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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:47 UTC
Update Date2017-12-07 18:50:48 UTC
HMDB IDHMDB0061105
Secondary Accession Numbers
  • HMDB61105
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=1S/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 KeyKQXWMUFVDAFGPU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenol ethers
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aminopyridine
  • Hydroxypyridine
  • Monocyclic benzene moiety
  • Pyridine
  • Imidolactam
  • Heteroaromatic compound
  • Meta-thiazoline
  • Carbonic acid derivative
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • 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 Solubility0.13 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.09 m³·mol⁻¹ChemAxon
Polarizability38.73 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-05g0-4932000000-7da5f4e50b59ced3de23View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ue9-4692150000-00d6fad719ebbe3a8e5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0219000000-9ee1246f5606ccba338cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0925000000-f2f1a0547338d02c0277View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-1910000000-5d149c7a5cc9dd4d2862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0229000000-0ff802c62bbd3068bda8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ukc-6897000000-69fdd4c434bd3e0ba13aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-bca081c8bd3472d80bfcView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 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
      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