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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:40 UTC

Update Date

2020-02-26 21:39:19 UTC

HMDB ID

HMDB0013976

Secondary Accession Numbers

HMDB13976

Metabolite Identification

Common Name

3'-Hydroxydiclofenac

Description

3'-Hydroxydiclofenac, also known as 3'-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. 3'-Hydroxydiclofenac is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3'-Hydroxydiclofenac.

Structure

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

HMDB0013976
     RDKit          3D
3'-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.3165   -2.0420   -0.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531   -1.9133    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -3.0019    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6954   -0.5577    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974    0.4299   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    1.3199   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    2.2513   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895    2.2921   -1.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    1.4155   -1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435    0.4870   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -0.4536    0.3939 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093   -0.4665    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520   -1.2354   -0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969   -2.1755   -1.8042 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -1.2854   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -0.5288   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7143    0.2471    0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5298    1.0054    1.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    0.2783    1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    1.2862    2.3115 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2292   -3.0291    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -0.2350    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -0.6555    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0500    1.2481   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426    2.9263   -1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383    3.0437   -2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392    1.4228   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748   -1.1693    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8199   -1.9102   -1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -0.5653   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    1.5711    2.3604 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
 17 18  1  0
 17 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
 16 30  1  0
 18 31  1  0
M  END


  Mrv0541 06191310372D          

 20 21  0  0  0  0            999 V2000
    9.7896   -4.8539    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9316   -4.8539    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.6461   -1.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0751   -1.1413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3607   -4.0289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0751   -2.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0751   -3.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3607   -2.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3607   -4.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7896   -2.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7896   -4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5040   -2.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5040   -3.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0751   -5.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6461   -5.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3607   -1.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0751   -6.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6461   -6.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3607   -6.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7896   -6.5040    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
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013976

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
HYPJZSYXUWYJDG-UHFFFAOYSA-N

> <FORMULA>
C14H11Cl2NO3

> <MOLECULAR_WEIGHT>
312.148

> <EXACT_MASS>
311.011598637

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.95427228271263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2-[(2,6-dichloro-3-hydroxyphenyl)amino]phenyl}acetic acid

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
3.9554439116666664

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.650301261354701

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8231686498283515

> <JCHEM_PKA_STRONGEST_BASIC>
-2.376077200322209

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
77.44230000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3'-hydroxydiclofenac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013976
     RDKit          3D
3'-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.3165   -2.0420   -0.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531   -1.9133    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -3.0019    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6954   -0.5577    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974    0.4299   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    1.3199   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    2.2513   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895    2.2921   -1.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    1.4155   -1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435    0.4870   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -0.4536    0.3939 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093   -0.4665    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520   -1.2354   -0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969   -2.1755   -1.8042 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -1.2854   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -0.5288   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7143    0.2471    0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5298    1.0054    1.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    0.2783    1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    1.2862    2.3115 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2292   -3.0291    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -0.2350    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -0.6555    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0500    1.2481   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426    2.9263   -1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383    3.0437   -2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392    1.4228   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748   -1.1693    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8199   -1.9102   -1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -0.5653   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    1.5711    2.3604 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
 17 18  1  0
 17 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
 16 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      18.274  -9.061   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0      12.939  -9.061   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0      14.273  -2.130   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.940  -2.130   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      15.607  -7.521   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      16.940  -5.211   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.940  -6.751   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.607  -4.441   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.607  -9.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.274  -4.441   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.274  -7.521   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.607  -5.211   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.607  -6.751   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.940  -9.831   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.273  -9.831   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.607  -2.901   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.940 -11.371   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.273 -11.371   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.607 -12.141   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.274 -12.141   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   20                                                  
CONECT   18   15   19                                                       
CONECT   19   17   18                                                       
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0013976
HETATM    1  O1  UNL     1      -2.317  -2.042  -0.881  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.753  -1.913   0.286  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.277  -3.002   0.979  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.695  -0.558   0.913  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.097   0.430  -0.020  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.980   1.320  -0.644  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.455   2.251  -1.513  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.090   2.292  -1.751  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.224   1.416  -1.136  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.743   0.487  -0.270  1.00  0.00           C  
HETATM   11  N1  UNL     1       0.116  -0.454   0.394  1.00  0.00           N  
HETATM   12  C9  UNL     1       1.509  -0.467   0.210  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.052  -1.235  -0.790  1.00  0.00           C  
HETATM   14 CL1  UNL     1       0.997  -2.175  -1.804  1.00  0.00          CL  
HETATM   15  C11 UNL     1       3.430  -1.285  -1.018  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.250  -0.529  -0.199  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.714   0.247   0.808  1.00  0.00           C  
HETATM   18  O3  UNL     1       4.530   1.005   1.630  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.353   0.278   1.012  1.00  0.00           C  
HETATM   20 CL2  UNL     1       1.746   1.286   2.311  1.00  0.00          CL  
HETATM   21  H1  UNL     1      -4.229  -3.029   1.323  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.727  -0.235   1.195  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.064  -0.656   1.836  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.050   1.248  -0.424  1.00  0.00           H  
HETATM   25  H5  UNL     1      -3.143   2.926  -1.983  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.738   3.044  -2.441  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.839   1.423  -1.300  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.275  -1.169   1.044  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.820  -1.910  -1.824  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.335  -0.565  -0.376  1.00  0.00           H  
HETATM   31  H11 UNL     1       4.166   1.571   2.360  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   30
CONECT   17   18   19   19
CONECT   18   31
CONECT   19   20
END

HMDB0013976
     RDKit          3D
3'-Hydroxydiclofenac
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.3165   -2.0420   -0.8812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7531   -1.9133    0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2768   -3.0019    0.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6954   -0.5577    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974    0.4299   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    1.3199   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    2.2513   -1.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895    2.2921   -1.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245    1.4155   -1.1358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435    0.4870   -0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -0.4536    0.3939 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5093   -0.4665    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0520   -1.2354   -0.7900 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969   -2.1755   -1.8042 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -1.2854   -1.0182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2498   -0.5288   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7143    0.2471    0.8084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5298    1.0054    1.6299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3533    0.2783    1.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7460    1.2862    2.3115 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2292   -3.0291    1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -0.2350    1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -0.6555    1.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0500    1.2481   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1426    2.9263   -1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383    3.0437   -2.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8392    1.4228   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748   -1.1693    1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8199   -1.9102   -1.8243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3348   -0.5653   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    1.5711    2.3604 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
 17 18  1  0
 17 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
 16 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(O-(2,6-Dichloro-3-hydroxyanilino)phenyl)acetic acid	ChEBI
3'-OH DCF	ChEBI
(O-(2,6-Dichloro-3-hydroxyanilino)phenyl)acetate	Generator
{2-[(2,6-dichloro-3-hydroxyphenyl)amino]phenyl}acetic acid	HMDB

Chemical Formula

C₁₄H₁₁Cl₂NO₃

Average Molecular Weight

312.148

Monoisotopic Molecular Weight

311.011598637

IUPAC Name

2-{2-[(2,6-dichloro-3-hydroxyphenyl)amino]phenyl}acetic acid

Traditional Name

3'-hydroxydiclofenac

CAS Registry Number

69002-85-3

SMILES

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

InChI Identifier

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

InChI Key

HYPJZSYXUWYJDG-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

2-chlorophenol
2-halophenol
4-halophenol
1,3-dichlorobenzene
4-chlorophenol
Aniline or substituted anilines
Aminophenol
M-aminophenol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl halide
Aryl chloride
Amino acid
Amino acid or derivatives
Carboxylic acid
Secondary amine
Carboxylic acid derivative
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:223792 )
phenols (CHEBI:223792 )
secondary amino compound (CHEBI:223792 )
dichlorobenzene (CHEBI:223792 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013976)

Organ

Liver (HMDB: HMDB0013976)
Kidney (HMDB: HMDB0013976)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Source

Endogenous

Endogenous (HMDB: HMDB0013976)

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	0.01 g/L	ALOGPS
logP	4.23	ALOGPS
logP	3.96	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-2.4	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	28.95 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]+	160.578	30932474
DeepCCS	[M-H]-	158.22	30932474
DeepCCS	[M-2H]-	191.147	30932474
DeepCCS	[M+Na]+	166.671	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	160.9	32859911
AllCCS	[M+NH4]+	167.4	32859911
AllCCS	[M+Na]+	168.3	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	159.2	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.48 minutes	32390414
Predicted by Siyang on May 30, 2022	14.772 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.64 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2024.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	406.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	154.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	132.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	750.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	624.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	226.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1253.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	499.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1492.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	451.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	214.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	90.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3'-Hydroxydiclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C(O)=CC=C1Cl	4524.3	Standard polar	33892256
3'-Hydroxydiclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C(O)=CC=C1Cl	2598.1	Standard non polar	33892256
3'-Hydroxydiclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C(O)=CC=C1Cl	2555.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3'-Hydroxydiclofenac,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC(O)=C1Cl	2499.1	Semi standard non polar	33892256
3'-Hydroxydiclofenac,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(Cl)C(NC2=CC=CC=C2CC(=O)O)=C1Cl	2559.8	Semi standard non polar	33892256
3'-Hydroxydiclofenac,1TMS,isomer #3	C[Si](C)(C)N(C1=CC=CC=C1CC(=O)O)C1=C(Cl)C=CC(O)=C1Cl	2467.4	Semi standard non polar	33892256
3'-Hydroxydiclofenac,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC(O[Si](C)(C)C)=C1Cl	2544.5	Semi standard non polar	33892256
3'-Hydroxydiclofenac,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O)=C1Cl)[Si](C)(C)C	2438.6	Semi standard non polar	33892256
3'-Hydroxydiclofenac,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(Cl)C(N(C2=CC=CC=C2CC(=O)O)[Si](C)(C)C)=C1Cl	2520.4	Semi standard non polar	33892256
3'-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O[Si](C)(C)C)=C1Cl)[Si](C)(C)C	2531.7	Semi standard non polar	33892256
3'-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O[Si](C)(C)C)=C1Cl)[Si](C)(C)C	2491.5	Standard non polar	33892256
3'-Hydroxydiclofenac,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O[Si](C)(C)C)=C1Cl)[Si](C)(C)C	2804.4	Standard polar	33892256
3'-Hydroxydiclofenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC(O)=C1Cl	2745.7	Semi standard non polar	33892256
3'-Hydroxydiclofenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C(NC2=CC=CC=C2CC(=O)O)=C1Cl	2811.3	Semi standard non polar	33892256
3'-Hydroxydiclofenac,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1CC(=O)O)C1=C(Cl)C=CC(O)=C1Cl	2716.2	Semi standard non polar	33892256
3'-Hydroxydiclofenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl	3006.7	Semi standard non polar	33892256
3'-Hydroxydiclofenac,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O)=C1Cl)[Si](C)(C)C(C)(C)C	2909.8	Semi standard non polar	33892256
3'-Hydroxydiclofenac,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C(N(C2=CC=CC=C2CC(=O)O)[Si](C)(C)C(C)(C)C)=C1Cl	2976.0	Semi standard non polar	33892256
3'-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl)[Si](C)(C)C(C)(C)C	3190.4	Semi standard non polar	33892256
3'-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl)[Si](C)(C)C(C)(C)C	3069.6	Standard non polar	33892256
3'-Hydroxydiclofenac,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC(O[Si](C)(C)C(C)(C)C)=C1Cl)[Si](C)(C)C(C)(C)C	3087.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-Hydroxydiclofenac GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0090000000-197a5fc102fdc4aa00d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-Hydroxydiclofenac GC-MS (2 TMS) - 70eV, Positive	splash10-007c-5009100000-cd7ec6a2155c63ebdc34	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-Hydroxydiclofenac GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3'-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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 10V, Positive-QTOF	splash10-03dl-0096000000-71b5c717ecdab0975def	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 20V, Positive-QTOF	splash10-014i-0090000000-ec15776c577b3d3f2ad9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 40V, Positive-QTOF	splash10-0gdl-3390000000-4c3ec79ada96679d9bcb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 10V, Negative-QTOF	splash10-03xr-0069000000-27626e3add4a5d3c2d0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 20V, Negative-QTOF	splash10-03xr-0094000000-7cc2ceeb128118670540	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 40V, Negative-QTOF	splash10-05al-2190000000-a7545194e7d6cf6c147f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 10V, Positive-QTOF	splash10-02tc-0094000000-91af6ee0aa95f046b9f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 20V, Positive-QTOF	splash10-014i-0091000000-6dfac3ef5b706c687622	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 40V, Positive-QTOF	splash10-014r-1790000000-16dcbcfe0b25c6d1ad51	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 10V, Negative-QTOF	splash10-014i-0090000000-f9e3a0eb65477e2b7d3e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 20V, Negative-QTOF	splash10-001i-2090000000-5c41ffdd2da16f199698	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3'-Hydroxydiclofenac 40V, Negative-QTOF	splash10-001i-1090000000-dac65c4ca0c2f44c8d01	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

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	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

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

100604

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

112230

PDB ID

Not Available

ChEBI ID

223792

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 3'-Hydroxydiclofenac (HMDB0013976)

MOL for HMDB0013976 (3'-Hydroxydiclofenac)

3D MOL for HMDB0013976 (3'-Hydroxydiclofenac)

3D SDF for HMDB0013976 (3'-Hydroxydiclofenac)

3D-SDF for HMDB0013976 (3'-Hydroxydiclofenac)

PDB for HMDB0013976 (3'-Hydroxydiclofenac)

3D PDB for HMDB0013976 (3'-Hydroxydiclofenac)

SMILES for HMDB0013976 (3'-Hydroxydiclofenac)

INCHI for HMDB0013976 (3'-Hydroxydiclofenac)

Structure for HMDB0013976 (3'-Hydroxydiclofenac)

3D Structure for HMDB0013976 (3'-Hydroxydiclofenac)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra