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CHEBI:50123 - (+)-rosiglitazone

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:
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).
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).
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