tert-butyl 2-{bis[2-(tert-butoxy)-2-oxoethyl]amino}-6-[3-(methanesulfonylsulfanyl)propanamido]hexanoate

• ChemBase ID: 168654
• Molecular Formular: C26H48N2O9S2
• Molecular Mass: 596.79732
• Monoisotopic Mass: 596.28012313
• SMILES: CS(=O)(=O)SCCC(=O)NCCCCC(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(=O)OC(C)(C)C
• Canonical SMILES: O=C(CCSS(=O)(=O)C)NCCCCC(C(=O)OC(C)(C)C)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C
• InChI: InChI=1S/C26H48N2O9S2/c1-24(2,3)35-21(30)17-28(18-22(31)36-25(4,5)6)19(23(32)37-26(7,8)9)13-11-12-15-27-20(29)14-16-38-39(10,33)34/h19H,11-18H2,1-10H3,(H,27,29)
• InChIKey: SGVBCCGPNWYRGM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-{bis[2-(tert-butoxy)-2-oxoethyl]amino}-6-[3-(methanesulfonylsulfanyl)propanamido]hexanoate
• IUPAC Traditional name: tert-butyl 2-{bis[2-(tert-butoxy)-2-oxoethyl]amino}-6-[3-(methanesulfonylsulfanyl)propanamido]hexanoate
• Synonyms: Ethylmethanethiosulfonate-2-carboxy[(5'-amino-1'-carboxypentyl)iminodiacetic Acid] Amide Tri-tert-butyl ester

Database IDs

• PubChem SID: 162262786
• PubChem CID: 45039214

CALCULATED PROPERTIES

• Acid pKa: 15.0953455
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 2.329956
• LogD (pH = 7.4): 2.3302598
• Log P: 2.3302636
• Molar Refractivity: 150.8689 cm^3
• Polarizability: 61.06757 Å^3
• Polar Surface Area: 145.38 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Slightly Yellow Oil

DETAILS

Toronto Research Chemicals - E925025

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)