NP-MRD: Showing NP-Card for (1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate (NP0194538)

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Record Information

Version

2.0

Created at

2022-09-04 12:12:40 UTC

Updated at

2022-09-04 12:12:40 UTC

NP-MRD ID

NP0194538

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate

Description

Verussurinine belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. (1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate is found in Veratrum nigrum. Based on a literature review very few articles have been published on Verussurinine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214122D          

 42 48  0  0  1  0            999 V2000
    5.9818    4.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5348    3.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108    3.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    4.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2638    3.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    2.3843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    3.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927    2.4652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1687    2.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7917    3.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    1.8123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2773    2.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987    1.0784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4883    0.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    0.8423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2789    0.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    0.6109    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.0905    2.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3697    1.7314    0.0000 C   0  0  1  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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
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 39 41  1  0  0  0  0
 42 39  1  6  0  0  0
 30 42  1  0  0  0  0
  8 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309042214122D          

 42 48  0  0  1  0            999 V2000
    5.9818    4.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5348    3.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7108    3.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    4.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2638    3.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6408    2.3843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398    3.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927    2.4652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1687    2.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7917    3.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7217    1.8123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2773    2.5074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987    1.0784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4883    0.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7019    0.8423    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2789    0.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    0.6109    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7472    1.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4565    0.1598    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2586    0.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0167   -0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1946   -0.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116    0.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6612   -0.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    1.1736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5319    1.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    2.2328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4126    3.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917    1.6958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9227    1.0380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2997    0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237    0.2637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5006   -0.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3247   -0.5106    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7016   -1.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    0.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3947    0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5707    0.9571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1937    1.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9819    1.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0905    2.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3697    1.7314    0.0000 C   0  0  1  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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 11  1  1  0  0  0
 15 29  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 32  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 42 39  1  6  0  0  0
 30 42  1  0  0  0  0
  8 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194538

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)O[C@H]1[C@H](O)[C@]2(O)[C@@H](C[C@@]34O[C@@]5(O)[C@@H](C[C@@H](O)[C@@H]23)[C@]4(C)CC[C@@H]5O)[C@@H]2CN3C[C@@H](C)CC[C@H]3C(C)(O)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C32H51NO9/c1-6-16(3)27(37)41-24-23-17(14-33-13-15(2)7-8-21(33)29(23,5)38)18-12-30-25(31(18,39)26(24)36)19(34)11-20-28(30,4)10-9-22(35)32(20,40)42-30/h15-26,34-36,38-40H,6-14H2,1-5H3/t15-,16?,17-,18-,19+,20-,21-,22-,23+,24+,25+,26-,28-,29?,30+,31-,32-/m0/s1

> <INCHI_KEY>
KBTBHGPSEWACMW-TUXHAYILSA-N

> <FORMULA>
C32H51NO9

> <MOLECULAR_WEIGHT>
593.758

> <EXACT_MASS>
593.356382226

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
64.15528551049236

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6S,9S,11R,12R,13S,14S,15S,16R,18S,19S,22S,23S,25R)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-12-yl 2-methylbutanoate

> <JCHEM_LOGP>
0.3848674068450544

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.748259421529944

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.93926005668951

> <JCHEM_PKA_STRONGEST_BASIC>
9.704976504856425

> <JCHEM_POLAR_SURFACE_AREA>
160.15

> <JCHEM_REFRACTIVITY>
150.9323

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,9S,11R,12R,13S,14S,15S,16R,18S,19S,22S,23S,25R)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-12-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      11.166   8.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.332   7.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.793   7.115   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.090   8.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.959   5.821   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.663   4.451   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.421   5.896   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.586   4.602   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.048   4.677   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.345   6.047   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.214   3.383   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.384   4.680   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.918   2.013   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.778   0.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.310   1.572   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.521   0.166   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.343   1.140   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.395   2.679   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.719   0.298   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.216   0.658   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.898  -1.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.363  -0.852   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.022   0.766   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.234  -0.125   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.062   2.191   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.993   3.724   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.464   4.168   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.770   5.677   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.664   3.165   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.456   1.938   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.159   0.568   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       7.698   0.492   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       8.401  -0.878   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.939  -0.953   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.643  -2.323   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.774   0.341   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.070   1.711   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.532   1.787   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.828   3.156   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.299   3.612   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       7.636   4.684   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.290   3.232   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   42                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   29                                             
CONECT   12   11                                                            
CONECT   13   11   14   30                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23   29                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19   25                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   15   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   17   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   11   15                                                  
CONECT   30   13   31   42                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   32   39                                                  
CONECT   39   38   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39   30    8                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₅₁NO₉

Average Mass

593.7580 Da

Monoisotopic Mass

593.35638 Da

IUPAC Name

(1S,2S,6S,9S,11R,12R,13S,14S,15S,16R,18S,19S,22S,23S,25R)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-12-yl 2-methylbutanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)O[C@H]1[C@H](O)[C@]2(O)[C@@H](C[C@@]34O[C@@]5(O)[C@@H](C[C@@H](O)[C@@H]23)[C@]4(C)CC[C@@H]5O)[C@@H]2CN3C[C@@H](C)CC[C@H]3C(C)(O)[C@@H]12

InChI Identifier

InChI=1S/C32H51NO9/c1-6-16(3)27(37)41-24-23-17(14-33-13-15(2)7-8-21(33)29(23,5)38)18-12-30-25(31(18,39)26(24)36)19(34)11-20-28(30,4)10-9-22(35)32(20,40)42-30/h15-26,34-36,38-40H,6-14H2,1-5H3/t15-,16?,17-,18-,19+,20-,21-,22-,23+,24+,25+,26-,28-,29?,30+,31-,32-/m0/s1

InChI Key

KBTBHGPSEWACMW-TUXHAYILSA-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
Veratrum nigrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Cerveratrum-type alkaloids

Alternative Parents

Substituents

Cerveratrum-type alkaloid
Azasteroid
Quinolizidine
Alkaloid or derivatives
Oxepane
Fatty acid ester
Fatty acyl
Piperidine
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	0.38	ChemAxon
pKa (Strongest Acidic)	10.94	ChemAxon
pKa (Strongest Basic)	9.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	160.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	150.93 m³·mol⁻¹	ChemAxon
Polarizability	64.16 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024023

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

101596431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate (NP0194538)

MOL for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

3D MOL for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

3D SDF for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

3D-SDF for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

PDB for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

3D PDB for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

SMILES for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

INCHI for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

Structure for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)

3D Structure for NP0194538 ((1s,2s,6s,9s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23s,25r)-10,13,14,16,22,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-12-yl 2-methylbutanoate)