Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 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 02:51:44 UTC

HMDB ID

HMDB0014774

Secondary Accession Numbers

HMDB14774

Metabolite Identification

Common Name

Clofibrate

Description

Clofibrate is only found in individuals that have used or taken this drug. It is a fibric acid derivative used in the treatment of hyperlipoproteinemia type III and severe hypertriglyceridemia (from Martindale, The Extra Pharmacopoeia, 30th ed, p986). Clofibrate increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. Chylomicrons are degraded, VLDLs are converted to LDLs, and LDLs are converted to HDL. This is accompanied by a slight increase in secretion of lipids into the bile and ultimately the intestine. Clofibrate also inhibits the synthesis and increases the clearance of apolipoprotein B, a carrier molecule for VLDL. Also, as a fibrate, clofibrate is an agonist of the PPAR-α receptor[4] in muscle, liver, and other tissues. This agonism ultimately leads to modification in gene expression resulting in increased beta-oxidation, decreased triglyceride secretion, increased HDL, increased lipoprotein lipase activity.

Structure

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

HMDB0014774
     RDKit          3D
Clofibrate
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.7512    2.3536    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6165    1.1515   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425    0.3183   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066   -0.8260   -0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0699   -1.0915   -1.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1859   -1.7671   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -3.1180   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5762   -2.0658   -1.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -1.3488    0.5751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393   -0.2138    0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -0.0047    1.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    1.1282    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    2.0769    1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261    3.5246    1.3040 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751    1.9000   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224    0.7550   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3195    2.1924    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2835    3.1389   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    2.7978    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    0.5514   -0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997    1.4743   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638   -3.7224    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -2.9748    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431   -3.5855   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.9324   -2.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180   -1.2618   -2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -2.3701   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0381   -0.7172    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3707    1.3013    3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    2.6602   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    0.6753   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
M  END

636
  Mrv0541 02231214502D          

 16 16  0  0  0  0            999 V2000
    2.3645   -3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    1.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916   -0.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2  5  1  0  0  0  0
  2  9  1  0  0  0  0
  3  8  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 16  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014774

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H15ClO3/c1-4-15-11(14)12(2,3)16-10-7-5-9(13)6-8-10/h5-8H,4H2,1-3H3

> <INCHI_KEY>
KNHUKKLJHYUCFP-UHFFFAOYSA-N

> <FORMULA>
C12H15ClO3

> <MOLECULAR_WEIGHT>
242.699

> <EXACT_MASS>
242.070972053

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.695844338296073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 2-(4-chlorophenoxy)-2-methylpropanoate

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
3.401834674

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.917404908685935

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
62.13550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
artes

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014774
     RDKit          3D
Clofibrate
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.7512    2.3536    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6165    1.1515   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425    0.3183   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066   -0.8260   -0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0699   -1.0915   -1.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1859   -1.7671   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -3.1180   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5762   -2.0658   -1.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -1.3488    0.5751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393   -0.2138    0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -0.0047    1.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    1.1282    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    2.0769    1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261    3.5246    1.3040 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751    1.9000   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224    0.7550   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3195    2.1924    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2835    3.1389   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    2.7978    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    0.5514   -0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997    1.4743   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638   -3.7224    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -2.9748    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431   -3.5855   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.9324   -2.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180   -1.2618   -2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -2.3701   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0381   -0.7172    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3707    1.3013    3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    2.6602   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    0.6753   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 636                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.414  -5.775   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.414   0.385   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081   3.465   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.415   1.155   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.748   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   2.489   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.518  -0.179   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748  -3.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   5.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    5    9                                                       
CONECT    3    8   10                                                       
CONECT    4    8                                                            
CONECT    5    2    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    4    5                                                  
CONECT    9    2   11   12                                                  
CONECT   10    3   15                                                       
CONECT   11    9   13                                                       
CONECT   12    9   14                                                       
CONECT   13   11   16                                                       
CONECT   14   12   16                                                       
CONECT   15   10                                                            
CONECT   16    1   13   14                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0014774
HETATM    1  C1  UNL     1       2.751   2.354   0.452  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.616   1.151  -0.420  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.543   0.318  -0.070  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.307  -0.826  -0.795  1.00  0.00           C  
HETATM    5  O2  UNL     1       2.070  -1.091  -1.759  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.186  -1.767  -0.487  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.792  -3.118  -0.049  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.576  -2.066  -1.758  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.601  -1.349   0.575  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.339  -0.214   0.720  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.050  -0.005   1.898  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.807   1.128   2.081  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.868   2.077   1.087  1.00  0.00           C  
HETATM   14 CL1  UNL     1      -3.826   3.525   1.304  1.00  0.00          CL  
HETATM   15  C11 UNL     1      -2.175   1.900  -0.092  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.422   0.755  -0.253  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.320   2.192   1.374  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.284   3.139  -0.128  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.775   2.798   0.738  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.545   0.551  -0.364  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.500   1.474  -1.458  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.064  -3.722   0.287  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.566  -2.975   0.712  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.243  -3.585  -0.949  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.074  -2.932  -2.235  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.518  -1.262  -2.520  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.624  -2.370  -1.551  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.038  -0.717   2.711  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.371   1.301   3.006  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.241   2.660  -0.853  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.903   0.675  -1.205  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    8    9
CONECT    7   22   23   24
CONECT    8   25   26   27
CONECT    9   10
CONECT   10   11   11   16
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   15
CONECT   15   16   16   30
CONECT   16   31
END

HMDB0014774
     RDKit          3D
Clofibrate
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.7512    2.3536    0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6165    1.1515   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425    0.3183   -0.0697 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3066   -0.8260   -0.7948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0699   -1.0915   -1.7594 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1859   -1.7671   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -3.1180   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5762   -2.0658   -1.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6007   -1.3488    0.5751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393   -0.2138    0.7203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -0.0047    1.8981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    1.1282    2.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8675    2.0769    1.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261    3.5246    1.3040 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751    1.9000   -0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4224    0.7550   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3195    2.1924    1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2835    3.1389   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7754    2.7978    0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451    0.5514   -0.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4997    1.4743   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638   -3.7224    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662   -2.9748    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2431   -3.5855   -0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0741   -2.9324   -2.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180   -1.2618   -2.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -2.3701   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0381   -0.7172    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3707    1.3013    3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    2.6602   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    0.6753   -1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Chlorophenoxy)-2-methylpropanoic acid ethyl ester	ChEBI
2-(p-Chlorophenoxy)-2-methylpropionic acid ethyl ester	ChEBI
alpha-(p-Chlorophenoxy)isobutyric acid, ethyl ester	ChEBI
alpha-p-Chlorophenoxyisobutyryl ethyl ester	ChEBI
Atromid-S	ChEBI
Clofibrato	ChEBI
Clofibratum	ChEBI
ELPI	ChEBI
EPIB	ChEBI
Ethyl 2-(p-chlorophenoxy)isobutyrate	ChEBI
Ethyl chlorophenoxyisobutyrate	ChEBI
Ethyl clofibrate	ChEBI
Lipofacton	ChEBI
Liprin	ChEBI
2-(4-Chlorophenoxy)-2-methylpropanoate ethyl ester	Generator
2-(p-Chlorophenoxy)-2-methylpropionate ethyl ester	Generator
a-(p-Chlorophenoxy)isobutyrate, ethyl ester	Generator
a-(p-Chlorophenoxy)isobutyric acid, ethyl ester	Generator
alpha-(p-Chlorophenoxy)isobutyrate, ethyl ester	Generator
Α-(p-chlorophenoxy)isobutyrate, ethyl ester	Generator
Α-(p-chlorophenoxy)isobutyric acid, ethyl ester	Generator
a-p-Chlorophenoxyisobutyryl ethyl ester	Generator
Α-p-chlorophenoxyisobutyryl ethyl ester	Generator
Ethyl 2-(p-chlorophenoxy)isobutyric acid	Generator
Ethyl chlorophenoxyisobutyric acid	Generator
Ethyl clofibric acid	Generator
Clofibric acid	Generator
Chlorfenisate	HMDB
Chlorphenisate	HMDB
Clofibate	HMDB
CPIB	HMDB
Ethyl p-chlorophenoxyisobutyrate	HMDB
Ethyl para-chlorophenoxyisobutyrate	HMDB
Miscleron	HMDB
Clofibric acid, ethyl ester	HMDB
Atromid	HMDB
Atromid S	HMDB
Miskleron	HMDB
Chlorophenoxyisobutyrate, ethyl	HMDB
Athromidin	HMDB

Chemical Formula

C₁₂H₁₅ClO₃

Average Molecular Weight

242.699

Monoisotopic Molecular Weight

242.070972053

IUPAC Name

ethyl 2-(4-chlorophenoxy)-2-methylpropanoate

Traditional Name

artes

CAS Registry Number

637-07-0

SMILES

CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C12H15ClO3/c1-4-15-11(14)12(2,3)16-10-7-5-9(13)6-8-10/h5-8H,4H2,1-3H3

InChI Key

KNHUKKLJHYUCFP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic acid derivatives

Alternative Parents

Substituents

Phenoxyacetate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organochloride
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organohalogen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ethyl ester (CHEBI:3750 )
aromatic ether (CHEBI:3750 )
monochlorobenzenes (CHEBI:3750 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014774)
Membrane (HMDB: HMDB0014774)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.029 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	3.99	ALOGPS
logP	3.4	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.14 m³·mol⁻¹	ChemAxon
Polarizability	24.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	155.656	30932474
DeepCCS	[M-H]-	153.298	30932474
DeepCCS	[M-2H]-	186.184	30932474
DeepCCS	[M+Na]+	161.749	30932474
AllCCS	[M+H]+	151.9	32859911
AllCCS	[M+H-H2O]+	148.3	32859911
AllCCS	[M+NH4]+	155.3	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	154.6	32859911
AllCCS	[M+Na-2H]-	155.0	32859911
AllCCS	[M+HCOO]-	155.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clofibrate	CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1	2253.5	Standard polar	33892256
Clofibrate	CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1	1603.6	Standard non polar	33892256
Clofibrate	CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1	1571.6	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 - Clofibrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-4900000000-b0f27a4473b7e59d68c3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clofibrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-3900000000-fc2f01df51d424557e9f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofibrate 10V, Positive-QTOF	splash10-014v-0930000000-829386905d164431d8d2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofibrate 20V, Positive-QTOF	splash10-014r-0900000000-7d85ceb3a8f1381c7da6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofibrate 40V, Positive-QTOF	splash10-001l-0900000000-4a173dddc088d2ecd596	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofibrate 30V, Positive-QTOF	splash10-015c-0900000000-dcd68fabfcd01b516107	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofibrate 20V, Positive-QTOF	splash10-014r-0900000000-409b5800e94ffbb11863	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clofibrate 40V, Positive-QTOF	splash10-001l-0900000000-63251a4c6680c9389c2f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 10V, Positive-QTOF	splash10-0006-0390000000-a206c9f16b476083dcdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 20V, Positive-QTOF	splash10-004i-1920000000-cdf7fd63fdcb1f2840cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 40V, Positive-QTOF	splash10-004i-6900000000-bf1eef6ec7349495a9b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 10V, Negative-QTOF	splash10-0006-0290000000-f8e44478c85e8deb28e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 20V, Negative-QTOF	splash10-004l-1960000000-5686cbdf03cff625cebc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 40V, Negative-QTOF	splash10-004i-2900000000-de1ce5552c1bea344c1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 10V, Positive-QTOF	splash10-0006-6980000000-60ef91c08059dec83cfe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 20V, Positive-QTOF	splash10-00p0-7910000000-106c9afa2a025a09891e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 40V, Positive-QTOF	splash10-0a4i-9200000000-710d7a203fef2cd8e30b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 10V, Negative-QTOF	splash10-004i-0920000000-255926cbf0927bf8a9fa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 20V, Negative-QTOF	splash10-004i-4910000000-64c9da59c5fb22afb366	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofibrate 40V, Negative-QTOF	splash10-0059-7900000000-cd5c6706685e8cd7dbe1	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB00636	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00636	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00636

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2694

KEGG Compound ID

C06916

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clofibrate

METLIN ID

Not Available

PubChem Compound

2796

PDB ID

Not Available

ChEBI ID

3750

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. Cytochrome P450 4A11

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:: CYP4A11
Uniprot ID:: Q02928
Molecular weight:: 59347.31

References

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

Enzyme Details

2. Glutathione S-transferase A2

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTA2
Uniprot ID:: P09210
Molecular weight:: 25663.675

References

Foliot A, Touchard D, Mallet L: Inhibition of liver glutathione S-transferase activity in rats by hypolipidemic drugs related or unrelated to clofibrate. Biochem Pharmacol. 1986 May 15;35(10):1685-90. [PubMed:3707598 ]
Foliot A, Touchard D, Celier C: Impairment of hepatic glutathione S-transferase activity as a cause of reduced biliary sulfobromophthalein excretion in clofibrate-treated rats. Biochem Pharmacol. 1984 Sep 15;33(18):2829-34. [PubMed:6477642 ]

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

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

Enzyme Details

4. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

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

Enzyme Details

5. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

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

Enzyme Details

6. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

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

Enzyme Details

7. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

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

Enzyme Details

8. Peroxisome proliferator-activated receptor alpha

General function:: Involved in DNA binding
Specific function:: Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl- 2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene
Gene Name:: PPARA
Uniprot ID:: Q07869
Molecular weight:: 52224.6

References

Barclay TB, Peters JM, Sewer MB, Ferrari L, Gonzalez FJ, Morgan ET: Modulation of cytochrome P-450 gene expression in endotoxemic mice is tissue specific and peroxisome proliferator-activated receptor-alpha dependent. J Pharmacol Exp Ther. 1999 Sep;290(3):1250-7. [PubMed:10454501 ]
Murata M, Kaji H, Takahashi Y, Iida K, Mizuno I, Okimura Y, Abe H, Chihara K: Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro. Biochem Biophys Res Commun. 2000 Apr 13;270(2):343-8. [PubMed:10753628 ]
Hunt MC, Lindquist PJ, Peters JM, Gonzalez FJ, Diczfalusy U, Alexson SE: Involvement of the peroxisome proliferator-activated receptor alpha in regulating long-chain acyl-CoA thioesterases. J Lipid Res. 2000 May;41(5):814-23. [PubMed:10787442 ]
Casas F, Domenjoud L, Rochard P, Hatier R, Rodier A, Daury L, Bianchi A, Kremarik-Bouillaud P, Becuwe P, Keller J, Schohn H, Wrutniak-Cabello C, Cabello G, Dauca M: A 45 kDa protein related to PPARgamma2, induced by peroxisome proliferators, is located in the mitochondrial matrix. FEBS Lett. 2000 Jul 28;478(1-2):4-8. [PubMed:10922459 ]
Komuves LG, Hanley K, Lefebvre AM, Man MQ, Ng DC, Bikle DD, Williams ML, Elias PM, Auwerx J, Feingold KR: Stimulation of PPARalpha promotes epidermal keratinocyte differentiation in vivo. J Invest Dermatol. 2000 Sep;115(3):353-60. [PubMed:10951268 ]
Gelosa P, Banfi C, Gianella A, Brioschi M, Pignieri A, Nobili E, Castiglioni L, Cimino M, Tremoli E, Sironi L: Peroxisome proliferator-activated receptor {alpha} agonism prevents renal damage and the oxidative stress and inflammatory processes affecting the brains of stroke-prone rats. J Pharmacol Exp Ther. 2010 Nov;335(2):324-31. doi: 10.1124/jpet.110.171090. Epub 2010 Jul 29. [PubMed:20671072 ]
Palkar PS, Anderson CR, Ferry CH, Gonzalez FJ, Peters JM: Effect of prenatal peroxisome proliferator-activated receptor alpha (PPARalpha) agonism on postnatal development. Toxicology. 2010 Sep 30;276(1):79-84. doi: 10.1016/j.tox.2010.07.008. Epub 2010 Jul 15. [PubMed:20637823 ]

Showing metabocard for Clofibrate (HMDB0014774)

MOL for HMDB0014774 (Clofibrate)

3D MOL for HMDB0014774 (Clofibrate)

3D SDF for HMDB0014774 (Clofibrate)

3D-SDF for HMDB0014774 (Clofibrate)

PDB for HMDB0014774 (Clofibrate)

3D PDB for HMDB0014774 (Clofibrate)

SMILES for HMDB0014774 (Clofibrate)

INCHI for HMDB0014774 (Clofibrate)

Structure for HMDB0014774 (Clofibrate)

3D Structure for HMDB0014774 (Clofibrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References