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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:54 UTC

Update Date

2021-09-14 14:57:39 UTC

HMDB ID

HMDB0060858

Secondary Accession Numbers

HMDB60858

Metabolite Identification

Common Name

o-O-sulfate rosiglitazone

Description

o-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 07041312032D          

 30 32  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 N   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
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    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
    5.7158   -3.3000    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
    6.3832   -4.6099    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -5.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6132   -6.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -5.3945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483   -4.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -4.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   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
    0.0000   -1.6500    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
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -4.0145    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
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 23 26  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END

HMDB0060858
     RDKit          3D
o-O-sulfate rosiglitazone
 49 51  0  0  0  0  0  0  0  0999 V2000
   -2.7976   -0.9469   -2.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036   -0.3682   -1.1508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    0.3788   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3848    0.9314    0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741    1.6502    0.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387    1.3172    1.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031    0.0788    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.1751    0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    0.8355    1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481    0.5751    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0195    0.7968    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -0.3434   -1.0531 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5799   -1.6258   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139   -2.7037   -1.4270 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4635   -1.1383    0.1498 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3979    0.2482    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3808    1.0285    0.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849    2.0805    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9464    2.3241    1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928   -0.5145   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -1.3616    0.8849 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254   -1.5893    1.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4388   -0.9358    1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7287   -0.0717    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    0.1336   -0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1387    1.0088   -1.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9864    0.5838   -2.5361 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.1740    0.8088   -3.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2184    1.4589   -2.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4550   -1.0292   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -0.2048   -3.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -1.7177   -2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7726   -1.4457   -2.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    1.2423   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5136   -0.2086   -1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556    0.1387    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2697    1.6370    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9592   -0.7297    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -1.1888    0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -0.4703    1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465    1.2931    2.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0149    1.8309   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1239   -1.7620    0.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9733    2.8801    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    3.3093    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.2854    2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1420   -1.1194    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6714    0.4492    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0907   -1.5299   -3.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  2  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  2  0
 27 30  1  0
 19  6  1  0
 25 20  1  0
 16 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 15 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 30 49  1  0
M  END


  Mrv0541 07041312032D          

 30 32  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 N   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
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    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
    5.7158   -3.3000    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
    6.3832   -4.6099    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -5.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6132   -6.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -5.3945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0483   -4.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -4.3550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   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
    0.0000   -1.6500    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
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -4.0145    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
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 23 26  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 20 30  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060858

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OS(O)(=O)=O)C=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19N3O7S2/c1-21(16-14(3-2-8-19-16)28-30(24,25)26)9-10-27-13-6-4-12(5-7-13)11-15-17(22)20-18(23)29-15/h2-8,15H,9-11H2,1H3,(H,20,22,23)(H,24,25,26)

> <INCHI_KEY>
ZVSPRKOUHTZIGH-UHFFFAOYSA-N

> <FORMULA>
C18H19N3O7S2

> <MOLECULAR_WEIGHT>
453.489

> <EXACT_MASS>
453.066441357

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
43.5517692529107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
-0.36775679615997636

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.631277773237848

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.535711764991354

> <JCHEM_PKA_STRONGEST_BASIC>
5.214747431143771

> <JCHEM_POLAR_SURFACE_AREA>
135.13

> <JCHEM_REFRACTIVITY>
109.76259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.67e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060858
     RDKit          3D
o-O-sulfate rosiglitazone
 49 51  0  0  0  0  0  0  0  0999 V2000
   -2.7976   -0.9469   -2.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036   -0.3682   -1.1508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    0.3788   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3848    0.9314    0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741    1.6502    0.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387    1.3172    1.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031    0.0788    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.1751    0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    0.8355    1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481    0.5751    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0195    0.7968    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -0.3434   -1.0531 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5799   -1.6258   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139   -2.7037   -1.4270 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4635   -1.1383    0.1498 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3979    0.2482    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3808    1.0285    0.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849    2.0805    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9464    2.3241    1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928   -0.5145   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -1.3616    0.8849 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254   -1.5893    1.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4388   -0.9358    1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7287   -0.0717    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    0.1336   -0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1387    1.0088   -1.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9864    0.5838   -2.5361 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.1740    0.8088   -3.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2184    1.4589   -2.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4550   -1.0292   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -0.2048   -3.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -1.7177   -2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7726   -1.4457   -2.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    1.2423   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5136   -0.2086   -1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556    0.1387    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2697    1.6370    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9592   -0.7297    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -1.1888    0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -0.4703    1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465    1.2931    2.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0149    1.8309   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1239   -1.7620    0.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9733    2.8801    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    3.3093    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.2854    2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1420   -1.1194    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6714    0.4492    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0907   -1.5299   -3.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  2  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  2  0
 27 30  1  0
 19  6  1  0
 25 20  1  0
 16 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 15 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 30 49  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.334  -3.850   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      11.915  -8.605   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0      11.439 -10.070   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.345 -11.316   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       9.899 -10.070   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.423  -8.605   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.959  -8.129   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  S   UNK     0      -2.667  -6.160   0.000  0.00  0.00           S+0
HETATM   24  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.437  -4.826   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.897  -7.494   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18    9   19                                                       
CONECT   19   18    6                                                       
CONECT   20    2   21   30                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   21   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   20                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

COMPND    HMDB0060858
HETATM    1  C1  UNL     1      -2.798  -0.947  -2.470  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.604  -0.368  -1.151  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.392   0.379  -0.838  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.385   0.931   0.560  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.274   1.650   0.927  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.039   1.317   1.054  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.603   0.079   0.846  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.967  -0.175   0.997  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.815   0.836   1.372  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.248   0.575   1.534  1.00  0.00           C  
HETATM   11  C9  UNL     1       6.020   0.797   0.241  1.00  0.00           C  
HETATM   12  S1  UNL     1       5.362  -0.343  -1.053  1.00  0.00           S  
HETATM   13  C10 UNL     1       6.580  -1.626  -0.831  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.614  -2.704  -1.427  1.00  0.00           O  
HETATM   15  N2  UNL     1       7.464  -1.138   0.150  1.00  0.00           N  
HETATM   16  C11 UNL     1       7.398   0.248   0.347  1.00  0.00           C  
HETATM   17  O3  UNL     1       8.381   1.029   0.598  1.00  0.00           O  
HETATM   18  C12 UNL     1       3.285   2.081   1.588  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.946   2.324   1.437  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.593  -0.515  -0.155  1.00  0.00           C  
HETATM   21  N3  UNL     1      -3.363  -1.362   0.885  1.00  0.00           N  
HETATM   22  C15 UNL     1      -4.225  -1.589   1.877  1.00  0.00           C  
HETATM   23  C16 UNL     1      -5.439  -0.936   1.875  1.00  0.00           C  
HETATM   24  C17 UNL     1      -5.729  -0.072   0.857  1.00  0.00           C  
HETATM   25  C18 UNL     1      -4.799   0.134  -0.155  1.00  0.00           C  
HETATM   26  O4  UNL     1      -5.139   1.009  -1.145  1.00  0.00           O  
HETATM   27  S2  UNL     1      -5.986   0.584  -2.536  1.00  0.00           S  
HETATM   28  O5  UNL     1      -5.174   0.809  -3.774  1.00  0.00           O  
HETATM   29  O6  UNL     1      -7.218   1.459  -2.626  1.00  0.00           O  
HETATM   30  O7  UNL     1      -6.455  -1.029  -2.400  1.00  0.00           O  
HETATM   31  H1  UNL     1      -2.692  -0.205  -3.266  1.00  0.00           H  
HETATM   32  H2  UNL     1      -1.982  -1.718  -2.624  1.00  0.00           H  
HETATM   33  H3  UNL     1      -3.773  -1.446  -2.516  1.00  0.00           H  
HETATM   34  H4  UNL     1      -1.400   1.242  -1.585  1.00  0.00           H  
HETATM   35  H5  UNL     1      -0.514  -0.209  -1.120  1.00  0.00           H  
HETATM   36  H6  UNL     1      -1.656   0.139   1.297  1.00  0.00           H  
HETATM   37  H7  UNL     1      -2.270   1.637   0.600  1.00  0.00           H  
HETATM   38  H8  UNL     1       0.959  -0.730   0.566  1.00  0.00           H  
HETATM   39  H9  UNL     1       3.353  -1.189   0.815  1.00  0.00           H  
HETATM   40  H10 UNL     1       5.386  -0.470   1.849  1.00  0.00           H  
HETATM   41  H11 UNL     1       5.647   1.293   2.272  1.00  0.00           H  
HETATM   42  H12 UNL     1       6.015   1.831  -0.098  1.00  0.00           H  
HETATM   43  H13 UNL     1       8.124  -1.762   0.695  1.00  0.00           H  
HETATM   44  H14 UNL     1       3.973   2.880   1.887  1.00  0.00           H  
HETATM   45  H15 UNL     1       1.565   3.309   1.614  1.00  0.00           H  
HETATM   46  H16 UNL     1      -3.981  -2.285   2.688  1.00  0.00           H  
HETATM   47  H17 UNL     1      -6.142  -1.119   2.682  1.00  0.00           H  
HETATM   48  H18 UNL     1      -6.671   0.449   0.837  1.00  0.00           H  
HETATM   49  H19 UNL     1      -6.091  -1.530  -3.175  1.00  0.00           H  
CONECT    1    2   31   32   33
CONECT    2    3   20
CONECT    3    4   34   35
CONECT    4    5   36   37
CONECT    5    6
CONECT    6    7    7   19
CONECT    7    8   38
CONECT    8    9    9   39
CONECT    9   10   18
CONECT   10   11   40   41
CONECT   11   12   16   42
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   43
CONECT   16   17   17
CONECT   18   19   19   44
CONECT   19   45
CONECT   20   21   21   25
CONECT   21   22
CONECT   22   23   23   46
CONECT   23   24   47
CONECT   24   25   25   48
CONECT   25   26
CONECT   26   27
CONECT   27   28   28   29   29
CONECT   27   30
CONECT   30   49
END

HMDB0060858
     RDKit          3D
o-O-sulfate rosiglitazone
 49 51  0  0  0  0  0  0  0  0999 V2000
   -2.7976   -0.9469   -2.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036   -0.3682   -1.1508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    0.3788   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3848    0.9314    0.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2741    1.6502    0.9268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387    1.3172    1.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031    0.0788    0.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -0.1751    0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148    0.8355    1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481    0.5751    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0195    0.7968    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -0.3434   -1.0531 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5799   -1.6258   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6139   -2.7037   -1.4270 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4635   -1.1383    0.1498 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3979    0.2482    0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3808    1.0285    0.5977 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2849    2.0805    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9464    2.3241    1.4371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5928   -0.5145   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -1.3616    0.8849 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254   -1.5893    1.8772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4388   -0.9358    1.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7287   -0.0717    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7986    0.1336   -0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1387    1.0088   -1.1450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9864    0.5838   -2.5361 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.1740    0.8088   -3.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2184    1.4589   -2.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4550   -1.0292   -2.4001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -0.2048   -3.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823   -1.7177   -2.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7726   -1.4457   -2.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000    1.2423   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5136   -0.2086   -1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556    0.1387    1.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2697    1.6370    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9592   -0.7297    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3528   -1.1888    0.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3862   -0.4703    1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465    1.2931    2.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0149    1.8309   -0.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1239   -1.7620    0.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9733    2.8801    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    3.3093    1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9807   -2.2854    2.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1420   -1.1194    2.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6714    0.4492    0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0907   -1.5299   -3.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
  9 18  1  0
 18 19  2  0
  2 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  2  0
 27 29  2  0
 27 30  1  0
 19  6  1  0
 25 20  1  0
 16 11  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  7 38  1  0
  8 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 15 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 30 49  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
O-O-Sulfuric acid rosiglitazone	Generator
O-O-Sulphate rosiglitazone	Generator
O-O-Sulphuric acid rosiglitazone	Generator

Chemical Formula

C₁₈H₁₉N₃O₇S₂

Average Molecular Weight

453.489

Monoisotopic Molecular Weight

453.066441357

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OS(O)(=O)=O)C=CC=N1

InChI Identifier

InChI=1S/C18H19N3O7S2/c1-21(16-14(3-2-8-19-16)28-30(24,25)26)9-10-27-13-6-4-12(5-7-13)11-15-17(22)20-18(23)29-15/h2-8,15H,9-11H2,1H3,(H,20,22,23)(H,24,25,26)

InChI Key

ZVSPRKOUHTZIGH-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
Dialkylarylamine
Alkyl aryl ether
Aminopyridine
Thiazolidinedione
Monocyclic benzene moiety
Pyridine
Sulfuric acid monoester
Sulfate-ester
Imidolactam
Benzenoid
Sulfuric acid ester
Dicarboximide
Heteroaromatic compound
Thiazolidine
Carbonic acid derivative
Thiocarbamic acid derivative
Azacycle
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060858)
Liver (HMDB: HMDB0060858)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060858)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060858)

Cellular substructure

Cytoplasm (HMDB: HMDB0060858)

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	0.027 g/L	ALOGPS
logP	0.71	ALOGPS
logP	-0.37	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	-2.5	ChemAxon
pKa (Strongest Basic)	5.21	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	135.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	109.76 m³·mol⁻¹	ChemAxon
Polarizability	43.55 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]+	198.871	31661259
DarkChem	[M-H]-	193.273	31661259
DeepCCS	[M+H]+	196.158	30932474
DeepCCS	[M-H]-	193.8	30932474
DeepCCS	[M-2H]-	227.69	30932474
DeepCCS	[M+Na]+	203.126	30932474
AllCCS	[M+H]+	201.6	32859911
AllCCS	[M+H-H2O]+	199.4	32859911
AllCCS	[M+NH4]+	203.7	32859911
AllCCS	[M+Na]+	204.3	32859911
AllCCS	[M-H]-	194.4	32859911
AllCCS	[M+Na-2H]-	194.8	32859911
AllCCS	[M+HCOO]-	195.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
o-O-sulfate rosiglitazone	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OS(O)(=O)=O)C=CC=N1	5869.7	Standard polar	33892256
o-O-sulfate rosiglitazone	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OS(O)(=O)=O)C=CC=N1	3670.0	Standard non polar	33892256
o-O-sulfate rosiglitazone	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OS(O)(=O)=O)C=CC=N1	3960.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
o-O-sulfate rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C	4106.6	Semi standard non polar	33892256
o-O-sulfate rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C	3698.6	Standard non polar	33892256
o-O-sulfate rosiglitazone,1TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C	6045.7	Standard polar	33892256
o-O-sulfate rosiglitazone,1TMS,isomer #2	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O	3902.8	Semi standard non polar	33892256
o-O-sulfate rosiglitazone,1TMS,isomer #2	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O	3678.2	Standard non polar	33892256
o-O-sulfate rosiglitazone,1TMS,isomer #2	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O	5621.8	Standard polar	33892256
o-O-sulfate rosiglitazone,2TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C	3851.8	Semi standard non polar	33892256
o-O-sulfate rosiglitazone,2TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C	3795.6	Standard non polar	33892256
o-O-sulfate rosiglitazone,2TMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C	5243.4	Standard polar	33892256
o-O-sulfate rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	4308.7	Semi standard non polar	33892256
o-O-sulfate rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	3945.0	Standard non polar	33892256
o-O-sulfate rosiglitazone,1TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	5958.8	Standard polar	33892256
o-O-sulfate rosiglitazone,1TBDMS,isomer #2	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O	4164.3	Semi standard non polar	33892256
o-O-sulfate rosiglitazone,1TBDMS,isomer #2	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O	3919.4	Standard non polar	33892256
o-O-sulfate rosiglitazone,1TBDMS,isomer #2	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O	5508.7	Standard polar	33892256
o-O-sulfate rosiglitazone,2TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	4262.5	Semi standard non polar	33892256
o-O-sulfate rosiglitazone,2TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	4270.8	Standard non polar	33892256
o-O-sulfate rosiglitazone,2TBDMS,isomer #1	CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=NC=CC=C1OS(=O)(=O)O[Si](C)(C)C(C)(C)C	5121.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - o-O-sulfate rosiglitazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0lki-3893100000-5d537f4f362e7fdde618	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - o-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 - o-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 - o-O-sulfate rosiglitazone 10V, Positive-QTOF	splash10-0udi-1026900000-d5f4def62234b81ae74a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 20V, Positive-QTOF	splash10-0a4i-0779300000-d78454825656299171cf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 40V, Positive-QTOF	splash10-0a4r-0960000000-c42afe3114e4a55d2c42	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 10V, Negative-QTOF	splash10-0udi-0054900000-58ea7daf2c17e0987854	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 20V, Negative-QTOF	splash10-0fdo-3194000000-b0217b37e1c497627ffa	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 40V, Negative-QTOF	splash10-0006-9111000000-36abe241a6dd4ee392be	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 10V, Positive-QTOF	splash10-0udi-0020900000-57976c9112e987ec03e2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 20V, Positive-QTOF	splash10-0f89-0349300000-c608de77005b591d2c68	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 40V, Positive-QTOF	splash10-0019-1970000000-dbaaf542207af5f9c610	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 10V, Negative-QTOF	splash10-0udi-1162900000-834337caceec87604e84	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 20V, Negative-QTOF	splash10-000x-9013100000-d7cabc1a1f5360a534ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - o-O-sulfate rosiglitazone 40V, Negative-QTOF	splash10-0006-9000100000-6a2a34adbcff6d2e119e	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

131769978

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 o-O-sulfate rosiglitazone (HMDB0060858)

MOL for HMDB0060858 (o-O-sulfate rosiglitazone)

3D MOL for HMDB0060858 (o-O-sulfate rosiglitazone)

3D SDF for HMDB0060858 (o-O-sulfate rosiglitazone)

3D-SDF for HMDB0060858 (o-O-sulfate rosiglitazone)

PDB for HMDB0060858 (o-O-sulfate rosiglitazone)

3D PDB for HMDB0060858 (o-O-sulfate rosiglitazone)

SMILES for HMDB0060858 (o-O-sulfate rosiglitazone)

INCHI for HMDB0060858 (o-O-sulfate rosiglitazone)

Structure for HMDB0060858 (o-O-sulfate rosiglitazone)

3D Structure for HMDB0060858 (o-O-sulfate rosiglitazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra