(1-{[3-carboxy-4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]carbamoyl}-2-(methanesulfonylsulfanyl)ethyl)trimethylazanium bromide

• ChemBase ID: 169069
• Molecular Formular: C27H27BrN2O8S2
• Molecular Mass: 651.54588
• Monoisotopic Mass: 650.03921983
• SMILES: c12c(cc(cc1)O)oc1c(c2c2ccc(cc2C(=O)O)NC(=O)C(CSS(=O)(=O)C)[N+](C)(C)C)ccc(=O)c1.[Br-]
• Canonical SMILES: O=C(C([N+](C)(C)C)CSS(=O)(=O)C)Nc1ccc(c(c1)C(=O)O)c1c2ccc(=O)cc2oc2c1ccc(c2)O.[Br-]
• InChI: InChI=1S/C27H26N2O8S2.BrH/c1-29(2,3)22(14-38-39(4,35)36)26(32)28-15-5-8-18(21(11-15)27(33)34)25-19-9-6-16(30)12-23(19)37-24-13-17(31)7-10-20(24)25;/h5-13,22H,14H2,1-4H3,(H2-,28,30,31,32,33,34);1H
• InChIKey: MTSPFCJAYFFAKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1-{[3-carboxy-4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]carbamoyl}-2-(methanesulfonylsulfanyl)ethyl)trimethylazanium bromide
• IUPAC Traditional name: (1-{[3-carboxy-4-(3-hydroxy-6-oxoxanthen-9-yl)phenyl]carbamoyl}-2-(methanesulfonylsulfanyl)ethyl)trimethylazanium bromide
• Synonyms: MTSET-Fluorescein; (R)-2-[(5-Fluoresceinyl)aminocarbonyl]-2-trimethylammoniumethyl Methanethiosulfonate, BromideDiscontinued

Database IDs

• PubChem SID: 162263201
• PubChem CID: 71316797

CALCULATED PROPERTIES

• Acid pKa: 3.5693765
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.5662702
• LogD (pH = 7.4): -2.492823
• Log P: -2.2026954
• Molar Refractivity: 173.0176 cm^3
• Polarizability: 57.30837 Å^3
• Polar Surface Area: 147.07 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F510500

A thiol specific fluorescent probe useful for ion channel and protein topology research. The recently available MTS-fluorophores may find application in the real-time monitoring of conformational changes, since fluorophores coupled to introduced cysteine

REFERENCES

• Mannuzzu, L.M., et al.: Science, 271, 213 (1996)
• Goulett, C.C., et al.: JBC, 273, 45, 30012 (1996)
• Adams, C.M., et al.: JBC, 273, 46, 30204 (1998)