Showing metabocard for Rosiglitazone (BMDB0005031)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:49 UTC
Update Date2020-04-22 15:15:10 UTC
BMDB IDBMDB0005031
Secondary Accession Numbers
  • BMDB05031
Metabolite Identification
Common NameRosiglitazone
DescriptionRosiglitazone, also known as BRL-49653 or gaudil, belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Rosiglitazone is a very strong basic compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-((4-(2-(Methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedioneChEBI
BRL-49653ChEBI
RosiglitazonaChEBI
RosiglitazonumChEBI
GaudilKegg
AvandiaHMDB
Rosiglitazone maleateHMDB
RosiglizoleHMDB
5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioateHMDB
GlaxoSmithKline brand OF rosiglitazone maleateHMDB
SmithKline beecham brand OF rosiglitazone maleateHMDB
Glaxo wellcome brand OF rosiglitazone maleateHMDB
Chemical FormulaC18H19N3O3S
Average Molecular Weight357.427
Monoisotopic Molecular Weight357.114712179
IUPAC Name5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
Traditional Namerosiglitazone
CAS Registry Number122320-73-4
SMILES
CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1
InChI Identifier
InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)
InChI KeyYASAKCUCGLMORW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aminopyridine
  • Monocyclic benzene moiety
  • Pyridine
  • Imidolactam
  • Heteroaromatic compound
  • Meta-thiazoline
  • Carbonic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.95ALOGPS
logP2.45ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.84ChemAxon
pKa (Strongest Basic)6.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.79 m³·mol⁻¹ChemAxon
Polarizability37.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005031
DrugBank IDDB00412
Phenol Explorer Compound IDNot Available
FooDB IDFDB023598
KNApSAcK IDNot Available
Chemspider ID70383
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRosiglitazone
METLIN IDNot Available
PubChem Compound77999
PDB IDNot Available
ChEBI ID50122
References
Synthesis ReferenceManne Reddy, "Amorphous form of rosiglitazone maleate and process for preparation thereof." U.S. Patent US20040242658, issued December 02, 2004.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available