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CHEBI:173109 - RSL3

ChEBI IDCHEBI:173109
ChEBI NameRSL3
Stars
DefinitionA β-carboline that is 2,3,4,4a,9,9a-hexahydro-1H-β-carboline in which the hydrogens at positions 1, 2 and 3 are replaced by 4-(methoxycarbonyl)phenyl, chloroacetyl and methoxycarbonyl groups, respectively (the 1S,2R stereoisomer). It is a potential antineoplastic agent which triggers ferroptosis by inactivating the glutathione peroxidase 4 (GPX4) enzyme.
Last Modified15 March 2024
SubmitterAdnan
DownloadsMolfile
FormulaC23H23ClN2O5
Net Charge0
Average Mass442.899
Monoisotopic Mass442.12955
SMILES[H][C@]1(c2ccc(C(=O)OC)cc2)C2Nc3ccccc3C2C[C@H](C(=O)OC)N1C(=O)CCl
InChIInChI=1S/C23H23ClN2O5/c1-30-22(28)14-9-7-13(8-10-14)21-20-16(15-5-3-4-6-17(15)25-20)11-18(23(29)31-2)26(21)19(27)12-24/h3-10,16,18,20-21,25H,11-12H2,1-2H3/t16?,18-,20?,21+/m1/s1
InChIKeyCKRZDIUOUCGSBK-YBKKDXPLSA-N
Roles Classification
Biological Roles:
ferroptosis inducer  Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms.
EC 1.11.1.9 (glutathione peroxidase) inhibitor  An inhibitor of peroxidases (EC 1.11.1.*) that inhibits the action of glutathione peroxidase (EC 1.11.1.9).
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
RSL3 (CHEBI:173109) has role antineoplastic agent (CHEBI:35610)
RSL3 (CHEBI:173109) has role EC 1.11.1.9 (glutathione peroxidase) inhibitor (CHEBI:176342)
RSL3 (CHEBI:173109) has role ferroptosis inducer (CHEBI:173085)
RSL3 (CHEBI:173109) is a benzoate ester (CHEBI:36054)
RSL3 (CHEBI:173109) is a diester (CHEBI:51307)
RSL3 (CHEBI:173109) is a methyl ester (CHEBI:25248)
RSL3 (CHEBI:173109) is a organochlorine compound (CHEBI:36683)
RSL3 (CHEBI:173109) is a tertiary carboxamide (CHEBI:140326)
RSL3 (CHEBI:173109) is a β-carbolines (CHEBI:60834)
IUPAC Name 
methyl (1S,3R)-2-(chloroacetyl)-1-[4-(methoxycarbonyl)phenyl]-2,3,4,4a,9,9a-hexahydro-1H-β-carboline-3-carboxylate
Synonyms  Source
(1S,3R)-RSL3ChEBI
ras-selective lethal small molecule 3ChEBI
Manual XrefsDatabases
C21479KEGG COMPOUND
Registry NumbersSources
CAS:1219810-16-8ChEBI
Citations