Gboxin - 10mM in DMSO , CAS No.2101315-36-8

CAS: 2101315-36-8 Cat. No.: G422550 Molecular Weight: 392.96

GRADE & PURITY 10mM in DMSO

Synonyms

HY-111651 | 2101315-36-8 | 2-ethyl-1-methyl-3-[2-[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]oxy]-2-oxoethyl]-1H-benzimidazolium, monochloride | Gboxin chloride | MS-26587 | Gboxin | 2-ethyl-3-methyl-1-(2-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohe

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Information

Gboxin Gboxin is an inhibitor of oxidative phosphorylation in cancer cells. Gboxin inhibits the activity of F0F1 ATP synthase . It specifically inhibits the growth of primary mouse and human glioblastoma cells but not that of mouse embryonic fibroblasts or neonatal astrocytes.

Targets

oxidative phosphorylation ; F0F1 ATP synthase

In vitro

Gboxin rapidly and irreversibly compromises GBM oxygen consumption. Reliant on its positive charge, Gboxin associates with mitochondrial oxidative phosphorylation complexes in a proton gradient dependent manner and inhibits F0F1 ATP synthase activity. Gboxin targets unique features of mitochondrial pH in GBM and other cancer cells, independent of their genetic composition, and exerts its tumor cell specific toxicity in primary culture and in vivo.

Cell Research(from reference)

Cell lines：HTS, MEF and astrocyte cells 

Concentrations：0-15 μM 

Incubation Time：96 h 

Specifications

Synonyms

HY-111651 | 2101315-36-8 | 2-ethyl-1-methyl-3-[2-[[(1R, 2S, 5R)-5-methyl-2-(1-methylethyl)cyclohexyl]oxy]-2-oxoethyl]-1H-benzimidazolium, monochloride | Gboxin chloride | MS-26587 | Gboxin | 2-ethyl-3-methyl-1-(2-{[(1R, 2S, 5R)-5-methyl-2-(propan-2-yl)cyclohe

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Gboxin is an inhibitor of oxidative phosphorylation in cancer cells. Gboxin inhibits the activity of F0F1 ATP synthase. It specifically inhibits the growth of primary mouse and human glioblastoma cells but not that of mouse embryonic fibroblasts or neonat

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Action Type

INHIBITOR

Product Properties

• ALogP: 3.086
• hba_count: 2
• Rotatable Bond: 6

Names and Identifiers

• Canonical Smiles: CCC1=[N+](C2=CC=CC=C2N1CC(=O)OC3CC(CCC3C(C)C)C)C.[Cl-]
• IUPAC Name: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-(2-ethyl-3-methylbenzimidazol-3-ium-1-yl)acetate;chloride
• InChIKey: UBWVTCCKVGOTBG-VYZBTARASA-M
• INCHI: 1S/C22H33N2O2.ClH/c1-6-21-23(5)18-9-7-8-10-19(18)24(21)14-22(25)26-20-13-16(4)11-12-17(20)15(2)3;/h7-10,15-17,20H,6,11-14H2,1-5H3;1H/q+1;/p-1/t16-,17+,20-;/m1./s1
• Isomeric SMILES: CCC1=[N+](C2=CC=CC=C2N1CC(=O)O[C@@H]3C[C@@H](CC[C@H]3C(C)C)C)C.[Cl-]
• Molecular Weight: 392.96
• Reaxy-Rn: 31744812
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=31744812&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acid esters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Alpha amino acid esters
• Alternative Parents: Menthane monoterpenoids Bicyclic monoterpenoids Aromatic monoterpenoids Benzimidazoles N-substituted imidazoles Benzenoids Imidazolines Heteroaromatic compounds Carboxylic acid esters Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboximidamides Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organic oxides Organic chloride salts Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-amino acid ester - P-menthane monoterpenoid - Monoterpenoid - Bicyclic monoterpenoid - Aromatic monoterpenoid - Benzimidazole - Benzenoid - N-substituted imidazole - Heteroaromatic compound - 2-imidazoline - Azole - Carboxylic acid ester - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic chloride salt - Organic salt - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
• 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

Mechanisms of Action

Chemical and Physical Properties

• DMSO(mg / mL) Max Solubility: 39
• DMSO(mM) Max Solubility: 99.2467426710098
• Water(mg / mL) Max Solubility: 2
• Water(mM) Max Solubility: 5.08957654723127
• Molecular Weight: 393.000 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 392.223 Da
• Monoisotopic Mass: 392.223 Da
• Topological Polar Surface Area: 35.100 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 481.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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: 2

XLogP3