NP-MRD: Showing NP-Card for Quinine (NP0010219)

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Record Information

Version

1.0

Created at

2021-01-05 19:48:51 UTC

Updated at

2021-07-15 17:05:29 UTC

NP-MRD ID

NP0010219

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinine

Provided By

NPAtlas

Description

Quinine, also known as chinin or (8S,9R)-quinine, belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety. Quinine is a drug which is used for the treatment of malaria and leg cramps. In humans, quinine is involved in the tamoxifen action pathway. Quinine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Quinine is found in Ciliosemina pedunculata, Cinchona ledgeriana, Diaporthe sp. and Festuca pratensis. It was first documented in 1994 (PMID: 8143397). Based on a literature review a significant number of articles have been published on Quinine (PMID: 21804259) (PMID: 10821711) (PMID: 10891117) (PMID: 10937718).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107363D          

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M  END

     RDKit          3D

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  Mrv1652306242107363D          

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 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
  8  3  1  0  0  0  0
 24 13  1  0  0  0  0
 10  5  1  0  0  0  0
 24 17  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  2 27  1  0  0  0  0
  3 28  1  1  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  8 35  1  6  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  6  0  0  0
 11 39  1  1  0  0  0
 12 40  1  0  0  0  0
 14 41  1  0  0  0  0
 15 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
 22 47  1  0  0  0  0
 23 48  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010219

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C1=C([H])C([H])=NC2=C([H])C([H])=C(OC([H])([H])[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/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1

> <INCHI_KEY>
LOUPRKONTZGTKE-WZBLMQSHSA-N

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.4168

> <EXACT_MASS>
324.183778022

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.98961107414211

> <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](6-methoxyquinolin-4-yl)methanol

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.513463950666668

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.892048067691277

> <JCHEM_PKA_STRONGEST_BASIC>
9.0455475118293

> <JCHEM_POLAR_SURFACE_AREA>
45.59

> <JCHEM_REFRACTIVITY>
94.6936

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quinine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
    6.1827    0.5106   -0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855    0.4990   -1.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.3798    0.0100 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9662    1.5941    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    1.1889    0.2814 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5435    0.3735    1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2629   -0.9348    1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9994   -0.8328   -0.1033 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0588   -0.6194   -1.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1348    0.5279   -0.9120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2748   -0.0334   -0.7328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6365   -0.6360   -1.9282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    1.0339   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595    2.3567   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8057    3.3019   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0534    2.9628    0.2261 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957    1.6560    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6835    1.2765    0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120   -0.0555    0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1188   -1.0675    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4471   -2.4151    0.4601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7578   -2.7813    0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8380   -0.6848    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    0.6512   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9481    0.5951   -1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5092    0.4280    0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862    0.5836   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4423    0.2602    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879    2.2438   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643    2.1813    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.2380    1.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059    0.9163    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718   -1.0992    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6206   -1.8141    1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6033   -1.7680   -0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032   -1.5388   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6641   -0.3189   -2.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    1.2670   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -0.8107    0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4633   -1.6054   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149    2.7061   -0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5776    4.3793   -0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3842    2.0655    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0154   -0.3513    1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4997   -2.5728    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731   -3.8834    1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0993   -2.2432    1.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -1.4199   -0.2250 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  1  0
 20 23  1  0
 23 24  2  0
  8  3  1  0
 24 13  1  0
 10  5  1  0
 24 17  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  1
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  6
 11 39  1  1
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  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       6.183   0.511  -0.824  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.886   0.499  -1.064  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.894   0.380   0.010  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.966   1.594   0.066  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.593   1.189   0.281  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.544   0.374   1.454  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.263  -0.935   1.232  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.999  -0.833  -0.103  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.059  -0.619  -1.254  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.135   0.528  -0.912  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.275  -0.033  -0.733  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.637  -0.636  -1.928  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.224   1.034  -0.400  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.860   2.357  -0.463  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.806   3.302  -0.141  0.00  0.00           C+0
HETATM   16  N   UNK     0      -3.053   2.963   0.226  0.00  0.00           N+0
HETATM   17  C   UNK     0      -3.396   1.656   0.283  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.684   1.276   0.663  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.012  -0.056   0.716  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.119  -1.067   0.407  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.447  -2.415   0.460  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.758  -2.781   0.850  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.838  -0.685   0.030  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.498   0.651  -0.027  0.00  0.00           C+0
HETATM   25  H   UNK     0       6.948   0.595  -1.564  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.509   0.428   0.210  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.586   0.584  -2.111  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.442   0.260   0.986  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.088   2.244  -0.828  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.264   2.181   0.974  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.516   0.238   1.856  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.106   0.916   2.257  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.072  -1.099   1.989  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.621  -1.814   1.279  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.603  -1.768  -0.225  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.503  -1.539  -1.525  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.664  -0.319  -2.129  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.123   1.267  -1.732  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.174  -0.811   0.047  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.463  -1.605  -1.959  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.115   2.706  -0.750  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.578   4.379  -0.174  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.384   2.066   0.905  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.015  -0.351   1.012  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.500  -2.573   0.046  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.773  -3.883   1.069  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.099  -2.243   1.763  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.089  -1.420  -0.225  0.00  0.00           H+0
CONECT    1    2   25   26                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4    8   28                                             
CONECT    4    3    5   29   30                                             
CONECT    5    4    6   10                                                  
CONECT    6    5    7   31   32                                             
CONECT    7    6    8   33   34                                             
CONECT    8    7    9    3   35                                             
CONECT    9    8   10   36   37                                             
CONECT   10    9   11    5   38                                             
CONECT   11   10   12   13   39                                             
CONECT   12   11   40                                                       
CONECT   13   11   14   24                                                  
CONECT   14   13   15   41                                                  
CONECT   15   14   16   42                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   43                                                  
CONECT   19   18   20   44                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   45   46   47                                             
CONECT   23   20   24   48                                                  
CONECT   24   23   13   17                                                  
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    2                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   22                                                            
CONECT   46   22                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  102    0
END

RDKit          3D

48 51  0  0  0  0  0  0  0  0999 V2000
    6.1827    0.5106   -0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8855    0.4990   -1.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8941    0.3798    0.0100 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9662    1.5941    0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925    1.1889    0.2814 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5435    0.3735    1.4536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2629   -0.9348    1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9994   -0.8328   -0.1033 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0588   -0.6194   -1.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1348    0.5279   -0.9120 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2748   -0.0334   -0.7328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6365   -0.6360   -1.9282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2245    1.0339   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595    2.3567   -0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8057    3.3019   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0534    2.9628    0.2261 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957    1.6560    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6835    1.2765    0.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120   -0.0555    0.7162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1188   -1.0675    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4471   -2.4151    0.4601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7578   -2.7813    0.8504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8380   -0.6848    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    0.6512   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9481    0.5951   -1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5092    0.4280    0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862    0.5836   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4423    0.2602    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0879    2.2438   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643    2.1813    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5160    0.2380    1.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1059    0.9163    2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718   -1.0992    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6206   -1.8141    1.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6033   -1.7680   -0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032   -1.5388   -1.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6641   -0.3189   -2.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226    1.2670   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1744   -0.8107    0.0474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4633   -1.6054   -1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149    2.7061   -0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5776    4.3793   -0.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3842    2.0655    0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0154   -0.3513    1.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4997   -2.5728    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731   -3.8834    1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0993   -2.2432    1.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -1.4199   -0.2250 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  1  0
 20 23  1  0
 23 24  2  0
  8  3  1  0
 24 13  1  0
 10  5  1  0
 24 17  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  1
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  6
 11 39  1  1
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(-)-Quinine	ChEBI
(8S,9R)-Quinine	ChEBI
(R)-(-)-Quinine	ChEBI
(R)-(6-Methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methanol	ChEBI
6'-Methoxycinchonidine	ChEBI
Chinin	ChEBI
Chinine	ChEBI
Chininum	ChEBI
Quinina	ChEBI
Myoquin	HMDB
Surquina	HMDB
Biquinate	HMDB
Quinimax	HMDB
Quinine bisulfate	HMDB
Quinine sulfate	HMDB
Quinoctal	HMDB
Quinson	HMDB
Quinsul	HMDB
Bisulfate, quinine	HMDB
Hydrochloride, quinine	HMDB
Legatrim	HMDB
Quinamm	HMDB
Quinbisan	HMDB
Quinbisul	HMDB
Quinine lafran	HMDB
Quinine sulphate	HMDB
Quinine-odan	HMDB
Sulfate, quinine	HMDB
Sulphate, quinine	HMDB
Quindan	HMDB
Quinine hydrochloride	HMDB
Strema	HMDB
6'-Methoxycinchonine	HMDB
Quinine, anhydrous	HMDB
Quinineanhydrous	HMDB
Quinoline alkaloid	HMDB
Aventis brand OF quinine bisulfate	HMDB
Fawns and mcallan brand OF quinine sulfate	HMDB
Foy brand OF quinine sulfate	HMDB
Plough brand OF quinine sulfate	HMDB
Fawns and mcallan brand OF quinine bisulfate	HMDB
Hoechst brand OF quinine sulfate	HMDB
Lafran brand OF quinine hydrochloride	HMDB
Alphapharm brand OF quinine sulfate	HMDB
Innotech brand OF quinine hydrochloride	HMDB
Odan brand OF quinine sulfate	HMDB
Prosana brand OF quinine bisulfate	HMDB

Chemical Formula

C₂₀H₂₄N₂O₂

Average Mass

324.4168 Da

Monoisotopic Mass

324.18378 Da

IUPAC Name

(R)-[(1S,2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol

Traditional Name

quinine

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=CN=C2C=C1)[C@@H](O)[C@@H]1C[C@@H]2CCN1C[C@@H]2C=C

InChI Identifier

InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1

InChI Key

LOUPRKONTZGTKE-WZBLMQSHSA-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
Ciliosemina pedunculata	LOTUS Database	35616633
Cinchona calisaya	Plant	KNApSAcK
Cinchona ledgariana	KNApSAcK Database	22123792
Cinchona ledgeriana	KNApSAcK Database	22123792
Cinchona officinalis	KNApSAcK Database	22123792
Cinchona pelletierana Wedd.	KNApSAcK Database	22123792
Cinchona pubescens	KNApSAcK Database	22123792
Cinchona robusta	KNApSAcK Database	22123792
Cinchona rosulenta	KNApSAcK Database	22123792
Cinchona sp.	KNApSAcK Database	22123792
Cinchona spp.	KNApSAcK Database	22123792
Cinchona succirubra	KNApSAcK Database	22123792
Diaporthe sp.	NPAtlas	21804259
Lolium pratense	LOTUS Database	35616633
Remijia pedunculata	KNApSAcK Database	22123792
Remijia peruviana	KNApSAcK Database	22123792

Species Where Detected

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]Octane moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cinchona alkaloids

Sub Class

Not Available

Direct Parent

Cinchona alkaloids

Alternative Parents

Not Available

Substituents

Not Available

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	2.82	ALOGPS
logP	2.51	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	9.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.69 m³·mol⁻¹	ChemAxon
Polarizability	35.99 Å³	ChemAxon
Number of Rings	4	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

NPAtlas ID

NPA000031

HMDB ID

HMDB0014611

DrugBank ID

DB00468

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quinine

METLIN ID

Not Available

PubChem Compound

3034034

PDB ID

Not Available

ChEBI ID

15854

Good Scents ID

rw1108861

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 ]
Paintaud G, Alvan G, Berninger E, Gustafsson LL, Idrizbegovic E, Karlsson KK, Wakelkamp M: The concentration-effect relationship of quinine-induced hearing impairment. Clin Pharmacol Ther. 1994 Mar;55(3):317-23. doi: 10.1038/clpt.1994.32. [PubMed:8143397 ]
Frostell-Karlsson A, Remaeus A, Roos H, Andersson K, Borg P, Hamalainen M, Karlsson R: Biosensor analysis of the interaction between immobilized human serum albumin and drug compounds for prediction of human serum albumin binding levels. J Med Chem. 2000 May 18;43(10):1986-92. doi: 10.1021/jm991174y. [PubMed:10821711 ]
Yoshida F, Topliss JG: QSAR model for drug human oral bioavailability. J Med Chem. 2000 Jun 29;43(13):2575-85. doi: 10.1021/jm0000564. [PubMed:10891117 ]
Itoh T, Shirakami S, Ishida N, Yamashita Y, Yoshida T, Kim HS, Wataya Y: Synthesis of novel ferrocenyl sugars and their antimalarial activities. Bioorg Med Chem Lett. 2000 Aug 7;10(15):1657-9. doi: 10.1016/s0960-894x(00)00313-9. [PubMed:10937718 ]

Showing NP-Card for Quinine (NP0010219)

MOL for NP0010219 (Quinine)

3D MOL for NP0010219 (Quinine)

3D SDF for NP0010219 (Quinine)

3D-SDF for NP0010219 (Quinine)

PDB for NP0010219 (Quinine)

3D PDB for NP0010219 (Quinine)

SMILES for NP0010219 (Quinine)

INCHI for NP0010219 (Quinine)

Structure for NP0010219 (Quinine)

3D Structure for NP0010219 (Quinine)