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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:35:54 UTC

Update Date

2022-09-22 18:34:24 UTC

HMDB ID

HMDB0030282

Secondary Accession Numbers

HMDB30282

Metabolite Identification

Common Name

Cinchonidine

Description

Cinchonidine 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. Cinchonidine has been detected, but not quantified in, a few different foods, such as fruits, herbs and spices, and olives (Olea europaea). This could make cinchonidine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cinchonidine.

Structure

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

HMDB0242260
     RDKit          3D
(+)-Quinolin-4-yl(5-vinylquinuclidin-2-yl)methanol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.4716   -2.3734   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680   -1.2493   -1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2142    0.0455   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    0.7048   -1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.5293   -0.5160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    2.2496    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408    1.3101    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777   -0.1113    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4926   -0.4986    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370    0.7154    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090    0.5798   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    1.9148   -0.1891 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460   -0.1027    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555   -0.6252    1.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7087   -1.2674    2.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.4003    1.9334 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -0.8908    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2764   -1.0773    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4773   -0.5846   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    0.0599   -1.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1975    0.2444   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9847   -0.2451    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.4915    0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -3.3346   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6674   -1.3368   -2.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0841    0.7033   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980   -0.1195   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1632    1.3295   -2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041    2.6158   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955    3.0976    0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    1.3274    2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2050    1.5394    1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278   -0.8091    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095   -1.2610   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539   -0.8724    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    1.3076    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6459    0.1926   -1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640    2.4678   -0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465   -0.5367    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635   -1.6631    3.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732   -1.5892    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4589   -0.7135   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    0.4594   -2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    0.7595   -1.7809 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  2  0
  8  3  1  0
 22 13  1  0
 10  5  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END


  Mrv0541 02241214302D          

 22 25  0  0  0  0            999 V2000
    2.3104   -1.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5003   -0.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8672   -0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7408    0.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2341    1.1708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205    0.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1205    0.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2341   -0.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5380   -0.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745    0.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    1.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3481    1.8670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9807    0.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076   -0.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -0.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -1.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706   -1.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8037   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8037   -0.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5003   -0.1579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4369    0.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    1.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 22  2  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030282

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2

> <INCHI_KEY>
KMPWYEUPVWOPIM-UHFFFAOYSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.3908

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.10427189095202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.6711352163333344

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.877315843243736

> <JCHEM_PKA_STRONGEST_BASIC>
9.146374717755835

> <JCHEM_POLAR_SURFACE_AREA>
36.36

> <JCHEM_REFRACTIVITY>
88.2304

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cinchonidine sulfate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242260
     RDKit          3D
(+)-Quinolin-4-yl(5-vinylquinuclidin-2-yl)methanol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.4716   -2.3734   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680   -1.2493   -1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2142    0.0455   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    0.7048   -1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.5293   -0.5160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    2.2496    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408    1.3101    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777   -0.1113    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4926   -0.4986    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370    0.7154    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090    0.5798   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    1.9148   -0.1891 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460   -0.1027    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555   -0.6252    1.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7087   -1.2674    2.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.4003    1.9334 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -0.8908    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2764   -1.0773    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4773   -0.5846   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    0.0599   -1.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1975    0.2444   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9847   -0.2451    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.4915    0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -3.3346   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6674   -1.3368   -2.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0841    0.7033   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980   -0.1195   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1632    1.3295   -2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041    2.6158   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955    3.0976    0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    1.3274    2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2050    1.5394    1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278   -0.8091    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095   -1.2610   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539   -0.8724    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    1.3076    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6459    0.1926   -1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640    2.4678   -0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465   -0.5367    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635   -1.6631    3.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732   -1.5892    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4589   -0.7135   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    0.4594   -2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    0.7595   -1.7809 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  2  0
  8  3  1  0
 22 13  1  0
 10  5  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.313  -2.776   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.667  -1.358   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.485  -0.649   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.249   1.241   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.304   2.185   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.958   1.831   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.958   0.059   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.304  -0.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.004  -0.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.886   1.477   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.531   1.950   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.650   3.485   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.831   1.122   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.068  -0.413   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.767  -1.241   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.767  -2.776   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.185  -3.485   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.367  -2.659   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.367  -1.122   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -4.667  -0.295   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -4.549   1.241   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.249   1.950   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   22                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   14   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   13   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0242260
HETATM    1  C1  UNL     1      -3.472  -2.373  -0.938  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.468  -1.249  -1.628  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.214   0.045  -0.996  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.943   0.705  -1.544  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.360   1.529  -0.516  1.00  0.00           N  
HETATM    6  C5  UNL     1      -2.445   2.250   0.122  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.141   1.310   1.056  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.978  -0.111   0.472  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.493  -0.499   0.633  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.637   0.715   0.494  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.709   0.580  -0.050  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.188   1.915  -0.189  1.00  0.00           O  
HETATM   13  C11 UNL     1       1.746  -0.103   0.679  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.655  -0.625   1.934  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.709  -1.267   2.561  1.00  0.00           C  
HETATM   16  N2  UNL     1       3.891  -1.400   1.933  1.00  0.00           N  
HETATM   17  C14 UNL     1       4.021  -0.891   0.678  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.276  -1.077   0.120  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.477  -0.585  -1.148  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.454   0.060  -1.803  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.197   0.244  -1.239  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.985  -0.245   0.030  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.300  -2.492   0.118  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.668  -3.335  -1.452  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.667  -1.337  -2.712  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.084   0.703  -1.224  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.298  -0.119  -1.873  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.163   1.330  -2.413  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.104   2.616  -0.692  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.995   3.098   0.671  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.658   1.327   2.048  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.205   1.539   1.081  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.628  -0.809   0.988  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.310  -1.261  -0.141  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.454  -0.872   1.675  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.666   1.308   1.423  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.646   0.193  -1.083  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.564   2.468  -0.687  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.746  -0.537   2.459  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.563  -1.663   3.571  1.00  0.00           H  
HETATM   41  H19 UNL     1       6.073  -1.589   0.652  1.00  0.00           H  
HETATM   42  H20 UNL     1       6.459  -0.713  -1.623  1.00  0.00           H  
HETATM   43  H21 UNL     1       4.579   0.459  -2.802  1.00  0.00           H  
HETATM   44  H22 UNL     1       2.410   0.759  -1.781  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4    8   26
CONECT    4    5   27   28
CONECT    5    6   10
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33
CONECT    9   10   34   35
CONECT   10   11   36
CONECT   11   12   13   37
CONECT   12   38
CONECT   13   14   14   22
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   17
CONECT   17   18   18   22
CONECT   18   19   41
CONECT   19   20   20   42
CONECT   20   21   43
CONECT   21   22   22   44
END

HMDB0242260
     RDKit          3D
(+)-Quinolin-4-yl(5-vinylquinuclidin-2-yl)methanol
 44 47  0  0  0  0  0  0  0  0999 V2000
   -3.4716   -2.3734   -0.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4680   -1.2493   -1.6282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2142    0.0455   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    0.7048   -1.5440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3601    1.5293   -0.5160 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    2.2496    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1408    1.3101    1.0556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9777   -0.1113    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4926   -0.4986    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6370    0.7154    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7090    0.5798   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882    1.9148   -0.1891 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460   -0.1027    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6555   -0.6252    1.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7087   -1.2674    2.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.4003    1.9334 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -0.8908    0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2764   -1.0773    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4773   -0.5846   -1.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    0.0599   -1.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1975    0.2444   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9847   -0.2451    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998   -2.4915    0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6678   -3.3346   -1.4516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6674   -1.3368   -2.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0841    0.7033   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2980   -0.1195   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1632    1.3295   -2.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041    2.6158   -0.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9955    3.0976    0.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6582    1.3274    2.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2050    1.5394    1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6278   -0.8091    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3095   -1.2610   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539   -0.8724    1.6752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6658    1.3076    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6459    0.1926   -1.0826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5640    2.4678   -0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465   -0.5367    2.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5635   -1.6631    3.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0732   -1.5892    0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4589   -0.7135   -1.6231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794    0.4594   -2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    0.7595   -1.7809 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  2  0
  8  3  1  0
 22 13  1  0
 10  5  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cinchonine, hexaiodotl(-2) (1:1), (9S)-isomer	MeSH
Cinchonine, hydrochloride, (9S)-isomer	MeSH
Cinchonine, monohydrochloride, (9S)-isomer	MeSH
Cinchonine, sulfate (2:1), (9S)-isomer	MeSH
(-)-Cinchonidine	HMDB
(8a,9R)-Cinchonan-9-ol, 9ci	HMDB
(8alpha ,9R)-Cinchonan-9-ol	HMDB
(8S,9R)-Cinchonidine	HMDB
a-Quinidine	HMDB
alpha -Quinidine	HMDB
alpha-Quinidine	HMDB
Cinchovatine	HMDB
L-Cinchonidine	HMDB
Nchem.180-comp1b	HMDB
Cinchonidine monohydrochloride	MeSH, HMDB
Cinchonidine sulfate(2:1)	MeSH, HMDB
Cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isomer	MeSH, HMDB
Cinchonidine hydrochloride	MeSH, HMDB
Cinchonidine	MeSH

Chemical Formula

C₁₉H₂₂N₂O

Average Molecular Weight

294.3908

Monoisotopic Molecular Weight

294.173213336

IUPAC Name

{5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl}(quinolin-4-yl)methanol

Traditional Name

cinchonidine sulfate

CAS Registry Number

485-71-2

SMILES

OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2

InChI Identifier

InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2

InChI Key

KMPWYEUPVWOPIM-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
Quinoline
Quinuclidine
Aralkylamine
Piperidine
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen 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

Cell membrane (HMDB: HMDB0030282)

Cellular substructure

Membrane (HMDB: HMDB0030282)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030282)

Source

Endogenous

Endogenous (HMDB: HMDB0030282)

Plant

Plant (HMDB: HMDB0030282)

Exogenous

Food

Food (HMDB: HMDB0030282)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antipyretic (HMDB: HMDB0030282)
antiviral agent (HMDB: HMDB0030282)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0030282)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.2 mg/mL at 25 °C	Not Available
LogP	2.82	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	3.2	ALOGPS
logP	2.67	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	9.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	88.23 m³·mol⁻¹	ChemAxon
Polarizability	33.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.894	31661259
DarkChem	[M-H]-	167.59	31661259
DeepCCS	[M+H]+	163.71	30932474
DeepCCS	[M-H]-	161.352	30932474
DeepCCS	[M-2H]-	194.238	30932474
DeepCCS	[M+Na]+	169.803	30932474
AllCCS	[M+H]+	174.0	32859911
AllCCS	[M+H-H2O]+	170.4	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	179.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinchonidine	OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2	3281.7	Standard polar	33892256
Cinchonidine	OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2	2548.2	Standard non polar	33892256
Cinchonidine	OC(C1CC2CCN1CC2C=C)C1=CC=NC2=C1C=CC=C2	2597.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cinchonidine,1TMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C)C1=CC=NC2=CC=CC=C12	2509.7	Semi standard non polar	33892256
Cinchonidine,1TBDMS,isomer #1	C=CC1CN2CCC1CC2C(O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=CC=C12	2725.0	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 - Cinchonidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5i-2910000000-0f0ed0cb19d7fe7fadca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinchonidine GC-MS (1 TMS) - 70eV, Positive	splash10-00a9-9875000000-eaf01aacdc509130f140	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinchonidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinchonidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinchonidine 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 - Cinchonidine LC-ESI-qTof , Positive-QTOF	splash10-0002-0960000000-6456c6c3bb2715a7fa00	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine , positive-QTOF	splash10-0002-0960000000-6456c6c3bb2715a7fa00	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 20V, Positive-QTOF	splash10-0002-0090000000-6187f815acdbbec47fb2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-00lu-2900000000-14f3c34cde5aa2a11079	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-00nb-2940000000-eb3a248cf968cf941040	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 30V, Positive-QTOF	splash10-069v-0980000000-48c213347c975179636c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 15V, Positive-QTOF	splash10-0002-0090000000-0e970cbc2afa57a9654f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0190000000-858bee716ec1d75adc07	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0561-1940000000-26e7e3cbae5ea5fb610f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 10V, Positive-QTOF	splash10-0002-0090000000-b480b5a0b696f940452f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0190000000-f93b51b0818b008b49b7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-00lr-1900000000-603d73783b786d42fdc1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0190000000-6595d19fdd23a9e3238b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0190000000-5a94ad8c559d5c375bdd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0190000000-c81a1076dcd69ebccce3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0090000000-ae336d292aca65dcc174	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0090000000-166d01b77083c7e27751	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-001j-2950000000-88afa86bed375ec3a70c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cinchonidine 6V, Positive-QTOF	splash10-0002-0190000000-6abca9144bc157cadb34	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinchonidine 10V, Positive-QTOF	splash10-004j-0090000000-ad4802f48f7823037200	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinchonidine 20V, Positive-QTOF	splash10-004r-0890000000-dfa80dddb949e8796af0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinchonidine 40V, Positive-QTOF	splash10-0ac9-0910000000-23c8a136dc8bfb4979ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinchonidine 10V, Negative-QTOF	splash10-0006-0190000000-49f8db7ac84bad0edd86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinchonidine 20V, Negative-QTOF	splash10-002f-0290000000-9d17bd1a54e6ff3cde9b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinchonidine 40V, Negative-QTOF	splash10-057r-1910000000-835c9a14cf1712dd341b	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB002116

KNApSAcK ID

C00002147

Chemspider ID

2655

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cinchonidine

METLIN ID

Not Available

PubChem Compound

2757

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

Shah BH, Nawaz Z, Virani SS, Ali IQ, Saeed SA, Gilani AH: The inhibitory effect of cinchonine on human platelet aggregation due to blockade of calcium influx. Biochem Pharmacol. 1998 Oct 15;56(8):955-60. [PubMed:9776305 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cinchonidine (HMDB0030282)

MOL for HMDB0030282 (Cinchonidine)

3D MOL for HMDB0030282 (Cinchonidine)

3D SDF for HMDB0030282 (Cinchonidine)

3D-SDF for HMDB0030282 (Cinchonidine)

PDB for HMDB0030282 (Cinchonidine)

3D PDB for HMDB0030282 (Cinchonidine)

SMILES for HMDB0030282 (Cinchonidine)

INCHI for HMDB0030282 (Cinchonidine)

Structure for HMDB0030282 (Cinchonidine)

3D Structure for HMDB0030282 (Cinchonidine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra