Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015465

Secondary Accession Numbers

HMDB15465

Metabolite Identification

Common Name

Bezafibrate

Description

Bezafibrate, also known as bezatol SR or befizal, 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. Bezafibrate is a drug which is used for the treatment of primary hyperlipidaemia types iia, iib, iii, iv and v (fredrickson classification) corresponding to groups i, ii and iii of the european atherosclerosis society guidelines - when diet alone or improvements in lifestyle such as increased exercise or weight reduction do not lead to an adequate response. also for the treatment of secondary hyperlipidaemias, e.g. severe hypertriglyceridemias, when sufficient improvement does not occur after correction of the underlying disorder (e.g. diabetes mellitus). Bezafibrate is an extremely weak basic (essentially neutral) compound (based on its pKa). Benafibrate is used for the treatment of hyperlipidaemia.

Structure

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

HMDB0015465
     RDKit          3D
Bezafibrate
 45 46  0  0  0  0  0  0  0  0999 V2000
   -6.9890    0.2956    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5006    0.5044    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963    2.0193    0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7228   -0.2365   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3783   -0.4130   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071    0.5356   -1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    0.4495   -1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -0.5354   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433   -0.6826   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -0.0096   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060   -0.2537   -0.3251 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1202    0.2823    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572    0.9847    1.4664 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    0.0371    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536    0.6120    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7836    0.3908    0.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1752   -0.3743   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8889   -0.6118   -0.5498 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2583   -0.9461   -1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201   -0.7238   -0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -1.4707   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -1.4178    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3586    0.1951    1.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0737    0.8658    2.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209   -0.7567    2.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5657    0.6952    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1008   -0.7854   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1609    0.8379   -0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3066    2.2756   -0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1232    2.5901    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3655    2.3142    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    1.3525   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051    1.1667   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678   -1.7680   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976   -0.3233   -2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347   -0.4541    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    1.0621    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321   -0.8308   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652    1.2140    1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396    0.8211    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6238   -1.5325   -1.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -1.1852   -1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122   -2.2917    0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193   -2.1640    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274   -1.7344    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
  2 23  1  0
 23 24  2  0
 23 25  1  0
 22  5  1  0
 20 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 15 39  1  0
 16 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 25 45  1  0
M  END

1393
  Mrv0541 02231215282D          

 25 26  0  0  0  0            999 V2000
    2.3645   -5.0780    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    3.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    4.8222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.5847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    4.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    2.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3 18  1  0  0  0  0
  4 18  2  0  0  0  0
  5 19  2  0  0  0  0
  6 10  1  0  0  0  0
  6 19  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 11 16  2  0  0  0  0
 11 17  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015465

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H20ClNO4/c1-19(2,18(23)24)25-16-9-3-13(4-10-16)11-12-21-17(22)14-5-7-15(20)8-6-14/h3-10H,11-12H2,1-2H3,(H,21,22)(H,23,24)

> <INCHI_KEY>
IIBYAHWJQTYFKB-UHFFFAOYSA-N

> <FORMULA>
C19H20ClNO4

> <MOLECULAR_WEIGHT>
361.819

> <EXACT_MASS>
361.10808584

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.53029638155452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-{2-[(4-chlorophenyl)formamido]ethyl}phenoxy)-2-methylpropanoic acid

> <ALOGPS_LOGP>
3.97

> <JCHEM_LOGP>
3.986583345666667

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.745638150722503

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.82883068613538

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8434560009342841

> <JCHEM_POLAR_SURFACE_AREA>
75.63

> <JCHEM_REFRACTIVITY>
95.96050000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bezafibrate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015465
     RDKit          3D
Bezafibrate
 45 46  0  0  0  0  0  0  0  0999 V2000
   -6.9890    0.2956    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5006    0.5044    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963    2.0193    0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7228   -0.2365   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3783   -0.4130   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071    0.5356   -1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    0.4495   -1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -0.5354   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433   -0.6826   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -0.0096   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060   -0.2537   -0.3251 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1202    0.2823    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572    0.9847    1.4664 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    0.0371    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536    0.6120    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7836    0.3908    0.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1752   -0.3743   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8889   -0.6118   -0.5498 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2583   -0.9461   -1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201   -0.7238   -0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -1.4707   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -1.4178    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3586    0.1951    1.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0737    0.8658    2.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209   -0.7567    2.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5657    0.6952    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1008   -0.7854   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1609    0.8379   -0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3066    2.2756   -0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1232    2.5901    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3655    2.3142    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    1.3525   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051    1.1667   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678   -1.7680   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976   -0.3233   -2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347   -0.4541    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    1.0621    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321   -0.8308   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652    1.2140    1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396    0.8211    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6238   -1.5325   -1.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -1.1852   -1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122   -2.2917    0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193   -2.1640    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274   -1.7344    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
  2 23  1  0
 23 24  2  0
 23 25  1  0
 22  5  1  0
 20 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 15 39  1  0
 16 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1393                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.414  -9.479   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.081   5.921   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.748   9.001   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   6.691   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.080  -2.549   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.748  -2.549   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.415   6.691   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -0.239   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.301   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -1.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   4.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.645   8.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.185   5.358   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748   2.071   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415   2.071   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   3.611   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   3.611   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   7.461   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -3.319   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -4.859   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.748  -5.629   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -5.629   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.748  -7.169   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080  -7.169   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414  -7.939   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2    7   11                                                       
CONECT    3   18                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6   10   19                                                       
CONECT    7    2   12   13   18                                             
CONECT    8    9   10                                                       
CONECT    9    8   14   15                                                  
CONECT   10    6    8                                                       
CONECT   11    2   16   17                                                  
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    9   16                                                       
CONECT   15    9   17                                                       
CONECT   16   11   14                                                       
CONECT   17   11   15                                                       
CONECT   18    3    4    7                                                  
CONECT   19    5    6   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   25                                                       
CONECT   25    1   23   24                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0015465
HETATM    1  C1  UNL     1      -6.989   0.296   0.098  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.501   0.504   0.469  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.296   2.019   0.266  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.723  -0.237  -0.377  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.378  -0.413  -0.485  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.707   0.536  -1.271  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.359   0.449  -1.446  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.611  -0.535  -0.883  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.843  -0.683  -1.031  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.681  -0.010  -0.037  1.00  0.00           C  
HETATM   11  N1  UNL     1       3.106  -0.254  -0.325  1.00  0.00           N  
HETATM   12  C10 UNL     1       4.120   0.282   0.481  1.00  0.00           C  
HETATM   13  O2  UNL     1       3.757   0.985   1.466  1.00  0.00           O  
HETATM   14  C11 UNL     1       5.518   0.037   0.191  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.454   0.612   1.049  1.00  0.00           C  
HETATM   16  C13 UNL     1       7.784   0.391   0.790  1.00  0.00           C  
HETATM   17  C14 UNL     1       8.175  -0.374  -0.284  1.00  0.00           C  
HETATM   18 CL1  UNL     1       9.889  -0.612  -0.550  1.00  0.00          CL  
HETATM   19  C15 UNL     1       7.258  -0.946  -1.137  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.920  -0.724  -0.877  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.265  -1.471  -0.110  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.634  -1.418   0.091  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.359   0.195   1.880  1.00  0.00           C  
HETATM   24  O3  UNL     1      -6.074   0.866   2.704  1.00  0.00           O  
HETATM   25  O4  UNL     1      -4.521  -0.757   2.399  1.00  0.00           O  
HETATM   26  H1  UNL     1      -7.566   0.695   0.945  1.00  0.00           H  
HETATM   27  H2  UNL     1      -7.101  -0.785  -0.054  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.161   0.838  -0.849  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.307   2.276  -0.806  1.00  0.00           H  
HETATM   30  H5  UNL     1      -6.123   2.590   0.749  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.365   2.314   0.787  1.00  0.00           H  
HETATM   32  H7  UNL     1      -3.266   1.353  -1.749  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.805   1.167  -2.048  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.068  -1.768  -1.045  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.098  -0.323  -2.067  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.535  -0.454   0.987  1.00  0.00           H  
HETATM   37  H12 UNL     1       1.575   1.062   0.074  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.332  -0.831  -1.138  1.00  0.00           H  
HETATM   39  H14 UNL     1       6.165   1.214   1.895  1.00  0.00           H  
HETATM   40  H15 UNL     1       8.540   0.821   1.435  1.00  0.00           H  
HETATM   41  H16 UNL     1       7.624  -1.533  -1.958  1.00  0.00           H  
HETATM   42  H17 UNL     1       5.230  -1.185  -1.564  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.712  -2.292   0.371  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.119  -2.164   0.679  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.727  -1.734   2.411  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   23
CONECT    3   29   30   31
CONECT    4    5
CONECT    5    6    6   22
CONECT    6    7   32
CONECT    7    8    8   33
CONECT    8    9   21
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   38
CONECT   12   13   13   14
CONECT   14   15   15   20
CONECT   15   16   39
CONECT   16   17   17   40
CONECT   17   18   19
CONECT   19   20   20   41
CONECT   20   42
CONECT   21   22   22   43
CONECT   22   44
CONECT   23   24   24   25
CONECT   25   45
END

HMDB0015465
     RDKit          3D
Bezafibrate
 45 46  0  0  0  0  0  0  0  0999 V2000
   -6.9890    0.2956    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5006    0.5044    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963    2.0193    0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7228   -0.2365   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3783   -0.4130   -0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071    0.5356   -1.2708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3592    0.4495   -1.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -0.5354   -0.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433   -0.6826   -1.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6806   -0.0096   -0.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060   -0.2537   -0.3251 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1202    0.2823    0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572    0.9847    1.4664 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176    0.0371    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4536    0.6120    1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7836    0.3908    0.7904 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1752   -0.3743   -0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8889   -0.6118   -0.5498 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.2583   -0.9461   -1.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9201   -0.7238   -0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2655   -1.4707   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341   -1.4178    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3586    0.1951    1.8798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0737    0.8658    2.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209   -0.7567    2.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5657    0.6952    0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1008   -0.7854   -0.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1609    0.8379   -0.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3066    2.2756   -0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1232    2.5901    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3655    2.3142    0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663    1.3525   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051    1.1667   -2.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0678   -1.7680   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0976   -0.3233   -2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5347   -0.4541    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    1.0621    0.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321   -0.8308   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652    1.2140    1.8953 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5396    0.8211    1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6238   -1.5325   -1.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2296   -1.1852   -1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7122   -2.2917    0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1193   -2.1640    0.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7274   -1.7344    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
  2 23  1  0
 23 24  2  0
 23 25  1  0
 22  5  1  0
 20 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 15 39  1  0
 16 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(p-(2-(p-Chlorobenzamido)ethyl)phenoxy)-2-methylpropionic acid	ChEBI
Befizal	ChEBI
Bezafibrato	ChEBI
Bezafibratum	ChEBI
Bezalip	ChEBI
Bezatol SR	ChEBI
Cedur	ChEBI
2-(p-(2-(p-Chlorobenzamido)ethyl)phenoxy)-2-methylpropionate	Generator
Bezafibric acid	Generator
Bezafibrat	HMDB
Befibrat	HMDB
Beza puren	HMDB
Bezafibrat PB	HMDB
Bezafibrate elfar brand	HMDB
Bezafibrate isis brand	HMDB
Bezafibrate tad brand	HMDB
Eulitop	HMDB
Hennig brand OF bezafibrate	HMDB
Lipox	HMDB
Sklerofibrat	HMDB
Teva brand OF bezafibrate	HMDB
Durabezur	HMDB
Azupharma brand OF bezafibrate	HMDB
Beza lande	HMDB
Bezacur	HMDB
Bezafibrate berlin-chemie brand	HMDB
Bezafibrate hennig brand	HMDB
Bezafibrate hexal brand	HMDB
Bezafibrate merckle brand	HMDB
Bezafibrate teva brand	HMDB
Hexal brand OF bezafibrate	HMDB
Isis brand OF bezafibrate	HMDB
Lakeside brand OF bezafibrate	HMDB
PB, Bezafibrat	HMDB
Solibay	HMDB
Synthelabo brand OF bezafibrate	HMDB
Bayer brand OF bezafibrate	HMDB
Berlin chemie brand OF bezafibrate	HMDB
Berlin-chemie brand OF bezafibrate	HMDB
Beza-lande	HMDB
Beza-puren	HMDB
Bezafibrate synthelabo brand	HMDB
Bezafisal	HMDB
Bezamerck	HMDB
Béfizal	HMDB
Cryopharma brand OF bezafibrate	HMDB
Difaterol	HMDB
Elfar brand OF bezafibrate	HMDB
Merckle brand OF bezafibrate	HMDB
Roche brand OF bezafibrate	HMDB
Azufibrat	HMDB
Betapharm brand OF bezafibrate	HMDB
BezaLande	HMDB
BezaPuren	HMDB
Bezabeta	HMDB
Bezafibrate azupharma brand	HMDB
Bezafibrate bayer brand	HMDB
Bezafibrate betapharm brand	HMDB
Bezafibrate cryopharma brand	HMDB
Bezafibrate lakeside brand	HMDB
Bezafibrate roche brand	HMDB
Boehringer mannheim brand OF bezafibrate	HMDB
Reducterol	HMDB
Regadrin b	HMDB
TAD brand OF bezafibrate	HMDB

Chemical Formula

C₁₉H₂₀ClNO₄

Average Molecular Weight

361.819

Monoisotopic Molecular Weight

361.10808584

IUPAC Name

2-(4-{2-[(4-chlorophenyl)formamido]ethyl}phenoxy)-2-methylpropanoic acid

Traditional Name

bezafibrate

CAS Registry Number

41859-67-0

SMILES

CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O

InChI Identifier

InChI=1S/C19H20ClNO4/c1-19(2,18(23)24)25-16-9-3-13(4-10-16)11-12-21-17(22)14-5-7-15(20)8-6-14/h3-10H,11-12H2,1-2H3,(H,21,22)(H,23,24)

InChI Key

IIBYAHWJQTYFKB-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
4-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
Phenoxy compound
Phenol ether
Benzoyl
Chlorobenzene
Alkyl aryl ether
Halobenzene
Aryl chloride
Aryl halide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic nitrogen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:47612 )
monocarboxylic acid (CHEBI:47612 )
monocarboxylic acid amide (CHEBI:47612 )
monochlorobenzenes (CHEBI:47612 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015465)
Membrane (HMDB: HMDB0015465)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	186 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0016 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	3.97	ALOGPS
logP	3.99	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.83	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.63 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	95.96 m³·mol⁻¹	ChemAxon
Polarizability	37.53 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]+	181.473	30932474
DeepCCS	[M-H]-	179.115	30932474
DeepCCS	[M-2H]-	212.972	30932474
DeepCCS	[M+Na]+	188.596	30932474
AllCCS	[M+H]+	183.9	32859911
AllCCS	[M+H-H2O]+	181.1	32859911
AllCCS	[M+NH4]+	186.5	32859911
AllCCS	[M+Na]+	187.3	32859911
AllCCS	[M-H]-	185.1	32859911
AllCCS	[M+Na-2H]-	184.9	32859911
AllCCS	[M+HCOO]-	184.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bezafibrate	CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O	4167.9	Standard polar	33892256
Bezafibrate	CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O	2852.5	Standard non polar	33892256
Bezafibrate	CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O	2977.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bezafibrate,1TMS,isomer #1	CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(=O)O[Si](C)(C)C	2988.5	Semi standard non polar	33892256
Bezafibrate,1TMS,isomer #2	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C)C=C1)C(=O)O	2874.6	Semi standard non polar	33892256
Bezafibrate,2TMS,isomer #1	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2847.3	Semi standard non polar	33892256
Bezafibrate,2TMS,isomer #1	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2651.8	Standard non polar	33892256
Bezafibrate,2TMS,isomer #1	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	3244.7	Standard polar	33892256
Bezafibrate,1TBDMS,isomer #1	CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3253.1	Semi standard non polar	33892256
Bezafibrate,1TBDMS,isomer #2	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3170.9	Semi standard non polar	33892256
Bezafibrate,2TBDMS,isomer #1	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3356.3	Semi standard non polar	33892256
Bezafibrate,2TBDMS,isomer #1	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3092.0	Standard non polar	33892256
Bezafibrate,2TBDMS,isomer #1	CC(C)(OC1=CC=C(CCN(C(=O)C2=CC=C(Cl)C=C2)[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3403.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bezafibrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-1921000000-ed1d61965cb5663ba976	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bezafibrate GC-MS (1 TMS) - 70eV, Positive	splash10-000i-4921000000-cf3ec530f82c5fef8a3a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bezafibrate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bezafibrate 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 - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-ad4511ba17ddb3a6b528	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-03k9-0049000000-319540ed864d05b5a9e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-65fad146d0a2b8cc3aeb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-0uk9-1980000000-f98f5d510895c2946e24	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-0udi-1900000000-58a247b2b13eaf401a8a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-0udi-3900000000-82a7a949824b1efdbd18	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-03k9-0049000000-e56612834951c9281537	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-54280ef14ba8e69fb8fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-0fk9-1890000000-81049839e6d37ddb476a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-0udi-0900000000-3ff4da4d943e21e1f3a1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-0udi-2900000000-d499986dc5288dfff06c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-62a3f94f91039648ffe1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0390000000-52f95c54ab1946e7c69f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0190000000-5257df29ed69050f426d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-ced0d5dcc71914483b64	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-849460edc8b9e96e9749	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-QFT , negative-QTOF	splash10-00di-2392000000-f4f98f4b89b6ae9a88d1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , positive-QTOF	splash10-016r-0049000000-03924d783ef40666f558	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bezafibrate LC-ESI-ITFT , positive-QTOF	splash10-03di-0019000000-58ff2df39e2672d16d49	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezafibrate 10V, Positive-QTOF	splash10-03di-0139000000-610de57b431b6eaccb80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezafibrate 20V, Positive-QTOF	splash10-07fu-3975000000-315ebcbd95638a3d3b0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezafibrate 40V, Positive-QTOF	splash10-08g0-2910000000-2d6abee2d54effe38335	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezafibrate 10V, Negative-QTOF	splash10-03di-0219000000-13daa1136c7e69d084a8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezafibrate 20V, Negative-QTOF	splash10-0ir0-0955000000-59d63587ef6ff82c5b8e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bezafibrate 40V, Negative-QTOF	splash10-0w29-1910000000-7005220edef11728283c	2016-08-04	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 DB01393	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01393	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01393

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35728

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bezafibrate

METLIN ID

Not Available

PubChem Compound

39042

PDB ID

PEM

ChEBI ID

47612

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

Authors unspecified: Secondary prevention by raising HDL cholesterol and reducing triglycerides in patients with coronary artery disease. Circulation. 2000 Jul 4;102(1):21-7. [PubMed:10880410 ]
Tenenbaum A, Motro M, Fisman EZ, Schwammenthal E, Adler Y, Goldenberg I, Leor J, Boyko V, Mandelzweig L, Behar S: Peroxisome proliferator-activated receptor ligand bezafibrate for prevention of type 2 diabetes mellitus in patients with coronary artery disease. Circulation. 2004 May 11;109(18):2197-202. Epub 2004 May 3. [PubMed:15123532 ]
Tenenbaum A, Motro M, Fisman EZ, Tanne D, Boyko V, Behar S: Bezafibrate for the secondary prevention of myocardial infarction in patients with metabolic syndrome. Arch Intern Med. 2005 May 23;165(10):1154-60. [PubMed:15911729 ]
Tenenbaum A, Fisman EZ, Boyko V, Benderly M, Tanne D, Haim M, Matas Z, Motro M, Behar S: Attenuation of progression of insulin resistance in patients with coronary artery disease by bezafibrate. Arch Intern Med. 2006 Apr 10;166(7):737-41. [PubMed:16606809 ]
MEDSAFE [Link]

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 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

3. 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

4. Peroxisome proliferator-activated receptor gamma

General function:: Involved in DNA binding
Specific function:: Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:: PPARG
Uniprot ID:: P37231
Molecular weight:: 57619.6

References

Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [PubMed:16168052 ]

Enzyme Details

5. 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

Pedraza N, Solanes G, Carmona MC, Iglesias R, Vinas O, Mampel T, Vazquez M, Giralt M, Villarroya F: Impaired expression of the uncoupling protein-3 gene in skeletal muscle during lactation: fibrates and troglitazone reverse lactation-induced downregulation of the uncoupling protein-3 gene. Diabetes. 2000 Jul;49(7):1224-30. [PubMed:10909982 ]
Cabrero A, Alegret M, Sanchez R, Adzet T, Laguna JC, Vazquez M: Peroxisome proliferator-activated receptor alpha (PPARalpha) activators, bezafibrate and Wy-14,643, increase uncoupling protein-3 mRNA levels without modifying the mitochondrial membrane potential in primary culture of rat preadipocytes. Arch Biochem Biophys. 2000 Aug 15;380(2):353-9. [PubMed:10933891 ]
Inoue I, Goto S, Matsunaga T, Nakajima T, Awata T, Hokari S, Komoda T, Katayama S: The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. Metabolism. 2001 Jan;50(1):3-11. [PubMed:11172467 ]
Guan Y, Breyer MD: Peroxisome proliferator-activated receptors (PPARs): novel therapeutic targets in renal disease. Kidney Int. 2001 Jul;60(1):14-30. [PubMed:11422732 ]
Bonilla S, Redonnet A, Noel-Suberville C, Groubet R, Pallet V, Higueret P: Effect of a pharmacological activation of PPAR on the expression of RAR and TR in rat liver. J Physiol Biochem. 2001 Mar;57(1):1-8. [PubMed:11519881 ]
Goldenberg I, Benderly M, Goldbourt U: Update on the use of fibrates: focus on bezafibrate. Vasc Health Risk Manag. 2008;4(1):131-41. [PubMed:18629356 ]
Fruchart JC, Duriez P: Mode of action of fibrates in the regulation of triglyceride and HDL-cholesterol metabolism. Drugs Today (Barc). 2006 Jan;42(1):39-64. [PubMed:16511610 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

6. Peroxisome proliferator-activated receptor delta

General function:: Involved in DNA binding
Specific function:: Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. 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. Decreases expression of NPC1L1 once activated by a ligand
Gene Name:: PPARD
Uniprot ID:: Q03181
Molecular weight:: 49903.0

References

Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [PubMed:16168052 ]

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 Bezafibrate (HMDB0015465)

MOL for HMDB0015465 (Bezafibrate)

3D MOL for HMDB0015465 (Bezafibrate)

3D SDF for HMDB0015465 (Bezafibrate)

3D-SDF for HMDB0015465 (Bezafibrate)

PDB for HMDB0015465 (Bezafibrate)

3D PDB for HMDB0015465 (Bezafibrate)

SMILES for HMDB0015465 (Bezafibrate)

INCHI for HMDB0015465 (Bezafibrate)

Structure for HMDB0015465 (Bezafibrate)

3D Structure for HMDB0015465 (Bezafibrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

Transporters

References