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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:55:42 UTC

Update Date

2022-03-07 02:57:15 UTC

HMDB ID

HMDB0042043

Secondary Accession Numbers

HMDB42043

Metabolite Identification

Common Name

Tolfenamic acid

Description

Tolfenamic acid, also known as acido tolfenamico or tolfenamate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Based on a literature review a significant number of articles have been published on Tolfenamic acid.

Structure

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

HMDB0042043
     RDKit          3D
Tolfenamic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    2.1725   -2.0819    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -0.7284    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014   -0.2902   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -1.2475   -0.0172 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7542    0.9562   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086    1.6861   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.2507   -0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    0.0174   -0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749   -0.5202    0.1011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762    0.2124    0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419    1.5114    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4061    2.1856    1.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    1.5928    0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7011    0.3112    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -0.3664    0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6645   -1.6902   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -2.1559   -0.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6645   -2.5403   -0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482   -1.9255    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204   -2.4004    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -2.8230   -0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7372    1.3355   -1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    2.6829   -1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962    1.9207   -1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.5778    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2742    1.9635    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3244    3.1896    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482    2.1324    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6911   -0.1205    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3510   -2.4801   -1.8302 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
  8  2  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
M  END


  Mrv0541 09131211552D          

 18 19  0  0  0  0            999 V2000
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  1  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0042043

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18)

> <INCHI_KEY>
YEZNLOUZAIOMLT-UHFFFAOYSA-N

> <FORMULA>
C14H12ClNO2

> <MOLECULAR_WEIGHT>
261.704

> <EXACT_MASS>
261.05565634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.459976088998776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3-chloro-2-methylphenyl)amino]benzoic acid

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
5.488220565

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.307550753283422

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8788522801256358

> <JCHEM_PKA_STRONGEST_BASIC>
-2.101670898633361

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
71.64640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tolfenamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0042043
     RDKit          3D
Tolfenamic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    2.1725   -2.0819    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -0.7284    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014   -0.2902   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -1.2475   -0.0172 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7542    0.9562   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086    1.6861   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.2507   -0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    0.0174   -0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749   -0.5202    0.1011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762    0.2124    0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419    1.5114    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4061    2.1856    1.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    1.5928    0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7011    0.3112    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -0.3664    0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6645   -1.6902   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -2.1559   -0.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6645   -2.5403   -0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482   -1.9255    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204   -2.4004    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -2.8230   -0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7372    1.3355   -1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    2.6829   -1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962    1.9207   -1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.5778    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2742    1.9635    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3244    3.1896    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482    2.1324    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6911   -0.1205    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3510   -2.4801   -1.8302 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
  8  2  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -1.334   8.470   0.000  0.00  0.00          Cl+0
HETATM   16  N   UNK     0       4.001   8.470   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3    5                                                       
CONECT    3    2    7                                                       
CONECT    4    6    8                                                       
CONECT    5    2   10                                                       
CONECT    6    4   11                                                       
CONECT    7    3   13                                                       
CONECT    8    4   12                                                       
CONECT    9    1   11   12                                                  
CONECT   10    5   13   14                                                  
CONECT   11    6    9   15                                                  
CONECT   12    8    9   16                                                  
CONECT   13    7   10   16                                                  
CONECT   14   10   17   18                                                  
CONECT   15   11                                                            
CONECT   16   12   13                                                       
CONECT   17   14                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0042043
HETATM    1  C1  UNL     1       2.173  -2.082   0.650  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.344  -0.728   0.025  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.601  -0.290  -0.300  1.00  0.00           C  
HETATM    4 CL1  UNL     1       5.036  -1.248  -0.017  1.00  0.00          CL  
HETATM    5  C4  UNL     1       3.754   0.956  -0.874  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.609   1.686  -1.085  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.333   1.251  -0.761  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.180   0.017  -0.190  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.075  -0.520   0.101  1.00  0.00           N  
HETATM   10  C8  UNL     1      -1.276   0.212   0.286  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.242   1.511   0.781  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.406   2.186   1.059  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.629   1.593   0.856  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.701   0.311   0.370  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.520  -0.366   0.089  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.665  -1.690  -0.463  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.852  -2.156  -0.603  1.00  0.00           O  
HETATM   18  O2  UNL     1      -1.664  -2.540  -0.872  1.00  0.00           O  
HETATM   19  H1  UNL     1       1.448  -1.925   1.497  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.120  -2.400   1.125  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.784  -2.823  -0.077  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.737   1.335  -1.143  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.701   2.683  -1.541  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.496   1.921  -1.023  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.098  -1.578   0.213  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.274   1.963   0.983  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.324   3.190   1.439  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.548   2.132   1.079  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.691  -0.120   0.225  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.351  -2.480  -1.830  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    8
CONECT    3    4    5
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9
CONECT    9   10   25
CONECT   10   11   11   15
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   30
END

HMDB0042043
     RDKit          3D
Tolfenamic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    2.1725   -2.0819    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3444   -0.7284    0.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6014   -0.2902   -0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0357   -1.2475   -0.0172 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7542    0.9562   -0.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086    1.6861   -1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329    1.2507   -0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    0.0174   -0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749   -0.5202    0.1011 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2762    0.2124    0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419    1.5114    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4061    2.1856    1.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286    1.5928    0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7011    0.3112    0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5204   -0.3664    0.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6645   -1.6902   -0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8522   -2.1559   -0.6025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6645   -2.5403   -0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482   -1.9255    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204   -2.4004    1.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -2.8230   -0.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7372    1.3355   -1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7007    2.6829   -1.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962    1.9207   -1.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -1.5778    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2742    1.9635    0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3244    3.1896    1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482    2.1324    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6911   -0.1205    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3510   -2.4801   -1.8302 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
  8  2  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 18 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Acide tolfenamique	ChEBI
Acido tolfenamico	ChEBI
Acidum tolfenamicum	ChEBI
N-(2-Methyl-3-chlorophenyl)anthranilic acid	ChEBI
N-(3-Chloro-2-methylphenyl)anthranilic acid	ChEBI
N-(3-Chloro-O-tolyl)-anthranilic acid	ChEBI
N-(2-Methyl-3-chlorophenyl)anthranilate	Generator
N-(3-Chloro-2-methylphenyl)anthranilate	Generator
N-(3-Chloro-O-tolyl)-anthranilate	Generator
Tolfenamate	Generator
Clotam	HMDB
Pharmacia brand OF tolfenamic acid	HMDB
Rociclyn	HMDB
Bifenac	HMDB
N-(3-Chloro-O-tolyl)anthranilic acid	HMDB
Provalis brand OF tolfenamic acid	HMDB
Zambon brand OF tolfenamic acid	HMDB

Chemical Formula

C₁₄H₁₂ClNO₂

Average Molecular Weight

261.704

Monoisotopic Molecular Weight

261.05565634

IUPAC Name

2-[(3-chloro-2-methylphenyl)amino]benzoic acid

Traditional Name

tolfenamic acid

CAS Registry Number

13710-19-5

SMILES

CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18)

InChI Key

YEZNLOUZAIOMLT-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
Aminotoluene
Chlorobenzene
Halobenzene
Toluene
Aryl chloride
Aryl halide
Vinylogous amide
Amino acid or derivatives
Amino acid
Secondary amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organohalogen compound
Amine
Organic oxygen compound
Organic oxide
Organopnictogen compound
Organochloride
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organochlorine compound (CHEBI:32243 )
secondary amino compound (CHEBI:32243 )
aminobenzoic acid (CHEBI:32243 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0042043)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	207 - 207.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	5.17	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	155.565	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000907

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	4.64	ALOGPS
logP	5.49	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.88	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	3	ChemAxon
Refractivity	71.65 m³·mol⁻¹	ChemAxon
Polarizability	26.46 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
DeepCCS	[M+H]+	153.124	30932474
DeepCCS	[M-H]-	150.766	30932474
DeepCCS	[M-2H]-	184.188	30932474
DeepCCS	[M+Na]+	159.217	30932474
AllCCS	[M+H]+	155.7	32859911
AllCCS	[M+H-H2O]+	151.9	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.2	32859911
AllCCS	[M-H]-	154.6	32859911
AllCCS	[M+Na-2H]-	154.0	32859911
AllCCS	[M+HCOO]-	153.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tolfenamic acid	CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O	3708.0	Standard polar	33892256
Tolfenamic acid	CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O	2278.3	Standard non polar	33892256
Tolfenamic acid	CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O	2292.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tolfenamic acid,1TMS,isomer #1	CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(=O)O[Si](C)(C)C	2264.4	Semi standard non polar	33892256
Tolfenamic acid,1TMS,isomer #2	CC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C	2179.4	Semi standard non polar	33892256
Tolfenamic acid,2TMS,isomer #1	CC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C	2197.3	Semi standard non polar	33892256
Tolfenamic acid,2TMS,isomer #1	CC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C)[Si](C)(C)C	2264.7	Standard non polar	33892256
Tolfenamic acid,1TBDMS,isomer #1	CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2510.7	Semi standard non polar	33892256
Tolfenamic acid,1TBDMS,isomer #2	CC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O)[Si](C)(C)C(C)(C)C	2427.4	Semi standard non polar	33892256
Tolfenamic acid,2TBDMS,isomer #1	CC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2661.1	Semi standard non polar	33892256
Tolfenamic acid,2TBDMS,isomer #1	CC1=C(Cl)C=CC=C1N(C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2635.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tolfenamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-029f-0290000000-193c55add3bbbb7d5121	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolfenamic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9354000000-172c43eaed1235f269a7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolfenamic 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 - Tolfenamic acid , positive-QTOF	splash10-0006-1290000000-90928e5629bf0b4869e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolfenamic acid , positive-QTOF	splash10-0a59-2790000000-175a0f838779d665e3db	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 10V, Positive-QTOF	splash10-03di-0090000000-9e173e701dad784002bf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 20V, Positive-QTOF	splash10-02vl-0490000000-383bb531cf3b364e8551	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 40V, Positive-QTOF	splash10-004i-3920000000-f62680abb4f65b264811	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 10V, Negative-QTOF	splash10-02t9-0090000000-a116f61548e6965f47fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 20V, Negative-QTOF	splash10-014i-0190000000-d6c269ae6e8f165e1af8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 40V, Negative-QTOF	splash10-00l6-7970000000-7e83c63a8f674eb4dbb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 10V, Negative-QTOF	splash10-03di-0090000000-f1e193bda03b4aaed004	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 20V, Negative-QTOF	splash10-014i-2190000000-2fcbcc8f4250abae18dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 40V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 10V, Positive-QTOF	splash10-01ox-0090000000-d9fc45f2fd3466ad4bb4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 20V, Positive-QTOF	splash10-0006-0090000000-8d746ea562322ef5c27a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolfenamic acid 40V, Positive-QTOF	splash10-053r-0950000000-1f2515f699ddfef235a4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09216

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

530683

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tolfenamic_acid

METLIN ID

Not Available

PubChem Compound

610479

PDB ID

TLF

ChEBI ID

32243

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

Eslin D, Sankpal UT, Lee C, Sutphin RM, Maliakal P, Currier E, Sholler G, Khan M, Basha R: Tolfenamic acid inhibits neuroblastoma cell proliferation and induces apoptosis: a novel therapeutic agent for neuroblastoma. Mol Carcinog. 2013 May;52(5):377-86. doi: 10.1002/mc.21866. Epub 2011 Dec 28. [PubMed:22213339 ]
Chadalapaka G, Jutooru I, Sreevalsan S, Pathi S, Kim K, Chen C, Crose L, Linardic C, Safe S: Inhibition of rhabdomyosarcoma cell and tumor growth by targeting specificity protein (Sp) transcription factors. Int J Cancer. 2013 Feb 15;132(4):795-806. doi: 10.1002/ijc.27730. Epub 2012 Aug 3. [PubMed:22815231 ]
Sutphin RM, Connelly SF, Lee CM, Sankpal UT, Eslin D, Khan M, Pius H, Basha R: Anti-leukemic response of a NSAID, tolfenamic acid. Target Oncol. 2014 Jun;9(2):135-44. doi: 10.1007/s11523-013-0274-9. Epub 2013 Apr 23. [PubMed:23609055 ]
Subaiea GM, Adwan LI, Ahmed AH, Stevens KE, Zawia NH: Short-term treatment with tolfenamic acid improves cognitive functions in Alzheimer's disease mice. Neurobiol Aging. 2013 Oct;34(10):2421-30. doi: 10.1016/j.neurobiolaging.2013.04.002. Epub 2013 Apr 30. [PubMed:23639209 ]
Eslin D, Lee C, Sankpal UT, Maliakal P, Sutphin RM, Abraham L, Basha R: Anticancer activity of tolfenamic acid in medulloblastoma: a preclinical study. Tumour Biol. 2013 Oct;34(5):2781-9. doi: 10.1007/s13277-013-0836-6. Epub 2013 May 18. [PubMed:23686785 ]
Jeong JB, Yang X, Clark R, Choi J, Baek SJ, Lee SH: A mechanistic study of the proapoptotic effect of tolfenamic acid: involvement of NF-kappaB activation. Carcinogenesis. 2013 Oct;34(10):2350-60. doi: 10.1093/carcin/bgt224. Epub 2013 Jun 19. [PubMed:23784084 ]
Nadanaciva S, Aleo MD, Strock CJ, Stedman DB, Wang H, Will Y: Toxicity assessments of nonsteroidal anti-inflammatory drugs in isolated mitochondria, rat hepatocytes, and zebrafish show good concordance across chemical classes. Toxicol Appl Pharmacol. 2013 Oct 15;272(2):272-80. doi: 10.1016/j.taap.2013.06.019. Epub 2013 Jun 26. [PubMed:23811329 ]
Zhang X, Min KW, Liggett J, Baek SJ: Disruption of the transforming growth factor-beta pathway by tolfenamic acid via the ERK MAP kinase pathway. Carcinogenesis. 2013 Dec;34(12):2900-7. doi: 10.1093/carcin/bgt250. Epub 2013 Jul 16. [PubMed:23864386 ]
Kim HJ, Cho SD, Kim J, Kim SJ, Choi C, Kim JS, Nam JS, Han Kwon K, Kang KS, Jung JY: Apoptotic effect of tolfenamic acid on MDA-MB-231 breast cancer cells and xenograft tumors. J Clin Biochem Nutr. 2013 Jul;53(1):21-6. doi: 10.3164/jcbn.12-78. Epub 2013 Jun 29. [PubMed:23874066 ]
Jeong JB, Choi J, Baek SJ, Lee SH: Reactive oxygen species mediate tolfenamic acid-induced apoptosis in human colorectal cancer cells. Arch Biochem Biophys. 2013 Sep 15;537(2):168-75. doi: 10.1016/j.abb.2013.07.016. Epub 2013 Jul 26. [PubMed:23896517 ]

Showing metabocard for Tolfenamic acid (HMDB0042043)

MOL for HMDB0042043 (Tolfenamic acid)

3D MOL for HMDB0042043 (Tolfenamic acid)

3D SDF for HMDB0042043 (Tolfenamic acid)

3D-SDF for HMDB0042043 (Tolfenamic acid)

PDB for HMDB0042043 (Tolfenamic acid)

3D PDB for HMDB0042043 (Tolfenamic acid)

SMILES for HMDB0042043 (Tolfenamic acid)

INCHI for HMDB0042043 (Tolfenamic acid)

Structure for HMDB0042043 (Tolfenamic acid)

3D Structure for HMDB0042043 (Tolfenamic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra