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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:54 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030283

Secondary Accession Numbers

HMDB30283

Metabolite Identification

Common Name

Hydrocinchonine

Description

Hydrocinchonine, also known as cinchonifine, 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 Hydrocinchonine.

Structure

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

HMDB0030283
     RDKit          3D
Hydrocinchonine
 46 49  0  0  0  0  0  0  0  0999 V2000
   -5.4225   -0.0872   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416   -0.9732   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075   -0.3743   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -1.4157   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -0.7662    0.3223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462   -0.5182    1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    0.2735    1.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374    0.8241    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    1.4876   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360    0.4131   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    0.8878    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139    1.2357    1.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617    0.2719   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468   -0.0608   -2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0921   -0.5539   -2.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2914   -0.7443   -2.2344 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725   -0.4434   -0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -0.6597   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9435   -0.4054    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127    0.0857    1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666    0.3167    1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228    0.0624   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436    0.8960   -0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871   -0.6000    0.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7318    0.0644   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -1.4373    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925   -1.8662   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    0.0094   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -2.2861    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673   -1.7336   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -0.0349    2.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3681   -1.5229    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861   -0.3134    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3511    1.1539    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794    1.5189    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616    2.0902   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    2.1648    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468    0.2266   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524    1.9352   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    2.2170    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0913    0.0936   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636   -0.8019   -3.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4901   -1.0388   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9331   -0.5933    1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898    0.3114    2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812    0.6908    1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  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  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END


  Mrv0541 05061305082D          

 22 25  0  0  0  0            999 V2000
   -4.3830    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8759    0.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0811   -0.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9832    0.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214    0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8015    1.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    0.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3340    0.9436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  2  0  0  0  0
 16  7  2  0  0  0  0
 16 15  1  0  0  0  0
 17  6  2  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 19 16  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 12  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030283

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1CN2CCC1CC2C(O)C1=CC=NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2O/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/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3

> <INCHI_KEY>
WFJNHVWTKZUUTR-UHFFFAOYSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.4067

> <EXACT_MASS>
296.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.380696560266855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.975123202666667

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.877400317939916

> <JCHEM_PKA_STRONGEST_BASIC>
9.276425230093475

> <JCHEM_POLAR_SURFACE_AREA>
36.36

> <JCHEM_REFRACTIVITY>
88.1863

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydrocinchonine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030283
     RDKit          3D
Hydrocinchonine
 46 49  0  0  0  0  0  0  0  0999 V2000
   -5.4225   -0.0872   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416   -0.9732   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075   -0.3743   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -1.4157   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -0.7662    0.3223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462   -0.5182    1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    0.2735    1.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374    0.8241    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    1.4876   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360    0.4131   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    0.8878    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139    1.2357    1.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617    0.2719   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468   -0.0608   -2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0921   -0.5539   -2.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2914   -0.7443   -2.2344 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725   -0.4434   -0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -0.6597   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9435   -0.4054    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127    0.0857    1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666    0.3167    1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228    0.0624   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436    0.8960   -0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871   -0.6000    0.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7318    0.0644   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -1.4373    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925   -1.8662   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    0.0094   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -2.2861    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673   -1.7336   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -0.0349    2.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3681   -1.5229    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861   -0.3134    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3511    1.1539    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794    1.5189    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616    2.0902   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    2.1648    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468    0.2266   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524    1.9352   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    2.2170    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0913    0.0936   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636   -0.8019   -3.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4901   -1.0388   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9331   -0.5933    1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898    0.3114    2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812    0.6908    1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  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  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.182   2.662   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.235   1.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.751  -0.980   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.569   0.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.213   0.225   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.229   3.030   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.710   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.839   0.423   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      -4.357   1.761   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   13                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   15                                                       
CONECT    6    4   17                                                       
CONECT    7    9   16                                                       
CONECT    8   10   14                                                       
CONECT    9    7   20                                                       
CONECT   10    8   21                                                       
CONECT   11   14   18                                                       
CONECT   12   13   21                                                       
CONECT   13    2   12   14                                                  
CONECT   14    8   11   13                                                  
CONECT   15    5   16   17                                                  
CONECT   16    7   15   19                                                  
CONECT   17    6   15   20                                                  
CONECT   18   11   19   21                                                  
CONECT   19   16   18   22                                                  
CONECT   20    9   17                                                       
CONECT   21   10   12   18                                                  
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0030283
HETATM    1  C1  UNL     1      -5.422  -0.087  -0.520  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.242  -0.973  -0.344  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.908  -0.374  -0.581  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.802  -1.416  -0.360  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.713  -0.766   0.322  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.146  -0.518   1.658  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.435   0.274   1.722  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.637   0.824   0.319  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.330   1.488  -0.076  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.336   0.413  -0.406  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.058   0.888   0.010  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.114   1.236   1.293  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.162   0.272  -0.711  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.047  -0.061  -2.051  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.092  -0.554  -2.777  1.00  0.00           C  
HETATM   16  N2  UNL     1       4.291  -0.744  -2.234  1.00  0.00           N  
HETATM   17  C14 UNL     1       4.472  -0.443  -0.942  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.700  -0.660  -0.336  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.943  -0.405   0.993  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.913   0.086   1.737  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.667   0.317   1.163  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.423   0.062  -0.168  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.344   0.896  -0.030  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.287  -0.600   0.015  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.732   0.064  -1.569  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.345  -1.437   0.685  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.392  -1.866  -1.012  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.907   0.009  -1.626  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.206  -2.286   0.206  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.467  -1.734  -1.367  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.449  -0.035   2.342  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.368  -1.523   2.121  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.286  -0.313   2.078  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.351   1.154   2.382  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.479   1.519   0.302  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.562   2.090  -1.010  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.922   2.165   0.680  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.347   0.227  -1.467  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.052   1.935  -0.522  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.132   2.217   1.424  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.091   0.094  -2.531  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.964  -0.802  -3.842  1.00  0.00           H  
HETATM   43  H21 UNL     1       6.490  -1.039  -0.981  1.00  0.00           H  
HETATM   44  H22 UNL     1       6.933  -0.593   1.437  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.990   0.311   2.786  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.881   0.691   1.787  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   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   22
CONECT   14   15   41
CONECT   15   16   16   42
CONECT   16   17
CONECT   17   18   18   22
CONECT   18   19   43
CONECT   19   20   20   44
CONECT   20   21   45
CONECT   21   22   22   46
END

HMDB0030283
     RDKit          3D
Hydrocinchonine
 46 49  0  0  0  0  0  0  0  0999 V2000
   -5.4225   -0.0872   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2416   -0.9732   -0.3438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9075   -0.3743   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -1.4157   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -0.7662    0.3223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462   -0.5182    1.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    0.2735    1.7219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374    0.8241    0.3194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304    1.4876   -0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3360    0.4131   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    0.8878    0.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139    1.2357    1.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1617    0.2719   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0468   -0.0608   -2.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0921   -0.5539   -2.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2914   -0.7443   -2.2344 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4725   -0.4434   -0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -0.6597   -0.3364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9435   -0.4054    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9127    0.0857    1.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666    0.3167    1.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228    0.0624   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436    0.8960   -0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2871   -0.6000    0.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7318    0.0644   -1.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3455   -1.4373    0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925   -1.8662   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    0.0094   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -2.2861    0.2061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4673   -1.7336   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485   -0.0349    2.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3681   -1.5229    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2861   -0.3134    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3511    1.1539    2.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4794    1.5189    0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616    2.0902   -1.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    2.1648    0.6795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468    0.2266   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524    1.9352   -0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1322    2.2170    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0913    0.0936   -2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9636   -0.8019   -3.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4901   -1.0388   -0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9331   -0.5933    1.4368 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898    0.3114    2.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8812    0.6908    1.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  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
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  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  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9S)-10,11-Dihydrocinchonan-9-ol	HMDB
(9S)-10,11-Dihydrocinchonan-9-ol, 9ci	HMDB
10,11-Dihydrocinchonine	HMDB
Cinchonifine	HMDB
Cinchotine	HMDB
Pseudocinchonine	HMDB
Y-cinchonine	HMDB

Chemical Formula

C₁₉H₂₄N₂O

Average Molecular Weight

296.4067

Monoisotopic Molecular Weight

296.1888634

IUPAC Name

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

Traditional Name

hydrocinchonine

CAS Registry Number

485-65-4

SMILES

CCC1CN2CCC1CC2C(O)C1=CC=NC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H24N2O/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/h3-7,9,13-14,18-19,22H,2,8,10-12H2,1H3

InChI Key

WFJNHVWTKZUUTR-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: HMDB0030283)

Cellular substructure

Membrane (HMDB: HMDB0030283)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030283)

Source

Endogenous

Endogenous (HMDB: HMDB0030283)

Plant

Plant (HMDB: HMDB0030283)

Exogenous

Food

Food (HMDB: HMDB0030283)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	268 - 269 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.7 mg/mL at 16 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	3.26	ALOGPS
logP	2.98	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.88	ChemAxon
pKa (Strongest Basic)	9.28	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	88.19 m³·mol⁻¹	ChemAxon
Polarizability	33.38 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]+	169.873	31661259
DarkChem	[M-H]-	170.478	31661259
DeepCCS	[M-2H]-	199.036	30932474
DeepCCS	[M+Na]+	174.601	30932474
AllCCS	[M+H]+	174.7	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.9	32859911
AllCCS	[M+Na]+	178.8	32859911
AllCCS	[M-H]-	181.8	32859911
AllCCS	[M+Na-2H]-	181.8	32859911
AllCCS	[M+HCOO]-	181.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydrocinchonine	CCC1CN2CCC1CC2C(O)C1=CC=NC2=CC=CC=C12	3230.4	Standard polar	33892256
Hydrocinchonine	CCC1CN2CCC1CC2C(O)C1=CC=NC2=CC=CC=C12	2574.4	Standard non polar	33892256
Hydrocinchonine	CCC1CN2CCC1CC2C(O)C1=CC=NC2=CC=CC=C12	2622.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydrocinchonine,1TMS,isomer #1	CCC1CN2CCC1CC2C(O[Si](C)(C)C)C1=CC=NC2=CC=CC=C12	2511.2	Semi standard non polar	33892256
Hydrocinchonine,1TBDMS,isomer #1	CCC1CN2CCC1CC2C(O[Si](C)(C)C(C)(C)C)C1=CC=NC2=CC=CC=C12	2742.4	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 - Hydrocinchonine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-0910000000-7092a6c9bb7578b9fc6f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydrocinchonine GC-MS (1 TMS) - 70eV, Positive	splash10-001i-6593000000-702efe46ab1c08490dfd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydrocinchonine 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 - Hydrocinchonine LC-ESI-QTOF , positive-QTOF	splash10-0002-0090000000-0c1bbc2a6ec759f2b7d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydrocinchonine LC-ESI-QTOF , positive-QTOF	splash10-0002-0090000000-69ff0519d4dd5076aa46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydrocinchonine 20V, Positive-QTOF	splash10-0002-0090000000-69ff0519d4dd5076aa46	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydrocinchonine 10V, Positive-QTOF	splash10-0002-0090000000-0c1bbc2a6ec759f2b7d2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 10V, Positive-QTOF	splash10-004j-0090000000-61bd881dae2d7ce905b8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 20V, Positive-QTOF	splash10-004r-0890000000-fe03dadaff0cff581939	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 40V, Positive-QTOF	splash10-053i-0910000000-e3eaa11e20d170cee6cd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 10V, Positive-QTOF	splash10-004j-0090000000-61bd881dae2d7ce905b8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 20V, Positive-QTOF	splash10-004r-0890000000-fe03dadaff0cff581939	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 40V, Positive-QTOF	splash10-053i-0910000000-e3eaa11e20d170cee6cd	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 10V, Negative-QTOF	splash10-0002-0190000000-2d23c3434e6449a8991b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 20V, Negative-QTOF	splash10-002b-0290000000-1a6a24c970397c77f1b6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 40V, Negative-QTOF	splash10-0570-1910000000-639719097654c1aafe97	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 10V, Negative-QTOF	splash10-0002-0190000000-2d23c3434e6449a8991b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 20V, Negative-QTOF	splash10-002b-0290000000-1a6a24c970397c77f1b6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 40V, Negative-QTOF	splash10-0570-1910000000-639719097654c1aafe97	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 10V, Negative-QTOF	splash10-0002-0090000000-6097eef1edfc41faed9b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 20V, Negative-QTOF	splash10-0002-0490000000-052b537c65df10739bb7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 40V, Negative-QTOF	splash10-004i-0900000000-04e486c54040ca93166b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 10V, Positive-QTOF	splash10-0002-0090000000-7a52ccd6b13581152274	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 20V, Positive-QTOF	splash10-0002-0090000000-3e9015edd4d84ebc53b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydrocinchonine 40V, Positive-QTOF	splash10-001u-0910000000-00a4eb94a2851e5381c2	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB002118

KNApSAcK ID

C00052262

Chemspider ID

91899

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101711

PDB ID

Not Available

ChEBI ID

115148

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Hydrocinchonine (HMDB0030283)

MOL for HMDB0030283 (Hydrocinchonine)

3D MOL for HMDB0030283 (Hydrocinchonine)

3D SDF for HMDB0030283 (Hydrocinchonine)

3D-SDF for HMDB0030283 (Hydrocinchonine)

PDB for HMDB0030283 (Hydrocinchonine)

3D PDB for HMDB0030283 (Hydrocinchonine)

SMILES for HMDB0030283 (Hydrocinchonine)

INCHI for HMDB0030283 (Hydrocinchonine)

Structure for HMDB0030283 (Hydrocinchonine)

3D Structure for HMDB0030283 (Hydrocinchonine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra