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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014724

Secondary Accession Numbers

HMDB14724

Metabolite Identification

Common Name

Diclofenac

Description

Diclofenac is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt. [PubChem]The antiinflammatory effects of diclofenac are believed to be due to inhibition of both leukocyte migration and the enzyme cylooxygenase (COX-1 and COX-2), leading to the peripheral inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, inhibition of their synthesis is responsible for the analgesic effects of diclofenac. Antipyretic effects may be due to action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat dissipation.

Structure

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

HMDB0014724
     RDKit          3D
Diclofenac
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.2079   -0.2139    2.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630   -1.2390    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003   -2.3349    2.1978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173   -1.2810    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200   -0.0068   -0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8625   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    2.0307   -1.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0866    2.3280   -1.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032    1.4339   -1.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6787    0.2640   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -0.6252    0.0806 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383   -0.3861    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -0.8052   -0.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028   -1.6407   -2.2183 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8564   -0.5511   -0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023    0.1104    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    0.5287    1.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    0.2759    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.7977    2.4949 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -3.2776    1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -2.1430   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650   -1.4519   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    0.6687   -1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1229    2.7393   -2.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950    3.2406   -2.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643    1.6933   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1264   -1.5152    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5203   -0.8779   -1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575    0.3223    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524    1.0534    2.2016 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  2  0
 18 19  1  0
 10  5  1  0
 18 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

586
  Mrv0541 02231214472D          

 19 20  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
  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
M  END
> <DATABASE_ID>
HMDB0014724

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)

> <INCHI_KEY>
DCOPUUMXTXDBNB-UHFFFAOYSA-N

> <FORMULA>
C14H11Cl2NO2

> <MOLECULAR_WEIGHT>
296.149

> <EXACT_MASS>
295.016684015

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.93167870508987

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
4.259009233333334

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.40187487777428

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.995651870366132

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0760497458522584

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
75.46140000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
diclofenac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014724
     RDKit          3D
Diclofenac
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.2079   -0.2139    2.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630   -1.2390    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003   -2.3349    2.1978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173   -1.2810    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200   -0.0068   -0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8625   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    2.0307   -1.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0866    2.3280   -1.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032    1.4339   -1.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6787    0.2640   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -0.6252    0.0806 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383   -0.3861    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -0.8052   -0.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028   -1.6407   -2.2183 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8564   -0.5511   -0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023    0.1104    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    0.5287    1.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    0.2759    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.7977    2.4949 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -3.2776    1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -2.1430   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650   -1.4519   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    0.6687   -1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1229    2.7393   -2.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950    3.2406   -2.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643    1.6933   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1264   -1.5152    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5203   -0.8779   -1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575    0.3223    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524    1.0534    2.2016 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  2  0
 18 19  1  0
 10  5  1  0
 18 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 586                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-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
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                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014724
HETATM    1  O1  UNL     1      -2.208  -0.214   2.093  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.563  -1.239   1.480  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.000  -2.335   2.198  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.517  -1.281   0.023  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.020  -0.007  -0.561  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.932   0.863  -1.138  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.433   2.031  -1.669  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.087   2.328  -1.630  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.203   1.434  -1.045  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.679   0.264  -0.510  1.00  0.00           C  
HETATM   11  N1  UNL     1       0.244  -0.625   0.081  1.00  0.00           N  
HETATM   12  C9  UNL     1       1.638  -0.386   0.152  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.489  -0.805  -0.853  1.00  0.00           C  
HETATM   14 CL1  UNL     1       1.803  -1.641  -2.218  1.00  0.00          CL  
HETATM   15  C11 UNL     1       3.856  -0.551  -0.749  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.402   0.110   0.332  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.541   0.529   1.339  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.169   0.276   1.238  1.00  0.00           C  
HETATM   19 CL2  UNL     1       1.089   0.798   2.495  1.00  0.00          CL  
HETATM   20  H1  UNL     1      -2.988  -3.278   1.817  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.894  -2.143  -0.294  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.565  -1.452  -0.342  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.994   0.669  -1.189  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.123   2.739  -2.132  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.695   3.241  -2.045  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.864   1.693  -1.026  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.126  -1.515   0.490  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.520  -0.878  -1.534  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.457   0.322   0.441  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.952   1.053   2.202  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6    6   10
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   11
CONECT   11   12   27
CONECT   12   13   13   18
CONECT   13   14   15
CONECT   15   16   16   28
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19
END

HMDB0014724
     RDKit          3D
Diclofenac
 30 31  0  0  0  0  0  0  0  0999 V2000
   -2.2079   -0.2139    2.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630   -1.2390    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003   -2.3349    2.1978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173   -1.2810    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200   -0.0068   -0.5614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319    0.8625   -1.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4325    2.0307   -1.6687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0866    2.3280   -1.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2032    1.4339   -1.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6787    0.2640   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440   -0.6252    0.0806 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6383   -0.3861    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890   -0.8052   -0.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8028   -1.6407   -2.2183 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8564   -0.5511   -0.7486 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4023    0.1104    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    0.5287    1.3385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    0.2759    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0888    0.7977    2.4949 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -3.2776    1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8942   -2.1430   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650   -1.4519   -0.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9936    0.6687   -1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1229    2.7393   -2.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950    3.2406   -2.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8643    1.6933   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1264   -1.5152    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5203   -0.8779   -1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4575    0.3223    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524    1.0534    2.2016 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  2  0
 18 19  1  0
 10  5  1  0
 18 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 11 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-((2,6-Dichlorophenyl)amino)benzeneacetic acid	ChEBI
[2-(2,6-Dichloroanilino)phenyl]acetic acid	ChEBI
Diclofenac acid	ChEBI
Diclofenaco	ChEBI
Diclofenacum	ChEBI
Diclofenamic acid	ChEBI
Solaraze	Kegg
Zorvolex	Kegg
2-((2,6-Dichlorophenyl)amino)benzeneacetate	Generator
[2-(2,6-Dichloroanilino)phenyl]acetate	Generator
Diclofenamate	Generator
Diclofenac potassium	HMDB
ISV-205	HMDB
Novapirina	HMDB
Orthofen	HMDB
Ortofen	HMDB
Dichlofenal	HMDB
Diclonate p	HMDB
Dicrofenac	HMDB
Feloran	HMDB
Orthophen	HMDB
Sodium diclofenac	HMDB
Voltaren	HMDB
Voltarol	HMDB
Diclofenac sodium	HMDB
Diclophenac	HMDB
SR 38	HMDB
Diclofenac, sodium	HMDB
SR-38	HMDB

Chemical Formula

C₁₄H₁₁Cl₂NO₂

Average Molecular Weight

296.149

Monoisotopic Molecular Weight

295.016684015

IUPAC Name

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

Traditional Name

diclofenac

CAS Registry Number

15307-86-5

SMILES

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

InChI Identifier

InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)

InChI Key

DCOPUUMXTXDBNB-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

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:47381 )
secondary amino compound (CHEBI:47381 )
dichlorobenzene (CHEBI:47381 )
aromatic amine (CHEBI:47381 )
amino acid (CHEBI:47381 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014724)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Diclofenac Action Pathway (PathBank: SMP0000093)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	283 - 285 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0045 g/L	Not Available
LogP	3.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	157.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0045 g/L	ALOGPS
logP	4.98	ALOGPS
logP	4.26	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.46 m³·mol⁻¹	ChemAxon
Polarizability	27.93 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]+	157.829	30932474
DeepCCS	[M-H]-	155.471	30932474
DeepCCS	[M-2H]-	188.416	30932474
DeepCCS	[M+Na]+	163.922	30932474
AllCCS	[M+H]+	161.1	32859911
AllCCS	[M+H-H2O]+	157.6	32859911
AllCCS	[M+NH4]+	164.3	32859911
AllCCS	[M+Na]+	165.3	32859911
AllCCS	[M-H]-	157.3	32859911
AllCCS	[M+Na-2H]-	156.7	32859911
AllCCS	[M+HCOO]-	156.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	4059.2	Standard polar	33892256
Diclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	2393.9	Standard non polar	33892256
Diclofenac	OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	2372.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diclofenac,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	2318.5	Semi standard non polar	33892256
Diclofenac,1TMS,isomer #2	C[Si](C)(C)N(C1=CC=CC=C1CC(=O)O)C1=C(Cl)C=CC=C1Cl	2336.9	Semi standard non polar	33892256
Diclofenac,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2309.3	Semi standard non polar	33892256
Diclofenac,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2336.0	Standard non polar	33892256
Diclofenac,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C	2802.9	Standard polar	33892256
Diclofenac,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl	2562.4	Semi standard non polar	33892256
Diclofenac,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1CC(=O)O)C1=C(Cl)C=CC=C1Cl	2579.9	Semi standard non polar	33892256
Diclofenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2791.2	Semi standard non polar	33892256
Diclofenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2764.7	Standard non polar	33892256
Diclofenac,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=CC=C1N(C1=C(Cl)C=CC=C1Cl)[Si](C)(C)C(C)(C)C	2974.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Diclofenac EI-B (Non-derivatized)	splash10-03xv-3390000000-cd724f772f8ff3648856	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Diclofenac EI-B (Non-derivatized)	splash10-03xv-3390000000-cd724f772f8ff3648856	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diclofenac GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4290000000-1eb3d1011ce45deff962	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diclofenac GC-MS (1 TMS) - 70eV, Positive	splash10-0udi-5090000000-00fc73f6f5cfbb7052d0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diclofenac GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03xv-1290000000-8fb3ce6f68fc69b5218e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-1d8a04523a99bbdd0f79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-55cf6c5663edc2bce2af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-0257da659c18c3020ebe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0w29-0090000000-eba79744370d30689f45	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-03fr-0890000000-0870dbb742038ce60ba1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-004i-0900000000-a9b9817f70b72a327169	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-58aba74cf5c165b0b3e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-380ce6ec03fa880c2fee	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0w29-0090000000-1c764b23643b9731a5a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0ik9-0290000000-5d59b6e5d4465a9e6493	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-004i-0900000000-483b1ac79bbfb8f591c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0fb9-0950000000-4192d5344ed223d4bfd6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-1d8a04523a99bbdd0f79	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-QQ , negative-QTOF	splash10-0006-0090000000-d28bb6688b1bce51bfce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-QQ , negative-QTOF	splash10-0udi-0090000000-33332a8dbce37d5ad759	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-QQ , negative-QTOF	splash10-0udi-1490000000-f1c9ca0a1b924dba188e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-QQ , negative-QTOF	splash10-004i-4910000000-4c58f3f969da3d86e23c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-QQ , negative-QTOF	splash10-00or-7900000000-3b2e03ec45a0b642cb4d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Diclofenac LC-ESI-ITFT , negative-QTOF	splash10-0udi-0390000000-247401e4df8c88d9f260	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diclofenac 10V, Positive-QTOF	splash10-002b-0090000000-a3ff3ed470584d694666	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diclofenac 20V, Positive-QTOF	splash10-0udi-0090000000-29ed9f5d1fb4bcf6262b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diclofenac 40V, Positive-QTOF	splash10-0ug0-4290000000-a381ef55b23a6901b44a	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diclofenac 10V, Negative-QTOF	splash10-0f6x-0090000000-00e8c59bbd02e8ef68e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diclofenac 20V, Negative-QTOF	splash10-0f6x-0090000000-dae419eef17327b624d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diclofenac 40V, Negative-QTOF	splash10-0kc6-4390000000-a037e01b7793bd48c1d5	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00586	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00586	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00586

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2925

KEGG Compound ID

C01690

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diclofenac

METLIN ID

Not Available

PubChem Compound

3033

PDB ID

DIF

ChEBI ID

47381

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

FitzGerald GA, Patrono C: The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med. 2001 Aug 9;345(6):433-42. [PubMed:11496855 ]
Brater DC: Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage. 2002 Apr;23(4 Suppl):S15-20; discussion S21-3. [PubMed:11992745 ]
Solomon DH, Avorn J, Sturmer T, Glynn RJ, Mogun H, Schneeweiss S: Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum. 2006 May;54(5):1378-89. [PubMed:16645966 ]
Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [PubMed:16740558 ]
Graham DJ: COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA. 2006 Oct 4;296(13):1653-6. Epub 2006 Sep 12. [PubMed:16968830 ]
Gan TJ: Diclofenac: an update on its mechanism of action and safety profile. Curr Med Res Opin. 2010 Jul;26(7):1715-31. doi: 10.1185/03007995.2010.486301. [PubMed:20470236 ]
Sigma Aldrich [Link]

Showing metabocard for Diclofenac (HMDB0014724)

MOL for HMDB0014724 (Diclofenac)

3D MOL for HMDB0014724 (Diclofenac)

3D SDF for HMDB0014724 (Diclofenac)

3D-SDF for HMDB0014724 (Diclofenac)

PDB for HMDB0014724 (Diclofenac)

3D PDB for HMDB0014724 (Diclofenac)

SMILES for HMDB0014724 (Diclofenac)

INCHI for HMDB0014724 (Diclofenac)

Structure for HMDB0014724 (Diclofenac)

3D Structure for HMDB0014724 (Diclofenac)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra