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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:48:01 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041920

Secondary Accession Numbers

HMDB41920

Metabolite Identification

Common Name

Loxoprofen

Description

As most NSAIDs, loxoprofen is a non-selective cyclooxygenase inhibitor, and works by reducing the synthesis of prostaglandins from arachidonic acid. Loxoprofen (INN) is a non-steroidal anti-inflammatory drug in the propionic acid derivatives group, which also includes ibuprofen and naproxen among others. It is marketed in Brazil, Mexico and Japan by Sankyo as its sodium salt, loxoprofen sodium, under the trade name Loxonin, Argentina as Oxeno and in India as Loxomac. It is available in these countries for oral administration, and a transdermal preparation was approved for sale in Japan on January 2006. Loxoprofen is a prodrug. It is quickly converted to its active trans-alcohol metabolite following oral administration, and reaches its peak plasma concentration within 30 to 50 minutes.

Structure

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

HMDB0041920
     RDKit          3D
Loxoprofen
 36 37  0  0  0  0  0  0  0  0999 V2000
    4.0623    1.4170    1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065   -0.0730    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7936   -0.6320   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6246   -1.5369    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8830   -0.1963   -1.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4053   -0.2780    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -1.0028    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074   -1.1820    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2492   -0.6589   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.8521   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5844    0.2368   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.0459   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8495    0.6023   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880    0.0703    1.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622    0.3214    0.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8760    0.5595    1.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    0.0699   -1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9824    0.2574   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9423    1.7118    0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176    1.6110    2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1635    1.9671    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324   -0.5859    1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846    0.7645   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -1.4492    2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810   -1.7523    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288   -0.9673   -2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062   -1.7995   -0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2754    1.2335   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -1.1380   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468    0.3576   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8986    0.3170   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636    1.6947   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4029   -1.0023    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    0.6344    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658    0.4856   -2.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    0.8407   -1.4642 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18  6  1  0
 15 11  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
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
M  END

  Mrv0541 09131211482D          

 18 19  0  0  0  0            999 V2000
   -4.2868    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.2911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665    3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    7.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.1786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  1  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  1  0  0  0  0
 14  4  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041920

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)

> <INCHI_KEY>
YMBXTVYHTMGZDW-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.077965064695736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.345719083333334

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.191381188684435

> <JCHEM_PKA_STRONGEST_BASIC>
-7.417205982947168

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
68.79899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
loxoprofen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041920
     RDKit          3D
Loxoprofen
 36 37  0  0  0  0  0  0  0  0999 V2000
    4.0623    1.4170    1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065   -0.0730    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7936   -0.6320   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6246   -1.5369    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8830   -0.1963   -1.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4053   -0.2780    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -1.0028    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074   -1.1820    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2492   -0.6589   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.8521   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5844    0.2368   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.0459   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8495    0.6023   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880    0.0703    1.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622    0.3214    0.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8760    0.5595    1.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    0.0699   -1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9824    0.2574   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9423    1.7118    0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176    1.6110    2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1635    1.9671    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324   -0.5859    1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846    0.7645   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -1.4492    2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810   -1.7523    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288   -0.9673   -2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062   -1.7995   -0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2754    1.2335   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -1.1380   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468    0.3576   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8986    0.3170   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636    1.6947   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4029   -1.0023    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    0.6344    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658    0.4856   -2.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    0.8407   -1.4642 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18  6  1  0
 15 11  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
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -8.002  10.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.564   4.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.088   5.565   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.104   4.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  10.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   8.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  11.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   8.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   8.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  11.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   8.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  10.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   6.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.580   5.565   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  12.630   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.044   6.041   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -8.002  13.400   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.335  13.400   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2   13                                                       
CONECT    4    2   14                                                       
CONECT    5    7   11                                                       
CONECT    6    8   11                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9   11   13                                                       
CONECT   10    1   12   15                                                  
CONECT   11    5    6    9                                                  
CONECT   12    7    8   10                                                  
CONECT   13    3    9   14                                                  
CONECT   14    4   13   16                                                  
CONECT   15   10   17   18                                                  
CONECT   16   14                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0041920
HETATM    1  C1  UNL     1       4.062   1.417   1.096  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.807  -0.073   0.844  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.794  -0.632  -0.086  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.625  -1.537   0.242  1.00  0.00           O  
HETATM    5  O2  UNL     1       4.883  -0.196  -1.412  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.405  -0.278   0.382  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.509  -1.003   1.139  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.207  -1.182   0.690  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.249  -0.659  -0.505  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.633  -0.852  -0.970  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.584   0.237  -0.538  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.978  -0.046  -1.058  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.850   0.602  -0.008  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.188   0.070   1.273  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.762   0.321   0.930  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.876   0.560   1.720  1.00  0.00           O  
HETATM   17  C14 UNL     1       0.686   0.070  -1.247  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.982   0.257  -0.816  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.942   1.712   0.489  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.318   1.611   2.156  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.163   1.967   0.806  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.932  -0.586   1.827  1.00  0.00           H  
HETATM   23  H5  UNL     1       5.185   0.764  -1.595  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.786  -1.449   2.093  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.481  -1.752   1.289  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.629  -0.967  -2.070  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.006  -1.799  -0.530  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.275   1.234  -0.966  1.00  0.00           H  
HETATM   29  H11 UNL     1      -4.142  -1.138  -0.979  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.147   0.358  -2.068  1.00  0.00           H  
HETATM   31  H13 UNL     1      -5.899   0.317  -0.067  1.00  0.00           H  
HETATM   32  H14 UNL     1      -4.664   1.695  -0.063  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.403  -1.002   1.304  1.00  0.00           H  
HETATM   34  H16 UNL     1      -4.524   0.634   2.157  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.366   0.486  -2.172  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.637   0.841  -1.464  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    6   22
CONECT    3    4    4    5
CONECT    5   23
CONECT    6    7    7   18
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   17
CONECT   10   11   26   27
CONECT   11   12   15   28
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   16
CONECT   17   18   18   35
CONECT   18   36
END

HMDB0041920
     RDKit          3D
Loxoprofen
 36 37  0  0  0  0  0  0  0  0999 V2000
    4.0623    1.4170    1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065   -0.0730    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7936   -0.6320   -0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6246   -1.5369    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8830   -0.1963   -1.4125 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4053   -0.2780    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087   -1.0028    1.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074   -1.1820    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2492   -0.6589   -0.5054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -0.8521   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5844    0.2368   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9776   -0.0459   -1.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8495    0.6023   -0.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880    0.0703    1.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7622    0.3214    0.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8760    0.5595    1.7197 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    0.0699   -1.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9824    0.2574   -0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9423    1.7118    0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176    1.6110    2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1635    1.9671    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9324   -0.5859    1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846    0.7645   -1.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -1.4492    2.0935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4810   -1.7523    1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288   -0.9673   -2.0701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062   -1.7995   -0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2754    1.2335   -0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418   -1.1380   -0.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1468    0.3576   -2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8986    0.3170   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6636    1.6947   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4029   -1.0023    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    0.6344    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658    0.4856   -2.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    0.8407   -1.4642 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18  6  1  0
 15 11  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
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-((2-Oxocyclopentyl)methyl)hydratropic acid	ChEBI
Loxoprofene	ChEBI
Loxoprofeno	ChEBI
Loxoprofenum	ChEBI
(+-)-((2-Oxocyclopentyl)methyl)hydratropate	Generator
Loxoprofen sodium hydrate	HMDB
Loxoprofen alcohol	HMDB
Sodium 2-(4-(2-oxocyclopentylmethyl)phenyl)propionate dihydrate	HMDB
Loxoprofen sodium, (r,s)-isomer	HMDB
2-(4-((2-Oxocyclopentyl)methyl)phenyl)propionic acid	HMDB
2-OCPPP	HMDB
Loxoprofen sodium dihydrate	HMDB
Sodium loxoprofen	HMDB

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.3016

Monoisotopic Molecular Weight

246.125594442

IUPAC Name

2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid

Traditional Name

loxoprofen

CAS Registry Number

80382-23-6

SMILES

CC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1

InChI Identifier

InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)

InChI Key

YMBXTVYHTMGZDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

2-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Monocyclic benzene moiety
Benzenoid
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:76172 )
cyclopentanones (CHEBI:76172 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041920)

Source

Exogenous

Exogenous (HMDB: HMDB0041920)

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	0.066 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.35	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.19	ChemAxon
pKa (Strongest Basic)	-7.4	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	68.8 m³·mol⁻¹	ChemAxon
Polarizability	27.08 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]+	159.141	31661259
DarkChem	[M-H]-	155.234	31661259
DeepCCS	[M+H]+	158.879	30932474
DeepCCS	[M-H]-	156.521	30932474
DeepCCS	[M-2H]-	189.408	30932474
DeepCCS	[M+Na]+	164.972	30932474
AllCCS	[M+H]+	158.1	32859911
AllCCS	[M+H-H2O]+	154.3	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.7	32859911
AllCCS	[M-H]-	163.0	32859911
AllCCS	[M+Na-2H]-	163.1	32859911
AllCCS	[M+HCOO]-	163.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Loxoprofen	CC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1	3695.1	Standard polar	33892256
Loxoprofen	CC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1	2114.5	Standard non polar	33892256
Loxoprofen	CC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1	2092.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Loxoprofen,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC2CCCC2=O)C=C1	2173.9	Semi standard non polar	33892256
Loxoprofen,1TMS,isomer #2	CC(C(=O)O)C1=CC=C(CC2=C(O[Si](C)(C)C)CCC2)C=C1	2256.6	Semi standard non polar	33892256
Loxoprofen,1TMS,isomer #3	CC(C(=O)O)C1=CC=C(CC2CCC=C2O[Si](C)(C)C)C=C1	2220.9	Semi standard non polar	33892256
Loxoprofen,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC2=C(O[Si](C)(C)C)CCC2)C=C1	2255.0	Semi standard non polar	33892256
Loxoprofen,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC2=C(O[Si](C)(C)C)CCC2)C=C1	2187.0	Standard non polar	33892256
Loxoprofen,2TMS,isomer #2	CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC2CCC=C2O[Si](C)(C)C)C=C1	2208.1	Semi standard non polar	33892256
Loxoprofen,2TMS,isomer #2	CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC2CCC=C2O[Si](C)(C)C)C=C1	2147.3	Standard non polar	33892256
Loxoprofen,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC2CCCC2=O)C=C1	2438.1	Semi standard non polar	33892256
Loxoprofen,1TBDMS,isomer #2	CC(C(=O)O)C1=CC=C(CC2=C(O[Si](C)(C)C(C)(C)C)CCC2)C=C1	2555.1	Semi standard non polar	33892256
Loxoprofen,1TBDMS,isomer #3	CC(C(=O)O)C1=CC=C(CC2CCC=C2O[Si](C)(C)C(C)(C)C)C=C1	2494.5	Semi standard non polar	33892256
Loxoprofen,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC2=C(O[Si](C)(C)C(C)(C)C)CCC2)C=C1	2763.0	Semi standard non polar	33892256
Loxoprofen,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC2=C(O[Si](C)(C)C(C)(C)C)CCC2)C=C1	2617.1	Standard non polar	33892256
Loxoprofen,2TBDMS,isomer #2	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC2CCC=C2O[Si](C)(C)C(C)(C)C)C=C1	2698.0	Semi standard non polar	33892256
Loxoprofen,2TBDMS,isomer #2	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC2CCC=C2O[Si](C)(C)C(C)(C)C)C=C1	2509.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Loxoprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gi0-2950000000-f1f143e2589e1aea4173	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loxoprofen GC-MS (1 TMS) - 70eV, Positive	splash10-0600-9882000000-95383cbac1177e9a0726	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loxoprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Loxoprofen 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 - Loxoprofen 35V, Positive-QTOF	splash10-0zfr-0890000000-74ee0167cd6a76ef67d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Loxoprofen 35V, Negative-QTOF	splash10-001i-0090000000-1b731099acfc2cee4d1a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 10V, Positive-QTOF	splash10-0002-1290000000-9a370ea3c1893f34ac6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 20V, Positive-QTOF	splash10-0umj-3940000000-2a5656d17e3cdb5b29ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 40V, Positive-QTOF	splash10-0kx0-1900000000-f6a4fd9d3ed427851cb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 10V, Negative-QTOF	splash10-0002-0090000000-c0fa095368edf3656575	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 20V, Negative-QTOF	splash10-0udj-2290000000-a000dad805df140f2aeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 40V, Negative-QTOF	splash10-00ai-9200000000-485777b0ba108a03a92f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 10V, Negative-QTOF	splash10-0f6t-0190000000-319eb623e74a18ded3a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 20V, Negative-QTOF	splash10-0udi-0390000000-0d1645d8c8daa3d6be44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 40V, Negative-QTOF	splash10-014i-2900000000-8d006d601c3437f0eb2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 10V, Positive-QTOF	splash10-01u0-0690000000-117230d5ff547c24425e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 20V, Positive-QTOF	splash10-02bb-2940000000-c41c0ae60ad2bd310b62	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Loxoprofen 40V, Positive-QTOF	splash10-0159-2900000000-457bd9b0f844b6308beb	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

DB09212

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3828

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Loxoprofen

METLIN ID

Not Available

PubChem Compound

3965

PDB ID

Not Available

ChEBI ID

76172

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

Showing metabocard for Loxoprofen (HMDB0041920)

MOL for HMDB0041920 (Loxoprofen)

3D MOL for HMDB0041920 (Loxoprofen)

3D SDF for HMDB0041920 (Loxoprofen)

3D-SDF for HMDB0041920 (Loxoprofen)

PDB for HMDB0041920 (Loxoprofen)

3D PDB for HMDB0041920 (Loxoprofen)

SMILES for HMDB0041920 (Loxoprofen)

INCHI for HMDB0041920 (Loxoprofen)

Structure for HMDB0041920 (Loxoprofen)

3D Structure for HMDB0041920 (Loxoprofen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra