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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015538

Secondary Accession Numbers

HMDB15538

Metabolite Identification

Common Name

Tiaprofenic acid

Description

Tiaprofenic acid is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain.Tiaprofenic acid belongs to a group of medicines called non-steroidal anti-inflammatory drugs (NSAIDs). It works by blocking the production of a chemical (prostaglandin) which the body produces in response to injury or certain diseases. This prostaglandin would otherwise go on to cause swelling, pain and inflammation.

Structure

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

HMDB0015538
     RDKit          3D
Tiaprofenic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.1791   -1.7750    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.4689    0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4371    0.6958    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3517    0.5114   -0.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1581    1.9771    0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -0.3410    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4214    0.7686    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323    0.6444    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -0.5845   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290   -1.0359   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328   -2.0020   -1.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8195   -0.3778   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8523    0.3019    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075    0.9548    1.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1202    0.8958    0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792    0.2049   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498   -0.4433   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -1.5433   -0.2265 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -2.5792    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083   -1.9409    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647   -1.8187   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7669   -0.4784    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264    2.7685    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8521    1.7339    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5943    1.4931    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.3678    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407    1.5017    2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0471    1.3882    0.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711    0.1713   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880   -0.9904   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18  6  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

1600
  Mrv0541 02231215352D          

 18 19  0  0  1  0            999 V2000
    3.1652    0.9447    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4638    2.7098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6132    1.2888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3078    1.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847    0.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8229    2.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8327   -0.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1283    1.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2 12  1  0  0  0  0
  3 11  2  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  2  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015538

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17)

> <INCHI_KEY>
GUHPRPJDBZHYCJ-UHFFFAOYSA-N

> <FORMULA>
C14H12O3S

> <MOLECULAR_WEIGHT>
260.308

> <EXACT_MASS>
260.05071494

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.777139412484352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-benzoylthiophen-2-yl)propanoic acid

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
3.658654214

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.03430557260978

> <JCHEM_PKA_STRONGEST_BASIC>
-7.8159756912028655

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
69.18960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tiaprofenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015538
     RDKit          3D
Tiaprofenic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.1791   -1.7750    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.4689    0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4371    0.6958    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3517    0.5114   -0.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1581    1.9771    0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -0.3410    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4214    0.7686    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323    0.6444    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -0.5845   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290   -1.0359   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328   -2.0020   -1.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8195   -0.3778   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8523    0.3019    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075    0.9548    1.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1202    0.8958    0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792    0.2049   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498   -0.4433   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -1.5433   -0.2265 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -2.5792    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083   -1.9409    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647   -1.8187   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7669   -0.4784    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264    2.7685    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8521    1.7339    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5943    1.4931    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.3678    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407    1.5017    2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0471    1.3882    0.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711    0.1713   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880   -0.9904   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18  6  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1600                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.908   1.763   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.199   5.058   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080   0.232   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.478   2.406   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.041   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.415   2.084   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   0.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.185   0.750   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.136   4.736   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.154  -0.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -0.538   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.573   3.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -2.078   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747  -2.848   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -2.848   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.747  -4.388   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -4.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -5.158   0.000  0.00  0.00           C+0
CONECT    1    6    7                                                       
CONECT    2   12                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    9   12                                                  
CONECT    6    1    5    8                                                  
CONECT    7    1   10   11                                                  
CONECT    8    6   10                                                       
CONECT    9    5                                                            
CONECT   10    7    8                                                       
CONECT   11    3    7   13                                                  
CONECT   12    2    4    5                                                  
CONECT   13   11   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015538
HETATM    1  C1  UNL     1       4.179  -1.775   0.144  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.660  -0.469   0.660  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.437   0.696   0.158  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.352   0.511  -0.655  1.00  0.00           O  
HETATM    5  O2  UNL     1       4.158   1.977   0.580  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.207  -0.341   0.326  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.421   0.769   0.393  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.132   0.644   0.040  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.306  -0.585  -0.362  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.629  -1.036  -0.809  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.733  -2.002  -1.608  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.820  -0.378  -0.339  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.852   0.302   0.842  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.008   0.955   1.276  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.120   0.896   0.478  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.079   0.205  -0.718  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.950  -0.443  -1.160  1.00  0.00           C  
HETATM   18  S1  UNL     1       1.138  -1.543  -0.227  1.00  0.00           S  
HETATM   19  H1  UNL     1       3.544  -2.579   0.559  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.208  -1.941   0.534  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.265  -1.819  -0.969  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.767  -0.478   1.772  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.726   2.769   0.418  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.852   1.734   0.726  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.594   1.493   0.046  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.009   0.368   1.513  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.041   1.502   2.218  1.00  0.00           H  
HETATM   28  H10 UNL     1      -6.047   1.388   0.772  1.00  0.00           H  
HETATM   29  H11 UNL     1      -5.971   0.171  -1.340  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.888  -0.990  -2.095  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    6   22
CONECT    3    4    4    5
CONECT    5   23
CONECT    6    7    7   18
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   18
CONECT   10   11   11   12
CONECT   12   13   13   17
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   16   28
CONECT   16   17   17   29
CONECT   17   30
END

HMDB0015538
     RDKit          3D
Tiaprofenic acid
 30 31  0  0  0  0  0  0  0  0999 V2000
    4.1791   -1.7750    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -0.4689    0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4371    0.6958    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3517    0.5114   -0.6554 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1581    1.9771    0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069   -0.3410    0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4214    0.7686    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323    0.6444    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -0.5845   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290   -1.0359   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7328   -2.0020   -1.6077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8195   -0.3778   -0.3394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8523    0.3019    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0075    0.9548    1.2764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1202    0.8958    0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0792    0.2049   -0.7185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9498   -0.4433   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383   -1.5433   -0.2265 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441   -2.5792    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2083   -1.9409    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647   -1.8187   -0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7669   -0.4784    1.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7264    2.7685    0.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8521    1.7339    0.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5943    1.4931    0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.3678    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0407    1.5017    2.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0471    1.3882    0.7716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711    0.1713   -1.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880   -0.9904   -2.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18  6  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(5-Benzoyl-thiophen-2-yl)-propionic acid	ChEBI
2-(5-Benzyl-2-thienyl)propionsaeure	ChEBI
5-Benzoyl-alpha-methyl-2-thiopheneacetic acid	ChEBI
5-Benzoyl-alpha-methylthiophene-2-acetic acid	ChEBI
Acide tiaprofenique	ChEBI
Acido tiaprofenico	ChEBI
Acidum tiaprofenicum	ChEBI
alpha-Methyl-5-benzoyl-2-thienylacetic acid	ChEBI
Tiaprofensaeure	ChEBI
Surgam	Kegg
2-(5-Benzoyl-thiophen-2-yl)-propionate	Generator
5-Benzoyl-a-methyl-2-thiopheneacetate	Generator
5-Benzoyl-a-methyl-2-thiopheneacetic acid	Generator
5-Benzoyl-alpha-methyl-2-thiopheneacetate	Generator
5-Benzoyl-α-methyl-2-thiopheneacetate	Generator
5-Benzoyl-α-methyl-2-thiopheneacetic acid	Generator
5-Benzoyl-a-methylthiophene-2-acetate	Generator
5-Benzoyl-a-methylthiophene-2-acetic acid	Generator
5-Benzoyl-alpha-methylthiophene-2-acetate	Generator
5-Benzoyl-α-methylthiophene-2-acetate	Generator
5-Benzoyl-α-methylthiophene-2-acetic acid	Generator
a-Methyl-5-benzoyl-2-thienylacetate	Generator
a-Methyl-5-benzoyl-2-thienylacetic acid	Generator
alpha-Methyl-5-benzoyl-2-thienylacetate	Generator
Α-methyl-5-benzoyl-2-thienylacetate	Generator
Α-methyl-5-benzoyl-2-thienylacetic acid	Generator
Tiaprofenate	Generator
Flanid	HMDB
Novo-tiaprofenic	HMDB
Novopharm brand OF tiaprofenic acid	HMDB
Nu-pharm brand OF tiaprofenic acid	HMDB
Apotex brand OF tiaprofenic acid	HMDB
Florizel brand OF tiaprofenic acid	HMDB
Nu-tiaprofenic	HMDB
PMS-Tiaprofenic	HMDB
Pierre fabre brand OF tiaprofenic acid	HMDB
Surgam sa	HMDB
Hoechst brand OF tiaprofenic acid	HMDB
Tiaprofenic acid, calcium salt	HMDB
Apo-tiaprofenic	HMDB
Aventis brand OF tiaprofenic acid	HMDB
Grünenthal brand OF tiaprofenic acid	HMDB
Pharmascience brand OF tiaprofenic acid	HMDB

Chemical Formula

C₁₄H₁₂O₃S

Average Molecular Weight

260.308

Monoisotopic Molecular Weight

260.05071494

IUPAC Name

2-(5-benzoylthiophen-2-yl)propanoic acid

Traditional Name

tiaprofenic acid

CAS Registry Number

33005-95-7

SMILES

CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17)

InChI Key

GUHPRPJDBZHYCJ-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
Thiophene carboxylic acid or derivatives
Benzoyl
2,5-disubstituted thiophene
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Thiophene
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:32221 )
thiophenes (CHEBI:32221 )
aromatic ketone (CHEBI:32221 )

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: HMDB0015538)
Membrane (HMDB: HMDB0015538)

Source

Exogenous

Exogenous (HMDB: HMDB0015538)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Tiaprofenic Acid Action Pathway (PathBank: SMP0000705)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	96 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.032 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	155.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	3.22	ALOGPS
logP	3.66	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-7.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.19 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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]+	161.592	31661259
DarkChem	[M-H]-	156.36	31661259
DeepCCS	[M+H]+	158.812	30932474
DeepCCS	[M-H]-	156.436	30932474
DeepCCS	[M-2H]-	189.325	30932474
DeepCCS	[M+Na]+	164.887	30932474
AllCCS	[M+H]+	157.2	32859911
AllCCS	[M+H-H2O]+	153.3	32859911
AllCCS	[M+NH4]+	160.8	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	158.9	32859911
AllCCS	[M+Na-2H]-	158.6	32859911
AllCCS	[M+HCOO]-	158.4	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.	7.48 minutes	32390414
Predicted by Siyang on May 30, 2022	14.4391 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2164.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	450.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	249.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	208.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	571.1 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	725.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	100.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1214.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	488.2 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	1407.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	420.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	383.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	345.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	46.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tiaprofenic acid	CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1	3352.2	Standard polar	33892256
Tiaprofenic acid	CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1	2086.6	Standard non polar	33892256
Tiaprofenic acid	CC(C(O)=O)C1=CC=C(S1)C(=O)C1=CC=CC=C1	2310.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tiaprofenic acid,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(C(=O)C2=CC=CC=C2)S1	2302.9	Semi standard non polar	33892256
Tiaprofenic acid,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(=O)C2=CC=CC=C2)S1	2576.5	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 - Tiaprofenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0940000000-af8bb733f12381a53b77	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiaprofenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0avi-9841000000-6fb4e6ade76555e66361	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiaprofenic 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 - Tiaprofenic acid LC-ESI-qTof , Positive-QTOF	splash10-0a5i-3910000000-04c8e1561815c7f17b73	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tiaprofenic acid , positive-QTOF	splash10-0a5i-3910000000-04c8e1561815c7f17b73	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Positive-QTOF	splash10-03dl-1290000000-4ce6a76b25a3d1ea274f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Positive-QTOF	splash10-0a4i-1940000000-e88e22a1c68d10055499	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Positive-QTOF	splash10-0a4i-4900000000-a38f06fe68a7ee88e176	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Negative-QTOF	splash10-0a4i-0290000000-af1e36a58a2463253634	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Negative-QTOF	splash10-0aor-2590000000-dbee76c4fb0af7803d2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Negative-QTOF	splash10-0209-9600000000-b93bd531d72f525db783	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Positive-QTOF	splash10-03di-0190000000-4f1c21443d308d90a750	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Positive-QTOF	splash10-0bt9-0950000000-471acf2d473bc63acf2d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Positive-QTOF	splash10-0bvi-5900000000-3d36668b5e4c2ad9932d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 10V, Negative-QTOF	splash10-0a4i-0290000000-5f4a79f89b41db1b6891	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 20V, Negative-QTOF	splash10-066r-3690000000-a8ca17657d6b336059d2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiaprofenic acid 40V, Negative-QTOF	splash10-055r-4900000000-65cdb9866d1499986d32	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tiaprofenic 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 DB01600	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01600	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01600

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tiaprofenic_acid

METLIN ID

Not Available

PubChem Compound

5468

PDB ID

Not Available

ChEBI ID

32221

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Brandt KD, Albrecht ME, Kalasinski LA: Effects of tiaprofenic acid on the concentration and metabolism of proteoglycans in normal and degenerating canine articular cartilage. J Clin Pharmacol. 1990 Sep;30(9):808-14. [PubMed:2277128 ]
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

Patrignani P: Aspirin insensitive eicosanoid biosynthesis in cardiovascular disease. Thromb Res. 2003 Jun 15;110(5-6):281-6. [PubMed:14592549 ]
Gupta K, Kaub CJ, Carey KN, Casillas EG, Selinsky BS, Loll PJ: Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors. Bioorg Med Chem Lett. 2004 Feb 9;14(3):667-71. [PubMed:14741265 ]
Martic M, Tatic I, Markovic S, Kujundzic N, Kostrun S: Synthesis, biological activity and molecular modeling studies of novel COX-1 inhibitors. Eur J Med Chem. 2004 Feb;39(2):141-51. [PubMed:14987823 ]
Hillarp A: [Acetylsalicylic acid resistance--clinical diagnosis with unclear mechanism]. Lakartidningen. 2004 Nov 4;101(45):3504-6, 3508-9. [PubMed:15575422 ]

Showing metabocard for Tiaprofenic acid (HMDB0015538)

MOL for HMDB0015538 (Tiaprofenic acid)

3D MOL for HMDB0015538 (Tiaprofenic acid)

3D SDF for HMDB0015538 (Tiaprofenic acid)

3D-SDF for HMDB0015538 (Tiaprofenic acid)

PDB for HMDB0015538 (Tiaprofenic acid)

3D PDB for HMDB0015538 (Tiaprofenic acid)

SMILES for HMDB0015538 (Tiaprofenic acid)

INCHI for HMDB0015538 (Tiaprofenic acid)

Structure for HMDB0015538 (Tiaprofenic acid)

3D Structure for HMDB0015538 (Tiaprofenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References