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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015371

Secondary Accession Numbers

HMDB15371

Metabolite Identification

Common Name

Gemfibrozil

Description

Gemfibrozil, also known as lopid or bolutol, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Gemfibrozil is an extremely weak basic (essentially neutral) compound (based on its pKa). Gemfibrozil is a potentially toxic compound. This is accompanied by a slight increase in secretion of lipids into the bile and ultimately the intestine. IV): Gemfibrozil, though not as effective as niacin, is better tolerated. Statin drugs: Concomitant administration of fibrates (including gemfibrozil) with statin drugs increases the risk of muscle cramping, myopathy, and rhabdomyolysis. Serious side effects may include angioedema, gallstones, liver problems, and muscle breakdown. It is unclear if it changes the risk of heart disease.

Structure

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

HMDB0015371
     RDKit          3D
Gemfibrozil
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.1181   -1.8713    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -0.6703    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7552    0.5579    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    1.6638    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    1.6021    0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7007    2.7964    0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736    0.3759   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967    0.3104   -0.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.9464   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249   -0.8099   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0402   -0.3510    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5249   -0.2006    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    0.2677    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1813   -1.5152   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8727    0.8133   -0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4697    1.8811   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641    0.6408   -2.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -0.7296   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805   -2.1325    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4836   -2.7333   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9432   -1.7484   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213    0.5896    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513    2.6226    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    2.8672    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873    3.6855    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202    2.8112   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -1.2198   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836   -1.6835    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311   -0.0255   -1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231   -1.7880   -1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6609    0.6521    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.0634    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -0.6255    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9055    0.9686    1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    0.7773    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5172   -1.4697   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549   -1.7143    0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4244   -2.3513   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1561    1.4478   -2.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4887   -1.6816   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
M  END

1241
  Mrv1652305271900132D          

 18 18  0  0  0  0            999 V2000
    3.0791   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3330    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6830    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 11  1  0  0  0  0
  2 10  1  0  0  0  0
  3 10  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 15  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 14 16  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015371

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)

> <INCHI_KEY>
HEMJJKBWTPKOJG-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.9023368730034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
4.389643824

> <ALOGPS_LOGS>
-3.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.416800554942657

> <JCHEM_PKA_STRONGEST_BASIC>
-4.837321215457823

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
71.8191

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gemfibrozil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015371
     RDKit          3D
Gemfibrozil
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.1181   -1.8713    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -0.6703    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7552    0.5579    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    1.6638    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    1.6021    0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7007    2.7964    0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736    0.3759   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967    0.3104   -0.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.9464   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249   -0.8099   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0402   -0.3510    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5249   -0.2006    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    0.2677    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1813   -1.5152   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8727    0.8133   -0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4697    1.8811   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641    0.6408   -2.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -0.7296   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805   -2.1325    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4836   -2.7333   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9432   -1.7484   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213    0.5896    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513    2.6226    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    2.8672    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873    3.6855    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202    2.8112   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -1.2198   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836   -1.6835    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311   -0.0255   -1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231   -1.7880   -1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6609    0.6521    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.0634    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -0.6255    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9055    0.9686    1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    0.7773    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5172   -1.4697   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549   -1.7143    0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4244   -2.3513   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1561    1.4478   -2.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4887   -1.6816   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1241                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       5.748  -1.632   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.748   5.298   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081   5.298   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.415   2.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415   1.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.678   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.875   2.988   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -0.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   4.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -3.172   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.942   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -3.942   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -5.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -5.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -6.253   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -3.172   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.415  -6.253   0.000  0.00  0.00           C+0
CONECT    1    9   11                                                       
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    5    7    8   10                                             
CONECT    5    4    6                                                       
CONECT    6    5    9                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    1    6                                                       
CONECT   10    2    3    4                                                  
CONECT   11    1   12   13                                                  
CONECT   12   11   15   17                                                  
CONECT   13   11   14                                                       
CONECT   14   13   16   18                                                  
CONECT   15   12   16                                                       
CONECT   16   14   15                                                       
CONECT   17   12                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0015371
HETATM    1  C1  UNL     1       5.118  -1.871   0.008  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.247  -0.670   0.124  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.755   0.558   0.497  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.937   1.664   0.601  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.584   1.602   0.340  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.701   2.796   0.452  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.074   0.376  -0.034  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.697   0.310  -0.300  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.169  -0.946  -0.684  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.325  -0.810  -0.925  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.040  -0.351   0.299  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.525  -0.201   0.163  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.059   0.268   1.510  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.181  -1.515  -0.212  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.873   0.813  -0.850  1.00  0.00           C  
HETATM   16  O2  UNL     1      -4.470   1.881  -0.514  1.00  0.00           O  
HETATM   17  O3  UNL     1      -3.564   0.641  -2.194  1.00  0.00           O  
HETATM   18  C15 UNL     1       2.893  -0.730  -0.137  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.580  -2.133   1.002  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.484  -2.733  -0.261  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.943  -1.748  -0.696  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.821   0.590   0.699  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.351   2.623   0.896  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.268   2.867   1.465  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.387   3.686   0.357  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.920   2.811  -0.325  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.666  -1.220  -1.637  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.384  -1.683   0.116  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.431  -0.026  -1.713  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.723  -1.788  -1.252  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.661   0.652   0.654  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.841  -1.063   1.154  1.00  0.00           H  
HETATM   33  H15 UNL     1      -4.425  -0.625   2.084  1.00  0.00           H  
HETATM   34  H16 UNL     1      -4.905   0.969   1.322  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.292   0.777   2.097  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.517  -1.470  -1.253  1.00  0.00           H  
HETATM   37  H19 UNL     1      -5.055  -1.714   0.428  1.00  0.00           H  
HETATM   38  H20 UNL     1      -3.424  -2.351  -0.172  1.00  0.00           H  
HETATM   39  H21 UNL     1      -3.156   1.448  -2.680  1.00  0.00           H  
HETATM   40  H22 UNL     1       2.489  -1.682  -0.428  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6    7
CONECT    6   24   25   26
CONECT    7    8   18   18
CONECT    8    9
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   14   15
CONECT   13   33   34   35
CONECT   14   36   37   38
CONECT   15   16   16   17
CONECT   17   39
CONECT   18   40
END

HMDB0015371
     RDKit          3D
Gemfibrozil
 40 40  0  0  0  0  0  0  0  0999 V2000
    5.1181   -1.8713    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -0.6703    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7552    0.5579    0.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    1.6638    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5836    1.6021    0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7007    2.7964    0.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736    0.3759   -0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967    0.3104   -0.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694   -0.9464   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249   -0.8099   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0402   -0.3510    0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5249   -0.2006    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0591    0.2677    1.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1813   -1.5152   -0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8727    0.8133   -0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4697    1.8811   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641    0.6408   -2.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8931   -0.7296   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805   -2.1325    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4836   -2.7333   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9432   -1.7484   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213    0.5896    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3513    2.6226    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677    2.8672    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873    3.6855    0.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202    2.8112   -0.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -1.2198   -1.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3836   -1.6835    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4311   -0.0255   -1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231   -1.7880   -1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6609    0.6521    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8409   -1.0634    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4249   -0.6255    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9055    0.9686    1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    0.7773    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5172   -1.4697   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549   -1.7143    0.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4244   -2.3513   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1561    1.4478   -2.6801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4887   -1.6816   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
  7 18  2  0
 18  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeure	ChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure	ChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid	ChEBI
Gemfibrozilo	ChEBI
Gemfibrozilum	ChEBI
Lopid	ChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valerate	Generator
1a Brand OF gemfibrozil	HMDB
Alphapharm brand OF gemfibrozil	HMDB
Bayvit, gemfibrozilo	HMDB
Bexal brand OF gemfibrozil	HMDB
Biochemie brand OF gemfibrozil	HMDB
Bolutol	HMDB
Chem mart gemfibrozil	HMDB
Farmasierra brand OF gemfibrozil	HMDB
Faulding brand OF gemfibrozil	HMDB
Gemfibrozil, healthsense	HMDB
GenRX gemfibrozil	HMDB
Genpharm brand OF gemfibrozil	HMDB
Ipsen brand OF gemfibrozil	HMDB
Jezil	HMDB
Lipox gemfi	HMDB
Menarini brand OF gemfibrozil	HMDB
Nu-gemfibrozil	HMDB
Nu-pharm brand OF gemfibrozil	HMDB
PMS-Gemfibrozil	HMDB
SBPA gemfibrozil	HMDB
Sigma brand OF gemfibrozil	HMDB
Warner lambert brand OF gemfibrozil	HMDB
ApoGemfibrozil	HMDB
Ausgem	HMDB
Bayvit brand OF gemfibrozil	HMDB
DBL Gemfibrozil	HMDB
Douglas brand OF gemfibrozil	HMDB
Gemfibrozil, sbpa	HMDB
Gemfibrozilo ur	HMDB
GenGemfibrozil	HMDB
Lipazil	HMDB
Novo-gemfibrozil	HMDB
Nu pharm brand OF gemfibrozil	HMDB
NuGemfibrozil	HMDB
Pharmascience brand OF gemfibrozil	HMDB
Apo-gemfibrozil	HMDB
Cantabria brand OF gemfibrozil	HMDB
Chem mart brand OF gemfibrozil	HMDB
Gemfibrosil	HMDB
Gemfibrozilo bayvit	HMDB
Gemfibrozilo bexal	HMDB
Gemhexal	HMDB
Gen gemfibrozil	HMDB
Gen-gemfibrozil	HMDB
Lipur	HMDB
Lopid R	HMDB
Nu gemfibrozil	HMDB
Parke davis brand OF gemfibrozil	HMDB
Pilder	HMDB
Terry white chemists brand OF gemfibrozil	HMDB
United drug brand OF gemfibrozil	HMDB
Warner-lambert brand OF gemfibrozil	HMDB
Apo gemfibrozil	HMDB
Apotex brand OF gemfibrozil	HMDB
Bull brand OF gemfibrozil	HMDB
Decrelip	HMDB
Ferrer brand OF gemfibrozil	HMDB
Gemfi 1a pharma	HMDB
Gemfibrozil, genrx	HMDB
Healthsense brand OF gemfibrozil	HMDB
Healthsense gemfibrozil	HMDB
Hexal brand OF gemfibrozil	HMDB
Litarek	HMDB
Novo gemfibrozil	HMDB
Novopharm brand OF gemfibrozil	HMDB
PMS Gemfibrozil	HMDB
Pfizer brand OF gemfibrozil	HMDB
Quimifar brand OF gemfibrozil	HMDB
TAD brand OF gemfibrozil	HMDB
Terry white chemists gemfibrozil	HMDB
Trialmin	HMDB

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid

Traditional Name

gemfibrozil

CAS Registry Number

25812-30-0

SMILES

CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1

InChI Identifier

InChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)

InChI Key

HEMJJKBWTPKOJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
P-xylene
Xylene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:5296 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015371)
Membrane (HMDB: HMDB0015371)

Source

Exogenous

Exogenous (HMDB: HMDB0015371)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	61 - 63 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.028 g/L	Not Available
LogP	3.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	3.61	ALOGPS
logP	4.39	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.82 m³·mol⁻¹	ChemAxon
Polarizability	28.9 Å³	ChemAxon
Number of Rings	1	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]+	159.662	31661259
DarkChem	[M-H]-	160.045	31661259
DeepCCS	[M+H]+	166.852	30932474
DeepCCS	[M-H]-	164.494	30932474
DeepCCS	[M-2H]-	197.409	30932474
DeepCCS	[M+Na]+	172.945	30932474
AllCCS	[M+H]+	159.2	32859911
AllCCS	[M+H-H2O]+	155.8	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	164.5	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	165.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gemfibrozil	CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1	2901.6	Standard polar	33892256
Gemfibrozil	CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1	1917.9	Standard non polar	33892256
Gemfibrozil	CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1	1926.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gemfibrozil,1TMS,isomer #1	CC1=CC=C(C)C(OCCCC(C)(C)C(=O)O[Si](C)(C)C)=C1	1912.2	Semi standard non polar	33892256
Gemfibrozil,1TBDMS,isomer #1	CC1=CC=C(C)C(OCCCC(C)(C)C(=O)O[Si](C)(C)C(C)(C)C)=C1	2156.4	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 - Gemfibrozil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-6950000000-ea8e6e101df62d80313a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gemfibrozil GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-9721000000-e7c61af259566e389d95	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gemfibrozil 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 - Gemfibrozil LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-24b892a8bd68bdf9cef6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-7a9eaaae65f0e1efcbc4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-12b36ea4be2a1b876c61	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-647692900acca2ec2441	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-41c8e4e08162dfaf1fc4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-28d25da91cc1d391cc84	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-a08267bdc97edb1a2601	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-a133a90a69b988c45ffb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , positive-QTOF	splash10-0059-6910000000-0ad597adcb83e9f4e4ba	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , positive-QTOF	splash10-0059-8900000000-8684ba342d3eb0a7f602	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , positive-QTOF	splash10-05cr-9400000000-008385b887cc6ac6d748	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , positive-QTOF	splash10-0ac0-9300000000-74e1b5c007dd49af6a01	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , positive-QTOF	splash10-0ab9-9200000000-cc36aaee7c70d8e92f96	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil LC-ESI-QFT , positive-QTOF	splash10-0a4i-9100000000-ce28ed926945c33079d6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil 90V, Negative-QTOF	splash10-052g-9400000000-7df8d3b3c3d528585b24	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil 75V, Positive-QTOF	splash10-0ab9-9200000000-a29f6ecb2573b0a72463	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil 90V, Positive-QTOF	splash10-0a4i-9100000000-ce28ed926945c33079d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil 10V, Positive-QTOF	splash10-004i-0970000000-b6b747ddc80c5e277857	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Gemfibrozil 30V, Negative-QTOF	splash10-0002-0390000000-b42eee5672459e8cc06b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gemfibrozil 10V, Positive-QTOF	splash10-0zfr-0290000000-ed946d5de4de22b6bf20	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gemfibrozil 20V, Positive-QTOF	splash10-0a59-4970000000-01a0d2adb215feef78cc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gemfibrozil 40V, Positive-QTOF	splash10-053r-9500000000-f971c24cd2f474fea5a3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gemfibrozil 10V, Negative-QTOF	splash10-0002-0490000000-2ba2ea9e2ef949ad859b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gemfibrozil 20V, Negative-QTOF	splash10-00di-1950000000-865193b239a02078f9b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gemfibrozil 40V, Negative-QTOF	splash10-00di-4900000000-adb1ff2509f9361f33fe	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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 DB01241	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01241	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

DB01241

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3345

KEGG Compound ID

C07020

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gemfibrozil

METLIN ID

Not Available

PubChem Compound

3463

PDB ID

Not Available

ChEBI ID

5296

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 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

2. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

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

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

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 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

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 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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. 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

Clavey V, Copin C, Mariotte MC, Bauge E, Chinetti G, Fruchart J, Fruchart JC, Dallongeville J, Staels B: Cell culture conditions determine apolipoprotein CIII secretion and regulation by fibrates in human hepatoma HepG2 cells. Cell Physiol Biochem. 1999;9(3):139-49. [PubMed:10494028 ]
Bosse Y, Pascot A, Dumont M, Brochu M, Prud'homme D, Bergeron J, Despres JP, Vohl MC: Influences of the PPAR alpha-L162V polymorphism on plasma HDL(2)-cholesterol response of abdominally obese men treated with gemfibrozil. Genet Med. 2002 Jul-Aug;4(4):311-5. [PubMed:12172398 ]
Pahan K, Jana M, Liu X, Taylor BS, Wood C, Fischer SM: Gemfibrozil, a lipid-lowering drug, inhibits the induction of nitric-oxide synthase in human astrocytes. J Biol Chem. 2002 Nov 29;277(48):45984-91. Epub 2002 Sep 18. [PubMed:12244038 ]
Shoji Y, Sanekata A, Sato M, Imaizumi K: Preparation of antiserum against rat delta6-desaturase and its use to evaluate the desaturase protein levels in rats treated with gemfibrozil, a ligand for peroxisome proliferator-activated receptor alpha. Biosci Biotechnol Biochem. 2003 May;67(5):1177-8. [PubMed:12834305 ]
Rizvi F, Iftikhar M, George JP: Beneficial effects of fish liver preparations of sea bass (Lates calcarifer) versus gemfibrozil in high fat diet-induced lipid-intolerant rats. J Med Food. 2003 Summer;6(2):123-8. [PubMed:12935323 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:: SLCO1B1
Uniprot ID:: Q9Y6L6
Molecular weight:: 76448.0

References

Sharma P, Holmes VE, Elsby R, Lambert C, Surry D: Validation of cell-based OATP1B1 assays to assess drug transport and the potential for drug-drug interaction to support regulatory submissions. Xenobiotica. 2010 Jan;40(1):24-37. doi: 10.3109/00498250903351013. [PubMed:19919292 ]

Showing metabocard for Gemfibrozil (HMDB0015371)

MOL for HMDB0015371 (Gemfibrozil)

3D MOL for HMDB0015371 (Gemfibrozil)

3D SDF for HMDB0015371 (Gemfibrozil)

3D-SDF for HMDB0015371 (Gemfibrozil)

PDB for HMDB0015371 (Gemfibrozil)

3D PDB for HMDB0015371 (Gemfibrozil)

SMILES for HMDB0015371 (Gemfibrozil)

INCHI for HMDB0015371 (Gemfibrozil)

Structure for HMDB0015371 (Gemfibrozil)

3D Structure for HMDB0015371 (Gemfibrozil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

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References

Transporters

References