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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (2) Show 9 proteins XML

enzymes (7)transporters (2) Show 9 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015264

Secondary Accession Numbers

HMDB15264

Metabolite Identification

Common Name

Pioglitazone

Description

Pioglitazone, also known as actos, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Pioglitazone is a very strong basic compound (based on its pKa). Pioglitazone is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound.

Structure

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

HMDB0015264
     RDKit          3D
Pioglitazone
 45 47  0  0  0  0  0  0  0  0999 V2000
    7.8653   -0.3007   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7813    0.0114   -1.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4785    0.0528   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7359   -1.0849   -0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -1.0158   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1054    0.1773    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    0.2889    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680   -1.0628    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428   -1.0378    1.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923   -0.3927    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823   -0.4851    2.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648    0.1420    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121    0.8547    0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    1.4915    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6516    0.6702   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2465    1.5095   -0.9557 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2301    0.0362   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4286   -0.0222   -1.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3636   -1.0189   -0.7366 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1771   -0.6160   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6420   -1.3257    0.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9333   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.3197    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8528    1.3147    0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0122    1.2165   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8653   -0.0395   -1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9241   -1.3902   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7324    0.3095    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9519    1.0099   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7460   -0.7704   -2.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632   -2.0424   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -1.9337   -0.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201    1.0912    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658    0.5933    2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0009   -1.4594    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8959   -1.7780    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -1.0474    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2655    0.0523    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    2.4661   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4936    1.7475    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1249    0.5670   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5095   -2.0522   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    1.4986   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    0.4110   -0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239    2.1108   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
  6 24  1  0
 24 25  2  0
 25  3  1  0
 23 10  1  0
 20 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 19 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

1132
  Mrv0541 02231215162D          

 25 27  0  0  1  0            999 V2000
    6.6906    2.6473    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4100    4.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0631    3.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8301    3.9749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.2047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0231    3.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2426    3.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.3796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 19  1  0  0  0  0
  2 14  1  0  0  0  0
  2 15  1  0  0  0  0
  3 10  2  0  0  0  0
  4 19  2  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  6 18  2  0  0  0  0
  6 24  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  2  0  0  0  0
 13 15  1  0  0  0  0
 13 18  1  0  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 23  2  0  0  0  0
 22 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015264

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)

> <INCHI_KEY>
HYAFETHFCAUJAY-UHFFFAOYSA-N

> <FORMULA>
C19H20N2O3S

> <MOLECULAR_WEIGHT>
356.439

> <EXACT_MASS>
356.119463206

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.91018046697517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.328248699886255

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.06037916460504

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.657648829932739

> <JCHEM_PKA_STRONGEST_BASIC>
5.598025373449761

> <JCHEM_POLAR_SURFACE_AREA>
68.29

> <JCHEM_REFRACTIVITY>
97.39080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pioglitazone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015264
     RDKit          3D
Pioglitazone
 45 47  0  0  0  0  0  0  0  0999 V2000
    7.8653   -0.3007   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7813    0.0114   -1.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4785    0.0528   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7359   -1.0849   -0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -1.0158   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1054    0.1773    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    0.2889    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680   -1.0628    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428   -1.0378    1.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923   -0.3927    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823   -0.4851    2.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648    0.1420    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121    0.8547    0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    1.4915    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6516    0.6702   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2465    1.5095   -0.9557 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2301    0.0362   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4286   -0.0222   -1.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3636   -1.0189   -0.7366 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1771   -0.6160   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6420   -1.3257    0.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9333   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.3197    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8528    1.3147    0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0122    1.2165   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8653   -0.0395   -1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9241   -1.3902   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7324    0.3095    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9519    1.0099   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7460   -0.7704   -2.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632   -2.0424   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -1.9337   -0.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201    1.0912    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658    0.5933    2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0009   -1.4594    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8959   -1.7780    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -1.0474    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2655    0.0523    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    2.4661   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4936    1.7475    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1249    0.5670   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5095   -2.0522   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    1.4986   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    0.4110   -0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239    2.1108   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
  6 24  1  0
 24 25  2  0
 25  3  1  0
 23 10  1  0
 20 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 19 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1132                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      12.489   4.942   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.748  -1.362   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.099   8.130   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.051   5.925   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      12.750   7.420   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081  -5.982   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      11.082   5.568   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   4.798   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   3.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.243   7.100   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   2.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   2.488   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -3.672   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748   0.178   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -2.132   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   0.948   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   0.948   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -4.442   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.520   6.086   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -5.982   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.747  -3.672   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -6.752   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -4.442   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.747  -6.752   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.080  -8.292   0.000  0.00  0.00           C+0
CONECT    1    7   19                                                       
CONECT    2   14   15                                                       
CONECT    3   10                                                            
CONECT    4   19                                                            
CONECT    5   10   19                                                       
CONECT    6   18   24                                                       
CONECT    7    1    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   11   12                                                  
CONECT   10    3    5    7                                                  
CONECT   11    9   16                                                       
CONECT   12    9   17                                                       
CONECT   13   15   18                                                       
CONECT   14    2   16   17                                                  
CONECT   15    2   13                                                       
CONECT   16   11   14                                                       
CONECT   17   12   14                                                       
CONECT   18    6   13   21                                                  
CONECT   19    1    4    5                                                  
CONECT   20   22   23   24                                                  
CONECT   21   18   23                                                       
CONECT   22   20   25                                                       
CONECT   23   20   21                                                       
CONECT   24    6   20                                                       
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0015264
HETATM    1  C1  UNL     1       7.865  -0.301  -0.733  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.781   0.011  -1.735  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.479   0.053  -1.003  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.736  -1.085  -0.868  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.521  -1.016  -0.178  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.105   0.177   0.343  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.823   0.289   1.082  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.168  -1.063   1.131  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.043  -1.038   1.786  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.192  -0.393   1.405  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.282  -0.485   2.270  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.465   0.142   1.934  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.612   0.855   0.780  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.878   1.491   0.425  1.00  0.00           C  
HETATM   15  C14 UNL     1      -5.652   0.670  -0.531  1.00  0.00           C  
HETATM   16  S1  UNL     1      -7.247   1.509  -0.956  1.00  0.00           S  
HETATM   17  C15 UNL     1      -8.230   0.036  -1.048  1.00  0.00           C  
HETATM   18  O2  UNL     1      -9.429  -0.022  -1.331  1.00  0.00           O  
HETATM   19  N1  UNL     1      -7.364  -1.019  -0.737  1.00  0.00           N  
HETATM   20  C16 UNL     1      -6.177  -0.616  -0.056  1.00  0.00           C  
HETATM   21  O3  UNL     1      -5.642  -1.326   0.875  1.00  0.00           O  
HETATM   22  C17 UNL     1      -2.527   0.933  -0.057  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.337   0.320   0.249  1.00  0.00           C  
HETATM   24  N2  UNL     1       3.853   1.315   0.205  1.00  0.00           N  
HETATM   25  C19 UNL     1       5.012   1.217  -0.461  1.00  0.00           C  
HETATM   26  H1  UNL     1       8.865  -0.040  -1.180  1.00  0.00           H  
HETATM   27  H2  UNL     1       7.924  -1.390  -0.510  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.732   0.310   0.184  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.952   1.010  -2.167  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.746  -0.770  -2.516  1.00  0.00           H  
HETATM   31  H6  UNL     1       5.063  -2.042  -1.283  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.942  -1.934  -0.082  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.220   1.091   0.687  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.066   0.593   2.163  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.001  -1.459   0.089  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.896  -1.778   1.611  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.168  -1.047   3.180  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.265   0.052   2.653  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.602   2.466  -0.085  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.494   1.747   1.320  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.125   0.567  -1.513  1.00  0.00           H  
HETATM   42  H17 UNL     1      -7.509  -2.052  -0.956  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.595   1.499  -1.003  1.00  0.00           H  
HETATM   44  H19 UNL     1      -0.541   0.411  -0.482  1.00  0.00           H  
HETATM   45  H20 UNL     1       5.624   2.111  -0.583  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4   25
CONECT    4    5   31
CONECT    5    6    6   32
CONECT    6    7   24
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10
CONECT   10   11   11   23
CONECT   11   12   37
CONECT   12   13   13   38
CONECT   13   14   22
CONECT   14   15   39   40
CONECT   15   16   20   41
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   20   42
CONECT   20   21   21
CONECT   22   23   23   43
CONECT   23   44
CONECT   24   25   25
CONECT   25   45
END

HMDB0015264
     RDKit          3D
Pioglitazone
 45 47  0  0  0  0  0  0  0  0999 V2000
    7.8653   -0.3007   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7813    0.0114   -1.7351 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4785    0.0528   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7359   -1.0849   -0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -1.0158   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1054    0.1773    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232    0.2889    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680   -1.0628    1.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0428   -1.0378    1.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1923   -0.3927    1.4053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823   -0.4851    2.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4648    0.1420    1.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6121    0.8547    0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    1.4915    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6516    0.6702   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2465    1.5095   -0.9557 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2301    0.0362   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4286   -0.0222   -1.3311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3636   -1.0189   -0.7366 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1771   -0.6160   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6420   -1.3257    0.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5275    0.9333   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.3197    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8528    1.3147    0.2052 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0122    1.2165   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8653   -0.0395   -1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9241   -1.3902   -0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7324    0.3095    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9519    1.0099   -2.1666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7460   -0.7704   -2.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632   -2.0424   -1.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -1.9337   -0.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201    1.0912    0.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0658    0.5933    2.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0009   -1.4594    0.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8959   -1.7780    1.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1678   -1.0474    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2655    0.0523    2.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019    2.4661   -0.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4936    1.7475    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1249    0.5670   -1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5095   -2.0522   -0.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948    1.4986   -1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    0.4110   -0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239    2.1108   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
  6 24  1  0
 24 25  2  0
 25  3  1  0
 23 10  1  0
 20 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 19 42  1  0
 22 43  1  0
 23 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-5-((4-(2-(5-Ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione	ChEBI
Pioglitazona	ChEBI
Pioglitazonum	ChEBI
Actos	Kegg
Pioglitazone HCL	HMDB
Pioglitazone hydrochloride	HMDB
5-(4-(2-(5-Ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione	HMDB
Poglitazone hydrochloride	HMDB

Chemical Formula

C₁₉H₂₀N₂O₃S

Average Molecular Weight

356.439

Monoisotopic Molecular Weight

356.119463206

IUPAC Name

5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione

Traditional Name

pioglitazone

CAS Registry Number

111025-46-8

SMILES

CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1

InChI Identifier

InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)

InChI Key

HYAFETHFCAUJAY-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
Phenol ether
Alkyl aryl ether
Thiazolidinedione
Monocyclic benzene moiety
Pyridine
Dicarboximide
Heteroaromatic compound
Thiazolidine
Carbonic acid derivative
Thiocarbamic acid derivative
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:8228 )
pyridines (CHEBI:8228 )
thiazolidenediones (CHEBI:8228 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015264)
Membrane (HMDB: HMDB0015264)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 - 184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0044 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0044 g/L	ALOGPS
logP	3.17	ALOGPS
logP	3.33	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	5.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.39 m³·mol⁻¹	ChemAxon
Polarizability	37.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	184.854	31661259
DarkChem	[M-H]-	185.645	31661259
DeepCCS	[M+H]+	183.774	30932474
DeepCCS	[M-H]-	181.284	30932474
DeepCCS	[M-2H]-	215.693	30932474
DeepCCS	[M+Na]+	191.982	30932474
AllCCS	[M+H]+	186.4	32859911
AllCCS	[M+H-H2O]+	183.5	32859911
AllCCS	[M+NH4]+	189.0	32859911
AllCCS	[M+Na]+	189.8	32859911
AllCCS	[M-H]-	185.3	32859911
AllCCS	[M+Na-2H]-	185.2	32859911
AllCCS	[M+HCOO]-	185.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pioglitazone	CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1	4423.4	Standard polar	33892256
Pioglitazone	CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1	3285.6	Standard non polar	33892256
Pioglitazone	CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1	3244.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pioglitazone,1TMS,isomer #1	CCC1=CC=C(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	3354.6	Semi standard non polar	33892256
Pioglitazone,1TMS,isomer #1	CCC1=CC=C(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	3126.0	Standard non polar	33892256
Pioglitazone,1TMS,isomer #1	CCC1=CC=C(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	4110.4	Standard polar	33892256
Pioglitazone,1TBDMS,isomer #1	CCC1=CC=C(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	3580.3	Semi standard non polar	33892256
Pioglitazone,1TBDMS,isomer #1	CCC1=CC=C(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	3333.4	Standard non polar	33892256
Pioglitazone,1TBDMS,isomer #1	CCC1=CC=C(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	4107.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pioglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-0982000000-bc531fd621e090712033	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pioglitazone 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 - Pioglitazone LC-ESI-QFT , negative-QTOF	splash10-0a4i-0009000000-070cf69939743719671d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , negative-QTOF	splash10-0bt9-0209000000-d9d34be41f49a9ffbdef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-ef25b6f93ae4fcee23c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , negative-QTOF	splash10-0udi-0900000000-3011f00e839bfc06d89d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , negative-QTOF	splash10-0gba-0900000000-b0488e0d155d1587bbb5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , negative-QTOF	splash10-014j-0900000000-b32570ad6af58a4a6c72	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , negative-QTOF	splash10-0a4i-0009000000-c67370f6cb2ad36cab3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QTOF , positive-QTOF	splash10-0a59-0908000000-aab2ee9addb1334a7064	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , positive-QTOF	splash10-0a4i-0009000000-fd4bc4d9d4bb45e91295	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , positive-QTOF	splash10-0a4i-0409000000-115c6889c4e9205b3028	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-a2e878da4d2f6a4bb717	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-031fa259cd3b26217dad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , positive-QTOF	splash10-00lr-0900000000-e2cd3c294a2e53e1a17e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , positive-QTOF	splash10-0159-1900000000-aacbd8dce006b5ef5938	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone , positive-QTOF	splash10-0a4i-1619000000-4b248e31af7f50e87108	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone LC-ESI-QFT , positive-QTOF	splash10-053r-0906000000-a73152b364036b45dfeb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone 45V, Negative-QTOF	splash10-0udi-0900000000-4cbb6d60c5b330f46e83	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone 30V, Negative-QTOF	splash10-0bt9-0009000000-e15320a688303951fc88	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pioglitazone 60V, Negative-QTOF	splash10-0udi-0900000000-83eb5dacf9c310e76b61	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pioglitazone 10V, Positive-QTOF	splash10-0a4i-0219000000-989038e0dc6e9a9ecf80	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pioglitazone 20V, Positive-QTOF	splash10-0540-0984000000-b1e6f3241976f6936760	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pioglitazone 40V, Positive-QTOF	splash10-0kai-1900000000-8b2d810f6330f368aa47	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pioglitazone 10V, Negative-QTOF	splash10-0a4i-0159000000-0b74a48747ffb1b4f2d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pioglitazone 20V, Negative-QTOF	splash10-0uec-3692000000-141c6eb446379ead16bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pioglitazone 40V, Negative-QTOF	splash10-0f6x-9700000000-a10d6ccf2ad58937dfa5	2016-08-03	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	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01132	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01132	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01132

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4663

KEGG Compound ID

C07675

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pioglitazone

METLIN ID

Not Available

PubChem Compound

4829

PDB ID

Not Available

ChEBI ID

8228

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

Paddock ML, Wiley SE, Axelrod HL, Cohen AE, Roy M, Abresch EC, Capraro D, Murphy AN, Nechushtai R, Dixon JE, Jennings PA: MitoNEET is a uniquely folded 2Fe 2S outer mitochondrial membrane protein stabilized by pioglitazone. Proc Natl Acad Sci U S A. 2007 Sep 4;104(36):14342-7. Epub 2007 Aug 31. [PubMed:17766440 ]
Colca JR, McDonald WG, Waldon DJ, Leone JW, Lull JM, Bannow CA, Lund ET, Mathews WR: Identification of a novel mitochondrial protein ("mitoNEET") cross-linked specifically by a thiazolidinedione photoprobe. Am J Physiol Endocrinol Metab. 2004 Feb;286(2):E252-60. Epub 2003 Oct 21. [PubMed:14570702 ]
Lincoff AM, Wolski K, Nicholls SJ, Nissen SE: Pioglitazone and risk of cardiovascular events in patients with type 2 diabetes mellitus: a meta-analysis of randomized trials. JAMA. 2007 Sep 12;298(10):1180-8. [PubMed:17848652 ]

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. 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

Jaakkola T, Laitila J, Neuvonen PJ, Backman JT: Pioglitazone is metabolised by CYP2C8 and CYP3A4 in vitro: potential for interactions with CYP2C8 inhibitors. Basic Clin Pharmacol Toxicol. 2006 Jul;99(1):44-51. [PubMed:16867170 ]
Sahi J, Black CB, Hamilton GA, Zheng X, Jolley S, Rose KA, Gilbert D, LeCluyse EL, Sinz MW: Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46. [PubMed:12642470 ]
Nowak SN, Edwards DJ, Clarke A, Anderson GD, Jaber LA: Pioglitazone: effect on CYP3A4 activity. J Clin Pharmacol. 2002 Dec;42(12):1299-302. [PubMed:12463723 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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 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

4. 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

5. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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 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

Muschler E, Lal J, Jetter A, Rattay A, Zanger U, Zadoyan G, Fuhr U, Kirchheiner J: The role of human CYP2C8 and CYP2C9 variants in pioglitazone metabolism in vitro. Basic Clin Pharmacol Toxicol. 2009 Dec;105(6):374-9. doi: 10.1111/j.1742-7843.2009.00457.x. Epub 2009 Jul 15. [PubMed:19614891 ]
Jaakkola T, Laitila J, Neuvonen PJ, Backman JT: Pioglitazone is metabolised by CYP2C8 and CYP3A4 in vitro: potential for interactions with CYP2C8 inhibitors. Basic Clin Pharmacol Toxicol. 2006 Jul;99(1):44-51. [PubMed:16867170 ]
Sahi J, Black CB, Hamilton GA, Zheng X, Jolley S, Rose KA, Gilbert D, LeCluyse EL, Sinz MW: Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46. [PubMed:12642470 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Sugii S, Olson P, Sears DD, Saberi M, Atkins AR, Barish GD, Hong SH, Castro GL, Yin YQ, Nelson MC, Hsiao G, Greaves DR, Downes M, Yu RT, Olefsky JM, Evans RM: PPARgamma activation in adipocytes is sufficient for systemic insulin sensitization. Proc Natl Acad Sci U S A. 2009 Dec 29;106(52):22504-9. doi: 10.1073/pnas.0912487106. Epub 2009 Dec 16. [PubMed:20018750 ]
Miyazaki Y, Mahankali A, Wajcberg E, Bajaj M, Mandarino LJ, DeFronzo RA: Effect of pioglitazone on circulating adipocytokine levels and insulin sensitivity in type 2 diabetic patients. J Clin Endocrinol Metab. 2004 Sep;89(9):4312-9. [PubMed:15356026 ]
Lehmann JM, Moore LB, Smith-Oliver TA, Wilkison WO, Willson TM, Kliewer SA: An antidiabetic thiazolidinedione is a high affinity ligand for peroxisome proliferator-activated receptor gamma (PPAR gamma). J Biol Chem. 1995 Jun 2;270(22):12953-6. [PubMed:7768881 ]
Spiegelman BM: PPAR-gamma: adipogenic regulator and thiazolidinedione receptor. Diabetes. 1998 Apr;47(4):507-14. [PubMed:9568680 ]
Willson TM, Cobb JE, Cowan DJ, Wiethe RW, Correa ID, Prakash SR, Beck KD, Moore LB, Kliewer SA, Lehmann JM: The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem. 1996 Feb 2;39(3):665-8. [PubMed:8576907 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1B3

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:: SLCO1B3
Uniprot ID:: Q9NPD5
Molecular weight:: 77402.2

References

Nozawa T, Sugiura S, Nakajima M, Goto A, Yokoi T, Nezu J, Tsuji A, Tamai I: Involvement of organic anion transporting polypeptides in the transport of troglitazone sulfate: implications for understanding troglitazone hepatotoxicity. Drug Metab Dispos. 2004 Mar;32(3):291-4. [PubMed:14977862 ]

Enzyme Details

2. 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

Nozawa T, Sugiura S, Nakajima M, Goto A, Yokoi T, Nezu J, Tsuji A, Tamai I: Involvement of organic anion transporting polypeptides in the transport of troglitazone sulfate: implications for understanding troglitazone hepatotoxicity. Drug Metab Dispos. 2004 Mar;32(3):291-4. [PubMed:14977862 ]

Showing metabocard for Pioglitazone (HMDB0015264)

MOL for HMDB0015264 (Pioglitazone)

3D MOL for HMDB0015264 (Pioglitazone)

3D SDF for HMDB0015264 (Pioglitazone)

3D-SDF for HMDB0015264 (Pioglitazone)

PDB for HMDB0015264 (Pioglitazone)

3D PDB for HMDB0015264 (Pioglitazone)

SMILES for HMDB0015264 (Pioglitazone)

INCHI for HMDB0015264 (Pioglitazone)

Structure for HMDB0015264 (Pioglitazone)

3D Structure for HMDB0015264 (Pioglitazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References

References