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Record Information
Version3.6
Creation Date2013-07-09 16:18:47 UTC
Update Date2016-02-11 08:18:34 UTC
HMDB IDHMDB61105
Secondary Accession NumbersNone
Metabolite Identification
Common Nameortho-hydroxyrosiglitazone
Descriptionortho-hydroxyrosiglitazone 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 FormulaC18H19N3O4S
Average Molecular Weight373.426
Monoisotopic Molecular Weight373.109626801
IUPAC Name4-hydroxy-5-[(4-{2-[(3-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-2,5-dihydro-1,3-thiazol-2-one
Traditional Name4-hydroxy-5-[(4-{2-[(3-hydroxypyridin-2-yl)(methyl)amino]ethoxy}phenyl)methyl]-5H-1,3-thiazol-2-one
CAS Registry NumberNot Available
SMILES
CN(CCOC1=CC=C(CC2SC(=O)N=C2O)C=C1)C1=C(O)C=CC=N1
InChI Identifier
InChI=1/C18H19N3O4S/c1-21(16-14(22)3-2-8-19-16)9-10-25-13-6-4-12(5-7-13)11-15-17(23)20-18(24)26-15/h2-8,15,22H,9-11H2,1H3,(H,20,23,24)
InChI KeyInChIKey=KQXWMUFVDAFGPU-UHFFFAOYNA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Solubility0.13 mg/mLALOGPS
logP2.71ALOGPS
logP2.14ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)5.81ChemAxon
pKa (Strongest Basic)6.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.25 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.09 m3·mol-1ChemAxon
Polarizability38.73 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00470
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 LinkHMDB61105
Metagene LinkHMDB61105
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