(2-{[3-(methanesulfonylsulfanyl)propanoyl]oxy}ethyl)trimethylazanium chloride

• ChemBase ID: 163741
• Molecular Formular: C9H20ClNO4S2
• Molecular Mass: 305.8424
• Monoisotopic Mass: 305.05222781
• SMILES: CS(=O)(=O)SCCC(=O)OCC[N+](C)(C)C.[Cl-]
• Canonical SMILES: O=C(CCSS(=O)(=O)C)OCC[N+](C)(C)C.[Cl-]
• InChI: InChI=1S/C9H20NO4S2.ClH/c1-10(2,3)6-7-14-9(11)5-8-15-16(4,12)13;/h5-8H2,1-4H3;1H/q+1;/p-1
• InChIKey: VCRCFGIRTQZWDC-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{[3-(methanesulfonylsulfanyl)propanoyl]oxy}ethyl)trimethylazanium chloride
• IUPAC Traditional name: (2-{[3-(methanesulfonylsulfanyl)propanoyl]oxy}ethyl)trimethylazanium chloride
• Synonyms: N,N,N-Trimethyl-2-[3-[(methylsulfonyl)thio]-1-oxopropoxy]ethanaminium Chloride; 2-Carboxyethyl Methanethiosulfonate, Choline Ester Chloride Salt

Database IDs

• CAS Number: 1219378-82-1
• PubChem SID: 162257876
• PubChem CID: 71314541

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -4.3702707
• LogD (pH = 7.4): -4.3702707
• Log P: -4.3702707
• Molar Refractivity: 76.9985 cm^3
• Polarizability: 26.920288 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol; Water
• Apperance: Whgite Solid
• Melting Point: 126-127°C

DETAILS

Toronto Research Chemicals - C178130

Reacts specifically and rapidly with thiols to form mixed disulfides. Used to probe the structures of the ACh receptor channel of the GABA receptor channel and of lactose permease.

REFERENCES

• Xu, M. & Akabus, M.H.: J. Biol. Chem., 268, 21505 (1993)
• Duhten, R.L., et al.: Biochemistry, 32, 3139 (1993)
• Yang, N. et al.: Neuron, 16, 113 (1993)
• Kuner, T. et al.: Neuron, 17, 343 (1996)