NP-MRD: Showing NP-Card for (-)-Coronaridine (NP0050854)

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Record Information

Version

2.0

Created at

2022-04-27 22:15:51 UTC

Updated at

2022-04-27 22:15:51 UTC

NP-MRD ID

NP0050854

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Coronaridine

Description

(-)-Coronaridine 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 (-)-coronaridine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (-)-Coronaridine is found in Catharanthus roseus , Tabernaemontana divaricata, Ervatamia divaricata Gouyahua, Tabernaemontana bufalina, Pandaca mocquerysii, Peschiera affinis, Tabernaemontana grandiflora, Stemmadenia obovata Benth, Tabernaemontana africana, Tabernaemontana alternifolia, Tabernaemontana calcarea, Tabernaemontana catharinensis, Tabernaemontana citrifolia, Tabernaemontana coronaria , Tabernaemontana corymbosa, Tabernaemontana cymosa, Tabernaemontana eglandulosa, Tabernaemontana glandulosa, Tabernaemontana heyneana , Tabernaemontana hystrix, Tabernaemontana laeta, Tabernaemontana litoralis, Tabernaemontana macrocalyx, Tabernaemontana markgrafiana, Tabernaemontana odontadeniiflora, Tabernaemontana oppositifolia, Tabernaemontana pandacaqui, Tabernaemontana pauciflora, Tabernaemontana peduncularis, Tabernaemontana penduliflora, Tabernaemontana solanifolia, Tabernaemontana undulata, Tabernaemontana vanheurckii, Tabernanthe iboga , Trachelospermum jasminoides and Voacanga africana. (-)-Coronaridine was first documented in 2020 (PMID: 33375687). Based on a literature review a small amount of articles have been published on (-)-coronaridine (PMID: 35366775) (PMID: 35304861) (PMID: 34047097) (PMID: 33321518).

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
    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
    1.0359   -0.2350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4310   -1.1245    0.0000 C   0  0  1  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  1  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  2  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
   -1.3310   -1.5471    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 10 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 10 22  1  1  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

 51 55  0  0  0  0  0  0  0  0999 V2000
   -4.8181   -1.4917   -0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3505   -1.4956   -0.6749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6638   -0.2183   -0.1938 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8323   -0.1785    1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4988    0.0360    2.0234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5667   -1.1455    1.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8285   -1.5633    0.4174 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0659   -2.4944   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2408   -1.9340   -0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103   -0.6399   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.4908   -0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9789    1.3859    0.3535 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204    0.8591    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    1.3213    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6053    0.5346    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4794   -0.7687   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944   -1.2165   -0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0839   -0.4233   -0.2154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046    0.7511   -0.0284 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6424    1.8468   -0.9889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3770    1.6482   -1.9790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743    3.0975   -0.8286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685    4.1759   -1.7144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    1.2444    1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683   -0.4574   -0.4559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3550   -0.9742   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1556   -2.5470   -0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0274   -1.0995    0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -2.3327   -0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2786   -1.6196   -1.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0485    0.6728   -0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469   -1.1205    1.7197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4846    0.6639    1.6211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7117    0.1842    3.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.9640    2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -0.8126    1.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664   -3.1377    0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -3.2046   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0338   -2.7050   -0.9175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -1.7799   -1.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8272    2.3631    0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6283    2.3227    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6240    0.8807    0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3518   -1.3987   -0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1033   -2.2301   -0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2426    4.7015   -1.5007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190    4.9373   -1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1950    3.8644   -2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    1.6624    1.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6989    1.9909    1.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620   -0.6824   -1.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  6
 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
  3 31  1  6
  4 32  1  0
  4 33  1  0
  5 34  1  1
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 12 41  1  0
 14 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  6
 23 46  1  0
 23 47  1  0
 23 48  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
    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
    1.0359   -0.2350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4310   -1.1245    0.0000 C   0  0  1  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  1  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  2  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
   -1.3310   -1.5471    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  2  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 10 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 10 22  1  1  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>
NP0050854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C[C@H]2CN3CCC4=C(NC5=CC=CC=C45)[C@](C2)([C@H]13)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O2/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/h4-7,13-14,19,22H,3,8-12H2,1-2H3/t13-,14+,19+,21-/m1/s1

> <INCHI_KEY>
NVVDQMVGALBDGE-PZXGUROGSA-N

> <FORMULA>
C21H26N2O2

> <MOLECULAR_WEIGHT>
338.451

> <EXACT_MASS>
338.199428085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.353847964228876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.03

> <JCHEM_LOGP>
3.518868694

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.378598874003423

> <JCHEM_PKA_STRONGEST_BASIC>
8.561564798139825

> <JCHEM_POLAR_SURFACE_AREA>
45.33

> <JCHEM_REFRACTIVITY>
97.9385

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-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  N   UNK     0       4.709   0.426   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.126  -0.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.990  -1.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.251  -2.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.647  -1.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.783  -0.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.522   0.472   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.934  -0.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.805  -2.099   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.357  -3.476   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.648  -4.307   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.057  -3.609   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.728  -2.755   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.605  -0.730   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.213  -1.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.685  -0.121   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.348  -1.291   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.877  -1.473   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.485  -2.888   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.329   0.978   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.253   2.209   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.200   1.162   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.804   2.578   0.000  0.00  0.00           C+0
CONECT    1    2    5   14                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11   17   22                                             
CONECT   11   10   12   19                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    1                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   10                                                       
CONECT   18   16   19                                                       
CONECT   19   18   11   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   10   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
Coronaridine	ChEBI
Coronardine	MeSH
Coronardine monohydrochloride	MeSH
Coronardine monohydrochloride, (+-)-isomer	MeSH

Chemical Formula

C₂₁H₂₆N₂O₂

Average Mass

338.4510 Da

Monoisotopic Mass

338.19943 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC[C@H]1C[C@H]2CN3CCC4=C(NC5=CC=CC=C45)[C@](C2)([C@H]13)C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O2/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/h4-7,13-14,19,22H,3,8-12H2,1-2H3/t13-,14+,19+,21-/m1/s1

InChI Key

NVVDQMVGALBDGE-PZXGUROGSA-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
Ervatamia coronaria	LOTUS Database	35616633
Ervatamia divaricata Gouyahua	Plant	KNApSAcK
Ervatamia hainanensis	LOTUS Database	35616633
Pandaca mocquerysii	Plant	KNApSAcK
Peschiera affinis	Plant	KNApSAcK
Stemmadenia grandiflora	LOTUS Database	35616633
Stemmadenia obovata Benth	Plant	KNApSAcK
Tabernaemontana africana	LOTUS Database	35616633
Tabernaemontana alternifolia	LOTUS Database	35616633
Tabernaemontana calcarea	Plant	KNApSAcK
Tabernaemontana catharinensis	Plant	KNApSAcK
Tabernaemontana citrifolia	LOTUS Database	35616633
Tabernaemontana coronaria Br.(Ervatamia coronaria.)	Plant	KNApSAcK
Tabernaemontana corymbosa	LOTUS Database	35616633
Tabernaemontana cymosa	LOTUS Database	35616633
Tabernaemontana eglandulosa	LOTUS Database	35616633
Tabernaemontana glandulosa	LOTUS Database	35616633
Tabernaemontana heyneana	Plant	KNApSAcK
Tabernaemontana hystrix	LOTUS Database	35616633
Tabernaemontana laeta Mart.	LOTUS Database	35616633
Tabernaemontana litoralis	Plant	KNApSAcK
Tabernaemontana macrocalyx	LOTUS Database	35616633
Tabernaemontana markgrafiana	Plant	KNApSAcK
Tabernaemontana odontadeniiflora	LOTUS Database	35616633
Tabernaemontana oppositifolia	Plant	KNApSAcK
Tabernaemontana pandacaqui	LOTUS Database	35616633
Tabernaemontana pauciflora	LOTUS Database	35616633
Tabernaemontana peduncularis	LOTUS Database	35616633
Tabernaemontana penduliflora	Plant	KNApSAcK
Tabernaemontana solanifolia	LOTUS Database	35616633
Tabernaemontana undulata	LOTUS Database	35616633
Tabernaemontana vanheurckii	LOTUS Database	35616633
Tabernanthe iboga	Plant	KNApSAcK
Trachelospermum jasminoides	LOTUS Database	35616633
Voacanga africana	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	4.03	ALOGPS
logP	3.52	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	16.38	ChemAxon
pKa (Strongest Basic)	8.56	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	97.94 m³·mol⁻¹	ChemAxon
Polarizability	38.35 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

C00001709

Chemspider ID

4932328

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coronaridine

METLIN ID

Not Available

PubChem Compound

6426909

PDB ID

Not Available

ChEBI ID

3887

Good Scents ID

Not Available

References

General References

Babiaka SB, Simoben CV, Abuga KO, Mbah JA, Karpoormath R, Ongarora D, Mugo H, Monya E, Cho-Ngwa F, Sippl W, Loveridge EJ, Ntie-Kang F: Alkaloids with Anti-Onchocercal Activity from Voacanga africana Stapf (Apocynaceae): Identification and Molecular Modeling. Molecules. 2020 Dec 25;26(1). pii: molecules26010070. doi: 10.3390/molecules26010070. [PubMed:33375687 ]
Jothimani G, Ganesan H, Pathak S, Banerjee A: Molecular characterization of primary and metastatic colon cancer cells to identify therapeutic targets with natural compounds. Curr Top Med Chem. 2022 Apr 1. pii: CTMC-EPUB-122190. doi: 10.2174/1568026622666220401161511. [PubMed:35366775 ]
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 ]
Li ZW, Sang CC, Sun B, Tian HY, Zhang XQ, Ye WC: [A new alkaloid from Ervatamia hainanensis]. Zhongguo Zhong Yao Za Zhi. 2021 May;46(10):2509-2513. doi: 10.19540/j.cnki.cjcmm.20210125.602. [PubMed:34047097 ]
Musquiari B, Crevelin EJ, Bertoni BW, Franca SC, Pereira AMS, Castello ACD, Castillo-Ordonez WO, Giuliatti S, Lopes AA: Precursor-directed Biosynthesis in Tabernaemontana catharinensis as a New Avenue for Alzheimer's Disease-modifying Agents. Planta Med. 2021 Feb;87(1-02):136-147. doi: 10.1055/a-1315-2282. Epub 2020 Dec 15. [PubMed:33321518 ]

Showing NP-Card for (-)-Coronaridine (NP0050854)

MOL for NP0050854 ((-)-Coronaridine)

3D MOL for NP0050854 ((-)-Coronaridine)

3D SDF for NP0050854 ((-)-Coronaridine)

3D-SDF for NP0050854 ((-)-Coronaridine)

PDB for NP0050854 ((-)-Coronaridine)

3D PDB for NP0050854 ((-)-Coronaridine)

SMILES for NP0050854 ((-)-Coronaridine)

INCHI for NP0050854 ((-)-Coronaridine)

Structure for NP0050854 ((-)-Coronaridine)

3D Structure for NP0050854 ((-)-Coronaridine)