NP-MRD: Showing NP-Card for methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate (NP0288204)

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Record Information

Version

2.0

Created at

2022-09-09 17:48:58 UTC

Updated at

2022-09-09 17:48:58 UTC

NP-MRD ID

NP0288204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate

Description

Stemmadenine 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. methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate is found in Alstonia angustiloba, Alstonia scholaris, Rauvolfia serpentina, Rhazya stricta, Tabernaemontana grandiflora and Tabernaemontana cymosa. methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate was first documented in 2020 (PMID: 32098650). Based on a literature review a small amount of articles have been published on Stemmadenine (PMID: 35528313) (PMID: 35812900) (PMID: 35209210) (PMID: 34153839).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219482D          

 26 29  0  0  1  0            999 V2000
   -1.3929    0.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0273   -0.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0256    0.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    1.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647    1.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354    0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849   -0.7208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379   -0.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2495   -0.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7834    0.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5056    1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939    1.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601    0.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -0.7131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0522   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138   -2.0529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0948   -1.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915   -2.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2760   -1.5732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -0.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -0.6222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7261    0.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6814    0.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 11 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24  3  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -3.0256   -2.4102    1.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6132   -1.0643    1.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9947   -0.8364    0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394   -2.0465   -0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1306   -1.6974   -1.8342 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2494   -1.8809   -1.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -0.6557   -1.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5105   -0.3682   -0.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8297    0.4041    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5592    0.3695    1.6704 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6389   -0.3691    1.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.6833    2.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7092   -1.4948    2.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7380   -2.0039    0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7085   -1.6787   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489   -0.8590    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4156    1.1240    0.3719 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8492    1.7768    1.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379    2.6064    1.5094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0811    2.3520   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0620    2.5487   -0.9234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413    3.3242   -0.7277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7531    4.4771   -1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5870    0.5403   -0.2209 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8036    0.6890   -1.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -0.6059   -2.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6828   -3.2315    1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7803   -2.5417    2.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1543   -2.4221    1.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8614   -0.2506    2.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6593   -2.6635   -0.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9596   -2.6283   -0.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -2.5830   -2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5646   -2.5046   -0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659    0.2024   -2.3216 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0270   -0.9542   -2.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522    0.8603    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6742   -0.3036    3.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4928   -1.7197    2.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5537   -2.6381    0.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7109   -2.0616   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9341    1.0500    2.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0126    2.4619    2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880    3.5625    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6470    5.1377   -1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216    5.0379   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6216    4.2024   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4343    1.1707    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.4938   -2.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8192    1.1322   -1.9699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7873   -0.9561   -2.7057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3397   -0.4111   -3.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 17 20  1  6
 17 18  1  0
 18 19  1  0
 17 24  1  0
 24 25  1  0
 25 26  1  0
 26  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 16 11  1  0
  3 24  1  0
 16  8  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 24 48  1  1
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
  4 31  1  0
  4 32  1  0
  2 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
M  END


  Mrv1652309092219482D          

 26 29  0  0  1  0            999 V2000
   -1.3929    0.1318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7282   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0273   -0.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0256    0.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    1.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2647    1.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3354    0.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1036   -0.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7849   -0.7208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379   -0.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2495   -0.3643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7834    0.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5056    1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6939    1.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1601    0.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170   -0.7131    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0522   -1.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9138   -2.0529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0948   -1.4725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915   -2.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2760   -1.5732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -0.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -0.6222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7261    0.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6814    0.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 11 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24  3  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(CO)[C@H]2CCN(C\C2=C/C)CCC2=C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3+/t17-,21-/m0/s1

> <INCHI_KEY>
MBXJCHZRHROMQA-ITKISHOESA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.76542498057009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,2S,16Z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0^{3,11}.0^{5,10}]octadeca-3(11),5,7,9-tetraene-2-carboxylate

> <JCHEM_LOGP>
2.090376408999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.435492858254356

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.82430960279552

> <JCHEM_PKA_STRONGEST_BASIC>
7.603666840612513

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
102.77859999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S,16Z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0^{3,11}.0^{5,10}]octadeca-3(11),5,7,9-tetraene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.600   0.246   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.359  -0.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.051  -0.048   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.048   1.489   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.864   2.730   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.361   3.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.741   2.411   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.359   1.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.927  -0.477   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       5.199  -1.345   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.417  -0.404   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.932  -0.680   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.929   0.494   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.410   1.944   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.895   2.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.899   1.046   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.645  -1.331   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.831  -2.314   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.572  -3.832   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.044  -2.749   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.971  -3.978   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.515  -2.937   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.412  -1.707   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.115  -1.161   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.355   0.156   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.272   1.454   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   11                                                  
CONECT   17    9   18   20   24                                             
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   17    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    5                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

methyl (1S,2S,16Z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0^{3,11}.0^{5,10}]octadeca-3(11),5,7,9-tetraene-2-carboxylate

Traditional Name

methyl (1S,2S,16Z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0^{3,11}.0^{5,10}]octadeca-3(11),5,7,9-tetraene-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(CO)[C@H]2CCN(C\C2=C/C)CCC2=C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C21H26N2O3/c1-3-14-12-23-10-8-16-15-6-4-5-7-18(15)22-19(16)21(13-24,20(25)26-2)17(14)9-11-23/h3-7,17,22,24H,8-13H2,1-2H3/b14-3+/t17-,21-/m0/s1

InChI Key

MBXJCHZRHROMQA-ITKISHOESA-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
Alstonia angustiloba	LOTUS Database	35616633
Alstonia scholaris	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633
Rhazya stricta	LOTUS Database	35616633
Stemmadenia grandiflora	LOTUS Database	35616633
Tabernaemontana cymosa	LOTUS Database	35616633

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

Stemmadenine-skeleton
3-alkylindole
Indole
Indole or derivatives
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Piperidine
Benzenoid
Heteroaromatic compound
Methyl ester
Pyrrole
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Amine
Primary alcohol
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	2.09	ChemAxon
pKa (Strongest Acidic)	14.82	ChemAxon
pKa (Strongest Basic)	7.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.78 m³·mol⁻¹	ChemAxon
Polarizability	39.77 Å³	ChemAxon
Number of Rings	4	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

C00026041

Chemspider ID

58816284

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Stemmadenine

METLIN ID

Not Available

PubChem Compound

20839798

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kalshetti MG, Argade NP: The indole-based subincanadine alkaloids and their biogenetic congeners. Alkaloids Chem Biol. 2020;83:187-223. doi: 10.1016/bs.alkal.2019.12.001. Epub 2020 Jan 27. [PubMed:32098650 ]
Nagarajan K, Ghai R, Varshney G, Grover P, Genovese C, D'Angeli F, Goel R, Prasad T, Kalaivani M, Teotia AK: Identification of Potent Bioassay Guided Terpenoid and Glycoside Root Fractions of Astragalus candolleanus against Clinically Significant Bacterial Strains. Int J Microbiol. 2022 Apr 28;2022:4584799. doi: 10.1155/2022/4584799. eCollection 2022. [PubMed:35528313 ]
Boccia M, Grzech D, Lopes AA, O'Connor SE, Caputi L: Directed Biosynthesis of New to Nature Alkaloids in a Heterologous Nicotiana benthamiana Expression Host. Front Plant Sci. 2022 Jun 22;13:919443. doi: 10.3389/fpls.2022.919443. eCollection 2022. [PubMed:35812900 ]
Abdul-Hameed ZH, Bawakid NO, Alorfi HS, Sobahi TR, Alburae NA, Abdel-Lateff A, Elbehairi SEI, Alfaifi MY, Alhakamy NA, Alarif WM: Monoterpene Indole Alkaloids from the Aerial Parts of Rhazya stricta Induce Cytotoxicity and Apoptosis in Human Adenocarcinoma Cells. Molecules. 2022 Feb 19;27(4):1422. doi: 10.3390/molecules27041422. [PubMed:35209210 ]
Hugel HM, de Silva NH, Siddiqui A, Blanch E, Lingham A: Natural spirocyclic alkaloids and polyphenols as multi target dementia leads. Bioorg Med Chem. 2021 Aug 1;43:116270. doi: 10.1016/j.bmc.2021.116270. Epub 2021 Jun 10. [PubMed:34153839 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate (NP0288204)

MOL for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

3D MOL for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

3D SDF for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

3D-SDF for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

PDB for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

3D PDB for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

SMILES for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

INCHI for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

Structure for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)

3D Structure for NP0288204 (methyl (1s,2s,16z)-16-ethylidene-2-(hydroxymethyl)-4,14-diazatetracyclo[12.2.2.0³,¹¹.0⁵,¹⁰]octadeca-3(11),5,7,9-tetraene-2-carboxylate)