NP-MRD: Showing NP-Card for methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate (NP0329914)

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Record Information

Version

1.0

Created at

2022-09-12 14:46:37 UTC

Updated at

2022-09-12 14:46:37 UTC

NP-MRD ID

NP0329914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate

Description

Tubotaiwine 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,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate is found in Alstonia angustifolia, Alstonia scholaris, Amsonia tomentosa, Catharanthus roseus, Tabernaemontana divaricata, Hunteria zeylanica, Melodinus fusiformis, Rauvolfia serpentina, Strychnos angolensis, Tabernaemontana africana, Tabernaemontana eglandulosa, Tabernaemontana elegans, Tabernaemontana pachysiphon and Tabernaemontana ventricosa. It was first documented in 2016 (PMID: 26275898). Based on a literature review a significant number of articles have been published on Tubotaiwine (PMID: 35408605) (PMID: 34697745) (PMID: 32756456) (PMID: 31766620).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216462D          

 24 28  0  0  1  0            999 V2000
   -0.8444   -0.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6117    0.1322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2167    0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744   -0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1406   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -1.1615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4126   -1.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960   -1.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -0.2782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8249    0.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    1.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    1.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5454    2.5367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    2.4152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570    3.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5848    0.9629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    0.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959    0.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273   -0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340   -1.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093   -1.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779   -0.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1192   -0.4837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24  7  1  6  0  0  0
M  END

     RDKit          3D

 48 52  0  0  0  0  0  0  0  0999 V2000
   -2.5729   -1.1522    2.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1232   -1.1820    2.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -1.5643    0.6999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9302   -0.6547   -0.1751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0662   -1.3669   -1.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8181   -1.9504   -2.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2138   -2.3098   -1.1338 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4855   -1.9651   -1.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -0.4624   -1.5628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9278   -0.3243   -0.1481 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0075    0.8036   -0.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2683    0.6561   -0.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9765    1.7654   -1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1824    1.5909   -1.3474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125    3.0031   -1.2382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1925    4.0297   -1.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7255    1.8756    0.5064 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009    1.3972    0.9631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    2.0868    1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1070    1.3986    2.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1809    0.0515    1.8477 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1991   -0.6107    1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0719    0.0631    0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -1.6364    0.1182 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0182   -0.1516    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821   -1.3510    3.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -1.8915    1.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7108   -0.1689    2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5626   -1.9122    2.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5278   -2.5776    0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -0.4962    0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4380   -0.5852   -2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982   -2.1153   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380   -1.2925   -2.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179   -2.9009   -2.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3424   -2.4683   -1.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662   -2.1328   -2.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5492   -0.1185   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035    0.1052   -2.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2573    3.7446   -1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435    4.9360   -1.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7922    4.3162   -2.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763    2.8815    0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786    3.1430    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8988    1.9076    2.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0337   -0.5131    2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2332   -1.6760    0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534   -2.2249    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 24  1  0
 24  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  6
 10 11  1  0
 11 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 11 12  2  0
 12  4  1  0
  4  5  1  0
  5  6  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
  4  3  1  0
 10 24  1  0
 23 10  1  0
  6  7  1  0
 23 18  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  1
 24 48  1  1
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
  4 31  1  1
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv1652309122216462D          

 24 28  0  0  1  0            999 V2000
   -0.8444   -0.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6117    0.1322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2167    0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744   -0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1406   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7036   -1.1615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4126   -1.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0960   -1.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9012   -0.2782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8249    0.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    1.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    1.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5454    2.5367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377    2.4152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4570    3.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5848    0.9629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1712    0.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959    0.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273   -0.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340   -1.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093   -1.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779   -0.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1192   -0.4837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24  7  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0329914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1[C@H]2N3CC[C@@]22C(NC4=CC=CC=C24)=C(C1CC3)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O2/c1-3-12-13-8-10-22-11-9-20(18(12)22)14-6-4-5-7-15(14)21-17(20)16(13)19(23)24-2/h4-7,12-13,18,21H,3,8-11H2,1-2H3/t12-,13?,18+,20+/m0/s1

> <INCHI_KEY>
RLAKWLFUMAABBE-BMWAJPDPSA-N

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.424

> <EXACT_MASS>
324.183778021

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.928190373638415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,17R,18S)-18-ethyl-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_LOGP>
2.2582812539999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.980956252562393

> <JCHEM_PKA_STRONGEST_BASIC>
10.270074203598881

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
95.83470000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,17R,18S)-18-ethyl-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.576  -1.122   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.164  -0.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.142   0.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.404   1.126   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.699  -0.163   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.263  -1.766   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.313  -2.168   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.637  -3.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.913  -2.149   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.549  -0.519   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.406   1.134   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.906   1.909   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.859   3.538   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.885   4.735   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.630   4.508   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.853   6.032   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.825   1.797   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.920   0.708   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.459   0.749   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.530  -1.917   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.991  -1.958   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.185  -0.646   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.089  -0.903   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23   24                                             
CONECT   11   10   12   17                                                  
CONECT   12   11    4   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   10                                                  
CONECT   24   10    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
Dihydrocondylocarpine	MeSH
Tubotaiwin	MeSH
Condyfolan-16-carboxylic acid, 2,16-didehydro-, methyl ester	MeSH

Chemical Formula

C₂₀H₂₄N₂O₂

Average Mass

324.4240 Da

Monoisotopic Mass

324.18378 Da

IUPAC Name

methyl (1S,17R,18S)-18-ethyl-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraene-10-carboxylate

Traditional Name

methyl (1S,17R,18S)-18-ethyl-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@@H]1[C@H]2N3CC[C@@]22C(NC4=CC=CC=C24)=C(C1CC3)C(=O)OC

InChI Identifier

InChI=1S/C20H24N2O2/c1-3-12-13-8-10-22-11-9-20(18(12)22)14-6-4-5-7-15(14)21-17(20)16(13)19(23)24-2/h4-7,12-13,18,21H,3,8-11H2,1-2H3/t12-,13?,18+,20+/m0/s1

InChI Key

RLAKWLFUMAABBE-BMWAJPDPSA-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 angustifolia	LOTUS Database	35616633
Alstonia scholaris	LOTUS Database	35616633
Amsonia tomentosa	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Ervatamia coronaria	LOTUS Database	35616633
Hunteria zeylanica	LOTUS Database	35616633
Melodinus fusiformis	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633
Strychnos angolensis	LOTUS Database	35616633
Tabernaemontana africana	LOTUS Database	35616633
Tabernaemontana eglandulosa	LOTUS Database	35616633
Tabernaemontana elegans	LOTUS Database	35616633
Tabernaemontana pachysiphon	LOTUS Database	35616633
Tabernaemontana ventricosa	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
Aspidosperma alkaloid
Carbazole
Indolizidine
Dihydroindole
Indole or derivatives
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Piperidine
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Enamine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	2.26	ChemAxon
pKa (Strongest Acidic)	13.98	ChemAxon
pKa (Strongest Basic)	10.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.83 m³·mol⁻¹	ChemAxon
Polarizability	35.93 Å³	ChemAxon
Number of Rings	5	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

C00025216

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

134716702

PDB ID

Not Available

ChEBI ID

141960

Good Scents ID

Not Available

References

General References

Sevik Kilicaslan O, Cretton S, Quiros-Guerrero L, Bella MA, Kaiser M, Maser P, Ndongo JT, Cuendet M: Isolation and Structural Elucidation of Compounds from Pleiocarpa bicarpellata and Their In Vitro Antiprotozoal Activity. Molecules. 2022 Mar 28;27(7). pii: molecules27072200. doi: 10.3390/molecules27072200. [PubMed:35408605 ]
Gao L, Li X: Protective Effect of Tubotaiwine on Cadmium-Induced Hypertension in Rats through Reduction in Arterial Stiffness and Vascular Remodeling. Dokl Biochem Biophys. 2021 Sep;500(1):368-375. doi: 10.1134/S1607672921050136. Epub 2021 Oct 25. [PubMed:34697745 ]
Morales-Jadan D, Blanco-Salas J, Ruiz-Tellez T, Centeno F: Three Alkaloids from an Apocynaceae Species, Aspidosperma spruceanum as Antileishmaniasis Agents by In Silico Demo-case Studies. Plants (Basel). 2020 Aug 3;9(8). pii: plants9080983. doi: 10.3390/plants9080983. [PubMed:32756456 ]
Akhgari A, Laakso I, Maaheimo H, Choi YH, Seppanen-Laakso T, Oksman-Caldentey KM, Rischer H: Methyljasmonate Elicitation Increases Terpenoid Indole Alkaloid Accumulation in Rhazya stricta Hairy Root Cultures. Plants (Basel). 2019 Nov 22;8(12). pii: plants8120534. doi: 10.3390/plants8120534. [PubMed:31766620 ]
Cao J, Shen HM, Wang Q, Qian Y, Guo HC, Li K, Qiao X, Guo DA, Luo XD, Ye M: Characterization of chemical constituents and rats metabolites of an alkaloidal extract of Alstonia scholaris leaves by liquid chromatography coupled with mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jul 15;1026:43-55. doi: 10.1016/j.jchromb.2015.07.044. Epub 2015 Jul 29. [PubMed:26275898 ]
LOTUS database [Link]

Showing NP-Card for methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate (NP0329914)

MOL for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

3D MOL for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

3D SDF for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

3D-SDF for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

PDB for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

3D PDB for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

SMILES for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

INCHI for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

Structure for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)

3D Structure for NP0329914 (methyl (1s,17r,18s)-18-ethyl-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraene-10-carboxylate)