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Record Information
Version3.6
Creation Date2013-07-04 19:04:10 UTC
Update Date2017-03-02 22:05:29 UTC
HMDB IDHMDB60862
Secondary Accession NumbersNone
Metabolite Identification
Common Namep-O-glucuronide rosiglitazone
Descriptionp-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-({6-[(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-({6-[(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=CC=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=N1
InChI Identifier
InChI=1S/C24H27N3O10S/c1-27(8-9-35-13-4-2-12(3-5-13)10-15-21(31)26-24(34)38-15)16-7-6-14(11-25-16)36-23-19(30)17(28)18(29)20(37-23)22(32)33/h2-7,11,15,17-20,23,28-30H,8-10H2,1H3,(H,32,33)(H,26,31,34)
InChI KeyQGESYIGEZXWVIN-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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility0.98 mg/mLALOGPS
logP0.78ALOGPS
logP-0.84ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.97ChemAxon
pKa (Strongest Basic)5.62ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area187.98 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity131.78 m3·mol-1ChemAxon
Polarizability53.71 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot 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 IDDBMET00981
      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
      NuGOwiki LinkHMDB60862
      Metagene LinkHMDB60862
      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