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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:05:23 UTC

Update Date

2021-09-26 22:56:32 UTC

HMDB ID

HMDB0247073

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Desmethylquinidine

Description

4-({5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(hydroxy)methyl)quinolin-6-ol 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. Based on a literature review very few articles have been published on 4-({5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(hydroxy)methyl)quinolin-6-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). O-desmethylquinidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically O-Desmethylquinidine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0247073
     RDKit          3D
O-Desmethylquinidine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.3677    0.5225    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705   -0.5008    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081   -0.5071    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017    0.7913    0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    0.9747   -0.3118 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    1.2613   -1.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071    0.0830   -1.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6988   -1.0650   -0.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2661   -1.4188   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003   -0.1335   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6719   -0.4959    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -0.6896    1.6341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7046    0.5198    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354    1.7443    1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    2.5440    1.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8844    2.1320    1.2363 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1203    0.9285    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    0.5554    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6398   -0.6427   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6177   -1.4315   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -2.6490   -1.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3184   -1.0084   -0.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575    0.1557    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4527    0.4121    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    1.5161    0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678   -1.5002    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368   -1.2955    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566    0.9654    1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032    1.6146    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    1.4038   -2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    2.1564   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -0.2931   -2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702    0.3480   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -1.8587   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -2.1647   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -1.8362   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.1070   -1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769   -1.5166    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996   -0.4294    2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    2.0908    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500    3.4953    1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746    1.1649    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6580   -0.9568   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -3.4716   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -1.6214   -0.6848 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
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 13 14  2  0
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 23 13  1  0
 10  5  1  0
 23 17  1  0
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 14 40  1  0
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 18 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
M  END


  Mrv1533004171503422D          

 23 26  0  0  0  0            999 V2000
    2.2396   -1.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540   -1.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -0.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205   -0.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205   -0.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830   -1.4834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975   -1.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0975   -0.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8119    0.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5264   -0.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9540   -2.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6685   -3.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2396   -3.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -3.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8106   -2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -2.3084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -2.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396   -2.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
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  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
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  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
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 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 13 23  2  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247073

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C1CC2CCN1CC2C=C)C1=C2C=C(O)C=CC2=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O2/c1-2-12-11-21-8-6-13(12)9-18(21)19(23)15-5-7-20-17-4-3-14(22)10-16(15)17/h2-5,7,10,12-13,18-19,22-23H,1,6,8-9,11H2

> <INCHI_KEY>
VJFMSYZSFUWQPZ-UHFFFAOYSA-N

> <FORMULA>
C19H22N2O2

> <MOLECULAR_WEIGHT>
310.397

> <EXACT_MASS>
310.168127956

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.02149493325931

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-({5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(hydroxy)methyl)quinolin-6-ol

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
1.9580330250756812

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.950910919880602

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.756924464821479

> <JCHEM_PKA_STRONGEST_BASIC>
8.954043083117359

> <JCHEM_POLAR_SURFACE_AREA>
56.59

> <JCHEM_REFRACTIVITY>
90.21130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cupreine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247073
     RDKit          3D
O-Desmethylquinidine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.3677    0.5225    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705   -0.5008    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081   -0.5071    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017    0.7913    0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    0.9747   -0.3118 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    1.2613   -1.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071    0.0830   -1.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6988   -1.0650   -0.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2661   -1.4188   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003   -0.1335   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6719   -0.4959    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -0.6896    1.6341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7046    0.5198    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354    1.7443    1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    2.5440    1.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8844    2.1320    1.2363 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1203    0.9285    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    0.5554    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6398   -0.6427   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6177   -1.4315   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -2.6490   -1.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3184   -1.0084   -0.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575    0.1557    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4527    0.4121    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    1.5161    0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678   -1.5002    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368   -1.2955    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566    0.9654    1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032    1.6146    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    1.4038   -2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    2.1564   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -0.2931   -2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702    0.3480   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -1.8587   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -2.1647   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -1.8362   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.1070   -1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769   -1.5166    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996   -0.4294    2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    2.0908    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500    3.4953    1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746    1.1649    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6580   -0.9568   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -3.4716   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -1.6214   -0.6848 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
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 13  1  0
 10  5  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       4.181  -1.999   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.514  -2.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.848  -1.999   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.848  -0.459   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.182   0.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.438  -0.716   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.438  -1.742   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.182  -2.769   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.515  -1.999   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.515  -0.459   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.849   0.311   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.183  -0.459   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.514  -4.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.848  -5.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.848  -6.619   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.514  -7.389   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.181  -6.619   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.847  -7.389   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.513  -6.619   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.513  -5.079   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.180  -4.309   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.847  -4.309   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.181  -5.079   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    2   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   13   17                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0247073
HETATM    1  C1  UNL     1       5.368   0.523   0.714  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.571  -0.501   0.557  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.108  -0.507   0.438  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.402   0.791   0.627  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.306   0.975  -0.312  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.995   1.261  -1.603  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.907   0.083  -1.916  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.699  -1.065  -0.942  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.266  -1.419  -0.909  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.500  -0.133  -0.556  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.672  -0.496   0.259  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.102  -0.690   1.634  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.705   0.520   0.494  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.535   1.744   1.078  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.610   2.544   1.447  1.00  0.00           C  
HETATM   16  N2  UNL     1      -3.884   2.132   1.236  1.00  0.00           N  
HETATM   17  C14 UNL     1      -4.120   0.928   0.658  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.426   0.555   0.366  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.640  -0.643  -0.318  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.618  -1.432  -0.696  1.00  0.00           C  
HETATM   21  O2  UNL     1      -4.709  -2.649  -1.396  1.00  0.00           O  
HETATM   22  C18 UNL     1      -3.318  -1.008  -0.372  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.058   0.156   0.299  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.453   0.412   0.792  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.985   1.516   0.768  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.068  -1.500   0.506  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.737  -1.295   1.140  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.057   0.965   1.676  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.103   1.615   0.403  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.242   1.404  -2.404  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.623   2.156  -1.503  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.628  -0.293  -2.921  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.970   0.348  -1.893  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.384  -1.859  -1.212  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.994  -2.165  -0.154  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.952  -1.836  -1.883  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.012   0.107  -1.605  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.977  -1.517   0.083  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.800  -0.429   2.251  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.508   2.091   1.260  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.450   3.495   1.921  1.00  0.00           H  
HETATM   42  H19 UNL     1      -6.275   1.165   0.648  1.00  0.00           H  
HETATM   43  H20 UNL     1      -6.658  -0.957  -0.573  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.776  -3.472  -0.820  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.488  -1.621  -0.685  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3   26
CONECT    3    4    8   27
CONECT    4    5   28   29
CONECT    5    6   10
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9   34
CONECT    9   10   35   36
CONECT   10   11   37
CONECT   11   12   13   38
CONECT   12   39
CONECT   13   14   14   23
CONECT   14   15   40
CONECT   15   16   16   41
CONECT   16   17
CONECT   17   18   18   23
CONECT   18   19   42
CONECT   19   20   20   43
CONECT   20   21   22
CONECT   21   44
CONECT   22   23   23   45
END

HMDB0247073
     RDKit          3D
O-Desmethylquinidine
 45 48  0  0  0  0  0  0  0  0999 V2000
    5.3677    0.5225    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705   -0.5008    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1081   -0.5071    0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4017    0.7913    0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    0.9747   -0.3118 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    1.2613   -1.6026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9071    0.0830   -1.9160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6988   -1.0650   -0.9417 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2661   -1.4188   -0.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003   -0.1335   -0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6719   -0.4959    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1021   -0.6896    1.6341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7046    0.5198    0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5354    1.7443    1.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6102    2.5440    1.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8844    2.1320    1.2363 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1203    0.9285    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    0.5554    0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6398   -0.6427   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6177   -1.4315   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7088   -2.6490   -1.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3184   -1.0084   -0.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575    0.1557    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4527    0.4121    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9849    1.5161    0.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678   -1.5002    0.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7368   -1.2955    1.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0566    0.9654    1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1032    1.6146    0.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2420    1.4038   -2.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    2.1564   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280   -0.2931   -2.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9702    0.3480   -1.8925 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3841   -1.8587   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935   -2.1647   -0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -1.8362   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0121    0.1070   -1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769   -1.5166    0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996   -0.4294    2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5079    2.0908    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4500    3.4953    1.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746    1.1649    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6580   -0.9568   -0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757   -3.4716   -0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4884   -1.6214   -0.6848 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
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 13  1  0
 10  5  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 19 43  1  0
 21 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O₂

Average Molecular Weight

310.397

Monoisotopic Molecular Weight

310.168127956

IUPAC Name

4-({5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(hydroxy)methyl)quinolin-6-ol

Traditional Name

cupreine

CAS Registry Number

Not Available

SMILES

OC(C1CC2CCN1CC2C=C)C1=C2C=C(O)C=CC2=NC=C1

InChI Identifier

InChI=1S/C19H22N2O2/c1-2-12-11-21-8-6-13(12)9-18(21)19(23)15-5-7-20-17-4-3-14(22)10-16(15)17/h2-5,7,10,12-13,18-19,22-23H,1,6,8-9,11H2

InChI Key

VJFMSYZSFUWQPZ-UHFFFAOYSA-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
Hydroxyquinoline
Quinoline
Quinuclidine
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.55	ALOGPS
logP	1.96	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.21 m³·mol⁻¹	ChemAxon
Polarizability	34.02 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
DeepCCS	[M+H]+	170.821	30932474
DeepCCS	[M-H]-	168.463	30932474
DeepCCS	[M-2H]-	201.349	30932474
DeepCCS	[M+Na]+	176.914	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	173.1	32859911
AllCCS	[M+NH4]+	179.3	32859911
AllCCS	[M+Na]+	180.1	32859911
AllCCS	[M-H]-	178.1	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	177.6	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethylquinidine,1TMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C)C1=CC=NC2=CC=C(O)C=C12	2727.2	Semi standard non polar	33892256
O-Desmethylquinidine,1TMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C)C1=CC=NC2=CC=C(O)C=C12	2672.5	Standard non polar	33892256
O-Desmethylquinidine,1TMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C)C1=CC=NC2=CC=C(O)C=C12	3564.2	Standard polar	33892256
O-Desmethylquinidine,2TBDMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3133.2	Semi standard non polar	33892256
O-Desmethylquinidine,2TBDMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3151.4	Standard non polar	33892256
O-Desmethylquinidine,2TBDMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	3563.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylquinidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0910000000-bcff4cbedc8b0b7b17c2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylquinidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylquinidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylquinidine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylquinidine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylquinidine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethylquinidine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylquinidine 10V, Positive-QTOF	splash10-03di-0009000000-d568762be5b8190f6c48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylquinidine 20V, Positive-QTOF	splash10-03di-0329000000-a5466ca951adab0ab8d4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylquinidine 40V, Positive-QTOF	splash10-05gi-0920000000-6656528c2fa1440522c8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylquinidine 10V, Negative-QTOF	splash10-0a4i-0009000000-6a3b822df85e34e5504e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylquinidine 20V, Negative-QTOF	splash10-0a4i-0859000000-b4ec3051c9b5b957a443	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethylquinidine 40V, Negative-QTOF	splash10-0a6u-0933000000-f0ec4f2ef205484ef4ae	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

46715

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51579

PDB ID

Not Available

ChEBI ID

Not Available

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)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for O-Desmethylquinidine (HMDB0247073)

MOL for HMDB0247073 (O-Desmethylquinidine)

3D MOL for HMDB0247073 (O-Desmethylquinidine)

3D SDF for HMDB0247073 (O-Desmethylquinidine)

3D-SDF for HMDB0247073 (O-Desmethylquinidine)

PDB for HMDB0247073 (O-Desmethylquinidine)

3D PDB for HMDB0247073 (O-Desmethylquinidine)

SMILES for HMDB0247073 (O-Desmethylquinidine)

INCHI for HMDB0247073 (O-Desmethylquinidine)

Structure for HMDB0247073 (O-Desmethylquinidine)

3D Structure for HMDB0247073 (O-Desmethylquinidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra