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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:02:55 UTC

Update Date

2021-09-14 14:57:39 UTC

HMDB ID

HMDB0060842

Secondary Accession Numbers

HMDB60842

Metabolite Identification

Common Name

N-Despyridinyl rosiglitazone

Description

N-Despyridinyl rosiglitazone is a metabolite of rosiglitazone. Rosiglitazone is an antidiabetic drug in the thiazolidinedione class of drugs. It works as an insulin sensitizer, by binding to the PPAR receptors in fat cells and making the cells more responsive to insulin. It is marketed by the pharmaceutical company GlaxoSmithKline (GSK) as a stand-alone drug (Avandia) and in combination with metformin (Avandamet) or with glimepiride (Avandaryl). Annual sales peaked at approximately $2.5bn in 2006, but declined after reports of adverse effects. (Wikipedia)

Structure

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

HMDB0060842
     RDKit          3D
N-Despyridinyl rosiglitazone
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.6260    0.4053    1.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4314   -0.9429    0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6059   -0.8843   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -0.4439    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658   -0.3608   -1.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.0380   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5824    0.3433    0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.7234    0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    0.8208   -0.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    1.2589   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427    0.2410    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936    1.0186    0.5526 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5723   -0.3212   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8145   -0.3725   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6409   -1.2820   -0.5365 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3361   -0.7651   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983   -1.1543   -1.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540    0.5176   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1690    0.1291   -1.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8173    0.7498    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7880    1.0813    0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5660    0.4073    1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8574   -1.4365    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1145   -0.1635   -1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5326   -1.8989   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2076    0.5263    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8243   -1.2243    0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785    0.2669    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582    0.9606    1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8987    2.0214    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3474    1.7916   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988   -0.2135    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -2.2977   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7642    0.5753   -2.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -0.1145   -2.8783 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
 19  6  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 15 33  1  0
 18 34  1  0
 19 35  1  0
M  END

  Mrv0541 07041312022D          

 19 20  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3832   -5.4349    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -6.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6132   -6.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -6.2195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -5.1800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060842

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O3S/c1-14-6-7-18-10-4-2-9(3-5-10)8-11-12(16)15-13(17)19-11/h2-5,11,14H,6-8H2,1H3,(H,15,16,17)

> <INCHI_KEY>
BPSKNLFJDYBECE-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O3S

> <MOLECULAR_WEIGHT>
280.343

> <EXACT_MASS>
280.088163078

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.36030751152397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
-0.6118850976644635

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.059961366926576

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.613021468873241

> <JCHEM_PKA_STRONGEST_BASIC>
9.515652915454197

> <JCHEM_POLAR_SURFACE_AREA>
67.43

> <JCHEM_REFRACTIVITY>
73.8401

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060842
     RDKit          3D
N-Despyridinyl rosiglitazone
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.6260    0.4053    1.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4314   -0.9429    0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6059   -0.8843   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -0.4439    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658   -0.3608   -1.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.0380   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5824    0.3433    0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.7234    0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    0.8208   -0.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    1.2589   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427    0.2410    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936    1.0186    0.5526 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5723   -0.3212   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8145   -0.3725   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6409   -1.2820   -0.5365 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3361   -0.7651   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983   -1.1543   -1.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540    0.5176   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1690    0.1291   -1.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8173    0.7498    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7880    1.0813    0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5660    0.4073    1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8574   -1.4365    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1145   -0.1635   -1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5326   -1.8989   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2076    0.5263    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8243   -1.2243    0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785    0.2669    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582    0.9606    1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8987    2.0214    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3474    1.7916   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988   -0.2135    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -2.2977   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7642    0.5753   -2.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -0.1145   -2.8783 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
 19  6  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 15 33  1  0
 18 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      11.915 -10.145   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      11.439 -11.610   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.345 -12.856   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       9.899 -11.610   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.423 -10.145   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.959  -9.669   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18    9   19                                                       
CONECT   19   18    6                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0060842
HETATM    1  C1  UNL     1      -5.626   0.405   1.363  1.00  0.00           C  
HETATM    2  N1  UNL     1      -5.431  -0.943   0.876  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.606  -0.884  -0.332  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.227  -0.444   0.078  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.366  -0.361  -1.027  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.044   0.038  -0.802  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.582   0.343   0.454  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.715   0.723   0.596  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.608   0.821  -0.470  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.963   1.259  -0.191  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.943   0.241   0.257  1.00  0.00           C  
HETATM   12  S1  UNL     1       5.594   1.019   0.553  1.00  0.00           S  
HETATM   13  C10 UNL     1       6.572  -0.321  -0.100  1.00  0.00           C  
HETATM   14  O2  UNL     1       7.815  -0.373  -0.148  1.00  0.00           O  
HETATM   15  N2  UNL     1       5.641  -1.282  -0.536  1.00  0.00           N  
HETATM   16  C11 UNL     1       4.336  -0.765  -0.747  1.00  0.00           C  
HETATM   17  O3  UNL     1       3.598  -1.154  -1.719  1.00  0.00           O  
HETATM   18  C12 UNL     1       1.154   0.518  -1.731  1.00  0.00           C  
HETATM   19  C13 UNL     1      -0.169   0.129  -1.881  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.817   0.750   2.011  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.788   1.081   0.480  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.566   0.407   1.980  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.857  -1.437   1.602  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.115  -0.164  -1.003  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.533  -1.899  -0.745  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.208   0.526   0.601  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.824  -1.224   0.755  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.278   0.267   1.284  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.058   0.961   1.603  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.899   2.021   0.645  1.00  0.00           H  
HETATM   31  H12 UNL     1       3.347   1.792  -1.103  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.699  -0.214   1.242  1.00  0.00           H  
HETATM   33  H14 UNL     1       5.873  -2.298  -0.698  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.764   0.575  -2.616  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.540  -0.115  -2.878  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8   28
CONECT    8    9    9   29
CONECT    9   10   18
CONECT   10   11   30   31
CONECT   11   12   16   32
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   33
CONECT   16   17   17
CONECT   18   19   19   34
CONECT   19   35
END

HMDB0060842
     RDKit          3D
N-Despyridinyl rosiglitazone
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.6260    0.4053    1.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4314   -0.9429    0.8760 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6059   -0.8843   -0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2272   -0.4439    0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658   -0.3608   -1.0275 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0444    0.0380   -0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5824    0.3433    0.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7149    0.7234    0.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6078    0.8208   -0.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9633    1.2589   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9427    0.2410    0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5936    1.0186    0.5526 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5723   -0.3212   -0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8145   -0.3725   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6409   -1.2820   -0.5365 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3361   -0.7651   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5983   -1.1543   -1.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540    0.5176   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1690    0.1291   -1.8808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8173    0.7498    2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7880    1.0813    0.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5660    0.4073    1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8574   -1.4365    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1145   -0.1635   -1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5326   -1.8989   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2076    0.5263    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8243   -1.2243    0.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2785    0.2669    1.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582    0.9606    1.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8987    2.0214    0.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3474    1.7916   -1.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6988   -0.2135    1.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8725   -2.2977   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7642    0.5753   -2.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -0.1145   -2.8783 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
 19  6  1  0
 16 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  7 28  1  0
  8 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 15 33  1  0
 18 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆N₂O₃S

Average Molecular Weight

280.343

Monoisotopic Molecular Weight

280.088163078

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1

InChI Identifier

InChI=1S/C13H16N2O3S/c1-14-6-7-18-10-4-2-9(3-5-10)8-11-12(16)15-13(17)19-11/h2-5,11,14H,6-8H2,1H3,(H,15,16,17)

InChI Key

BPSKNLFJDYBECE-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
Dicarboximide
Thiazolidine
Amino acid or derivatives
Carbonic acid derivative
Thiocarbamic acid derivative
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Azacycle
Secondary amine
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060842)

Organ

Kidney (HMDB: HMDB0060842)
Liver (HMDB: HMDB0060842)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060842)

Cellular substructure

Cytoplasm (HMDB: HMDB0060842)

Source

Endogenous

Endogenous (HMDB: HMDB0060842)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Rosiglitazone Metabolism Pathway (PathBank: SMP0000653)

Role

Not Available

Physical Properties

State

Not Available

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

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	1	ALOGPS
logP	-0.61	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.43 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.84 m³·mol⁻¹	ChemAxon
Polarizability	29.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.481	31661259
DarkChem	[M-H]-	160.314	31661259
DeepCCS	[M+H]+	162.573	30932474
DeepCCS	[M-H]-	160.216	30932474
DeepCCS	[M-2H]-	193.101	30932474
DeepCCS	[M+Na]+	168.667	30932474
AllCCS	[M+H]+	163.5	32859911
AllCCS	[M+H-H2O]+	160.1	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	166.7	32859911
AllCCS	[M+Na-2H]-	166.8	32859911
AllCCS	[M+HCOO]-	167.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Despyridinyl rosiglitazone	CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1	3918.7	Standard polar	33892256
N-Despyridinyl rosiglitazone	CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1	2520.3	Standard non polar	33892256
N-Despyridinyl rosiglitazone	CNCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1	2606.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Despyridinyl rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C	2880.1	Semi standard non polar	33892256
N-Despyridinyl rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C	2750.5	Standard non polar	33892256
N-Despyridinyl rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C	3994.3	Standard polar	33892256
N-Despyridinyl rosiglitazone,1TMS,isomer #2	CNCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1	2624.7	Semi standard non polar	33892256
N-Despyridinyl rosiglitazone,1TMS,isomer #2	CNCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1	2597.3	Standard non polar	33892256
N-Despyridinyl rosiglitazone,1TMS,isomer #2	CNCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1	3360.6	Standard polar	33892256
N-Despyridinyl rosiglitazone,2TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C	2764.0	Semi standard non polar	33892256
N-Despyridinyl rosiglitazone,2TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C	2782.8	Standard non polar	33892256
N-Despyridinyl rosiglitazone,2TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C	3266.9	Standard polar	33892256
N-Despyridinyl rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C	3116.9	Semi standard non polar	33892256
N-Despyridinyl rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C	2963.6	Standard non polar	33892256
N-Despyridinyl rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C	4069.7	Standard polar	33892256
N-Despyridinyl rosiglitazone,1TBDMS,isomer #2	CNCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1	2866.0	Semi standard non polar	33892256
N-Despyridinyl rosiglitazone,1TBDMS,isomer #2	CNCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1	2840.1	Standard non polar	33892256
N-Despyridinyl rosiglitazone,1TBDMS,isomer #2	CNCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1	3374.6	Standard polar	33892256
N-Despyridinyl rosiglitazone,2TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C	3235.1	Semi standard non polar	33892256
N-Despyridinyl rosiglitazone,2TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C	3207.6	Standard non polar	33892256
N-Despyridinyl rosiglitazone,2TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C	3360.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Despyridinyl rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9220000000-6e2d7ccd05e832f79fce	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Despyridinyl 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 10V, Positive-QTOF	splash10-001i-2090000000-f931388e701a141be7df	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 20V, Positive-QTOF	splash10-0a4i-6290000000-f11953d18174bade7612	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 40V, Positive-QTOF	splash10-0a4l-9510000000-e93d6b2155c0925265b9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 10V, Negative-QTOF	splash10-004i-0090000000-fe614566709896cd02b1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 20V, Negative-QTOF	splash10-0pbc-4490000000-c24c58bc85670a1c68c5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 40V, Negative-QTOF	splash10-0006-9300000000-1b67ba3bfb5252681e8a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 10V, Positive-QTOF	splash10-001i-0090000000-5dbb100e8a21d2a73f35	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 20V, Positive-QTOF	splash10-0m60-2690000000-a445f260ff309957615f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 40V, Positive-QTOF	splash10-0a6u-4900000000-02d090888a7dd4c34bc4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 10V, Negative-QTOF	splash10-004i-0090000000-327b05f2638442160201	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 20V, Negative-QTOF	splash10-056u-4090000000-cf1dbd5fe1229aac768a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Despyridinyl rosiglitazone 40V, Negative-QTOF	splash10-014l-4900000000-f5f9ef705b0dbb60792d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Rosiglitazone Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10356320

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-Despyridinyl rosiglitazone (HMDB0060842)

MOL for HMDB0060842 (N-Despyridinyl rosiglitazone)

3D MOL for HMDB0060842 (N-Despyridinyl rosiglitazone)

3D SDF for HMDB0060842 (N-Despyridinyl rosiglitazone)

3D-SDF for HMDB0060842 (N-Despyridinyl rosiglitazone)

PDB for HMDB0060842 (N-Despyridinyl rosiglitazone)

3D PDB for HMDB0060842 (N-Despyridinyl rosiglitazone)

SMILES for HMDB0060842 (N-Despyridinyl rosiglitazone)

INCHI for HMDB0060842 (N-Despyridinyl rosiglitazone)

Structure for HMDB0060842 (N-Despyridinyl rosiglitazone)

3D Structure for HMDB0060842 (N-Despyridinyl rosiglitazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra