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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014643

Secondary Accession Numbers

HMDB14643

Metabolite Identification

Common Name

Tolmetin

Description

Tolmetin is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory agent (anti-inflammatory agents, NON-steroidal) similar in mode of action to indomethacin. [PubChem]The mode of action of tolmetin is not known. However, studies in laboratory animals and man have demonstrated that the anti-inflammatory action of tolmetin is not due to pituitary-adrenal stimulation. Tolmetin inhibits prostaglandin synthetase in vitro and lowers the plasma level of prostaglandin E in man. This reduction in prostaglandin synthesis may be responsible for the anti-inflammatory action. Tolmetin does not appear to alter the course of the underlying disease in man.

Structure

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

HMDB0014643
     RDKit          3D
Tolmetin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.7804    0.7470    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4037    0.1666    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193    0.9552    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    0.4899    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -0.7944   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928   -1.2784   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511   -2.5076   -0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134   -0.3514   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6957    0.8833   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327    1.4697   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6815    0.5829    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967    0.7607    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0133    0.4644   -0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.1810   -1.7455 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3700    0.4939   -0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191   -0.5183    0.3128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4471   -1.6506    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -1.5812   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -1.1095   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7470    1.8578    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3196    0.5048    1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985    0.4038   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056    1.9485    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165    1.1302    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    1.3672   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2898    2.4305   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357    0.0078    1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935    1.7953    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9194    1.3445   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523   -1.3036    2.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2659   -2.1232    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511   -2.3971    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -2.6072   -0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -1.7625   -0.5949 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

500
  Mrv0541 02231214432D          

 19 20  0  0  0  0            999 V2000
    1.6500    0.5368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4638    3.1223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6132    1.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652    1.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3078    2.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5521    1.9092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283    2.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2 18  1  0  0  0  0
  3 18  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  5  7  2  0  0  0  0
  5  9  1  0  0  0  0
  6  8  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  9 18  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014643

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)

> <INCHI_KEY>
UPSPUYADGBWSHF-UHFFFAOYSA-N

> <FORMULA>
C15H15NO3

> <MOLECULAR_WEIGHT>
257.2845

> <EXACT_MASS>
257.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.6735065796209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.7273309576666667

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9581683675853068

> <JCHEM_PKA_STRONGEST_BASIC>
-7.781456553696511

> <JCHEM_POLAR_SURFACE_AREA>
59.3

> <JCHEM_REFRACTIVITY>
72.3928

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tolmetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014643
     RDKit          3D
Tolmetin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.7804    0.7470    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4037    0.1666    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193    0.9552    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    0.4899    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -0.7944   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928   -1.2784   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511   -2.5076   -0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134   -0.3514   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6957    0.8833   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327    1.4697   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6815    0.5829    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967    0.7607    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0133    0.4644   -0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.1810   -1.7455 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3700    0.4939   -0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191   -0.5183    0.3128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4471   -1.6506    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -1.5812   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -1.1095   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7470    1.8578    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3196    0.5048    1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985    0.4038   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056    1.9485    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165    1.1302    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    1.3672   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2898    2.4305   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357    0.0078    1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935    1.7953    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9194    1.3445   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523   -1.3036    2.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2659   -2.1232    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511   -2.3971    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -2.6072   -0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -1.7625   -0.5949 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 500                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   1.002   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.199   5.828   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.478   3.176   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.908   2.533   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.415   2.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   1.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.185   1.520   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.154   0.375   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.041   4.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.232   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.764   3.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -1.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -2.078   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747  -2.078   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -4.388   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080  -3.618   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -3.618   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.573   4.422   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -5.928   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   18                                                            
CONECT    3   18                                                            
CONECT    4    5    6   11                                                  
CONECT    5    4    7    9                                                  
CONECT    6    4    8   10                                                  
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    5   18                                                       
CONECT   10    1    6   12                                                  
CONECT   11    4                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   16                                                       
CONECT   14   12   17                                                       
CONECT   15   16   17   19                                                  
CONECT   16   13   15                                                       
CONECT   17   14   15                                                       
CONECT   18    2    3    9                                                  
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014643
HETATM    1  C1  UNL     1      -5.780   0.747   0.195  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.404   0.167   0.110  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.319   0.955   0.461  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.026   0.490   0.388  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.781  -0.794  -0.047  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.393  -1.278  -0.150  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.151  -2.508  -0.171  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.713  -0.351  -0.229  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.696   0.883  -0.856  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.933   1.470  -0.681  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.682   0.583   0.048  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.097   0.761   0.507  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.013   0.464  -0.639  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.505   0.181  -1.745  1.00  0.00           O  
HETATM   15  O3  UNL     1       6.370   0.494  -0.513  1.00  0.00           O  
HETATM   16  N1  UNL     1       1.919  -0.518   0.313  1.00  0.00           N  
HETATM   17  C13 UNL     1       2.447  -1.651   1.087  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.832  -1.581  -0.393  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.142  -1.109  -0.317  1.00  0.00           C  
HETATM   20  H1  UNL     1      -5.747   1.858   0.101  1.00  0.00           H  
HETATM   21  H2  UNL     1      -6.320   0.505   1.109  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.399   0.404  -0.664  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.506   1.949   0.798  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.217   1.130   0.676  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.123   1.367  -1.412  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.290   2.430  -1.026  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.336   0.008   1.313  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.194   1.795   0.875  1.00  0.00           H  
HETATM   29  H10 UNL     1       6.919   1.345  -0.468  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.752  -1.304   2.103  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.266  -2.123   0.533  1.00  0.00           H  
HETATM   32  H13 UNL     1       1.651  -2.397   1.249  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.664  -2.607  -0.735  1.00  0.00           H  
HETATM   34  H15 UNL     1      -4.980  -1.762  -0.595  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   19
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   18
CONECT    6    7    7    8
CONECT    8    9    9   16
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   16
CONECT   12   13   27   28
CONECT   13   14   14   15
CONECT   15   29
CONECT   16   17
CONECT   17   30   31   32
CONECT   18   19   19   33
CONECT   19   34
END

HMDB0014643
     RDKit          3D
Tolmetin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.7804    0.7470    0.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4037    0.1666    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193    0.9552    0.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    0.4899    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -0.7944   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3928   -1.2784   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1511   -2.5076   -0.1714 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7134   -0.3514   -0.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6957    0.8833   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9327    1.4697   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6815    0.5829    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967    0.7607    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0133    0.4644   -0.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    0.1810   -1.7455 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3700    0.4939   -0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9191   -0.5183    0.3128 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4471   -1.6506    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8322   -1.5812   -0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -1.1095   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7470    1.8578    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3196    0.5048    1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3985    0.4038   -0.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056    1.9485    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2165    1.1302    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    1.3672   -1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2898    2.4305   -1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357    0.0078    1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1935    1.7953    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9194    1.3445   -0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523   -1.3036    2.1030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2659   -2.1232    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6511   -2.3971    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6640   -2.6072   -0.7349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802   -1.7625   -0.5949 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  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 11 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 12 28  1  0
 15 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetic acid	ChEBI
1-Methyl-5-p-toluoylpyrrole-2-acetic acid	ChEBI
5-(p-Toluoyl)-1-methylpyrrole-2-acetic acid	ChEBI
Tolmetina	ChEBI
Tolmetine	ChEBI
Tolmetino	ChEBI
Tolmetinum	ChEBI
1-Methyl-5-(4-methylbenzoyl)-pyrrole-2-acetate	Generator
1-Methyl-5-p-toluoylpyrrole-2-acetate	Generator
5-(p-Toluoyl)-1-methylpyrrole-2-acetate	Generator
Anhydrous tolmetin sodium	HMDB
Sodium anhydrous, tolmetin	HMDB
Tolectin	HMDB
Tolmetin sodium	HMDB
Anhydrous, tolmetin sodium	HMDB
Dihydrate tolmetin sodium	HMDB
Sodium, tolmetin	HMDB
Tolmetin sodium anhydrous	HMDB
Tolmetin sodium, anhydrous	HMDB
Tolmetin sodium, dihydrate	HMDB

Chemical Formula

C₁₅H₁₅NO₃

Average Molecular Weight

257.2845

Monoisotopic Molecular Weight

257.105193351

IUPAC Name

2-[1-methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

Traditional Name

tolmetin

CAS Registry Number

26171-23-3

SMILES

CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18)

InChI Key

UPSPUYADGBWSHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Benzoyl
Toluene
Monocyclic benzene moiety
N-methylpyrrole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:71941 )
aromatic ketone (CHEBI:71941 )
pyrroles (CHEBI:71941 )

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: HMDB0014643)
Membrane (HMDB: HMDB0014643)

Source

Exogenous

Exogenous (HMDB: HMDB0014643)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Tolmetin Action Pathway (PathBank: SMP0000704)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.13 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	158.717	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001329

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.73	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.39 m³·mol⁻¹	ChemAxon
Polarizability	27.67 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.812	31661259
DarkChem	[M-H]-	159.734	31661259
DeepCCS	[M+H]+	164.599	30932474
DeepCCS	[M-H]-	162.241	30932474
DeepCCS	[M-2H]-	195.127	30932474
DeepCCS	[M+Na]+	170.692	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	155.6	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tolmetin	CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1	3472.9	Standard polar	33892256
Tolmetin	CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1	2091.0	Standard non polar	33892256
Tolmetin	CN1C(CC(O)=O)=CC=C1C(=O)C1=CC=C(C)C=C1	2296.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tolmetin,1TMS,isomer #1	CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[Si](C)(C)C)N2C)C=C1	2362.3	Semi standard non polar	33892256
Tolmetin,1TBDMS,isomer #1	CC1=CC=C(C(=O)C2=CC=C(CC(=O)O[Si](C)(C)C(C)(C)C)N2C)C=C1	2651.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tolmetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3930000000-6c43d7fafa7e68cf9c55	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolmetin GC-MS (1 TMS) - 70eV, Positive	splash10-032i-9442000000-7726560133a119872ef9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolmetin 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 - Tolmetin LC-ESI-QQ , positive-QTOF	splash10-0a4i-0090000000-5053b1021a81c4668b54	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOF	splash10-014i-0910000000-7cb6eb9d5a42f35eb4bc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOF	splash10-014i-0900000000-9898c207cc31a596d319	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOF	splash10-014l-6900000000-439955132bb3d3d37cf7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolmetin LC-ESI-QQ , positive-QTOF	splash10-0006-9200000000-aed48305fd97ea83af6d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolmetin LC-ESI-IT , positive-QTOF	splash10-014i-1900000000-3399455ef4fbd98a64d3	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 10V, Positive-QTOF	splash10-0a4l-0090000000-3838af75b0622946263b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 20V, Positive-QTOF	splash10-014i-0950000000-f1c503badfc8847c75e8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 40V, Positive-QTOF	splash10-014l-6900000000-075fb92a19ab89905ba3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 10V, Negative-QTOF	splash10-0a4i-0090000000-5613b7d02b59ebbf2b1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 20V, Negative-QTOF	splash10-0bt9-1290000000-494f40e70f911873c728	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 40V, Negative-QTOF	splash10-006y-9730000000-49d63827f01b8620343f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 10V, Negative-QTOF	splash10-03di-0090000000-6a704ffbf3202179ae4b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 20V, Negative-QTOF	splash10-01ox-8390000000-db73eded70ef5ae97453	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 40V, Negative-QTOF	splash10-0006-5900000000-f83dcdc322966fec3da8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 10V, Positive-QTOF	splash10-0a4i-0190000000-71c82a0a228a88e32b6d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 20V, Positive-QTOF	splash10-066u-1890000000-018d899ab34427dfd79d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolmetin 40V, Positive-QTOF	splash10-0006-9720000000-7eec80edd3ab412a096d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tolmetin 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 DB00500	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00500	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00500

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5308

KEGG Compound ID

C07149

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tolmetin

METLIN ID

Not Available

PubChem Compound

5509

PDB ID

Not Available

ChEBI ID

71941

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

Burdan F, Szumilo J, Klepacz R, Dudka J, Korobowicz A, Tokarska E, Cendrowska-Pinkosz M, Madej B, Klepacz L: Gastrointestinal and hepatic toxicity of selective and non-selective cyclooxygenase-2 inhibitors in pregnant and non-pregnant rats. Pharmacol Res. 2004 Nov;50(5):533-43. [PubMed:15458776 ]
Capasso A, Sorrentino L: Arachidonic acid and its metabolites are involved in the expression of morphine dependence in guinea-pig isolated ileum. Eur J Pharmacol. 1997 Jul 9;330(2-3):199-204. [PubMed:9253954 ]
Kirkova M, Alexandova A, Kesiova M, Todorov S: In vivo effects of amtolmetin guacyl on lipid peroxidation and antioxidant defence systems. Comparison with non-selective and COX-2 selective NSAIDs. Auton Autacoid Pharmacol. 2007 Apr;27(2):99-104. [PubMed:17391279 ]
Kennedy JH, Korn N, Thurston RJ: Prostaglandin levels in seminal plasma and sperm extracts of the domestic turkey, and the effects of cyclooxygenase inhibitors on sperm mobility. Reprod Biol Endocrinol. 2003 Oct 9;1:74. [PubMed:14613550 ]
Capasso A: Further studies on the involvement of the arachidonic acid cascade in the acute dependence produced by mu, kappa and delta opioid agonists in isolated tissues. Neuropharmacology. 1999 Jun;38(6):871-7. [PubMed:10465690 ]
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

Capasso A, Sorrentino L: Arachidonic acid and its metabolites are involved in the expression of morphine dependence in guinea-pig isolated ileum. Eur J Pharmacol. 1997 Jul 9;330(2-3):199-204. [PubMed:9253954 ]
Kennedy JH, Korn N, Thurston RJ: Prostaglandin levels in seminal plasma and sperm extracts of the domestic turkey, and the effects of cyclooxygenase inhibitors on sperm mobility. Reprod Biol Endocrinol. 2003 Oct 9;1:74. [PubMed:14613550 ]
Capasso A: Further studies on the involvement of the arachidonic acid cascade in the acute dependence produced by mu, kappa and delta opioid agonists in isolated tissues. Neuropharmacology. 1999 Jun;38(6):871-7. [PubMed:10465690 ]
Burdan F, Szumilo J, Marzec B, Klepacz R, Dudka J: Skeletal developmental effects of selective and nonselective cyclooxygenase-2 inhibitors administered through organogenesis and fetogenesis in Wistar CRL:(WI)WUBR rats. Toxicology. 2005 Dec 15;216(2-3):204-23. Epub 2005 Sep 22. [PubMed:16182428 ]

Transporters

Enzyme Details

1. 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 Tolmetin (HMDB0014643)

MOL for HMDB0014643 (Tolmetin)

3D MOL for HMDB0014643 (Tolmetin)

3D SDF for HMDB0014643 (Tolmetin)

3D-SDF for HMDB0014643 (Tolmetin)

PDB for HMDB0014643 (Tolmetin)

3D PDB for HMDB0014643 (Tolmetin)

SMILES for HMDB0014643 (Tolmetin)

INCHI for HMDB0014643 (Tolmetin)

Structure for HMDB0014643 (Tolmetin)

3D Structure for HMDB0014643 (Tolmetin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References