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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:07:41 UTC

Update Date

2019-07-23 07:15:23 UTC

HMDB ID

HMDB0060927

Secondary Accession Numbers

HMDB60927

Metabolite Identification

Common Name

Hydroxylumiracoxib

Description

Hydroxylumiracoxib 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 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). Hydroxylumiracoxib is a metabolite of lumiracoxib. Hydroxylumiracoxib 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

HMDB0060927
     RDKit          3D
Hydroxylumiracoxib
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.7633    1.7549    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.1269    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    1.5457    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1855    0.9400    0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117   -0.1101   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277   -0.7263   -0.7183 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1401   -0.2881   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527    0.6970   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9115    1.1881   -2.2931 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    1.1540   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403    0.6246    0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9317    1.0779    0.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1379   -0.3497    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.8177    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277   -2.0742    1.6559 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052   -0.5499   -0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464   -1.6707   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406   -2.0326   -1.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -1.2030   -2.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149   -3.3439   -1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    0.0587    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4159    1.0202    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3407    2.3162    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4502    2.5005    2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    2.3794    2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    1.3242    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505   -1.5249   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574    1.9261   -1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1214    1.8564    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7226   -0.7410    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -2.5651   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -1.4638   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -3.7725   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168   -0.2573   -0.0422 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
 11 13  1  0
 13 14  2  0
 14 15  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  2  0
 21  2  1  0
 14  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 17 32  1  0
 20 33  1  0
 21 34  1  0
M  END


  Mrv0541 07091309072D          

 21 22  0  0  0  0            999 V2000
    2.1434    1.2375    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
    1.4289    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
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    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
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    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
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14  5  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
 19 10  1  0  0  0  0
 20 14  2  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060927

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H13ClFNO3/c1-8-2-3-13(9(4-8)5-14(20)21)18-15-11(16)6-10(19)7-12(15)17/h2-4,6-7,18-19H,5H2,1H3,(H,20,21)

> <INCHI_KEY>
LUNFHOZKXHTOLG-UHFFFAOYSA-N

> <FORMULA>
C15H13ClFNO3

> <MOLECULAR_WEIGHT>
309.72

> <EXACT_MASS>
309.056799199

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.62422349079813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2-[(2-chloro-6-fluoro-4-hydroxyphenyl)amino]-5-methylphenyl}acetic acid

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
4.007522560999999

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.399860025176494

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8784426666809715

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4120785548592939

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
77.89510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{2-[(2-chloro-6-fluoro-4-hydroxyphenyl)amino]-5-methylphenyl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060927
     RDKit          3D
Hydroxylumiracoxib
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.7633    1.7549    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.1269    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    1.5457    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1855    0.9400    0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117   -0.1101   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277   -0.7263   -0.7183 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1401   -0.2881   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527    0.6970   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9115    1.1881   -2.2931 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    1.1540   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403    0.6246    0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9317    1.0779    0.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1379   -0.3497    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.8177    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277   -2.0742    1.6559 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052   -0.5499   -0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464   -1.6707   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406   -2.0326   -1.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -1.2030   -2.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149   -3.3439   -1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    0.0587    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4159    1.0202    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3407    2.3162    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4502    2.5005    2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    2.3794    2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    1.3242    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505   -1.5249   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574    1.9261   -1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1214    1.8564    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7226   -0.7410    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -2.5651   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -1.4638   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -3.7725   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168   -0.2573   -0.0422 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
 11 13  1  0
 13 14  2  0
 14 15  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  2  0
 21  2  1  0
 14  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 17 32  1  0
 20 33  1  0
 21 34  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   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       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       4.001  11.550   0.000  0.00  0.00          Cl+0
HETATM   17  F   UNK     0       1.334   6.930   0.000  0.00  0.00           F+0
HETATM   18  N   UNK     0       4.001   8.470   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    3    8                                                       
CONECT    3    2   13                                                       
CONECT    4    8    9                                                       
CONECT    5    9   14                                                       
CONECT    6   10   11                                                       
CONECT    7   10   12                                                       
CONECT    8    1    2    4                                                  
CONECT    9    4    5   13                                                  
CONECT   10    6    7   19                                                  
CONECT   11    6   15   16                                                  
CONECT   12    7   15   17                                                  
CONECT   13    3    9   18                                                  
CONECT   14    5   20   21                                                  
CONECT   15   11   12   18                                                  
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13   15                                                       
CONECT   19   10                                                            
CONECT   20   14                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0060927
HETATM    1  C1  UNL     1      -3.763   1.755   1.652  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.560   1.127   1.047  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.280   1.546   1.321  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.185   0.940   0.743  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.312  -0.110  -0.135  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.828  -0.726  -0.718  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.140  -0.288  -0.420  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.653   0.697  -1.257  1.00  0.00           C  
HETATM    9  F1  UNL     1       1.911   1.188  -2.293  1.00  0.00           F  
HETATM   10  C8  UNL     1       3.928   1.154  -1.006  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.640   0.625   0.054  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.932   1.078   0.320  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.138  -0.350   0.884  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.856  -0.818   0.641  1.00  0.00           C  
HETATM   15 CL1  UNL     1       2.128  -2.074   1.656  1.00  0.00          CL  
HETATM   16  C12 UNL     1      -1.605  -0.550  -0.426  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.746  -1.671  -1.350  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.141  -2.033  -1.648  1.00  0.00           C  
HETATM   19  O2  UNL     1      -3.956  -1.203  -2.101  1.00  0.00           O  
HETATM   20  O3  UNL     1      -3.615  -3.344  -1.432  1.00  0.00           O  
HETATM   21  C15 UNL     1      -2.683   0.059   0.154  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.416   1.020   2.166  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.341   2.316   0.879  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.450   2.501   2.412  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.152   2.379   2.015  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.795   1.324   1.011  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.651  -1.525  -1.384  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.357   1.926  -1.645  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.121   1.856   0.938  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.723  -0.741   1.705  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.252  -2.565  -0.862  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.248  -1.464  -2.335  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.378  -3.772  -0.540  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.717  -0.257  -0.042  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   16
CONECT    6    7   27
CONECT    7    8    8   14
CONECT    8    9   10
CONECT   10   11   11   28
CONECT   11   12   13
CONECT   12   29
CONECT   13   14   14   30
CONECT   14   15
CONECT   16   17   21   21
CONECT   17   18   31   32
CONECT   18   19   19   20
CONECT   20   33
CONECT   21   34
END

HMDB0060927
     RDKit          3D
Hydroxylumiracoxib
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.7633    1.7549    1.6523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5598    1.1269    1.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    1.5457    1.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1855    0.9400    0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117   -0.1101   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277   -0.7263   -0.7183 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1401   -0.2881   -0.4205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6527    0.6970   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9115    1.1881   -2.2931 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.9276    1.1540   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403    0.6246    0.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9317    1.0779    0.3195 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1379   -0.3497    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.8177    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1277   -2.0742    1.6559 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6052   -0.5499   -0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464   -1.6707   -1.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406   -2.0326   -1.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9555   -1.2030   -2.1008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6149   -3.3439   -1.4322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6834    0.0587    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4159    1.0202    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3407    2.3162    0.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4502    2.5005    2.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    2.3794    2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    1.3242    1.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505   -1.5249   -1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3574    1.9261   -1.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1214    1.8564    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7226   -0.7410    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -2.5651   -0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2483   -1.4638   -2.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3779   -3.7725   -0.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168   -0.2573   -0.0422 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
 11 13  1  0
 13 14  2  0
 14 15  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  2  0
 21  2  1  0
 14  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 17 31  1  0
 17 32  1  0
 20 33  1  0
 21 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃ClFNO₃

Average Molecular Weight

309.72

Monoisotopic Molecular Weight

309.056799199

IUPAC Name

2-{2-[(2-chloro-6-fluoro-4-hydroxyphenyl)amino]-5-methylphenyl}acetic acid

Traditional Name

{2-[(2-chloro-6-fluoro-4-hydroxyphenyl)amino]-5-methylphenyl}acetic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H13ClFNO3/c1-8-2-3-13(9(4-8)5-14(20)21)18-15-11(16)6-10(19)7-12(15)17/h2-4,6-7,18-19H,5H2,1H3,(H,20,21)

InChI Key

LUNFHOZKXHTOLG-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

3-fluorophenol
P-aminophenol
3-chlorophenol
Aminophenol
3-halophenol
Aniline or substituted anilines
Aminotoluene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Fluorobenzene
Phenol
Chlorobenzene
Aryl chloride
Aryl fluoride
Aryl halide
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary amine
Monocarboxylic acid or derivatives
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organofluoride
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060927)
Liver (HMDB: HMDB0060927)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060927)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060927)

Cellular substructure

Cytoplasm (HMDB: HMDB0060927)
Membrane (HMDB: HMDB0060927)

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	0.017 g/L	ALOGPS
logP	3.97	ALOGPS
logP	4.01	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-0.41	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.9 m³·mol⁻¹	ChemAxon
Polarizability	29.62 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]+	168.312	30932474
DeepCCS	[M-H]-	165.954	30932474
DeepCCS	[M-2H]-	198.967	30932474
DeepCCS	[M+Na]+	174.405	30932474
AllCCS	[M+H]+	166.5	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	169.6	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	164.4	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	162.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxylumiracoxib	CC1=CC(CC(O)=O)=C(NC2=C(Cl)C=C(O)C=C2F)C=C1	4391.1	Standard polar	33892256
Hydroxylumiracoxib	CC1=CC(CC(O)=O)=C(NC2=C(Cl)C=C(O)C=C2F)C=C1	2568.9	Standard non polar	33892256
Hydroxylumiracoxib	CC1=CC(CC(O)=O)=C(NC2=C(Cl)C=C(O)C=C2F)C=C1	2672.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxylumiracoxib,1TMS,isomer #1	CC1=CC=C(NC2=C(F)C=C(O)C=C2Cl)C(CC(=O)O[Si](C)(C)C)=C1	2427.7	Semi standard non polar	33892256
Hydroxylumiracoxib,1TMS,isomer #2	CC1=CC=C(NC2=C(F)C=C(O[Si](C)(C)C)C=C2Cl)C(CC(=O)O)=C1	2503.6	Semi standard non polar	33892256
Hydroxylumiracoxib,1TMS,isomer #3	CC1=CC=C(N(C2=C(F)C=C(O)C=C2Cl)[Si](C)(C)C)C(CC(=O)O)=C1	2423.4	Semi standard non polar	33892256
Hydroxylumiracoxib,2TMS,isomer #1	CC1=CC=C(NC2=C(F)C=C(O[Si](C)(C)C)C=C2Cl)C(CC(=O)O[Si](C)(C)C)=C1	2492.0	Semi standard non polar	33892256
Hydroxylumiracoxib,2TMS,isomer #2	CC1=CC=C(N(C2=C(F)C=C(O)C=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2400.2	Semi standard non polar	33892256
Hydroxylumiracoxib,2TMS,isomer #3	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C)C=C2Cl)[Si](C)(C)C)C(CC(=O)O)=C1	2475.6	Semi standard non polar	33892256
Hydroxylumiracoxib,3TMS,isomer #1	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C)C=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2456.4	Semi standard non polar	33892256
Hydroxylumiracoxib,3TMS,isomer #1	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C)C=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2432.7	Standard non polar	33892256
Hydroxylumiracoxib,3TMS,isomer #1	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C)C=C2Cl)[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)=C1	2672.3	Standard polar	33892256
Hydroxylumiracoxib,1TBDMS,isomer #1	CC1=CC=C(NC2=C(F)C=C(O)C=C2Cl)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2687.7	Semi standard non polar	33892256
Hydroxylumiracoxib,1TBDMS,isomer #2	CC1=CC=C(NC2=C(F)C=C(O[Si](C)(C)C(C)(C)C)C=C2Cl)C(CC(=O)O)=C1	2746.8	Semi standard non polar	33892256
Hydroxylumiracoxib,1TBDMS,isomer #3	CC1=CC=C(N(C2=C(F)C=C(O)C=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1	2663.6	Semi standard non polar	33892256
Hydroxylumiracoxib,2TBDMS,isomer #1	CC1=CC=C(NC2=C(F)C=C(O[Si](C)(C)C(C)(C)C)C=C2Cl)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2963.4	Semi standard non polar	33892256
Hydroxylumiracoxib,2TBDMS,isomer #2	CC1=CC=C(N(C2=C(F)C=C(O)C=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2882.7	Semi standard non polar	33892256
Hydroxylumiracoxib,2TBDMS,isomer #3	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C(C)(C)C)C=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1	2930.9	Semi standard non polar	33892256
Hydroxylumiracoxib,3TBDMS,isomer #1	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C(C)(C)C)C=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	3139.3	Semi standard non polar	33892256
Hydroxylumiracoxib,3TBDMS,isomer #1	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C(C)(C)C)C=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2993.0	Standard non polar	33892256
Hydroxylumiracoxib,3TBDMS,isomer #1	CC1=CC=C(N(C2=C(F)C=C(O[Si](C)(C)C(C)(C)C)C=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	2984.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxylumiracoxib GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-1291000000-c332e7828d3fe8ca0ff8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxylumiracoxib GC-MS (2 TMS) - 70eV, Positive	splash10-009i-6219400000-af02a7ac8130c23efff5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxylumiracoxib 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 - Hydroxylumiracoxib 10V, Positive-QTOF	splash10-01ox-0092000000-327818fa05fa295e0cdb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 20V, Positive-QTOF	splash10-03di-0290000000-1ff6b9cacf560390aa96	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 40V, Positive-QTOF	splash10-06r2-2590000000-1eb6cb521023b062cf9f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 10V, Negative-QTOF	splash10-0bt9-0079000000-05ffdb934d4afd3855a6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 20V, Negative-QTOF	splash10-08fu-0093000000-8eac879592f62025c511	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 40V, Negative-QTOF	splash10-0006-4390000000-aa0a4023913419f7bd9d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 10V, Positive-QTOF	splash10-03dl-0093000000-a2ca65d2bfbbbd370622	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 20V, Positive-QTOF	splash10-03di-0091000000-bea4feb0d33c185c15ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 40V, Positive-QTOF	splash10-03dj-0390000000-1ebd4510f8ff84922d7c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 10V, Negative-QTOF	splash10-08fr-0097000000-3142ae9ba40bf36138a7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 20V, Negative-QTOF	splash10-06rx-3092000000-72b5fa093b672ca8f5e2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxylumiracoxib 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	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

9904747

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 Hydroxylumiracoxib (HMDB0060927)

MOL for HMDB0060927 (Hydroxylumiracoxib)

3D MOL for HMDB0060927 (Hydroxylumiracoxib)

3D SDF for HMDB0060927 (Hydroxylumiracoxib)

3D-SDF for HMDB0060927 (Hydroxylumiracoxib)

PDB for HMDB0060927 (Hydroxylumiracoxib)

3D PDB for HMDB0060927 (Hydroxylumiracoxib)

SMILES for HMDB0060927 (Hydroxylumiracoxib)

INCHI for HMDB0060927 (Hydroxylumiracoxib)

Structure for HMDB0060927 (Hydroxylumiracoxib)

3D Structure for HMDB0060927 (Hydroxylumiracoxib)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra