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CHEBI:50123 - (+)-rosiglitazone

Default Structure
ChEBI IDCHEBI:50123
ChEBI Name(+)-rosiglitazone
Stars
Last Modified17 October 2009
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC18H19N3O3S
Net Charge0
Average Mass357.435
Monoisotopic Mass357.11471
SMILESCN(CCOc1ccc(C[C@H]2SC(=O)NC2=O)cc1)c1ccccn1
InChIInChI=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)/t15-/m1/s1
InChIKeyYASAKCUCGLMORW-OAHLLOKOSA-N
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
ferroptosis inhibitor  Any substance that inhibits the process of ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor  An EC 6.2.1.* (acid-thiol ligase) inhibitor that interferes with the action of a long-chain-fatty-acid—CoA ligase (EC 6.2.1.3).
Application:
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
ChEBI Ontology
Outgoing Relation(s)
(+)-rosiglitazone (CHEBI:50123) is a rosiglitazone (CHEBI:50122)
(+)-rosiglitazone (CHEBI:50123) is enantiomer of (−)-rosiglitazone (CHEBI:50125)
Incoming Relation(s)
(−)-rosiglitazone (CHEBI:50125) is enantiomer of (+)-rosiglitazone (CHEBI:50123)
IUPAC Name 
(5R)-5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione
Manual XrefsDatabases
DB00412DrugBank
Registry NumbersSources
Beilstein:7082203Beilstein