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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (19)transporters (6) Show 25 proteins XML

enzymes (19)transporters (6) Show 25 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:00:39 UTC

Update Date

2020-11-09 23:29:19 UTC

HMDB ID

HMDB0013974

Secondary Accession Numbers

HMDB13974

Metabolite Identification

Common Name

4'-Hydroxydiclofenac

Description

4'-Hydroxydiclofenac is only found in individuals that have used or taken Diclofenac. 4'-Hydroxydiclofenac is a metabolite of Diclofenac. 4'-hydroxydiclofenac belongs to the family of Phenylacetic Acid Derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.

Structure

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

HMDB0013974
     RDKit          3D
4'-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.5926   -2.7471   -0.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -2.0484   -1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -2.7600   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6220   -0.5779   -1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781    0.2292   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    0.8301    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    1.5881    1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    1.7826    1.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5666    1.2041    1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8472    0.4222    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -0.1692   -0.6751 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.0511   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -0.8241    0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -1.8407    1.6077 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -0.7663    0.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157    0.0441    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6881    0.1029    0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.8058   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    0.7431   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    1.7446   -2.3697 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6696   -2.2247   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6790   -0.3174   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601   -0.4678   -2.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2179    0.7144    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539    2.0408    2.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    2.3889    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4762    1.3660    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -0.7023   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806   -1.3627    1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -0.5828   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.4355   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 10  5  1  0
 19 12  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv0541 06191310362D          

 20 21  0  0  0  0            999 V2000
   10.0094   -4.5378    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1514   -4.5378    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8659   -0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2949   -0.8251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805   -3.7127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2949   -2.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2949   -3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805   -2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805   -4.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0094   -2.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0094   -3.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7238   -2.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7238   -3.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2949   -4.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8659   -4.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2949   -5.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8659   -5.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805   -6.1879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5805   -7.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3 16  1  0  0  0  0
  4 16  2  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  8 16  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  2  0  0  0  0
 14 17  1  0  0  0  0
 15 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013974

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O)C=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C14H11Cl2NO3/c15-10-6-9(18)7-11(16)14(10)17-12-4-2-1-3-8(12)5-13(19)20/h1-4,6-7,17-18H,5H2,(H,19,20)

> <INCHI_KEY>
KGVXVPRLBMWZLG-UHFFFAOYSA-N

> <FORMULA>
C14H11Cl2NO3

> <MOLECULAR_WEIGHT>
312.148

> <EXACT_MASS>
311.011598637

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.124899386929208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acid

> <ALOGPS_LOGP>
4.43

> <JCHEM_LOGP>
3.9554439116666664

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.612698331300047

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7610222336655195

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5861817590520623

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
77.44230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4'-hydroxydiclofenac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013974
     RDKit          3D
4'-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.5926   -2.7471   -0.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -2.0484   -1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -2.7600   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6220   -0.5779   -1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781    0.2292   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    0.8301    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    1.5881    1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    1.7826    1.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5666    1.2041    1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8472    0.4222    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -0.1692   -0.6751 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.0511   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -0.8241    0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -1.8407    1.6077 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -0.7663    0.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157    0.0441    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6881    0.1029    0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.8058   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    0.7431   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    1.7446   -2.3697 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6696   -2.2247   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6790   -0.3174   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601   -0.4678   -2.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2179    0.7144    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539    2.0408    2.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    2.3889    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4762    1.3660    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -0.7023   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806   -1.3627    1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -0.5828   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.4355   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 10  5  1  0
 19 12  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1 Cl   UNK     0      18.684  -8.471   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0      13.349  -8.471   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0      14.683  -1.540   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.350  -1.540   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      16.017  -6.930   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      17.350  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.350  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.017  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.017  -8.471   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.684  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.684  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.018  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.018  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.350  -9.241   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.683  -9.241   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.017  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.350 -10.781   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.683 -10.781   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.017 -11.551   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.017 -13.091   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5    7    9                                                       
CONECT    6    7    8   10                                                  
CONECT    7    5    6   11                                                  
CONECT    8    6   16                                                       
CONECT    9    5   14   15                                                  
CONECT   10    6   12                                                       
CONECT   11    7   13                                                       
CONECT   12   10   13                                                       
CONECT   13   11   12                                                       
CONECT   14    1    9   17                                                  
CONECT   15    2    9   18                                                  
CONECT   16    3    4    8                                                  
CONECT   17   14   19                                                       
CONECT   18   15   19                                                       
CONECT   19   17   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0013974
HETATM    1  O1  UNL     1      -1.593  -2.747  -0.977  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.633  -2.048  -1.116  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.830  -2.760  -0.943  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.622  -0.578  -1.435  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.178   0.229  -0.314  1.00  0.00           C  
HETATM    6  C4  UNL     1      -3.152   0.830   0.468  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.857   1.588   1.572  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.531   1.783   1.949  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.567   1.204   1.200  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.847   0.422   0.063  1.00  0.00           C  
HETATM   11  N1  UNL     1       0.181  -0.169  -0.675  1.00  0.00           N  
HETATM   12  C9  UNL     1       1.554  -0.051  -0.365  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.110  -0.824   0.667  1.00  0.00           C  
HETATM   14 CL1  UNL     1       1.024  -1.841   1.608  1.00  0.00          CL  
HETATM   15  C11 UNL     1       3.457  -0.766   0.941  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.316   0.044   0.223  1.00  0.00           C  
HETATM   17  O3  UNL     1       5.688   0.103   0.503  1.00  0.00           O  
HETATM   18  C13 UNL     1       3.800   0.806  -0.788  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.437   0.743  -1.059  1.00  0.00           C  
HETATM   20 CL2  UNL     1       1.809   1.745  -2.370  1.00  0.00          CL  
HETATM   21  H1  UNL     1      -4.670  -2.225  -0.695  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.679  -0.317  -1.692  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.060  -0.468  -2.352  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.218   0.714   0.214  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.654   2.041   2.177  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.317   2.389   2.825  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.476   1.366   1.522  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.047  -0.702  -1.519  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.881  -1.363   1.746  1.00  0.00           H  
HETATM   30  H10 UNL     1       6.268  -0.583  -0.020  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.454   1.435  -1.359  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   21
CONECT    4    5   22   23
CONECT    5    6    6   10
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11
CONECT   11   12   28
CONECT   12   13   13   19
CONECT   13   14   15
CONECT   15   16   16   29
CONECT   16   17   18
CONECT   17   30
CONECT   18   19   19   31
CONECT   19   20
END

HMDB0013974
     RDKit          3D
4'-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.5926   -2.7471   -0.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6335   -2.0484   -1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -2.7600   -0.9430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6220   -0.5779   -1.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781    0.2292   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    0.8301    0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8566    1.5881    1.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    1.7826    1.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5666    1.2041    1.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8472    0.4222    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -0.1692   -0.6751 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536   -0.0511   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1097   -0.8241    0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -1.8407    1.6077 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -0.7663    0.9405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3157    0.0441    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6881    0.1029    0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.8058   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366    0.7431   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    1.7446   -2.3697 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6696   -2.2247   -0.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6790   -0.3174   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0601   -0.4678   -2.3522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2179    0.7144    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539    2.0408    2.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3167    2.3889    2.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4762    1.3660    1.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470   -0.7023   -1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806   -1.3627    1.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684   -0.5828   -0.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4539    1.4355   -1.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 10  5  1  0
 19 12  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(O-(2,6-Dichloro-4-hydroxyanilino)phenyl)acetic acid	ChEBI
4'-Hydroxy diclofenac	ChEBI
4'-OH DCF	ChEBI
(O-(2,6-Dichloro-4-hydroxyanilino)phenyl)acetate	Generator
{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acid	HMDB
4-Hydroxy diclofenac	HMDB

Chemical Formula

C₁₄H₁₁Cl₂NO₃

Average Molecular Weight

312.148

Monoisotopic Molecular Weight

311.011598637

IUPAC Name

2-{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acid

Traditional Name

4'-hydroxydiclofenac

CAS Registry Number

64118-84-9

SMILES

OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O)C=C1Cl

InChI Identifier

InChI=1S/C14H11Cl2NO3/c15-10-6-9(18)7-11(16)14(10)17-12-4-2-1-3-8(12)5-13(19)20/h1-4,6-7,17-18H,5H2,(H,19,20)

InChI Key

KGVXVPRLBMWZLG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:59613 )
phenols (CHEBI:59613 )
secondary amino compound (CHEBI:59613 )
dichlorobenzene (CHEBI:59613 )

Ontology

Not Available

Liver (HMDB: HMDB0013974)
Kidney (HMDB: HMDB0013974)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013974)

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	3.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0096 g/L	ALOGPS
logP	4.43	ALOGPS
logP	3.96	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-0.59	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	77.44 m³·mol⁻¹	ChemAxon
Polarizability	29.12 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]+	161.835	30932474
DeepCCS	[M-H]-	159.477	30932474
DeepCCS	[M-2H]-	192.363	30932474
DeepCCS	[M+Na]+	167.928	30932474
AllCCS	[M+H]+	164.4	32859911
AllCCS	[M+H-H2O]+	161.1	32859911
AllCCS	[M+NH4]+	167.6	32859911
AllCCS	[M+Na]+	168.4	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	159.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4'-Hydroxydiclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O)C=C1Cl	4600.0	Standard polar	33892256
4'-Hydroxydiclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O)C=C1Cl	2641.4	Standard non polar	33892256
4'-Hydroxydiclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O)C=C1Cl	2727.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4'-Hydroxydiclofenac,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O)C=C1Cl	2501.2	Semi standard non polar	33892256
4'-Hydroxydiclofenac,1TMS,isomer #2	C[Si](C)(C)OC1=CC(Cl)=C(NC2=CC=CC=C2CC(=O)O)C(Cl)=C1	2569.3	Semi standard non polar	33892256
4'-Hydroxydiclofenac,1TMS,isomer #3	C[Si](C)(C)N(C1=CC=CC=C1CC(=O)O)C1=C(Cl)C=C(O)C=C1Cl	2507.4	Semi standard non polar	33892256
4'-Hydroxydiclofenac,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O[Si](C)(C)C)C=C1Cl	2575.4	Semi standard non polar	33892256
4'-Hydroxydiclofenac,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O)C=C1Cl)[Si](C)(C)C	2470.3	Semi standard non polar	33892256
4'-Hydroxydiclofenac,2TMS,isomer #3	C[Si](C)(C)OC1=CC(Cl)=C(N(C2=CC=CC=C2CC(=O)O)[Si](C)(C)C)C(Cl)=C1	2511.1	Semi standard non polar	33892256
4'-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O[Si](C)(C)C)C=C1Cl)[Si](C)(C)C	2514.3	Semi standard non polar	33892256
4'-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O[Si](C)(C)C)C=C1Cl)[Si](C)(C)C	2508.1	Standard non polar	33892256
4'-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O[Si](C)(C)C)C=C1Cl)[Si](C)(C)C	2789.0	Standard polar	33892256
4'-Hydroxydiclofenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O)C=C1Cl	2762.4	Semi standard non polar	33892256
4'-Hydroxydiclofenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(Cl)=C(NC2=CC=CC=C2CC(=O)O)C(Cl)=C1	2810.6	Semi standard non polar	33892256
4'-Hydroxydiclofenac,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1CC(=O)O)C1=C(Cl)C=C(O)C=C1Cl	2742.5	Semi standard non polar	33892256
4'-Hydroxydiclofenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C=C1Cl	3026.1	Semi standard non polar	33892256
4'-Hydroxydiclofenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O)C=C1Cl)[Si](C)(C)C(C)(C)C	2946.0	Semi standard non polar	33892256
4'-Hydroxydiclofenac,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(Cl)=C(N(C2=CC=CC=C2CC(=O)O)[Si](C)(C)C(C)(C)C)C(Cl)=C1	2987.4	Semi standard non polar	33892256
4'-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C=C1Cl)[Si](C)(C)C(C)(C)C	3201.7	Semi standard non polar	33892256
4'-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C=C1Cl)[Si](C)(C)C(C)(C)C	3123.7	Standard non polar	33892256
4'-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=C(O[Si](C)(C)C(C)(C)C)C=C1Cl)[Si](C)(C)C(C)(C)C	3072.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-Hydroxydiclofenac GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3190000000-25ce329c964159e0d7b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-Hydroxydiclofenac GC-MS (2 TMS) - 70eV, Positive	splash10-006x-8029300000-4d616f6edc330b477895	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4'-Hydroxydiclofenac 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-014i-0091000000-09a6e4f2f72b1efdd1e3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-014i-0090000000-f6075707e7d10cfdc0f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-0159-0980000000-6a8b77e985a0c629688e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-014i-0920000000-79eb4df0e476648a8c96	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-014i-0900000000-b6ccaa680b1ad83bdd0d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-014i-0900000000-d83cf910c878ae6f1830	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-03dl-2900000000-e55d97b337566e735263	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-0h93-9500000000-7d4d0bd8b2716cf8827a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , negative-QTOF	splash10-0udi-9000000000-5b6172743cd1c276862a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-02tc-0093000000-bf74c218197bc58807bb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-001i-0090000000-a979107147ec17e9859e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-001i-0090000000-118c10ddba962a902170	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-001i-0090000000-b3ed2e7bca59fc876fda	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-001i-0090000000-76e8de6bb0949fde240f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-001i-0390000000-304796a3d9841ccdcae2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-014i-0910000000-5e5782b650537ff5664b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-014r-0900000000-e1567d66af55e61a2021	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac LC-ESI-QFT , positive-QTOF	splash10-00ku-2900000000-1fba80e85d14e8642f62	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4'-Hydroxydiclofenac 30V, Positive-QTOF	splash10-001i-0090000000-b48940be8afea41e4314	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxydiclofenac 10V, Positive-QTOF	splash10-03dl-0096000000-a80b9f12328f8329ce95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxydiclofenac 20V, Positive-QTOF	splash10-014i-0090000000-17cbc61457ac744e81b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxydiclofenac 40V, Positive-QTOF	splash10-0gb9-2190000000-f07e15b3c2f7d8498799	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxydiclofenac 10V, Negative-QTOF	splash10-03xr-0059000000-e80b7aefe1c404165a4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxydiclofenac 20V, Negative-QTOF	splash10-03xr-0095000000-ec4d0fb1cc75e756a5fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4'-Hydroxydiclofenac 40V, Negative-QTOF	splash10-052f-4490000000-80e01d0c3fc669379160	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Diclofenac Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

104192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

116545

PDB ID

Not Available

ChEBI ID

59613

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

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Phospholipase A2, membrane associated

General function:: Involved in phospholipase A2 activity
Specific function:: Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G2A
Uniprot ID:: P14555
Molecular weight:: 16082.525

References

Madanick RD, O'Loughlin CJ, Barkin JS: Diclofenac reduces the incidence of acute pancreatitis after endoscopic retrograde cholangiopancreatography. Dig Dis Sci. 2005 May;50(5):879-81. [PubMed:15906762 ]
Singh N, Jabeen T, Sharma S, Somvanshi RK, Dey S, Srinivasan A, Singh TP: Specific binding of non-steroidal anti-inflammatory drugs (NSAIDs) to phospholipase A2: structure of the complex formed between phospholipase A2 and diclofenac at 2.7 A resolution. Acta Crystallogr D Biol Crystallogr. 2006 Apr;62(Pt 4):410-6. Epub 2006 Mar 18. [PubMed:16552142 ]
Makela A, Kuusi T, Schroder T: Inhibition of serum phospholipase-A2 in acute pancreatitis by pharmacological agents in vitro. Scand J Clin Lab Invest. 1997 Aug;57(5):401-7. [PubMed:9279965 ]

Enzyme Details

2. UDP-glucuronosyltransferase 2B7

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. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

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

3. UDP-glucuronosyltransferase 1-1

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 glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

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

4. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

References

Charlier C, Michaux C: Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. Eur J Med Chem. 2003 Jul-Aug;38(7-8):645-59. [PubMed:12932896 ]
Kudo C, Kori M, Matsuzaki K, Yamai K, Nakajima A, Shibuya A, Niwa H, Kamisaki Y, Wada K: Diclofenac inhibits proliferation and differentiation of neural stem cells. Biochem Pharmacol. 2003 Jul 15;66(2):289-95. [PubMed:12826271 ]
Whittle BJ: Cyclooxygenase and nitric oxide systems in the gut as therapeutic targets for safer anti-inflammatory drugs. Curr Opin Pharmacol. 2004 Dec;4(6):538-45. [PubMed:15525540 ]

Enzyme Details

5. 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

Kirchheiner J, Meineke I, Steinbach N, Meisel C, Roots I, Brockmoller J: Pharmacokinetics of diclofenac and inhibition of cyclooxygenases 1 and 2: no relationship to the CYP2C9 genetic polymorphism in humans. Br J Clin Pharmacol. 2003 Jan;55(1):51-61. [PubMed:12534640 ]
Blomme EA, Chinn KS, Hardy MM, Casler JJ, Kim SH, Opsahl AC, Hall WA, Trajkovic D, Khan KN, Tripp CS: Selective cyclooxygenase-2 inhibition does not affect the healing of cutaneous full-thickness incisional wounds in SKH-1 mice. Br J Dermatol. 2003 Feb;148(2):211-23. [PubMed:12588370 ]
Beubler E: [Pharmacology of cyclooxygenase 2 inhibition]. Wien Med Wochenschr. 2003;153(5-6):95-9. [PubMed:12705061 ]
Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [PubMed:12852704 ]
Rowlinson SW, Kiefer JR, Prusakiewicz JJ, Pawlitz JL, Kozak KR, Kalgutkar AS, Stallings WC, Kurumbail RG, Marnett LJ: A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385. J Biol Chem. 2003 Nov 14;278(46):45763-9. Epub 2003 Aug 18. [PubMed:12925531 ]

Enzyme Details

6. 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

Calkin AC, Sudhir K, Honisett S, Williams MR, Dawood T, Komesaroff PA: Rapid potentiation of endothelium-dependent vasodilation by estradiol in postmenopausal women is mediated via cyclooxygenase 2. J Clin Endocrinol Metab. 2002 Nov;87(11):5072-5. [PubMed:12414874 ]
Kirchheiner J, Meineke I, Steinbach N, Meisel C, Roots I, Brockmoller J: Pharmacokinetics of diclofenac and inhibition of cyclooxygenases 1 and 2: no relationship to the CYP2C9 genetic polymorphism in humans. Br J Clin Pharmacol. 2003 Jan;55(1):51-61. [PubMed:12534640 ]
Kampfer H, Brautigam L, Geisslinger G, Pfeilschifter J, Frank S: Cyclooxygenase-1-coupled prostaglandin biosynthesis constitutes an essential prerequisite for skin repair. J Invest Dermatol. 2003 May;120(5):880-90. [PubMed:12713596 ]
Chavez ML, DeKorte CJ: Valdecoxib: a review. Clin Ther. 2003 Mar;25(3):817-51. [PubMed:12852704 ]
Hinz B, Rau T, Auge D, Werner U, Ramer R, Rietbrock S, Brune K: Aceclofenac spares cyclooxygenase 1 as a result of limited but sustained biotransformation to diclofenac. Clin Pharmacol Ther. 2003 Sep;74(3):222-35. [PubMed:12966366 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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

7. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

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

8. 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

Mo SL, Zhou ZW, Yang LP, Wei MQ, Zhou SF: New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126. [PubMed:20167001 ]
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 ]
Obach RS, Reed-Hagen AE: Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos. 2002 Jul;30(7):831-7. [PubMed:12065442 ]
Leemann T, Transon C, Dayer P: Cytochrome P450TB (CYP2C): a major monooxygenase catalyzing diclofenac 4'-hydroxylation in human liver. Life Sci. 1993;52(1):29-34. [PubMed:8417277 ]

Enzyme Details

9. 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

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

10. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

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 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1C1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-glucuronosyl estradiol, estrone-3-sulfate and sulfobromophthalein (BSP) are transported with much lower efficiency
Gene Name:: SLCO1C1
Uniprot ID:: Q9NYB5
Molecular weight:: 78695.6

References

Westholm DE, Stenehjem DD, Rumbley JN, Drewes LR, Anderson GW: Competitive inhibition of organic anion transporting polypeptide 1c1-mediated thyroxine transport by the fenamate class of nonsteroidal antiinflammatory drugs. Endocrinology. 2009 Feb;150(2):1025-32. doi: 10.1210/en.2008-0188. Epub 2008 Oct 9. [PubMed:18845642 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412 ]

Enzyme Details

3. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [PubMed:11743742 ]

Enzyme Details

4. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [PubMed:10660625 ]

Enzyme Details

5. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412 ]

Enzyme Details

6. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]
Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]

Only showing the first 10 proteins. There are 25 proteins in total.

Show all enzymes and transporters

Showing metabocard for 4'-Hydroxydiclofenac (HMDB0013974)

MOL for HMDB0013974 (4'-Hydroxydiclofenac)

3D MOL for HMDB0013974 (4'-Hydroxydiclofenac)

3D SDF for HMDB0013974 (4'-Hydroxydiclofenac)

3D-SDF for HMDB0013974 (4'-Hydroxydiclofenac)

PDB for HMDB0013974 (4'-Hydroxydiclofenac)

3D PDB for HMDB0013974 (4'-Hydroxydiclofenac)

SMILES for HMDB0013974 (4'-Hydroxydiclofenac)

INCHI for HMDB0013974 (4'-Hydroxydiclofenac)

Structure for HMDB0013974 (4'-Hydroxydiclofenac)

3D Structure for HMDB0013974 (4'-Hydroxydiclofenac)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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