Cysmethynil - ≥98% , CAS No.851636-83-4

CAS: 851636-83-4 Cat. No.: C342660 Molecular Weight: 376.53

GRADE & PURITY ≥98%

Synonyms

2-[5-(3-methylphenyl)-1-octylindol-3-yl]acetamide | 2-[5-(3-methylphenyl)-1-octyl-1h-indol-3-yl] acetamide | AKOS032947852 | A-119044 | DTXSID90426093 | Icmt Inhibitor | Cysmethynil | BCP21581 | Q5201174 | BDBM50327696 | HMS3740K09 | 2-(1-octyl-5-m-tolyl-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Product Describtion:

Post-translational protein prenylation is a 3-step process that occurs at the C-terminus of a number of proteins involved in cell growth control and oncogenesis. Isoprenylcysteine carboxyl methyltransferase (Icmt) catalyzes the methylation of C-terminal prenylcysteine residues, the last step in this process. Cysmethynil is an indole-based, time-dependent inhibitor of Icmt (IC50 = adenosylmethionine (Ki = 0.14 µM for the final complex). It does not inhibit other enzymes in the prenylation pathway (farensyltransferase, geranylgeranyltransferase type I, and Rce1) at concentrations up to 50 µM, or related methyltransferases. Treatment of cancer cells results in a dose-dependent decrease in Ras carboxylmethylation, mislocalization of Ras, and impaired signaling through Ras pathways. Treatment of PC3 prostate cancer cells with 25 µM cysmethynil resulted in decreased mTOR signaling, accumulation of cells in the G1 phase, and autophagy-mediated cell death.

Specifications

Synonyms

2-[5-(3-methylphenyl)-1-octylindol-3-yl]acetamide | 2-[5-(3-methylphenyl)-1-octyl-1h-indol-3-yl] acetamide | AKOS032947852 | A-119044 | DTXSID90426093 | Icmt Inhibitor | Cysmethynil | BCP21581 | Q5201174 | BDBM50327696 | HMS3740K09 | 2-(1-octyl-5-m-tolyl-

Specifications & Purity

≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504764381
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764381
• Canonical Smiles: CCCCCCCCN1C=C(C2=C1C=CC(=C2)C3=CC=CC(=C3)C)CC(=O)N
• IUPAC Name: 2-[5-(3-methylphenyl)-1-octylindol-3-yl]acetamide
• InChIKey: QIXBOOVPFRZHQQ-UHFFFAOYSA-N
• INCHI: 1S/C25H32N2O/c1-3-4-5-6-7-8-14-27-18-22(17-25(26)28)23-16-21(12-13-24(23)27)20-11-9-10-19(2)15-20/h9-13,15-16,18H,3-8,14,17H2,1-2H3,(H2,26,28)
• Isomeric SMILES: CCCCCCCCN1C=C(C2=C1C=CC(=C2)C3=CC=CC(=C3)C)CC(=O)N
• Molecular Weight: 376.53
• Reaxy-Rn: 10719509
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=10719509&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Indoles and derivatives
      • Subclass N-alkylindoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Indoles and derivatives
• Subclass: N-alkylindoles
• Intermediate Tree Nodes: Not available
• Direct Parent: N-alkylindoles
• Alternative Parents: 3-alkylindoles Toluenes Substituted pyrroles Heteroaromatic compounds Primary carboxylic acid amides Azacyclic compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3-alkylindole - N-alkylindole - Indole - Toluene - Monocyclic benzene moiety - Substituted pyrrole - Benzenoid - Pyrrole - Heteroaromatic compound - Primary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Azacycle - Carbonyl group - Organic oxide - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
• 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)

FYN Tclin Tyrosine-protein kinase FYN (5308 Activities)

Discover Target: FYN

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

PANC-1 (6144 Activities)

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PC-3 (62116 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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HepG2 (196354 Activities)

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MDA-MB-231 (73002 Activities)

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IMR-90 (216 Activities)

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Liver microsomes (16955 Activities)

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Capan-2 (270 Activities)

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HuP-T4 (128 Activities)

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

Associated Targets(non-human)

Icmt Isoprenylcysteine carboxyl methyltransferase (12 Activities)

Discover Target: Icmt

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in ethanol (~20 mg/ml), DMSO (~5 mg/ml), and DMF (~3.3 mg/ml).
• Boil Point(°C): ~573.81° C (Predicted)
• Melt Point(°C): ~247.08° C (Predicted)
• Molecular Weight: 376.500 g/mol
• XLogP3: 6.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 376.251 Da
• Monoisotopic Mass: 376.251 Da
• Topological Polar Surface Area: 48.000 Ų
• Heavy Atom Count: 28
• Formal Charge: 0
• Complexity: 479.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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