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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:10:43 UTC

Update Date

2021-09-14 15:47:33 UTC

HMDB ID

HMDB0060980

Secondary Accession Numbers

HMDB60980

Metabolite Identification

Common Name

N-desmethylrosiglitazone

Description

N-desmethylrosiglitazone 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

HMDB0060980
     RDKit          3D
N-desmethylrosiglitazone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -7.6580   -1.6429   -1.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7838   -1.2443   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7777   -1.2139    1.1536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250   -0.9873    1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6137   -0.9344    3.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4887   -0.7536    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    0.4883    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462    0.6523    0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    0.1040    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.2811    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501    0.9967   -0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587    1.2473   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801    0.8921   -1.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -0.5849   -1.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139   -0.7818   -2.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763   -0.5884   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0136   -0.0554    1.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3784   -0.1935    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8596   -0.5239   -0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121   -0.7104   -1.0639 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4936    1.5428   -1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    1.3797   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1876   -0.5543   -0.6696 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1724   -0.2957    3.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388   -1.6437    0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4674    1.3366    1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7335   -0.1501    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.4076   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4961    1.3170   -2.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705   -0.9608   -2.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -1.1953   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346   -1.0924   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190   -0.1552    0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    0.2026    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0574   -0.0378    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9463   -0.6248   -0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087    2.1215   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5790    1.7995   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  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
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 19 20  1  0
 20 21  2  0
 11 22  1  0
 22 23  2  0
  6 24  1  0
 24  2  1  0
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  5 25  1  0
  6 26  1  0
  7 27  1  0
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 13 31  1  0
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 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
M  END


  Mrv0541 07091309102D          

 24 26  0  0  0  0            999 V2000
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    3.3320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7376    2.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119    3.9995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    2.5474    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
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  6  4  1  0  0  0  0
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  8  2  1  0  0  0  0
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 13  6  2  0  0  0  0
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 15  3  2  0  0  0  0
 16 14  1  0  0  0  0
 18  8  2  0  0  0  0
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 23 10  1  0  0  0  0
 23 13  1  0  0  0  0
 24 14  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060980

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17N3O3S/c21-16-14(24-17(22)20-16)11-12-4-6-13(7-5-12)23-10-9-19-15-3-1-2-8-18-15/h1-8,14H,9-11H2,(H,18,19)(H,20,21,22)

> <INCHI_KEY>
ZJQTVMXUIGXRMR-UHFFFAOYSA-N

> <FORMULA>
C17H17N3O3S

> <MOLECULAR_WEIGHT>
343.4

> <EXACT_MASS>
343.099062115

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
35.979896275576564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-5-[(4-{2-[(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
1.8264469526105638

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.661160128966884

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.810699561234307

> <JCHEM_PKA_STRONGEST_BASIC>
6.69171904156243

> <JCHEM_POLAR_SURFACE_AREA>
83.81000000000002

> <JCHEM_REFRACTIVITY>
93.8768

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-5-({4-[2-(pyridin-2-ylamino)ethoxy]phenyl}methyl)-5H-1,3-thiazol-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060980
     RDKit          3D
N-desmethylrosiglitazone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -7.6580   -1.6429   -1.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7838   -1.2443   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7777   -1.2139    1.1536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250   -0.9873    1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6137   -0.9344    3.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4887   -0.7536    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    0.4883    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462    0.6523    0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    0.1040    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.2811    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501    0.9967   -0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587    1.2473   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801    0.8921   -1.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -0.5849   -1.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139   -0.7818   -2.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763   -0.5884   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677   -0.2598    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0136   -0.0554    1.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3784   -0.1935    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8596   -0.5239   -0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121   -0.7104   -1.0639 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4936    1.5428   -1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    1.3797   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1876   -0.5543   -0.6696 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1724   -0.2957    3.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388   -1.6437    0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4674    1.3366    1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836    0.3406    2.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2384   -0.4715    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335   -0.1501    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.4076   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4961    1.3170   -2.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705   -0.9608   -2.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -1.1953   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346   -1.0924   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190   -0.1552    0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    0.2026    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0574   -0.0378    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9463   -0.6248   -0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087    2.1215   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5790    1.7995   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  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
 20 21  2  0
 11 22  1  0
 22 23  2  0
  6 24  1  0
 24  2  1  0
 23  8  1  0
 21 16  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.088   4.755   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.104   6.220   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      10.669   0.000   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       8.002   0.000   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -0.564   6.220   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       1.377   4.279   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.009   7.466   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0      -2.580   4.755   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    8                                                       
CONECT    3    1   15                                                       
CONECT    4    6   12                                                       
CONECT    5    7   12                                                       
CONECT    6    4   13                                                       
CONECT    7    5   13                                                       
CONECT    8    2   18                                                       
CONECT    9   10   19                                                       
CONECT   10    9   23                                                       
CONECT   11   12   14                                                       
CONECT   12    4    5   11                                                  
CONECT   13    6    7   23                                                  
CONECT   14   11   16   24                                                  
CONECT   15    3   18   19                                                  
CONECT   16   14   20   21                                                  
CONECT   17   20   22   24                                                  
CONECT   18    8   15                                                       
CONECT   19    9   15                                                       
CONECT   20   16   17                                                       
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   10   13                                                       
CONECT   24   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0060980
HETATM    1  O1  UNL     1      -7.658  -1.643  -1.034  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.784  -1.244  -0.238  1.00  0.00           C  
HETATM    3  N1  UNL     1      -6.778  -1.214   1.154  1.00  0.00           N  
HETATM    4  C2  UNL     1      -5.725  -0.987   1.777  1.00  0.00           C  
HETATM    5  O2  UNL     1      -5.614  -0.934   3.210  1.00  0.00           O  
HETATM    6  C3  UNL     1      -4.489  -0.754   0.997  1.00  0.00           C  
HETATM    7  C4  UNL     1      -3.770   0.488   1.453  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.546   0.652   0.625  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.333   0.104   0.979  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.202   0.281   0.172  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.250   0.997  -0.989  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.759   1.247  -1.866  1.00  0.00           O  
HETATM   13  C9  UNL     1       2.080   0.892  -1.910  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.381  -0.585  -1.998  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.814  -0.782  -2.033  1.00  0.00           N  
HETATM   16  C11 UNL     1       4.676  -0.588  -0.921  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.168  -0.260   0.309  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.014  -0.055   1.387  1.00  0.00           C  
HETATM   19  C14 UNL     1       6.378  -0.193   1.184  1.00  0.00           C  
HETATM   20  C15 UNL     1       6.860  -0.524  -0.058  1.00  0.00           C  
HETATM   21  N3  UNL     1       6.012  -0.710  -1.064  1.00  0.00           N  
HETATM   22  C16 UNL     1      -1.494   1.543  -1.325  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.612   1.380  -0.547  1.00  0.00           C  
HETATM   24  S1  UNL     1      -5.188  -0.554  -0.670  1.00  0.00           S  
HETATM   25  H1  UNL     1      -6.172  -0.296   3.738  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.839  -1.644   0.964  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.467   1.337   1.342  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.484   0.341   2.505  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.238  -0.471   1.887  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.733  -0.150   0.480  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.631   1.408  -1.117  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.496   1.317  -2.881  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.970  -0.961  -2.983  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.895  -1.195  -1.232  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.235  -1.092  -2.967  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.119  -0.155   0.518  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.606   0.203   2.348  1.00  0.00           H  
HETATM   38  H14 UNL     1       7.057  -0.038   2.014  1.00  0.00           H  
HETATM   39  H15 UNL     1       7.946  -0.625  -0.182  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.609   2.122  -2.229  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.579   1.800  -0.800  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4    4
CONECT    4    5    6
CONECT    5   25
CONECT    6    7   24   26
CONECT    7    8   27   28
CONECT    8    9    9   23
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12   22
CONECT   12   13
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   35
CONECT   16   17   17   21
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   20   38
CONECT   20   21   21   39
CONECT   22   23   23   40
CONECT   23   41
END

HMDB0060980
     RDKit          3D
N-desmethylrosiglitazone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -7.6580   -1.6429   -1.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7838   -1.2443   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7777   -1.2139    1.1536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7250   -0.9873    1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6137   -0.9344    3.2104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4887   -0.7536    0.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7703    0.4883    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5462    0.6523    0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3327    0.1040    0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    0.2811    0.1725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501    0.9967   -0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7587    1.2473   -1.8662 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801    0.8921   -1.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -0.5849   -1.9979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139   -0.7818   -2.0333 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763   -0.5884   -0.9206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1677   -0.2598    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0136   -0.0554    1.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3784   -0.1935    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8596   -0.5239   -0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121   -0.7104   -1.0639 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4936    1.5428   -1.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    1.3797   -0.5468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1876   -0.5543   -0.6696 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1724   -0.2957    3.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8388   -1.6437    0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4674    1.3366    1.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4836    0.3406    2.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2384   -0.4715    1.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335   -0.1501    0.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6308    1.4076   -1.1174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4961    1.3170   -2.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705   -0.9608   -2.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -1.1953   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346   -1.0924   -2.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1190   -0.1552    0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059    0.2026    2.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0574   -0.0378    2.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9463   -0.6248   -0.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6087    2.1215   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5790    1.7995   -0.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  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
 20 21  2  0
 11 22  1  0
 22 23  2  0
  6 24  1  0
 24  2  1  0
 23  8  1  0
 21 16  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇N₃O₃S

Average Molecular Weight

343.4

Monoisotopic Molecular Weight

343.099062115

IUPAC Name

4-hydroxy-5-[(4-{2-[(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one

Traditional Name

4-hydroxy-5-({4-[2-(pyridin-2-ylamino)ethoxy]phenyl}methyl)-5H-1,3-thiazol-2-one

CAS Registry Number

Not Available

SMILES

OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1

InChI Identifier

InChI=1S/C17H17N3O3S/c21-16-14(24-17(22)20-16)11-12-4-6-13(7-5-12)23-10-9-19-15-3-1-2-8-18-15/h1-8,14H,9-11H2,(H,18,19)(H,20,21,22)

InChI Key

ZJQTVMXUIGXRMR-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
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

Not Available

Kidney (HMDB: HMDB0060980)
Liver (HMDB: HMDB0060980)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060980)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060980)

Cellular substructure

Cytoplasm (HMDB: HMDB0060980)

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	0.063 g/L	ALOGPS
logP	2.54	ALOGPS
logP	1.83	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.81	ChemAxon
pKa (Strongest Basic)	6.69	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.81 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	93.88 m³·mol⁻¹	ChemAxon
Polarizability	35.98 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]+	179.925	31661259
DarkChem	[M-H]-	174.62	31661259
DeepCCS	[M+H]+	173.462	30932474
DeepCCS	[M-H]-	171.104	30932474
DeepCCS	[M-2H]-	204.352	30932474
DeepCCS	[M+Na]+	179.579	30932474
AllCCS	[M+H]+	180.8	32859911
AllCCS	[M+H-H2O]+	177.8	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.4	32859911
AllCCS	[M-H]-	180.2	32859911
AllCCS	[M+Na-2H]-	179.9	32859911
AllCCS	[M+HCOO]-	179.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-desmethylrosiglitazone	OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1	4619.2	Standard polar	33892256
N-desmethylrosiglitazone	OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1	3342.3	Standard non polar	33892256
N-desmethylrosiglitazone	OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1	3339.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-desmethylrosiglitazone,1TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1	3397.2	Semi standard non polar	33892256
N-desmethylrosiglitazone,1TMS,isomer #2	C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=CC=CC=N1	3363.8	Semi standard non polar	33892256
N-desmethylrosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCN(C2=CC=CC=N2)[Si](C)(C)C)C=C1	3282.9	Semi standard non polar	33892256
N-desmethylrosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCN(C2=CC=CC=N2)[Si](C)(C)C)C=C1	2913.8	Standard non polar	33892256
N-desmethylrosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCN(C2=CC=CC=N2)[Si](C)(C)C)C=C1	4388.9	Standard polar	33892256
N-desmethylrosiglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCNC2=CC=CC=N2)C=C1	3614.1	Semi standard non polar	33892256
N-desmethylrosiglitazone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=CC=CC=N1	3561.9	Semi standard non polar	33892256
N-desmethylrosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCN(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C1	3630.8	Semi standard non polar	33892256
N-desmethylrosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCN(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C1	3285.6	Standard non polar	33892256
N-desmethylrosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=O)SC1CC1=CC=C(OCCN(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)C=C1	4386.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylrosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pi3-1791000000-07ab51c5d42d874d9852	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylrosiglitazone GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-4971000000-65b7234d175f0fa7dee9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-desmethylrosiglitazone 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-desmethylrosiglitazone 10V, Positive-QTOF	splash10-0006-0119000000-dd81a8fb0ec153436c1b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 20V, Positive-QTOF	splash10-00di-3794000000-7edee17397c59657c070	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 40V, Positive-QTOF	splash10-052b-8910000000-9269d4bb099ff379b52b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 10V, Negative-QTOF	splash10-0006-4049000000-84f9260585fc77213cb7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 20V, Negative-QTOF	splash10-0006-9020000000-b4ffa143ed68e16828a1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 40V, Negative-QTOF	splash10-0f6x-9810000000-1a869ba8f5d55e57c337	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 10V, Positive-QTOF	splash10-006x-0409000000-08634057a2aeca5080a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 20V, Positive-QTOF	splash10-00di-5497000000-c2cf9ec30ae59dffd020	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 40V, Positive-QTOF	splash10-009t-9600000000-36eb6685e7b0f70727cb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 10V, Negative-QTOF	splash10-0006-0049000000-c613e8d90e2f555e8d5a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 20V, Negative-QTOF	splash10-006x-8393000000-f70561c45cc5f70927e7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-desmethylrosiglitazone 40V, Negative-QTOF	splash10-0006-9300000000-c6eaceb4786905aa0efd	2021-09-25	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

12000328

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-desmethylrosiglitazone (HMDB0060980)

MOL for HMDB0060980 (N-desmethylrosiglitazone)

3D MOL for HMDB0060980 (N-desmethylrosiglitazone)

3D SDF for HMDB0060980 (N-desmethylrosiglitazone)

3D-SDF for HMDB0060980 (N-desmethylrosiglitazone)

PDB for HMDB0060980 (N-desmethylrosiglitazone)

3D PDB for HMDB0060980 (N-desmethylrosiglitazone)

SMILES for HMDB0060980 (N-desmethylrosiglitazone)

INCHI for HMDB0060980 (N-desmethylrosiglitazone)

Structure for HMDB0060980 (N-desmethylrosiglitazone)

3D Structure for HMDB0060980 (N-desmethylrosiglitazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra