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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (12)transporters (9) Show 21 proteins XML

enzymes (12)transporters (9) Show 21 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015044

Secondary Accession Numbers

HMDB15044

Metabolite Identification

Common Name

Quinidine

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. A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy. Quinidine is a drug which is used for the treatment of ventricular pre-excitation and cardiac dysrhythmias. Quinidine is a very strong basic compound (based on its pKa). In humans, quinidine is involved in quinidine action pathway.

Structure

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

908
  Mrv0541 02231215052D          

 26 29  0  0  1  0            999 V2000
    6.8986    0.0158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0964    1.2335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -1.6060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    2.9033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592   -1.3925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4696    0.0158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6727    0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302   -2.2175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3523   -2.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427   -2.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0668   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    0.4283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2334   -2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    1.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8986    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8986    2.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6360    1.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    2.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6360    2.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3836    1.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3836    2.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8125    1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216   -1.2217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0184   -0.3508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  6  0  0  0
  2 22  1  0  0  0  0
  2 24  1  0  0  0  0
  3  6  1  0  0  0  0
  3 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 18  2  0  0  0  0
  4 20  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 25  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 26  1  1  0  0  0
  8 10  1  0  0  0  0
  8 13  1  6  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END

HMDB0015044
     RDKit          3D
Quinidine
 48 51  0  0  0  0  0  0  0  0999 V2000
    4.7609   -2.6821   -0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -2.0785    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121   -0.6106   -0.1294 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3376   -0.2397   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311    1.0333   -0.5079 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399    1.9394   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7051    1.5446    0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3666    0.0790    1.2328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8932    0.0593    1.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927    0.9253    0.7061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2698    0.2517    0.5216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8152    0.2442    1.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    1.0813   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    2.3109   -0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    2.9996   -1.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    2.5352   -1.8129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    1.3366   -1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    0.8155   -1.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9733   -0.4143   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007   -1.1686   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120   -2.4019    0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6988   -2.9320   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559   -0.6557   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576    0.5734   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5332   -2.1166   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -3.7412   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123   -2.6531    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4236   -0.1766   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889   -0.1388   -2.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608   -1.0219   -0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    2.9632   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5847    1.9078   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3913    2.1755    1.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985    1.5977    0.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -0.3796    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8617    0.5449    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054   -0.9509    1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062    1.9224    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1671   -0.7860    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615   -0.5190    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1608    2.7026   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    3.9651   -1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915    1.3997   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9558   -0.8237   -1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7068   -4.0061    0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403   -2.8580   -1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4150   -2.3566    0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078   -1.1967    0.5333 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  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

908
  Mrv0541 02231215052D          

 26 29  0  0  1  0            999 V2000
    6.8986    0.0158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0964    1.2335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -1.6060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    2.9033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592   -1.3925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4696    0.0158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6727    0.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0302   -2.2175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3523   -2.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4427   -2.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0668   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    0.4283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2334   -2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    1.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8986    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    1.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8986    2.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6360    1.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4696    2.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6360    2.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3836    1.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3836    2.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8125    1.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8216   -1.2217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0184   -0.3508    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  6  0  0  0
  2 22  1  0  0  0  0
  2 24  1  0  0  0  0
  3  6  1  0  0  0  0
  3 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 18  2  0  0  0  0
  4 20  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 25  1  1  0  0  0
  6  7  1  0  0  0  0
  6 12  1  0  0  0  0
  6 26  1  1  0  0  0
  8 10  1  0  0  0  0
  8 13  1  6  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015044

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.4168

> <EXACT_MASS>
324.183778022

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.82062136932111

> <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>
9.045547511829293

> <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>
quinidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015044
     RDKit          3D
Quinidine
 48 51  0  0  0  0  0  0  0  0999 V2000
    4.7609   -2.6821   -0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -2.0785    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121   -0.6106   -0.1294 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3376   -0.2397   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311    1.0333   -0.5079 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399    1.9394   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7051    1.5446    0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3666    0.0790    1.2328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8932    0.0593    1.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927    0.9253    0.7061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2698    0.2517    0.5216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8152    0.2442    1.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    1.0813   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    2.3109   -0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    2.9996   -1.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    2.5352   -1.8129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    1.3366   -1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    0.8155   -1.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9733   -0.4143   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007   -1.1686   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120   -2.4019    0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6988   -2.9320   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559   -0.6557   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576    0.5734   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5332   -2.1166   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -3.7412   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123   -2.6531    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4236   -0.1766   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889   -0.1388   -2.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608   -1.0219   -0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    2.9632   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5847    1.9078   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3913    2.1755    1.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985    1.5977    0.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -0.3796    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8617    0.5449    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054   -0.9509    1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062    1.9224    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1671   -0.7860    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615   -0.5190    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1608    2.7026   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    3.9651   -1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915    1.3997   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9558   -0.8237   -1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7068   -4.0061    0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403   -2.8580   -1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4150   -2.3566    0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078   -1.1967    0.5333 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  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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 908                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.877   0.029   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      16.980   2.303   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.811  -2.998   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      11.544   5.419   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.324  -2.599   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.210   0.029   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.722   0.428   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.656  -4.139   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.991  -5.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.426  -5.473   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.325  -4.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.544   0.799   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.169  -3.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.544   2.339   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -4.830   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.877   3.109   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.210   3.109   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.877   4.649   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.254   2.286   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.210   4.649   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.254   5.473   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.649   3.078   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.649   4.682   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.317   3.067   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       7.134  -2.281   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      11.234  -0.655   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   22   24                                                       
CONECT    3    6   10   11                                                  
CONECT    4   18   20                                                       
CONECT    5    7    8    9   25                                             
CONECT    6    3    7   12   26                                             
CONECT    7    5    6                                                       
CONECT    8    5   10   13                                                  
CONECT    9    5   11                                                       
CONECT   10    3    8                                                       
CONECT   11    3    9                                                       
CONECT   12    1    6   14                                                  
CONECT   13    8   15                                                       
CONECT   14   12   16   17                                                  
CONECT   15   13                                                            
CONECT   16   14   18   19                                                  
CONECT   17   14   20                                                       
CONECT   18    4   16   21                                                  
CONECT   19   16   22                                                       
CONECT   20    4   17                                                       
CONECT   21   18   23                                                       
CONECT   22    2   19   23                                                  
CONECT   23   21   22                                                       
CONECT   24    2                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0015044
HETATM    1  C1  UNL     1       4.761  -2.682  -0.402  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.679  -2.079   0.039  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.512  -0.611  -0.129  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.338  -0.240  -0.977  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.831   1.033  -0.508  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.940   1.939  -0.281  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.705   1.545   0.988  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.367   0.079   1.233  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.893   0.059   1.660  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.093   0.925   0.706  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.270   0.252   0.522  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.815   0.244   1.822  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.176   1.081  -0.295  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.821   2.311  -0.802  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.743   3.000  -1.551  1.00  0.00           C  
HETATM   16  N2  UNL     1      -2.970   2.535  -1.813  1.00  0.00           N  
HETATM   17  C14 UNL     1      -3.342   1.337  -1.329  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.605   0.815  -1.575  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.973  -0.414  -1.072  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.101  -1.169  -0.309  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.412  -2.402   0.219  1.00  0.00           O  
HETATM   22  C18 UNL     1      -5.699  -2.932  -0.031  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.856  -0.656  -0.066  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.458   0.573  -0.556  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.533  -2.117  -0.889  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.880  -3.741  -0.280  1.00  0.00           H  
HETATM   27  H3  UNL     1       2.912  -2.653   0.525  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.424  -0.177  -0.591  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.589  -0.139  -2.039  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.561  -1.022  -0.855  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.526   2.963  -0.152  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.585   1.908  -1.168  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.391   2.175   1.842  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.799   1.598   0.800  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.988  -0.380   2.001  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.862   0.545   2.655  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.505  -0.951   1.767  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.906   1.922   1.124  1.00  0.00           H  
HETATM   39  H15 UNL     1      -0.167  -0.786   0.208  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.461  -0.519   2.345  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.161   2.703  -0.602  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.455   3.965  -1.946  1.00  0.00           H  
HETATM   43  H19 UNL     1      -5.291   1.400  -2.171  1.00  0.00           H  
HETATM   44  H20 UNL     1      -5.956  -0.824  -1.261  1.00  0.00           H  
HETATM   45  H21 UNL     1      -5.707  -4.006   0.269  1.00  0.00           H  
HETATM   46  H22 UNL     1      -5.940  -2.858  -1.111  1.00  0.00           H  
HETATM   47  H23 UNL     1      -6.415  -2.357   0.592  1.00  0.00           H  
HETATM   48  H24 UNL     1      -2.108  -1.197   0.533  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

HMDB0015044
     RDKit          3D
Quinidine
 48 51  0  0  0  0  0  0  0  0999 V2000
    4.7609   -2.6821   -0.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -2.0785    0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121   -0.6106   -0.1294 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3376   -0.2397   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311    1.0333   -0.5079 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399    1.9394   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7051    1.5446    0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3666    0.0790    1.2328 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8932    0.0593    1.6604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927    0.9253    0.7061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2698    0.2517    0.5216 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8152    0.2442    1.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    1.0813   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209    2.3109   -0.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7435    2.9996   -1.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    2.5352   -1.8129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415    1.3366   -1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    0.8155   -1.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9733   -0.4143   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007   -1.1686   -0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120   -2.4019    0.2195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6988   -2.9320   -0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559   -0.6557   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576    0.5734   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5332   -2.1166   -0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8802   -3.7412   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123   -2.6531    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4236   -0.1766   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889   -0.1388   -2.0386 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5608   -1.0219   -0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    2.9632   -0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5847    1.9078   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3913    2.1755    1.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7985    1.5977    0.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9877   -0.3796    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8617    0.5449    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054   -0.9509    1.7675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062    1.9224    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1671   -0.7860    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615   -0.5190    2.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1608    2.7026   -0.6018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4548    3.9651   -1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915    1.3997   -2.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9558   -0.8237   -1.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7068   -4.0061    0.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9403   -2.8580   -1.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4150   -2.3566    0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1078   -1.1967    0.5333 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  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 Stereo Labels

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 Molecular Weight

324.4168

Monoisotopic Molecular Weight

324.183778022

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

56-54-2

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

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:28593 )

Ontology

Not Available

Urine (PMID: 21059682)
Feces (PMID: 25037050)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015044)
Membrane (HMDB: HMDB0015044)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Quinidine Action Pathway (PathBank: SMP0000323)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 °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	175.8	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	35.82 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]+	177.783	31661259
DarkChem	[M-H]-	175.048	31661259
DeepCCS	[M-2H]-	212.732	30932474
DeepCCS	[M+Na]+	188.145	30932474
AllCCS	[M+H]+	181.2	32859911
AllCCS	[M+H-H2O]+	178.0	32859911
AllCCS	[M+NH4]+	184.2	32859911
AllCCS	[M+Na]+	185.1	32859911
AllCCS	[M-H]-	186.3	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	186.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quinidine	[H][C@@]12CCN(C[C@@H]1C=C)[C@]([H])(C2)[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1	3358.5	Standard polar	33892256
Quinidine	[H][C@@]12CCN(C[C@@H]1C=C)[C@]([H])(C2)[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1	2735.5	Standard non polar	33892256
Quinidine	[H][C@@]12CCN(C[C@@H]1C=C)[C@]([H])(C2)[C@@H](O)C1=C2C=C(OC)C=CC2=NC=C1	2874.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quinidine,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
Quinidine,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 - Quinidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-1901000000-90466d795da1be8cafae	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinidine GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-7947000000-ee233460f7e7fbb00ca7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinidine 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 - Quinidine LC-ESI-qTof , Positive-QTOF	splash10-02ta-3900000000-46a157d2899290cbf4ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine LC-ESI-qTof , Positive-QTOF	splash10-0200-2952000000-2777ab3374ec2b052b2e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , negative-QTOF	splash10-0bt9-0908000000-f7ff24907014d8850472	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , negative-QTOF	splash10-08fr-0907000000-f6d31042d549da6bcfd0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , negative-QTOF	splash10-0bt9-0709000000-2c0e665e2c3031c8e517	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , negative-QTOF	splash10-00di-0009133000-a893d9e0e441c597fac3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , negative-QTOF	splash10-00di-0009001000-0a0220fd8eeb9e62bc20	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , positive-QTOF	splash10-0a4i-0469000000-3679f13f09481b3563c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , positive-QTOF	splash10-0a4i-0459000000-60c4a39356a4afeef2d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine Linear Ion Trap , positive-QTOF	splash10-0a4i-0239000000-644b48bb63dd87dac231	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine , positive-QTOF	splash10-03di-0910000000-b0045fccdbe90e598912	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine , positive-QTOF	splash10-004i-0229000000-f88b510f13aab6a2bb44	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine , positive-QTOF	splash10-02ta-3900000000-46a157d2899290cbf4ab	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine , positive-QTOF	splash10-0200-2952000000-2777ab3374ec2b052b2e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine 40V, Positive-QTOF	splash10-00ai-6930000000-44317fd6318c96581c84	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine 10V, Positive-QTOF	splash10-004i-0009000000-fe19371b962ad0614431	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinidine 20V, Positive-QTOF	splash10-004i-0109000000-887063f0b5addd8d47c0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 10V, Positive-QTOF	splash10-0a6r-0019000000-0f42379f2989cf204f72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 20V, Positive-QTOF	splash10-0a4r-0729000000-5a0d8aa890e6c737bf45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 40V, Positive-QTOF	splash10-0079-0920000000-70e4fed1a61c38cf53fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 10V, Negative-QTOF	splash10-00di-0109000000-e84ce15e838ff8ac33f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 20V, Negative-QTOF	splash10-05fr-0229000000-b87ca7a53d952af7505e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 40V, Negative-QTOF	splash10-0540-0920000000-12d8977ce43e168f8453	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 10V, Positive-QTOF	splash10-004i-0009000000-2125f5c1412244f91fb3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinidine 20V, Positive-QTOF	splash10-004i-0209000000-138a21908ae52680c7c5	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Quinidine Action Pathway		Not Available

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 DB00908	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00908	21059682	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB00908

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

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

Food Biomarker Ontology

Not Available

VMH ID

M02821

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 21 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

References

Ludwig E, Schmid J, Beschke K, Ebner T: Activation of human cytochrome P-450 3A4-catalyzed meloxicam 5'-methylhydroxylation by quinidine and hydroquinidine in vitro. J Pharmacol Exp Ther. 1999 Jul;290(1):1-8. [PubMed:10381752 ]
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

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 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

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 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

5. Cytochrome P450 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

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 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

7. 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

8. 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

9. 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 ]

Enzyme Details

10. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Po SS, Wang DW, Yang IC, Johnson JP Jr, Nie L, Bennett PB: Modulation of HERG potassium channels by extracellular magnesium and quinidine. J Cardiovasc Pharmacol. 1999 Feb;33(2):181-5. [PubMed:10028924 ]
Dong DL, Li Z, Wang HZ, Du ZM, Song WH, Yang BF: Acidification alters antiarrhythmic drug blockade of the ether-a-go-go-related Gene (HERG) Channels. Basic Clin Pharmacol Toxicol. 2004 May;94(5):209-12. [PubMed:15125690 ]
Wolpert C, Schimpf R, Giustetto C, Antzelevitch C, Cordeiro J, Dumaine R, Brugada R, Hong K, Bauersfeld U, Gaita F, Borggrefe M: Further insights into the effect of quinidine in short QT syndrome caused by a mutation in HERG. J Cardiovasc Electrophysiol. 2005 Jan;16(1):54-8. [PubMed:15673388 ]
Lin C, Ke X, Cvetanovic I, Ranade V, Somberg J: The influence of extracellular acidosis on the effect of IKr blockers. J Cardiovasc Pharmacol Ther. 2005 Mar;10(1):67-76. [PubMed:15821840 ]
Lin C, Cvetanovic I, Ke X, Ranade V, Somberg J: A mechanism for the potential proarrhythmic effect of acidosis, bradycardia, and hypokalemia on the blockade of human ether-a-go-go-related gene (HERG) channels. Am J Ther. 2005 Jul-Aug;12(4):328-36. [PubMed:16041196 ]
Guerard NC, Traebert M, Suter W, Dumotier BM: Selective block of IKs plays a significant role in MAP triangulation induced by IKr block in isolated rabbit heart. J Pharmacol Toxicol Methods. 2008 Jul-Aug;58(1):32-40. doi: 10.1016/j.vascn.2008.05.129. Epub 2008 Jun 8. [PubMed:18582585 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Nozawa T, Tamai I, Sai Y, Nezu J, Tsuji A: Contribution of organic anion transporting polypeptide OATP-C to hepatic elimination of the opioid pentapeptide analogue [D-Ala2, D-Leu5]-enkephalin. J Pharm Pharmacol. 2003 Jul;55(7):1013-20. [PubMed:12906759 ]

Enzyme Details

2. 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 ]
Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873 ]

Enzyme Details

3. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):773-9. [PubMed:12134946 ]

Enzyme Details

4. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]

Enzyme Details

5. 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

Choo EF, Leake B, Wandel C, Imamura H, Wood AJ, Wilkinson GR, Kim RB: Pharmacological inhibition of P-glycoprotein transport enhances the distribution of HIV-1 protease inhibitors into brain and testes. Drug Metab Dispos. 2000 Jun;28(6):655-60. [PubMed:10820137 ]
Gao J, Murase O, Schowen RL, Aube J, Borchardt RT: A functional assay for quantitation of the apparent affinities of ligands of P-glycoprotein in Caco-2 cells. Pharm Res. 2001 Feb;18(2):171-6. [PubMed:11405287 ]
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 ]
Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):765-72. [PubMed:12134945 ]
Horie K, Tang F, Borchardt RT: Isolation and characterization of Caco-2 subclones expressing high levels of multidrug resistance protein efflux transporter. Pharm Res. 2003 Feb;20(2):161-8. [PubMed:12636153 ]
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. [PubMed:12699389 ]
Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [PubMed:12649369 ]
Tanigawara Y, Okamura N, Hirai M, Yasuhara M, Ueda K, Kioka N, Komano T, Hori R: Transport of digoxin by human P-glycoprotein expressed in a porcine kidney epithelial cell line (LLC-PK1). J Pharmacol Exp Ther. 1992 Nov;263(2):840-5. [PubMed:1359120 ]
Ito T, Yano I, Tanaka K, Inui KI: Transport of quinolone antibacterial drugs by human P-glycoprotein expressed in a kidney epithelial cell line, LLC-PK1. J Pharmacol Exp Ther. 1997 Aug;282(2):955-60. [PubMed:9262363 ]
Kim RB, Fromm MF, Wandel C, Leake B, Wood AJ, Roden DM, Wilkinson GR: The drug transporter P-glycoprotein limits oral absorption and brain entry of HIV-1 protease inhibitors. J Clin Invest. 1998 Jan 15;101(2):289-94. [PubMed:9435299 ]
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 ]
Jutabha P, Wempe MF, Anzai N, Otomo J, Kadota T, Endou H: Xenopus laevis oocytes expressing human P-glycoprotein: probing trans- and cis-inhibitory effects on [3H]vinblastine and [3H]digoxin efflux. Pharmacol Res. 2010 Jan;61(1):76-84. doi: 10.1016/j.phrs.2009.07.002. Epub 2009 Jul 21. [PubMed:19631272 ]
Dahan A, Amidon GL: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009. Epub 2009 Jun 18. [PubMed:19541926 ]
Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. doi: 10.1208/s12248-009-9092-5. Epub 2009 Mar 25. [PubMed:19319690 ]
Smith BJ, Doran AC, McLean S, Tingley FD 3rd, O'Neill BT, Kajiji SM: P-glycoprotein efflux at the blood-brain barrier mediates differences in brain disposition and pharmacodynamics between two structurally related neurokinin-1 receptor antagonists. J Pharmacol Exp Ther. 2001 Sep;298(3):1252-9. [PubMed:11504828 ]
Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [PubMed:11785684 ]
Neuhoff S, Ungell AL, Zamora I, Artursson P: pH-dependent bidirectional transport of weakly basic drugs across Caco-2 monolayers: implications for drug-drug interactions. Pharm Res. 2003 Aug;20(8):1141-8. [PubMed:12948010 ]
Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [PubMed:12954186 ]
Fromm MF, Kim RB, Stein CM, Wilkinson GR, Roden DM: Inhibition of P-glycoprotein-mediated drug transport: A unifying mechanism to explain the interaction between digoxin and quinidine [seecomments]. Circulation. 1999 Feb 2;99(4):552-7. [PubMed:9927403 ]

Enzyme Details

6. 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

7. 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

van Montfoort JE, Muller M, Groothuis GM, Meijer DK, Koepsell H, Meier PJ: Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5. [PubMed:11408531 ]
Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755 ]
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 ]
Zhang L, Gorset W, Dresser MJ, Giacomini KM: The interaction of n-tetraalkylammonium compounds with a human organic cation transporter, hOCT1. J Pharmacol Exp Ther. 1999 Mar;288(3):1192-8. [PubMed:10027858 ]
Sandhu P, Lee W, Xu X, Leake BF, Yamazaki M, Stone JA, Lin JH, Pearson PG, Kim RB: Hepatic uptake of the novel antifungal agent caspofungin. Drug Metab Dispos. 2005 May;33(5):676-82. Epub 2005 Feb 16. [PubMed:15716364 ]
Sinclair CJ, Chi KD, Subramanian V, Ward KL, Green RM: Functional expression of a high affinity mammalian hepatic choline/organic cation transporter. J Lipid Res. 2000 Nov;41(11):1841-8. [PubMed:11060354 ]
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 ]
Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [PubMed:9808712 ]
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

8. 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

van Montfoort JE, Muller M, Groothuis GM, Meijer DK, Koepsell H, Meier PJ: Comparison of "type I" and "type II" organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5. [PubMed:11408531 ]
Cvetkovic M, Leake B, Fromm MF, Wilkinson GR, Kim RB: OATP and P-glycoprotein transporters mediate the cellular uptake and excretion of fexofenadine. Drug Metab Dispos. 1999 Aug;27(8):866-71. [PubMed:10421612 ]
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

9. 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

Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365 ]
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 ]
Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [PubMed:9808712 ]

Only showing the first 10 proteins. There are 21 proteins in total.

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Showing metabocard for Quinidine (HMDB0015044)

MOL for HMDB0015044 (Quinidine)

3D MOL for HMDB0015044 (Quinidine)

3D SDF for HMDB0015044 (Quinidine)

3D-SDF for HMDB0015044 (Quinidine)

PDB for HMDB0015044 (Quinidine)

3D PDB for HMDB0015044 (Quinidine)

SMILES for HMDB0015044 (Quinidine)

INCHI for HMDB0015044 (Quinidine)

Structure for HMDB0015044 (Quinidine)

3D Structure for HMDB0015044 (Quinidine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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