2-[bis(carboxymethyl)amino]-6-[3-(methanesulfonylsulfanyl)propanamido]hexanoic acid; trifluoroacetic acid

• ChemBase ID: 168653
• Molecular Formular: C16H25F3N2O11S2
• Molecular Mass: 542.5017096
• Monoisotopic Mass: 542.08518629
• SMILES: CS(=O)(=O)SCCC(=O)NCCCCC(N(CC(=O)O)CC(=O)O)C(=O)O.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.O=C(CCSS(=O)(=O)C)NCCCCC(N(CC(=O)O)CC(=O)O)C(=O)O
• InChI: InChI=1S/C14H24N2O9S2.C2HF3O2/c1-27(24,25)26-7-5-11(17)15-6-3-2-4-10(14(22)23)16(8-12(18)19)9-13(20)21;3-2(4,5)1(6)7/h10H,2-9H2,1H3,(H,15,17)(H,18,19)(H,20,21)(H,22,23);(H,6,7)
• InChIKey: USJLZSNKSUGWGZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[bis(carboxymethyl)amino]-6-[3-(methanesulfonylsulfanyl)propanamido]hexanoic acid; trifluoroacetic acid
• IUPAC Traditional name: 2-[bis(carboxymethyl)amino]-6-[3-(methanesulfonylsulfanyl)propanamido]hexanoic acid; trifluoroacetic acid
• Synonyms: MTSCE-NTA; Ethylmethanethiosulfonate-2-carboxy[(5'-amino-1'-carboxypentyl)iminodiacetic Acid] Amide, Trifluoroacetic Acid Salt

Database IDs

• PubChem SID: 162262785
• PubChem CID: 71316635

CALCULATED PROPERTIES

• Acid pKa: 2.3001742
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -6.358726
• LogD (pH = 7.4): -10.738683
• Log P: -2.217732
• Molar Refractivity: 95.1448 cm^3
• Polarizability: 38.483795 Å^3
• Polar Surface Area: 178.38 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: Off-Whie Solid
• Melting Point: 75-80°C dec.

DETAILS

Toronto Research Chemicals - E925020

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)