5-[(2R)-2-amino-3-(methanesulfonylsulfanyl)propanamido]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid; trifluoroacetic acid

• ChemBase ID: 160151
• Molecular Formular: C26H21F3N2O10S2
• Molecular Mass: 642.5775496
• Monoisotopic Mass: 642.05897154
• SMILES: c1(ccc2c(c1)oc1c(c2c2ccc(cc2C(=O)O)NC(=O)[C@@H](N)CSS(=O)(=O)C)ccc(=O)c1)O.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.O=C([C@H](CSS(=O)(=O)C)N)Nc1ccc(c(c1)C(=O)O)c1c2ccc(=O)cc2oc2c1ccc(c2)O
• InChI: InChI=1S/C24H20N2O8S2.C2HF3O2/c1-36(32,33)35-11-19(25)23(29)26-12-2-5-15(18(8-12)24(30)31)22-16-6-3-13(27)9-20(16)34-21-10-14(28)4-7-17(21)22;3-2(4,5)1(6)7/h2-10,19,27H,11,25H2,1H3,(H,26,29)(H,30,31);(H,6,7)/t19-;/m0./s1
• InChIKey: NECZQSKRJXFCLU-FYZYNONXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2R)-2-amino-3-(methanesulfonylsulfanyl)propanamido]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid; trifluoroacetic acid
• IUPAC Traditional name: 5-[(2R)-2-amino-3-(methanesulfonylsulfanyl)propanamido]-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid; trifluoroacetic acid
• Synonyms: MTSEA-Fluorescein; (R)-2-Amino-2-[(5-fluoresceinyl)aminocarbonyl]ethyl Methanethiosulfonate, Trifluoroacetate Salt

Database IDs

• CAS Number: 1356019-48-1
• PubChem SID: 162254286
• PubChem CID: 71313256

CALCULATED PROPERTIES

• Acid pKa: 3.5701735
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.250499
• LogD (pH = 7.4): -2.3641102
• Log P: -1.2267007
• Molar Refractivity: 147.0347 cm^3
• Polarizability: 51.8657 Å^3
• Polar Surface Area: 173.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Yellow to Orange Solid
• Melting Point: >180°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A609615

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)