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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:45:11 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041873

Secondary Accession Numbers

HMDB41873

Metabolite Identification

Common Name

Dexketoprofen

Description

Dexketoprofen belongs to a class of medicines called non-steroidal anti-inflammatory drugs (NSAIDs). It works by blocking the action of a substance in the body called cyclo-oxygenase. Cyclo-oxygenase is involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would otherwise go on to cause swelling, inflammation and pain. By blocking cyclo-oxygenase, dexketoprofen prevents the production of prostaglandins and therefore reduces inflammation and pain. Along with Peripheral analgesic action it possesses central analgesic action. Dexketoprofen is a non-steroidal anti-inflammatory drug. It is manufactured by Menarini, under the tradename Keral. It is available in the UK, as dexketoprofen trometamol, as a prescription-only drug and in Latin America as Miracox, produced by Stein in Costa Rica. In Italy it is available as an over the counter-drug under the tradename Enantyum. In Lithuania it is available as over the counter-drug uder tradename Dolmen.

Structure

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

HMDB0041873
     RDKit          3D
Dexketoprofen
 33 34  0  0  0  0  0  0  0  0999 V2000
    2.9843    0.8219    1.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    0.4510    0.0441 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5441    1.5624   -0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    1.4303   -1.5759 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    2.7855   -0.8302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -0.6833   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110   -1.8798   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -2.9561   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3264   -2.8134   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -1.6242   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -1.5562    0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2371   -2.6488    0.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4479   -0.3572    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5761   -0.2841    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993    0.8208    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024    1.9052    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.8180   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.7152   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6570   -0.5747    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9026   -0.1212    2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9272    1.3028    1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861    1.4297    1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786    0.1426   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191    3.6174   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -1.9773   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -3.8752   -1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -3.6604   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560   -1.1265    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2959    0.8627    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603    2.7468    0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    2.6752   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    0.6989   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.3519    0.4670 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  6
  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


  Mrv0541 10051212212D          

 20 21  0  0  0  0            999 V2000
   -0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 11  1  1  6  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  2  0  0  0  0
 19 16  1  0  0  0  0
 11 20  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0041873

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](C)(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)/t11-/m0/s1

> <INCHI_KEY>
DKYWVDODHFEZIM-NSHDSACASA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.2806

> <EXACT_MASS>
254.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.882988750740438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-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>
54.370000000000005

> <JCHEM_REFRACTIVITY>
72.51559999999999

> <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

$$$$

HMDB0041873
     RDKit          3D
Dexketoprofen
 33 34  0  0  0  0  0  0  0  0999 V2000
    2.9843    0.8219    1.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    0.4510    0.0441 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5441    1.5624   -0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    1.4303   -1.5759 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    2.7855   -0.8302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -0.6833   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110   -1.8798   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -2.9561   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3264   -2.8134   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -1.6242   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -1.5562    0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2371   -2.6488    0.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4479   -0.3572    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5761   -0.2841    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993    0.8208    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024    1.9052    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.8180   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.7152   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6570   -0.5747    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9026   -0.1212    2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9272    1.3028    1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861    1.4297    1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786    0.1426   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191    3.6174   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -1.9773   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -3.8752   -1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -3.6604   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560   -1.1265    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2959    0.8627    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603    2.7468    0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    2.6752   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    0.6989   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.3519    0.4670 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  6
  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                                 05-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    3   12                                                       
CONECT    7    4   12                                                       
CONECT    8    5   13                                                       
CONECT    9    5   14                                                       
CONECT   10   13   14                                                       
CONECT   11    1   13   16   20                                             
CONECT   12    6    7   15                                                  
CONECT   13    8   10   11                                                  
CONECT   14    9   10   15                                                  
CONECT   15   12   14   17                                                  
CONECT   16   11   18   19                                                  
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   11                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0041873
HETATM    1  C1  UNL     1       2.984   0.822   1.506  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.939   0.451   0.044  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.544   1.562  -0.820  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.550   1.430  -1.576  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.249   2.785  -0.830  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.015  -0.683  -0.166  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.511  -1.880  -0.633  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.668  -2.956  -0.839  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.326  -2.813  -0.569  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.214  -1.624  -0.097  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.640  -1.556   0.171  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.237  -2.649   0.480  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.448  -0.357   0.120  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.576  -0.284   0.904  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.399   0.821   0.904  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.102   1.905   0.098  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.971   1.818  -0.682  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.143   0.715  -0.686  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.657  -0.575   0.095  1.00  0.00           C  
HETATM   20  H1  UNL     1       2.903  -0.121   2.086  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.927   1.303   1.763  1.00  0.00           H  
HETATM   22  H3  UNL     1       2.086   1.430   1.748  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.979   0.143  -0.225  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.719   3.617  -1.063  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.571  -1.977  -0.842  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.094  -3.875  -1.205  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.326  -3.660  -0.732  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.856  -1.126   1.567  1.00  0.00           H  
HETATM   29  H10 UNL     1      -5.296   0.863   1.536  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.760   2.747   0.120  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.751   2.675  -1.309  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.250   0.699  -1.337  1.00  0.00           H  
HETATM   33  H14 UNL     1       0.247   0.352   0.467  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

HMDB0041873
     RDKit          3D
Dexketoprofen
 33 34  0  0  0  0  0  0  0  0999 V2000
    2.9843    0.8219    1.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9389    0.4510    0.0441 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5441    1.5624   -0.8198 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    1.4303   -1.5759 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    2.7855   -0.8302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0147   -0.6833   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110   -1.8798   -0.6334 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6678   -2.9561   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3264   -2.8134   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -1.6242   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -1.5562    0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2371   -2.6488    0.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4479   -0.3572    0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5761   -0.2841    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3993    0.8208    0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024    1.9052    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.8180   -0.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432    0.7152   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6570   -0.5747    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9026   -0.1212    2.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9272    1.3028    1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861    1.4297    1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786    0.1426   -0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7191    3.6174   -1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -1.9773   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939   -3.8752   -1.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3264   -3.6604   -0.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560   -1.1265    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2959    0.8627    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603    2.7468    0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    2.6752   -1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2500    0.6989   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.3519    0.4670 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  6
  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
(+)-(S)-m-Benzoylhydratropic acid	ChEBI
(+)-3-Benzoylhydratropic acid	ChEBI
(+)-Ketoprofen	ChEBI
(S)-3-Benzoyl-alpha-methylbenzeneacetic acid	ChEBI
(S)-Ketoprofen	ChEBI
(+)-(S)-m-Benzoylhydratropate	Generator
(+)-3-Benzoylhydratropate	Generator
(S)-3-Benzoyl-a-methylbenzeneacetate	Generator
(S)-3-Benzoyl-a-methylbenzeneacetic acid	Generator
(S)-3-Benzoyl-alpha-methylbenzeneacetate	Generator
(S)-3-Benzoyl-α-methylbenzeneacetate	Generator
(S)-3-Benzoyl-α-methylbenzeneacetic acid	Generator
Badyket	HMDB
Quiralam	HMDB
Keral	HMDB
Sympal	HMDB
Ketesse	HMDB
Enangel	HMDB
Enantyum	HMDB
Adolquir	HMDB
Quirgel	HMDB
Dexketoprofen trometamol	HMDB

Chemical Formula

C₁₆H₁₄O₃

Average Molecular Weight

254.2806

Monoisotopic Molecular Weight

254.094294314

IUPAC Name

(2S)-2-(3-benzoylphenyl)propanoic acid

Traditional Name

(+)-ketoprofen

CAS Registry Number

22161-81-5

SMILES

[H][C@@](C)(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)/t11-/m0/s1

InChI Key

DKYWVDODHFEZIM-NSHDSACASA-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:76128 )
monocarboxylic acid (CHEBI:76128 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041873)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

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	26.88 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]+	161.598	31661259
DarkChem	[M-H]-	157.138	31661259
DeepCCS	[M+H]+	161.239	30932474
DeepCCS	[M-H]-	158.882	30932474
DeepCCS	[M-2H]-	192.885	30932474
DeepCCS	[M+Na]+	168.063	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.1	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.7	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
Dexketoprofen	[H][C@@](C)(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1	3610.6	Standard polar	33892256
Dexketoprofen	[H][C@@](C)(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1	2102.2	Standard non polar	33892256
Dexketoprofen	[H][C@@](C)(C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1	2227.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dexketoprofen,1TMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C)C1=CC=CC(C(=O)C2=CC=CC=C2)=C1	2266.1	Semi standard non polar	33892256
Dexketoprofen,1TBDMS,isomer #1	C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC(C(=O)C2=CC=CC=C2)=C1	2499.3	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 - Dexketoprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1940000000-f7bd8f8c00db90255ec4	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexketoprofen GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9852000000-3751805b2d0db496fd23	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexketoprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexketoprofen 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 - Dexketoprofen LC-ESI-qTof , Positive-QTOF	splash10-0a4i-3910000000-1bfe148d4ab6af381e80	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexketoprofen , positive-QTOF	splash10-0a4i-3910000000-1bfe148d4ab6af381e80	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 10V, Positive-QTOF	splash10-0a4i-0290000000-4768d924931af7c45544	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 20V, Positive-QTOF	splash10-0a4i-0960000000-15decdbeb8a53d876f13	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 40V, Positive-QTOF	splash10-0pc0-1900000000-d495168bad218af121c3	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 10V, Negative-QTOF	splash10-0udi-0090000000-308307494d5069767ed6	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 20V, Negative-QTOF	splash10-0pb9-0290000000-2f3d07212d1e75aaeec3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 40V, Negative-QTOF	splash10-0kcr-5920000000-b52dbdf1eacfc9bd9a6a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 10V, Positive-QTOF	splash10-0a4i-0290000000-01427ffe174426164dca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 20V, Positive-QTOF	splash10-0a4i-0980000000-6adc02672decadc11a7f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 40V, Positive-QTOF	splash10-057i-4900000000-246c2457778cde32361d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 10V, Negative-QTOF	splash10-0a4i-0090000000-6eca0663b2d1b5b3602c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 20V, Negative-QTOF	splash10-0a4i-0290000000-969020a191c2b838c93e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexketoprofen 40V, Negative-QTOF	splash10-001i-1930000000-331855e095a6b968e27e	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB09214

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

580922

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dexketoprofen

METLIN ID

Not Available

PubChem Compound

177976

PDB ID

Not Available

ChEBI ID

76128

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

Miranda HF, Romero MA, Puig MM: Antinociceptive and anti-exudative synergism between dexketoprofen and tramadol in a model of inflammatory pain in mice. Fundam Clin Pharmacol. 2012 Jun;26(3):373-82. doi: 10.1111/j.1472-8206.2010.00922.x. Epub 2011 Jan 25. [PubMed:22081874 ]
Vera P, Zapata L, Gich I, Mancebo J, Betbese AJ: [Hemodynamic and antipyretic effects of paracetamol, metamizol and dexketoprofen in critical patients]. Med Intensiva. 2012 Dec;36(9):619-25. doi: 10.1016/j.medin.2012.02.003. Epub 2012 Mar 16. [PubMed:22425338 ]
Porwal A, Mahajan AD, Oswal DS, Erram SS, Sheth DN, Balamurugan S, Kamat V, Enadle RP, Badadare A, Bhatnagar SK, Walvekar RS, Dhorepatil S, Naik RC, Basu I, Kshirsagar SN, Keny JV, Sengupta S: Efficacy and tolerability of fixed-dose combination of dexketoprofen and dicyclomine injection in acute renal colic. Pain Res Treat. 2012;2012:295926. doi: 10.1155/2012/295926. Epub 2012 Apr 23. [PubMed:22577544 ]
Ozer AB, Erhan OL, Keles E, Demirel I, Bestas A, Gunduz G: Comparison of the effects of preoperative and intraoperative intravenous application of dexketoprofen on postoperative analgesia in septorhinoplasty patients: randomised double blind clinical trial. Eur Rev Med Pharmacol Sci. 2012 Nov;16(13):1828-33. [PubMed:23208967 ]
Tunali Y, Akcil EF, Dilmen OK, Tutuncu AC, Koksal GM, Akbas S, Vehid H, Yentur E: Efficacy of intravenous paracetamol and dexketoprofen on postoperative pain and morphine consumption after a lumbar disk surgery. J Neurosurg Anesthesiol. 2013 Apr;25(2):143-7. doi: 10.1097/ANA.0b013e31827464af. [PubMed:23360885 ]
Eken C, Serinken M, Elicabuk H, Uyanik E, Erdal M: Intravenous paracetamol versus dexketoprofen versus morphine in acute mechanical low back pain in the emergency department: a randomised double-blind controlled trial. Emerg Med J. 2014 Mar;31(3):177-81. doi: 10.1136/emermed-2012-201670. Epub 2013 Feb 13. [PubMed:23407378 ]
Salman AE, Yetisir F, Yurekli B, Aksoy M, Yildirim M, Kilic M: The efficacy of the semi-blind approach of transversus abdominis plane block on postoperative analgesia in patients undergoing inguinal hernia repair: a prospective randomized double-blind study. Local Reg Anesth. 2013 Jan 18;6:1-7. doi: 10.2147/LRA.S38359. Print 2013. [PubMed:23630432 ]
Allais G, Rolando S, Schiapparelli P, Airola G, Borgogno P, Mana O, Benedetto C: Frovatriptan plus dexketoprofen in the treatment of menstrually related migraine: an open study. Neurol Sci. 2013 May;34 Suppl 1:S179-81. doi: 10.1007/s10072-013-1390-0. [PubMed:23695075 ]

Showing metabocard for Dexketoprofen (HMDB0041873)

MOL for HMDB0041873 (Dexketoprofen)

3D MOL for HMDB0041873 (Dexketoprofen)

3D SDF for HMDB0041873 (Dexketoprofen)

3D-SDF for HMDB0041873 (Dexketoprofen)

PDB for HMDB0041873 (Dexketoprofen)

3D PDB for HMDB0041873 (Dexketoprofen)

SMILES for HMDB0041873 (Dexketoprofen)

INCHI for HMDB0041873 (Dexketoprofen)

Structure for HMDB0041873 (Dexketoprofen)

3D Structure for HMDB0041873 (Dexketoprofen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra