CHEBI:173109 - RSL3

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ChEBI Name RSL3
ChEBI ID CHEBI:173109
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H23ClN2O5
Net Charge 0
Average Mass 442.900
Monoisotopic Mass 442.12955
InChI InChI=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
InChIKey CKRZDIUOUCGSBK-YBKKDXPLSA-N
SMILES [H][C@@]1(C2NC3=C(C=CC=C3)C2C[C@@H](N1C(=O)CCl)C(=O)OC)C1=CC=C(C=C1)C(=O)OC
Roles Classification
Biological Role(s): 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).
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 β-carbolines (CHEBI:60834)
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)
IUPAC Name
methyl (1S,3R)-2-(chloroacetyl)-1-[4-(methoxycarbonyl)phenyl]-2,3,4,4a,9,9a-hexahydro-1H-β-carboline-3-carboxylate
Synonyms Sources
(1S,3R)-RSL3 ChEBI
ras-selective lethal small molecule 3 ChEBI
Manual Xref Database
C21479 KEGG COMPOUND
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Registry Number Type Source
1219810-16-8 CAS Registry Number ChEBI
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Last Modified
15 March 2024