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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:28:19 UTC

Update Date

2021-09-26 22:55:32 UTC

HMDB ID

HMDB0246453

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone

Description

1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone, also known as 4-hydroxy bupropion, 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. Based on a literature review very few articles have been published on 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1-(3-chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0246453
     RDKit          3D
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone
 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.2726   -0.0920   -1.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001   -0.0113    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5575    0.6257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342   -0.0530    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566    1.3831    0.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8548   -0.8341    1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3423   -0.0802   -1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7748   -0.7067    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958   -1.6955    1.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521   -0.3296    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2034   -1.0542    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262   -0.7391    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442    0.3510   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753    0.7110   -0.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135    1.0803   -0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289    2.4663   -1.5737 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4893    0.7577   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.5554   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044    0.9091   -1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368   -0.7550   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955    1.0589    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946   -1.3672    1.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9811    1.7223    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    1.4112    1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    2.0649    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8532   -0.7960    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885   -0.4197    2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5215   -1.8867    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    0.6627   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    0.1648   -1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381   -1.1300   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262   -1.9345    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3325   -1.3237    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9474    0.2062    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    1.3720   -0.8046 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
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
M  END

  Mrv1652309112101282D          

 17 17  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  7 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246453

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18ClNO2/c1-8(15-13(2,3)4)12(17)9-5-6-11(16)10(14)7-9/h5-8,15-16H,1-4H3

> <INCHI_KEY>
LSZBTGUSYVNVLH-UHFFFAOYSA-N

> <FORMULA>
C13H18ClNO2

> <MOLECULAR_WEIGHT>
255.74

> <EXACT_MASS>
255.1026065

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.155694086863548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(tert-butylamino)-1-(3-chloro-4-hydroxyphenyl)propan-1-one

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
1.879909077759657

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.898650594759406

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.11584374079288

> <JCHEM_PKA_STRONGEST_BASIC>
8.320375288023534

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
69.6803

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(tert-butylamino)-1-(3-chloro-4-hydroxyphenyl)propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246453
     RDKit          3D
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone
 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.2726   -0.0920   -1.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001   -0.0113    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5575    0.6257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342   -0.0530    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566    1.3831    0.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8548   -0.8341    1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3423   -0.0802   -1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7748   -0.7067    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958   -1.6955    1.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521   -0.3296    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2034   -1.0542    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262   -0.7391    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442    0.3510   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753    0.7110   -0.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135    1.0803   -0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289    2.4663   -1.5737 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4893    0.7577   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.5554   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044    0.9091   -1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368   -0.7550   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955    1.0589    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946   -1.3672    1.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9811    1.7223    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    1.4112    1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    2.0649    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8532   -0.7960    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885   -0.4197    2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5215   -1.8867    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    0.6627   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    0.1648   -1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381   -1.1300   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262   -1.9345    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3325   -1.3237    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9474    0.2062    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    1.3720   -0.8046 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
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   12 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM   13  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.564   8.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.104   5.596   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8                                                            
CONECT   12    7                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0246453
HETATM    1  C1  UNL     1      -0.273  -0.092  -1.396  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.400  -0.011   0.110  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.577  -0.558   0.626  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.834  -0.053   0.342  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.957   1.383   0.857  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.855  -0.834   1.194  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.342  -0.080  -1.057  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.775  -0.707   0.694  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.596  -1.696   1.482  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.152  -0.330   0.423  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.203  -1.054   0.961  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.526  -0.739   0.751  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.844   0.351  -0.034  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.175   0.711  -0.277  1.00  0.00           O  
HETATM   15  C12 UNL     1       3.814   1.080  -0.576  1.00  0.00           C  
HETATM   16 CL1  UNL     1       4.229   2.466  -1.574  1.00  0.00          CL  
HETATM   17  C13 UNL     1       2.489   0.758  -0.359  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.710  -0.555  -1.665  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.404   0.909  -1.807  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.037  -0.755  -1.858  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.296   1.059   0.434  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.495  -1.367   1.261  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.981   1.722   0.579  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.876   1.411   1.944  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.250   2.065   0.339  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.853  -0.796   0.727  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.889  -0.420   2.224  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.521  -1.887   1.204  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.933   0.663  -1.741  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.452   0.165  -1.015  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.338  -1.130  -1.431  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.026  -1.935   1.596  1.00  0.00           H  
HETATM   33  H16 UNL     1       5.332  -1.324   1.185  1.00  0.00           H  
HETATM   34  H17 UNL     1       6.947   0.206   0.099  1.00  0.00           H  
HETATM   35  H18 UNL     1       1.743   1.372  -0.805  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    8   21
CONECT    3    4   22
CONECT    4    5    6    7
CONECT    5   23   24   25
CONECT    6   26   27   28
CONECT    7   29   30   31
CONECT    8    9    9   10
CONECT   10   11   11   17
CONECT   11   12   32
CONECT   12   13   13   33
CONECT   13   14   15
CONECT   14   34
CONECT   15   16   17   17
CONECT   17   35
END

HMDB0246453
     RDKit          3D
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone
 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.2726   -0.0920   -1.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4001   -0.0113    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5765   -0.5575    0.6257 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342   -0.0530    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566    1.3831    0.8573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8548   -0.8341    1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3423   -0.0802   -1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7748   -0.7067    0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958   -1.6955    1.4824 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1521   -0.3296    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2034   -1.0542    0.9614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5262   -0.7391    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442    0.3510   -0.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1753    0.7110   -0.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135    1.0803   -0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2289    2.4663   -1.5737 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4893    0.7577   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7095   -0.5554   -1.6652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4044    0.9091   -1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368   -0.7550   -1.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2955    1.0589    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946   -1.3672    1.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9811    1.7223    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    1.4112    1.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2501    2.0649    0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8532   -0.7960    0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885   -0.4197    2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5215   -1.8867    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    0.6627   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4521    0.1648   -1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381   -1.1300   -1.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262   -1.9345    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3325   -1.3237    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9474    0.2062    0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7430    1.3720   -0.8046 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
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy bupropion	HMDB
Hydroxybupropion	HMDB

Chemical Formula

C₁₃H₁₈ClNO₂

Average Molecular Weight

255.74

Monoisotopic Molecular Weight

255.1026065

IUPAC Name

2-(tert-butylamino)-1-(3-chloro-4-hydroxyphenyl)propan-1-one

Traditional Name

2-(tert-butylamino)-1-(3-chloro-4-hydroxyphenyl)propan-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H18ClNO2/c1-8(15-13(2,3)4)12(17)9-5-6-11(16)10(14)7-9/h5-8,15-16H,1-4H3

InChI Key

LSZBTGUSYVNVLH-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
2-halophenol
2-chlorophenol
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Phenol
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Alpha-aminoketone
Secondary amine
Secondary aliphatic amine
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	2.93	ALOGPS
logP	1.88	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.12	ChemAxon
pKa (Strongest Basic)	8.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.68 m³·mol⁻¹	ChemAxon
Polarizability	27.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	163.912	30932474
DeepCCS	[M-H]-	161.554	30932474
DeepCCS	[M-2H]-	194.44	30932474
DeepCCS	[M+Na]+	170.005	30932474
AllCCS	[M+H]+	156.5	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.4	32859911
AllCCS	[M-H]-	159.6	32859911
AllCCS	[M+Na-2H]-	160.2	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone	CC(NC(C)(C)C)C(=O)C1=CC(Cl)=C(O)C=C1	2659.5	Standard polar	33892256
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone	CC(NC(C)(C)C)C(=O)C1=CC(Cl)=C(O)C=C1	1860.2	Standard non polar	33892256
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone	CC(NC(C)(C)C)C(=O)C1=CC(Cl)=C(O)C=C1	1820.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone,2TMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C)C(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C	2084.9	Semi standard non polar	33892256
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone,2TMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C)C(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C	2142.3	Standard non polar	33892256
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone,2TMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C)C(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C	2145.7	Standard polar	33892256
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone,2TBDMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C(C)(C)C	2613.5	Semi standard non polar	33892256
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone,2TBDMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C(C)(C)C	2602.8	Standard non polar	33892256
1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone,2TBDMS,isomer #1	CC(C(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(Cl)=C1)N(C(C)(C)C)[Si](C)(C)C(C)(C)C	2367.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-5900000000-fe3876fc9447144b5451	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone 10V, Positive-QTOF	splash10-0udi-0190000000-63e7a5b6c36de52c09e2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone 20V, Positive-QTOF	splash10-001i-0910000000-35a3c993b7744138edfb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone 40V, Positive-QTOF	splash10-0a4i-9300000000-e3c48d37b6dc3e16f2a8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone 10V, Negative-QTOF	splash10-0udi-0090000000-04c26f716885b28d861f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone 20V, Negative-QTOF	splash10-0udi-1390000000-16923bbdb6a351406378	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone 40V, Negative-QTOF	splash10-001i-9400000000-ff3f9042f8b68351dc6c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64879941

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75304411

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone (HMDB0246453)

MOL for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

3D MOL for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

3D SDF for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

3D-SDF for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

PDB for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

3D PDB for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

SMILES for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

INCHI for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

Structure for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

3D Structure for HMDB0246453 (1-(3-Chloro-4-hydroxyphenyl)-2-((1,1-dimethylethyl)amino)-1-propanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra