NP-MRD: Showing NP-Card for Cinchonidine (NP0010217)

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Record Information

Version

2.0

Created at

2021-01-05 19:48:47 UTC

Updated at

2024-09-03 04:16:50 UTC

NP-MRD ID

NP0010217

Natural Product DOI

https://doi.org/10.57994/0828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cinchonidine

Provided By

NPAtlas

Description

CINCHONIDINE is also known as alpha-quinidine or cinchovatine. CINCHONIDINE 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. Cinchonidine is found in Cinchona ledgeriana, Cinchona pubescens and Diaporthe sp.. Cinchonidine was first documented in 2011 (PMID: 21804259). Based on a literature review a small amount of articles have been published on CINCHONIDINE (PMID: 34295874) (PMID: 34199504) (PMID: 34164076) (PMID: 34073082).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106563D          

 44 47  0  0  0  0            999 V2000
   -4.1620   -2.9543   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -2.1474   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227   -0.8613    0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3154   -0.7804    1.7218 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.9986    1.5689    1.4226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1914    1.5336    0.4567 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.8374    1.7485    0.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.1410   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1878   -1.5779   -2.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568   -1.1549   -2.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951   -0.2286   -1.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7417    1.1127   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9254    1.6283    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003    1.2004    0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.2831   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0355    1.6302    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
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M  END

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.1620   -2.9543   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -2.1474   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3154   -0.7804    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373    0.3032    1.5475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9986    1.5689    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1878   -1.5779   -2.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3
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M  END


  Mrv1652306242106563D          

 44 47  0  0  0  0            999 V2000
   -4.1620   -2.9543   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -2.1474   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227   -0.8613    0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3154   -0.7804    1.7218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3373    0.3032    1.5475 N   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9986    1.5689    1.4226 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.0429    0.2831   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3  0  0  0
  2  3  1  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  8  1  0  0  0  0
  8  9  1  0  0  0  0
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  8  3  1  0  0  0  0
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 10  5  1  0  0  0  0
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  1 23  1  0  0  0  0
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  7 31  1  0  0  0  0
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  8 33  1  6  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
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 20 43  1  0  0  0  0
 21 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C1=C([H])C([H])=NC2=C([H])C([H])=C([H])C([H])=C12)[C@@]1([H])[N@]2C([H])([H])C([H])([H])[C@@]([H])(C1([H])[H])[C@@]([H])(C([H])=C([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1

> <INCHI_KEY>
KMPWYEUPVWOPIM-KODHJQJWSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.398

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
33.55416244494915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.6711352163333344

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.877315843243736

> <JCHEM_PKA_STRONGEST_BASIC>
9.146374717755835

> <JCHEM_POLAR_SURFACE_AREA>
36.36

> <JCHEM_REFRACTIVITY>
88.23040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinchonidine

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.1620   -2.9543   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -2.1474   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227   -0.8613    0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3154   -0.7804    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373    0.3032    1.5475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9986    1.5689    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914    1.5336    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8693    0.3396   -0.4557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3787    0.4903   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5860   -0.0904    0.3384 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8449    0.3904    0.4481 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8374    1.7485    0.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.1410   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -1.0991   -1.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -1.5779   -2.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568   -1.1549   -2.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951   -0.2286   -1.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2093    0.1832   -1.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417    1.1127   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9254    1.6283    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003    1.2004    0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.2831   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0474   -2.6397    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812   -3.9056   -0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -2.5177   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972   -0.6803    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -0.5042    2.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -1.6972    1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3427    1.8692    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    2.3499    1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0733    1.2515    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2929    2.4621   -0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    0.2768   -1.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2330    0.1146   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844    1.6016   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -1.2032    0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -0.0653    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8748    2.1232    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373   -1.4746   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7819   -2.3298   -3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8473   -0.2307   -2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7566    1.4655   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3030    2.3567    0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    1.6302    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  8  3  1  0
 22 13  1  0
 10  5  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 14 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.162  -2.954  -0.234  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.111  -2.147  -0.228  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.123  -0.861   0.466  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.315  -0.780   1.722  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.337   0.303   1.548  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.999   1.569   1.423  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.191   1.534   0.457  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.869   0.340  -0.456  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.379   0.490  -0.780  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.586  -0.090   0.338  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.845   0.390   0.448  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.837   1.749   0.507  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.745  -0.141  -0.570  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.343  -1.099  -1.501  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.188  -1.578  -2.449  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.457  -1.155  -2.540  0.00  0.00           N+0
HETATM   17  C   UNK     0       3.895  -0.229  -1.659  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.209   0.183  -1.762  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.742   1.113  -0.899  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.925   1.628   0.083  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.600   1.200   0.171  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.043   0.283  -0.669  0.00  0.00           C+0
HETATM   23  H   UNK     0      -5.047  -2.640   0.295  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.181  -3.906  -0.737  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.238  -2.518  -0.786  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.197  -0.680   0.803  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.894  -0.504   2.627  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.716  -1.697   1.920  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.343   1.869   2.436  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.349   2.350   1.055  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.073   1.252   1.049  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.293   2.462  -0.109  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.505   0.277  -1.331  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.233   0.115  -1.780  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.184   1.602  -0.823  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.622  -1.203   0.312  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.182  -0.065   1.448  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.875   2.123   1.430  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.337  -1.475  -1.440  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.782  -2.330  -3.140  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.847  -0.231  -2.542  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.757   1.466  -0.938  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.303   2.357   0.778  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.035   1.630   0.964  0.00  0.00           H+0
CONECT    1    2   23   24                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4    8   26                                             
CONECT    4    3    5   27   28                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    7   29   30                                             
CONECT    7    6    8   31   32                                             
CONECT    8    7    9    3   33                                             
CONECT    9    8   10   34   35                                             
CONECT   10    9   11    5   36                                             
CONECT   11   10   12   13   37                                             
CONECT   12   11   38                                                       
CONECT   13   11   14   22                                                  
CONECT   14   13   15   39                                                  
CONECT   15   14   16   40                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   41                                                  
CONECT   19   18   20   42                                                  
CONECT   20   19   21   43                                                  
CONECT   21   20   22   44                                                  
CONECT   22   21   13   17                                                  
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    2                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    6                                                            
CONECT   30    6                                                            
CONECT   31    7                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   21                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

RDKit          3D

44 47  0  0  0  0  0  0  0  0999 V2000
   -4.1620   -2.9543   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1111   -2.1474   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1227   -0.8613    0.4664 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3154   -0.7804    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373    0.3032    1.5475 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9986    1.5689    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1914    1.5336    0.4567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8693    0.3396   -0.4557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3787    0.4903   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5860   -0.0904    0.3384 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8449    0.3904    0.4481 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8374    1.7485    0.5072 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -0.1410   -0.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -1.0991   -1.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -1.5779   -2.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4568   -1.1549   -2.5396 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951   -0.2286   -1.6589 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2093    0.1832   -1.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7417    1.1127   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9254    1.6283    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6003    1.2004    0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0429    0.2831   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0474   -2.6397    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1812   -3.9056   -0.7369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -2.5177   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972   -0.6803    0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8938   -0.5042    2.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7158   -1.6972    1.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3427    1.8692    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    2.3499    1.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0733    1.2515    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2929    2.4621   -0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    0.2768   -1.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2330    0.1146   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844    1.6016   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6223   -1.2032    0.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -0.0653    1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8748    2.1232    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3373   -1.4746   -1.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7819   -2.3298   -3.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8473   -0.2307   -2.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7566    1.4655   -0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3030    2.3567    0.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    1.6302    0.9635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  8  3  1  0
 22 13  1  0
 10  5  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  1
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  6
 11 37  1  1
 12 38  1  0
 14 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Cinchonidine	ChEBI
(8alpha,9R)-Cinchonan-9-ol	ChEBI
(8S,9R)-Cinchonan-9-ol	ChEBI
(8S,9R)-Cinchonidine	ChEBI
(R)-[(4S,5S,7S)-5-Ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-quinolin-4-ylmethanol	ChEBI
alpha-Quinidine	ChEBI
Cinchovatine	ChEBI
L-Cinchonidine	ChEBI
(8a,9R)-Cinchonan-9-ol	Generator
(8Α,9R)-cinchonan-9-ol	Generator
a-Quinidine	Generator
Α-quinidine	Generator
Cinchonidine hydrochloride	MeSH
Cinchonidine monohydrochloride	MeSH
Cinchonidine sulfate(2:1)	MeSH
Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomer	MeSH

Chemical Formula

C₁₉H₂₂N₂O

Average Mass

294.3980 Da

Monoisotopic Mass

294.17321 Da

IUPAC Name

(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

Traditional Name

cinchonidine

CAS Registry Number

Not Available

SMILES

O[C@@H]([C@@H]1C[C@@H]2CCN1C[C@@H]2C=C)C1=CC=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1

InChI Key

KMPWYEUPVWOPIM-KODHJQJWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-10-20	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
HOMO2DJ NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCL3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-08-23	View Spectrum

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
Cinchona calisaya	Plant	KNApSAcK
Cinchona ledgeriana	KNApSAcK Database	22123792
Cinchona officinalis	KNApSAcK Database	22123792
Cinchona pubescens	LOTUS Database	35616633
Cinchona robusta	KNApSAcK Database	22123792
Cinchona succirubra	KNApSAcK Database	22123792
Cinchona tucujensis	KNApSAcK Database	22123792
Diaporthe sp.	NPAtlas	21804259
Ligustrum vulgare	KNApSAcK Database	22123792
Olea europaea	KNApSAcK Database	22123792
Olea europea L.	KNApSAcK Database	22123792
Remijia spp.	KNApSAcK Database	22123792

Species Where Detected

Species Name	Source	Reference
Diaporthe sp. CLF-J	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	3.2	ALOGPS
logP	2.67	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.23 m³·mol⁻¹	ChemAxon
Polarizability	33.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009420

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002147

Chemspider ID

91930

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101744

PDB ID

Not Available

ChEBI ID

3703

Good Scents ID

rw1136691

References

General References

Maehara S, Simanjuntak P, Kitamura C, Ohashi K, Shibuya H: Cinchona alkaloids are also produced by an endophytic filamentous fungus living in cinchona plant. Chem Pharm Bull (Tokyo). 2011;59(8):1073-4. doi: 10.1248/cpb.59.1073. [PubMed:21804259 ]
Ullah Z, Kim K, Venkanna A, Kim HS, Kim MI, Kim MH: Plausible Pnicogen Bonding of epi-Cinchonidine as a Chiral Scaffold in Catalysis. Front Chem. 2021 Jul 6;9:669515. doi: 10.3389/fchem.2021.669515. eCollection 2021. [PubMed:34295874 ]
Maftei CV, Franz MH, Kleeberg C, Neda I: New Members of the Cinchona Alkaloids Family: Assembly of the Triazole Heterocycle at the 6' Position. Molecules. 2021 Jun 2;26(11). pii: molecules26113357. doi: 10.3390/molecules26113357. [PubMed:34199504 ]
Sarkar R, Mukherjee S: Iridium-catalyzed enantioselective olefinic C(sp(2))-H allylic alkylation. Chem Sci. 2021 Jan 15;12(8):3070-3075. doi: 10.1039/d0sc06208a. [PubMed:34164076 ]
Ramic A, Skocibusic M, Odzak R, Cipak Gasparovic A, Milkovic L, Mikelic A, Sovic K, Primozic I, Hrenar T: Antimicrobial Activity of Quasi-Enantiomeric Cinchona Alkaloid Derivatives and Prediction Model Developed by Machine Learning. Antibiotics (Basel). 2021 May 31;10(6). pii: antibiotics10060659. doi: 10.3390/antibiotics10060659. [PubMed:34073082 ]

Showing NP-Card for Cinchonidine (NP0010217)

MOL for NP0010217 (Cinchonidine)

3D MOL for NP0010217 (Cinchonidine)

3D SDF for NP0010217 (Cinchonidine)

3D-SDF for NP0010217 (Cinchonidine)

PDB for NP0010217 (Cinchonidine)

3D PDB for NP0010217 (Cinchonidine)

SMILES for NP0010217 (Cinchonidine)

INCHI for NP0010217 (Cinchonidine)

Structure for NP0010217 (Cinchonidine)

3D Structure for NP0010217 (Cinchonidine)