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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:02:44 UTC

Update Date

2021-09-14 14:59:06 UTC

HMDB ID

HMDB0060838

Secondary Accession Numbers

HMDB60838

Metabolite Identification

Common Name

N-Desmethyl-p-hydroxyrosiglitazone

Description

N-Desmethyl-p-hydroxyrosiglitazone 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

HMDB0060838
     RDKit          3D
N-Desmethyl-p-hydroxyrosiglitazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    6.2601   -0.4235   -4.1440 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1090   -0.6046   -2.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9979   -1.1275   -1.9559 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3758   -1.6019   -0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7697   -2.6273   -0.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2009   -0.8205   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1122   -1.6887    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780   -0.8016    0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073   -0.2487    1.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859    0.5679    2.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264    0.8942    1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    1.7156    1.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173    2.2073    1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3215    1.1366    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455    1.6837    0.4499 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    0.8642    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8430    0.6371   -0.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8400   -1.5515   -0.9920 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5786   -0.4628    0.2482 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9073    0.3392    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -0.4959   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8692    0.9810    3.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.8149    0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    2.9492    2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516    0.6315    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    0.3769    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5847    2.7196    0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8231    2.5052   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7292    1.0768   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8968   -1.9360   -1.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5851   -2.3344    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185    0.5816   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -0.8989   -1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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M  END

  Mrv0541 07041312022D          

 25 27  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3832   -5.4349    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -3.7125    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
  1  2  1  0  0  0  0
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  5 24  1  0  0  0  0
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  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060838

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17N3O4S/c21-12-3-6-15(19-10-12)18-7-8-24-13-4-1-11(2-5-13)9-14-16(22)20-17(23)25-14/h1-6,10,14,21H,7-9H2,(H,18,19)(H,20,22,23)

> <INCHI_KEY>
SVUUNTJZVPNZSL-UHFFFAOYSA-N

> <FORMULA>
C17H17N3O4S

> <MOLECULAR_WEIGHT>
359.4

> <EXACT_MASS>
359.093976737

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
37.07864972041575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
1.521159489910672

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.11350144947642

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.816664993798958

> <JCHEM_PKA_STRONGEST_BASIC>
6.186106783747007

> <JCHEM_POLAR_SURFACE_AREA>
100.55

> <JCHEM_REFRACTIVITY>
95.536

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060838
     RDKit          3D
N-Desmethyl-p-hydroxyrosiglitazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    6.2601   -0.4235   -4.1440 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1090   -0.6046   -2.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9979   -1.1275   -1.9559 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3758   -1.6019   -0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7697   -2.6273   -0.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2009   -0.8205   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1122   -1.6887    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780   -0.8016    0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073   -0.2487    1.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859    0.5679    2.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264    0.8942    1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    1.7156    1.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173    2.2073    1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3215    1.1366    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455    1.6837    0.4499 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    0.8642    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7700    1.4470   -0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8430    0.6371   -0.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7628   -0.7266   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8400   -1.5515   -0.9920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6147   -1.2670   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5786   -0.4628    0.2482 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9073    0.3392    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -0.4959   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193   -0.2217   -2.0125 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -1.1447   -2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4353    0.0293    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4877   -2.2581    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7417   -0.5131    2.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8692    0.9810    3.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.8149    0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    2.9492    2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5847    2.7196    0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8231    2.5052   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7292    1.0768   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8968   -1.9360   -1.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5851   -2.3344    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185    0.5816   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -0.8989   -1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
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 11 23  1  0
 23 24  2  0
  6 25  1  0
 25  2  1  0
 24  8  1  0
 22 16  1  0
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 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
 24 42  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  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   16  S   UNK     0      11.915 -10.145   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0      11.439 -11.610   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.345 -12.856   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       9.899 -11.610   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       9.423 -10.145   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.959  -9.669   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   13   23                                                       
CONECT   23   22   10                                                       
CONECT   24    5   25                                                       
CONECT   25   24    2                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0060838
HETATM    1  O1  UNL     1       6.260  -0.423  -4.144  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.109  -0.605  -2.923  1.00  0.00           C  
HETATM    3  N1  UNL     1       6.998  -1.127  -1.956  1.00  0.00           N  
HETATM    4  C2  UNL     1       6.376  -1.602  -0.799  1.00  0.00           C  
HETATM    5  O2  UNL     1       6.770  -2.627  -0.142  1.00  0.00           O  
HETATM    6  C3  UNL     1       5.201  -0.820  -0.371  1.00  0.00           C  
HETATM    7  C4  UNL     1       4.112  -1.689   0.214  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.978  -0.802   0.612  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.907  -0.249   1.873  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.886   0.568   2.276  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.826   0.894   1.400  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.169   1.716   1.847  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.317   2.207   1.320  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.322   1.137   1.017  1.00  0.00           C  
HETATM   15  N2  UNL     1      -3.545   1.684   0.450  1.00  0.00           N  
HETATM   16  C11 UNL     1      -4.640   0.864   0.082  1.00  0.00           C  
HETATM   17  C12 UNL     1      -5.770   1.447  -0.450  1.00  0.00           C  
HETATM   18  C13 UNL     1      -6.843   0.637  -0.810  1.00  0.00           C  
HETATM   19  C14 UNL     1      -6.763  -0.727  -0.632  1.00  0.00           C  
HETATM   20  O4  UNL     1      -7.840  -1.552  -0.992  1.00  0.00           O  
HETATM   21  C15 UNL     1      -5.615  -1.267  -0.097  1.00  0.00           C  
HETATM   22  N3  UNL     1      -4.579  -0.463   0.248  1.00  0.00           N  
HETATM   23  C16 UNL     1       0.907   0.339   0.146  1.00  0.00           C  
HETATM   24  C17 UNL     1       1.957  -0.496  -0.256  1.00  0.00           C  
HETATM   25  S1  UNL     1       4.619  -0.222  -2.012  1.00  0.00           S  
HETATM   26  H1  UNL     1       8.050  -1.145  -2.125  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.435   0.029   0.281  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.488  -2.258   1.074  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.788  -2.404  -0.592  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.742  -0.513   2.544  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.869   0.981   3.275  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.127   2.815   0.395  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.740   2.949   2.074  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.552   0.632   1.994  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.906   0.377   0.374  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.585   2.720   0.324  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.823   2.505  -0.584  1.00  0.00           H  
HETATM   38  H13 UNL     1      -7.729   1.077  -1.225  1.00  0.00           H  
HETATM   39  H14 UNL     1      -7.897  -1.936  -1.926  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.585  -2.334   0.028  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.119   0.582  -0.580  1.00  0.00           H  
HETATM   42  H17 UNL     1       1.949  -0.899  -1.269  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   25
CONECT    3    4   26
CONECT    4    5    5    6
CONECT    6    7   25   27
CONECT    7    8   28   29
CONECT    8    9    9   24
CONECT    9   10   30
CONECT   10   11   11   31
CONECT   11   12   23
CONECT   12   13
CONECT   13   14   32   33
CONECT   14   15   34   35
CONECT   15   16   36
CONECT   16   17   17   22
CONECT   17   18   37
CONECT   18   19   19   38
CONECT   19   20   21
CONECT   20   39
CONECT   21   22   22   40
CONECT   23   24   24   41
CONECT   24   42
END

HMDB0060838
     RDKit          3D
N-Desmethyl-p-hydroxyrosiglitazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    6.2601   -0.4235   -4.1440 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1090   -0.6046   -2.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9979   -1.1275   -1.9559 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3758   -1.6019   -0.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7697   -2.6273   -0.1421 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2009   -0.8205   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1122   -1.6887    0.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9780   -0.8016    0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9073   -0.2487    1.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859    0.5679    2.2755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264    0.8942    1.3995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    1.7156    1.8472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3173    2.2073    1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3215    1.1366    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455    1.6837    0.4499 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6401    0.8642    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7700    1.4470   -0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8430    0.6371   -0.8097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7628   -0.7266   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8400   -1.5515   -0.9920 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6147   -1.2670   -0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5786   -0.4628    0.2482 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9073    0.3392    0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9567   -0.4959   -0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193   -0.2217   -2.0125 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -1.1447   -2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4353    0.0293    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4877   -2.2581    1.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7884   -2.4040   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -0.5131    2.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8692    0.9810    3.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.8149    0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    2.9492    2.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5516    0.6315    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9062    0.3769    0.3739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5847    2.7196    0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8231    2.5052   -0.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7292    1.0768   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8968   -1.9360   -1.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5851   -2.3344    0.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185    0.5816   -0.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -0.8989   -1.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 11 23  1  0
 23 24  2  0
  6 25  1  0
 25  2  1  0
 24  8  1  0
 22 16  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 10 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
 24 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇N₃O₄S

Average Molecular Weight

359.4

Monoisotopic Molecular Weight

359.093976737

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1

InChI Identifier

InChI=1S/C17H17N3O4S/c21-12-3-6-15(19-10-12)18-7-8-24-13-4-1-11(2-5-13)9-14-16(22)20-17(23)25-14/h1-6,10,14,21H,7-9H2,(H,18,19)(H,20,22,23)

InChI Key

SVUUNTJZVPNZSL-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
Aminopyridine
Hydroxypyridine
Thiazolidinedione
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Imidolactam
Pyridine
Dicarboximide
Heteroaromatic compound
Thiazolidine
Amino acid or derivatives
Carbonic acid derivative
Thiocarbamic acid derivative
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
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: HMDB0060838)

Organ

Kidney (HMDB: HMDB0060838)
Liver (HMDB: HMDB0060838)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060838)

Cellular substructure

Cytoplasm (HMDB: HMDB0060838)

Source

Endogenous

Endogenous (HMDB: HMDB0060838)

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	0.062 g/L	ALOGPS
logP	2.31	ALOGPS
logP	1.52	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.82	ChemAxon
pKa (Strongest Basic)	6.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.55 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	95.54 m³·mol⁻¹	ChemAxon
Polarizability	37.08 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
DeepCCS	[M+H]+	181.531	30932474
DeepCCS	[M-H]-	178.988	30932474
DeepCCS	[M-2H]-	213.03	30932474
DeepCCS	[M+Na]+	189.151	30932474
AllCCS	[M+H]+	183.5	32859911
AllCCS	[M+H-H2O]+	180.7	32859911
AllCCS	[M+NH4]+	186.2	32859911
AllCCS	[M+Na]+	186.9	32859911
AllCCS	[M-H]-	182.3	32859911
AllCCS	[M+Na-2H]-	182.1	32859911
AllCCS	[M+HCOO]-	182.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl-p-hydroxyrosiglitazone	OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	4961.8	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone	OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	3560.9	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone	OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	3606.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl-p-hydroxyrosiglitazone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	3780.3	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,1TMS,isomer #2	C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(O)C=N1	3725.8	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,1TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(O)C=N3)C=C2)C1=O	3674.7	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C)N=C1	3727.9	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C)N=C1	3418.2	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C)N=C1	4813.3	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	3644.2	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	3375.5	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	4478.8	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(O)C=N3)[Si](C)(C)C)C=C2)C1=O	3563.9	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(O)C=N3)[Si](C)(C)C)C=C2)C1=O	3396.6	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(O)C=N3)[Si](C)(C)C)C=C2)C1=O	4399.9	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)[Si](C)(C)C)N=C1	3557.4	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)[Si](C)(C)C)N=C1	3376.6	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)[Si](C)(C)C)N=C1	4065.8	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	4047.8	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(O)C=N1	3988.3	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(O)C=N3)C=C2)C1=O	3924.7	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	4202.6	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	3774.6	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	4810.2	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	4088.8	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	3796.2	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	4486.0	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(O)C=N3)[Si](C)(C)C(C)(C)C)C=C2)C1=O	4047.0	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(O)C=N3)[Si](C)(C)C(C)(C)C)C=C2)C1=O	3790.4	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(O)C=N3)[Si](C)(C)C(C)(C)C)C=C2)C1=O	4384.1	Standard polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	4211.0	Semi standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	3941.6	Standard non polar	33892256
N-Desmethyl-p-hydroxyrosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	4174.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2951000000-7c06e9483705d77725d5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-3956100000-9ffbdd30587114d4f13b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 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-Desmethyl-p-hydroxyrosiglitazone 10V, Positive-QTOF	splash10-03di-0219000000-232f2852ada45bf26a16	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 20V, Positive-QTOF	splash10-000i-0984000000-2eb76e93e5327206ef01	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 40V, Positive-QTOF	splash10-06ri-2910000000-41c8805f2656eb3d40d9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 10V, Negative-QTOF	splash10-0a4i-0539000000-ca492936b3778758b77f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 20V, Negative-QTOF	splash10-0k9f-5792000000-7d5d345de442d371a368	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 40V, Negative-QTOF	splash10-0006-9300000000-9052930d07dcef8b24f9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 10V, Positive-QTOF	splash10-03di-0329000000-67155888cf23101badc8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 20V, Positive-QTOF	splash10-03el-1978000000-2ead8e1cba4f4ac67a16	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 40V, Positive-QTOF	splash10-00yi-2901000000-d04019d52450a3707224	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 10V, Negative-QTOF	splash10-0a4i-0029000000-84de2ae783da5b28fed8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 20V, Negative-QTOF	splash10-0006-9243000000-8b9c8e4259539c956687	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-hydroxyrosiglitazone 40V, Negative-QTOF	splash10-0006-9100000000-c5cc48bb6bdfa1b80dd5	2021-10-12	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

131769972

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-Desmethyl-p-hydroxyrosiglitazone (HMDB0060838)

MOL for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

3D MOL for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

3D SDF for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

3D-SDF for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

PDB for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

3D PDB for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

SMILES for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

INCHI for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

Structure for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

3D Structure for HMDB0060838 (N-Desmethyl-p-hydroxyrosiglitazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra