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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3)transporters (2) Show 5 proteins XML

enzymes (3)transporters (2) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015074

Secondary Accession Numbers

HMDB15074

Metabolite Identification

Common Name

Meclofenamic acid

Description

Meclofenamic acid is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis. [PubChem]The mode of action, like that of other nonsteroidal anti-inflammatory agents, is not known. Therapeutic action does not result from pituitary-adrenal stimulation. In animal studies, meclofenamic acid was found to inhibit prostaglandin synthesis and to compete for binding at the prostaglandin receptor site. In vitro meclofenamic acid was found to be an inhibitor of human leukocyte 5-lipoxygenase activity. These properties may be responsible for the anti-inflammatory action of meclofenamic acid. There is no evidence that meclofenamic acid alters the course of the underlying disease.

Structure

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

HMDB0015074
     RDKit          3D
Meclofenamic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7850    1.1233    1.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966    0.3468    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -0.8081    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8229   -1.5670   -0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.1680   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776   -2.1561   -2.1118 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0053   -0.0168   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145    0.3810   -0.8520 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4741   -0.0608   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2732   -0.8935    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.3477    1.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121   -0.9712    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7949   -0.1601    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    0.3370   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9823    1.1936   -1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.4559   -1.9843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818    1.7615   -2.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294    0.7060    0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    2.1775    1.1581 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2857    2.0347    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    0.5213    2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7762    1.4489    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5189   -1.1255    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -2.4814   -0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397    0.9919   -1.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.1498    1.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -1.9867    2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405   -1.3570    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.1147   -0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    2.6556   -3.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18 19  1  0
 18  2  1  0
 14  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
M  END

939
  Mrv0541 02231215072D          

 19 20  0  0  0  0            999 V2000
    1.6500   -0.9529    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.9529    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.3472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2 11  1  0  0  0  0
  3 19  1  0  0  0  0
  4 19  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  2  0  0  0  0
  7 10  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  2  0  0  0  0
  8 12  1  0  0  0  0
  8 16  1  0  0  0  0
 10 15  2  0  0  0  0
 10 19  1  0  0  0  0
 11 14  1  0  0  0  0
 12 14  2  0  0  0  0
 13 17  1  0  0  0  0
 15 18  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015074

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)

> <INCHI_KEY>
SBDNJUWAMKYJOX-UHFFFAOYSA-N

> <FORMULA>
C14H11Cl2NO2

> <MOLECULAR_WEIGHT>
296.149

> <EXACT_MASS>
295.016684015

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.43958493021026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
6.092265241333333

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.052354040679607

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.786930003597555

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6275604973318707

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
76.45120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
meclofenamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015074
     RDKit          3D
Meclofenamic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7850    1.1233    1.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966    0.3468    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -0.8081    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8229   -1.5670   -0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.1680   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776   -2.1561   -2.1118 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0053   -0.0168   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145    0.3810   -0.8520 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4741   -0.0608   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2732   -0.8935    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.3477    1.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121   -0.9712    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7949   -0.1601    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    0.3370   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9823    1.1936   -1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.4559   -1.9843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818    1.7615   -2.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294    0.7060    0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    2.1775    1.1581 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2857    2.0347    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    0.5213    2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7762    1.4489    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5189   -1.1255    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -2.4814   -0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397    0.9919   -1.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.1498    1.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -1.9867    2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405   -1.3570    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.1147   -0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    2.6556   -3.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18 19  1  0
 18  2  1  0
 14  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 939                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -1.779   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       8.415  -1.779   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       5.748   4.381   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414   2.071   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.748  -0.239   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.748  -1.779   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -4.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -2.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   2.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -2.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -4.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -0.239   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   2.841   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -4.859   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   0.531   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   2.071   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748   2.841   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    6    7                                                       
CONECT    6    5    9   11                                                  
CONECT    7    5   10   13                                                  
CONECT    8    9   12   16                                                  
CONECT    9    1    6    8                                                  
CONECT   10    7   15   19                                                  
CONECT   11    2    6   14                                                  
CONECT   12    8   14                                                       
CONECT   13    7   17                                                       
CONECT   14   11   12                                                       
CONECT   15   10   18                                                       
CONECT   16    8                                                            
CONECT   17   13   18                                                       
CONECT   18   15   17                                                       
CONECT   19    3    4   10                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015074
HETATM    1  C1  UNL     1       3.785   1.123   1.879  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.997   0.347   0.906  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.522  -0.808   0.372  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.823  -1.567  -0.541  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.548  -1.168  -0.945  1.00  0.00           C  
HETATM    6 CL1  UNL     1       0.678  -2.156  -2.112  1.00  0.00          CL  
HETATM    7  C6  UNL     1       1.005  -0.017  -0.423  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.314   0.381  -0.852  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.474  -0.061  -0.160  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.273  -0.894   0.949  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.336  -1.348   1.650  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.612  -0.971   1.246  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.795  -0.160   0.166  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.718   0.337  -0.595  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.982   1.194  -1.730  1.00  0.00           C  
HETATM   16  O1  UNL     1      -4.200   1.456  -1.984  1.00  0.00           O  
HETATM   17  O2  UNL     1      -2.082   1.761  -2.572  1.00  0.00           O  
HETATM   18  C14 UNL     1       1.729   0.706   0.478  1.00  0.00           C  
HETATM   19 CL2  UNL     1       1.060   2.177   1.158  1.00  0.00          CL  
HETATM   20  H1  UNL     1       3.286   2.035   2.207  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.014   0.521   2.787  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.776   1.449   1.449  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.519  -1.125   0.684  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.229  -2.481  -0.969  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.340   0.992  -1.676  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.231  -1.150   1.209  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.179  -1.987   2.501  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.441  -1.357   1.836  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.790   0.115  -0.124  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.203   2.656  -3.005  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   18
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6    7
CONECT    7    8   18   18
CONECT    8    9   25
CONECT    9   10   10   14
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15
CONECT   15   16   16   17
CONECT   17   30
CONECT   18   19
END

HMDB0015074
     RDKit          3D
Meclofenamic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7850    1.1233    1.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9966    0.3468    0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5216   -0.8081    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8229   -1.5670   -0.5408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.1680   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776   -2.1561   -2.1118 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0053   -0.0168   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145    0.3810   -0.8520 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4741   -0.0608   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2732   -0.8935    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3358   -1.3477    1.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121   -0.9712    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7949   -0.1601    0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7176    0.3370   -0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9823    1.1936   -1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.4559   -1.9843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818    1.7615   -2.5716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294    0.7060    0.4778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0603    2.1775    1.1581 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2857    2.0347    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    0.5213    2.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7762    1.4489    1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5189   -1.1255    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2291   -2.4814   -0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3397    0.9919   -1.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312   -1.1498    1.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -1.9867    2.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4405   -1.3570    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7901    0.1147   -0.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    2.6556   -3.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18 19  1  0
 18  2  1  0
 14  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acide meclofenamique	ChEBI
Acido meclofenamico	ChEBI
Acidum meclofenamicum	ChEBI
CI-583	ChEBI
INF 4668	ChEBI
N-(2,6-Dichloro-3-methylphenyl)anthranilic acid	ChEBI
N-(2,6-Dichloro-m-tolyl)anthranilic acid	ChEBI
N-(3-Methyl-2,6-dichlorophenyl)anthranilic acid	ChEBI
N-(2,6-Dichloro-3-methylphenyl)anthranilate	Generator
N-(2,6-Dichloro-m-tolyl)anthranilate	Generator
N-(3-Methyl-2,6-dichlorophenyl)anthranilate	Generator
Meclofenamate	Generator
Meclomen (free acid)	HMDB
Meclophenamic acid	HMDB
Meclofenamate sodium	HMDB
Meclomen	HMDB
Sodium, meclofenamate	HMDB
Meclofenamate, sodium	HMDB
Sodium meclofenamate	HMDB
Acid, meclofenamic	HMDB
Parke davis brand OF sodium meclofenamate	HMDB
Anhydrous, meclofenamate sodium	HMDB
Benzoic acid, 2-((2,6-dichloro-3-methylphenyl)amino)-, monosodium salt, monohydrate	HMDB
Meclofenamate sodium monohydrate	HMDB
Meclofenamate sodium anhydrous	HMDB

Chemical Formula

C₁₄H₁₁Cl₂NO₂

Average Molecular Weight

296.149

Monoisotopic Molecular Weight

295.016684015

IUPAC Name

2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid

Traditional Name

meclofenamic acid

CAS Registry Number

644-62-2

SMILES

CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1

InChI Identifier

InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)

InChI Key

SBDNJUWAMKYJOX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzoic acids

Alternative Parents

Substituents

Aminobenzoic acid
Benzoic acid
Benzoyl
1,3-dichlorobenzene
Aniline or substituted anilines
Aminotoluene
Toluene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Vinylogous amide
Amino acid
Amino acid or derivatives
Monocarboxylic acid or derivatives
Secondary amine
Carboxylic acid
Carboxylic acid derivative
Organohalogen compound
Organooxygen compound
Organic oxide
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organochloride
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:6710 )
secondary amino compound (CHEBI:6710 )
aminobenzoic acid (CHEBI:6710 )

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

Cytoplasm (HMDB: HMDB0015074)
Membrane (HMDB: HMDB0015074)

Source

Exogenous

Exogenous (HMDB: HMDB0015074)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	257 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0037 g/L	Not Available
LogP	5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0037 g/L	ALOGPS
logP	5.11	ALOGPS
logP	6.09	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.79	ChemAxon
pKa (Strongest Basic)	-3.6	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	3	ChemAxon
Refractivity	76.45 m³·mol⁻¹	ChemAxon
Polarizability	28.44 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	161.33	30932474
DeepCCS	[M-H]-	158.972	30932474
DeepCCS	[M-2H]-	191.858	30932474
DeepCCS	[M+Na]+	167.423	30932474
AllCCS	[M+H]+	160.4	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.7	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	155.0	32859911
AllCCS	[M+Na-2H]-	154.3	32859911
AllCCS	[M+HCOO]-	153.6	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.	7.85 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1588 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2461.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	571.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	361.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	268.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	891.0 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	837.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	390.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1563.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	605.0 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	1745.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	516.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	502.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	560.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	316.4 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	24.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Meclofenamic acid	CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1	3846.3	Standard polar	33892256
Meclofenamic acid	CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1	2379.6	Standard non polar	33892256
Meclofenamic acid	CC1=C(Cl)C(NC2=CC=CC=C2C(O)=O)=C(Cl)C=C1	2393.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Meclofenamic acid,1TMS,isomer #1	CC1=CC=C(Cl)C(NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=C1Cl	2364.9	Semi standard non polar	33892256
Meclofenamic acid,1TMS,isomer #2	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=C1Cl	2301.7	Semi standard non polar	33892256
Meclofenamic acid,2TMS,isomer #1	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1Cl	2301.5	Semi standard non polar	33892256
Meclofenamic acid,2TMS,isomer #1	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1Cl	2364.0	Standard non polar	33892256
Meclofenamic acid,2TMS,isomer #1	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1Cl	2713.2	Standard polar	33892256
Meclofenamic acid,1TBDMS,isomer #1	CC1=CC=C(Cl)C(NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=C1Cl	2590.8	Semi standard non polar	33892256
Meclofenamic acid,1TBDMS,isomer #2	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=C1Cl	2543.8	Semi standard non polar	33892256
Meclofenamic acid,2TBDMS,isomer #1	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1Cl	2779.7	Semi standard non polar	33892256
Meclofenamic acid,2TBDMS,isomer #1	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1Cl	2744.7	Standard non polar	33892256
Meclofenamic acid,2TBDMS,isomer #1	CC1=CC=C(Cl)C(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1Cl	2932.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Meclofenamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f92-0190000000-ce5bf5fd48806b5fbdf3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meclofenamic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0kmj-5139000000-a73b6d1b9aebb773ea60	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meclofenamic acid 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 - Meclofenamic acid LC-ESI-QFT , negative-QTOF	splash10-0006-0090000000-dc6d0aaa7ee199899830	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , negative-QTOF	splash10-052f-0090000000-4f2a28033e59bab0257a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , negative-QTOF	splash10-03di-0190000000-b6abcaff657bfa67b599	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , negative-QTOF	splash10-03fr-0690000000-eccbe792d08156c89c39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , negative-QTOF	splash10-004i-0920000000-fdcf8eff9ac77cf86d5b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , negative-QTOF	splash10-004i-0900000000-77140947d50a131a9be6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , negative-QTOF	splash10-004i-0900000000-5d2a4942eea2a2d2f252	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-004i-0090000000-85032b374ac40bac481a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-004l-0090000000-a2cbafbde1150bf5812e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-0006-0090000000-47d80abc4f95a2c5ef4c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-0006-0090000000-cfa40a800c6a52f6a264	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-0006-0290000000-2e34cb2892f6263b39fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-0563-0980000000-54fb4017b6a67acb639b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-004i-0910000000-26fefd3e49fc0ba3e36e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-0fb9-1900000000-448908b1e79c92a656d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid LC-ESI-QFT , positive-QTOF	splash10-0fb9-2900000000-71b13766bf05541800b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid 60V, Negative-QTOF	splash10-03fr-0690000000-00efb213d800845550a8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid 75V, Negative-QTOF	splash10-004i-0920000000-fdcf8eff9ac77cf86d5b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meclofenamic acid 15V, Positive-QTOF	splash10-004i-0090000000-85032b374ac40bac481a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenamic acid 10V, Positive-QTOF	splash10-0002-0090000000-499829b8629f7135db60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenamic acid 20V, Positive-QTOF	splash10-0ufr-0090000000-bce444b767c6cc91af25	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenamic acid 40V, Positive-QTOF	splash10-0udi-3090000000-9eedeb81aec059f12e40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenamic acid 10V, Negative-QTOF	splash10-0udl-0090000000-de90eca3751b173b8e3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenamic acid 20V, Negative-QTOF	splash10-0udi-0090000000-d3726ae14682e4737b66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meclofenamic acid 40V, Negative-QTOF	splash10-0w2c-1190000000-9bc69c7e4771495d751a	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00939	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00939	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00939

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3897

KEGG Compound ID

C07117

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meclofenamic_acid

METLIN ID

Not Available

PubChem Compound

4037

PDB ID

Not Available

ChEBI ID

6710

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

Enzymes

Enzyme Details

1. Arachidonate 5-lipoxygenase

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

References

Yu XY, Hubbard W, Spannhake EW: Inhibition of canine tracheal smooth muscle by mediators from cultured bronchial epithelial cells. Am J Physiol. 1992 Feb;262(2 Pt 1):L229-34. [PubMed:1539679 ]
Boctor AM, Eickholt M, Pugsley TA: Meclofenamate sodium is an inhibitor of both the 5-lipoxygenase and cyclooxygenase pathways of the arachidonic acid cascade in vitro. Prostaglandins Leukot Med. 1986 Aug;23(2-3):229-38. [PubMed:3020588 ]

Enzyme Details

2. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Kalgutkar AS, Crews BC, Rowlinson SW, Marnett AB, Kozak KR, Remmel RP, Marnett LJ: Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):925-30. [PubMed:10639181 ]
Traupe T, Lang M, Goettsch W, Munter K, Morawietz H, Vetter W, Barton M: Obesity increases prostanoid-mediated vasoconstriction and vascular thromboxane receptor gene expression. J Hypertens. 2002 Nov;20(11):2239-45. [PubMed:12409963 ]
Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
Narsinghani T, Chaturvedi SC: QSAR analysis of meclofenamic acid analogues as selective COX-2 inhibitors. Bioorg Med Chem Lett. 2006 Jan 15;16(2):461-8. Epub 2005 Nov 14. [PubMed:16290292 ]
Smith WL, Meade EA, DeWitt DL: Interactions of PGH synthase isozymes-1 and -2 with NSAIDs. Ann N Y Acad Sci. 1994 Nov 15;744:50-7. [PubMed:7825862 ]

Enzyme Details

3. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Perez-Vizcaino F, Lopez-Lopez JG, Santiago R, Cogolludo A, Zaragoza-Arnaez F, Moreno L, Alonso MJ, Salaices M, Tamargo J: Postnatal maturation in nitric oxide-induced pulmonary artery relaxation involving cyclooxygenase-1 activity. Am J Physiol Lung Cell Mol Physiol. 2002 Oct;283(4):L839-48. [PubMed:12225961 ]
Shiels IA, Whitehouse MW: Lyprinol: anti-inflammatory and uterine-relaxant activities in rats, with special reference to a model for dysmenorrhoea. Allerg Immunol (Paris). 2000 Sep;32(7):279-83. [PubMed:11094641 ]
Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
Kalgutkar AS, Crews BC, Rowlinson SW, Marnett AB, Kozak KR, Remmel RP, Marnett LJ: Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci U S A. 2000 Jan 18;97(2):925-30. [PubMed:10639181 ]
Meade EA, Smith WL, DeWitt DL: Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J Biol Chem. 1993 Mar 25;268(9):6610-4. [PubMed:8454631 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1C1

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

References

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

Enzyme Details

2. Solute carrier family 22 member 6

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

References

Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]

Showing metabocard for Meclofenamic acid (HMDB0015074)

MOL for HMDB0015074 (Meclofenamic acid)

3D MOL for HMDB0015074 (Meclofenamic acid)

3D SDF for HMDB0015074 (Meclofenamic acid)

3D-SDF for HMDB0015074 (Meclofenamic acid)

PDB for HMDB0015074 (Meclofenamic acid)

3D PDB for HMDB0015074 (Meclofenamic acid)

SMILES for HMDB0015074 (Meclofenamic acid)

INCHI for HMDB0015074 (Meclofenamic acid)

Structure for HMDB0015074 (Meclofenamic acid)

3D Structure for HMDB0015074 (Meclofenamic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

Transporters

References

References