NP-MRD: Showing NP-Card for methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate (NP0289317)

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Record Information

Version

2.0

Created at

2022-09-09 19:26:36 UTC

Updated at

2022-09-09 19:26:36 UTC

NP-MRD ID

NP0289317

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

Description

Catharanthine belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond. Catharanthine is one of the two precursors that form vinblastine, the other being vindoline. Catharanthine is a very strong basic compound (based on its pKa). Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown. methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate is found in Catharanthus roseus. Catharanthine is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241511362D          

 25 29  0  0  0  0            999 V2000
    1.2601   -1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345   -0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777    1.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    1.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961    1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    1.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277   -0.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191    0.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3047    1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103    1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203    1.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9372    0.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1031    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8834   -0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.9988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -1.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
  7 21  1  0  0  0  0
 19 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
   -3.7102   -0.7737    1.8332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3254    0.6171    1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4955    0.5217    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7878    1.0433   -1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8494    0.5485   -2.1148 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7538   -0.9656   -1.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929   -1.2958   -0.7016 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -2.4209   -0.5020 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707   -2.2873    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.1601    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149    0.1367   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3432    0.8419   -0.3871 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106    0.0088   -0.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7721    0.2102   -0.2815 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471   -0.8288   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1470   -2.0733    0.2705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7899   -2.3072    0.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9298   -1.2567    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1360    0.7320   -0.3092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2414    1.9924    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960    2.3467    1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3545    2.7833    0.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3935    3.9819    1.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4544    1.0751   -1.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022   -0.2140    0.2270 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4474   -1.1999    1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108   -0.6586    2.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433   -1.4332    1.8782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7159    1.0799    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2134    1.2214    1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833    1.7260   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1377    0.8897   -3.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8022   -1.3392   -2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0803   -1.2944   -2.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1388   -2.8149   -1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411   -3.2551   -0.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2067   -3.2721    0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2746   -2.1967    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4263    1.8575   -0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1107    1.2156   -0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7092   -0.6200   -0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8685   -2.8817    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3758   -3.2726    0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    4.0519    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269    4.0192    1.9085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409    4.8135    0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    2.1475   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    0.5542   -2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639   -0.5941    1.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 11 19  1  0
 19 24  1  0
 19 25  1  0
 19 20  1  1
 20 21  2  0
 20 22  1  0
 22 23  1  0
 25  3  1  0
 24  5  1  0
 25  7  1  0
 18 10  1  0
 18 13  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  6
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  1
 23 44  1  0
 23 45  1  0
 23 46  1  0
M  END


  Mrv1533004241511362D          

 25 29  0  0  0  0            999 V2000
    1.2601   -1.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5419   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345   -0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691    1.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4777    1.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999    1.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8961    1.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7346    1.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    1.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926    0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4277   -0.1994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9191    0.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091    0.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3047    1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5103    1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203    1.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9372    0.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4840    0.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1031    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8834   -0.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.9988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5695   -1.0919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5158   -1.9152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  0  0  0  0
  7 21  1  0  0  0  0
 19 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>
NP0289317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=CC2CN3CCC4=C(NC5=CC=CC=C45)C(C2)(C13)C(=O)OC

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

> <INCHI_KEY>
CMKFQVZJOWHHDV-UHFFFAOYSA-N

> <FORMULA>
C21H24N2O2

> <MOLECULAR_WEIGHT>
336.435

> <EXACT_MASS>
336.183778021

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.81951686540023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.191242942666666

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.37114941596033

> <JCHEM_PKA_STRONGEST_BASIC>
7.486466578744895

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
98.71149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       2.352  -2.690   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.012  -1.932   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.998  -0.392   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.052   0.762   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.062   1.891   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.892   3.441   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.240   2.649   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.539   3.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.105   3.474   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.781   2.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.213   0.611   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.398  -0.372   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.699   0.452   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.182   0.036   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.284   1.113   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.902   2.605   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.419   3.020   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.318   1.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.616   0.354   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.770   1.639   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.059   0.818   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.516  -1.183   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.135  -1.864   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.796  -2.038   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.696  -3.575   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   13                                                  
CONECT   19   11   20   21   22                                             
CONECT   20   19    5                                                       
CONECT   21   19    3    7                                                  
CONECT   22   19   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
Catharanthine monohydrochloride, (2alpha,5beta,6alpha,18beta)-isomer	MeSH
Catharanthine sulfate, (2alpha,5beta,6alpha,18beta)-isomer	MeSH
Methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylic acid	Generator
Methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0,.0,.0,]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₄N₂O₂

Average Mass

336.4350 Da

Monoisotopic Mass

336.18378 Da

IUPAC Name

methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

Traditional Name

methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CCC1=CC2CN3CCC4=C(NC5=CC=CC=C45)C(C2)(C13)C(=O)OC

InChI Identifier

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

InChI Key

CMKFQVZJOWHHDV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Catharanthus roseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ibogan-type alkaloids

Sub Class

Not Available

Direct Parent

Ibogan-type alkaloids

Alternative Parents

Substituents

Ibogan skeleton
Catharanthine skeleton
Pyrroloazepine
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Azepine
Aralkylamine
Benzenoid
Piperidine
Methyl ester
Heteroaromatic compound
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
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Amine
Organonitrogen compound
Organooxygen 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	3.56	ALOGPS
logP	3.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	16.37	ChemAxon
pKa (Strongest Basic)	7.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.71 m³·mol⁻¹	ChemAxon
Polarizability	37.82 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Catharanthine

METLIN ID

Not Available

PubChem Compound

418553

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate (NP0289317)

MOL for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

3D MOL for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

3D SDF for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

3D-SDF for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

PDB for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

3D PDB for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

SMILES for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

INCHI for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

Structure for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)

3D Structure for NP0289317 (methyl 17-ethyl-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate)