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enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-10-17 09:52:37 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005031

Secondary Accession Numbers

HMDB05031

Metabolite Identification

Common Name

Rosiglitazone

Description

Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha-binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFκB) levels fall and inhibitor (IκB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes; Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. It is being marketed as Avandia by the pharmaceutical company GlaxoSmithKline, both as a standalone preparation and in combination with metformin (Avandamet). Another combination drug approved by the FDA is Avandaryl (with glimepiride); Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFkB) levels fall and inhibitor (IkB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes.

Structure

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

HMDB0005031
     RDKit          3D
Rosiglitazone
 44 46  0  0  0  0  0  0  0  0999 V2000
   -3.5601   -1.5718   -1.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216   -0.6297   -0.5996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -0.2330    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533    0.6091   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4450    1.1129   -0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.6064   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -0.7270   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377   -1.2010    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3104   -0.2743    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -0.7901    0.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -0.8179   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1392   -1.4622   -0.0394 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9497    0.1368    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1485    0.3167    0.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8972    1.0687    0.0096 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102    0.5918   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697    1.1867   -1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    1.0882    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    1.5069    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -0.0659   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8722   -0.8144    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0653   -0.2026    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2407    1.1587    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1961    1.8717    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0525    1.2736   -0.3248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817   -1.0733   -2.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7150   -2.2945   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -2.1863   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6174    0.4234    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826   -1.0863    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793   -0.1118   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3575    1.3548   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534   -1.4720   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549   -2.2535    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5860   -1.8006    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1278   -0.1543    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0504   -1.3550   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8508    2.0173    0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    1.7846    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701    2.5620    0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7704   -1.8960    0.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8853   -0.8074    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1588    1.6657    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527    2.9450   -0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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M  END


  Mrv0541 11291314372D          

 25 27  0  0  0  0            999 V2000
    7.2598    0.4956    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6012    0.0785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0988    2.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4024   -0.4296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577    0.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4793    1.0385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287    0.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1736    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4591    1.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7447    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9273    1.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1722    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7447    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0302    1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0668    0.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4577    1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7432   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287   -1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857    0.0785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857   -0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 19  1  0  0  0  0
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  7 24  2  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  1  0  0  0  0
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 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005031

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

> <INCHI_KEY>
YASAKCUCGLMORW-UHFFFAOYSA-N

> <FORMULA>
C18H19N3O3S

> <MOLECULAR_WEIGHT>
357.427

> <EXACT_MASS>
357.114712179

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.802626142874665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.446347898605694

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.059949534231166

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.844312266695456

> <JCHEM_PKA_STRONGEST_BASIC>
6.228630838640058

> <JCHEM_POLAR_SURFACE_AREA>
71.53

> <JCHEM_REFRACTIVITY>
97.78990000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rosiglitazone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005031
     RDKit          3D
Rosiglitazone
 44 46  0  0  0  0  0  0  0  0999 V2000
   -3.5601   -1.5718   -1.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216   -0.6297   -0.5996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -0.2330    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533    0.6091   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4450    1.1129   -0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.6064   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -0.7270   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377   -1.2010    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3104   -0.2743    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -0.7901    0.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -0.8179   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1392   -1.4622   -0.0394 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9497    0.1368    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1485    0.3167    0.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8972    1.0687    0.0096 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102    0.5918   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697    1.1867   -1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    1.0882    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    1.5069    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -0.0659   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8722   -0.8144    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0653   -0.2026    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2407    1.1587    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1961    1.8717    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0525    1.2736   -0.3248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817   -1.0733   -2.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7150   -2.2945   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2527    2.9450   -0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
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 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 29-NOV-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-NOV-13         0                                  
HETATM    1  S   UNK     0      13.552   0.925   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.722   0.147   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.118   4.589   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.684  -0.802   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       2.721   0.917   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      15.828   1.939   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       0.054   0.917   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      13.391   2.457   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.057   3.227   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.723   2.457   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.798   3.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.055   0.147   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.723   0.917   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.390   3.227   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.389   0.917   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.056   0.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.390   0.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.056   2.457   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.058   0.605   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.387   0.147   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.721   2.457   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.387  -1.393   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.054  -2.163   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.280   0.147   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.280  -1.393   0.000  0.00  0.00           C+0
CONECT    1    8   19                                                       
CONECT    2   15   16                                                       
CONECT    3   11                                                            
CONECT    4   19                                                            
CONECT    5   12   20   21                                                  
CONECT    6   11   19                                                       
CONECT    7   20   24                                                       
CONECT    8    1    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9   13   14                                                  
CONECT   11    3    6    8                                                  
CONECT   12    5   15                                                       
CONECT   13   10   17                                                       
CONECT   14   10   18                                                       
CONECT   15    2   12                                                       
CONECT   16    2   17   18                                                  
CONECT   17   13   16                                                       
CONECT   18   14   16                                                       
CONECT   19    1    4    6                                                  
CONECT   20    5    7   22                                                  
CONECT   21    5                                                            
CONECT   22   20   23                                                       
CONECT   23   22   25                                                       
CONECT   24    7   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0005031
HETATM    1  C1  UNL     1      -3.560  -1.572  -1.677  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.622  -0.630  -0.600  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.371  -0.233   0.048  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.653   0.609  -0.986  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.445   1.113  -0.628  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.756   0.606  -0.296  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.078  -0.727  -0.249  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.338  -1.201   0.100  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.310  -0.274   0.413  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.659  -0.790   0.760  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.501  -0.818  -0.507  1.00  0.00           C  
HETATM   12  S1  UNL     1       7.139  -1.462  -0.039  1.00  0.00           S  
HETATM   13  C10 UNL     1       7.950   0.137   0.239  1.00  0.00           C  
HETATM   14  O2  UNL     1       9.149   0.317   0.553  1.00  0.00           O  
HETATM   15  N2  UNL     1       6.897   1.069   0.010  1.00  0.00           N  
HETATM   16  C11 UNL     1       5.910   0.592  -0.867  1.00  0.00           C  
HETATM   17  O3  UNL     1       5.370   1.187  -1.863  1.00  0.00           O  
HETATM   18  C12 UNL     1       3.039   1.088   0.382  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.784   1.507   0.033  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.845  -0.066  -0.204  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.872  -0.814   0.312  1.00  0.00           C  
HETATM   22  C16 UNL     1      -7.065  -0.203   0.686  1.00  0.00           C  
HETATM   23  C17 UNL     1      -7.241   1.159   0.549  1.00  0.00           C  
HETATM   24  C18 UNL     1      -6.196   1.872   0.032  1.00  0.00           C  
HETATM   25  N3  UNL     1      -5.053   1.274  -0.325  1.00  0.00           N  
HETATM   26  H1  UNL     1      -3.382  -1.073  -2.655  1.00  0.00           H  
HETATM   27  H2  UNL     1      -2.715  -2.295  -1.561  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.487  -2.186  -1.723  1.00  0.00           H  
HETATM   29  H4  UNL     1      -2.617   0.423   0.912  1.00  0.00           H  
HETATM   30  H5  UNL     1      -1.783  -1.086   0.393  1.00  0.00           H  
HETATM   31  H6  UNL     1      -1.479  -0.112  -1.855  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.358   1.355  -1.435  1.00  0.00           H  
HETATM   33  H8  UNL     1       0.353  -1.472  -0.490  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.555  -2.254   0.128  1.00  0.00           H  
HETATM   35  H10 UNL     1       4.586  -1.801   1.172  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.128  -0.154   1.528  1.00  0.00           H  
HETATM   37  H12 UNL     1       5.050  -1.355  -1.331  1.00  0.00           H  
HETATM   38  H13 UNL     1       6.851   2.017   0.450  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.838   1.785   0.636  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.570   2.562   0.007  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.770  -1.896   0.438  1.00  0.00           H  
HETATM   42  H17 UNL     1      -7.885  -0.807   1.093  1.00  0.00           H  
HETATM   43  H18 UNL     1      -8.159   1.666   0.827  1.00  0.00           H  
HETATM   44  H19 UNL     1      -6.253   2.945  -0.108  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   20
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   10   18
CONECT   10   11   35   36
CONECT   11   12   16   37
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   38
CONECT   16   17   17
CONECT   18   19   19   39
CONECT   19   40
CONECT   20   21   21   25
CONECT   21   22   41
CONECT   22   23   23   42
CONECT   23   24   43
CONECT   24   25   25   44
END

HMDB0005031
     RDKit          3D
Rosiglitazone
 44 46  0  0  0  0  0  0  0  0999 V2000
   -3.5601   -1.5718   -1.6769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6216   -0.6297   -0.5996 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3708   -0.2330    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6533    0.6091   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4450    1.1129   -0.6285 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7562    0.6064   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -0.7270   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3377   -1.2010    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3104   -0.2743    0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6590   -0.7901    0.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -0.8179   -0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1392   -1.4622   -0.0394 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9497    0.1368    0.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1485    0.3167    0.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8972    1.0687    0.0096 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9102    0.5918   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3697    1.1867   -1.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390    1.0882    0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    1.5069    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -0.0659   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8722   -0.8144    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0653   -0.2026    0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2407    1.1587    0.5486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1961    1.8717    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0525    1.2736   -0.3248 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817   -1.0733   -2.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7150   -2.2945   -1.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4874   -2.1863   -1.7228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6174    0.4234    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7826   -1.0863    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4793   -0.1118   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3575    1.3548   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534   -1.4720   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549   -2.2535    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5860   -1.8006    1.1718 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1278   -0.1543    1.5277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0504   -1.3550   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8508    2.0173    0.4495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    1.7846    0.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5701    2.5620    0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7704   -1.8960    0.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8853   -0.8074    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1588    1.6657    0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2527    2.9450   -0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  2  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 19  6  1  0
 25 20  1  0
 16 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 15 38  1  0
 18 39  1  0
 19 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-((4-(2-(Methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione	ChEBI
BRL-49653	ChEBI
Rosiglitazona	ChEBI
Rosiglitazonum	ChEBI
Gaudil	Kegg
Avandia	HMDB
Rosiglitazone maleate	HMDB
Rosiglizole	HMDB
5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate	HMDB
GlaxoSmithKline brand OF rosiglitazone maleate	HMDB
SmithKline beecham brand OF rosiglitazone maleate	HMDB
Glaxo wellcome brand OF rosiglitazone maleate	HMDB

Chemical Formula

C₁₈H₁₉N₃O₃S

Average Molecular Weight

357.427

Monoisotopic Molecular Weight

357.114712179

IUPAC Name

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

Traditional Name

rosiglitazone

CAS Registry Number

122320-73-4

SMILES

CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1

InChI Identifier

InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

InChI Key

YASAKCUCGLMORW-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
Dialkylarylamine
Alkyl aryl ether
Aminopyridine
Monocyclic benzene moiety
Pyridine
Imidolactam
Heteroaromatic compound
Meta-thiazoline
Carbonic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aminopyridine (CHEBI:50122 )
thiazolidenediones (CHEBI:50122 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0005031)

Cellular substructure

Membrane (HMDB: HMDB0005031)

Process

Naturally occurring process

Biological process

Biochemical pathway

Rosiglitazone Metabolism Pathway (HMDB: HMDB0005031)

Metabolic pathway

Rosiglitazone Metabolism Pathway (PathBank: SMP0000653)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005031)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	172.62	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000747

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	2.95	ALOGPS
logP	2.45	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	6.84	ChemAxon
pKa (Strongest Basic)	6.23	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	37.8 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]+	182.448	31661259
DarkChem	[M-H]-	178.784	31661259
DeepCCS	[M+H]+	177.975	30932474
DeepCCS	[M-H]-	175.617	30932474
DeepCCS	[M-2H]-	208.503	30932474
DeepCCS	[M+Na]+	184.068	30932474
AllCCS	[M+H]+	185.8	32859911
AllCCS	[M+H-H2O]+	182.9	32859911
AllCCS	[M+NH4]+	188.5	32859911
AllCCS	[M+Na]+	189.3	32859911
AllCCS	[M-H]-	184.2	32859911
AllCCS	[M+Na-2H]-	184.1	32859911
AllCCS	[M+HCOO]-	184.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rosiglitazone	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1	4277.8	Standard polar	33892256
Rosiglitazone	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1	3210.3	Standard non polar	33892256
Rosiglitazone	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1	3296.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=CC=CC=N1	3273.2	Semi standard non polar	33892256
Rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=CC=CC=N1	3068.8	Standard non polar	33892256
Rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=CC=CC=N1	4246.2	Standard polar	33892256
Rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=CC=CC=N1	3494.7	Semi standard non polar	33892256
Rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=CC=CC=N1	3285.6	Standard non polar	33892256
Rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=CC=CC=N1	4234.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-6931000000-a3ad698c8739c8f57e74	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Rosiglitazone 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 - Rosiglitazone LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0109000000-d527d5c2b5f1de352264	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosiglitazone , positive-QTOF	splash10-0a4i-0109000000-d527d5c2b5f1de352264	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosiglitazone , positive-QTOF	splash10-0a4r-1609000000-585d240b82e4a1918a29	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosiglitazone , positive-QTOF	splash10-0a4i-0309000000-a9fa2307075b611cffcc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosiglitazone 35V, Negative-QTOF	splash10-0a4i-1009000000-991ab6592f05f0e9b3b4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Rosiglitazone 35V, Positive-QTOF	splash10-052r-0906000000-d2389ebced7cec4a890e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 10V, Positive-QTOF	splash10-0a4i-0119000000-afcd19b8a0a922a55f1a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 20V, Positive-QTOF	splash10-052r-0941000000-369864aa78ee259dca92	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 40V, Positive-QTOF	splash10-0a4i-1910000000-f9a7e77fcdf7ededf79c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 10V, Negative-QTOF	splash10-0a4i-0439000000-ab505f9372d95dd2a762	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 20V, Negative-QTOF	splash10-0k9l-4792000000-bfe60ce181bc6c7314cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 40V, Negative-QTOF	splash10-0006-9500000000-9699ab9cf1188cacce3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 10V, Negative-QTOF	splash10-0a4i-1159000000-cd81e0c7b3e3f0631336	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 20V, Negative-QTOF	splash10-0006-9242000000-b5f05b953b17b8f5dc01	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 40V, Negative-QTOF	splash10-0006-9100000000-1495c41f9621c21b07f3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 10V, Positive-QTOF	splash10-000i-0902000000-914f8b56c690e9af074d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 20V, Positive-QTOF	splash10-052r-0579000000-0ae28d63488de9c942ee	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rosiglitazone 40V, Positive-QTOF	splash10-05g0-0910000000-de9d0cd74d041cf2fe82	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Rosiglitazone Metabolism Pathway		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00412

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023598

KNApSAcK ID

Not Available

Chemspider ID

70383

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rosiglitazone

METLIN ID

Not Available

PubChem Compound

77999

PDB ID

Not Available

ChEBI ID

50122

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Manne Reddy, "Amorphous form of rosiglitazone maleate and process for preparation thereof." U.S. Patent US20040242658, issued December 02, 2004.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. 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

Enzyme Details

3. 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

Showing metabocard for Rosiglitazone (HMDB0005031)

MOL for HMDB0005031 (Rosiglitazone)

3D MOL for HMDB0005031 (Rosiglitazone)

3D SDF for HMDB0005031 (Rosiglitazone)

3D-SDF for HMDB0005031 (Rosiglitazone)

PDB for HMDB0005031 (Rosiglitazone)

3D PDB for HMDB0005031 (Rosiglitazone)

SMILES for HMDB0005031 (Rosiglitazone)

INCHI for HMDB0005031 (Rosiglitazone)

Structure for HMDB0005031 (Rosiglitazone)

3D Structure for HMDB0005031 (Rosiglitazone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes