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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014922

Secondary Accession Numbers

HMDB14922

Metabolite Identification

Common Name

Mefenamic acid

Description

Mefenamic acid is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase. [PubChem]Mefenamic acid binds the prostaglandin synthetase receptors COX-1 and COX-2, inhibiting the action of prostaglandin synthetase. As these receptors have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity, the symptoms of pain are temporarily reduced.

Structure

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

HMDB0014922
     RDKit          3D
Mefenamic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.5244    0.0811    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218   -0.4171   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -1.5271   -0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828   -2.0134   -1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -1.3892   -1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.2879   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    0.4084    0.1040 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -0.0935    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845   -1.4360    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -1.9235    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254   -1.0296    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    0.3073   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757    0.7734   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6104    2.2164   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    2.7957   -0.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531    3.0247   -0.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    0.1691    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0196    1.3584    1.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6460   -0.0947    1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3645   -0.2686   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851    1.2031    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -2.0071   -1.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -2.8792   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.7858   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2233    1.4057    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -2.1450    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944   -2.9723    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3598   -1.3532    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    1.0222   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    3.8925    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    1.1956    1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    1.4872    1.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    2.2823    0.6200 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  2  0
 17 18  1  0
 17  2  1  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
M  END

784
  Mrv0541 02231215002D          

 18 19  0  0  0  0            999 V2000
    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
    2.3645   -1.3654    0.0000 C   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
    2.3645   -2.1904    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
    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
    1.6500   -0.9529    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
    3.7935    1.1096    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
    4.5080   -0.1279    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
    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 18  1  0  0  0  0
  2 18  2  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  4 10  1  0  0  0  0
  5  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 13  1  0  0  0  0
  7 12  1  0  0  0  0
  7 14  2  0  0  0  0
  8 11  1  0  0  0  0
  9 11  2  0  0  0  0
 12 15  2  0  0  0  0
 12 18  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014922

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)

> <INCHI_KEY>
HYYBABOKPJLUIN-UHFFFAOYSA-N

> <FORMULA>
C15H15NO2

> <MOLECULAR_WEIGHT>
241.2851

> <EXACT_MASS>
241.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.22289220936711

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2,3-dimethylphenyl)amino]benzoic acid

> <ALOGPS_LOGP>
4.58

> <JCHEM_LOGP>
5.397597278000001

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.769903367226913

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.885850840462833

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5789079095168428

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
71.8828

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mefenamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014922
     RDKit          3D
Mefenamic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.5244    0.0811    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218   -0.4171   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -1.5271   -0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828   -2.0134   -1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -1.3892   -1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.2879   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    0.4084    0.1040 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -0.0935    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845   -1.4360    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -1.9235    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254   -1.0296    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    0.3073   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757    0.7734   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6104    2.2164   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    2.7957   -0.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531    3.0247   -0.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    0.1691    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0196    1.3584    1.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6460   -0.0947    1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3645   -0.2686   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851    1.2031    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -2.0071   -1.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -2.8792   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.7858   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2233    1.4057    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -2.1450    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944   -2.9723    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3598   -1.3532    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    1.0222   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    3.8925    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    1.1956    1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    1.4872    1.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    2.2823    0.6200 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  2  0
 17 18  1  0
 17  2  1  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 784                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   4.381   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414   2.071   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.748  -0.239   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.414  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -1.779   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -4.089   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       7.081  -2.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -4.859   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -1.779   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -4.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   2.071   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -4.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -0.239   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       9.748   0.531   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   2.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   2.841   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3    5    7                                                       
CONECT    4    5    6   10                                                  
CONECT    5    3    4    8                                                  
CONECT    6    4    9   13                                                  
CONECT    7    3   12   14                                                  
CONECT    8    5   11                                                       
CONECT    9    6   11                                                       
CONECT   10    4                                                            
CONECT   11    8    9                                                       
CONECT   12    7   15   18                                                  
CONECT   13    6                                                            
CONECT   14    7   16                                                       
CONECT   15   12   17                                                       
CONECT   16   14   17                                                       
CONECT   17   15   16                                                       
CONECT   18    1    2   12                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0014922
HETATM    1  C1  UNL     1      -4.524   0.081   0.502  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.222  -0.417  -0.015  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.264  -1.527  -0.832  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.083  -2.013  -1.328  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.870  -1.389  -1.004  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.795  -0.288  -0.195  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.401   0.408   0.104  1.00  0.00           N  
HETATM    8  C7  UNL     1       1.720  -0.094   0.006  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.984  -1.436   0.163  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.291  -1.923   0.173  1.00  0.00           C  
HETATM   11  C10 UNL     1       4.325  -1.030   0.025  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.095   0.307  -0.132  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.776   0.773  -0.141  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.610   2.216  -0.365  1.00  0.00           C  
HETATM   15  O1  UNL     1       1.517   2.796  -0.454  1.00  0.00           O  
HETATM   16  O2  UNL     1       3.753   3.025  -0.490  1.00  0.00           O  
HETATM   17  C14 UNL     1      -2.024   0.169   0.283  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.020   1.358   1.166  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.646  -0.095   1.591  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.365  -0.269  -0.106  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.485   1.203   0.386  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.228  -2.007  -1.077  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.097  -2.879  -1.968  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.041  -1.786  -1.457  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.223   1.406   0.460  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.203  -2.145   0.320  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.494  -2.972   0.294  1.00  0.00           H  
HETATM   28  H10 UNL     1       5.360  -1.353   0.026  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.923   1.022  -0.250  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.808   3.893   0.043  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.228   1.196   1.935  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.962   1.487   1.717  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.713   2.282   0.620  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   17
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   24
CONECT    6    7   17   17
CONECT    7    8   25
CONECT    8    9    9   13
CONECT    9   10   26
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   30
CONECT   17   18
CONECT   18   31   32   33
END

HMDB0014922
     RDKit          3D
Mefenamic acid
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.5244    0.0811    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2218   -0.4171   -0.0150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2644   -1.5271   -0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0828   -2.0134   -1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -1.3892   -1.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948   -0.2879   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4013    0.4084    0.1040 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196   -0.0935    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845   -1.4360    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2914   -1.9235    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254   -1.0296    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    0.3073   -0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757    0.7734   -0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6104    2.2164   -0.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5171    2.7957   -0.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531    3.0247   -0.4905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0245    0.1691    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0196    1.3584    1.1660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6460   -0.0947    1.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3645   -0.2686   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4851    1.2031    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -2.0071   -1.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -2.8792   -1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.7858   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2233    1.4057    0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2032   -2.1450    0.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944   -2.9723    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3598   -1.3532    0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232    1.0222   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075    3.8925    0.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278    1.1956    1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    1.4872    1.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    2.2823    0.6200 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  6 17  2  0
 17 18  1  0
 17  2  1  0
 13  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 16 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acide mefenamique	ChEBI
Acido mefenamico	ChEBI
Acidum mefenamicum	ChEBI
CI-473	ChEBI
CN 35355	ChEBI
CN-35355	ChEBI
INF 3355	ChEBI
INF-3355	ChEBI
Mefenaminsaeure	ChEBI
N-(2,3-Xylyl)-2-aminobenzoic acid	ChEBI
N-2,3-Xylylanthranilic acid	ChEBI
Ponstel	ChEBI
N-(2,3-Xylyl)-2-aminobenzoate	Generator
N-2,3-Xylylanthranilate	Generator
Mefenamate	Generator
Mefanamic acid	HMDB
Mefenacid	HMDB
Mephenamic acid	HMDB
Mephenaminic acid	HMDB
Methenamic acid	HMDB
Acid, mefenaminic	HMDB
Antigen brand OF mefenamic acid	HMDB
Apo-mefenamic	HMDB
Ashbourne brand OF mefenamic acid	HMDB
Coslan	HMDB
Forte, ponstan	HMDB
Mefacit	HMDB
Mefic	HMDB
Nu-mefenamic	HMDB
PMS-Mefenamic acid	HMDB
Pfizer brand OF mefenamic acid	HMDB
Pinewood brand OF mefenamic acid	HMDB
Ponalar	HMDB
APS brand OF mefenamic acid	HMDB
Apo mefenamic	HMDB
Apotex brand OF mefenamic acid	HMDB
Dysman	HMDB
First horizon brand OF mefenamic acid	HMDB
Gödecke brand OF mefenamic acid	HMDB
Mefenaminic acid	HMDB
NuMefenamic	HMDB
PMS Mefenamic acid	HMDB
Ponalgic	HMDB
Warner-lambert brand OF mefenamic acid	HMDB
Chemidex brand OF mefenamic acid	HMDB
Contraflam	HMDB
Elan brand OF mefenamic acid	HMDB
Farmasierra brand OF mefenamic acid	HMDB
Nu-pharm brand OF mefenamic acid	HMDB
Parke davis brand OF mefenamic acid	HMDB
Parkemed	HMDB
Pinalgesic	HMDB
Ponmel	HMDB
Pontal	HMDB
Rowa brand OF mefenamic acid	HMDB
Acid, mefenamic	HMDB
ApoMefenamic	HMDB
Clonmel brand OF mefenamic acid	HMDB
Mefac	HMDB
Nu mefenamic	HMDB
Nu pharm brand OF mefenamic acid	HMDB
Pharmascience brand OF mefenamic acid	HMDB
Ponstan	HMDB
Ponstan forte	HMDB
Ponsyl	HMDB
Warner lambert brand OF mefenamic acid	HMDB

Chemical Formula

C₁₅H₁₅NO₂

Average Molecular Weight

241.2851

Monoisotopic Molecular Weight

241.110278729

IUPAC Name

2-[(2,3-dimethylphenyl)amino]benzoic acid

Traditional Name

mefenamic acid

CAS Registry Number

61-68-7

SMILES

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

InChI Identifier

InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)

InChI Key

HYYBABOKPJLUIN-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
Aniline or substituted anilines
Xylene
O-xylene
Vinylogous amide
Amino acid
Amino acid or derivatives
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:6717 )
aminobenzoic acid (CHEBI:6717 )

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: HMDB0014922)
Membrane (HMDB: HMDB0014922)

Source

Exogenous

Exogenous (HMDB: HMDB0014922)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Mefenamic Acid Action Pathway (PathBank: SMP0000109)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	230 - 231 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.014 g/L	Not Available
LogP	4.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	153.308	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000769

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	4.58	ALOGPS
logP	5.4	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-1.6	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	71.88 m³·mol⁻¹	ChemAxon
Polarizability	26.22 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
DarkChem	[M+H]+	156.313	31661259
DarkChem	[M-H]-	153.941	31661259
DeepCCS	[M+H]+	153.485	30932474
DeepCCS	[M-H]-	151.127	30932474
DeepCCS	[M-2H]-	184.122	30932474
DeepCCS	[M+Na]+	159.578	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.7	32859911
AllCCS	[M+NH4]+	157.3	32859911
AllCCS	[M+Na]+	158.4	32859911
AllCCS	[M-H]-	157.3	32859911
AllCCS	[M+Na-2H]-	156.8	32859911
AllCCS	[M+HCOO]-	156.4	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.	7.12 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6788 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.55 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2031.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	411.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	667.3 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	790.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	133.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1267.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	447.4 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	1526.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	331.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	378.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	177.1 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	82.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mefenamic acid	CC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C1	3376.3	Standard polar	33892256
Mefenamic acid	CC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C1	2219.3	Standard non polar	33892256
Mefenamic acid	CC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C1	2183.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mefenamic acid,1TMS,isomer #1	CC1=CC=CC(NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=C1C	2194.9	Semi standard non polar	33892256
Mefenamic acid,1TMS,isomer #2	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=C1C	2126.8	Semi standard non polar	33892256
Mefenamic acid,2TMS,isomer #1	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1C	2127.8	Semi standard non polar	33892256
Mefenamic acid,2TMS,isomer #1	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1C	2233.1	Standard non polar	33892256
Mefenamic acid,2TMS,isomer #1	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=C1C	2474.1	Standard polar	33892256
Mefenamic acid,1TBDMS,isomer #1	CC1=CC=CC(NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=C1C	2448.6	Semi standard non polar	33892256
Mefenamic acid,1TBDMS,isomer #2	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=C1C	2383.0	Semi standard non polar	33892256
Mefenamic acid,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C	2607.3	Semi standard non polar	33892256
Mefenamic acid,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C	2586.6	Standard non polar	33892256
Mefenamic acid,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1C	2736.2	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Mefenamic Acid Action Pathway		Not Available

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 DB00784	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00784	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00784

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3904

KEGG Compound ID

C02168

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mefenamic_acid

METLIN ID

Not Available

PubChem Compound

4044

PDB ID

ID8

ChEBI ID

6717

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. 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

Gierse JK, Hauser SD, Creely DP, Koboldt C, Rangwala SH, Isakson PC, Seibert K: Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem J. 1995 Jan 15;305 ( Pt 2):479-84. [PubMed:7832763 ]
Bhat AS, Tandan SK, Kumar D, Krishna V, Prakash VR: Interaction between inhibitors of inducible nitric oxide synthase and cyclooxygenase in adjuvant-induced arthritis in female albino rats: an isobolographic study. Eur J Pharmacol. 2007 Feb 5;556(1-3):190-9. Epub 2006 Oct 27. [PubMed:17150210 ]
Bhat AS, Tandan SK, Kumar D, Krishna V, Prakash VR: Interaction between inhibitors of inducible nitric oxide synthase and cyclooxygenase in Brewer's yeast induced pyrexia in mice: an isobolographic study. Eur J Pharmacol. 2005 Mar 28;511(2-3):137-42. [PubMed:15792781 ]
Cryer B, Feldman M: Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs. Am J Med. 1998 May;104(5):413-21. [PubMed:9626023 ]
Walton LJ, Franklin IJ, Bayston T, Brown LC, Greenhalgh RM, Taylor GW, Powell JT: Inhibition of prostaglandin E2 synthesis in abdominal aortic aneurysms: implications for smooth muscle cell viability, inflammatory processes, and the expansion of abdominal aortic aneurysms. Circulation. 1999 Jul 6;100(1):48-54. [PubMed:10393680 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. 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

Sinniah R, Lye WC: Acute renal failure from hemoglobinuric and interstitial nephritis secondary to iodine and mefenamic acid. Clin Nephrol. 2001 Mar;55(3):254-8. [PubMed:11316248 ]
Joo Y, Kim HS, Woo RS, Park CH, Shin KY, Lee JP, Chang KA, Kim S, Suh YH: Mefenamic acid shows neuroprotective effects and improves cognitive impairment in in vitro and in vivo Alzheimer's disease models. Mol Pharmacol. 2006 Jan;69(1):76-84. Epub 2005 Oct 13. [PubMed:16223958 ]
Cryer B, Feldman M: Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs. Am J Med. 1998 May;104(5):413-21. [PubMed:9626023 ]
Gierse JK, Hauser SD, Creely DP, Koboldt C, Rangwala SH, Isakson PC, Seibert K: Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem J. 1995 Jan 15;305 ( Pt 2):479-84. [PubMed:7832763 ]
Laudanno OM, Cesolari JA, Esnarriaga J, Flaherty P, Vada J, Guastalli G, San Miguel P, Bedini OA: [In vivo selectivity of nonsteroidal anti-inflammatory drugs on COX-1-COX-2 and gastrointestinal ulcers, in rats]. Acta Gastroenterol Latinoam. 1998;28(3):249-55. [PubMed:9773153 ]

Enzyme Details

3. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Mefenamic acid (HMDB0014922)

MOL for HMDB0014922 (Mefenamic acid)

3D MOL for HMDB0014922 (Mefenamic acid)

3D SDF for HMDB0014922 (Mefenamic acid)

3D-SDF for HMDB0014922 (Mefenamic acid)

PDB for HMDB0014922 (Mefenamic acid)

3D PDB for HMDB0014922 (Mefenamic acid)

SMILES for HMDB0014922 (Mefenamic acid)

INCHI for HMDB0014922 (Mefenamic acid)

Structure for HMDB0014922 (Mefenamic acid)

3D Structure for HMDB0014922 (Mefenamic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References