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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (6) Show 17 proteins XML

enzymes (11)transporters (6) Show 17 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014611

Secondary Accession Numbers

HMDB14611

Metabolite Identification

Common Name

Quinine

Description

Quinine is an alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood. [PubChem].

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014611
     RDKit          3D
Quinine
 48 51  0  0  0  0  0  0  0  0999 V2000
    6.3100   -0.7640   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928   -1.0903   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9233   -0.2050   -0.2338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9012   -0.7774   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348   -0.1299   -0.8658 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7564    1.2692   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5382    1.5436    0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.2082    1.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0670   -0.7360    1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0866   -0.8716    0.2669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3063   -0.4373    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7384   -1.1969    1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -0.6648   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -1.2941   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -1.5034   -2.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0248   -1.0487   -2.6215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888   -0.4263   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7002    0.0349   -1.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1323    0.6784   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2954    0.9010    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    1.5460    2.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0419    1.9915    2.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874    0.4387    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475   -0.2068   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1429   -1.4181   -0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4717    0.1782   -0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   -2.0363    0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3072    0.7279   -0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -0.6969   -2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380   -1.8688   -0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343    1.7541   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575    1.6869   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9057    1.8583    1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443    2.2606    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642    0.2819    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -1.6928    1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.3194    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -1.9377   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3786    0.6350    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238   -0.8726    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165   -1.6589   -1.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4139   -2.0165   -3.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643   -0.1342   -2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1505    1.0308   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7242    1.1649    1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2813    2.4059    3.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    2.7989    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    0.6098    1.5568 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  6
  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  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


  Mrv0541 04191212122D          

 25 28  0  0  0  0            999 V2000
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.0626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.8876    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5559    2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.3001    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.6501    0.0000 N   0  0  2  0  0  0  0  0  0  0  0  0
    2.5560    0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7144    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1435    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  3 23  1  0  0  0  0
  3  2  2  0  0  0  0
  1  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  5  1  0  0  0  0
  1  6  2  0  0  0  0
  7 10  2  0  0  0  0
  6  7  1  0  0  0  0
  8  5  1  0  0  0  0
 21  8  1  0  0  0  0
 10  9  1  0  0  0  0
  8  9  2  0  0  0  0
 20 21  1  0  0  0  0
 11 20  1  0  0  0  0
 20 17  1  0  0  0  0
 16 11  1  0  0  0  0
 12 13  1  0  0  0  0
 16 13  1  0  0  0  0
 13 15  1  1  0  0  0
 16 14  1  6  0  0  0
 14 18  1  0  0  0  0
 15 19  2  0  0  0  0
 17 18  1  6  0  0  0
 21 22  1  1  0  0  0
 20 24  1  1  0  0  0
 17 12  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014611

> <DATABASE_NAME>
hmdb

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

> <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_AVERAGE_POLARIZABILITY>
35.95718757326015

> <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>
9.045547511829293

> <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

$$$$

HMDB0014611
     RDKit          3D
Quinine
 48 51  0  0  0  0  0  0  0  0999 V2000
    6.3100   -0.7640   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928   -1.0903   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9233   -0.2050   -0.2338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9012   -0.7774   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348   -0.1299   -0.8658 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7564    1.2692   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5382    1.5436    0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.2082    1.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0670   -0.7360    1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0866   -0.8716    0.2669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3063   -0.4373    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7384   -1.1969    1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -0.6648   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -1.2941   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -1.5034   -2.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0248   -1.0487   -2.6215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888   -0.4263   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7002    0.0349   -1.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1323    0.6784   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2954    0.9010    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    1.5460    2.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0419    1.9915    2.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874    0.4387    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475   -0.2068   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1429   -1.4181   -0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4717    0.1782   -0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   -2.0363    0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3072    0.7279   -0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -0.6969   -2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380   -1.8688   -0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343    1.7541   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575    1.6869   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9057    1.8583    1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443    2.2606    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642    0.2819    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -1.6928    1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.3194    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -1.9377   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3786    0.6350    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238   -0.8726    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165   -1.6589   -1.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4139   -2.0165   -3.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643   -0.1342   -2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1505    1.0308   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7242    1.1649    1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2813    2.4059    3.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    2.7989    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    0.6098    1.5568 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  6
  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  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                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334  -1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.771   4.827   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   6.160   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.001   3.080   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.771   1.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001   1.540   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       2.667   2.310   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      -5.335   0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    3    1                                                       
CONECT    3    4   23    2                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7   10    6                                                       
CONECT    8    5   21    9                                                  
CONECT    9   10    8                                                       
CONECT   10    7    9                                                       
CONECT   11   20   16                                                       
CONECT   12   13   17                                                       
CONECT   13   12   16   15                                                  
CONECT   14   16   18                                                       
CONECT   15   13   19                                                       
CONECT   16   11   13   14                                                  
CONECT   17   20   18   12                                                  
CONECT   18   14   17                                                       
CONECT   19   15                                                            
CONECT   20   21   11   17   24                                             
CONECT   21    8   20   22                                                  
CONECT   22   21                                                            
CONECT   23    3   25                                                       
CONECT   24   20                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0014611
HETATM    1  C1  UNL     1       6.310  -0.764  -0.397  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.093  -1.090  -0.015  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.923  -0.205  -0.234  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.901  -0.777  -1.177  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.635  -0.130  -0.866  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.756   1.269  -0.583  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.538   1.544   0.706  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.227   0.208   1.032  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.067  -0.736   1.381  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.087  -0.872   0.267  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.306  -0.437   0.605  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.738  -1.197   1.690  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.230  -0.665  -0.531  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.899  -1.294  -1.704  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.759  -1.503  -2.761  1.00  0.00           C  
HETATM   16  N2  UNL     1      -3.025  -1.049  -2.621  1.00  0.00           N  
HETATM   17  C14 UNL     1      -3.389  -0.426  -1.486  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.700   0.035  -1.359  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.132   0.678  -0.220  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.295   0.901   0.853  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.700   1.546   2.016  1.00  0.00           O  
HETATM   22  C18 UNL     1      -6.042   1.992   2.086  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.987   0.439   0.721  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.548  -0.207  -0.417  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.143  -1.418  -0.230  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.472   0.178  -0.887  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.939  -2.036   0.476  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.307   0.728  -0.726  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.182  -0.697  -2.238  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.838  -1.869  -0.955  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.234   1.754  -1.458  1.00  0.00           H  
HETATM   32  H8  UNL     1       0.758   1.687  -0.472  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.906   1.858   1.532  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.344   2.261   0.449  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.864   0.282   1.910  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.557  -1.693   1.670  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.627  -0.319   2.318  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.056  -1.938  -0.028  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.379   0.635   0.868  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.324  -0.873   2.535  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.117  -1.659  -1.809  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.414  -2.017  -3.665  1.00  0.00           H  
HETATM   43  H19 UNL     1      -5.364  -0.134  -2.193  1.00  0.00           H  
HETATM   44  H20 UNL     1      -6.151   1.031  -0.138  1.00  0.00           H  
HETATM   45  H21 UNL     1      -6.724   1.165   1.801  1.00  0.00           H  
HETATM   46  H22 UNL     1      -6.281   2.406   3.099  1.00  0.00           H  
HETATM   47  H23 UNL     1      -6.165   2.799   1.306  1.00  0.00           H  
HETATM   48  H24 UNL     1      -2.328   0.610   1.557  1.00  0.00           H  
CONECT    1    2    2   25   26
CONECT    2    3   27
CONECT    3    4    8   28
CONECT    4    5   29   30
CONECT    5    6   10
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35
CONECT    9   10   36   37
CONECT   10   11   38
CONECT   11   12   13   39
CONECT   12   40
CONECT   13   14   14   24
CONECT   14   15   41
CONECT   15   16   16   42
CONECT   16   17
CONECT   17   18   18   24
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   23
CONECT   21   22
CONECT   22   45   46   47
CONECT   23   24   24   48
END

HMDB0014611
     RDKit          3D
Quinine
 48 51  0  0  0  0  0  0  0  0999 V2000
    6.3100   -0.7640   -0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0928   -1.0903   -0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9233   -0.2050   -0.2338 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9012   -0.7774   -1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348   -0.1299   -0.8658 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7564    1.2692   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5382    1.5436    0.7056 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    0.2082    1.0320 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0670   -0.7360    1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0866   -0.8716    0.2669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3063   -0.4373    0.6048 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7384   -1.1969    1.6904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -0.6648   -0.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8988   -1.2941   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -1.5034   -2.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0248   -1.0487   -2.6215 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888   -0.4263   -1.4856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7002    0.0349   -1.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1323    0.6784   -0.2202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2954    0.9010    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7005    1.5460    2.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0419    1.9915    2.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9874    0.4387    0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5475   -0.2068   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1429   -1.4181   -0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4717    0.1782   -0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   -2.0363    0.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3072    0.7279   -0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -0.6969   -2.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380   -1.8688   -0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2343    1.7541   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575    1.6869   -0.4715 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9057    1.8583    1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3443    2.2606    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8642    0.2819    1.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565   -1.6928    1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.3194    2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -1.9377   -0.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3786    0.6350    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3238   -0.8726    2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165   -1.6589   -1.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4139   -2.0165   -3.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643   -0.1342   -2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1505    1.0308   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7242    1.1649    1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2813    2.4059    3.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1651    2.7989    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277    0.6098    1.5568 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  6
  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  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 Stereo Labels

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	MeSH
Surquina	MeSH
Biquinate	MeSH
Quinimax	MeSH
Quinine bisulfate	MeSH
Quinine sulfate	MeSH
Quinoctal	MeSH
Quinson	MeSH
Quinsul	MeSH
Bisulfate, quinine	MeSH
Hydrochloride, quinine	MeSH
Legatrim	MeSH
Quinamm	MeSH
Quinbisan	MeSH
Quinbisul	MeSH
Quinine lafran	MeSH
Quinine sulphate	MeSH
Quinine-odan	MeSH
Sulfate, quinine	MeSH
Sulphate, quinine	MeSH
Quindan	MeSH
Quinine hydrochloride	MeSH
Strema	MeSH
6'-Methoxycinchonine	HMDB
Quinine, anhydrous	HMDB
Quinineanhydrous	HMDB
Quinoline alkaloid	HMDB
Aventis brand OF quinine bisulfate	MeSH, HMDB
Fawns and mcallan brand OF quinine sulfate	MeSH, HMDB
Foy brand OF quinine sulfate	MeSH, HMDB
Plough brand OF quinine sulfate	MeSH, HMDB
Fawns and mcallan brand OF quinine bisulfate	MeSH, HMDB
Hoechst brand OF quinine sulfate	MeSH, HMDB
Lafran brand OF quinine hydrochloride	MeSH, HMDB
Alphapharm brand OF quinine sulfate	MeSH, HMDB
Innotech brand OF quinine hydrochloride	MeSH, HMDB
Odan brand OF quinine sulfate	MeSH, HMDB
Prosana brand OF quinine bisulfate	MeSH, HMDB

Chemical Formula

C₂₀H₂₄N₂O₂

Average Molecular Weight

324.4168

Monoisotopic Molecular Weight

324.183778022

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

130-95-0

SMILES

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

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

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

Substituents

Cinchonan-skeleton
4-quinolinemethanol
Quinoline
Anisole
Quinuclidine
Alkyl aryl ether
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Alcohol
Organic oxygen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cinchona alkaloid (CHEBI:15854 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Hypotension (HMDB: HMDB0014611)

Organoleptic effect

Odor

bitter

Disposition

Biological location

Cell membrane (HMDB: HMDB0014611)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014611)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0014611)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	57 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.33 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	177.4	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
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	35.96 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.022	31661259
DarkChem	[M-H]-	174.868	31661259
DeepCCS	[M-2H]-	208.005	30932474
DeepCCS	[M+Na]+	182.709	30932474
AllCCS	[M+H]+	181.1	32859911
AllCCS	[M+H-H2O]+	177.9	32859911
AllCCS	[M+NH4]+	184.1	32859911
AllCCS	[M+Na]+	185.0	32859911
AllCCS	[M-H]-	186.3	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	186.5	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quinine,1TMS,isomer #1	C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O[Si](C)(C)C)C1=CC=NC2=CC=C(OC)C=C12	2630.1	Semi standard non polar	33892256
Quinine,1TBDMS,isomer #1	C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(OC)C=C12	2880.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Quinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-1901000000-8176add5a84f7ae1eb69	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinine GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-7947000000-ee233460f7e7fbb00ca7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 60V, Positive-QTOF	splash10-00ai-7930000000-eb63f68d11153566b027	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 75V, Positive-QTOF	splash10-00c0-7910000000-c0d16dda8d8a74dd1657	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 45V, Positive-QTOF	splash10-0059-5945000000-dff1a74853685996f965	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 15V, Positive-QTOF	splash10-004i-0009000000-4cf6c66b2059468cd1e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 30V, Positive-QTOF	splash10-004i-0009000000-d4367d77a81731ba3654	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 60V, Positive-QTOF	splash10-00ai-7930000000-94e16a407d113a547240	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 45V, Positive-QTOF	splash10-0059-5945000000-ddc4f19918fbae8ffe0c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 90V, Positive-QTOF	splash10-0fc0-6900000000-8bb456f41e7cb82dfcf9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 90V, Positive-QTOF	splash10-0fc0-6900000000-f458cccf839df1d5239b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinine 75V, Positive-QTOF	splash10-00c0-7910000000-4b620f5ca762298602e7	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 10V, Positive-QTOF	splash10-0a6r-0019000000-0f42379f2989cf204f72	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 20V, Positive-QTOF	splash10-0a4r-0729000000-5a0d8aa890e6c737bf45	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 40V, Positive-QTOF	splash10-0079-0920000000-70e4fed1a61c38cf53fb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 10V, Negative-QTOF	splash10-00di-0109000000-e84ce15e838ff8ac33f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 20V, Negative-QTOF	splash10-05fr-0229000000-b87ca7a53d952af7505e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 40V, Negative-QTOF	splash10-0540-0920000000-12d8977ce43e168f8453	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 10V, Positive-QTOF	splash10-004i-0009000000-2125f5c1412244f91fb3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 20V, Positive-QTOF	splash10-004i-0109000000-1096d980c779fca1eb3f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 40V, Positive-QTOF	splash10-00dr-0920000000-468db2e8e8941541468c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 10V, Negative-QTOF	splash10-00di-0019000000-9c5f7ffbd0d69038e6da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 20V, Negative-QTOF	splash10-0abi-0914000000-92707d10764c62ebe320	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinine 40V, Negative-QTOF	splash10-0a4i-0900000000-9e1ce60a980eb9551f33	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00468	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00468	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00468

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:8143397 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Reactions

Quinine + NADPH + Oxygen → 3-Hydroxyquinine + NADP + Water	details

References

Zhao XJ, Yokoyama H, Chiba K, Wanwimolruk S, Ishizaki T: Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human live microsomes and nine recombinant human cytochromes P450. J Pharmacol Exp Ther. 1996 Dec;279(3):1327-34. [PubMed:8968357 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhao XJ, Yokoyama H, Chiba K, Wanwimolruk S, Ishizaki T: Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human live microsomes and nine recombinant human cytochromes P450. J Pharmacol Exp Ther. 1996 Dec;279(3):1327-34. [PubMed:8968357 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

5. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

Enzyme Details

7. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 3A7

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A7
Uniprot ID:: P24462
Molecular weight:: 57525.03

Enzyme Details

9. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
van der Sandt IC, Blom-Roosemalen MC, de Boer AG, Breimer DD: Specificity of doxorubicin versus rhodamine-123 in assessing P-glycoprotein functionality in the LLC-PK1, LLC-PK1:MDR1 and Caco-2 cell lines. Eur J Pharm Sci. 2000 Sep;11(3):207-14. [PubMed:11042226 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. [PubMed:8621716 ]

Enzyme Details

3. Solute carrier family 22 member 4

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)
Gene Name:: SLC22A4
Uniprot ID:: Q9H015
Molecular weight:: 62154.5

References

Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651 ]

Enzyme Details

4. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257 ]
Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]
Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
Sweet DH, Miller DS, Pritchard JB: Ventricular choline transport: a role for organic cation transporter 2 expressed in choroid plexus. J Biol Chem. 2001 Nov 9;276(45):41611-9. Epub 2001 Sep 11. [PubMed:11553644 ]
Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515 ]
Grundemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H: Drug excretion mediated by a new prototype of polyspecific transporter. Nature. 1994 Dec 8;372(6506):549-52. [PubMed:7990927 ]
Martel F, Vetter T, Russ H, Grundemann D, Azevedo I, Koepsell H, Schomig E: Transport of small organic cations in the rat liver. The role of the organic cation transporter OCT1. Naunyn Schmiedebergs Arch Pharmacol. 1996 Aug-Sep;354(3):320-6. [PubMed:8878062 ]
Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [PubMed:8898084 ]
Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J Biol Chem. 1996 Dec 20;271(51):32599-604. [PubMed:8955087 ]

Enzyme Details

5. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641 ]

Enzyme Details

6. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Sweet DH, Miller DS, Pritchard JB: Ventricular choline transport: a role for organic cation transporter 2 expressed in choroid plexus. J Biol Chem. 2001 Nov 9;276(45):41611-9. Epub 2001 Sep 11. [PubMed:11553644 ]
Gorboulev V, Ulzheimer JC, Akhoundova A, Ulzheimer-Teuber I, Karbach U, Quester S, Baumann C, Lang F, Busch AE, Koepsell H: Cloning and characterization of two human polyspecific organic cation transporters. DNA Cell Biol. 1997 Jul;16(7):871-81. [PubMed:9260930 ]
Kakehi M, Koyabu N, Nakamura T, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Functional characterization of mouse cation transporter mOCT2 compared with mOCT1. Biochem Biophys Res Commun. 2002 Aug 23;296(3):644-50. [PubMed:12176030 ]
Arndt P, Volk C, Gorboulev V, Budiman T, Popp C, Ulzheimer-Teuber I, Akhoundova A, Koppatz S, Bamberg E, Nagel G, Koepsell H: Interaction of cations, anions, and weak base quinine with rat renal cation transporter rOCT2 compared with rOCT1. Am J Physiol Renal Physiol. 2001 Sep;281(3):F454-68. [PubMed:11502595 ]
Goralski KB, Lou G, Prowse MT, Gorboulev V, Volk C, Koepsell H, Sitar DS: The cation transporters rOCT1 and rOCT2 interact with bicarbonate but play only a minor role for amantadine uptake into rat renal proximal tubules. J Pharmacol Exp Ther. 2002 Dec;303(3):959-68. [PubMed:12438515 ]
Sweet DH, Pritchard JB: rOCT2 is a basolateral potential-driven carrier, not an organic cation/proton exchanger. Am J Physiol. 1999 Dec;277(6 Pt 2):F890-8. [PubMed:10600936 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Showing metabocard for Quinine (HMDB0014611)

MOL for HMDB0014611 (Quinine)

3D MOL for HMDB0014611 (Quinine)

3D SDF for HMDB0014611 (Quinine)

3D-SDF for HMDB0014611 (Quinine)

PDB for HMDB0014611 (Quinine)

3D PDB for HMDB0014611 (Quinine)

SMILES for HMDB0014611 (Quinine)

INCHI for HMDB0014611 (Quinine)

Structure for HMDB0014611 (Quinine)

3D Structure for HMDB0014611 (Quinine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

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Transporters

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