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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:02:47 UTC

Update Date

2021-09-14 14:59:59 UTC

HMDB ID

HMDB0060839

Secondary Accession Numbers

HMDB60839

Metabolite Identification

Common Name

N-Desmethyl-p-O-sulfate rosiglitazone

Description

N-Desmethyl-p-O-sulfate 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          

 29 31  0  0  0  0            999 V2000
   -3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -0.7145   -1.2375    0.0000 C   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 17 26  1  0  0  0  0
 26 27  2  0  0  0  0
 14 27  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
  6 29  1  0  0  0  0
M  END

HMDB0060839
     RDKit          3D
N-Desmethyl-p-O-sulfate rosiglitazone
 46 48  0  0  0  0  0  0  0  0999 V2000
   -6.7981    3.2538    2.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6748    2.2576    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2953    2.0665    0.4266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3913    0.7197    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3707    0.1126   -0.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1481   -0.0537    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386    0.2862   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8490   -0.3919   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214   -1.6144   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042   -2.2614   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4059   -1.6611   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -2.3057   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -1.6701    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452   -2.5446    0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585   -2.0357    1.4705 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9773   -0.9641    1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992   -0.3449   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6213    0.7336   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6107    1.2021    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005    2.2689   -0.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    2.1107   -0.8580 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.8153    0.9459   -1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9692    1.9561    0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1228    3.5390   -1.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490    0.5447    1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9636   -0.4884    1.9053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.4414    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587    0.1929    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7121    0.7635    1.9530 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6641    2.8526   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3275   -1.1147    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6143    0.0767   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0300    1.4081   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4253   -2.0641   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -3.2274   -1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061   -0.6804    0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748   -1.5727    1.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -3.5816    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -2.6513   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533   -2.5342    2.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0397   -0.6885   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723    1.2083   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947    4.3157   -1.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5224    0.8999    2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413    0.0304    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0371    1.1468    0.6607 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  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 19 25  1  0
 25 26  2  0
 11 27  1  0
 27 28  2  0
  6 29  1  0
 29  2  1  0
 28  8  1  0
 26 16  1  0
  3 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 24 43  1  0
 25 44  1  0
 27 45  1  0
 28 46  1  0
M  END


  Mrv0541 07041312022D          

 29 31  0  0  0  0            999 V2000
   -3.5724   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454   -2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -0.7145   -1.2375    0.0000 C   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  2  0  0  0  0
 17 26  1  0  0  0  0
 26 27  2  0  0  0  0
 14 27  1  0  0  0  0
  9 28  1  0  0  0  0
 28 29  2  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060839

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H17N3O7S2/c21-16-14(28-17(22)20-16)9-11-1-3-12(4-2-11)26-8-7-18-15-6-5-13(10-19-15)27-29(23,24)25/h1-6,10,14H,7-9H2,(H,18,19)(H,20,21,22)(H,23,24,25)

> <INCHI_KEY>
ULPCBLHRDLQTTD-UHFFFAOYSA-N

> <FORMULA>
C17H17N3O7S2

> <MOLECULAR_WEIGHT>
439.463

> <EXACT_MASS>
439.050791293

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
42.400791382878786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid

> <ALOGPS_LOGP>
1.08

> <JCHEM_LOGP>
-1.003429568109071

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.623203541155839

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.657933468565859

> <JCHEM_PKA_STRONGEST_BASIC>
4.954047352186834

> <JCHEM_POLAR_SURFACE_AREA>
143.92000000000002

> <JCHEM_REFRACTIVITY>
105.5278

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060839
     RDKit          3D
N-Desmethyl-p-O-sulfate rosiglitazone
 46 48  0  0  0  0  0  0  0  0999 V2000
   -6.7981    3.2538    2.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6748    2.2576    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2953    2.0665    0.4266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3913    0.7197    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3707    0.1126   -0.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1481   -0.0537    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386    0.2862   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8490   -0.3919   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214   -1.6144   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042   -2.2614   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4059   -1.6611   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -2.3057   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -1.6701    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452   -2.5446    0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585   -2.0357    1.4705 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9773   -0.9641    1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992   -0.3449   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6213    0.7336   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6107    1.2021    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005    2.2689   -0.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    2.1107   -0.8580 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.8153    0.9459   -1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9692    1.9561    0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1228    3.5390   -1.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490    0.5447    1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9636   -0.4884    1.9053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.4414    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587    0.1929    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7121    0.7635    1.9530 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6641    2.8526   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3275   -1.1147    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6143    0.0767   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0300    1.4081   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4253   -2.0641   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -3.2274   -1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061   -0.6804    0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748   -1.5727    1.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -3.5816    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -2.6513   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533   -2.5342    2.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0397   -0.6885   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723    1.2083   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947    4.3157   -1.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5224    0.8999    2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413    0.0304    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0371    1.1468    0.6607 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  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 19 25  1  0
 25 26  2  0
 11 27  1  0
 27 28  2  0
  6 29  1  0
 29  2  1  0
 28  8  1  0
 26 16  1  0
  3 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 24 43  1  0
 25 44  1  0
 27 45  1  0
 28 46  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      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0      -5.335  -3.080   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      -4.565  -4.414   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -6.105  -1.746   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   20  S   UNK     0      11.915 -10.145   0.000  0.00  0.00           S+0
HETATM   21  C   UNK     0      11.439 -11.610   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.345 -12.856   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       9.899 -11.610   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       9.423 -10.145   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.959  -9.669   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      -1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   17   27                                                       
CONECT   27   26   14                                                       
CONECT   28    9   29                                                       
CONECT   29   28    6                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

COMPND    HMDB0060839
HETATM    1  O1  UNL     1      -6.798   3.254   2.418  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.675   2.258   1.690  1.00  0.00           C  
HETATM    3  N1  UNL     1      -7.295   2.067   0.427  1.00  0.00           N  
HETATM    4  C2  UNL     1      -7.391   0.720   0.044  1.00  0.00           C  
HETATM    5  O2  UNL     1      -8.371   0.113  -0.516  1.00  0.00           O  
HETATM    6  C3  UNL     1      -6.148  -0.054   0.361  1.00  0.00           C  
HETATM    7  C4  UNL     1      -5.139   0.286  -0.694  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.849  -0.392  -0.534  1.00  0.00           C  
HETATM    9  C6  UNL     1      -3.621  -1.614  -1.119  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.404  -2.261  -0.971  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.406  -1.661  -0.221  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.187  -2.306  -0.071  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.834  -1.670   0.708  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.045  -2.545   0.726  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.158  -2.036   1.470  1.00  0.00           N  
HETATM   16  C11 UNL     1       3.977  -0.964   1.087  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.799  -0.345  -0.124  1.00  0.00           C  
HETATM   18  C13 UNL     1       4.621   0.734  -0.468  1.00  0.00           C  
HETATM   19  C14 UNL     1       5.611   1.202   0.366  1.00  0.00           C  
HETATM   20  O4  UNL     1       6.401   2.269  -0.010  1.00  0.00           O  
HETATM   21  S1  UNL     1       7.859   2.111  -0.858  1.00  0.00           S  
HETATM   22  O5  UNL     1       7.815   0.946  -1.815  1.00  0.00           O  
HETATM   23  O6  UNL     1       8.969   1.956   0.142  1.00  0.00           O  
HETATM   24  O7  UNL     1       8.123   3.539  -1.706  1.00  0.00           O  
HETATM   25  C15 UNL     1       5.749   0.545   1.572  1.00  0.00           C  
HETATM   26  N3  UNL     1       4.964  -0.488   1.905  1.00  0.00           N  
HETATM   27  C16 UNL     1      -1.628  -0.441   0.365  1.00  0.00           C  
HETATM   28  C17 UNL     1      -2.859   0.193   0.204  1.00  0.00           C  
HETATM   29  S2  UNL     1      -5.712   0.763   1.953  1.00  0.00           S  
HETATM   30  H1  UNL     1      -7.664   2.853  -0.195  1.00  0.00           H  
HETATM   31  H2  UNL     1      -6.327  -1.115   0.502  1.00  0.00           H  
HETATM   32  H3  UNL     1      -5.614   0.077  -1.695  1.00  0.00           H  
HETATM   33  H4  UNL     1      -5.030   1.408  -0.682  1.00  0.00           H  
HETATM   34  H5  UNL     1      -4.425  -2.064  -1.704  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.224  -3.227  -1.433  1.00  0.00           H  
HETATM   36  H7  UNL     1       1.006  -0.680   0.268  1.00  0.00           H  
HETATM   37  H8  UNL     1       0.375  -1.573   1.733  1.00  0.00           H  
HETATM   38  H9  UNL     1       1.782  -3.582   1.035  1.00  0.00           H  
HETATM   39  H10 UNL     1       2.374  -2.651  -0.353  1.00  0.00           H  
HETATM   40  H11 UNL     1       3.353  -2.534   2.386  1.00  0.00           H  
HETATM   41  H12 UNL     1       3.040  -0.688  -0.824  1.00  0.00           H  
HETATM   42  H13 UNL     1       4.472   1.208  -1.415  1.00  0.00           H  
HETATM   43  H14 UNL     1       7.795   4.316  -1.220  1.00  0.00           H  
HETATM   44  H15 UNL     1       6.522   0.900   2.240  1.00  0.00           H  
HETATM   45  H16 UNL     1      -0.841   0.030   0.955  1.00  0.00           H  
HETATM   46  H17 UNL     1      -3.037   1.147   0.661  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   29
CONECT    3    4   30
CONECT    4    5    5    6
CONECT    6    7   29   31
CONECT    7    8   32   33
CONECT    8    9    9   28
CONECT    9   10   34
CONECT   10   11   11   35
CONECT   11   12   27
CONECT   12   13
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   40
CONECT   16   17   17   26
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   25
CONECT   20   21
CONECT   21   22   22   23   23
CONECT   21   24
CONECT   24   43
CONECT   25   26   26   44
CONECT   27   28   28   45
CONECT   28   46
END

HMDB0060839
     RDKit          3D
N-Desmethyl-p-O-sulfate rosiglitazone
 46 48  0  0  0  0  0  0  0  0999 V2000
   -6.7981    3.2538    2.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6748    2.2576    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2953    2.0665    0.4266 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3913    0.7197    0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3707    0.1126   -0.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1481   -0.0537    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386    0.2862   -0.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8490   -0.3919   -0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6214   -1.6144   -1.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4042   -2.2614   -0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4059   -1.6611   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -2.3057   -0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8345   -1.6701    0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0452   -2.5446    0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585   -2.0357    1.4705 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9773   -0.9641    1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7992   -0.3449   -0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6213    0.7336   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6107    1.2021    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4005    2.2689   -0.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591    2.1107   -0.8580 S   0  0  0  0  0  6  0  0  0  0  0  0
    7.8153    0.9459   -1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9692    1.9561    0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1228    3.5390   -1.7065 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7490    0.5447    1.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9636   -0.4884    1.9053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6276   -0.4414    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587    0.1929    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7121    0.7635    1.9530 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6641    2.8526   -0.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3275   -1.1147    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6143    0.0767   -1.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0300    1.4081   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4253   -2.0641   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -3.2274   -1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061   -0.6804    0.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748   -1.5727    1.7329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7822   -3.5816    1.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740   -2.6513   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3533   -2.5342    2.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0397   -0.6885   -0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4723    1.2083   -1.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7947    4.3157   -1.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5224    0.8999    2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413    0.0304    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0371    1.1468    0.6607 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  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 19 25  1  0
 25 26  2  0
 11 27  1  0
 27 28  2  0
  6 29  1  0
 29  2  1  0
 28  8  1  0
 26 16  1  0
  3 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 24 43  1  0
 25 44  1  0
 27 45  1  0
 28 46  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Desmethyl-p-O-sulfuric acid rosiglitazone	Generator
N-Desmethyl-p-O-sulphate rosiglitazone	Generator
N-Desmethyl-p-O-sulphuric acid rosiglitazone	Generator

Chemical Formula

C₁₇H₁₇N₃O₇S₂

Average Molecular Weight

439.463

Monoisotopic Molecular Weight

439.050791293

IUPAC Name

{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid

Traditional Name

{6-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)amino]pyridin-3-yl}oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H17N3O7S2/c21-16-14(28-17(22)20-16)9-11-1-3-12(4-2-11)26-8-7-18-15-6-5-13(10-19-15)27-29(23,24)25/h1-6,10,14H,7-9H2,(H,18,19)(H,20,21,22)(H,23,24,25)

InChI Key

ULPCBLHRDLQTTD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as arylsulfates. These are organic compounds containing a sulfate group that carries an aryl group through an ether group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfuric acids and derivatives

Sub Class

Arylsulfates

Direct Parent

Arylsulfates

Alternative Parents

Substituents

Arylsulfate
Phenoxy compound
Phenol ether
Alkyl aryl ether
Aminopyridine
Secondary aliphatic/aromatic amine
Thiazolidinedione
Monocyclic benzene moiety
Pyridine
Sulfuric acid monoester
Sulfate-ester
Imidolactam
Benzenoid
Sulfuric acid ester
Dicarboximide
Heteroaromatic compound
Thiazolidine
Amino acid or derivatives
Thiocarbamic acid derivative
Carbonic acid derivative
Azacycle
Secondary amine
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Amine
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060839)
Liver (HMDB: HMDB0060839)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060839)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060839)

Cellular substructure

Cytoplasm (HMDB: HMDB0060839)

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	0.021 g/L	ALOGPS
logP	1.08	ALOGPS
logP	-1	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	-2.7	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	143.92 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	105.53 m³·mol⁻¹	ChemAxon
Polarizability	42.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	202.721	31661259
DarkChem	[M-H]-	193.558	31661259
DeepCCS	[M+H]+	190.609	30932474
DeepCCS	[M-H]-	188.251	30932474
DeepCCS	[M-2H]-	221.981	30932474
DeepCCS	[M+Na]+	197.209	30932474
AllCCS	[M+H]+	196.3	32859911
AllCCS	[M+H-H2O]+	194.0	32859911
AllCCS	[M+NH4]+	198.4	32859911
AllCCS	[M+Na]+	199.0	32859911
AllCCS	[M-H]-	190.4	32859911
AllCCS	[M+Na-2H]-	190.7	32859911
AllCCS	[M+HCOO]-	191.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl-p-O-sulfate rosiglitazone	OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	6287.2	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone	OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	4005.2	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone	OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	4126.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	4337.0	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	3783.0	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	6286.6	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #2	C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(=O)(=O)O)C=N1	4219.3	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #2	C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(=O)(=O)O)C=N1	3770.3	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #2	C[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(=O)(=O)O)C=N1	6231.4	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(OS(=O)(=O)O)C=N3)C=C2)C1=O	4192.1	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(OS(=O)(=O)O)C=N3)C=C2)C1=O	3752.1	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(OS(=O)(=O)O)C=N3)C=C2)C1=O	5894.1	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C)N=C1	4229.6	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C)N=C1	3832.0	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C)N=C1	5813.2	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	4123.1	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	3850.3	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #2	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)N=C1	5496.0	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(OS(=O)(=O)O)C=N3)[Si](C)(C)C)C=C2)C1=O	4051.7	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(OS(=O)(=O)O)C=N3)[Si](C)(C)C)C=C2)C1=O	3818.5	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TMS,isomer #3	C[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(OS(=O)(=O)O)C=N3)[Si](C)(C)C)C=C2)C1=O	5394.5	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)[Si](C)(C)C)N=C1	4000.4	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)[Si](C)(C)C)N=C1	3904.2	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,3TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C)C3=O)C=C2)[Si](C)(C)C)N=C1	5066.6	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	4575.5	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	4041.8	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)N=C1	6207.3	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(=O)(=O)O)C=N1	4489.0	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(=O)(=O)O)C=N1	3965.9	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=C(OS(=O)(=O)O)C=N1	6157.4	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(OS(=O)(=O)O)C=N3)C=C2)C1=O	4440.8	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(OS(=O)(=O)O)C=N3)C=C2)C1=O	3991.4	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCNC3=CC=C(OS(=O)(=O)O)C=N3)C=C2)C1=O	5769.9	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	4687.9	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	4269.5	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(N(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)[Si](C)(C)C(C)(C)C)N=C1	5713.1	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	4562.5	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	4312.9	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC=C(NCCOC2=CC=C(CC3SC(=O)N([Si](C)(C)C(C)(C)C)C3=O)C=C2)N=C1	5381.7	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(OS(=O)(=O)O)C=N3)[Si](C)(C)C(C)(C)C)C=C2)C1=O	4538.1	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(OS(=O)(=O)O)C=N3)[Si](C)(C)C(C)(C)C)C=C2)C1=O	4244.5	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)SC(CC2=CC=C(OCCN(C3=CC=C(OS(=O)(=O)O)C=N3)[Si](C)(C)C(C)(C)C)C=C2)C1=O	5274.0	Standard polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)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	4637.0	Semi standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)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	4556.6	Standard non polar	33892256
N-Desmethyl-p-O-sulfate rosiglitazone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)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	4998.8	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-O-sulfate rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kmi-0987000000-4a5fd1c5d00b041cf8c4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethyl-p-O-sulfate 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-p-O-sulfate 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-p-O-sulfate rosiglitazone 10V, Positive-QTOF	splash10-0006-1138900000-80edda9cfd47d6c7e5c1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 20V, Positive-QTOF	splash10-01vo-0559100000-58b60ecdd13f08919351	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 40V, Positive-QTOF	splash10-0ab9-0980000000-16bdb2a7a535f6ede58c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 10V, Negative-QTOF	splash10-000i-0424900000-fd79be4ec7e961b1dcb1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 20V, Negative-QTOF	splash10-000f-7889100000-9b5b65e6d906cf207c55	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 40V, Negative-QTOF	splash10-0006-9210000000-afcdd958d2f58478a149	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 10V, Positive-QTOF	splash10-0006-0010900000-9fa06a53354e8d4a7544	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 20V, Positive-QTOF	splash10-00xu-0137900000-afcb2b43ff2e450997a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 40V, Positive-QTOF	splash10-01b9-1931000000-96e5eb9e304dcdd4679b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 10V, Negative-QTOF	splash10-000i-0000900000-5c28d604d12ced5944ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 20V, Negative-QTOF	splash10-0006-9012000000-6c3ecb6922b87f3b6e0d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethyl-p-O-sulfate rosiglitazone 40V, Negative-QTOF	splash10-0006-9110000000-b9c61e4926f785c868cb	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Rosiglitazone Metabolism Pathway		Not Available

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769973

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-O-sulfate rosiglitazone (HMDB0060839)

MOL for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

3D MOL for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

3D SDF for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

3D-SDF for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

PDB for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

3D PDB for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

SMILES for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

INCHI for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

Structure for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

3D Structure for HMDB0060839 (N-Desmethyl-p-O-sulfate rosiglitazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra