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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:02:38 UTC

Update Date

2021-09-14 14:58:38 UTC

HMDB ID

HMDB0060836

Secondary Accession Numbers

HMDB60836

Metabolite Identification

Common Name

N-Desmethyl-O-hydroxy rosiglitazone

Description

N-Desmethyl-O-hydroxy 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


  Mrv0541 07041312022D          

 25 27  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -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
   -1.4289   -1.6500    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
  1  2  1  0  0  0  0
  2  3  2  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  1  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
M  END

HMDB0060836
     RDKit          3D
N-Desmethyl-O-hydroxy rosiglitazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    8.1078   -1.5320    1.9351 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2599   -1.0806    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0305   -1.6604    0.7920 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4829   -1.1335   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768   -1.7832   -1.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742    0.3443   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7381    1.0977    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242    0.8529    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174    1.6204   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2650    1.3699   -1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    0.3349   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7045    0.0413   -0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    0.7705   -1.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    0.2195   -1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438    0.2826   -0.1998 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -0.1778    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5945   -0.6978   -0.9857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8510   -1.1479   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4215   -1.0795    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7296   -0.5614    1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -0.1163    1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994    0.4152    2.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -0.4410    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1932    0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3432    0.4614    0.2766 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5154   -2.4298    1.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9763    0.7705    1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776    2.4393   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    1.9939   -1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    0.7699   -2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739    1.8279   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8764   -0.8341   -1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973    0.8093   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942    0.6794    0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4379   -1.5641   -1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4418   -1.4458    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1843   -0.5115    2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0826    0.4809    3.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496   -1.2574    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382   -0.7855    1.4610 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
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 13 14  1  0
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 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
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 21 22  1  0
 11 23  1  0
 23 24  2  0
  6 25  1  0
 25  2  1  0
 24  8  1  0
 21 16  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
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 13 32  1  0
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 15 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 40  1  0
 23 41  1  0
 24 42  1  0
M  END


  Mrv0541 07041312022D          

 25 27  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   -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
   -1.4289   -1.6500    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
  1  2  1  0  0  0  0
  2  3  2  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  1  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
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 13 14  1  0  0  0  0
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 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  2  0  0  0  0
  8 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060836

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
GWVBGLUFILBNNY-UHFFFAOYSA-N

> <FORMULA>
C17H17N3O4S

> <MOLECULAR_WEIGHT>
359.4

> <EXACT_MASS>
359.093976737

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.87403857524232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
1.4089421546370011

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.521444404812431

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.393648011017743

> <JCHEM_PKA_STRONGEST_BASIC>
7.013870513599974

> <JCHEM_POLAR_SURFACE_AREA>
100.55

> <JCHEM_REFRACTIVITY>
95.53600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.74e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060836
     RDKit          3D
N-Desmethyl-O-hydroxy rosiglitazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    8.1078   -1.5320    1.9351 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2599   -1.0806    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0305   -1.6604    0.7920 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4829   -1.1335   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768   -1.7832   -1.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742    0.3443   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7381    1.0977    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242    0.8529    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174    1.6204   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2650    1.3699   -1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    0.3349   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7045    0.0413   -0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    0.7705   -1.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    0.2195   -1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438    0.2826   -0.1998 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -0.1778    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5945   -0.6978   -0.9857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8510   -1.1479   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4215   -1.0795    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7296   -0.5614    1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -0.1163    1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994    0.4152    2.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -0.4410    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1932    0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3432    0.4614    0.2766 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5154   -2.4298    1.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6918    0.6836   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228    2.1676    0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763    0.7705    1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776    2.4393   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    1.9939   -1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    0.7699   -2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739    1.8279   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8764   -0.8341   -1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973    0.8093   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942    0.6794    0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4379   -1.5641   -1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4418   -1.4458    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1843   -0.5115    2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0826    0.4809    3.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496   -1.2574    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382   -0.7855    1.4610 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
 20 21  2  0
 21 22  1  0
 11 23  1  0
 23 24  2  0
  6 25  1  0
 25  2  1  0
 24  8  1  0
 21 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
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 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       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0      11.915 -10.145   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0      11.439 -11.610   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.345 -12.856   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       9.899 -11.610   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       9.423 -10.145   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.959  -9.669   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   11   21                                                       
CONECT   21   20    8                                                       
CONECT   22    3   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    2                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0060836
HETATM    1  O1  UNL     1       8.108  -1.532   1.935  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.260  -1.081   1.163  1.00  0.00           C  
HETATM    3  N1  UNL     1       6.031  -1.660   0.792  1.00  0.00           N  
HETATM    4  C2  UNL     1       5.483  -1.134  -0.394  1.00  0.00           C  
HETATM    5  O2  UNL     1       4.877  -1.783  -1.317  1.00  0.00           O  
HETATM    6  C3  UNL     1       5.674   0.344  -0.504  1.00  0.00           C  
HETATM    7  C4  UNL     1       4.738   1.098   0.398  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.324   0.853   0.117  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.617   1.620  -0.771  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.265   1.370  -1.026  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.626   0.335  -0.379  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.704   0.041  -0.591  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.525   0.770  -1.485  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.928   0.220  -1.506  1.00  0.00           C  
HETATM   15  N2  UNL     1      -3.544   0.283  -0.200  1.00  0.00           N  
HETATM   16  C11 UNL     1      -4.864  -0.178   0.031  1.00  0.00           C  
HETATM   17  N3  UNL     1      -5.595  -0.698  -0.986  1.00  0.00           N  
HETATM   18  C12 UNL     1      -6.851  -1.148  -0.817  1.00  0.00           C  
HETATM   19  C13 UNL     1      -7.421  -1.080   0.436  1.00  0.00           C  
HETATM   20  C14 UNL     1      -6.730  -0.561   1.509  1.00  0.00           C  
HETATM   21  C15 UNL     1      -5.442  -0.116   1.266  1.00  0.00           C  
HETATM   22  O4  UNL     1      -4.699   0.415   2.312  1.00  0.00           O  
HETATM   23  C16 UNL     1       1.330  -0.441   0.515  1.00  0.00           C  
HETATM   24  C17 UNL     1       2.663  -0.193   0.766  1.00  0.00           C  
HETATM   25  S1  UNL     1       7.343   0.461   0.277  1.00  0.00           S  
HETATM   26  H1  UNL     1       5.515  -2.430   1.321  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.692   0.684  -1.535  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.023   2.168   0.346  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.976   0.771   1.447  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.078   2.439  -1.299  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.749   1.994  -1.727  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.068   0.770  -2.487  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.574   1.828  -1.115  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.876  -0.834  -1.880  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.497   0.809  -2.258  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.994   0.679   0.589  1.00  0.00           H  
HETATM   37  H12 UNL     1      -7.438  -1.564  -1.627  1.00  0.00           H  
HETATM   38  H13 UNL     1      -8.442  -1.446   0.569  1.00  0.00           H  
HETATM   39  H14 UNL     1      -7.184  -0.511   2.487  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.083   0.481   3.239  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.850  -1.257   1.034  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.238  -0.786   1.461  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   21
CONECT   17   18
CONECT   18   19   19   37
CONECT   19   20   38
CONECT   20   21   21   39
CONECT   21   22
CONECT   22   40
CONECT   23   24   24   41
CONECT   24   42
END

HMDB0060836
     RDKit          3D
N-Desmethyl-O-hydroxy rosiglitazone
 42 44  0  0  0  0  0  0  0  0999 V2000
    8.1078   -1.5320    1.9351 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2599   -1.0806    1.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0305   -1.6604    0.7920 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4829   -1.1335   -0.3939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768   -1.7832   -1.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6742    0.3443   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7381    1.0977    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3242    0.8529    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6174    1.6204   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2650    1.3699   -1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    0.3349   -0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7045    0.0413   -0.5906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251    0.7705   -1.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9279    0.2195   -1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438    0.2826   -0.1998 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8642   -0.1778    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5945   -0.6978   -0.9857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8510   -1.1479   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4215   -1.0795    0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7296   -0.5614    1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4416   -0.1163    1.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994    0.4152    2.3122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3302   -0.4410    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6631   -0.1932    0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3432    0.4614    0.2766 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5154   -2.4298    1.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6918    0.6836   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0228    2.1676    0.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9763    0.7705    1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776    2.4393   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7490    1.9939   -1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    0.7699   -2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5739    1.8279   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8764   -0.8341   -1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4973    0.8093   -2.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942    0.6794    0.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4379   -1.5641   -1.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4418   -1.4458    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1843   -0.5115    2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0826    0.4809    3.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8496   -1.2574    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2382   -0.7855    1.4610 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
 20 21  2  0
 21 22  1  0
 11 23  1  0
 23 24  2  0
  6 25  1  0
 25  2  1  0
 24  8  1  0
 21 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
 18 37  1  0
 19 38  1  0
 20 39  1  0
 22 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-[(3-hydroxypyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

GWVBGLUFILBNNY-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: HMDB0060836)

Organ

Kidney (HMDB: HMDB0060836)
Liver (HMDB: HMDB0060836)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060836)

Cellular substructure

Cytoplasm (HMDB: HMDB0060836)

Source

Endogenous

Endogenous (HMDB: HMDB0060836)

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	0.067 g/L	ALOGPS
logP	2.33	ALOGPS
logP	1.41	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.39	ChemAxon
pKa (Strongest Basic)	7.01	ChemAxon
Physiological Charge	0	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	36.87 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]+	183.162	31661259
DarkChem	[M-H]-	178.594	31661259
DeepCCS	[M+H]+	182.623	30932474
DeepCCS	[M-H]-	180.156	30932474
DeepCCS	[M-2H]-	214.031	30932474
DeepCCS	[M+Na]+	189.52	30932474
AllCCS	[M+H]+	183.4	32859911
AllCCS	[M+H-H2O]+	180.6	32859911
AllCCS	[M+NH4]+	186.1	32859911
AllCCS	[M+Na]+	186.9	32859911
AllCCS	[M-H]-	182.1	32859911
AllCCS	[M+Na-2H]-	181.9	32859911
AllCCS	[M+HCOO]-	181.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.74 minutes	32390414
Predicted by Siyang on May 30, 2022	14.665 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2441.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	339.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	665.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	808.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1224.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	484.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1670.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	359.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	402.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	126.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	88.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl-O-hydroxy rosiglitazone	OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1	4645.5	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone	OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1	3477.0	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone	OC1=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=CC=C1	3521.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1	3704.5	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #2	C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1O	3605.3	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=NC=CC=C3O)C=C2)C1=O	3528.6	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C	3608.1	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C	3296.2	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C	4755.9	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1	3523.8	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1	3213.7	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1	4442.0	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O	3371.8	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O	3295.4	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C)C=C2)C1=O	4402.1	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C	3407.8	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C	3287.2	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)[Si](C)(C)C	4021.4	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)NC2=O)C=C1	3956.8	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1O	3864.2	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=NC=CC=C3O)C=C2)C1=O	3803.8	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C	4020.9	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C	3649.6	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)[Si](C)(C)C(C)(C)C	4757.9	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1	3960.7	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1	3625.7	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1NCCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1	4458.4	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O	3860.1	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O	3688.0	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=NC=CC=C3O)[Si](C)(C)C(C)(C)C)C=C2)C1=O	4373.8	Standard polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C	4022.2	Semi standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C	3845.8	Standard non polar	33892256
N-Desmethyl-O-hydroxy rosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CN=C1N(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)[Si](C)(C)C(C)(C)C	4135.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1961000000-bdb89099b5ab84dcf743	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (1 TMS) - 70eV, Positive	splash10-00di-2955100000-bde6b78fb75b701962ad	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-O-hydroxy 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-Desmethyl-O-hydroxy rosiglitazone 10V, Positive-QTOF	splash10-03di-0219000000-ab50299314a212f098be	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Positive-QTOF	splash10-000i-0974000000-2a33994dcccc3756ef03	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Positive-QTOF	splash10-01p9-3920000000-113ee2a6bfbed1aca6d5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Negative-QTOF	splash10-0a4i-0549000000-36b7007e3a7548658c8c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Negative-QTOF	splash10-0pbl-4591000000-9fddd5ced0e5ddb88dd5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Negative-QTOF	splash10-0006-9400000000-571bdbdbd29573e6abf8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Negative-QTOF	splash10-05fr-1098000000-7fbb6159e0a3d11a1b95	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Negative-QTOF	splash10-0006-9121000000-cac1b8fa1563e2c426d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Negative-QTOF	splash10-0006-9200000000-2572c44b8781aa19bef1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 10V, Positive-QTOF	splash10-03di-0009000000-82b3876182bcc2781eaf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 20V, Positive-QTOF	splash10-03dr-0977000000-a22398adddc85a82a31e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-O-hydroxy rosiglitazone 40V, Positive-QTOF	splash10-00sa-2900000000-4b8e0a5a07e1cc80c35d	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

86278298

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-O-hydroxy rosiglitazone (HMDB0060836)

MOL for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

3D MOL for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

3D SDF for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

3D-SDF for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

PDB for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

3D PDB for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

SMILES for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

INCHI for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

Structure for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

3D Structure for HMDB0060836 (N-Desmethyl-O-hydroxy rosiglitazone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra