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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:33:01 UTC

Update Date

2019-07-23 07:14:33 UTC

HMDB ID

HMDB0060542

Secondary Accession Numbers

HMDB60542

Metabolite Identification

Common Name

5-Hydroxydiclofenac

Description

5-Hydroxydiclofenac, also known as 5-OH DCF, belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. 5-Hydroxydiclofenac (5-OH-DCF) is a metabolite of Diclofenac. 5-Hydroxydiclofenac is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060542
     RDKit          3D
5-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.4694    0.8622    2.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    2.0377    2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834    3.1158    3.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    2.2727    0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    1.0024   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105    0.5592   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -0.6091   -1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2639   -1.0530   -1.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9245   -1.3859   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7107   -0.9568   -1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    0.2267   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6962    0.6058    0.2050 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -0.2052   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816   -1.1981    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -1.4234    2.2953 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2799   -2.0164    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0849   -1.8641   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512   -0.8688   -1.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6462   -0.0609   -1.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785    1.1702   -2.3269 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    2.9922    3.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    2.8558    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466    2.8972    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142    1.1473   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8374   -1.6512   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -2.3191   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -1.5857   -1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7706    1.4957    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -2.7997    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9538   -2.5068   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725   -0.7364   -2.2129 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 13  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

[NO NAME]
  Mrv0541 04181210282D          
Created with ChemWriter - http://chemwriter.com
 20 21  0  0  0  0            999 V2000
    4.5080   -1.2870    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2870    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.1880    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
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060542

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
VNQURRWYKFZKJZ-UHFFFAOYSA-N

> <FORMULA>
C14H11Cl2NO3

> <MOLECULAR_WEIGHT>
312.148

> <EXACT_MASS>
311.011598637

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.108801608305782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2-[(2,6-dichlorophenyl)amino]-5-hydroxyphenyl}acetic acid

> <ALOGPS_LOGP>
4.27

> <JCHEM_LOGP>
3.9554439116666664

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.87347491698646

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.811685343253948

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6833094714032716

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
77.44230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxydiclofenac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060542
     RDKit          3D
5-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.4694    0.8622    2.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    2.0377    2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834    3.1158    3.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    2.2727    0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    1.0024   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105    0.5592   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -0.6091   -1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2639   -1.0530   -1.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9245   -1.3859   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7107   -0.9568   -1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    0.2267   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6962    0.6058    0.2050 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -0.2052   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816   -1.1981    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -1.4234    2.2953 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2799   -2.0164    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0849   -1.8641   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512   -0.8688   -1.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6462   -0.0609   -1.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785    1.1702   -2.3269 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    2.9922    3.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    2.8558    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466    2.8972    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142    1.1473   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8374   -1.6512   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -2.3191   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -1.5857   -1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7706    1.4957    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -2.7997    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9538   -2.5068   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725   -0.7364   -2.2129 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 13  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 18-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-12         0                                  
HETATM    1 Cl   UNK     0       8.415  -2.402   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -2.402   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       4.414   4.528   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.081   4.528   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.748  -0.862   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.081   1.448   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -0.092   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   2.218   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -2.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -0.862   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   1.448   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -0.092   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -3.172   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -3.172   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   3.758   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -4.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -4.713   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -5.483   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.082   2.218   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   20                                                  
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                                                       
CONECT   20   12                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0060542
HETATM    1  O1  UNL     1      -1.469   0.862   2.622  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.484   2.038   2.153  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.383   3.116   3.015  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.606   2.273   0.697  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.701   1.002  -0.064  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.911   0.559  -0.576  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.049  -0.609  -1.287  1.00  0.00           C  
HETATM    8  O3  UNL     1      -4.264  -1.053  -1.800  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.925  -1.386  -1.505  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.711  -0.957  -1.001  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.583   0.227  -0.283  1.00  0.00           C  
HETATM   12  N1  UNL     1       0.696   0.606   0.205  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.838  -0.205  -0.031  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.182  -1.198   0.875  1.00  0.00           C  
HETATM   15 CL1  UNL     1       1.189  -1.423   2.295  1.00  0.00          CL  
HETATM   16  C11 UNL     1       3.280  -2.016   0.698  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.085  -1.864  -0.414  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.751  -0.869  -1.335  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.646  -0.061  -1.136  1.00  0.00           C  
HETATM   20 CL2  UNL     1       2.279   1.170  -2.327  1.00  0.00          CL  
HETATM   21  H1  UNL     1      -0.725   2.992   3.801  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.528   2.856   0.506  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.747   2.897   0.393  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.814   1.147  -0.422  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.837  -1.651  -1.208  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.017  -2.319  -2.069  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.161  -1.586  -1.185  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.771   1.496   0.740  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.550  -2.800   1.414  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.954  -2.507  -0.560  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.373  -0.736  -2.213  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   11
CONECT    6    7   24
CONECT    7    8    9    9
CONECT    8   25
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12
CONECT   12   13   28
CONECT   13   14   14   19
CONECT   14   15   16
CONECT   16   17   17   29
CONECT   17   18   30
CONECT   18   19   19   31
CONECT   19   20
END

HMDB0060542
     RDKit          3D
5-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -1.4694    0.8622    2.6223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837    2.0377    2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834    3.1158    3.0153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060    2.2727    0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    1.0024   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105    0.5592   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489   -0.6091   -1.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2639   -1.0530   -1.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9245   -1.3859   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7107   -0.9568   -1.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5826    0.2267   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6962    0.6058    0.2050 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8377   -0.2052   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816   -1.1981    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1890   -1.4234    2.2953 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2799   -2.0164    0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0849   -1.8641   -0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512   -0.8688   -1.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6462   -0.0609   -1.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2785    1.1702   -2.3269 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7254    2.9922    3.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5282    2.8558    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466    2.8972    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142    1.1473   -0.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8374   -1.6512   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0173   -2.3191   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1611   -1.5857   -1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7706    1.4957    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -2.7997    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9538   -2.5068   -0.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3725   -0.7364   -2.2129 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  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 11  5  1  0
 19 13  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(2,6-Dichloroanilino)-5-hydroxyphenyl]acetic acid	ChEBI
5-Hydroxy diclofenac	ChEBI
5-OH DCF	ChEBI
5-OH-DCF	ChEBI
2-[(2,6-Dichloroanilino)-5-hydroxyphenyl]acetate	Generator

Chemical Formula

C₁₄H₁₁Cl₂NO₃

Average Molecular Weight

312.148

Monoisotopic Molecular Weight

311.011598637

IUPAC Name

2-{2-[(2,6-dichlorophenyl)amino]-5-hydroxyphenyl}acetic acid

Traditional Name

5-hydroxydiclofenac

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:59612 )
phenols (CHEBI:59612 )
secondary amino compound (CHEBI:59612 )
dichlorobenzene (CHEBI:59612 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060542)

Organ

Kidney (HMDB: HMDB0060542)
Liver (HMDB: HMDB0060542)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060542)

Cellular substructure

Cytoplasm (HMDB: HMDB0060542)
Membrane (HMDB: HMDB0060542)

Source

Endogenous

Endogenous (HMDB: HMDB0060542)

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	0.011 g/L	ALOGPS
logP	4.27	ALOGPS
logP	3.96	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.81	ChemAxon
pKa (Strongest Basic)	-0.68	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	29.11 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]+	161.12	30932474
DeepCCS	[M-H]-	158.762	30932474
DeepCCS	[M-2H]-	191.733	30932474
DeepCCS	[M+Na]+	167.213	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.8	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.2	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	159.2	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxydiclofenac	OC(=O)CC1=CC(O)=CC=C1NC1=C(Cl)C=CC=C1Cl	4584.9	Standard polar	33892256
5-Hydroxydiclofenac	OC(=O)CC1=CC(O)=CC=C1NC1=C(Cl)C=CC=C1Cl	2613.7	Standard non polar	33892256
5-Hydroxydiclofenac	OC(=O)CC1=CC(O)=CC=C1NC1=C(Cl)C=CC=C1Cl	2734.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxydiclofenac,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O)=CC=C1NC1=C(Cl)C=CC=C1Cl	2572.3	Semi standard non polar	33892256
5-Hydroxydiclofenac,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(NC2=C(Cl)C=CC=C2Cl)C(CC(=O)O)=C1	2651.6	Semi standard non polar	33892256
5-Hydroxydiclofenac,1TMS,isomer #3	C[Si](C)(C)N(C1=CC=C(O)C=C1CC(=O)O)C1=C(Cl)C=CC=C1Cl	2570.5	Semi standard non polar	33892256
5-Hydroxydiclofenac,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=CC=C1NC1=C(Cl)C=CC=C1Cl	2616.1	Semi standard non polar	33892256
5-Hydroxydiclofenac,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC1=CC(O)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2540.1	Semi standard non polar	33892256
5-Hydroxydiclofenac,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(N(C2=C(Cl)C=CC=C2Cl)[Si](C)(C)C)C(CC(=O)O)=C1	2620.5	Semi standard non polar	33892256
5-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2625.6	Semi standard non polar	33892256
5-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2539.1	Standard non polar	33892256
5-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2853.0	Standard polar	33892256
5-Hydroxydiclofenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O)=CC=C1NC1=C(Cl)C=CC=C1Cl	2858.2	Semi standard non polar	33892256
5-Hydroxydiclofenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(NC2=C(Cl)C=CC=C2Cl)C(CC(=O)O)=C1	2910.0	Semi standard non polar	33892256
5-Hydroxydiclofenac,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1CC(=O)O)C1=C(Cl)C=CC=C1Cl	2853.6	Semi standard non polar	33892256
5-Hydroxydiclofenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1NC1=C(Cl)C=CC=C1Cl	3102.7	Semi standard non polar	33892256
5-Hydroxydiclofenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3063.8	Semi standard non polar	33892256
5-Hydroxydiclofenac,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C2=C(Cl)C=CC=C2Cl)[Si](C)(C)C(C)(C)C)C(CC(=O)O)=C1	3105.2	Semi standard non polar	33892256
5-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3321.0	Semi standard non polar	33892256
5-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3132.1	Standard non polar	33892256
5-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	3118.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxydiclofenac GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0190000000-cf116cb51f2c4c406a5d	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxydiclofenac GC-MS (2 TMS) - 70eV, Positive	splash10-007c-4009100000-7933f4fa6853c842f3fc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-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 - 5-Hydroxydiclofenac 45V, Negative-QTOF	splash10-0159-0390000000-2ff4d3ce7eac53287cb7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 60V, Negative-QTOF	splash10-016u-0960000000-02f0053643d1860893a2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 75V, Negative-QTOF	splash10-00kf-0920000000-2f9d2941b6f1d6f37cba	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 90V, Negative-QTOF	splash10-0006-0900000000-3affcc1bfc04cbb68848	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 45V, Positive-QTOF	splash10-001i-0090000000-deb2303e58035fa2ee72	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 60V, Positive-QTOF	splash10-001i-0090000000-b6389ff0bd5cce02e4dd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 30V, Positive-QTOF	splash10-001i-0090000000-6fa476ecf74bc7f429f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 15V, Positive-QTOF	splash10-0296-0093000000-fc2f20559b89f875d88f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 75V, Positive-QTOF	splash10-001i-0190000000-dc2f23f54946bbcf7cec	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 90V, Positive-QTOF	splash10-001i-0390000000-b576715dfcdcf65ae562	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 30V, Negative-QTOF	splash10-014i-0090000000-7dd5ab9c505b07664834	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5-Hydroxydiclofenac 15V, Negative-QTOF	splash10-014i-0090000000-71f47b9001a1b7202fb9	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 10V, Positive-QTOF	splash10-0006-0092000000-16059496f953548476f9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 20V, Positive-QTOF	splash10-0gb9-0190000000-7fd787f82d1245c488de	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 40V, Positive-QTOF	splash10-05tr-2490000000-017f248cea0034bad7e5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 10V, Negative-QTOF	splash10-03xr-0079000000-4aea9ce6cb25e69dcb42	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 20V, Negative-QTOF	splash10-03xu-0094000000-56578ca28c18eb465ad3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 40V, Negative-QTOF	splash10-0006-3290000000-52f152b87cad5e7a97ac	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 10V, Positive-QTOF	splash10-03xu-0096000000-b02de81978a03e18589c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 20V, Positive-QTOF	splash10-014i-0092000000-b38e77b03db7b00f2a09	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 40V, Positive-QTOF	splash10-008i-0390000000-a507afe603521dbf9fbe	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 10V, Negative-QTOF	splash10-0159-0090000000-ec9bb0c988da08cd85ec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 20V, Negative-QTOF	splash10-001i-3090000000-ccbcb564d1f9bece53e8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxydiclofenac 40V, Negative-QTOF	splash10-001i-9040000000-49f62ead6cdb1692543c	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

3052566

PDB ID

Not Available

ChEBI ID

59612

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-Hydroxydiclofenac (HMDB0060542)

MOL for HMDB0060542 (5-Hydroxydiclofenac)

3D MOL for HMDB0060542 (5-Hydroxydiclofenac)

3D SDF for HMDB0060542 (5-Hydroxydiclofenac)

3D-SDF for HMDB0060542 (5-Hydroxydiclofenac)

PDB for HMDB0060542 (5-Hydroxydiclofenac)

3D PDB for HMDB0060542 (5-Hydroxydiclofenac)

SMILES for HMDB0060542 (5-Hydroxydiclofenac)

INCHI for HMDB0060542 (5-Hydroxydiclofenac)

Structure for HMDB0060542 (5-Hydroxydiclofenac)

3D Structure for HMDB0060542 (5-Hydroxydiclofenac)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra