NP-MRD: Showing NP-Card for Catharanthine (NP0050850)

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Record Information

Version

2.0

Created at

2022-04-27 22:15:33 UTC

Updated at

2022-04-27 22:15:33 UTC

NP-MRD ID

NP0050850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Catharanthine

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 found in Catharanthus roseus , Catharanthus trichophyllus, Tabernaemontana divaricata and Tabernaemontana catharinensis. Catharanthine was first documented in 2021 (PMID: 34782816). Based on a literature review a small amount of articles have been published on catharanthine (PMID: 35323487) (PMID: 35304861) (PMID: 35011546) (PMID: 34998026).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200152D          

 25 29  0  0  1  0            999 V2000
    2.4050   -1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808   -0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -0.2350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4310   -1.1245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7271   -1.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -2.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734   -1.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -0.3913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7214   -0.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -0.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4996   -0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    0.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    1.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070    0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310    1.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    0.2282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -0.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843   -1.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6324   -1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299    0.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  3 10  1  0  0  0  0
  9 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  1  0  0  0  0
  3 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 20 25  2  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -4.1064   -0.3770    1.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8720   -1.1866    0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7481   -0.8099   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229   -0.4424   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6162   -0.2045   -2.1439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6411   -1.3465   -1.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091   -1.8855   -0.6517 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0977   -2.7232   -0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4241   -2.2077    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -0.8006    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    0.2599   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5953    1.3535   -0.4033 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.9980   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0393    1.7325   -0.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2739    1.1313   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3402   -0.2101   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053   -0.9694   -0.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9660   -0.3414   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6166    0.3812   -0.0166 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8367    1.4048    1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    1.0649    2.1060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5056    2.7454    0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    3.7082    1.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.9888   -1.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -0.8670    0.2956 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3946   -0.6736    2.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1304   -0.6354    2.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0527    0.7180    1.7511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7370   -2.2595    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8383   -1.2640    0.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8817   -0.3185   -1.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    0.0389   -3.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -2.1072   -2.7134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934   -0.9840   -2.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3948   -3.1801    0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532   -3.6333   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573   -2.3218    1.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2377   -2.8219   -0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2591    2.3449   -0.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9516    2.7840   -0.8952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1732    1.6724   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2898   -0.7560   -0.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594   -2.0116    0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6752    4.7267    1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7252    3.6066    2.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0280    3.7020    2.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7777    1.7734   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    1.3665   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941   -1.1632    1.3284 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


  Mrv1652304282200152D          

 25 29  0  0  1  0            999 V2000
    2.4050   -1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9808   -0.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0359   -0.2350    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4310   -1.1245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7271   -1.8624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186   -2.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1734   -1.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -0.3913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7214   -0.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0057   -0.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4996   -0.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    0.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    1.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1070    0.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4310    1.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    0.2282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -0.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843   -1.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6324   -1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052   -0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0299    0.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  3 10  1  0  0  0  0
  9 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  1  0  0  0  0
  3 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 20 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=C[C@@H]2CN3CCC4=C(NC5=CC=CC=C45)[C@@](C2)([C@@H]13)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/t13-,19+,21-/m0/s1

> <INCHI_KEY>
CMKFQVZJOWHHDV-NQZBTDCJSA-N

> <FORMULA>
C21H24N2O2

> <MOLECULAR_WEIGHT>
336.435

> <EXACT_MASS>
336.183778021

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.773016121815324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]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>
7.486466578744898

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
98.71150000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8,16-pentaene-1-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  C   UNK     0       4.489  -2.056   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.698  -0.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.934  -0.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.805  -2.099   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.357  -3.476   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.648  -4.307   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.057  -3.609   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.728  -2.755   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.605  -0.730   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.213  -1.692   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.685  -0.121   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.348  -1.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.877  -1.473   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.799  -0.239   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.329   0.978   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.253   2.209   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.200   1.162   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.804   2.578   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.709   0.426   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.126  -0.177   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.990  -1.711   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.251  -2.596   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.647  -1.947   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.783  -0.413   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.522   0.472   0.000  0.00  0.00           C+0
CONECT    1    2    7   21                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   10   15                                             
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    3                                                       
CONECT   11    9   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20    1   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
Catharanthine sulfate, (2alpha,5beta,6alpha,18beta)-isomer	MeSH
Catharanthine monohydrochloride, (2alpha,5beta,6alpha,18beta)-isomer	MeSH

Chemical Formula

C₂₁H₂₄N₂O₂

Average Mass

336.4350 Da

Monoisotopic Mass

336.18378 Da

IUPAC Name

methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

Traditional Name

methyl (1R,15R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CCC1=C[C@@H]2CN3CCC4=C(NC5=CC=CC=C45)[C@@](C2)([C@@H]13)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/t13-,19+,21-/m0/s1

InChI Key

CMKFQVZJOWHHDV-NQZBTDCJSA-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
Catharanthus roseus	Plant	KNApSAcK
Catharanthus trichophyllus	LOTUS Database	35616633
Ervatamia coronaria	LOTUS Database	35616633
Tabernaemontana catharinensis	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
Piperidine
Benzenoid
Pyrrole
Methyl ester
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic nitrogen compound
Organonitrogen 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	37.77 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

C00001704

Chemspider ID

4572197

KEGG Compound ID

Not Available

BioCyc ID

CPD-7859

BiGG ID

Not Available

Wikipedia Link

Catharanthine

METLIN ID

Not Available

PubChem Compound

5458190

PDB ID

Not Available

ChEBI ID

3469

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 ]
Arias HR, Borghese CM, Germann AL, Pierce SR, Bonardi A, Nocentini A, Gratteri P, Thodati TM, Lim NJ, Harris RA, Akk G: (+)-Catharanthine potentiates the GABAA receptor by binding to a transmembrane site at the beta(+)/alpha(-) interface near the TM2-TM3 loop. Biochem Pharmacol. 2022 May;199:114993. doi: 10.1016/j.bcp.2022.114993. Epub 2022 Mar 15. [PubMed:35304861 ]
Yeshi K, Crayn D, Ritmejeryte E, Wangchuk P: Plant Secondary Metabolites Produced in Response to Abiotic Stresses Has Potential Application in Pharmaceutical Product Development. Molecules. 2022 Jan 5;27(1):313. doi: 10.3390/molecules27010313. [PubMed:35011546 ]
Chu C, Zang Y, Yang F, Zou Y, Li J, Liu EH, Yi T, Yan J, Tong S: A simple and sensitive preconcentration strategy by coupling salting-out assisted liquid-liquid extraction with online three-step stacking for the determination of potent anti-tumour compound vinblastine and its precursor in biological samples by capillary electrophoresis. J Chromatogr A. 2022 Feb 8;1664:462794. doi: 10.1016/j.chroma.2021.462794. Epub 2021 Dec 30. [PubMed:34998026 ]
Nakabayashi R, Takeda-Kamiya N, Yamada Y, Mori T, Uzaki M, Nirasawa T, Toyooka K, Saito K: A multimodal metabolomics approach using imaging mass spectrometry and liquid chromatography-tandem mass spectrometry for spatially characterizing monoterpene indole alkaloids secreted from roots. Plant Biotechnol (Tokyo). 2021 Sep 25;38(3):305-310. doi: 10.5511/plantbiotechnology.21.0504a. [PubMed:34782816 ]

Showing NP-Card for Catharanthine (NP0050850)

MOL for NP0050850 (Catharanthine)

3D MOL for NP0050850 (Catharanthine)

3D SDF for NP0050850 (Catharanthine)

3D-SDF for NP0050850 (Catharanthine)

PDB for NP0050850 (Catharanthine)

3D PDB for NP0050850 (Catharanthine)

SMILES for NP0050850 (Catharanthine)

INCHI for NP0050850 (Catharanthine)

Structure for NP0050850 (Catharanthine)

3D Structure for NP0050850 (Catharanthine)