NP-MRD: Showing NP-Card for (1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one (NP0222927)

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Record Information

Version

2.0

Created at

2022-09-06 00:53:22 UTC

Updated at

2022-09-06 00:53:22 UTC

NP-MRD ID

NP0222927

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one

Description

Gelsevirine 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. (1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one is found in Gelsemium elegans, Gelsemium rankinii and Gelsemium sempervirens. (1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one was first documented in 2017 (PMID: 29234422). Based on a literature review a small amount of articles have been published on Gelsevirine (PMID: 35202579) (PMID: 33955684) (PMID: 30989727) (PMID: 30953910).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062202532D          

 26 31  0  0  1  0            999 V2000
    0.1633   -2.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788   -1.4170    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
   -0.3421   -0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.1935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3461   -2.0382    0.0000 C   0  0  1  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  2  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  1  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
    1.8021    0.4966    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
    3.3547    1.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    1.9111    0.0000 C   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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  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  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 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
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 14 25  1  0  0  0  0
 26 14  1  6  0  0  0
  7 26  1  0  0  0  0
  3 26  1  0  0  0  0
M  END

     RDKit          3D

 50 55  0  0  0  0  0  0  0  0999 V2000
   -1.2329   -2.5055   -1.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -1.2456   -1.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -0.4369   -0.8113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8874   -0.9755    0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -0.7894    1.4181 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6209   -0.2539    2.1963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4379    0.2107    1.2779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1308    1.3769    0.5658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3796    2.6061    0.9701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219    2.3067    0.9099 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397    1.7162   -0.3007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7524    1.8528   -1.3354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9242    1.0217   -0.9199 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6284    0.2235   -0.1543 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1941   -0.2204   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8041   -0.1275   -2.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4243   -0.8801   -1.1750 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162   -1.5281   -2.0987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8008   -0.5620   -2.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6952   -0.7533    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8416   -1.2070    0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9999   -0.9500    2.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0096   -0.2481    2.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8871    0.1860    2.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6896   -0.0512    0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6197   -0.5070    0.2381 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0119   -2.9395   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1414   -3.1439   -2.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8147   -0.8493   -2.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8238   -0.4787   -0.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266   -2.0759   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3243    0.6531    2.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4591   -0.0193    1.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9692   -1.0028    2.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9935    0.4700    2.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2069    1.4019    0.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6202    2.7463    2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6805    3.5339    0.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709    2.2229   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3850    1.7259   -2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1461    2.9262   -1.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7943    1.3410   -1.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1202   -0.1993   -3.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7103   -0.9925   -3.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0840    0.3304   -2.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182   -1.7614    0.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8920   -1.3094    2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1482   -0.0564    3.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1739    0.7353    2.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4135   -1.5172    0.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 14 15  1  6
 14 26  1  0
 26  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  2  1  6
  2  1  2  3
 14 25  1  0
 25 24  2  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 20 17  1  0
 11 14  1  0
 20 25  1  0
  3 26  1  0
  5  7  1  0
 13  8  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 26 50  1  1
  7 35  1  1
  8 36  1  1
  9 37  1  0
  9 38  1  0
 11 39  1  6
 12 40  1  0
 12 41  1  0
 13 42  1  6
  4 30  1  0
  4 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  2 29  1  0
  1 27  1  0
  1 28  1  0
 24 49  1  0
 23 48  1  0
 22 47  1  0
 21 46  1  0
M  END


  Mrv1652309062202532D          

 26 31  0  0  1  0            999 V2000
    0.1633   -2.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788   -1.4170    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
   -0.3421   -0.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -1.1935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3461   -2.0382    0.0000 C   0  0  1  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  2  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  1  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
    1.8021    0.4966    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
    3.3547    1.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0578    1.9111    0.0000 C   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
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  6  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  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 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
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 14 25  1  0  0  0  0
 26 14  1  6  0  0  0
  7 26  1  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222927

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)[C@@]2([C@H]3[C@H]4[C@H]5CO[C@@H]2C[C@H]5[C@@]3(CN4C)C=C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-4-20-11-22(2)17-12-10-26-16(9-14(12)20)21(18(17)20)13-7-5-6-8-15(13)23(25-3)19(21)24/h4-8,12,14,16-18H,1,9-11H2,2-3H3/t12-,14+,16+,17+,18-,20-,21-/m0/s1

> <INCHI_KEY>
SSSCMFCWHWCCEH-MTYPYGCKSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.63201643086984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-1-methoxy-4'-methyl-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-one

> <JCHEM_LOGP>
1.4326901343333343

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.565479276724844

> <JCHEM_POLAR_SURFACE_AREA>
42.010000000000005

> <JCHEM_REFRACTIVITY>
97.23070000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.305  -4.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.894  -2.645   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      -0.639  -0.274   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       3.364   0.927   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  O   UNK     0       6.262   2.658   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.575   3.567   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.362   0.047   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.884   0.283   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.850  -0.916   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.294  -2.352   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.772  -2.589   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.806  -1.390   0.000  0.00  0.00           C+0
HETATM   26  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   26                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
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   25   26                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   14                                                  
CONECT   26   14    7    3                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

(1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-1-methoxy-4'-methyl-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-one

Traditional Name

(1'R,2'S,3S,5'S,6'S,8'R,11'S)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2-one

CAS Registry Number

Not Available

SMILES

CON1C(=O)[C@@]2([C@H]3[C@H]4[C@H]5CO[C@@H]2C[C@H]5[C@@]3(CN4C)C=C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C21H24N2O3/c1-4-20-11-22(2)17-12-10-26-16(9-14(12)20)21(18(17)20)13-7-5-6-8-15(13)23(25-3)19(21)24/h4-8,12,14,16-18H,1,9-11H2,2-3H3/t12-,14+,16+,17+,18-,20-,21-/m0/s1

InChI Key

SSSCMFCWHWCCEH-MTYPYGCKSA-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 rankinii	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
Isoindoline
Isoindole or derivatives
Oxepane
Aralkylamine
Oxane
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.43	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.01 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.23 m³·mol⁻¹	ChemAxon
Polarizability	37.63 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00025087

Chemspider ID

24716430

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14217344

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Y, Wang H, Wu S, Li D, Chen S: Effect of Gelsemium elegans and Mussaenda pubescens, the Components of a Detoxification Herbal Formula, on Disturbance of the Intestinal Absorptions of Indole Alkaloids in Caco-2 Cells. Evid Based Complement Alternat Med. 2017;2017:6947948. doi: 10.1155/2017/6947948. Epub 2017 Oct 16. [PubMed:29234422 ]
Feng M, Kong D, Guo H, Xing C, Lv J, Bian H, Lv N, Zhang C, Chen D, Liu M, Yu Y, Su L: Gelsevirine improves age-related and surgically induced osteoarthritis in mice by reducing STING availability and local inflammation. Biochem Pharmacol. 2022 Apr;198:114975. doi: 10.1016/j.bcp.2022.114975. Epub 2022 Feb 22. [PubMed:35202579 ]
Zhang HH, Yang WJ, Huang YJ, Li WJ, Zhang SX, Liu ZY: The metabolism of gelsevirine in human, pig, goat and rat liver microsomes. Vet Med Sci. 2021 Sep;7(5):2086-2092. doi: 10.1002/vms3.499. Epub 2021 May 6. [PubMed:33955684 ]
Zhang HH, Huang YJ, Liu YC, Jiang XY, Zhang SX, Liu ZY: Characterization of gelsevirine metabolites in rat liver S9 by accurate mass measurements using high-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2019 Jul 30;33(14):1179-1184. doi: 10.1002/rcm.8457. [PubMed:30989727 ]
Sun MX, Cui Y, Li Y, Meng WQ, Xu QQ, Zhao J, Lu JC, Xiao K: Indole alkaloids from Gelsemium elegans. Phytochemistry. 2019 Jun;162:232-240. doi: 10.1016/j.phytochem.2019.03.016. Epub 2019 Apr 4. [PubMed:30953910 ]
LOTUS database [Link]

Showing NP-Card for (1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one (NP0222927)

MOL for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

3D MOL for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

3D SDF for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

3D-SDF for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

PDB for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

3D PDB for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

SMILES for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

INCHI for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

Structure for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)

3D Structure for NP0222927 ((1'r,2's,3s,5's,6's,8'r,11's)-2'-ethenyl-1-methoxy-4'-methyl-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2-one)