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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001510

Secondary Accession Numbers

HMDB01510

Metabolite Identification

Common Name

Bupropion

Description

Bupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4- nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction. A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment; Bupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4-nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction. Bupropion (amfebutamone) (brand names Wellbutrin and Zyban) is an antidepressant of the aminoketone class, chemically unrelated to tricyclics or selective serotonin reuptake inhibitors (SSRIs). It is similar in structure to the stimulant cathinone, and to phenethylamines in general. It is a chemical derivative of diethylpropion, an amphetamine-like substance used as an anorectic. Bupropion is both a dopamine reuptake inhibitor and a norepinephrine reuptake inhibitor. It is often used as a smoking cessation aid.

Structure

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

HMDB0001510
     RDKit          3D
Bupropion
 34 34  0  0  0  0  0  0  0  0999 V2000
    0.2089   -1.0374    1.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509   -0.0224    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.3444   -0.6821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878   -0.5815   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -1.7109    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0875    0.7130    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268   -0.7765   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8008    0.7619   -0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667    1.7334   -1.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427    0.6863   -0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -0.3708    0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3601   -0.2959    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8642   -0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3041    1.9622   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0740    3.4865   -0.9033 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9442    1.8646   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941   -0.6788    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.2140    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4278   -2.0008    0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414    0.7806    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3477    0.4354   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103   -2.4943    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712   -2.2145    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405   -1.3425    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618    0.6877    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.5896    0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1884    0.7165    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956   -1.2278   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    0.2155   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -1.3554   -2.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174   -1.3398    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9243   -1.1834    0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1091    0.9697   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678    2.7242   -0.9742 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
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 16 34  1  0
M  END

1156
  Mrv0541 02231215172D          

 16 16  0  0  1  0            999 V2000
    1.6500   -2.4198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    0.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001510

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3

> <INCHI_KEY>
SNPPWIUOZRMYNY-UHFFFAOYSA-N

> <FORMULA>
C13H18ClNO

> <MOLECULAR_WEIGHT>
239.741

> <EXACT_MASS>
239.10769191

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.925829770522174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.2661124519999998

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.28641838207084

> <JCHEM_PKA_STRONGEST_BASIC>
8.215779524538618

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
67.69940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bupropion

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001510
     RDKit          3D
Bupropion
 34 34  0  0  0  0  0  0  0  0999 V2000
    0.2089   -1.0374    1.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509   -0.0224    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.3444   -0.6821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878   -0.5815   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -1.7109    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0875    0.7130    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268   -0.7765   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8008    0.7619   -0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667    1.7334   -1.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427    0.6863   -0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -0.3708    0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3601   -0.2959    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8642   -0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3041    1.9622   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0740    3.4865   -0.9033 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9442    1.8646   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941   -0.6788    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.2140    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4278   -2.0008    0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414    0.7806    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3477    0.4354   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103   -2.4943    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712   -2.2145    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405   -1.3425    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618    0.6877    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.5896    0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1884    0.7165    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956   -1.2278   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    0.2155   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -1.3554   -2.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174   -1.3398    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9243   -1.1834    0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1091    0.9697   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678    2.7242   -0.9742 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
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1156                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -4.517   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.414   0.873   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.081   2.413   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415   3.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   0.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.748   3.953   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.645   4.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.185   1.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   0.103   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   0.103   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -1.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -2.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -2.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -3.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -3.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -4.517   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6    7    8                                             
CONECT    5    3    9   10                                                  
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    2    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11   15                                                       
CONECT   14    1   12   16                                                  
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0001510
HETATM    1  C1  UNL     1       0.209  -1.037   1.198  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.251  -0.022   0.241  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.284  -0.344  -0.682  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.588  -0.582  -0.174  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.788  -1.711   0.753  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.087   0.713   0.515  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.527  -0.777  -1.378  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.801   0.762  -0.405  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.367   1.733  -1.195  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.243   0.686  -0.340  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.992  -0.371   0.077  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.360  -0.296   0.205  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.029   0.864  -0.089  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.304   1.962  -0.519  1.00  0.00           C  
HETATM   15 CL1  UNL     1       5.074   3.486  -0.903  1.00  0.00          CL  
HETATM   16  C13 UNL     1       2.944   1.865  -0.640  1.00  0.00           C  
HETATM   17  H1  UNL     1       1.094  -0.679   1.760  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.538  -1.214   2.041  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.428  -2.001   0.705  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.841   0.781   0.923  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.348   0.435  -1.371  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.010  -2.494   0.583  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.771  -2.215   0.531  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.841  -1.342   1.804  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.762   0.688   1.567  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.592   1.590   0.020  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.188   0.716   0.409  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.496  -1.228  -1.057  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.802   0.216  -1.815  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.049  -1.355  -2.191  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.517  -1.340   0.274  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.924  -1.183   0.557  1.00  0.00           H  
HETATM   33  H17 UNL     1       6.109   0.970  -0.011  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.368   2.724  -0.974  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    8   20
CONECT    3    4   21
CONECT    4    5    6    7
CONECT    5   22   23   24
CONECT    6   25   26   27
CONECT    7   28   29   30
CONECT    8    9    9   10
CONECT   10   11   11   16
CONECT   11   12   31
CONECT   12   13   13   32
CONECT   13   14   33
CONECT   14   15   16   16
CONECT   16   34
END

HMDB0001510
     RDKit          3D
Bupropion
 34 34  0  0  0  0  0  0  0  0999 V2000
    0.2089   -1.0374    1.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2509   -0.0224    0.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.3444   -0.6821 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5878   -0.5815   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -1.7109    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0875    0.7130    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5268   -0.7765   -1.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8008    0.7619   -0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667    1.7334   -1.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2427    0.6863   -0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -0.3708    0.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3601   -0.2959    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8642   -0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3041    1.9622   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0740    3.4865   -0.9033 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9442    1.8646   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0941   -0.6788    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5377   -1.2140    2.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4278   -2.0008    0.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414    0.7806    0.9233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3477    0.4354   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0103   -2.4943    0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712   -2.2145    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405   -1.3425    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7618    0.6877    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916    1.5896    0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1884    0.7165    0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956   -1.2278   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    0.2155   -1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -1.3554   -2.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174   -1.3398    0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9243   -1.1834    0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1091    0.9697   -0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3678    2.7242   -0.9742 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
  4  6  1  0
  4  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Bupropion	HMDB
Amfebutamona	HMDB
Amfebutamone	HMDB, MeSH
Amfebutamonum	HMDB
Wellbatrin	HMDB
Wellbutrin	HMDB, MeSH
Zyban	HMDB
Bupropion hydrochloride	MeSH, HMDB
Bupropion, (+-)-isomer	MeSH, HMDB
glaxo Wellcome brand 1 OF bupropion hydrochloride	MeSH, HMDB
glaxo Wellcome brand 3 OF bupropion hydrochloride	MeSH, HMDB
Zyban (anti-smoking)	MeSH, HMDB
GlaxoSmithKline brand 2 OF bupropion hydrochloride	MeSH, HMDB
(+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone	MeSH, HMDB
Esteve brand OF bupropion hydrochloride	MeSH, HMDB
glaxo Wellcome brand 2 OF bupropion hydrochloride	MeSH, HMDB
Bupropion hydrochloride, (+-)-isomer	MeSH, HMDB
GlaxoSmithKline brand 1 OF bupropion hydrochloride	MeSH, HMDB
Quomen	MeSH, HMDB
Zyntabac	MeSH, HMDB
Zyban (bupropion)	MeSH, HMDB

Chemical Formula

C₁₃H₁₈ClNO

Average Molecular Weight

239.741

Monoisotopic Molecular Weight

239.10769191

IUPAC Name

2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one

Traditional Name

bupropion

CAS Registry Number

34841-39-9

SMILES

CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1

InChI Identifier

InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3

InChI Key

SNPPWIUOZRMYNY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Phenylpropane
Benzoyl
Aryl alkyl ketone
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Alpha-aminoketone
Secondary aliphatic amine
Secondary amine
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:3219 )
monochlorobenzenes (CHEBI:3219 )
propanone (CHEBI:3219 )
aromatic ketone (CHEBI:3219 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Cardiac disorder

Cardiac arrest (HMDB: HMDB0001510)

Observation

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0001510)
Cell membrane (HMDB: HMDB0001510)

Organ

Brain (HMDB: HMDB0001510)
Liver (HMDB: HMDB0001510)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001510)

Source

Exogenous

Exogenous (HMDB: HMDB0001510)

Food

Food (HMDB: HMDB0001510)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Environmental

Wastewater (HMDB: HMDB0001510)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0001510)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001510)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0001510)
Antidepressant (HMDB: HMDB0001510)

Environmental role

Environmental contaminant (HMDB: HMDB0001510)

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	157.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	3.28	ALOGPS
logP	3.27	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	18.29	ChemAxon
pKa (Strongest Basic)	8.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.7 m³·mol⁻¹	ChemAxon
Polarizability	25.93 Å³	ChemAxon
Number of Rings	1	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]+	152.155	32859911
AllCCS	[M-H]-	156.947	32859911
DeepCCS	[M+H]+	156.413	30932474
DeepCCS	[M-H]-	154.055	30932474
DeepCCS	[M-2H]-	187.076	30932474
DeepCCS	[M+Na]+	162.506	30932474
AllCCS	[M+H]+	152.2	32859911
AllCCS	[M+H-H2O]+	148.5	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	156.9	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bupropion	CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1	2201.2	Standard polar	33892256
Bupropion	CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1	1719.9	Standard non polar	33892256
Bupropion	CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1	1625.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bupropion,1TMS,isomer #1	CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C	1772.4	Semi standard non polar	33892256
Bupropion,1TMS,isomer #1	CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C	1901.8	Standard non polar	33892256
Bupropion,1TMS,isomer #1	CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C	2096.9	Standard polar	33892256
Bupropion,1TBDMS,isomer #1	CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C(C)(C)C	2071.3	Semi standard non polar	33892256
Bupropion,1TBDMS,isomer #1	CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C(C)(C)C	2114.9	Standard non polar	33892256
Bupropion,1TBDMS,isomer #1	CC(C(=O)C1=CC=CC(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C(C)(C)C	2176.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bupropion GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-5900000000-1b5fb2e947791614a61d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bupropion GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bupropion 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 - Bupropion LC-ESI-qTof , Positive-QTOF	splash10-001i-0910000000-fa2592b7296c7561333c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-c10af1c8e3619fe0bffc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-0006-0490000000-55448af4d9a8ce866a88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-2883ba18321a8b8228a1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-0159-0900000000-7d6cad849706146ddab3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-0159-0900000000-0fca8999746b69ee4fc1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-b64f8d2b50bede574f63	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-2edefa63d5f6f1b08db7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-0006-0490000000-b8ea1de058a84547700d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0910000000-6f471b9150fb1b7f6fcc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-0159-0900000000-cc966137ee3283828af7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-00lr-0900000000-7f86f38f740aa41b244b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-e7f2cfdbabbd35a9b643	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-4daf0e10db1e5f2750bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-f77a450be176593153d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion , positive-QTOF	splash10-00m0-0910000000-d2eb7265b058766459c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion , positive-QTOF	splash10-001i-0910000000-fa2592b7296c7561333c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-4d831e97d7e7dfff141b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupropion 60V, Positive-QTOF	splash10-00lr-0900000000-65c6a707c92719eb037b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupropion 10V, Positive-QTOF	splash10-0006-0290000000-f40e79f27fd0f3448f9a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupropion 20V, Positive-QTOF	splash10-000x-2950000000-e144eddb8d64cdf24711	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupropion 40V, Positive-QTOF	splash10-0596-9500000000-9c44a89baee334f5ce9c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupropion 10V, Negative-QTOF	splash10-000i-0090000000-f90eefcb5d4049067bbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupropion 20V, Negative-QTOF	splash10-000i-2490000000-afd91ae0bad53e4c5c9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupropion 40V, Negative-QTOF	splash10-02mi-6930000000-94751c5f94b6dd91d63e	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Brain
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

431

KEGG Compound ID

C06860

BioCyc ID

CPD-3481

BiGG ID

Not Available

Wikipedia Link

Bupropion

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

3219

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Xia, Min; Xu, Bao-feng. Study on synthesis of the amfebutamone hydrochloride. Shandong Huagong (2003), 32(3), 3-5.

Material Safety Data Sheet (MSDS)

Not Available

General References

Mooney ME, Sofuoglu M: Bupropion for the treatment of nicotine withdrawal and craving. Expert Rev Neurother. 2006 Jul;6(7):965-81. [PubMed:16831112 ]
Hesse LM, Sakai Y, Vishnuvardhan D, Li AP, von Moltke LL, Greenblatt DJ: Effect of bupropion on CYP2B6 and CYP3A4 catalytic activity, immunoreactive protein and mRNA levels in primary human hepatocytes: comparison with rifampicin. J Pharm Pharmacol. 2003 Sep;55(9):1229-39. [PubMed:14604466 ]
Goodnick PJ: Pharmacokinetic optimisation of therapy with newer antidepressants. Clin Pharmacokinet. 1994 Oct;27(4):307-30. [PubMed:7834966 ]
Inoue T, Kitaichi Y, Koyama T: [Treatment strategy of refractory depression and its presynaptic mechanism of action]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2003 Feb;23(1):11-20. [PubMed:12690637 ]
Hu KQ, Tiyyagura L, Kanel G, Redeker AG: Acute hepatitis induced by bupropion. Dig Dis Sci. 2000 Sep;45(9):1872-3. [PubMed:11052334 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

3. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

Enzyme Details

4. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

Showing metabocard for Bupropion (HMDB0001510)

MOL for HMDB0001510 (Bupropion)

3D MOL for HMDB0001510 (Bupropion)

3D SDF for HMDB0001510 (Bupropion)

3D-SDF for HMDB0001510 (Bupropion)

PDB for HMDB0001510 (Bupropion)

3D PDB for HMDB0001510 (Bupropion)

SMILES for HMDB0001510 (Bupropion)

INCHI for HMDB0001510 (Bupropion)

Structure for HMDB0001510 (Bupropion)

3D Structure for HMDB0001510 (Bupropion)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Transporters