NP-MRD: Showing NP-Card for Pseudostrychnine (NP0067450)

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Record Information

Version

2.0

Created at

2022-04-28 12:18:19 UTC

Updated at

2022-04-28 12:18:19 UTC

NP-MRD ID

NP0067450

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pseudostrychnine

Description

Pseudostrychnine belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. Pseudostrychnine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Pseudostrychnine is found in Strychnos icaja, Strychnos lucida R.Br., Strychnos nux-vomica and Strychnos nux-vomica L. . Pseudostrychnine was first documented in 1948 (PMID: 18869451). Based on a literature review a small amount of articles have been published on pseudostrychnine (PMID: 12560037) (PMID: 22707864) (PMID: 19235686) (PMID: 18878794).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214182D          

 26 32  0  0  1  0            999 V2000
    4.3938    2.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3975    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6848    0.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9649    2.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775    2.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720    2.5061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7503    1.6882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1888    1.0002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2300   -0.4468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550    0.8790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8992    1.5794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4850    2.2660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0295    2.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    3.0403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1769    3.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987    3.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551    3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    3.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117    2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8306    2.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9801    1.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    0.8319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    3.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 17 26  1  1  0  0  0
M  END

     RDKit          3D

 48 54  0  0  0  0  0  0  0  0999 V2000
    1.0827    3.8414    1.2448 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169    2.9713    0.8044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1203    3.2956    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9636    2.0641    0.2905 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2819    1.4979    1.5461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3685    0.6448    1.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8428   -0.6931    0.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1883   -0.9861   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152   -2.4053   -0.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4489   -2.5906   -0.7134 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4017   -2.9552    0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5997   -1.6248    1.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6607   -0.5947   -0.0199 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0763   -0.1419   -0.1021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121   -0.8439   -0.4172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4691   -0.2522   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5456    1.0863   -0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4320    1.7951    0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688    1.1932    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8829    1.7178    0.4917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0629    0.6007    0.3985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1316    1.1333   -0.5267 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8491    0.0256   -1.2092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7859   -0.6405   -2.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1632   -1.3573   -1.1710 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2653   -1.7407   -1.9588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2010    3.9638   -0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5406    3.7877    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655    2.4024   -0.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8270    0.5184    2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0871    1.0568    0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0060   -1.5347    1.6133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9011   -2.8689    0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5421   -2.9475   -0.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -3.6615    1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3357   -3.4241    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -1.3857    1.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5724   -1.6902    1.6504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2070   -1.9045   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3720   -0.7905   -0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141    1.5969   -0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568    2.8638    0.4561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5438    0.4699    1.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110    1.7378   -1.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121    0.3563   -1.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524    0.1053   -2.7050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011   -1.3898   -2.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052   -2.3024   -2.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 26  1  6
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  1
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
 13 25  1  0
 10 25  1  0
  8 23  1  0
  4 22  1  0
 13 21  1  0
  2 20  1  0
 14 19  1  0
 26 48  1  0
 24 46  1  0
 24 47  1  0
 23 45  1  6
 22 44  1  6
 21 43  1  1
 18 42  1  0
 17 41  1  0
 16 40  1  0
 15 39  1  0
 12 37  1  0
 12 38  1  0
 11 35  1  0
 11 36  1  0
  9 33  1  0
  9 34  1  0
  7 32  1  0
  6 30  1  0
  6 31  1  0
  4 29  1  6
  3 27  1  0
  3 28  1  0
M  END


  Mrv1652304282214182D          

 26 32  0  0  1  0            999 V2000
    4.3938    2.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3975    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6848    0.9003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    1.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9649    2.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775    2.5503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720    2.5061    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7503    1.6882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1888    1.0002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    0.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2300   -0.4468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9458    0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550    0.8790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8992    1.5794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4850    2.2660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0295    2.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5553    3.0403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1769    3.7387    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987    3.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551    3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700    3.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117    2.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8306    2.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9801    1.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3994    0.8319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    3.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14  8  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 17 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067450

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@]12C[C@@H]3[C@@H]4[C@@H]5N6C7=CC=CC=C7[C@]15CCN2CC3=CCO[C@H]4CC6=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O3/c24-17-9-16-18-13-10-21(25)20(6-7-22(21)11-12(13)5-8-26-16)14-3-1-2-4-15(14)23(17)19(18)20/h1-5,13,16,18-19,25H,6-11H2/t13-,16-,18-,19-,20-,21+/m0/s1

> <INCHI_KEY>
HCCFPODVEOBUMM-YOQTYQRRSA-N

> <FORMULA>
C21H22N2O3

> <MOLECULAR_WEIGHT>
350.418

> <EXACT_MASS>
350.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.416414868674664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,11S,18R,20R,21R,22S)-18-hydroxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.5081358279999995

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.240138614275555

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.647286096635039

> <JCHEM_PKA_STRONGEST_BASIC>
7.96160454998596

> <JCHEM_POLAR_SURFACE_AREA>
53.010000000000005

> <JCHEM_REFRACTIVITY>
96.0854

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11S,18R,20R,21R,22S)-18-hydroxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.202   3.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.209   2.457   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.878   1.681   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.541   2.445   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.534   3.985   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.865   4.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.054   4.678   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.267   3.151   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.086   1.867   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.330   0.462   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.163  -0.834   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.766   0.360   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.849   1.641   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.679   2.948   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.905   4.230   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.922   4.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.903   5.675   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       2.197   6.979   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.731   7.464   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.770   6.209   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.504   6.738   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.209   5.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.550   4.272   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.830   2.705   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.746   1.553   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.104   6.640   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17   20                                             
CONECT    8    7    9   14                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13    8   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16    7   18   26                                             
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19    7                                                       
CONECT   21   18   22                                                       
CONECT   22   21   15   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   13                                                       
CONECT   26   17                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   64    0
END

View in JSmol

Synonyms

Value	Source
(-)-Pseudostrychnine	ChEBI
16-Hydroxystrychnine	ChEBI

Chemical Formula

C₂₁H₂₂N₂O₃

Average Mass

350.4180 Da

Monoisotopic Mass

350.16304 Da

IUPAC Name

(1S,11S,18R,20R,21R,22S)-18-hydroxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one

Traditional Name

(1S,11S,18R,20R,21R,22S)-18-hydroxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one

CAS Registry Number

Not Available

SMILES

O[C@]12C[C@@H]3[C@@H]4[C@@H]5N6C7=CC=CC=C7[C@]15CCN2CC3=CCO[C@H]4CC6=O

InChI Identifier

InChI=1S/C21H22N2O3/c24-17-9-16-18-13-10-21(25)20(6-7-22(21)11-12(13)5-8-26-16)14-3-1-2-4-15(14)23(17)19(18)20/h1-5,13,16,18-19,25H,6-11H2/t13-,16-,18-,19-,20-,21+/m0/s1

InChI Key

HCCFPODVEOBUMM-YOQTYQRRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Strychnos icaja	Plant	KNApSAcK
Strychnos lucida R.Br.	Plant	KNApSAcK
Strychnos nux-vomica	LOTUS Database	35616633
Strychnos nux-vomica L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Quinolidine
Indole or derivatives
Indolizidine
Delta-lactam
Piperidinone
Benzenoid
N-alkylpyrrolidine
Piperidine
Cyclic alcohol
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Hemiaminal
Lactam
Ether
Dialkyl ether
Alkanolamine
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen 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	0.89	ALOGPS
logP	0.51	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.65	ChemAxon
pKa (Strongest Basic)	7.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.01 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	96.09 m³·mol⁻¹	ChemAxon
Polarizability	36.42 Å³	ChemAxon
Number of Rings	7	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

C00025200

Chemspider ID

10308749

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21723446

PDB ID

Not Available

ChEBI ID

132666

Good Scents ID

Not Available

References

General References

Philippe G, De Mol P, Zeches-Hanrot M, Nuzillard JM, Tits MH, Angenot L, Frederich M: Indolomonoterpenic alkaloids from Strychnos icaja roots. Phytochemistry. 2003 Feb;62(4):623-9. doi: 10.1016/s0031-9422(02)00612-x. [PubMed:12560037 ]
Bhati R, Singh A, Saharan VA, Ram V, Bhandari A: Strychnos nux-vomica seeds: Pharmacognostical standardization, extraction, and antidiabetic activity. J Ayurveda Integr Med. 2012 Apr;3(2):80-4. doi: 10.4103/0975-9476.96523. [PubMed:22707864 ]
Ma L, Yang XW, Xu W, Cai BC, Hattori M: Intestinal permeability of antitumor alkaloids from the processed seeds of Strychnos nux-vomica in a Caco-2 cell model. Planta Med. 2009 May;75(6):631-4. doi: 10.1055/s-0029-1185387. Epub 2009 Feb 23. [PubMed:19235686 ]
BAILEY AS, ROBINSON R: Strychnine and brucine; a new method for the preparation of pseudostrychnine. J Chem Soc. 1948 May;2:703-5. doi: 10.1039/jr9480000703. [PubMed:18869451 ]
PAUSACKER KH, ROBINSON R: Strychnine and brucine; experiments with pseudostrychnine, dihydropseudostrychnine, and neostrychnine. J Chem Soc. 1948 Jul;1:951-6. doi: 10.1039/jr9480000951. [PubMed:18878794 ]

Showing NP-Card for Pseudostrychnine (NP0067450)

MOL for NP0067450 (Pseudostrychnine)

3D MOL for NP0067450 (Pseudostrychnine)

3D SDF for NP0067450 (Pseudostrychnine)

3D-SDF for NP0067450 (Pseudostrychnine)

PDB for NP0067450 (Pseudostrychnine)

3D PDB for NP0067450 (Pseudostrychnine)

SMILES for NP0067450 (Pseudostrychnine)

INCHI for NP0067450 (Pseudostrychnine)

Structure for NP0067450 (Pseudostrychnine)

3D Structure for NP0067450 (Pseudostrychnine)