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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015403

Secondary Accession Numbers

HMDB15403

Metabolite Identification

Common Name

Lumiracoxib

Description

Lumiracoxib, also known as COX 189 or prexige, belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group. Lumiracoxib is a drug which is used for the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults. Lumiracoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, lumiracoxib is involved in lumiracoxib action pathway.

Structure

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

HMDB0015403
     RDKit          3D
Lumiracoxib
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.6717   -2.4744   -0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -1.6651   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504   -1.9993   -0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -1.2372   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -0.1465    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    0.6130    0.8291 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    0.3501    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738   -0.4863    1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -1.0824    2.3601 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1755   -0.7365    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6767   -0.1552   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965    0.6856   -1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5896    0.9331   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    1.9960   -1.7093 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6353    0.1789    0.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    1.3558    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.6035    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    2.5612   -0.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    3.8466    1.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7312   -0.5873    0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921   -2.6168   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5795   -3.4796   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222   -2.0416   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441   -2.8432   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8548   -1.4556   -0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945    1.4310    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278   -1.3875    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6982   -0.3625   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2899    1.1366   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    1.3289    2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192    1.3635    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    4.6845    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7173   -0.3114    0.7682 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  5 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  2  0
 20  2  1  0
 13  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

  Mrv0541 10291317312D          

 20 21  0  0  0  0            999 V2000
   -0.4017   -0.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162   -1.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162   -1.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017   -2.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -1.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -1.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4017    0.2214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0271   -0.6035    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307   -0.6035    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    0.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1162    1.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8307    1.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5452    1.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5452    0.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2597    1.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    1.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    2.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1163    3.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126    3.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 12  1  0  0  0  0
 15 11  1  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015403

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)

> <INCHI_KEY>
KHPKQFYUPIUARC-UHFFFAOYSA-N

> <FORMULA>
C15H13ClFNO2

> <MOLECULAR_WEIGHT>
293.721

> <EXACT_MASS>
293.061884577

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.531909913563837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
4.311087882666666

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.87317816721037

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.11490126377279

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8911868358338375

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
75.91419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lumiracoxib

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015403
     RDKit          3D
Lumiracoxib
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.6717   -2.4744   -0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -1.6651   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504   -1.9993   -0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -1.2372   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -0.1465    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    0.6130    0.8291 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    0.3501    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738   -0.4863    1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -1.0824    2.3601 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1755   -0.7365    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6767   -0.1552   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965    0.6856   -1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5896    0.9331   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    1.9960   -1.7093 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6353    0.1789    0.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    1.3558    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.6035    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    2.5612   -0.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    3.8466    1.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7312   -0.5873    0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921   -2.6168   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5795   -3.4796   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222   -2.0416   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441   -2.8432   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8548   -1.4556   -0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945    1.4310    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278   -1.3875    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6982   -0.3625   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2899    1.1366   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    1.3289    2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192    1.3635    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    4.6845    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7173   -0.3114    0.7682 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  5 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  2  0
 20  2  1  0
 13  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

HEADER    PROTEIN                                 29-OCT-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-OCT-13         0                                  
HETATM    1  C   UNK     0      -0.750  -1.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.084  -1.897   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.084  -3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.750  -4.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.584  -3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.584  -1.897   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.750   0.413   0.000  0.00  0.00           N+0
HETATM    8 Cl   UNK     0       1.917  -1.127   0.000  0.00  0.00          Cl+0
HETATM    9  F   UNK     0      -3.417  -1.127   0.000  0.00  0.00           F+0
HETATM   10  C   UNK     0      -2.084   1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.417   0.413   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.084   2.723   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.417   3.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.751   2.723   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.751   1.183   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.085   3.493   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.750   3.493   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.750   5.033   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.084   5.803   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.584   5.803   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    1   10                                                       
CONECT    8    6                                                            
CONECT    9    2                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10   15                                                       
CONECT   12   13   10   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   11                                                       
CONECT   16   14                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0015403
HETATM    1  C1  UNL     1      -3.672  -2.474  -0.838  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.517  -1.665  -0.400  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.250  -1.999  -0.823  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.161  -1.237  -0.410  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.361  -0.147   0.424  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.762   0.613   0.829  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.087   0.350   0.453  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.874  -0.486   1.229  1.00  0.00           C  
HETATM    9  F1  UNL     1       2.429  -1.082   2.360  1.00  0.00           F  
HETATM   10  C8  UNL     1       4.175  -0.737   0.847  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.677  -0.155  -0.295  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.897   0.686  -1.082  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.590   0.933  -0.693  1.00  0.00           C  
HETATM   14 CL1  UNL     1       1.640   1.996  -1.709  1.00  0.00          CL  
HETATM   15  C12 UNL     1      -1.635   0.179   0.842  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.847   1.356   1.742  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.731   2.604   0.946  1.00  0.00           C  
HETATM   18  O1  UNL     1      -1.488   2.561  -0.296  1.00  0.00           O  
HETATM   19  O2  UNL     1      -1.883   3.847   1.525  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.731  -0.587   0.427  1.00  0.00           C  
HETATM   21  H1  UNL     1      -3.692  -2.617  -1.945  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.580  -3.480  -0.383  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.622  -2.042  -0.485  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.044  -2.843  -1.475  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.855  -1.456  -0.712  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.594   1.431   1.455  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.828  -1.388   1.428  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.698  -0.363  -0.579  1.00  0.00           H  
HETATM   29  H9  UNL     1       4.290   1.137  -1.970  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.870   1.329   2.173  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.119   1.363   2.553  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.475   4.685   1.115  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.717  -0.311   0.768  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   20
CONECT    3    4   24
CONECT    4    5    5   25
CONECT    5    6   15
CONECT    6    7   26
CONECT    7    8    8   13
CONECT    8    9   10
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14
CONECT   15   16   20   20
CONECT   16   17   30   31
CONECT   17   18   18   19
CONECT   19   32
CONECT   20   33
END

HMDB0015403
     RDKit          3D
Lumiracoxib
 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.6717   -2.4744   -0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5170   -1.6651   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2504   -1.9993   -0.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1610   -1.2372   -0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -0.1465    0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7617    0.6130    0.8291 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    0.3501    0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8738   -0.4863    1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4295   -1.0824    2.3601 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1755   -0.7365    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6767   -0.1552   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965    0.6856   -1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5896    0.9331   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    1.9960   -1.7093 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6353    0.1789    0.8417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8472    1.3558    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.6035    0.9456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    2.5612   -0.2957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8826    3.8466    1.5250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7312   -0.5873    0.4271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6921   -2.6168   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5795   -3.4796   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6222   -2.0416   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441   -2.8432   -1.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8548   -1.4556   -0.7122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5945    1.4310    1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278   -1.3875    1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6982   -0.3625   -0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2899    1.1366   -1.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8699    1.3289    2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192    1.3635    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4753    4.6845    1.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7173   -0.3114    0.7682 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  5 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 15 20  2  0
 20  2  1  0
 13  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetic acid	ChEBI
COX 189	ChEBI
COX-189	ChEBI
COX189	ChEBI
Lumiracoxibum	ChEBI
Prexige	ChEBI
2-((2-Chloro-6-fluorophenyl)amino)-5-methylbenzeneacetate	Generator

Chemical Formula

C₁₅H₁₃ClFNO₂

Average Molecular Weight

293.721

Monoisotopic Molecular Weight

293.061884577

IUPAC Name

2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid

Traditional Name

lumiracoxib

CAS Registry Number

220991-20-8

SMILES

CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1

InChI Identifier

InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)

InChI Key

KHPKQFYUPIUARC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Toluenes

Direct Parent

Aminotoluenes

Alternative Parents

Substituents

Aminotoluene
Aniline or substituted anilines
Chlorobenzene
Fluorobenzene
Halobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Secondary amine
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organohalogen compound
Organochloride
Organofluoride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:73044 )
monocarboxylic acid (CHEBI:73044 )
organochlorine compound (CHEBI:73044 )
secondary amino compound (CHEBI:73044 )
amino acid (CHEBI:73044 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015403)
Membrane (HMDB: HMDB0015403)

Source

Exogenous

Exogenous (HMDB: HMDB0015403)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Lumiracoxib Action Pathway (PathBank: SMP0000699)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0055 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0055 g/L	ALOGPS
logP	4.56	ALOGPS
logP	4.31	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.91 m³·mol⁻¹	ChemAxon
Polarizability	28.53 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]+	167.651	30932474
DeepCCS	[M-H]-	165.293	30932474
DeepCCS	[M-2H]-	198.179	30932474
DeepCCS	[M+Na]+	173.744	30932474
AllCCS	[M+H]+	162.6	32859911
AllCCS	[M+H-H2O]+	159.1	32859911
AllCCS	[M+NH4]+	165.9	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	159.8	32859911
AllCCS	[M+HCOO]-	159.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lumiracoxib	CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1	3907.3	Standard polar	33892256
Lumiracoxib	CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1	2324.9	Standard non polar	33892256
Lumiracoxib	CC1=CC=C(NC2=C(Cl)C=CC=C2F)C(CC(O)=O)=C1	2317.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lumiracoxib,1TMS,isomer #1	CC1=CC=C(NC2=C(F)C=CC=C2Cl)C(CC(=O)O[Si](C)(C)C)=C1	2266.5	Semi standard non polar	33892256
Lumiracoxib,1TMS,isomer #2	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O)=C1	2276.7	Semi standard non polar	33892256
Lumiracoxib,2TMS,isomer #1	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2253.8	Semi standard non polar	33892256
Lumiracoxib,2TMS,isomer #1	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2227.9	Standard non polar	33892256
Lumiracoxib,2TMS,isomer #1	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2624.5	Standard polar	33892256
Lumiracoxib,1TBDMS,isomer #1	CC1=CC=C(NC2=C(F)C=CC=C2Cl)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2518.4	Semi standard non polar	33892256
Lumiracoxib,1TBDMS,isomer #2	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1	2509.2	Semi standard non polar	33892256
Lumiracoxib,2TBDMS,isomer #1	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2733.6	Semi standard non polar	33892256
Lumiracoxib,2TBDMS,isomer #1	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2629.8	Standard non polar	33892256
Lumiracoxib,2TBDMS,isomer #1	CC1=CC=C(N(C2=C(F)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2848.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lumiracoxib GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2290000000-3dc98edbc540838a7548	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumiracoxib GC-MS (1 TMS) - 70eV, Positive	splash10-00g1-9152000000-5997fd55576c52d1c4b4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lumiracoxib 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 - Lumiracoxib 10V, Positive-QTOF	splash10-002f-0090000000-df6ae4f2e3e5251bab0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 20V, Positive-QTOF	splash10-0002-0090000000-4e4dbea4d96e0566d989	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 40V, Positive-QTOF	splash10-001j-2190000000-a2a86d3a4122bc5a8756	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 10V, Negative-QTOF	splash10-0007-0090000000-e36154890c850cdb9918	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 20V, Negative-QTOF	splash10-0007-0090000000-554e0c5cc5da60a0d0b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 40V, Negative-QTOF	splash10-05cv-3390000000-1fff2d7114e1511e7bb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 10V, Positive-QTOF	splash10-0059-0090000000-15adaa3f8cb7a5dad42c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 20V, Positive-QTOF	splash10-000t-0090000000-954aa7c9b32169c17166	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 40V, Positive-QTOF	splash10-0a5a-0970000000-6662a5b1b7750d52f2c0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 10V, Negative-QTOF	splash10-0006-0090000000-57cb6b0c2531295b071d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 20V, Negative-QTOF	splash10-00e9-2090000000-6ff6b3cb100db6c9f325	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lumiracoxib 40V, Negative-QTOF	splash10-001i-9050000000-93dedc8134cc64db3e8d	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
Lumiracoxib 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 DB01283	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01283	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01283

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

133236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lumiracoxib

METLIN ID

Not Available

PubChem Compound

151166

PDB ID

Not Available

ChEBI ID

73044

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. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. 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

Capone ML, Tacconelli S, Sciulli MG, Patrignani P: Clinical pharmacology of selective COX-2 inhibitors. Int J Immunopathol Pharmacol. 2003 May-Aug;16(2 Suppl):49-58. [PubMed:14552704 ]
Tacconelli S, Capone ML, Patrignani P: Clinical pharmacology of novel selective COX-2 inhibitors. Curr Pharm Des. 2004;10(6):589-601. [PubMed:14965322 ]
Atherton C, Jones J, McKaig B, Bebb J, Cunliffe R, Burdsall J, Brough J, Stevenson D, Bonner J, Rordorf C, Scott G, Branson J, Hawkey CJ: Pharmacology and gastrointestinal safety of lumiracoxib, a novel cyclooxygenase-2 selective inhibitor: An integrated study. Clin Gastroenterol Hepatol. 2004 Feb;2(2):113-20. [PubMed:15017615 ]
Kalbag J, Yeh CM, Milosavljev S, Lasseter K, Oberstein S, Rordorf C: No influence of moderate hepatic impairment on the pharmacokinetics of lumiracoxib, an oral COX-2 selective inhibitor. Pharmacol Res. 2004 Aug;50(2):181-6. [PubMed:15177307 ]
Esser R, Berry C, Du Z, Dawson J, Fox A, Fujimoto RA, Haston W, Kimble EF, Koehler J, Peppard J, Quadros E, Quintavalla J, Toscano K, Urban L, van Duzer J, Zhang X, Zhou S, Marshall PJ: Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2. Br J Pharmacol. 2005 Feb;144(4):538-50. [PubMed:15655513 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. 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

Capone ML, Tacconelli S, Sciulli MG, Patrignani P: Clinical pharmacology of selective COX-2 inhibitors. Int J Immunopathol Pharmacol. 2003 May-Aug;16(2 Suppl):49-58. [PubMed:14552704 ]
Esser R, Berry C, Du Z, Dawson J, Fox A, Fujimoto RA, Haston W, Kimble EF, Koehler J, Peppard J, Quadros E, Quintavalla J, Toscano K, Urban L, van Duzer J, Zhang X, Zhou S, Marshall PJ: Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2. Br J Pharmacol. 2005 Feb;144(4):538-50. [PubMed:15655513 ]
Jermany J, Branson J, Schmouder R, Guillaume M, Rordorf C: Lumiracoxib does not affect the ex vivo antiplatelet aggregation activity of low-dose aspirin in healthy subjects. J Clin Pharmacol. 2005 Oct;45(10):1172-8. [PubMed:16172182 ]
Warner TD, Vojnovic I, Bishop-Bailey D, Mitchell JA: Influence of plasma protein on the potencies of inhibitors of cyclooxygenase-1 and -2. FASEB J. 2006 Mar;20(3):542-4. Epub 2006 Jan 10. [PubMed:16403783 ]
Blobaum AL, Marnett LJ: Molecular determinants for the selective inhibition of cyclooxygenase-2 by lumiracoxib. J Biol Chem. 2007 Jun 1;282(22):16379-90. Epub 2007 Apr 12. [PubMed:17434872 ]

Enzyme Details

4. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Lumiracoxib (HMDB0015403)

MOL for HMDB0015403 (Lumiracoxib)

3D MOL for HMDB0015403 (Lumiracoxib)

3D SDF for HMDB0015403 (Lumiracoxib)

3D-SDF for HMDB0015403 (Lumiracoxib)

PDB for HMDB0015403 (Lumiracoxib)

3D PDB for HMDB0015403 (Lumiracoxib)

SMILES for HMDB0015403 (Lumiracoxib)

INCHI for HMDB0015403 (Lumiracoxib)

Structure for HMDB0015403 (Lumiracoxib)

3D Structure for HMDB0015403 (Lumiracoxib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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