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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:01:19 UTC

Update Date

2021-09-26 23:04:37 UTC

HMDB ID

HMDB0252193

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fenbufen

Description

Fenbufen belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Fenbufen is available as a capsule or tablet sold with the brand names Cepal, Cinopal, Cybufen, Lederfen, and Reugast. Fenbufen is an extremely weak basic (essentially neutral) compound (based on its pKa). It can also be used to relieve backaches, sprains, and fractures. Fenbufen is a non-steroidal anti-inflammatory drug used primarily to treat inflammation in osteoarthritis, ankylosing spondylitis, and tendinitis. Fenbufen acts by preventing cyclooxygenase from producing prostaglandins which can cause inflammation. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fenbufen is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fenbufen is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252193
     RDKit          3D
Fenbufen
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.5860   -1.0050    0.4996 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3108   -0.2276   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -0.0823    0.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7523    0.5413   -1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840    0.2494   -1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    0.6475   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114    1.1834    0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344    0.4423   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.1373   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522   -0.3428   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6228    0.0308    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -0.1710    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9270   -0.1201   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2792   -0.3057   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8142   -0.5527    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -0.6111    1.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239   -0.4221    1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680    0.6182    1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874    0.8211    1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9384   -0.3143    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3031    0.3251   -2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9558    1.6116   -1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -0.8407   -1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    0.7706   -2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -0.4398   -1.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -0.7999   -1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040    0.0754   -1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9041   -0.2506   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874   -0.6935    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4312   -0.8101    2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9730   -0.4692    2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    0.9255    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967    1.2798    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  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
 11 18  1  0
 18 19  2  0
 19  8  1  0
 17 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  9 25  1  0
 10 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
 19 33  1  0
M  END


  Mrv0541 06101408532D          

 19 20  0  0  0  0            999 V2000
    8.5736    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7157   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  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
M  END
> <DATABASE_ID>
HMDB0252193

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19)

> <INCHI_KEY>
ZPAKPRAICRBAOD-UHFFFAOYSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.2806

> <EXACT_MASS>
254.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.470579483696106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-oxo-4-(4-phenylphenyl)butanoic acid

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.002981443666666

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.896667850094893

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.219627481906022

> <JCHEM_PKA_STRONGEST_BASIC>
-7.454900028981266

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
72.49029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fenbufen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252193
     RDKit          3D
Fenbufen
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.5860   -1.0050    0.4996 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3108   -0.2276   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -0.0823    0.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7523    0.5413   -1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840    0.2494   -1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    0.6475   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114    1.1834    0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344    0.4423   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.1373   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522   -0.3428   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6228    0.0308    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -0.1710    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9270   -0.1201   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2792   -0.3057   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8142   -0.5527    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -0.6111    1.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239   -0.4221    1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680    0.6182    1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874    0.8211    1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9384   -0.3143    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3031    0.3251   -2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9558    1.6116   -1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -0.8407   -1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    0.7706   -2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -0.4398   -1.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -0.7999   -1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040    0.0754   -1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9041   -0.2506   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874   -0.6935    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4312   -0.8101    2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9730   -0.4692    2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    0.9255    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967    1.2798    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  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
 11 18  1  0
 18 19  2  0
 19  8  1  0
 17 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  9 25  1  0
 10 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
 19 33  1  0
M  END

HEADER    PROTEIN                                 10-JUN-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUN-14         0                                  
HETATM    1  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   12                                                       
CONECT    6    8   13                                                       
CONECT    7    9   13                                                       
CONECT    8    6   14                                                       
CONECT    9    7   14                                                       
CONECT   10   11   15                                                       
CONECT   11   10   16                                                       
CONECT   12    4    5   13                                                  
CONECT   13    6    7   12                                                  
CONECT   14    8    9   15                                                  
CONECT   15   10   14   17                                                  
CONECT   16   11   18   19                                                  
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0252193
HETATM    1  O1  UNL     1       4.586  -1.005   0.500  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.311  -0.228  -0.148  1.00  0.00           C  
HETATM    3  O2  UNL     1       6.641  -0.082   0.182  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.752   0.541  -1.270  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.284   0.249  -1.401  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.580   0.648  -0.185  1.00  0.00           C  
HETATM    7  O3  UNL     1       3.211   1.183   0.756  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.134   0.442  -0.016  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.426  -0.137  -1.025  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.952  -0.343  -0.889  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.623   0.031   0.256  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.059  -0.171   0.425  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.927  -0.120  -0.650  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.279  -0.306  -0.518  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.814  -0.553   0.717  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.982  -0.611   1.812  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.624  -0.422   1.662  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.868   0.618   1.262  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.487   0.821   1.130  1.00  0.00           C  
HETATM   20  H1  UNL     1       6.938  -0.314   1.132  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.303   0.325  -2.227  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.956   1.612  -1.063  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.103  -0.841  -1.621  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.919   0.771  -2.316  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.933  -0.440  -1.935  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.487  -0.800  -1.694  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.504   0.075  -1.629  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.904  -0.251  -1.417  1.00  0.00           H  
HETATM   29  H10 UNL     1      -6.887  -0.694   0.776  1.00  0.00           H  
HETATM   30  H11 UNL     1      -5.431  -0.810   2.791  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.973  -0.469   2.528  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.348   0.925   2.172  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.097   1.280   1.907  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    7    8
CONECT    8    9    9   19
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   18
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   19   19   32
CONECT   19   33
END

HMDB0252193
     RDKit          3D
Fenbufen
 33 34  0  0  0  0  0  0  0  0999 V2000
    4.5860   -1.0050    0.4996 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3108   -0.2276   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6413   -0.0823    0.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7523    0.5413   -1.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2840    0.2494   -1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    0.6475   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114    1.1834    0.7556 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1344    0.4423   -0.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.1373   -1.0250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522   -0.3428   -0.8886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6228    0.0308    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -0.1710    0.4245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9270   -0.1201   -0.6504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2792   -0.3057   -0.5185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8142   -0.5527    0.7165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -0.6111    1.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239   -0.4221    1.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680    0.6182    1.2620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874    0.8211    1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9384   -0.3143    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3031    0.3251   -2.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9558    1.6116   -1.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -0.8407   -1.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9187    0.7706   -2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -0.4398   -1.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -0.7999   -1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5040    0.0754   -1.6292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9041   -0.2506   -1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8874   -0.6935    0.7761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4312   -0.8101    2.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9730   -0.4692    2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479    0.9255    2.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0967    1.2798    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  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
 11 18  1  0
 18 19  2  0
 19  8  1  0
 17 12  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  9 25  1  0
 10 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
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(4-Biphenylylcarbonyl)propionic acid	ChEBI
3-(4-Phenylbenzoyl)propionic acid	ChEBI
4-(4-Biphenylyl)-4-oxobutyric acid	ChEBI
4-Biphenyl-4-yl-4-oxobutanoic acid	ChEBI
gamma-oxo(1,1'-Biphenyl)-4-butanoic acid	ChEBI
3-(4-Biphenylylcarbonyl)propionate	Generator
3-(4-Phenylbenzoyl)propionate	Generator
4-(4-Biphenylyl)-4-oxobutyrate	Generator
4-Biphenyl-4-yl-4-oxobutanoate	Generator
g-oxo(1,1'-Biphenyl)-4-butanoate	Generator
g-oxo(1,1'-Biphenyl)-4-butanoic acid	Generator
gamma-oxo(1,1'-Biphenyl)-4-butanoate	Generator
Γ-oxo(1,1'-biphenyl)-4-butanoate	Generator
Γ-oxo(1,1'-biphenyl)-4-butanoic acid	Generator
Lederfen	MeSH
Cinopal	MeSH

Chemical Formula

C₁₆H₁₄O₃

Average Molecular Weight

254.2806

Monoisotopic Molecular Weight

254.094294314

IUPAC Name

4-oxo-4-(4-phenylphenyl)butanoic acid

Traditional Name

fenbufen

CAS Registry Number

Not Available

SMILES

OC(=O)CCC(=O)C1=CC=C(C=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19)

InChI Key

ZPAKPRAICRBAOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Biphenyl
Butyrophenone
Aryl alkyl ketone
Gamma-keto acid
Benzoyl
Benzenoid
Keto acid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

biphenyls (CHEBI:31599 )
4-oxo monocarboxylic acid (CHEBI:31599 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	3.07	ALOGPS
logP	3	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.22	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	5	ChemAxon
Refractivity	72.49 m³·mol⁻¹	ChemAxon
Polarizability	27.47 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
DeepCCS	[M+H]+	161.782	30932474
DeepCCS	[M-H]-	159.424	30932474
DeepCCS	[M-2H]-	192.311	30932474
DeepCCS	[M+Na]+	167.875	30932474
AllCCS	[M+H]+	159.2	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.9	32859911
AllCCS	[M-H]-	161.5	32859911
AllCCS	[M+Na-2H]-	161.2	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fenbufen	OC(=O)CCC(=O)C1=CC=C(C=C1)C1=CC=CC=C1	3802.5	Standard polar	33892256
Fenbufen	OC(=O)CCC(=O)C1=CC=C(C=C1)C1=CC=CC=C1	2199.1	Standard non polar	33892256
Fenbufen	OC(=O)CCC(=O)C1=CC=C(C=C1)C1=CC=CC=C1	2415.1	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 - Fenbufen GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1910000000-193b196fc2e050e8f27c	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenbufen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenbufen GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fenbufen GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbufen LC-ESI-qTof , Positive-QTOF	splash10-05nu-5910000000-f91ec96f1a16f6d0bbba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fenbufen , positive-QTOF	splash10-0f89-2900000000-b30afcea40626e90c194	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 10V, Positive-QTOF	splash10-0a4r-0190000000-0d0f28a5fa7c852b06f7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 20V, Positive-QTOF	splash10-053r-1970000000-9c0a213301016dc1a1e6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 40V, Positive-QTOF	splash10-053r-4910000000-a198d704b4f4bd58bcf0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 10V, Negative-QTOF	splash10-0udi-0090000000-3f4cef288509b8af0743	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 20V, Negative-QTOF	splash10-0udi-1190000000-94922d0f37e5e1b06475	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 40V, Negative-QTOF	splash10-0zi9-5950000000-048f552f7222a6bee083	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 10V, Positive-QTOF	splash10-0a4r-0090000000-0a7b6fc611cc5ec17973	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 20V, Positive-QTOF	splash10-0a4i-0090000000-de7db555f004c229c5d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 40V, Positive-QTOF	splash10-053r-0910000000-c2f9c0dd91a9b819f104	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 10V, Negative-QTOF	splash10-052r-0090000000-a5c8a98d3b5f9a2cedcd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 20V, Negative-QTOF	splash10-0a4i-0290000000-28aa3a6c16ae61d0efdf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fenbufen 40V, Negative-QTOF	splash10-0zfr-2910000000-d401b9eafab13cda753e	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08981

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fenbufen

METLIN ID

Not Available

PubChem Compound

3335

PDB ID

Not Available

ChEBI ID

31599

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Fenbufen (HMDB0252193)

MOL for HMDB0252193 (Fenbufen)

3D MOL for HMDB0252193 (Fenbufen)

3D SDF for HMDB0252193 (Fenbufen)

3D-SDF for HMDB0252193 (Fenbufen)

PDB for HMDB0252193 (Fenbufen)

3D PDB for HMDB0252193 (Fenbufen)

SMILES for HMDB0252193 (Fenbufen)

INCHI for HMDB0252193 (Fenbufen)

Structure for HMDB0252193 (Fenbufen)

3D Structure for HMDB0252193 (Fenbufen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra