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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5)transporters (5) Show 10 proteins XML

enzymes (5)transporters (5) Show 10 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015144

Secondary Accession Numbers

HMDB15144

Metabolite Identification

Common Name

Ketoprofen

Description

Ketoprofen is only found in individuals that have used or taken this drug. It is a propionic acid derivative and is a nonsteroidal anti-inflammatory agent (NSAIA) with analgesic and antipyretic properties. The anti-inflammatory effects of ketoprofen are believed to be due to inhibition cylooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever and inflammation. Ketoprofen is a non-specific cyclooxygenase inhibitor and inhibition of COX-1 is thought to confer some of its side effects, such as GI upset and ulceration. Ketoprofen is thought to have anti-bradykinin activity, as well as lysosomal membrane-stabilizing action. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.

Structure

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

HMDB0015144
     RDKit          3D
Ketoprofen
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.3458   -0.1554   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -0.2314    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7704    0.9757    1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    0.8929    2.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    2.2457    0.6711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614   -0.6144    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577   -1.9607   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -2.3943   -0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4584   -1.4578   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.1083   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    0.8794   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673    1.9994   -1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5899    0.6583   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    1.3290   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    1.1589   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2321    0.2934    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419   -0.3955    1.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285   -0.1859    0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1558    0.3113   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1920    0.5580   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    0.1880   -1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7723   -1.1410   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0590   -1.0814    0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018    2.7931    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -2.7450    0.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -3.4373   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733   -1.8158   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340    1.9963   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.6947   -0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2656    0.1589    0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4353   -1.0650    2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1476   -0.7120    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587    1.3680   -0.1792 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10 19  2  0
 19  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

1009
  Mrv0541 02231215102D          

 19 20  0  0  1  0            999 V2000
    1.6500   -2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 12  2  0  0  0  0
  3 13  2  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  2  0  0  0  0
  7 12  1  0  0  0  0
  8 11  2  0  0  0  0
 10 11  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015144

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

> <INCHI_KEY>
DKYWVDODHFEZIM-UHFFFAOYSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.2806

> <EXACT_MASS>
254.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.56281844636002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-benzoylphenyl)propanoic acid

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
3.613333421

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.882608970976492

> <JCHEM_PKA_STRONGEST_BASIC>
-7.457434189163898

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
72.51560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ketoprofen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015144
     RDKit          3D
Ketoprofen
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.3458   -0.1554   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -0.2314    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7704    0.9757    1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    0.8929    2.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    2.2457    0.6711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614   -0.6144    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577   -1.9607   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -2.3943   -0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4584   -1.4578   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.1083   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    0.8794   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673    1.9994   -1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5899    0.6583   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    1.3290   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    1.1589   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2321    0.2934    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419   -0.3955    1.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285   -0.1859    0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1558    0.3113   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1920    0.5580   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    0.1880   -1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7723   -1.1410   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0590   -1.0814    0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018    2.7931    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -2.7450    0.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -3.4373   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733   -1.8158   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340    1.9963   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.6947   -0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2656    0.1589    0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4353   -1.0650    2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1476   -0.7120    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587    1.3680   -0.1792 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10 19  2  0
 19  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1009                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -4.528   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748   3.172   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748  -4.528   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.414  -2.218   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -1.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   0.862   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -2.218   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -1.448   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   0.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -1.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081   2.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415   3.172   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   4.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   2.402   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   5.483   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   3.172   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   4.713   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    5    9   13                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   10   12                                                  
CONECT    8    5   11                                                       
CONECT    9    4                                                            
CONECT   10    7   11                                                       
CONECT   11    8   10                                                       
CONECT   12    2    7   14                                                  
CONECT   13    1    3    4                                                  
CONECT   14   12   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015144
HETATM    1  C1  UNL     1      -4.346  -0.155  -1.108  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.565  -0.231   0.227  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.770   0.976   1.013  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.393   0.893   2.094  1.00  0.00           O  
HETATM    5  O2  UNL     1      -3.334   2.246   0.671  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.161  -0.614   0.004  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.858  -1.961  -0.000  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.559  -2.394  -0.181  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.458  -1.458  -0.362  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.169  -0.108  -0.360  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.217   0.879  -0.508  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.867   1.999  -1.014  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.590   0.658  -0.116  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.629   1.329  -0.762  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.960   1.159  -0.391  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.232   0.293   0.654  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.242  -0.396   1.328  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.928  -0.186   0.911  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.156   0.311  -0.175  1.00  0.00           C  
HETATM   20  H1  UNL     1      -5.192   0.558  -0.913  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.668   0.188  -1.906  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.772  -1.141  -1.366  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.059  -1.081   0.741  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.702   2.793   1.196  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.596  -2.745   0.131  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.282  -3.437  -0.189  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.473  -1.816  -0.512  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.434   1.996  -1.562  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.724   1.695  -0.920  1.00  0.00           H  
HETATM   30  H11 UNL     1       6.266   0.159   0.950  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.435  -1.065   2.133  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.148  -0.712   1.439  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.359   1.368  -0.179  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    6   23
CONECT    3    4    4    5
CONECT    5   24
CONECT    6    7    7   19
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   27
CONECT   10   11   19   19
CONECT   11   12   12   13
CONECT   13   14   14   18
CONECT   14   15   28
CONECT   15   16   16   29
CONECT   16   17   30
CONECT   17   18   18   31
CONECT   18   32
CONECT   19   33
END

HMDB0015144
     RDKit          3D
Ketoprofen
 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.3458   -0.1554   -1.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -0.2314    0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7704    0.9757    1.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    0.8929    2.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342    2.2457    0.6711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614   -0.6144    0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577   -1.9607   -0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -2.3943   -0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4584   -1.4578   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.1083   -0.3604 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2168    0.8794   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673    1.9994   -1.0142 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5899    0.6583   -0.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    1.3290   -0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9600    1.1589   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2321    0.2934    0.6543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419   -0.3955    1.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9285   -0.1859    0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1558    0.3113   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1920    0.5580   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    0.1880   -1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7723   -1.1410   -1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0590   -1.0814    0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018    2.7931    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5962   -2.7450    0.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2825   -3.4373   -0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4733   -1.8158   -0.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340    1.9963   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.6947   -0.9195 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2656    0.1589    0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4353   -1.0650    2.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1476   -0.7120    1.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587    1.3680   -0.1792 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  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 10 19  2  0
 19  6  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3-Benzoylphenyl)propionic acid	ChEBI
3-Benzoyl-alpha-methylbenzeneacetic acid	ChEBI
3-Benzoylhydratropic acid	ChEBI
L'acide (benzoyl-3-phenyl)-2-propionique	ChEBI
m-Benzoylhydratropic acid	ChEBI
Orudis	ChEBI
2-(3-Benzoylphenyl)propionate	Generator
3-Benzoyl-a-methylbenzeneacetate	Generator
3-Benzoyl-a-methylbenzeneacetic acid	Generator
3-Benzoyl-alpha-methylbenzeneacetate	Generator
3-Benzoyl-α-methylbenzeneacetate	Generator
3-Benzoyl-α-methylbenzeneacetic acid	Generator
3-Benzoylhydratropate	Generator
m-Benzoylhydratropate	Generator
Alrheumum	HMDB
Profenid	HMDB
Benzoylhydratropic acid	HMDB
Alrheumat	HMDB

Chemical Formula

C₁₆H₁₄O₃

Average Molecular Weight

254.2806

Monoisotopic Molecular Weight

254.094294314

IUPAC Name

2-(3-benzoylphenyl)propanoic acid

Traditional Name

ketoprofen

CAS Registry Number

22071-15-4

SMILES

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

InChI Identifier

InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)

InChI Key

DKYWVDODHFEZIM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Aryl-phenylketone
Diphenylmethane
2-phenylpropanoic-acid
Benzoyl
Aryl ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzophenones (CHEBI:6128 )
oxo monocarboxylic acid (CHEBI:6128 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)
Saliva (HMDB: HMDB0015144)

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ketoprofen Action Pathway (PathBank: SMP0000085)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.021 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	157.528	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000738

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.29	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.88	ChemAxon
pKa (Strongest Basic)	-7.5	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	72.52 m³·mol⁻¹	ChemAxon
Polarizability	26.56 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]+	160.373	31661259
DarkChem	[M-H]-	159.125	31661259
DeepCCS	[M+H]+	159.633	30932474
DeepCCS	[M-H]-	157.237	30932474
DeepCCS	[M-2H]-	190.122	30932474
DeepCCS	[M+Na]+	165.687	30932474
AllCCS	[M+H]+	158.1	32859911
AllCCS	[M+H-H2O]+	154.1	32859911
AllCCS	[M+NH4]+	161.8	32859911
AllCCS	[M+Na]+	162.8	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	160.6	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ketoprofen	CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1	3645.2	Standard polar	33892256
Ketoprofen	CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1	2098.3	Standard non polar	33892256
Ketoprofen	CC(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1	2212.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ketoprofen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=CC(C(=O)C2=CC=CC=C2)=C1	2264.5	Semi standard non polar	33892256
Ketoprofen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC(C(=O)C2=CC=CC=C2)=C1	2502.4	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 - Ketoprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1940000000-744c69e493f69a265182	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketoprofen GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9852000000-3751805b2d0db496fd23	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketoprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketoprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketoprofen GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-qTof , Positive-QTOF	splash10-0a4i-2490000000-437617eb0a03874b42b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0490000000-39b45e31d0deb851ba88	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-qTof , Positive-QTOF	splash10-0aor-2910000000-ce9fd80bd5fab07e7b9e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0390000000-a31eea165d399e00a838	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-520a79bdaf7ce3ec476c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-3aa1f85f9b6550cc9147	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-d582a4bd39cf003e73e3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-5a1b8d289986b0103991	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0390000000-66208a90d621bcbafe58	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0002-0900000000-e3e8663a70e4a78219d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0090000000-adc690db13d79d7e088b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0090000000-dc927e8f8991af0b9c62	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-QTOF , negative-QTOF	splash10-0a4i-0090000000-2f4539685044ce030904	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-QFT , negative-QTOF	splash10-0002-0900000000-ef4640dd80e9b12e93de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0090000000-c153f6a533277453ee05	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-ITFT , negative-QTOF	splash10-0a4i-0090000000-b4720ed0a7abab74acb0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0090000000-e4776b39ad9777a106d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0190000000-cd73850fa213100eea4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketoprofen LC-ESI-QTOF , positive-QTOF	splash10-0a6u-0940000000-b2b661b497cc37bb54d7	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoprofen 10V, Positive-QTOF	splash10-0a4i-0290000000-4768d924931af7c45544	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoprofen 20V, Positive-QTOF	splash10-0a4i-0960000000-15decdbeb8a53d876f13	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoprofen 40V, Positive-QTOF	splash10-0pc0-1900000000-d495168bad218af121c3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoprofen 10V, Negative-QTOF	splash10-0udi-0090000000-308307494d5069767ed6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoprofen 20V, Negative-QTOF	splash10-0pb9-0290000000-2f3d07212d1e75aaeec3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketoprofen 40V, Negative-QTOF	splash10-0kcr-5920000000-b52dbdf1eacfc9bd9a6a	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Saliva
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ketoprofen Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01009	21059682	details
Saliva	Detected and Quantified	0.688 +/- 0.530 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.425 +/- 0.279 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01009	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01009

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3693

KEGG Compound ID

C01716

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ketoprofen

METLIN ID

Not Available

PubChem Compound

3825

PDB ID

Not Available

ChEBI ID

6128

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)

Download (PDF)

General References

Kantor TG: Ketoprofen: a review of its pharmacologic and clinical properties. Pharmacotherapy. 1986 May-Jun;6(3):93-103. [PubMed:3526298 ]
Mazieres B: Topical ketoprofen patch. Drugs R D. 2005;6(6):337-44. [PubMed:16274258 ]

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

Kay-Mugford P, Benn SJ, LaMarre J, Conlon P: In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs. Am J Vet Res. 2000 Jul;61(7):802-10. [PubMed:10895904 ]
Sommerauer M, Ates M, Guhring H, Brune K, Amann R, Peskar BA: Ketoprofen-induced cyclooxygenase inhibition in renal medulla and platelets of rats treated with caffeine. Pharmacology. 2001;63(4):234-9. [PubMed:11729362 ]
Levoin N, Chretien F, Lapicque F, Chapleur Y: Synthesis and biological testing of Acyl-CoA-ketoprofen conjugates as selective irreversible inhibitors of COX-2. Bioorg Med Chem. 2002 Mar;10(3):753-7. [PubMed:11814865 ]
Zuniga J, Fuenzalida M, Guerrero A, Illanes J, Dabancens A, Diaz E, Lemus D: Effects of steroidal and non steroidal drugs on the neovascularization response induced by tumoral TA3 supernatant on CAM from chick embryo. Biol Res. 2003;36(2):233-40. [PubMed:14513718 ]
Wilson JE, Chandrasekharan NV, Westover KD, Eager KB, Simmons DL: Determination of expression of cyclooxygenase-1 and -2 isozymes in canine tissues and their differential sensitivity to nonsteroidal anti-inflammatory drugs. Am J Vet Res. 2004 Jun;65(6):810-8. [PubMed:15198222 ]
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

Parsadaniantz SM, Lebeau A, Duval P, Grimaldi B, Terlain B, Kerdelhue B: Effects of the inhibition of cyclo-oxygenase 1 or 2 or 5-lipoxygenase on the activation of the hypothalamic-pituitary-adrenal axis induced by interleukin-1beta in the male Rat. J Neuroendocrinol. 2000 Aug;12(8):766-73. [PubMed:10929089 ]
Kurahashi K, Shirahase H, Nakamura S, Tarumi T, Koshino Y, Wang AM, Nishihashi T, Shimizu Y: Nicotine-induced contraction in the rat coronary artery: possible involvement of the endothelium, reactive oxygen species and COX-1 metabolites. J Cardiovasc Pharmacol. 2001 Oct;38 Suppl 1:S21-5. [PubMed:11811354 ]
Zuniga J, Fuenzalida M, Guerrero A, Illanes J, Dabancens A, Diaz E, Lemus D: Effects of steroidal and non steroidal drugs on the neovascularization response induced by tumoral TA3 supernatant on CAM from chick embryo. Biol Res. 2003;36(2):233-40. [PubMed:14513718 ]
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 ]
Levoin N, Blondeau C, Guillaume C, Grandcolas L, Chretien F, Jouzeau JY, Benoit E, Chapleur Y, Netter P, Lapicque F: Elucidation of the mechanism of inhibition of cyclooxygenases by acyl-coenzyme A and acylglucuronic conjugates of ketoprofen. Biochem Pharmacol. 2004 Nov 15;68(10):1957-69. [PubMed:15476667 ]

Enzyme Details

3. Cytochrome P450 2C9

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

References

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

Enzyme Details

4. Cytochrome P450 2C8

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

References

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

Enzyme Details

5. C-X-C chemokine receptor type 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor to interleukin-8, which is a powerful neutrophils chemotactic factor. Binding of IL-8 to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activate a phosphatidylinositol-calcium second messenger system. This receptor binds to IL-8 with a high affinity and to MGSA (GRO) with a low affinity
Gene Name:: CXCR1
Uniprot ID:: P25024
Molecular weight:: 39790.7

References

Allegretti M, Bertini R, Cesta MC, Bizzarri C, Di Bitondo R, Di Cioccio V, Galliera E, Berdini V, Topai A, Zampella G, Russo V, Di Bello N, Nano G, Nicolini L, Locati M, Fantucci P, Florio S, Colotta F: 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. J Med Chem. 2005 Jun 30;48(13):4312-31. [PubMed:15974585 ]
Bizzarri C, Pagliei S, Brandolini L, Mascagni P, Caselli G, Transidico P, Sozzani S, Bertini R: Selective inhibition of interleukin-8-induced neutrophil chemotaxis by ketoprofen isomers. Biochem Pharmacol. 2001 Jun 1;61(11):1429-37. [PubMed:11331079 ]
Wang LM, Toyoshima A, Mineshita S, Wang XX, Yamamoto T, Nomura Y, Yang L, Koikei Y, Shiba K, Honda Y: The anti-inflammatory effects of ketoprofen in animal experiments. Drugs Exp Clin Res. 1997;23(1):1-6. [PubMed:9093816 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]

Enzyme Details

2. Solute carrier organic anion transporter family member 1A2

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:: SLCO1A2
Uniprot ID:: P46721
Molecular weight:: 74144.1

References

Shitara Y, Sugiyama D, Kusuhara H, Kato Y, Abe T, Meier PJ, Itoh T, Sugiyama Y: Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport. Pharm Res. 2002 Feb;19(2):147-53. [PubMed:11883641 ]

Enzyme Details

3. Multidrug resistance-associated protein 4

General function:: Involved in ATP binding
Specific function:: May be an organic anion pump relevant to cellular detoxification
Gene Name:: ABCC4
Uniprot ID:: O15439
Molecular weight:: 149525.3

References

Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, Wijnholds J, Borst P: The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9244-9. Epub 2003 Jun 30. [PubMed:12835412 ]

Enzyme Details

4. 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

Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [PubMed:10929807 ]
Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [PubMed:11099697 ]
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 ]

Enzyme Details

5. Solute carrier family 22 member 7

General function:: Involved in transmembrane transport
Specific function:: Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:: SLC22A7
Uniprot ID:: Q9Y694
Molecular weight:: 60025.0

References

Sekine T, Cha SH, Tsuda M, Apiwattanakul N, Nakajima N, Kanai Y, Endou H: Identification of multispecific organic anion transporter 2 expressed predominantly in the liver. FEBS Lett. 1998 Jun 12;429(2):179-82. [PubMed:9650585 ]
Morita N, Kusuhara H, Sekine T, Endou H, Sugiyama Y: Functional characterization of rat organic anion transporter 2 in LLC-PK1 cells. J Pharmacol Exp Ther. 2001 Sep;298(3):1179-84. [PubMed:11504818 ]
Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]

Showing metabocard for Ketoprofen (HMDB0015144)

MOL for HMDB0015144 (Ketoprofen)

3D MOL for HMDB0015144 (Ketoprofen)

3D SDF for HMDB0015144 (Ketoprofen)

3D-SDF for HMDB0015144 (Ketoprofen)

PDB for HMDB0015144 (Ketoprofen)

3D PDB for HMDB0015144 (Ketoprofen)

SMILES for HMDB0015144 (Ketoprofen)

INCHI for HMDB0015144 (Ketoprofen)

Structure for HMDB0015144 (Ketoprofen)

3D Structure for HMDB0015144 (Ketoprofen)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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