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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:47:26 UTC

Update Date

2021-09-23 20:47:26 UTC

HMDB ID

HMDB0302802

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydrocinchonine

Description

(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol 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 (S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol.

Structure

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

HMDB0302802
     RDKit          3D
Dihydrocinchonine
 46 49  0  0  0  0  0  0  0  0999 V2000
   -5.1590   -0.9004   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0594   -1.2538    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744   -0.1025    0.4611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1225   -0.4052    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.5619    1.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172    1.8252    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    1.7487   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    0.2852   -0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367   -0.5513   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1785    0.1677    0.2409 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0880   -0.2801    0.7984 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7468   -1.4230    1.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.7429   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -2.0007   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -2.4194   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.5907   -1.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -0.3327   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797    0.5092   -1.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3655    1.8373   -0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2382    2.2475   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.3986    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.1078   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7030    0.0404   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7504   -0.7156   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9146   -1.7053   -0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4651   -2.0550   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5005   -1.7741    1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    0.7660    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.3643    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811   -1.4498    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    2.5593    1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285    2.1882    1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553    2.3275   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851    2.1853   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736    0.1311   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6117   -0.4270   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2439   -1.6088   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0756    1.1649   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045    0.4435    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -1.9930    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931   -2.7058   -0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474   -3.4128   -1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3837    0.1684   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    2.5039   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1475    3.2724    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2640    1.7741    0.6904 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  1
  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  6
 11 39  1  1
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END


  Mrv0541 02241221462D          

 22 25  0  0  1  0            999 V2000
    2.3306    1.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601    0.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849    0.3592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9242    1.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3111    0.3308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1968    0.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8258   -0.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727   -0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   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
    0.0000    0.0000    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
    0.7145    1.2375    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904    0.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 12 21  1  0  0  0  0
 16 21  1  0  0  0  0
 11 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302802

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H]1CN2CCC1C[C@@H]2[C@@H](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/t13-,14?,18+,19-/m0/s1

> <INCHI_KEY>
WFJNHVWTKZUUTR-FGVBSWQGSA-N

> <FORMULA>
C19H24N2O

> <MOLECULAR_WEIGHT>
296.4067

> <EXACT_MASS>
296.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.9177370118895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(S)-[(2R,5R)-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>
88.18630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302802
     RDKit          3D
Dihydrocinchonine
 46 49  0  0  0  0  0  0  0  0999 V2000
   -5.1590   -0.9004   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0594   -1.2538    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744   -0.1025    0.4611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1225   -0.4052    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.5619    1.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172    1.8252    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    1.7487   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    0.2852   -0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367   -0.5513   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1785    0.1677    0.2409 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0880   -0.2801    0.7984 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7468   -1.4230    1.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.7429   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -2.0007   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -2.4194   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.5907   -1.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -0.3327   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797    0.5092   -1.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3655    1.8373   -0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2382    2.2475   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.3986    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.1078   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7030    0.0404   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7504   -0.7156   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9146   -1.7053   -0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4651   -2.0550   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5005   -1.7741    1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    0.7660    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.3643    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811   -1.4498    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    2.5593    1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285    2.1882    1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553    2.3275   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851    2.1853   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736    0.1311   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6117   -0.4270   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2439   -1.6088   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0756    1.1649   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045    0.4435    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -1.9930    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931   -2.7058   -0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474   -3.4128   -1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3837    0.1684   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    2.5039   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1475    3.2724    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2640    1.7741    0.6904 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  1
  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  6
 11 39  1  1
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  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       4.350   1.948   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.152   0.633   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.692   0.671   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.325   1.978   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       8.047   0.617   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.701   0.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.008  -1.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.416  -0.657   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.349  -1.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   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  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.089   0.905   0.000  0.00  0.00           O+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    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   16                                                  
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0302802
HETATM    1  C1  UNL     1      -5.159  -0.900  -0.856  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.059  -1.254   0.163  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.174  -0.102   0.461  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.122  -0.405   1.502  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.039   0.562   1.395  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.617   1.825   0.971  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.996   1.749  -0.494  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.342   0.285  -0.785  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.037  -0.551  -0.681  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.179   0.168   0.241  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.088  -0.280   0.798  1.00  0.00           C  
HETATM   12  O1  UNL     1       0.747  -1.423   1.644  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.155  -0.743  -0.069  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.294  -2.001  -0.592  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.457  -2.419  -1.238  1.00  0.00           C  
HETATM   16  N2  UNL     1       4.492  -1.591  -1.371  1.00  0.00           N  
HETATM   17  C14 UNL     1       4.412  -0.333  -0.877  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.480   0.509  -1.098  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.366   1.837  -0.645  1.00  0.00           C  
HETATM   20  C17 UNL     1       4.238   2.248  -0.017  1.00  0.00           C  
HETATM   21  C18 UNL     1       3.150   1.399   0.213  1.00  0.00           C  
HETATM   22  C19 UNL     1       3.280   0.108  -0.236  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.703   0.040  -0.538  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.750  -0.716  -1.864  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.915  -1.705  -0.901  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.465  -2.055  -0.391  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.501  -1.774   1.017  1.00  0.00           H  
HETATM   28  H6  UNL     1      -3.749   0.766   0.826  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.502  -0.364   2.533  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.781  -1.450   1.344  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.751   2.559   1.026  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.429   2.188   1.595  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.955   2.328  -0.573  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.285   2.185  -1.189  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.874   0.131  -1.716  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.612  -0.427  -1.741  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.244  -1.609  -0.535  1.00  0.00           H  
HETATM   38  H16 UNL     1       0.076   1.165  -0.310  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.405   0.444   1.609  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.545  -1.993   1.650  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.493  -2.706  -0.508  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.547  -3.413  -1.640  1.00  0.00           H  
HETATM   43  H21 UNL     1       6.384   0.168  -1.615  1.00  0.00           H  
HETATM   44  H22 UNL     1       6.219   2.504  -0.827  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.147   3.272   0.327  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.264   1.774   0.690  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

HMDB0302802
     RDKit          3D
Dihydrocinchonine
 46 49  0  0  0  0  0  0  0  0999 V2000
   -5.1590   -0.9004   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0594   -1.2538    0.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1744   -0.1025    0.4611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1225   -0.4052    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0385    0.5619    1.3949 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172    1.8252    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9960    1.7487   -0.4940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3418    0.2852   -0.7845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0367   -0.5513   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1785    0.1677    0.2409 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0880   -0.2801    0.7984 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7468   -1.4230    1.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1555   -0.7429   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937   -2.0007   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4571   -2.4194   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -1.5907   -1.3706 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -0.3327   -0.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797    0.5092   -1.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3655    1.8373   -0.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2382    2.2475   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498    1.3986    0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801    0.1078   -0.2361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7030    0.0404   -0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7504   -0.7156   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9146   -1.7053   -0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4651   -2.0550   -0.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5005   -1.7741    1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7488    0.7660    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.3643    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811   -1.4498    1.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    2.5593    1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4285    2.1882    1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9553    2.3275   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851    2.1853   -1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736    0.1311   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6117   -0.4270   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2439   -1.6088   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0756    1.1649   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4045    0.4435    1.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -1.9930    1.6499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4931   -2.7058   -0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5474   -3.4128   -1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3837    0.1684   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    2.5039   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1475    3.2724    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2640    1.7741    0.6904 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  1
  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  6
 11 39  1  1
 12 40  1  0
 14 41  1  0
 15 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄N₂O

Average Molecular Weight

296.4067

Monoisotopic Molecular Weight

296.1888634

IUPAC Name

(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

Traditional Name

(S)-[(2R,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](quinolin-4-yl)methanol

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CCC1C[C@@H]2[C@@H](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/t13-,14?,18+,19-/m0/s1

InChI Key

WFJNHVWTKZUUTR-FGVBSWQGSA-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

Not Available

Olive (FooDB: FOOD00121)

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	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	33.92 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
AllCCS	[M+H]+	174.674	32859911
AllCCS	[M+H-H2O]+	171.221	32859911
AllCCS	[M+Na]+	178.798	32859911
AllCCS	[M+NH4]+	177.877	32859911
AllCCS	[M-H]-	181.848	32859911
AllCCS	[M+Na-2H]-	181.81	32859911
AllCCS	[M+HCOO]-	181.91	32859911
DeepCCS	[M-2H]-	204.56	30932474
DeepCCS	[M+Na]+	179.788	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 10V, Positive-QTOF	splash10-004j-0090000000-61bd881dae2d7ce905b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 20V, Positive-QTOF	splash10-004r-0890000000-896abc40c27c2088e70b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 40V, Positive-QTOF	splash10-053i-0910000000-8849a0082df3a1a81946	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 10V, Negative-QTOF	splash10-0002-0190000000-c19d585b8b4d89b3a449	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 20V, Negative-QTOF	splash10-002b-0290000000-5681a8bd6bc5ec519792	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 40V, Negative-QTOF	splash10-0550-1910000000-78c139d3015ac6257eeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 10V, Positive-QTOF	splash10-0002-0090000000-7a52ccd6b13581152274	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 20V, Positive-QTOF	splash10-0002-0090000000-3e9015edd4d84ebc53b1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 40V, Positive-QTOF	splash10-001u-0910000000-00a4eb94a2851e5381c2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 10V, Negative-QTOF	splash10-0002-0090000000-6097eef1edfc41faed9b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 20V, Negative-QTOF	splash10-0002-0490000000-052b537c65df10739bb7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrocinchonine 40V, Negative-QTOF	splash10-004i-0900000000-04e486c54040ca93166b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB006314

KNApSAcK ID

Not Available

Chemspider ID

17340671

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16212907

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

Not Available

Showing metabocard for Dihydrocinchonine (HMDB0302802)

MOL for HMDB0302802 (Dihydrocinchonine)

3D MOL for HMDB0302802 (Dihydrocinchonine)

3D SDF for HMDB0302802 (Dihydrocinchonine)

3D-SDF for HMDB0302802 (Dihydrocinchonine)

PDB for HMDB0302802 (Dihydrocinchonine)

3D PDB for HMDB0302802 (Dihydrocinchonine)

SMILES for HMDB0302802 (Dihydrocinchonine)

INCHI for HMDB0302802 (Dihydrocinchonine)

Structure for HMDB0302802 (Dihydrocinchonine)

3D Structure for HMDB0302802 (Dihydrocinchonine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra