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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:58:41 UTC

Update Date

2019-07-23 07:15:04 UTC

HMDB ID

HMDB0060775

Secondary Accession Numbers

HMDB60775

Metabolite Identification

Common Name

5-Carboxy-lumiracoxib

Description

5-Carboxy-lumiracoxib belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug, manufactured by Novartis and still sold in few countries, including Mexico, Ecuador and the Dominican Republic, under the trade name Prexige (sometimes misquoted as 'Prestige' by the media). 5-Carboxy-lumiracoxib is a metabolite of lumiracoxib. 5-Carboxy-lumiracoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). Lumiracoxib has several distinctive features.

Structure

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

HMDB0060775
     RDKit          3D
5-Carboxy-lumiracoxib
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.9387    2.9887    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8348    1.9637   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    2.3487   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175    1.3886   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    0.0416   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083   -0.9374   -0.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5892   -0.6498   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -0.4503   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.5641   -2.8787 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.1636   -1.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985   -0.0854   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849   -0.2814    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -0.1989    2.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -0.3793    3.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815    0.0744    2.2207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3206   -0.5639    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366   -0.7540    2.1678 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217   -0.3562   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -1.8007   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -2.4612    1.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -1.7840    2.0618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5808   -3.7991    1.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    0.6208   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4157    2.9506    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968    2.7962   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4658    3.9814   -0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    3.4036    0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5002    1.7293   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0475   -1.9479   -0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0918   -0.0076   -2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    0.1361   -0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2245    0.6158    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -2.3044   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5929   -1.8322   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4664   -4.0297    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1615    0.3113   -0.0652 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  1  0
 13 14  2  0
 13 15  1  0
 12 16  2  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  2  0
 23  2  1  0
 16  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 15 32  1  0
 19 33  1  0
 19 34  1  0
 22 35  1  0
 23 36  1  0
M  END


  Mrv0541 07041311582D          

 23 24  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22 16  2  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060775

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H13ClFNO4/c1-8-2-5-12(9(6-8)7-13(20)21)19-15-11(17)4-3-10(14(15)18)16(22)23/h2-6,19H,7H2,1H3,(H,20,21)(H,22,23)

> <INCHI_KEY>
DAMRUBXLPVLGQF-UHFFFAOYSA-N

> <FORMULA>
C16H13ClFNO4

> <MOLECULAR_WEIGHT>
337.73

> <EXACT_MASS>
337.051713821

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.942340420994203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[2-(carboxymethyl)-4-methylphenyl]amino}-4-chloro-2-fluorobenzoic acid

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.968670790666666

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.500468679614343

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5739841348241743

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1425111049204872

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
83.1704

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[2-(carboxymethyl)-4-methylphenyl]amino}-4-chloro-2-fluorobenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060775
     RDKit          3D
5-Carboxy-lumiracoxib
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.9387    2.9887    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8348    1.9637   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    2.3487   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175    1.3886   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    0.0416   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083   -0.9374   -0.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5892   -0.6498   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -0.4503   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.5641   -2.8787 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.1636   -1.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985   -0.0854   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849   -0.2814    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -0.1989    2.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -0.3793    3.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815    0.0744    2.2207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3206   -0.5639    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366   -0.7540    2.1678 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217   -0.3562   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -1.8007   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -2.4612    1.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -1.7840    2.0618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5808   -3.7991    1.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    0.6208   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4157    2.9506    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968    2.7962   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4658    3.9814   -0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    3.4036    0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5002    1.7293   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0475   -1.9479   -0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0918   -0.0076   -2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    0.1361   -0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2245    0.6158    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -2.3044   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5929   -1.8322   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4664   -4.0297    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1615    0.3113   -0.0652 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  1  0
 13 14  2  0
 13 15  1  0
 12 16  2  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  2  0
 23  2  1  0
 16  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 15 32  1  0
 19 33  1  0
 19 34  1  0
 22 35  1  0
 23 36  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       4.001   2.310   0.000  0.00  0.00          Cl+0
HETATM   18  F   UNK     0       6.668   6.930   0.000  0.00  0.00           F+0
HETATM   19  N   UNK     0       6.668   3.850   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    5    8                                                       
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    2   12                                                       
CONECT    6    8    9                                                       
CONECT    7    9   13                                                       
CONECT    8    1    2    6                                                  
CONECT    9    6    7   12                                                  
CONECT   10    3   14   16                                                  
CONECT   11    4   15   17                                                  
CONECT   12    5    9   19                                                  
CONECT   13    7   20   21                                                  
CONECT   14   10   15   18                                                  
CONECT   15   11   14   19                                                  
CONECT   16   10   22   23                                                  
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   12   15                                                       
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0060775
HETATM    1  C1  UNL     1      -3.939   2.989   0.063  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.835   1.964  -0.007  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.513   2.349  -0.012  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.517   1.389  -0.078  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.807   0.042  -0.139  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.208  -0.937  -0.204  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.589  -0.650  -0.214  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.227  -0.450  -1.413  1.00  0.00           C  
HETATM    9 CL1  UNL     1       1.278  -0.564  -2.879  1.00  0.00          CL  
HETATM   10  C8  UNL     1       3.599  -0.164  -1.467  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.298  -0.085  -0.286  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.685  -0.281   0.939  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.425  -0.199   2.191  1.00  0.00           C  
HETATM   14  O1  UNL     1       3.824  -0.379   3.272  1.00  0.00           O  
HETATM   15  O2  UNL     1       5.782   0.074   2.221  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.321  -0.564   0.945  1.00  0.00           C  
HETATM   17  F1  UNL     1       1.737  -0.754   2.168  1.00  0.00           F  
HETATM   18  C13 UNL     1      -2.122  -0.356  -0.135  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.517  -1.801  -0.200  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.301  -2.461   1.116  1.00  0.00           C  
HETATM   21  O3  UNL     1      -1.849  -1.784   2.062  1.00  0.00           O  
HETATM   22  O4  UNL     1      -2.581  -3.799   1.334  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.125   0.621  -0.069  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.416   2.951   1.076  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.697   2.796  -0.713  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.466   3.981  -0.024  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.304   3.404   0.036  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.500   1.729  -0.080  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.048  -1.948  -0.248  1.00  0.00           H  
HETATM   30  H7  UNL     1       4.092  -0.008  -2.416  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.372   0.136  -0.275  1.00  0.00           H  
HETATM   32  H9  UNL     1       6.224   0.616   1.515  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.908  -2.304  -0.967  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.593  -1.832  -0.492  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.466  -4.030   1.767  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.162   0.311  -0.065  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   23
CONECT    3    4   27
CONECT    4    5    5   28
CONECT    5    6   18
CONECT    6    7   29
CONECT    7    8    8   16
CONECT    8    9   10
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   16   16
CONECT   13   14   14   15
CONECT   15   32
CONECT   16   17
CONECT   18   19   23   23
CONECT   19   20   33   34
CONECT   20   21   21   22
CONECT   22   35
CONECT   23   36
END

HMDB0060775
     RDKit          3D
5-Carboxy-lumiracoxib
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.9387    2.9887    0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8348    1.9637   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    2.3487   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5175    1.3886   -0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    0.0416   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2083   -0.9374   -0.2045 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5892   -0.6498   -0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2273   -0.4503   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.5641   -2.8787 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -0.1636   -1.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985   -0.0854   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849   -0.2814    0.9395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249   -0.1989    2.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242   -0.3793    3.2717 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815    0.0744    2.2207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3206   -0.5639    0.9450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7366   -0.7540    2.1678 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1217   -0.3562   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169   -1.8007   -0.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007   -2.4612    1.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8493   -1.7840    2.0618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5808   -3.7991    1.3341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    0.6208   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4157    2.9506    1.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968    2.7962   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4658    3.9814   -0.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    3.4036    0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5002    1.7293   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0475   -1.9479   -0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0918   -0.0076   -2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3725    0.1361   -0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2245    0.6158    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9076   -2.3044   -0.9674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5929   -1.8322   -0.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4664   -4.0297    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1615    0.3113   -0.0652 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  1  0
 13 14  2  0
 13 15  1  0
 12 16  2  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 18 23  2  0
 23  2  1  0
 16  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
 10 30  1  0
 11 31  1  0
 15 32  1  0
 19 33  1  0
 19 34  1  0
 22 35  1  0
 23 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₃ClFNO₄

Average Molecular Weight

337.73

Monoisotopic Molecular Weight

337.051713821

IUPAC Name

3-{[2-(carboxymethyl)-4-methylphenyl]amino}-4-chloro-2-fluorobenzoic acid

Traditional Name

3-{[2-(carboxymethyl)-4-methylphenyl]amino}-4-chloro-2-fluorobenzoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H13ClFNO4/c1-8-2-5-12(9(6-8)7-13(20)21)19-15-11(17)4-3-10(14(15)18)16(22)23/h2-6,19H,7H2,1H3,(H,20,21)(H,22,23)

InChI Key

DAMRUBXLPVLGQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
2-halobenzoic acid or derivatives
4-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
2-halobenzoic acid
4-halobenzoic acid
Halobenzoic acid
Benzoic acid
Benzoyl
1-carboxy-2-haloaromatic compound
Aminotoluene
Aniline or substituted anilines
Fluorobenzene
Toluene
Halobenzene
Chlorobenzene
Aryl fluoride
Aryl chloride
Dicarboxylic acid or derivatives
Aryl halide
Vinylogous halide
Amino acid
Amino acid or derivatives
Secondary amine
Carboxylic acid derivative
Carboxylic acid
Amine
Organohalogen compound
Organochloride
Organofluoride
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060775)
Liver (HMDB: HMDB0060775)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060775)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060775)

Cellular substructure

Cytoplasm (HMDB: HMDB0060775)
Membrane (HMDB: HMDB0060775)

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
Water Solubility	0.0062 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.97	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.17 m³·mol⁻¹	ChemAxon
Polarizability	31.94 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]+	175.511	30932474
DeepCCS	[M-H]-	173.153	30932474
DeepCCS	[M-2H]-	207.494	30932474
DeepCCS	[M+Na]+	183.779	30932474
AllCCS	[M+H]+	172.6	32859911
AllCCS	[M+H-H2O]+	169.4	32859911
AllCCS	[M+NH4]+	175.5	32859911
AllCCS	[M+Na]+	176.3	32859911
AllCCS	[M-H]-	170.4	32859911
AllCCS	[M+Na-2H]-	169.6	32859911
AllCCS	[M+HCOO]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Carboxy-lumiracoxib	CC1=CC(CC(O)=O)=C(NC2=C(Cl)C=CC(C(O)=O)=C2F)C=C1	4622.4	Standard polar	33892256
5-Carboxy-lumiracoxib	CC1=CC(CC(O)=O)=C(NC2=C(Cl)C=CC(C(O)=O)=C2F)C=C1	2574.3	Standard non polar	33892256
5-Carboxy-lumiracoxib	CC1=CC(CC(O)=O)=C(NC2=C(Cl)C=CC(C(O)=O)=C2F)C=C1	2858.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Carboxy-lumiracoxib,1TMS,isomer #1	CC1=CC=C(NC2=C(Cl)C=CC(C(=O)O)=C2F)C(CC(=O)O[Si](C)(C)C)=C1	2685.3	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,1TMS,isomer #2	CC1=CC=C(NC2=C(Cl)C=CC(C(=O)O[Si](C)(C)C)=C2F)C(CC(=O)O)=C1	2692.7	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,1TMS,isomer #3	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O)=C2F)[Si](C)(C)C)C(CC(=O)O)=C1	2665.0	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,2TMS,isomer #1	CC1=CC=C(NC2=C(Cl)C=CC(C(=O)O[Si](C)(C)C)=C2F)C(CC(=O)O[Si](C)(C)C)=C1	2682.2	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,2TMS,isomer #2	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2631.5	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,2TMS,isomer #3	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O)=C1	2650.5	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,3TMS,isomer #1	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2632.5	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,3TMS,isomer #1	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2599.7	Standard non polar	33892256
5-Carboxy-lumiracoxib,3TMS,isomer #1	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C)=C2F)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2935.3	Standard polar	33892256
5-Carboxy-lumiracoxib,1TBDMS,isomer #1	CC1=CC=C(NC2=C(Cl)C=CC(C(=O)O)=C2F)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2958.7	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,1TBDMS,isomer #2	CC1=CC=C(NC2=C(Cl)C=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)C(CC(=O)O)=C1	2950.6	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,1TBDMS,isomer #3	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1	2926.7	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,2TBDMS,isomer #1	CC1=CC=C(NC2=C(Cl)C=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	3147.0	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,2TBDMS,isomer #2	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	3115.9	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,2TBDMS,isomer #3	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1	3131.8	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,3TBDMS,isomer #1	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	3327.2	Semi standard non polar	33892256
5-Carboxy-lumiracoxib,3TBDMS,isomer #1	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	3112.7	Standard non polar	33892256
5-Carboxy-lumiracoxib,3TBDMS,isomer #1	CC1=CC=C(N(C2=C(Cl)C=CC(C(=O)O[Si](C)(C)C(C)(C)C)=C2F)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	3223.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Carboxy-lumiracoxib GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-1294000000-cd281b89427be66cc0c0	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Carboxy-lumiracoxib GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9118500000-366d91da9d84ca4c75ea	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Carboxy-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 - 5-Carboxy-lumiracoxib 10V, Positive-QTOF	splash10-00di-0029000000-f652e3274936dda6a63b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 20V, Positive-QTOF	splash10-00dl-0295000000-6142026d44ad390cfe1c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 40V, Positive-QTOF	splash10-0002-0290000000-6b835471e60e68e88c32	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 10V, Negative-QTOF	splash10-000l-0069000000-c42604f223097949b79d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 20V, Negative-QTOF	splash10-00kp-0097000000-e096622ba3a1df2e30f8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 40V, Negative-QTOF	splash10-0006-4194000000-b2b3585683248443f0ff	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 10V, Positive-QTOF	splash10-00du-0059000000-08c24298cde3bcf00416	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 20V, Positive-QTOF	splash10-0096-0092000000-2f47ed8382605163796e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 40V, Positive-QTOF	splash10-004l-0090000000-29b5b06a2ff10415c15b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 10V, Negative-QTOF	splash10-0002-0090000000-cd392b03fb39e27ffb45	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 20V, Negative-QTOF	splash10-00dj-0091000000-a9b91cced08c2cfe63f1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Carboxy-lumiracoxib 40V, Negative-QTOF	splash10-000t-2090000000-4ad66c00b6b01a1b70fa	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769946

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

Not Available

Showing metabocard for 5-Carboxy-lumiracoxib (HMDB0060775)

MOL for HMDB0060775 (5-Carboxy-lumiracoxib)

3D MOL for HMDB0060775 (5-Carboxy-lumiracoxib)

3D SDF for HMDB0060775 (5-Carboxy-lumiracoxib)

3D-SDF for HMDB0060775 (5-Carboxy-lumiracoxib)

PDB for HMDB0060775 (5-Carboxy-lumiracoxib)

3D PDB for HMDB0060775 (5-Carboxy-lumiracoxib)

SMILES for HMDB0060775 (5-Carboxy-lumiracoxib)

INCHI for HMDB0060775 (5-Carboxy-lumiracoxib)

Structure for HMDB0060775 (5-Carboxy-lumiracoxib)

3D Structure for HMDB0060775 (5-Carboxy-lumiracoxib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra