RSL3 - Moligand™, ≥98% , CAS No.1219810-16-8

CAS: 1219810-16-8 Cat. No.: R302648 Formula: C₂₃H₂₁ClN₂O₅ Molecular Weight: 440.88 PubChem CID: 1750826

GRADE & PURITY Moligand™, ≥98%

Synonyms

(1S,3R)-RSL3 | 1S,3R-RSL3 | (1S,3R)-Methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

RSL3 ((1S,3R)-RSL3) is an inhibitor of glutathione peroxidase 4 (GPX4) (ferroptosis activator), reduces the expression of GPX4 protein, and induces ferroptotic death of head and neck cancer cell. RSL3 increases the expression of p62 and Nrf2 and inactivates Keap1 in HN3-rslR cells

Specifications

Synonyms

(1S,3R)-RSL3 | 1S,3R-RSL3 | (1S,3R)-Methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

Glutathione peroxidase 4 (GPX4) inhibitor. Induces ferroptosis. Increases lipid peroxidase levelsin vitro. Inhibits tumor formation and progressionin vivo.

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504760629
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760629
• Canonical Smiles: COC(=O)C1CC2=C(C(N1C(=O)CCl)C3=CC=C(C=C3)C(=O)OC)NC4=CC=CC=C24
• IUPAC Name: methyl (1S,3R)-2-(2-chloroacetyl)-1-(4-methoxycarbonylphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• InChIKey: TXJZRSRTYPUYRW-NQIIRXRSSA-N
• INCHI: 1S/C23H21ClN2O5/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/h3-10,18,21,25H,11-12H2,1-2H3/t18-,21+/m1/s1
• Isomeric SMILES: COC(=O)[C@H]1CC2=C([C@@H](N1C(=O)CCl)C3=CC=C(C=C3)C(=O)OC)NC4=CC=CC=C24
• PubChem CID: 1750826
• Molecular Weight: 440.88

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Harmala alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Harmala alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Harmala alkaloids
• Alternative Parents: Alpha amino acid esters Beta carbolines 3-alkylindoles Benzoic acid esters Benzoyl derivatives Dicarboxylic acids and derivatives Methyl esters Heteroaromatic compounds Tertiary carboxylic acid amides Chloroacetamides Pyrroles Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organochlorides Organonitrogen compounds Organopnictogen compounds Alkyl chlorides Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Harman - Alpha-amino acid ester - Beta-carboline - Pyridoindole - Alpha-amino acid or derivatives - Benzoate ester - 3-alkylindole - Benzoic acid or derivatives - Indole - Indole or derivatives - Benzoyl - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Benzenoid - Methyl ester - Tertiary carboxylic acid amide - Pyrrole - Chloroacetamide - Heteroaromatic compound - Carboxamide group - Carboxylic acid ester - Carboxylic acid derivative - Organoheterocyclic compound - Azacycle - Organic nitrogen compound - Organohalogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organochloride - Organopnictogen compound - Alkyl chloride - Organic oxygen compound - Organooxygen compound - Alkyl halide - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as harmala alkaloids. These are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GPX4 Tchem Phospholipid hydroperoxide glutathione peroxidase (1 Activities)

Discover Target: GPX4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Calu-1 (518 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HT-1080 (3966 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MIA PaCa-2 (5949 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

HT-22 (3261 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

4T1 (1737 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:DMSO, Max Conc. mg/mL: 44.09, Max Conc. mM: 100
• Sensitivity: Moisture sensitive
• Molecular Weight: 440.900 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 440.114 Da
• Monoisotopic Mass: 440.114 Da
• Topological Polar Surface Area: 88.700 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 695.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1