NP-MRD: Showing NP-Card for (2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol (NP0253825)

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Record Information

Version

2.0

Created at

2022-09-07 17:48:41 UTC

Updated at

2022-09-07 17:48:41 UTC

NP-MRD ID

NP0253825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol

Description

GELSEMINE, also known as gelsemin, belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21. (2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol is found in Gelsemium elegans and Gelsemium sempervirens. (2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol was first documented in 2021 (PMID: 34468296). Based on a literature review a small amount of articles have been published on GELSEMINE (PMID: 35335173) (PMID: 35203954) (PMID: 34972069) (PMID: 34627953).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219482D          

 24 29  0  0  1  0            999 V2000
    0.1733   -2.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4764   -1.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429   -0.8565    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0966   -0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4299   -0.4949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416   -0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3461   -2.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9649   -2.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8430   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005   -1.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7247   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8685   -1.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -0.6991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6111    0.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139    0.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042    0.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9439    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    0.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766   -0.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1637   -1.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602   -0.5413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
  3 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 14 23  1  0  0  0  0
 24 14  1  6  0  0  0
  7 24  1  0  0  0  0
  3 24  1  0  0  0  0
M  END

     RDKit          3D

 46 51  0  0  0  0  0  0  0  0999 V2000
   -2.8519   -0.8554    2.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9385    0.0973    2.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    0.2881    0.8144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2674    1.5072    0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3728    2.0649   -0.7794 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1057    2.3284   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3988    0.9699   -0.9848 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1957   -0.2106   -1.4296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4261   -1.2580   -2.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6006   -1.8142   -1.4335 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4196   -1.7794   -0.0820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0090   -2.0378    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8089   -0.8356   -0.1598 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8841   -0.5225    0.5853 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1558   -0.6766    2.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2750   -1.1821    3.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3409   -0.2852    2.2725 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0209    0.1408    1.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3498    0.6024    0.9769 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125    0.8986   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9857    0.7411   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6785    0.2820   -1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679   -0.0252    0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262    0.6097    0.4628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2050   -1.0477    3.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901   -1.4795    1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5854    0.6766    2.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2204    1.1603   -0.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4615    2.1886    1.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0882    1.8420   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4422    2.0207   -2.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2530    3.4296   -2.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    1.3008   -1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0598    0.0800   -2.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0386   -0.8190   -3.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454   -2.0598   -2.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -2.6263    0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -2.9752   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0415   -2.1782    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8735   -1.0386   -0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689   -2.0670    3.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9723    0.7149    1.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8370    1.2547   -0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3200    0.9623   -2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0816    0.1234   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2970    1.4894    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  1
  2  1  2  3
  3 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 24  1  0
 24 14  1  0
 14 15  1  1
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  7  5  1  0
 23 14  1  0
 24  3  1  0
 23 18  1  0
  8 13  1  0
 14 11  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  4 28  1  0
  4 29  1  0
  2 27  1  0
  1 25  1  0
  1 26  1  0
 13 40  1  6
 12 38  1  0
 12 39  1  0
 11 37  1  1
  9 35  1  0
  9 36  1  0
  8 34  1  6
  7 33  1  6
 24 46  1  1
 16 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END


  Mrv1652309072219482D          

 24 29  0  0  1  0            999 V2000
    0.1733   -2.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4764   -1.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429   -0.8565    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0966   -0.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4299   -0.4949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3416   -0.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3461   -2.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9649   -2.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8430   -2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1005   -1.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7247   -1.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8685   -1.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225   -0.6991    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6111    0.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8139    0.5102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042    0.5458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9439    0.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7591    0.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766   -0.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -1.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1637   -1.3870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6463   -0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602   -0.5413    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
  3 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 14 23  1  0  0  0  0
 24 14  1  6  0  0  0
  7 24  1  0  0  0  0
  3 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@@]2(C=C)C3CC4OCC3C1[C@@H]2[C@@]41C(O)=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11?,13?,15?,16?,17-,19-,20-/m0/s1

> <INCHI_KEY>
NFYYATWFXNPTRM-ZIWPNRSCSA-N

> <FORMULA>
C20H22N2O2

> <MOLECULAR_WEIGHT>
322.408

> <EXACT_MASS>
322.168127956

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.66893541636714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2'S,3S,6'S)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-ol

> <JCHEM_LOGP>
-0.5861531193163414

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.880663333632059

> <JCHEM_PKA_STRONGEST_BASIC>
10.207084079049931

> <JCHEM_POLAR_SURFACE_AREA>
45.06

> <JCHEM_REFRACTIVITY>
93.51970000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2'S,3S,6'S)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.324  -4.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.889  -2.642   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.693  -1.599   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.047  -0.003   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.802  -0.924   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -0.638  -0.277   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.746  -2.228   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.513  -3.805   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.668  -5.042   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.307  -4.771   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.788  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.086  -2.454   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.488  -2.959   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.269  -1.305   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.874   0.184   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.386   0.952   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       6.168   1.019   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.362   0.047   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.884   0.283   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.850  -0.916   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.294  -2.352   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.772  -2.589   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.806  -1.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.472  -1.011   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13   24                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8    3                                                  
CONECT   14   11   15   23   24                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   14                                                  
CONECT   24   14    7    3                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Value	Source
Gelsemin	MeSH

Chemical Formula

C₂₀H₂₂N₂O₂

Average Mass

322.4080 Da

Monoisotopic Mass

322.16813 Da

IUPAC Name

(2'S,3S,6'S)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-ol

Traditional Name

(2'S,3S,6'S)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-ol

CAS Registry Number

Not Available

SMILES

CN1C[C@@]2(C=C)C3CC4OCC3C1[C@@H]2[C@@]41C(O)=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11?,13?,15?,16?,17-,19-,20-/m0/s1

InChI Key

NFYYATWFXNPTRM-ZIWPNRSCSA-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
Gelsemium elegans	LOTUS Database	35616633
Gelsemium sempervirens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Gelsemium alkaloids

Sub Class

Not Available

Direct Parent

Gelsemium alkaloids

Alternative Parents

Substituents

Gelsemium skeleton
Indole or derivatives
Dihydroindole
Isoindoline
Isoindole or derivatives
Aralkylamine
Oxepane
Benzenoid
N-alkylpyrrolidine
Piperidine
Oxane
Pyrrolidine
Carboxamide group
Amino acid or derivatives
Lactam
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Oxacycle
Azacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Organoheterocyclic compound
Amine
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.59	ChemAxon
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.52 m³·mol⁻¹	ChemAxon
Polarizability	34.67 Å³	ChemAxon
Number of Rings	6	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

C00001734

Chemspider ID

21249188

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6713959

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang SJ, Zuo MT, Qi XJ, Ma X, Wang ZY, Liu ZY: In vitro Metabolism of Humantenine in Liver Microsomes from Human, Pig, Goat and Rat. Curr Drug Metab. 2021;22(10):795-7801. doi: 10.2174/1389200222666210901113530. [PubMed:34468296 ]
Wu ZH, Su Y, Luo ZF, Sun ZL, Gong ZH, Xiao LT: In Situ Visual Distribution of Gelsemine, Koumine, and Gelsenicine by MSI in Gelsemiumelegans at Different Growth Stages. Molecules. 2022 Mar 10;27(6):1810. doi: 10.3390/molecules27061810. [PubMed:35335173 ]
Yu H, Tang MH, Zeng ZY, Huang SJ, Zheng XF, Liu ZY: Suppressive Effects of Gelsemine on Anxiety-like Behaviors Induced by Chronic Unpredictable Mild Stress in Mice. Brain Sci. 2022 Jan 30;12(2):191. doi: 10.3390/brainsci12020191. [PubMed:35203954 ]
Yang H, Xiang P, Yu M, Zou D, Fan X, Wang X, Liu W: Confirmation of Gelsemium elegans poisoning by UHPLC-MS/MS analysis of koumine, gelsemine, and gelsenicine in hair. J Pharm Biomed Anal. 2022 Feb 20;210:114546. doi: 10.1016/j.jpba.2021.114546. Epub 2021 Dec 23. [PubMed:34972069 ]
You G, Yang R, Wei Y, Hu W, Gan L, Xie C, Zheng Z, Liu Z, Liao R, Ye L: The detoxification effect of cytochrome P450 3A4 on gelsemine-induced toxicity. Toxicol Lett. 2021 Dec 15;353:34-42. doi: 10.1016/j.toxlet.2021.10.003. Epub 2021 Oct 8. [PubMed:34627953 ]
LOTUS database [Link]

Showing NP-Card for (2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol (NP0253825)

MOL for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

3D MOL for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

3D SDF for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

3D-SDF for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

PDB for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

3D PDB for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

SMILES for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

INCHI for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

Structure for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)

3D Structure for NP0253825 ((2's,3s,6's)-2'-ethenyl-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-ol)