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CHEBI:50125 - (−)-rosiglitazone
| Formula | C18H19N3O3S |
| Net Charge | 0 |
| Average Mass | 357.435 |
| Monoisotopic Mass | 357.11471 |
| SMILES | CN(CCOc1ccc(C[C@@H]2SC(=O)NC2=O)cc1)c1ccccn1 |
| InChI | 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)/t15-/m0/s1 |
| InChIKey | YASAKCUCGLMORW-HNNXBMFYSA-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). insulin-sensitizing drug An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma). 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. |
| 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:50125) is a rosiglitazone (CHEBI:50122) |
| (−)-rosiglitazone (CHEBI:50125) is enantiomer of (+)-rosiglitazone (CHEBI:50123) |
| Incoming Relation(s) |
| (+)-rosiglitazone (CHEBI:50123) is enantiomer of (−)-rosiglitazone (CHEBI:50125) |
| IUPAC Name |
|---|
| (5S)-5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione |