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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:50 UTC
Update Date2017-12-07 18:14:38 UTC
HMDB IDHMDB0060857
Secondary Accession Numbers
  • HMDB60857
Metabolite Identification
Common Nameo-O-glucuronide rosiglitazone
Descriptiono-O-glucuronide 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
Thumb
SynonymsNot Available
Chemical FormulaC24H27N3O10S
Average Molecular Weight549.55
Monoisotopic Molecular Weight549.141714789
IUPAC Name6-({2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-({2-[(2-{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy}ethyl)(methyl)amino]pyridin-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=CC=N1
InChI Identifier
InChI=1S/C24H27N3O10S/c1-27(9-10-35-13-6-4-12(5-7-13)11-15-21(31)26-24(34)38-15)20-14(3-2-8-25-20)36-23-18(30)16(28)17(29)19(37-23)22(32)33/h2-8,15-19,23,28-30H,9-11H2,1H3,(H,32,33)(H,26,31,34)
InChI KeyYDRMOALONMVDNG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Phenol ether
  • Phenoxy compound
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aminopyridine
  • Thiazolidinedione
  • Beta-hydroxy acid
  • Pyridine
  • Monocyclic benzene moiety
  • Pyran
  • Oxane
  • Benzenoid
  • Imidolactam
  • Monosaccharide
  • Hydroxy acid
  • Dicarboximide
  • Heteroaromatic compound
  • Thiazolidine
  • Secondary alcohol
  • Carbonic acid derivative
  • Thiocarbamic acid derivative
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Ether
  • Oxacycle
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.01 g/LALOGPS
logP0.55ALOGPS
logP-0.91ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)5.97ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area187.98 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity131.78 m³·mol⁻¹ChemAxon
Polarizability53.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-057u-9520220000-a75c8b98985881fb62ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0210-4922125000-a1aee337d1679760759dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kn9-0119070000-e662f47174021a913e9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0529000000-3d422219d26241d5153eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pi0-0965000000-084cdfe86ba00b10b020View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uka-1339170000-df138e0a3615439f874aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdo-6359320000-bf8d6b9b8fcb7ae66b76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9103000000-4a105c456cdd490f3ec7View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Rosiglitazone Metabolism PathwayPw000629Pw000629 greyscalePw000629 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00968
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available