1-{3-[(methanesulfonylsulfanyl)methyl]-2,2,5,5-tetramethyl-2,5-dihydro(1-15N)-1H-pyrrol-1-yl}ethan-1-one

• ChemBase ID: 159485
• Molecular Formular: C12H21NO3S2
• Molecular Mass: 292.4234489
• Monoisotopic Mass: 292.09332043
• SMILES: C1=C(C([15N](C1(C)C)C(=O)C)(C)C)CSS(=O)(=O)C
• Canonical SMILES: CC(=O)[15N]1C(C)(C)C=C(C1(C)C)CSS(=O)(=O)C
• InChI: InChI=1S/C12H21NO3S2/c1-9(14)13-11(2,3)7-10(12(13,4)5)8-17-18(6,15)16/h7H,8H2,1-6H3/i13+1
• InChIKey: NHWXBVUAMMVKNN-KCKQSJSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[(methanesulfonylsulfanyl)methyl]-2,2,5,5-tetramethyl-2,5-dihydro(1-^1^5N)-1H-pyrrol-1-yl}ethan-1-one
• IUPAC Traditional name: 1-{3-[(methanesulfonylsulfanyl)methyl]-2,2,5,5-tetramethyl(1-^1^5N)pyrrol-1-yl}ethanone
• Synonyms: Methanesulfonothioic Acid S-[(1-Acetyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-(pyrrol-15N)-3-yl)methyl] Ester; 1-Acetyl-2,2,5,5-tetramethyl-Δ3-(pyrroline-15N)-3-methyl Methanethiosulfonate

Database IDs

• PubChem SID: 162253620
• PubChem CID: 71313004

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.5607545
• LogD (pH = 7.4): 0.5607563
• Log P: 0.5607563
• Molar Refractivity: 76.031 cm^3
• Polarizability: 30.401175 Å^3
• Polar Surface Area: 54.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A188602

A highly reactive thiol-specific spin-label analogue. A specific conformational probe of thiol site structure by virtue of its minimal rotational freedom and distance from the covalent disulfide linkage to the macromolecule under study.

REFERENCES

• Berengian, A., et al.: J. Biol. Chem., 274, 6305 (1999)
• Gross, A., et al.: Biochemistry, 38, 10324 (1999)
• Dobson, C., et al.: Nature, 426, 884 (1999)
• Dong, J., et al: Science, 308, 1023 (1999)