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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014713

Secondary Accession Numbers

HMDB14713

Metabolite Identification

Common Name

Fenoprofen

Description

Fenoprofen, also known as nalfon or nalgesic, belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. A non-steroidal anti-inflammatory drug, the dihydrate form of the calcium salt is used for the management of mild to moderate pain and for the relief of pain and inflammation associated with disorders such as arthritis. Fenoprofen is a drug which is used for relief of the signs and symptoms of rheumatoid arthritis and osteoarthritis. also for the relief of mild to moderate pain. Fenoprofen is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, fenoprofen is involved in fenoprofen action pathway. A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 2 is substituted by a 3-phenoxyphenyl group. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding.

Structure

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

HMDB0014713
     RDKit          3D
Fenoprofen
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9322    1.0228   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525   -0.2840    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9213   -0.3873    1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906   -0.6182    2.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2680   -0.2237    1.7114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.4723   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -1.5032   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346   -1.7573   -1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873   -0.9168   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958    0.1324    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.9588    0.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    0.7425    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3575   -0.0739    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105   -0.2805    1.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3284    0.3498    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    1.1686   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379    1.3609   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480    0.3270    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9634    0.8443   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    1.2082   -0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2454    1.8279   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -1.0704   -0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9761   -0.0027    1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -2.1715   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -2.5803   -1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544   -1.0776   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150   -0.5862    2.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3185   -0.9188    1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3880    0.1835    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1228    1.6409   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255    2.0165   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3624    1.1406    1.0794 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  2  0
 18  6  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

573
  Mrv0541 02231214472D          

 18 19  0  0  1  0            999 V2000
    2.3645   -0.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 13  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014713

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13/h2-11H,1H3,(H,16,17)

> <INCHI_KEY>
RDJGLLICXDHJDY-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.2699

> <EXACT_MASS>
242.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.29718180937722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
3.6542675666666664

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.958974374547462

> <JCHEM_PKA_STRONGEST_BASIC>
-8.709542604441243

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
68.18090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fenoprofen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014713
     RDKit          3D
Fenoprofen
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9322    1.0228   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525   -0.2840    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9213   -0.3873    1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906   -0.6182    2.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2680   -0.2237    1.7114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.4723   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -1.5032   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346   -1.7573   -1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873   -0.9168   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958    0.1324    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.9588    0.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    0.7425    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3575   -0.0739    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105   -0.2805    1.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3284    0.3498    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    1.1686   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379    1.3609   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480    0.3270    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9634    0.8443   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    1.2082   -0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2454    1.8279   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -1.0704   -0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9761   -0.0027    1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -2.1715   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -2.5803   -1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544   -1.0776   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150   -0.5862    2.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3185   -0.9188    1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3880    0.1835    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1228    1.6409   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255    2.0165   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3624    1.1406    1.0794 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  2  0
 18  6  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 573                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.414  -1.394   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   5.536   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748   3.226   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.081   3.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   1.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   0.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   3.996   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   0.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -0.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   3.996   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -0.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -1.394   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -2.934   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -3.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -3.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -5.244   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -5.244   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -6.014   0.000  0.00  0.00           C+0
CONECT    1    9   13                                                       
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    5    7   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    9                                                       
CONECT    7    4                                                            
CONECT    8    5   11                                                       
CONECT    9    1    6   12                                                  
CONECT   10    2    3    4                                                  
CONECT   11    8   12                                                       
CONECT   12    9   11                                                       
CONECT   13    1   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0014713
HETATM    1  C1  UNL     1      -3.932   1.023  -0.601  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.453  -0.284   0.058  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.921  -0.387   1.438  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.191  -0.618   2.428  1.00  0.00           O  
HETATM    5  O2  UNL     1      -5.268  -0.224   1.711  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.016  -0.472  -0.124  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.562  -1.503  -0.918  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.235  -1.757  -1.146  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.687  -0.917  -0.535  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.296   0.132   0.270  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.250   0.959   0.870  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.603   0.743   0.669  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.358  -0.074   1.485  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.711  -0.281   1.271  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.328   0.350   0.208  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.599   1.169  -0.620  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.238   1.361  -0.385  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.048   0.327   0.455  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.963   0.844  -1.714  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.975   1.208  -0.252  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.245   1.828  -0.342  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.988  -1.070  -0.523  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.976  -0.003   1.053  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.273  -2.172  -1.404  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.116  -2.580  -1.779  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.754  -1.078  -0.686  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.915  -0.586   2.328  1.00  0.00           H  
HETATM   28  H10 UNL     1       5.318  -0.919   1.903  1.00  0.00           H  
HETATM   29  H11 UNL     1       6.388   0.183   0.046  1.00  0.00           H  
HETATM   30  H12 UNL     1       5.123   1.641  -1.440  1.00  0.00           H  
HETATM   31  H13 UNL     1       2.725   2.016  -1.074  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.362   1.141   1.079  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   26
CONECT   10   11   18   18
CONECT   11   12
CONECT   12   13   13   17
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   32
END

HMDB0014713
     RDKit          3D
Fenoprofen
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.9322    1.0228   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4525   -0.2840    0.0578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9213   -0.3873    1.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906   -0.6182    2.4276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2680   -0.2237    1.7114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0159   -0.4723   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5616   -1.5032   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2346   -1.7573   -1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873   -0.9168   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958    0.1324    0.2703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    0.9588    0.8701 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6030    0.7425    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3575   -0.0739    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105   -0.2805    1.2714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3284    0.3498    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5986    1.1686   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379    1.3609   -0.3848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0480    0.3270    0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9634    0.8443   -1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    1.2082   -0.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2454    1.8279   -0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882   -1.0704   -0.5232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9761   -0.0027    1.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2735   -2.1715   -1.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1164   -2.5803   -1.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7544   -1.0776   -0.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9150   -0.5862    2.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3185   -0.9188    1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3880    0.1835    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1228    1.6409   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255    2.0165   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3624    1.1406    1.0794 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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  2  0
 18  6  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-2-(3-Phenoxyphenyl)propionic acid	ChEBI
(+-)-m-Phenoxyhydratropic acid	ChEBI
2-(3-Phenoxyphenyl)propionic acid	ChEBI
2-(m-Phenoxyphenyl)propionic acid	ChEBI
alpha-(m-Phenoxyphenyl)propionic acid	ChEBI
alpha-Methyl-3-phenoxybenzeneacetic acid	ChEBI
Fenoprofene	ChEBI
Fenoprofeno	ChEBI
Fenoprofenum	ChEBI
(+-)-2-(3-Phenoxyphenyl)propionate	Generator
(+-)-m-Phenoxyhydratropate	Generator
2-(3-Phenoxyphenyl)propionate	Generator
2-(m-Phenoxyphenyl)propionate	Generator
a-(m-Phenoxyphenyl)propionate	Generator
a-(m-Phenoxyphenyl)propionic acid	Generator
alpha-(m-Phenoxyphenyl)propionate	Generator
Α-(m-phenoxyphenyl)propionate	Generator
Α-(m-phenoxyphenyl)propionic acid	Generator
a-Methyl-3-phenoxybenzeneacetate	Generator
a-Methyl-3-phenoxybenzeneacetic acid	Generator
alpha-Methyl-3-phenoxybenzeneacetate	Generator
Α-methyl-3-phenoxybenzeneacetate	Generator
Α-methyl-3-phenoxybenzeneacetic acid	Generator
Feneprofen calcium salt dihydrate	HMDB
Fenoprofen calcium	HMDB
Fenoprofen calcium hydrate	HMDB
Calcium, fenoprofen	HMDB
Fenoprofen dihydrate, calcium salt	HMDB
Nalfon	HMDB
Nalgesic	HMDB
Fenoprofen, anhydrous, calcium salt	HMDB

Chemical Formula

C₁₅H₁₄O₃

Average Molecular Weight

242.2699

Monoisotopic Molecular Weight

242.094294314

IUPAC Name

2-(3-phenoxyphenyl)propanoic acid

Traditional Name

fenoprofen

CAS Registry Number

34597-40-5

SMILES

CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C15H14O3/c1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13/h2-11H,1H3,(H,16,17)

InChI Key

RDJGLLICXDHJDY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
2-phenylpropanoic-acid
Diaryl ether
Phenoxy compound
Phenol ether
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:5004 )

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: HMDB0014713)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fenoprofen Action Pathway (PathBank: SMP0000696)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.081 g/L	Not Available
LogP	3.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.081 g/L	ALOGPS
logP	3.87	ALOGPS
logP	3.65	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	-8.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.18 m³·mol⁻¹	ChemAxon
Polarizability	25.3 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]+	157.526	31661259
DarkChem	[M-H]-	155.134	31661259
DeepCCS	[M+H]+	154.718	30932474
DeepCCS	[M-H]-	152.322	30932474
DeepCCS	[M-2H]-	185.314	30932474
DeepCCS	[M+Na]+	160.762	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	150.9	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.5	32859911
AllCCS	[M-H]-	158.2	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	157.5	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.	7.35 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0347 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2345.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	482.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	272.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	657.4 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	728.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	108.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1370.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	536.0 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	1317.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	422.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	451.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	376.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	299.4 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	12.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fenoprofen	CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1	3381.2	Standard polar	33892256
Fenoprofen	CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1	2007.5	Standard non polar	33892256
Fenoprofen	CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1	1995.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fenoprofen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1	2062.6	Semi standard non polar	33892256
Fenoprofen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C1	2305.7	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 - Fenoprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4920000000-d5b009ac51d1a009654f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenoprofen GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9430000000-d3139bfe3d51e590f420	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenoprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenoprofen 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 - Fenoprofen LC-ESI-qTof , Positive-QTOF	splash10-0002-0900000000-856a8aff822346800d28	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenoprofen LC-ESI-qTof , Positive-QTOF	splash10-0002-0900000000-856a8aff822346800d28	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenoprofen LC-ESI-qTof , Positive-QTOF	splash10-0002-0900000000-856a8aff822346800d28	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenoprofen , positive-QTOF	splash10-0002-0900000000-0b8ab61fb369335a1792	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenoprofen , positive-QTOF	splash10-0udi-0900000000-0a6fe356f953cf25a938	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 10V, Positive-QTOF	splash10-0006-0390000000-a7dcddcdf276077845cc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 20V, Positive-QTOF	splash10-0002-1950000000-e911262fea4253a2bc1f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 40V, Positive-QTOF	splash10-0udi-5900000000-5a1de84e2ebbf6ebb083	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 10V, Negative-QTOF	splash10-0006-0390000000-10cd32d4365175fef19f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 20V, Negative-QTOF	splash10-0005-2950000000-899958861c820483a049	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 40V, Negative-QTOF	splash10-0006-9200000000-5dd892f971b30ad34901	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 10V, Negative-QTOF	splash10-0006-0190000000-daf8b691421920a0f11d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 20V, Negative-QTOF	splash10-014i-1900000000-65a830ad4dcd2a71626b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 40V, Negative-QTOF	splash10-0006-9300000000-47cc120d0ebd44f6312a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 10V, Positive-QTOF	splash10-0002-0930000000-b9e59b0c88ade89dffba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 20V, Positive-QTOF	splash10-0002-1910000000-73bfe1b341a814b37f5e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenoprofen 40V, Positive-QTOF	splash10-0gdi-4900000000-40afa111e56b90bca828	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fenoprofen 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 DB00573	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00573	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00573

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3225

KEGG Compound ID

C06997

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

_Fenoprofen

METLIN ID

Not Available

PubChem Compound

3342

PDB ID

Not Available

ChEBI ID

5004

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Poggi JC, Barissa GR, Donadi EA, Foss MC, Cunha FQ, Lanchote VL, dos Reis ML: Pharmacodynamics, chiral pharmacokinetics, and pharmacokinetic-pharmacodynamic modeling of fenoprofen in patients with diabetes mellitus. J Clin Pharmacol. 2006 Nov;46(11):1328-36. [PubMed:17050798 ]

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

Poggi JC, Barissa GR, Donadi EA, Foss MC, Cunha FQ, Lanchote VL, dos Reis ML: Pharmacodynamics, chiral pharmacokinetics, and pharmacokinetic-pharmacodynamic modeling of fenoprofen in patients with diabetes mellitus. J Clin Pharmacol. 2006 Nov;46(11):1328-36. [PubMed:17050798 ]

Showing metabocard for Fenoprofen (HMDB0014713)

MOL for HMDB0014713 (Fenoprofen)

3D MOL for HMDB0014713 (Fenoprofen)

3D SDF for HMDB0014713 (Fenoprofen)

3D-SDF for HMDB0014713 (Fenoprofen)

PDB for HMDB0014713 (Fenoprofen)

3D PDB for HMDB0014713 (Fenoprofen)

SMILES for HMDB0014713 (Fenoprofen)

INCHI for HMDB0014713 (Fenoprofen)

Structure for HMDB0014713 (Fenoprofen)

3D Structure for HMDB0014713 (Fenoprofen)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References