NP-MRD: Showing NP-Card for Quinidine (NP0002764)

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Record Information

Version

1.0

Created at

2020-11-23 19:39:50 UTC

Updated at

2021-08-19 23:59:20 UTC

NP-MRD ID

NP0002764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinidine

Provided By

NPAtlas

Description

Quinidine, also known as chinidin or (8R,9S)-quinidine, 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. Quinidine is a drug which is used for the treatment of ventricular pre-excitation and cardiac dysrhythmias. In humans, quinidine is involved in the quinidine action pathway. Quinidine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Quinidine is found in Aspidosperma marcgravianum, Ciliosemina pedunculata, Cinchona ledgeriana, Cinchona succirubra and Diaporthe sp.. It was first documented in 2002 (PMID: 12477351). Based on a literature review a significant number of articles have been published on Quinidine (PMID: 17984079) (PMID: 12699389) (PMID: 14971904) (PMID: 14973303).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


     RDKit          2D

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M  END

     RDKit          3D

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     RDKit          2D

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M  END
> <DATABASE_ID>
NP0002764

> <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-LHHVKLHASA-N

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.4168

> <EXACT_MASS>
324.183778022

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.637860532780316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(S)-[(2R,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>
9.045547511829296

> <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>
quinidine

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
    5.9601    0.9960   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7047    0.6331   -1.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632    0.5887   -0.0991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5570    1.4812   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761    0.9346    0.3918 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9300    0.4846    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -0.8218    1.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119   -0.8285    0.0807 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0420   -0.9396   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -0.2574   -0.2097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3053   -0.1583   -1.0443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7880   -1.2907   -1.6141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535    0.9403   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9581    2.2855   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    3.1901   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1793    2.8946   -0.6129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    1.5868   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7160    1.2855    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9803   -0.0110    0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191   -0.9764    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892   -2.2795    1.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3834   -2.6947    1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -0.6707    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5184    0.6273   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091    1.0534   -1.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3120    1.2628    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944    0.3737   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794    0.8319    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784    2.4293    0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123    1.6311   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.2979    2.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170    1.2147    2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5616   -0.8811    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0677   -1.7198    1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455   -1.6094   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567   -1.9761   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.3953   -1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -0.9676    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242    0.3181   -2.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023   -1.0851   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259    2.5943   -1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7334    4.2689   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4849    2.0290    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9436   -0.2321    1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2061   -2.2623    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4645   -3.8055    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260   -2.2860    2.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962   -1.3941    0.1041 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  1
  9 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  6
 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       5.960   0.996  -1.011  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.705   0.633  -1.228  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.763   0.589  -0.099  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.557   1.481  -0.300  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.376   0.935   0.392  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.930   0.485   1.704  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.656  -0.822   1.502  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.212  -0.829   0.081  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.042  -0.940  -0.911  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.897  -0.257  -0.210  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.305  -0.158  -1.044  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.788  -1.291  -1.614  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.254   0.940  -0.759  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.958   2.285  -1.113  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.026   3.190  -1.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -3.179   2.895  -0.613  0.00  0.00           N+0
HETATM   17  C   UNK     0      -3.498   1.587  -0.256  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.716   1.286   0.274  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.980  -0.011   0.754  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.019  -0.976   0.689  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.189  -2.280   1.163  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.383  -2.695   1.788  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.777  -0.671   0.141  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.518   0.627  -0.338  0.00  0.00           C+0
HETATM   25  H   UNK     0       6.709   1.053  -1.796  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.312   1.263   0.001  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.394   0.374  -2.220  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.279   0.832   0.865  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.778   2.429   0.234  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.312   1.631  -1.385  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.070   0.298   2.397  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.617   1.215   2.134  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.562  -0.881   2.176  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.068  -1.720   1.739  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.946  -1.609  -0.098  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.757  -1.976  -1.116  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.277  -0.395  -1.871  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.671  -0.968   0.671  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.224   0.318  -2.033  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.202  -1.085  -2.492  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.026   2.594  -1.438  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.733   4.269  -1.285  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.485   2.029   0.339  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.944  -0.232   1.192  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.206  -2.262   1.212  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.465  -3.805   1.833  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.426  -2.286   2.842  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.996  -1.394   0.104  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
    5.9601    0.9960   -1.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7047    0.6331   -1.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7632    0.5887   -0.0991 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5570    1.4812   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3761    0.9346    0.3918 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9300    0.4846    1.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555   -0.8218    1.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2119   -0.8285    0.0807 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0420   -0.9396   -0.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -0.2574   -0.2097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3053   -0.1583   -1.0443 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7880   -1.2907   -1.6141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535    0.9403   -0.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9581    2.2855   -1.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    3.1901   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1793    2.8946   -0.6129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    1.5868   -0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7160    1.2855    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9803   -0.0110    0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0191   -0.9764    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1892   -2.2795    1.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3834   -2.6947    1.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770   -0.6707    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5184    0.6273   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091    1.0534   -1.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3120    1.2628    0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944    0.3737   -2.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794    0.8319    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784    2.4293    0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123    1.6311   -1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.2979    2.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170    1.2147    2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5616   -0.8811    2.1765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0677   -1.7198    1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455   -1.6094   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7567   -1.9761   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.3953   -1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -0.9676    0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2242    0.3181   -2.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023   -1.0851   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259    2.5943   -1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7334    4.2689   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4849    2.0290    0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9436   -0.2321    1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2061   -2.2623    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4645   -3.8055    1.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4260   -2.2860    2.8417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9962   -1.3941    0.1041 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  1
  9 36  1  0
  9 37  1  0
 10 38  1  1
 11 39  1  6
 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
(+)-Quinidine	ChEBI
(8R,9S)-Quinidine	ChEBI
(R)-(6-Methoxyquinolin-4-yl)((3S,4R,7S)-3-vinylquinuclidin-7-yl)methanol	ChEBI
(S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol	ChEBI
(S)-(6-Methoxyquinolin-4-yl)((2R,5R)-5-vinylquinuclidin-2-yl)methanol	ChEBI
6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol	ChEBI
alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol	ChEBI
beta-Quinine	ChEBI
Chinidin	ChEBI
Chinidinum	ChEBI
CIN-quin	ChEBI
Conchinin	ChEBI
Conquinine	ChEBI
Kinidin	ChEBI
Pitayine	ChEBI
Quinidina	ChEBI
6-Methoxy-a-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol	Generator
6-Methoxy-α-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol	Generator
a-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol	Generator
Α-(6-methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol	Generator
b-Quinine	Generator
Β-quinine	Generator
Quinidine sulfate	HMDB
Quincardine	HMDB
Sulfate, quinidine	HMDB
Apo-quinidine	HMDB
Apotex brand OF quinidine sulfate	HMDB
Fawns and mcallan brand OF quinidine sulfate	HMDB
Apo quinidine	HMDB
Quinidex	HMDB
Quinora	HMDB
Robins brand OF quinidine sulfate	HMDB
Adaquin	HMDB
Nelson brand OF quinidine sulfate	HMDB

Chemical Formula

C₂₀H₂₄N₂O₂

Average Mass

324.4168 Da

Monoisotopic Mass

324.18378 Da

IUPAC Name

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

Traditional Name

quinidine

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCN(C[C@@H]1C=C)[C@]([H])(C2)[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1

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-LHHVKLHASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	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
Aspidosperma marcgravianum	LOTUS Database	35616633
Aspidosperma marcgravianum L.	KNApSAcK Database	22123792
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 pubescens	KNApSAcK Database	22123792
Cinchona robusta	KNApSAcK Database	22123792
Cinchona sp.	KNApSAcK Database	22123792
Cinchona spp.	KNApSAcK Database	22123792
Cinchona succirubra	Plant	KNApSAcK
Diaporthe sp.	NPAtlas	21804259
Remijia pedunculata	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	284.00 to 285.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	620.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.560 (est)	The Good Scents Company Information System

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	35.64 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

BMRB

HMDB ID

HMDB0015044

DrugBank ID

DB00908

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031117

Chemspider ID

389880

KEGG Compound ID

C06527

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Quinidine

METLIN ID

Not Available

PubChem Compound

441074

PDB ID

Not Available

ChEBI ID

28593

Good Scents ID

rw1597461

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Pajeva IK, Wiese M: Pharmacophore model of drugs involved in P-glycoprotein multidrug resistance: explanation of structural variety (hypothesis). J Med Chem. 2002 Dec 19;45(26):5671-86. doi: 10.1021/jm020941h. [PubMed:12477351 ]
Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. doi: 10.1021/jm021012t. [PubMed:12699389 ]
Lombardo F, Obach RS, Shalaeva MY, Gao F: Prediction of human volume of distribution values for neutral and basic drugs. 2. Extended data set and leave-class-out statistics. J Med Chem. 2004 Feb 26;47(5):1242-50. doi: 10.1021/jm030408h. [PubMed:14971904 ]
Kharasch ED, Hoffer C, Altuntas TG, Whittington D: Quinidine as a probe for the role of p-glycoprotein in the intestinal absorption and clinical effects of fentanyl. J Clin Pharmacol. 2004 Mar;44(3):224-33. doi: 10.1177/0091270003262075. [PubMed:14973303 ]

Showing NP-Card for Quinidine (NP0002764)

MOL for NP0002764 (Quinidine)

3D MOL for NP0002764 (Quinidine)

3D SDF for NP0002764 (Quinidine)

3D-SDF for NP0002764 (Quinidine)

PDB for NP0002764 (Quinidine)

3D PDB for NP0002764 (Quinidine)

SMILES for NP0002764 (Quinidine)

INCHI for NP0002764 (Quinidine)

Structure for NP0002764 (Quinidine)

3D Structure for NP0002764 (Quinidine)