NP-MRD: Showing NP-Card for 7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one (NP0211316)

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Record Information

Version

2.0

Created at

2022-09-05 09:33:31 UTC

Updated at

2022-09-05 09:33:31 UTC

NP-MRD ID

NP0211316

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one

Description

7'-Ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]Dodecane]-2-one 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. 7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one is found in Gelsemium elegans. 7'-Ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]Dodecane]-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502332D          

 41 47  0  0  0  0            999 V2000
    6.0531   -1.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2282   -1.2319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8270   -0.5110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0079   -0.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4464   -1.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491    0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1305   -0.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4254    0.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4806    1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9269    2.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800    2.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7046    1.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9565    1.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0858    2.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3254    1.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6756    2.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7909    2.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1148    1.1639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1743    0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
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  9 10  1  0  0  0  0
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  6 12  1  0  0  0  0
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  9 14  1  0  0  0  0
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  8 19  1  0  0  0  0
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 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  2  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
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 36 37  2  0  0  0  0
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 37 40  1  0  0  0  0
 40 41  2  0  0  0  0
  3 41  1  0  0  0  0
 34 41  1  0  0  0  0
M  END

     RDKit          3D

 79 85  0  0  0  0  0  0  0  0999 V2000
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   -2.2135    0.7467   -0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4037    2.2787    1.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3537    3.2052    1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3227   -2.7168    1.2660 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004241502332D          

 41 47  0  0  0  0            999 V2000
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    0.7909    2.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1103    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6490    0.1029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4622   -0.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6728   -0.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0147   -0.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -0.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199   -0.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0500    0.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5221    1.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2252    0.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    1.1639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5313    0.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6246    1.4951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -1.7045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4030   -1.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8751   -2.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5699    0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540    1.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5426    1.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1469    1.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9354    1.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1196    2.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9628    0.4799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1743    0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  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
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  4  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 20 19  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 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
 25 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  0  0  0  0
 21 32  1  0  0  0  0
 32 33  2  0  0  0  0
  6 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  2  0  0  0  0
  3 41  1  0  0  0  0
 34 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211316

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)C2(CC3C4COC2CC4C(CN3C=C2C3C(CC(C)C3(O)CO)OC2=O)=CC)C2=CC=C(OC)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C31H38N2O8/c1-5-17-12-32(13-20-27-25(41-28(20)35)8-16(2)31(27,37)15-34)24-11-30(26-10-19(17)21(24)14-40-26)22-7-6-18(38-3)9-23(22)33(39-4)29(30)36/h5-7,9,13,16,19,21,24-27,34,37H,8,10-12,14-15H2,1-4H3

> <INCHI_KEY>
BDAVFAANEJPEMQ-UHFFFAOYSA-N

> <FORMULA>
C31H38N2O8

> <MOLECULAR_WEIGHT>
566.651

> <EXACT_MASS>
566.262816192

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.13049212874502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecane]-2-one

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
1.187150502999998

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.235378772197382

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.38429607859068

> <JCHEM_PKA_STRONGEST_BASIC>
-0.1353290390027745

> <JCHEM_POLAR_SURFACE_AREA>
118.00000000000001

> <JCHEM_REFRACTIVITY>
148.79609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecane]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      11.299  -2.324   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.759  -2.300   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.010  -0.954   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.481  -0.769   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.433  -1.897   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.185   0.742   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.844  -0.087   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.527   0.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.631   2.504   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.464   4.149   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.056   3.888   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.915   2.319   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.519   3.087   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.894   3.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.474   2.967   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.261   3.916   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.476   5.441   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.073   1.416   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.078   0.192   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.729  -1.308   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.256  -1.756   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.028  -0.827   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.235  -1.708   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.464  -0.780   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.960   0.676   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.841   1.939   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.420   0.646   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.214   2.173   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.992   1.261   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.166   2.791   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.788  -3.182   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.752  -3.211   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.633  -4.474   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.530   1.491   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.874   2.992   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.346   3.445   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.474   2.397   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.946   2.850   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.290   4.351   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.131   0.896   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.659   0.443   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18    8   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   22   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   23   32                                                       
CONECT   32   31   21   33                                                  
CONECT   33   32                                                            
CONECT   34    6   35   41                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   41                                                       
CONECT   41   40    3   34                                                  
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈N₂O₈

Average Mass

566.6510 Da

Monoisotopic Mass

566.26282 Da

IUPAC Name

7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-hexahydro-2H-cyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecane]-2-one

Traditional Name

7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecane]-2-one

CAS Registry Number

Not Available

SMILES

CON1C(=O)C2(CC3C4COC2CC4C(CN3C=C2C3C(CC(C)C3(O)CO)OC2=O)=CC)C2=CC=C(OC)C=C12

InChI Identifier

InChI=1S/C31H38N2O8/c1-5-17-12-32(13-20-27-25(41-28(20)35)8-16(2)31(27,37)15-34)24-11-30(26-10-19(17)21(24)14-40-26)22-7-6-18(38-3)9-23(22)33(39-4)29(30)36/h5-7,9,13,16,19,21,24-27,34,37H,8,10-12,14-15H2,1-4H3

InChI Key

BDAVFAANEJPEMQ-UHFFFAOYSA-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

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
Terpene lactone
Aromatic monoterpenoid
Monoterpenoid
Indole or derivatives
Anisole
Alkyl aryl ether
Oxepane
Aralkylamine
Benzenoid
Piperidine
Gamma butyrolactone
Oxane
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
1,2-diol
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Lactone
Oxacycle
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Allylamine
Dialkyl ether
Enamine
Ether
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxygen compound
Alcohol
Organopnictogen compound
Organooxygen compound
Carbonyl group
Organic oxide
Organonitrogen 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	2.31	ALOGPS
logP	1.19	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-0.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	148.8 m³·mol⁻¹	ChemAxon
Polarizability	59.13 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one (NP0211316)

MOL for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D MOL for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D SDF for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D-SDF for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

PDB for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D PDB for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

SMILES for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

INCHI for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

Structure for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D Structure for NP0211316 (7'-ethylidene-5'-{[4-hydroxy-4-(hydroxymethyl)-5-methyl-2-oxo-tetrahydrocyclopenta[b]furan-3-ylidene]methyl}-1,6-dimethoxy-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)