NP-MRD: Showing NP-Card for Tabersonine (NP0050909)

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Record Information

Version

2.0

Created at

2022-04-27 22:22:36 UTC

Updated at

2022-04-27 22:22:37 UTC

NP-MRD ID

NP0050909

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tabersonine

Description

Tabersonine belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system. Tabersonine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Tabersonine is found in Alstonia yunnanensis, Amsonia angustifolia, Amsonia elliptica, Amsonia illustris, Amsonia tabernaemontana, Amsonia tomentosa, Apis cerana, Catharanthus roseus , Catharanthus trichophyllus, Tabernaemontana divaricata, Ervatamia divaricata Gouyahua, Melodinus fusiformis, Melodinus suaveolens, Rauvolfia serpentina, Tabernaemontana grandiflora, Tabernaemontana alternifolia, Tabernaemontana catharinensis, Tabernaemontana citrifolia, Tabernaemontana cymosa, Tabernaemontana litoralis, Vinca herbacea Waldst.et Kit. and Voacanga africana . Tabersonine was first documented in 2021 (PMID: 34680551). Based on a literature review a small amount of articles have been published on tabersonine (PMID: 35323487) (PMID: 34531512) (PMID: 34459997) (PMID: 34302444).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200222D          

 25 29  0  0  1  0            999 V2000
    3.1134    0.3131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    0.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    0.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4694   -0.4048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8288   -0.9246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0583   -0.6298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3236   -1.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7396   -0.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -0.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303   -1.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -2.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109   -1.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5398   -1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899   -1.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587   -1.7393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7293   -2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3699   -1.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2399   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100    0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8805   -0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391    1.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797    2.0394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686    1.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386    2.6290    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  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  1  0  0  0
 20 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -1.1784    1.7213   -2.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2710    1.2254   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8222    0.5967   -0.0850 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1034    0.3949    0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6672   -0.7870    0.6958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0344   -1.9344    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5946   -1.8775    0.1303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335   -1.9928    1.5273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363   -1.1043    1.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889   -0.6664    0.3569 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0213    0.5684    0.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687    1.7024    0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906    2.9689    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4585    4.0559    0.6549 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4546    3.0119    0.3891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006    4.2234    0.3898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895    1.6788    0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4138    0.2191    0.2162 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5204   -1.1662   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6133   -1.9224   -0.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -3.2248   -0.8638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1481   -3.7741   -0.9181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -2.9853   -0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2425   -1.6645   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -0.6240   -0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0114    0.9986   -3.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510    2.6780   -2.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2133    1.9180   -1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9883    0.5599   -1.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8899    2.1162   -1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    1.2654    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6137   -0.8842    1.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667   -2.8531    0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3620   -2.0507   -1.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085   -3.0397    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0694   -1.7960    2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -0.2703    2.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8161   -1.6485    2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6551    4.3017   -0.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0108    4.1421    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5067    5.0329    0.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    1.6845    1.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4593    2.6747    0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2258    0.8732    0.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6341   -1.5375   -0.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862   -3.8178   -1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0205   -4.8166   -1.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0847   -3.4364   -0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8579   -0.7376   -1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3 17  1  0
 17 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 12 11  2  0
 11 18  1  0
 18 19  1  0
 19 24  2  0
 24 23  1  0
 23 22  2  0
 22 21  1  0
 21 20  2  0
 24 10  1  0
 10  9  1  1
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7 25  1  0
  4  3  1  0
 25  3  1  0
 10 11  1  0
 25 10  1  0
 20 19  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
 17 42  1  0
 17 43  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 18 44  1  0
 23 48  1  0
 22 47  1  0
 21 46  1  0
 20 45  1  0
  9 37  1  0
  9 38  1  0
  8 35  1  0
  8 36  1  0
  6 33  1  0
  6 34  1  0
  5 32  1  0
  4 31  1  0
 25 49  1  6
M  END


  Mrv1652304282200222D          

 25 29  0  0  1  0            999 V2000
    3.1134    0.3131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9284    0.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5690    0.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3395    0.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4694   -0.4048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8288   -0.9246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0583   -0.6298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3236   -1.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7396   -0.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430   -0.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7303   -1.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3143   -2.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1109   -1.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5398   -1.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9899   -1.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9587   -1.7393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7293   -2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3699   -1.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2399   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100    0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8805   -0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4391    1.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0797    2.0394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686    1.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5386    2.6290    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  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  1  0  0  0
 20 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050909

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CC(C(=O)OC)=C3NC4=C(C=CC=C4)[C@@]33CCN(CC=C1)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1

> <INCHI_KEY>
FNGGIPWAZSFKCN-ACRUOGEOSA-N

> <FORMULA>
C21H24N2O2

> <MOLECULAR_WEIGHT>
336.435

> <EXACT_MASS>
336.183778021

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.36600485035368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
2.5878174760000006

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.065459620419091

> <JCHEM_PKA_STRONGEST_BASIC>
9.083108599513523

> <JCHEM_POLAR_SURFACE_AREA>
41.57000000000001

> <JCHEM_REFRACTIVITY>
101.24780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate

> <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  N   UNK     0       5.812   0.584   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.333   0.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.529   1.316   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.967   0.765   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.210  -0.756   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.014  -1.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.576  -1.176   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.204  -1.876   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.114  -0.788   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.627  -1.189   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.230  -2.676   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.320  -3.764   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.807  -3.364   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.608  -2.373   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.448  -3.664   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       9.256  -3.247   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      10.695  -3.797   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.890  -2.827   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.648  -1.306   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.405   0.215   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.844  -0.336   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.286   2.836   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.482   3.807   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.848   3.387   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.605   4.908   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19   20                                             
CONECT    6    5    7   16                                                  
CONECT    7    6    2    8   14                                             
CONECT    8    7    9   13                                                  
CONECT    9    8    1   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    7   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5                                                       
CONECT   20    5   21                                                       
CONECT   21   20                                                            
CONECT   22    3   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
(5alpha,12beta,19alpha)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylic acid, methyl ester	ChEBI
Methyl (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate	ChEBI
Tabersonin	ChEBI
(5a,12b,19a)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylate, methyl ester	Generator
(5a,12b,19a)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylic acid, methyl ester	Generator
(5alpha,12beta,19alpha)-2,3,6,7-Tetradehydroaspidospermidine-3-carboxylate, methyl ester	Generator
(5Α,12β,19α)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate, methyl ester	Generator
(5Α,12β,19α)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid, methyl ester	Generator
Methyl (5a,12b,19a)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate	Generator
Methyl (5a,12b,19a)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid	Generator
Methyl (5alpha,12beta,19alpha)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid	Generator
Methyl (5α,12β,19α)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylate	Generator
Methyl (5α,12β,19α)-2,3,6,7-tetradehydroaspidospermidine-3-carboxylic acid	Generator
Tabersonine monoacetate	MeSH

Chemical Formula

C₂₁H₂₄N₂O₂

Average Mass

336.4350 Da

Monoisotopic Mass

336.18378 Da

IUPAC Name

methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate

Traditional Name

methyl (1R,12R,19S)-12-ethyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate

CAS Registry Number

Not Available

SMILES

CC[C@@]12CC(C(=O)OC)=C3NC4=C(C=CC=C4)[C@@]33CCN(CC=C1)[C@@H]23

InChI Identifier

InChI=1S/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21-/m0/s1

InChI Key

FNGGIPWAZSFKCN-ACRUOGEOSA-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
Alstonia yunnanensis	Plant	KNApSAcK
Amsonia angustifolia	Plant	KNApSAcK
Amsonia elliptica	LOTUS Database	35616633
Amsonia illustris	Plant	KNApSAcK
Amsonia tabernaemontana	Plant	KNApSAcK
Amsonia tomentosa	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Catharanthus roseus	Plant	KNApSAcK
Catharanthus trichophyllus	LOTUS Database	35616633
Ervatamia coronaria	LOTUS Database	35616633
Ervatamia divaricata Gouyahua	Plant	KNApSAcK
Melodinus fusiformis	LOTUS Database	35616633
Melodinus suaveolens	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633
Stemmadenia grandiflora	LOTUS Database	35616633
Tabernaemontana alternifolia	LOTUS Database	35616633
Tabernaemontana catharinensis	LOTUS Database	35616633
Tabernaemontana citrifolia	LOTUS Database	35616633
Tabernaemontana cymosa	LOTUS Database	35616633
Tabernaemontana litoralis	Plant	KNApSAcK
Vinca herbacea Waldst.et Kit.	Plant	KNApSAcK
Voacanga africana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Plumeran-type alkaloids

Sub Class

Not Available

Direct Parent

Plumeran-type alkaloids

Alternative Parents

Substituents

Plumeran-type alkaloid
Carbazole
Indole or derivatives
Dihydroindole
Secondary aliphatic/aromatic amine
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous amide
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Secondary amine
Enamine
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid ester (CHEBI:16776 )
monoterpenoid indole alkaloid (CHEBI:16776 )
Indole alkaloids (C09244 )

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	3.56	ALOGPS
logP	2.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	9.08	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	101.25 m³·mol⁻¹	ChemAxon
Polarizability	37.37 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

C00001773

Chemspider ID

19292

KEGG Compound ID

C09244

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tabersonine

METLIN ID

Not Available

PubChem Compound

20485

PDB ID

Not Available

ChEBI ID

16776

Good Scents ID

Not Available

References

General References

Tang W, Liu X, He Y, Yang F: Enhancement of Vindoline and Catharanthine Accumulation, Antioxidant Enzymes Activities, and Gene Expression Levels in Catharanthus roseus Leaves by Chitooligosaccharides Elicitation. Mar Drugs. 2022 Mar 3;20(3). pii: md20030188. doi: 10.3390/md20030188. [PubMed:35323487 ]
Shekunov EV, Efimova SS, Yudintceva NM, Muryleva AA, Zarubaev VV, Slita AV, Ostroumova OS: Plant Alkaloids Inhibit Membrane Fusion Mediated by Calcium and Fragments of MERS-CoV and SARS-CoV/SARS-CoV-2 Fusion Peptides. Biomedicines. 2021 Oct 10;9(10). pii: biomedicines9101434. doi: 10.3390/biomedicines9101434. [PubMed:34680551 ]
Liu T, Huang Y, Jiang L, Dong C, Gou Y, Lian J: Efficient production of vindoline from tabersonine by metabolically engineered Saccharomyces cerevisiae. Commun Biol. 2021 Sep 16;4(1):1089. doi: 10.1038/s42003-021-02617-w. [PubMed:34531512 ]
Mall M, Shanker K, Samad A, Kalra A, Sundaresan V, Shukla AK: Stress responsiveness of vindoline accumulation in Catharanthus roseus leaves is mediated through co-expression of allene oxide cyclase with pathway genes. Protoplasma. 2022 May;259(3):755-773. doi: 10.1007/s00709-021-01701-6. Epub 2021 Aug 30. [PubMed:34459997 ]
Kulagina N, Guirimand G, Melin C, Lemos-Cruz P, Carqueijeiro I, De Craene JO, Oudin A, Heredia V, Koudounas K, Unlubayir M, Lanoue A, Imbault N, St-Pierre B, Papon N, Clastre M, Giglioli-Guivarc'h N, Marc J, Besseau S, Courdavault V: Enhanced bioproduction of anticancer precursor vindoline by yeast cell factories. Microb Biotechnol. 2021 Nov;14(6):2693-2699. doi: 10.1111/1751-7915.13898. Epub 2021 Jul 24. [PubMed:34302444 ]

Showing NP-Card for Tabersonine (NP0050909)

MOL for NP0050909 (Tabersonine)

3D MOL for NP0050909 (Tabersonine)

3D SDF for NP0050909 (Tabersonine)

3D-SDF for NP0050909 (Tabersonine)

PDB for NP0050909 (Tabersonine)

3D PDB for NP0050909 (Tabersonine)

SMILES for NP0050909 (Tabersonine)

INCHI for NP0050909 (Tabersonine)

Structure for NP0050909 (Tabersonine)

3D Structure for NP0050909 (Tabersonine)