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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015398

Secondary Accession Numbers

HMDB15398

Metabolite Identification

Common Name

Varenicline

Description

Varenicline is a prescription medication used to treat smoking addiction. This medication is the first approved nicotinic receptor partial agonist. Specifically, varenicline is a partial agonist of the alpha4/beta2 subtype of the nicotinic acetylcholine receptor. In addition it acts on alpha3/beta4 and weakly on alpha3beta2 and alpha6-containing receptors. A full agonism was displayed on alpha7-receptors.

Structure

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

HMDB0015398
     RDKit          3D
Varenicline
 29 32  0  0  0  0  0  0  0  0999 V2000
    4.4015   -0.2967    0.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432   -0.1382   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -0.0834   -1.2301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -0.1863   -0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1602   -0.1305   -1.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1221   -0.2349   -1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2989   -0.3946    0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8025   -0.4479    1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843   -0.3448    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -0.3994    1.4703 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -0.5022    0.6069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4236    0.8228    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202    1.3484   -0.4328 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9855    1.2164   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -0.1995   -1.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2762   -1.0622   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2908   -0.3367    1.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735   -0.0584   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -0.0058   -2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.5741    2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100   -1.2143    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3004    0.6624    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    1.5552    1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8859    1.0999   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608    1.9360   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5128    1.5691   -2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830   -0.5583   -2.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688   -0.9215   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669   -2.1205   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  1  1  0
 16 11  1  0
  9  4  1  0
 15  6  1  0
  1 17  1  0
  2 18  1  0
  5 19  1  0
  8 20  1  0
 11 21  1  1
 12 22  1  0
 12 23  1  0
 13 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  6
 16 28  1  0
 16 29  1  0
M  END

1273
  Mrv0541 02231215222D          

 18 21  0  0  1  0            999 V2000
    7.5417    0.0362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7584   -1.8273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389   -0.4079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6545    0.3520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8513    1.0865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2911    1.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3374   -0.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572    0.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9508   -0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2692    0.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9519   -1.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652    0.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -1.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -0.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9333   -1.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208   -1.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4970   -0.2356    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0088    1.6741    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2 13  2  0  0  0  0
  2 15  1  0  0  0  0
  3 14  2  0  0  0  0
  3 16  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  4 17  1  1  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 18  1  6  0  0  0
  7  8  1  0  0  0  0
  7 11  2  0  0  0  0
  8 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015398

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2/t8-,9+

> <INCHI_KEY>
JQSHBVHOMNKWFT-DTORHVGOSA-N

> <FORMULA>
C13H13N3

> <MOLECULAR_WEIGHT>
211.2624

> <EXACT_MASS>
211.110947431

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.11535472093646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12S)-5,8,14-triazatetracyclo[10.3.1.0²,¹¹.0⁴,⁹]hexadeca-2,4,6,8,10-pentaene

> <ALOGPS_LOGP>
1.39

> <JCHEM_LOGP>
1.0076279959999996

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.726333010947785

> <JCHEM_POLAR_SURFACE_AREA>
37.81

> <JCHEM_REFRACTIVITY>
61.30300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chantix

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015398
     RDKit          3D
Varenicline
 29 32  0  0  0  0  0  0  0  0999 V2000
    4.4015   -0.2967    0.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432   -0.1382   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -0.0834   -1.2301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -0.1863   -0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1602   -0.1305   -1.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1221   -0.2349   -1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2989   -0.3946    0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8025   -0.4479    1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843   -0.3448    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -0.3994    1.4703 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -0.5022    0.6069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4236    0.8228    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202    1.3484   -0.4328 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9855    1.2164   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -0.1995   -1.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2762   -1.0622   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2908   -0.3367    1.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735   -0.0584   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -0.0058   -2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.5741    2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100   -1.2143    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3004    0.6624    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    1.5552    1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8859    1.0999   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608    1.9360   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5128    1.5691   -2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830   -0.5583   -2.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688   -0.9215   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669   -2.1205   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  1  1  0
 16 11  1  0
  9  4  1  0
 15  6  1  0
  1 17  1  0
  2 18  1  0
  5 19  1  0
  8 20  1  0
 11 21  1  1
 12 22  1  0
 12 23  1  0
 13 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  6
 16 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1273                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      14.078   0.068   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       5.149  -3.411   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.619  -0.761   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      10.555   0.657   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.922   2.028   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.877   3.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.096  -0.762   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.387   0.467   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.975  -0.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.569   1.393   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.377  -2.054   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.908   0.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.898  -2.066   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.159  -0.785   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.609  -3.423   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.839  -2.089   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      10.261  -0.440   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      11.216   3.125   0.000  0.00  0.00           H+0
CONECT    1    9   10                                                       
CONECT    2   13   15                                                       
CONECT    3   14   16                                                       
CONECT    4    6    7    9   17                                             
CONECT    5    6    8   10   18                                             
CONECT    6    4    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    5    7   12                                                  
CONECT    9    1    4                                                       
CONECT   10    1    5                                                       
CONECT   11    7   13                                                       
CONECT   12    8   14                                                       
CONECT   13    2   11   14                                                  
CONECT   14    3   12   13                                                  
CONECT   15    2   16                                                       
CONECT   16    3   15                                                       
CONECT   17    4                                                            
CONECT   18    5                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

COMPND    HMDB0015398
HETATM    1  C1  UNL     1       4.401  -0.297   0.962  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.543  -0.138  -0.399  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.489  -0.083  -1.230  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.238  -0.186  -0.725  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.160  -0.130  -1.569  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.122  -0.235  -1.059  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.299  -0.395   0.294  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.802  -0.448   1.128  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.084  -0.345   0.633  1.00  0.00           C  
HETATM   10  N2  UNL     1       3.164  -0.399   1.470  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.773  -0.502   0.607  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.424   0.823   0.796  1.00  0.00           C  
HETATM   13  N3  UNL     1      -2.920   1.348  -0.433  1.00  0.00           N  
HETATM   14  C11 UNL     1      -1.986   1.216  -1.532  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.473  -0.200  -1.666  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.276  -1.062  -0.734  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.291  -0.337   1.607  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.573  -0.058  -0.772  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.243  -0.006  -2.647  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.651  -0.574   2.197  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.910  -1.214   1.425  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.300   0.662   1.488  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.779   1.555   1.337  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.886   1.100  -0.672  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.161   1.936  -1.347  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.513   1.569  -2.442  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.483  -0.558  -2.709  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.369  -0.922  -0.835  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.967  -2.121  -0.750  1.00  0.00           H  
CONECT    1    2    2   10   17
CONECT    2    3   18
CONECT    3    4    4
CONECT    4    5    9
CONECT    5    6    6   19
CONECT    6    7   15
CONECT    7    8    8   11
CONECT    8    9   20
CONECT    9   10   10
CONECT   11   12   16   21
CONECT   12   13   22   23
CONECT   13   14   24
CONECT   14   15   25   26
CONECT   15   16   27
CONECT   16   28   29
END

HMDB0015398
     RDKit          3D
Varenicline
 29 32  0  0  0  0  0  0  0  0999 V2000
    4.4015   -0.2967    0.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5432   -0.1382   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -0.0834   -1.2301 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376   -0.1863   -0.7247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1602   -0.1305   -1.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1221   -0.2349   -1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2989   -0.3946    0.2935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8025   -0.4479    1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843   -0.3448    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -0.3994    1.4703 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7731   -0.5022    0.6069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4236    0.8228    0.7958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202    1.3484   -0.4328 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9855    1.2164   -1.5324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727   -0.1995   -1.6658 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2762   -1.0622   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2908   -0.3367    1.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5735   -0.0584   -0.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2426   -0.0058   -2.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.5741    2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100   -1.2143    1.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3004    0.6624    1.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788    1.5552    1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8859    1.0999   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608    1.9360   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5128    1.5691   -2.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4830   -0.5583   -2.7093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688   -0.9215   -0.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9669   -2.1205   -0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  1  1  0
 16 11  1  0
  9  4  1  0
 15  6  1  0
  1 17  1  0
  2 18  1  0
  5 19  1  0
  8 20  1  0
 11 21  1  1
 12 22  1  0
 12 23  1  0
 13 24  1  0
 14 25  1  0
 14 26  1  0
 15 27  1  6
 16 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,8,9,10-Tetrahydro-6,10-methano-6H-pyrazino(2,3-H)(3)benzazepine	ChEBI
Vareniclina	ChEBI
Vareniclinum	ChEBI
CP-526,555	HMDB
Varenicline tartrate	HMDB
6,7,8,9-Tetrahydro-6,10-methano-6H-pyrazino(2,3-H)benzazepine	HMDB
Tartrate, varenicline	HMDB
Champix	HMDB
Chantix	HMDB

Chemical Formula

C₁₃H₁₃N₃

Average Molecular Weight

211.2624

Monoisotopic Molecular Weight

211.110947431

IUPAC Name

(1R,12S)-5,8,14-triazatetracyclo[10.3.1.0²,¹¹.0⁴,⁹]hexadeca-2,4,6,8,10-pentaene

Traditional Name

chantix

CAS Registry Number

249296-44-4

SMILES

[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C21

InChI Identifier

InChI=1S/C13H13N3/c1-2-16-13-5-11-9-3-8(6-14-7-9)10(11)4-12(13)15-1/h1-2,4-5,8-9,14H,3,6-7H2/t8-,9+

InChI Key

JQSHBVHOMNKWFT-DTORHVGOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Diazanaphthalene
Quinoxaline
Indane
Azepine
Aralkylamine
Piperidine
Benzenoid
Pyrazine
Heteroaromatic compound
Secondary aliphatic amine
Azacycle
Secondary amine
Hydrocarbon derivative
Amine
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:84500 )
secondary amino compound (CHEBI:84500 )
bridged compound (CHEBI:84500 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015398)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.088 g/L	Not Available
LogP	0.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	151.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	1.39	ALOGPS
logP	1.01	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	9.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.81 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	61.3 m³·mol⁻¹	ChemAxon
Polarizability	23.12 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]+	149.845	31661259
DarkChem	[M-H]-	150.963	31661259
DeepCCS	[M-2H]-	183.443	30932474
DeepCCS	[M+Na]+	158.866	30932474
AllCCS	[M+H]+	147.2	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	151.0	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	153.5	32859911
AllCCS	[M+Na-2H]-	153.0	32859911
AllCCS	[M+HCOO]-	152.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.76 minutes	32390414
Predicted by Siyang on May 30, 2022	9.0482 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	189.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	713.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	235.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	110.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	251.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	738.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	575.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	36.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	854.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	159.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	595.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	418.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	183.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Varenicline	[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C21	2961.4	Standard polar	33892256
Varenicline	[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C21	2160.0	Standard non polar	33892256
Varenicline	[H][C@]12C[C@]([H])(CNC1)C1=CC3=NC=CN=C3C=C21	2126.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Varenicline,1TMS,isomer #1	C[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C12	2255.8	Semi standard non polar	33892256
Varenicline,1TMS,isomer #1	C[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C12	2251.5	Standard non polar	33892256
Varenicline,1TMS,isomer #1	C[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C12	2791.8	Standard polar	33892256
Varenicline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C12	2497.2	Semi standard non polar	33892256
Varenicline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C12	2509.9	Standard non polar	33892256
Varenicline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C[C@H]2C[C@@H](C1)C1=CC3=NC=CN=C3C=C12	3013.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Varenicline GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-1910000000-6dbc451aea83e1d014b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Varenicline 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 10V, Positive-QTOF	splash10-03di-0190000000-4f145434c13b3afcb533	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 20V, Positive-QTOF	splash10-03di-0590000000-9e05cfabbf6c1eb096b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 40V, Positive-QTOF	splash10-0159-3900000000-82a1aaedcfa4ad0c47d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 10V, Negative-QTOF	splash10-03di-0090000000-213d1987d097fb210ee1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 20V, Negative-QTOF	splash10-03di-0190000000-c719b55058a71a235995	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 40V, Negative-QTOF	splash10-01po-3930000000-7accc44141f8030a7a2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 10V, Positive-QTOF	splash10-03di-0090000000-151eb25ddf9df2d6bfbe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 20V, Positive-QTOF	splash10-03di-0090000000-151eb25ddf9df2d6bfbe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 40V, Positive-QTOF	splash10-0lz9-0920000000-ff0909b76eb139f2276a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 10V, Negative-QTOF	splash10-03di-0090000000-4dafdcd63f1115768fe9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 20V, Negative-QTOF	splash10-03di-0090000000-4dafdcd63f1115768fe9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Varenicline 40V, Negative-QTOF	splash10-0a4i-0190000000-1ec0bedd3eb5b1bc4034	2021-10-11	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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01273	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01273	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01273

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Varenicline

METLIN ID

Not Available

PubChem Compound

5310966

PDB ID

QMR

ChEBI ID

84500

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

Coe JW, Brooks PR, Vetelino MG, Wirtz MC, Arnold EP, Huang J, Sands SB, Davis TI, Lebel LA, Fox CB, Shrikhande A, Heym JH, Schaeffer E, Rollema H, Lu Y, Mansbach RS, Chambers LK, Rovetti CC, Schulz DW, Tingley FD 3rd, O'Neill BT: Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation. J Med Chem. 2005 May 19;48(10):3474-7. [PubMed:15887955 ]
Obach RS, Reed-Hagen AE, Krueger SS, Obach BJ, O'Connell TN, Zandi KS, Miller S, Coe JW: Metabolism and disposition of varenicline, a selective alpha4beta2 acetylcholine receptor partial agonist, in vivo and in vitro. Drug Metab Dispos. 2006 Jan;34(1):121-30. Epub 2005 Oct 12. [PubMed:16221753 ]
Kuehn BM: FDA speeds smoking cessation drug review. JAMA. 2006 Feb 8;295(6):614. [PubMed:16467225 ]
Mihalak KB, Carroll FI, Luetje CW: Varenicline is a partial agonist at alpha4beta2 and a full agonist at alpha7 neuronal nicotinic receptors. Mol Pharmacol. 2006 Sep;70(3):801-5. Epub 2006 Jun 9. [PubMed:16766716 ]
Jorenby DE, Hays JT, Rigotti NA, Azoulay S, Watsky EJ, Williams KE, Billing CB, Gong J, Reeves KR: Efficacy of varenicline, an alpha4beta2 nicotinic acetylcholine receptor partial agonist, vs placebo or sustained-release bupropion for smoking cessation: a randomized controlled trial. JAMA. 2006 Jul 5;296(1):56-63. [PubMed:16820547 ]

Showing metabocard for Varenicline (HMDB0015398)

MOL for HMDB0015398 (Varenicline)

3D MOL for HMDB0015398 (Varenicline)

3D SDF for HMDB0015398 (Varenicline)

3D-SDF for HMDB0015398 (Varenicline)

PDB for HMDB0015398 (Varenicline)

3D PDB for HMDB0015398 (Varenicline)

SMILES for HMDB0015398 (Varenicline)

INCHI for HMDB0015398 (Varenicline)

Structure for HMDB0015398 (Varenicline)

3D Structure for HMDB0015398 (Varenicline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra