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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015098

Secondary Accession Numbers

HMDB15098

Metabolite Identification

Common Name

Bromfenac

Description

Bromfenac, also known as bromfenac sodium or xibrom, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Bromfenac is a drug which is used for the treatment of postoperative inflammation in patients who have undergone cataract extraction. Amfenac in which the the hydrogen at the 4 position of the benzoyl group is substituted by bromine. Bromfenac is a moderately basic compound (based on its pKa). In humans, bromfenac is involved in bromfenac action pathway. Bromfenac is a potentially toxic compound. It is used for the management of ocular pain and treatment of postoperative inflammation in patients who have undergone cataract extraction. It was withdrawn from the US market in 1998, following concerns over off-label abuse and hepatic failure.

Structure

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

HMDB0015098
     RDKit          3D
Bromfenac
 32 33  0  0  0  0  0  0  0  0999 V2000
    1.3676   -0.1927   -1.7949 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3733   -0.4575   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4974   -0.8959    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209   -1.0770   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123    0.2668   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    0.8684    0.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494    0.7970   -2.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -1.1564    1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329   -0.9500    2.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753   -0.5021    1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -0.2473    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760    0.2377   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029    0.5645   -1.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350    0.4284    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590    1.5147   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645    1.6771   -0.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0063    0.8329    0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8262    1.1465    1.2457 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901   -0.2329    1.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742   -0.4266    0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    0.7593   -2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1313   -0.9051   -2.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056   -1.7732   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713   -1.5444   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0940    1.7715   -2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -1.5083    2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.1443    3.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921   -0.3347    2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    2.1856   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9220    2.5195   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7648   -0.9339    1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318   -1.2878    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  2  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 15 29  1  0
 16 30  1  0
 19 31  1  0
 20 32  1  0
M  END

963
  Mrv0541 02231215082D          

 20 21  0  0  0  0            999 V2000
    1.6500   -1.3654    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7949    0.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.9529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.1096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  2 11  2  0  0  0  0
  3 17  1  0  0  0  0
  4 17  2  0  0  0  0
  5  8  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  2  0  0  0  0
  9 17  1  0  0  0  0
 10 14  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
 13 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015098

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12BrNO3/c16-11-6-4-9(5-7-11)15(20)12-3-1-2-10(14(12)17)8-13(18)19/h1-7H,8,17H2,(H,18,19)

> <INCHI_KEY>
ZBPLOVFIXSTCRZ-UHFFFAOYSA-N

> <FORMULA>
C15H12BrNO3

> <MOLECULAR_WEIGHT>
334.165

> <EXACT_MASS>
333.000055902

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.93101847388133

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
3.660173814

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.40587910205938

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8071339684445986

> <JCHEM_PKA_STRONGEST_BASIC>
1.5886730056386378

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
80.2643

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bromfenac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015098
     RDKit          3D
Bromfenac
 32 33  0  0  0  0  0  0  0  0999 V2000
    1.3676   -0.1927   -1.7949 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3733   -0.4575   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4974   -0.8959    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209   -1.0770   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123    0.2668   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    0.8684    0.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494    0.7970   -2.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -1.1564    1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329   -0.9500    2.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753   -0.5021    1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -0.2473    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760    0.2377   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029    0.5645   -1.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350    0.4284    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590    1.5147   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645    1.6771   -0.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0063    0.8329    0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8262    1.1465    1.2457 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901   -0.2329    1.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742   -0.4266    0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    0.7593   -2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1313   -0.9051   -2.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056   -1.7732   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713   -1.5444   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0940    1.7715   -2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -1.5083    2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.1443    3.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921   -0.3347    2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    2.1856   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9220    2.5195   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7648   -0.9339    1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318   -1.2878    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  2  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 15 29  1  0
 16 30  1  0
 19 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 963                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Br   UNK     0       3.080  -2.549   0.000  0.00  0.00          Br+0
HETATM    2  O   UNK     0       8.415   2.071   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      16.417   0.531   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.083  -1.779   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.082   2.071   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      12.416  -0.239   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748  -0.239   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   0.531   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.750   0.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.416  -1.779   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   0.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748  -1.779   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -0.239   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082  -2.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -1.779   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   0.531   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.083  -0.239   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -0.239   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -1.779   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   11                                                            
CONECT    3   17                                                            
CONECT    4   17                                                            
CONECT    5    8                                                            
CONECT    6    8    9   10                                                  
CONECT    7    8   11   12                                                  
CONECT    8    5    6    7                                                  
CONECT    9    6   17                                                       
CONECT   10    6   14                                                       
CONECT   11    2    7   13                                                  
CONECT   12    7   14                                                       
CONECT   13   11   15   16                                                  
CONECT   14   10   12                                                       
CONECT   15   13   18                                                       
CONECT   16   13   19                                                       
CONECT   17    3    4    9                                                  
CONECT   18   15   20                                                       
CONECT   19   16   20                                                       
CONECT   20    1   18   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0015098
HETATM    1  N1  UNL     1       1.368  -0.193  -1.795  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.373  -0.458  -0.405  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.497  -0.896   0.232  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.721  -1.077  -0.621  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.312   0.267  -0.834  1.00  0.00           C  
HETATM    6  O1  UNL     1       4.758   0.868   0.189  1.00  0.00           O  
HETATM    7  O2  UNL     1       4.349   0.797  -2.105  1.00  0.00           O  
HETATM    8  C5  UNL     1       2.526  -1.156   1.561  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.333  -0.950   2.255  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.175  -0.502   1.625  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.165  -0.247   0.287  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.976   0.238  -0.426  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.803   0.564  -1.670  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.335   0.428   0.029  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.059   1.515  -0.498  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.365   1.677  -0.111  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.006   0.833   0.767  1.00  0.00           C  
HETATM   18 BR1  UNL     1      -6.826   1.146   1.246  1.00  0.00          BR  
HETATM   19  C14 UNL     1      -4.290  -0.233   1.282  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.974  -0.427   0.913  1.00  0.00           C  
HETATM   21  H1  UNL     1       1.607   0.759  -2.125  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.131  -0.905  -2.507  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.406  -1.773  -0.089  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.471  -1.544  -1.594  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.094   1.772  -2.286  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.421  -1.508   2.075  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.297  -1.144   3.321  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.692  -0.335   2.230  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.560   2.186  -1.190  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.922   2.520  -0.516  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.765  -0.934   1.991  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.432  -1.288   1.295  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3    3   11
CONECT    3    4    8
CONECT    4    5   23   24
CONECT    5    6    6    7
CONECT    7   25
CONECT    8    9    9   26
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   20
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   18   19
CONECT   19   20   20   31
CONECT   20   32
END

HMDB0015098
     RDKit          3D
Bromfenac
 32 33  0  0  0  0  0  0  0  0999 V2000
    1.3676   -0.1927   -1.7949 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3733   -0.4575   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4974   -0.8959    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209   -1.0770   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3123    0.2668   -0.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    0.8684    0.1887 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494    0.7970   -2.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5257   -1.1564    1.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329   -0.9500    2.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1753   -0.5021    1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647   -0.2473    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760    0.2377   -0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8029    0.5645   -1.6702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3350    0.4284    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590    1.5147   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3645    1.6771   -0.1109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0063    0.8329    0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8262    1.1465    1.2457 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2901   -0.2329    1.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742   -0.4266    0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067    0.7593   -2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1313   -0.9051   -2.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056   -1.7732   -0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4713   -1.5444   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0940    1.7715   -2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -1.5083    2.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2973   -1.1443    3.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921   -0.3347    2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    2.1856   -1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9220    2.5195   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7648   -0.9339    1.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4318   -1.2878    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  3  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 11  2  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 15 29  1  0
 16 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-3-(4-bromobenzoyl)benzeneacetic acid	ChEBI
[2-Amino-3-(4-bromo-benzoyl)-phenyl]-acetic acid	ChEBI
Bromfenaco	ChEBI
Bromfenacum	ChEBI
2-Amino-3-(4-bromobenzoyl)benzeneacetate	Generator
[2-Amino-3-(4-bromo-benzoyl)-phenyl]-acetate	Generator
Bromfenac sodium	HMDB
Xibrom	HMDB
Sodium bromfenac	HMDB
Wyeth brand OF sodium bromfenac	HMDB
Duract	HMDB
ISV-303	HMDB

Chemical Formula

C₁₅H₁₂BrNO₃

Average Molecular Weight

334.165

Monoisotopic Molecular Weight

333.000055902

IUPAC Name

2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid

Traditional Name

bromfenac

CAS Registry Number

91714-94-2

SMILES

NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1

InChI Identifier

InChI=1S/C15H12BrNO3/c16-11-6-4-9(5-7-11)15(20)12-3-1-2-10(14(12)17)8-13(18)19/h1-7H,8,17H2,(H,18,19)

InChI Key

ZBPLOVFIXSTCRZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Diphenylmethane
Aryl-phenylketone
Benzoyl
Aryl ketone
Aniline or substituted anilines
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Vinylogous amide
Amino acid
Amino acid or derivatives
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organohalogen compound
Organopnictogen compound
Organobromide
Organonitrogen compound
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Primary amine
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organobromine compound (CHEBI:240107 )
benzophenones (CHEBI:240107 )
substituted aniline (CHEBI:240107 )
aromatic amino acid (CHEBI:240107 )

Ontology

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	0.013 g/L	Not Available
LogP	3.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3	ALOGPS
logP	3.66	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	1.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	80.39 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.26 m³·mol⁻¹	ChemAxon
Polarizability	29.93 Å³	ChemAxon
Number of Rings	2	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]+	167.006	30932474
DeepCCS	[M-H]-	164.648	30932474
DeepCCS	[M-2H]-	197.534	30932474
DeepCCS	[M+Na]+	173.099	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	168.2	32859911
AllCCS	[M+NH4]+	174.7	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	166.1	32859911
AllCCS	[M+Na-2H]-	166.1	32859911
AllCCS	[M+HCOO]-	166.2	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.	6.43 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5592 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2007.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	383.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	218.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	144.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	533.3 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	648.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1115.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	466.9 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	1411.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	441.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	162.8 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	81.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bromfenac	NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1	4468.6	Standard polar	33892256
Bromfenac	NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1	2653.6	Standard non polar	33892256
Bromfenac	NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1	2737.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bromfenac,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N	2657.2	Semi standard non polar	33892256
Bromfenac,1TMS,isomer #2	C[Si](C)(C)NC1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1	2769.8	Semi standard non polar	33892256
Bromfenac,2TMS,isomer #1	C[Si](C)(C)NC1=C(CC(=O)O[Si](C)(C)C)C=CC=C1C(=O)C1=CC=C(Br)C=C1	2709.0	Semi standard non polar	33892256
Bromfenac,2TMS,isomer #1	C[Si](C)(C)NC1=C(CC(=O)O[Si](C)(C)C)C=CC=C1C(=O)C1=CC=C(Br)C=C1	2616.5	Standard non polar	33892256
Bromfenac,2TMS,isomer #1	C[Si](C)(C)NC1=C(CC(=O)O[Si](C)(C)C)C=CC=C1C(=O)C1=CC=C(Br)C=C1	3192.8	Standard polar	33892256
Bromfenac,2TMS,isomer #2	C[Si](C)(C)N(C1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1)[Si](C)(C)C	2698.8	Semi standard non polar	33892256
Bromfenac,2TMS,isomer #2	C[Si](C)(C)N(C1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1)[Si](C)(C)C	2620.6	Standard non polar	33892256
Bromfenac,2TMS,isomer #2	C[Si](C)(C)N(C1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1)[Si](C)(C)C	3220.0	Standard polar	33892256
Bromfenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N([Si](C)(C)C)[Si](C)(C)C	2683.5	Semi standard non polar	33892256
Bromfenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N([Si](C)(C)C)[Si](C)(C)C	2633.3	Standard non polar	33892256
Bromfenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N([Si](C)(C)C)[Si](C)(C)C	2948.1	Standard polar	33892256
Bromfenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N	2915.7	Semi standard non polar	33892256
Bromfenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1	3000.8	Semi standard non polar	33892256
Bromfenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)C1=CC=C(Br)C=C1	3145.4	Semi standard non polar	33892256
Bromfenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)C1=CC=C(Br)C=C1	3055.7	Standard non polar	33892256
Bromfenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(CC(=O)O[Si](C)(C)C(C)(C)C)C=CC=C1C(=O)C1=CC=C(Br)C=C1	3359.3	Standard polar	33892256
Bromfenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1)[Si](C)(C)C(C)(C)C	3157.4	Semi standard non polar	33892256
Bromfenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1)[Si](C)(C)C(C)(C)C	3002.3	Standard non polar	33892256
Bromfenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=C(CC(=O)O)C=CC=C1C(=O)C1=CC=C(Br)C=C1)[Si](C)(C)C(C)(C)C	3334.2	Standard polar	33892256
Bromfenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3325.5	Semi standard non polar	33892256
Bromfenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3201.7	Standard non polar	33892256
Bromfenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC(C(=O)C2=CC=C(Br)C=C2)=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3215.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bromfenac GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2942000000-55d5af00fe6fa398bead	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromfenac GC-MS (1 TMS) - 70eV, Positive	splash10-000i-5391000000-a985cfcf083f34c1b155	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromfenac 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 - Bromfenac 10V, Positive-QTOF	splash10-00lr-0039000000-8bc362a4cdf601ba45d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 20V, Positive-QTOF	splash10-000i-0292000000-5eada8c7771779cb0353	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 40V, Positive-QTOF	splash10-0540-2950000000-5f5aed8a6d28056c567a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 10V, Negative-QTOF	splash10-001r-0059000000-17d7c340ec08a0adaba2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 20V, Negative-QTOF	splash10-001r-1298000000-1d237d5738d709e7bf6d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 40V, Negative-QTOF	splash10-0zgi-3892000000-27126ed6eaa7f4fe957e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 10V, Positive-QTOF	splash10-00lr-0029000000-f6ac38419ec90ea82b48	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 20V, Positive-QTOF	splash10-001i-0922000000-65ab9952df50df9d5a8a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 40V, Positive-QTOF	splash10-001i-0920000000-17efdd1a42d366c24941	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 10V, Negative-QTOF	splash10-000i-0090000000-44cbc50fb0fa3719a78c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 20V, Negative-QTOF	splash10-000i-1190000000-61dfc1dbf6f576473d58	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromfenac 40V, Negative-QTOF	splash10-003i-4091000000-4388b82a5f2e1d637fdd	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Bromfenac Action Pathway		Not Available

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 DB00963	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00963	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00963

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54730

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bromfenac

METLIN ID

Not Available

PubChem Compound

60726

PDB ID

Not Available

ChEBI ID

240107

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Waterbury LD, Silliman D, Jolas T: Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40. [PubMed:16846546 ]
Sanchez-Matienzo D, Arana A, Castellsague J, Perez-Gutthann S: Hepatic disorders in patients treated with COX-2 selective inhibitors or nonselective NSAIDs: a case/noncase analysis of spontaneous reports. Clin Ther. 2006 Aug;28(8):1123-32. [PubMed:16982289 ]
Chitturi S, George J: Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs. Semin Liver Dis. 2002;22(2):169-83. [PubMed:12016548 ]
Cho H, Wolf KJ, Wolf EJ: Management of ocular inflammation and pain following cataract surgery: focus on bromfenac ophthalmic solution. Clin Ophthalmol. 2009;3:199-210. Epub 2009 Jun 2. [PubMed:19668566 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Waterbury LD, Silliman D, Jolas T: Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40. [PubMed:16846546 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Bromfenac (HMDB0015098)

MOL for HMDB0015098 (Bromfenac)

3D MOL for HMDB0015098 (Bromfenac)

3D SDF for HMDB0015098 (Bromfenac)

3D-SDF for HMDB0015098 (Bromfenac)

PDB for HMDB0015098 (Bromfenac)

3D PDB for HMDB0015098 (Bromfenac)

SMILES for HMDB0015098 (Bromfenac)

INCHI for HMDB0015098 (Bromfenac)

Structure for HMDB0015098 (Bromfenac)

3D Structure for HMDB0015098 (Bromfenac)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References