696143). Based on a literature review very few articles have been published on 119347-24-9.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200062D          

 48 55  0  0  1  0            999 V2000
   -1.4824   -1.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -1.7742    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2009   -1.7085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8077   -1.4449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4745   -0.5800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3558   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    0.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990    1.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476   -0.7834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0963   -1.1216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3031   -1.9438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5610   -2.4846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5081   -2.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0976   -3.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650   -2.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1926   -3.0339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -2.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5894   -3.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -4.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9319   -3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -1.1688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9980   -0.4617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5019   -0.2213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9275    0.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4018   -1.0468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1230   -1.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407   -2.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3265   -1.4630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -2.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9704   -2.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360   -1.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3197   -2.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1164   -2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295   -1.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7458   -0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9490   -1.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -3.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366   -3.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524   -3.3465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -4.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773   -4.6054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6262   -3.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4606   -4.0912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -5.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  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
  2  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  0  0  0  0
  4 10  1  1  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 13 22  1  1  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 10 28  1  6  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
 12 31  1  1  0  0  0
  1 32  1  0  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
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  2  0  0  0  0
 45 48  1  6  0  0  0
M  END


  Mrv1652304282200062D          

 48 55  0  0  1  0            999 V2000
   -1.4824   -1.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138   -1.7742    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2009   -1.7085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8077   -1.4449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4745   -0.5800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3558   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4154    0.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0990    1.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4476   -0.7834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0963   -1.1216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3031   -1.9438    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5610   -2.4846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5081   -2.5591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0976   -3.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9650   -2.4748    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1926   -3.0339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5578   -2.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5894   -3.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -4.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9319   -3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1388   -1.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -1.1688    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9980   -0.4617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5019   -0.2213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9275    0.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9961   -0.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4018   -1.0468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1230   -1.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7407   -2.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3265   -1.4630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -2.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9704   -2.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360   -1.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3197   -2.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1164   -2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3295   -1.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7458   -0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9490   -1.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1066   -3.2724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366   -3.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524   -3.3465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802   -4.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1773   -4.6054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6262   -3.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4606   -4.0912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -5.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  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
  2  7  1  0  0  0  0
  5  8  1  6  0  0  0
  8  9  1  0  0  0  0
  4 10  1  1  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 13 22  1  1  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  1  0  0  0
 25 28  1  6  0  0  0
 10 28  1  6  0  0  0
 24 29  1  1  0  0  0
 29 30  1  0  0  0  0
 12 31  1  1  0  0  0
  1 32  1  0  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
 36 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  2  0  0  0  0
 45 48  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050780

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC(=O)C3=C(C=CC=C3)N3C(=O)C[C@H](C)C3=O)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@](O)([C@@H](OC)[C@H]23)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C36H48N2O10/c1-6-37-16-33(17-48-31(42)19-9-7-8-10-22(19)38-25(39)13-18(2)30(38)41)12-11-24(46-4)35-21-14-20-23(45-3)15-34(43,26(21)27(20)40)36(44,32(35)37)29(47-5)28(33)35/h7-10,18,20-21,23-24,26-29,32,40,43-44H,6,11-17H2,1-5H3/t18-,20+,21+,23-,24-,26+,27-,28+,29-,32-,33-,34+,35-,36+/m0/s1

> <INCHI_KEY>
GFWYSOWSJXKFFQ-IPVNYRSLSA-N

> <FORMULA>
C36H48N2O10

> <MOLECULAR_WEIGHT>
668.784

> <EXACT_MASS>
668.330895754

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
71.43367325557132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
-0.1249333623333352

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.883885510417244

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.216957998631427

> <JCHEM_PKA_STRONGEST_BASIC>
9.65827941216208

> <JCHEM_POLAR_SURFACE_AREA>
155.3

> <JCHEM_REFRACTIVITY>
170.85800000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,3R,4S,5S,6S,8R,9S,10S,13S,16S,17R,18S)-11-ethyl-4,8,9-trihydroxy-6,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -2.767  -2.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.146  -3.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.375  -3.189   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.508  -2.697   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.886  -1.083   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.664  -0.649   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.706  -1.817   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.775   0.579   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.185   2.095   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.702  -1.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.913  -2.094   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.299  -3.628   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.914  -4.638   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.949  -4.777   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.182  -6.608   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.391  -7.171   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.801  -4.620   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.360  -5.663   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.041  -4.893   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.100  -7.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.163  -8.496   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.606  -6.105   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.859  -3.569   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.603  -2.182   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.596  -0.862   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.670  -0.413   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.465   1.025   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.726  -0.065   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.217  -1.954   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.563  -2.791   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.116  -5.032   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.343  -2.731   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -5.492  -3.792   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.545  -5.472   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.974  -3.532   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.063  -4.621   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.551  -4.221   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.948  -2.734   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -8.859  -1.645   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -7.372  -2.045   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      -7.666  -6.108   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      -6.228  -6.661   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -4.578  -6.247   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -6.310  -8.199   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -7.798  -8.597   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -8.636  -7.305   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -10.193  -7.637   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -8.350 -10.034   0.000  0.00  0.00           C+0
CONECT    1    2   32                                                       
CONECT    2    1    3    7   19                                             
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10   17                                             
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9                                                       
CONECT    9    8                                                            
CONECT   10    4   11   28                                                  
CONECT   11   10   12   26                                                  
CONECT   12   11   13   23   31                                             
CONECT   13   12   14   17   22                                             
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   13    4   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18    2                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   13                                                            
CONECT   23   12   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   28                                                  
CONECT   26   25   11   27                                                  
CONECT   27   26                                                            
CONECT   28   25   10                                                       
CONECT   29   24   30                                                       
CONECT   30   29                                                            
CONECT   31   12                                                            
CONECT   32    1   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   36   42   46                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46   48                                                  
CONECT   46   45   41   47                                                  
CONECT   47   46                                                            
CONECT   48   45                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  110    0
END

View in JSmol

Synonyms

Value	Source
14-DAN	MeSH
14-Deacetyl-nudicauline	MeSH
14-Deacetylnudicauline	MeSH

Chemical Formula

C₃₆H₄₈N₂O₁₀

Average Mass

668.7840 Da

Monoisotopic Mass

668.33090 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC(=O)C3=C(C=CC=C3)N3C(=O)C[C@H](C)C3=O)CC[C@H](OC)[C@@]34[C@@H]5C[C@H]6[C@H](O)[C@@H]5[C@](O)(C[C@@H]6OC)[C@@](O)([C@@H](OC)[C@H]23)[C@@H]14

InChI Identifier

InChI=1S/C36H48N2O10/c1-6-37-16-33(17-48-31(42)19-9-7-8-10-22(19)38-25(39)13-18(2)30(38)41)12-11-24(46-4)35-21-14-20-23(45-3)15-34(43,26(21)27(20)40)36(44,32(35)37)29(47-5)28(33)35/h7-10,18,20-21,23-24,26-29,32,40,43-44H,6,11-17H2,1-5H3/t18-,20+,21+,23-,24-,26+,27-,28+,29-,32-,33-,34+,35-,36+/m0/s1

InChI Key

GFWYSOWSJXKFFQ-IPVNYRSLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	nurfida@126.com	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	nurfida@126.com	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	nurfida@126.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	nurfida@126.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	nurfida@126.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	nurfida@126.com	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150.94, CD₃OD, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Delphinium andersonii	Plant	KNApSAcK
Delphinium barbeyi	LOTUS Database	35616633
Delphinium barbeyi Huth	Plant	KNApSAcK
Delphinium elatum	LOTUS Database	35616633
Delphinium elatum L.var.'black night'	Plant	KNApSAcK
Delphinium macrocentrum	LOTUS Database	35616633
Delphinium nuttallianum	LOTUS Database	35616633
Delphinium pentagynum	Plant	KNApSAcK
Delphinium scabriflorum	Plant	KNApSAcK
Delphinium semibarbatum	LOTUS Database	35616633
Delphinium shawurense		Not Available
Delphinium stapeliosum	Plant	KNApSAcK

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
Acylaminobenzoic acid or derivatives
1-phenylpyrrolidine
Benzoate ester
Quinolidine
Benzoic acid or derivatives
Alkaloid or derivatives
Benzoyl
Azepane
Monocyclic benzene moiety
Carboxylic acid imide, n-substituted
Piperidine
Pyrrolidone
2-pyrrolidone
Benzenoid
Carboxylic acid imide
Cyclic alcohol
Dicarboximide
Tertiary alcohol
Pyrrole
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
1,2-aminoalcohol
Lactam
Amino acid or derivatives
Secondary alcohol
Azacycle
Monocarboxylic acid or derivatives
Ether
Polyol
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Terpenoid alkaloids (C08673 )

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	1.48	ALOGPS
logP	-0.12	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	155.3 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	170.86 m³·mol⁻¹	ChemAxon
Polarizability	71.43 Å³	ChemAxon
Number of Rings	8	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

C00001629

Chemspider ID

68703146

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101631700

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 14-Deacetylnudicauline (NP0050780)

MOL for NP0050780 (14-Deacetylnudicauline)

3D MOL for NP0050780 (14-Deacetylnudicauline)

3D SDF for NP0050780 (14-Deacetylnudicauline)

3D-SDF for NP0050780 (14-Deacetylnudicauline)

PDB for NP0050780 (14-Deacetylnudicauline)

3D PDB for NP0050780 (14-Deacetylnudicauline)

SMILES for NP0050780 (14-Deacetylnudicauline)

INCHI for NP0050780 (14-Deacetylnudicauline)

Structure for NP0050780 (14-Deacetylnudicauline)

3D Structure for NP0050780 (14-Deacetylnudicauline)