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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015008

Secondary Accession Numbers

HMDB15008

Metabolite Identification

Common Name

Suprofen

Description

Suprofen is only found in individuals that have used or taken this drug. It is an ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. [PubChem]Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellular phospholipid bilayer by phospholipase A₂). Prostaglandins act (among other things) as messenger molecules in the process of inflammation. The overall result is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter.

Structure

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

HMDB0015008
     RDKit          3D
Suprofen
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7170   -1.3003    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505   -0.2259   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455    1.0697    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253    1.7468   -0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    1.5940    1.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -0.2752   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.2391    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322   -0.2840    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -0.3664   -1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -0.4025   -1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242   -0.8652   -2.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2419    0.1261   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5828   -0.1744   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3043    0.4357    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448    1.3055    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0462    1.2483    0.8413 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -0.4047   -2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -0.3587   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054   -2.0525    0.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464   -1.7869    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -0.9029    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9245   -0.3936   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    2.5847    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473   -0.1727    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037   -0.2594    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0127   -0.9053   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4014    0.2468    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1128    1.8722    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220   -0.4700   -3.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -0.3899   -2.5361 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
  9 17  1  0
 17 18  2  0
 18  6  1  0
 16 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
 17 29  1  0
 18 30  1  0
M  END

870
  Mrv0541 02231215042D          

 18 19  0  0  1  0            999 V2000
    3.8797    2.9274    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.8432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5471    1.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992    2.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6867    3.0989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  1 18  1  0  0  0  0
  2 13  1  0  0  0  0
  3 13  2  0  0  0  0
  4 14  2  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 13  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015008

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1

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

> <INCHI_KEY>
MDKGKXOCJGEUJW-UHFFFAOYSA-N

> <FORMULA>
C14H12O3S

> <MOLECULAR_WEIGHT>
260.308

> <EXACT_MASS>
260.05071494

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.838067657526643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.526214794

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.011917248549982

> <JCHEM_PKA_STRONGEST_BASIC>
-7.805115519476987

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
69.40550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
suprofen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015008
     RDKit          3D
Suprofen
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7170   -1.3003    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505   -0.2259   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455    1.0697    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253    1.7468   -0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    1.5940    1.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -0.2752   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.2391    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322   -0.2840    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -0.3664   -1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -0.4025   -1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242   -0.8652   -2.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2419    0.1261   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5828   -0.1744   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3043    0.4357    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448    1.3055    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0462    1.2483    0.8413 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -0.4047   -2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -0.3587   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054   -2.0525    0.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464   -1.7869    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -0.9029    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9245   -0.3936   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    2.5847    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473   -0.1727    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037   -0.2594    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0127   -0.9053   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4014    0.2468    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1128    1.8722    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220   -0.4700   -3.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -0.3899   -2.5361 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
  9 17  1  0
 17 18  2  0
 18  6  1  0
 16 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
 17 29  1  0
 18 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 870                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.242   5.464   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       4.414  -5.307   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080  -2.997   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414   3.933   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.747  -2.997   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747  -1.457   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -0.687   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.687   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.747   1.623   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -3.767   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   0.853   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   0.853   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.767   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747   3.163   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   3.933   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.488   3.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.519   4.451   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.749   5.785   0.000  0.00  0.00           C+0
CONECT    1   15   18                                                       
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    6   10   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   11                                                       
CONECT    8    6   12                                                       
CONECT    9   11   12   14                                                  
CONECT   10    5                                                            
CONECT   11    7    9                                                       
CONECT   12    8    9                                                       
CONECT   13    2    3    5                                                  
CONECT   14    4    9   15                                                  
CONECT   15    1   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    1   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015008
HETATM    1  C1  UNL     1       3.717  -1.300   0.899  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.350  -0.226  -0.076  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.745   1.070   0.482  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.625   1.747  -0.095  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.182   1.594   1.639  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.889  -0.275  -0.425  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.916  -0.239   0.549  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.432  -0.284   0.231  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.864  -0.366  -1.069  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.261  -0.403  -1.393  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.724  -0.865  -2.471  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.242   0.126  -0.430  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.583  -0.174  -0.365  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.304   0.436   0.587  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.645   1.306   1.413  1.00  0.00           C  
HETATM   16  S1  UNL     1      -3.046   1.248   0.841  1.00  0.00           S  
HETATM   17  C13 UNL     1       0.116  -0.405  -2.071  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.440  -0.359  -1.723  1.00  0.00           C  
HETATM   19  H1  UNL     1       2.905  -2.053   0.886  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.646  -1.787   0.594  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.855  -0.903   1.939  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.924  -0.394  -1.026  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.230   2.585   1.836  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.247  -0.173   1.577  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.104  -0.259   1.094  1.00  0.00           H  
HETATM   26  H8  UNL     1      -5.013  -0.905  -1.092  1.00  0.00           H  
HETATM   27  H9  UNL     1      -6.401   0.247   0.704  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.113   1.872   2.237  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.222  -0.470  -3.097  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.164  -0.390  -2.536  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   17
CONECT   10   11   11   12
CONECT   12   13   13   16
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   16   28
CONECT   17   18   18   29
CONECT   18   30
END

HMDB0015008
     RDKit          3D
Suprofen
 30 31  0  0  0  0  0  0  0  0999 V2000
    3.7170   -1.3003    0.8992 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3505   -0.2259   -0.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7455    1.0697    0.4817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253    1.7468   -0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    1.5940    1.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -0.2752   -0.4251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9159   -0.2391    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4322   -0.2840    0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8635   -0.3664   -1.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -0.4025   -1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242   -0.8652   -2.4714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2419    0.1261   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5828   -0.1744   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3043    0.4357    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6448    1.3055    1.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0462    1.2483    0.8413 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -0.4047   -2.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4402   -0.3587   -1.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9054   -2.0525    0.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6464   -1.7869    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -0.9029    1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9245   -0.3936   -1.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2295    2.5847    1.8365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473   -0.1727    1.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1037   -0.2594    1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0127   -0.9053   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4014    0.2468    0.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1128    1.8722    2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2220   -0.4700   -3.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1644   -0.3899   -2.5361 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
  9 17  1  0
 17 18  2  0
 18  6  1  0
 16 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
 17 29  1  0
 18 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-2-(p-(2-Thenoyl)phenyl)propionic acid	ChEBI
2-(4-(2-Thenoyl)phenyl)propionsaeure	ChEBI
2-[4-(Thiophene-2-carbonyl)-phenyl]-propionic acid	ChEBI
4-(2-Thenoyl)hydratropsaeure	ChEBI
alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetic acid	ChEBI
p-2-Thenoylhydratropic acid	ChEBI
PROFENAL	ChEBI
Suprofene	ChEBI
Suprofenum	ChEBI
SUTOPROFEN	ChEBI
(+-)-2-(p-(2-Thenoyl)phenyl)propionate	Generator
2-[4-(Thiophene-2-carbonyl)-phenyl]-propionate	Generator
a-Methyl-4-(2-thienylcarbonyl)benzeneacetate	Generator
a-Methyl-4-(2-thienylcarbonyl)benzeneacetic acid	Generator
alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetate	Generator
Α-methyl-4-(2-thienylcarbonyl)benzeneacetate	Generator
Α-methyl-4-(2-thienylcarbonyl)benzeneacetic acid	Generator
p-2-Thenoylhydratropate	Generator

Chemical Formula

C₁₄H₁₂O₃S

Average Molecular Weight

260.308

Monoisotopic Molecular Weight

260.05071494

IUPAC Name

2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid

Traditional Name

suprofen

CAS Registry Number

40828-46-4

SMILES

CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1

InChI Identifier

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

InChI Key

MDKGKXOCJGEUJW-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
2-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Benzoyl
Thiophene carboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Thiophene
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:9362 )
thiophenes (CHEBI:9362 )
aromatic ketone (CHEBI:9362 )

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

Source

Exogenous

Exogenous (HMDB: HMDB0015008)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Suprofen Action Pathway (PathBank: SMP0000101)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.042 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	157.205	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001313

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.53	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.01	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	69.41 m³·mol⁻¹	ChemAxon
Polarizability	26.84 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]+	160.185	31661259
DarkChem	[M-H]-	157.402	31661259
DeepCCS	[M+H]+	155.698	30932474
DeepCCS	[M-H]-	153.303	30932474
DeepCCS	[M-2H]-	186.865	30932474
DeepCCS	[M+Na]+	161.929	30932474
AllCCS	[M+H]+	157.5	32859911
AllCCS	[M+H-H2O]+	153.6	32859911
AllCCS	[M+NH4]+	161.2	32859911
AllCCS	[M+Na]+	162.2	32859911
AllCCS	[M-H]-	159.7	32859911
AllCCS	[M+Na-2H]-	159.5	32859911
AllCCS	[M+HCOO]-	159.4	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.	7.28 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4931 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.86 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	32.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1936.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	411.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	229.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	197.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	531.5 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	572.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1158.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	456.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1290.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	367.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	357.4 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	53.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Suprofen	CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1	3446.1	Standard polar	33892256
Suprofen	CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1	2159.2	Standard non polar	33892256
Suprofen	CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1	2395.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Suprofen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(C(=O)C2=CC=CS2)C=C1	2360.9	Semi standard non polar	33892256
Suprofen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(=O)C2=CC=CS2)C=C1	2620.2	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 - Suprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-03yi-3950000000-2beb7651624021d3b69c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Suprofen GC-MS (1 TMS) - 70eV, Positive	splash10-044r-9641000000-c830643d9eb20837ed21	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Suprofen 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 - Suprofen LC-ESI-qTof , Positive-QTOF	splash10-03di-2790000000-0cf8f983c8b216c951b3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Suprofen , positive-QTOF	splash10-03di-2790000000-0cf8f983c8b216c951b3	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 10V, Positive-QTOF	splash10-03di-0190000000-b385b916f83fe63a391f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 20V, Positive-QTOF	splash10-00pl-0980000000-8949c56f6ad00845d44f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 40V, Positive-QTOF	splash10-0f89-2910000000-beb45e1bbb9ee6cfb6d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 10V, Negative-QTOF	splash10-0a4i-0090000000-e899cf6b283f80af4b28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 20V, Negative-QTOF	splash10-067i-3290000000-1cda8cbaaa37e5e208a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 40V, Negative-QTOF	splash10-0a4i-9200000000-a847e351fd4eaab35709	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 10V, Positive-QTOF	splash10-03di-0190000000-673fb127704f6bfbfd7e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 20V, Positive-QTOF	splash10-03di-0920000000-ede0582b439b3c346678	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 40V, Positive-QTOF	splash10-03e9-1900000000-5ea28866f36feffd9e6d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 10V, Negative-QTOF	splash10-066r-0090000000-70f319866d1a58df3003	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 20V, Negative-QTOF	splash10-0159-4590000000-a54a62a0721f1193bafc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Suprofen 40V, Negative-QTOF	splash10-0019-4900000000-fb0e7b4c457b4f9dba0b	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Suprofen 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 DB00870	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00870	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00870

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5166

KEGG Compound ID

C07320

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Suprofen

METLIN ID

Not Available

PubChem Compound

5359

PDB ID

Not Available

ChEBI ID

9362

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. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

3. 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 ]
Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [PubMed:11885959 ]

Enzyme Details

4. 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

Loll PJ, Picot D, Ekabo O, Garavito RM: Synthesis and use of iodinated nonsteroidal antiinflammatory drug analogs as crystallographic probes of the prostaglandin H2 synthase cyclooxygenase active site. Biochemistry. 1996 Jun 11;35(23):7330-40. [PubMed:8652509 ]
Bender A, Scheiber J, Glick M, Davies JW, Azzaoui K, Hamon J, Urban L, Whitebread S, Jenkins JL: Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure. ChemMedChem. 2007 Jun;2(6):861-73. [PubMed:17477341 ]
Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [PubMed:11885959 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Cytochrome P450 2C9

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

References

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

Showing metabocard for Suprofen (HMDB0015008)

MOL for HMDB0015008 (Suprofen)

3D MOL for HMDB0015008 (Suprofen)

3D SDF for HMDB0015008 (Suprofen)

3D-SDF for HMDB0015008 (Suprofen)

PDB for HMDB0015008 (Suprofen)

3D PDB for HMDB0015008 (Suprofen)

SMILES for HMDB0015008 (Suprofen)

INCHI for HMDB0015008 (Suprofen)

Structure for HMDB0015008 (Suprofen)

3D Structure for HMDB0015008 (Suprofen)

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

References

References

References