3-(methanesulfonylsulfanyl)-N-(pyren-1-yl)propanamide

• ChemBase ID: 154081
• Molecular Formular: C20H17NO3S2
• Molecular Mass: 383.48388
• Monoisotopic Mass: 383.06498541
• SMILES: CS(=O)(=O)SCCC(=O)Nc1ccc2ccc3cccc4c3c2c1cc4
• Canonical SMILES: O=C(Nc1ccc2c3c1ccc1c3c(cc2)ccc1)CCSS(=O)(=O)C
• InChI: InChI=1S/C20H17NO3S2/c1-26(23,24)25-12-11-18(22)21-17-10-8-15-6-5-13-3-2-4-14-7-9-16(17)20(15)19(13)14/h2-10H,11-12H2,1H3,(H,21,22)
• InChIKey: URZKUTILUPDOKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(methanesulfonylsulfanyl)-N-(pyren-1-yl)propanamide
• IUPAC Traditional name: 3-(methanesulfonylsulfanyl)-N-(pyren-1-yl)propanamide
• Synonyms: Methanesulfonothioic acid S-[3-oxo-3-(1-pyrenylamino)propyl] ester; 2-(1-Pyrenylaminocarbonyl)ethyl methanethiosulfonate; Pyrene-ACE-MTS; 2-(Pyren-1-ylaminocarbonyl)ethyl Methanethiosulfonate

Database IDs

• CAS Number: 384342-64-7
• MDL Number: MFCD01320456
• PubChem SID: 162248220
• PubChem CID: 4624319

CALCULATED PROPERTIES

• Acid pKa: 13.396047
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.372511
• LogD (pH = 7.4): 3.3725104
• Log P: 3.372511
• Molar Refractivity: 107.2386 cm^3
• Polarizability: 45.351776 Å^3
• Polar Surface Area: 63.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: Light Yellow-Green Solid
• Melting Point: 171-173°C
• Fluorescence: λex 348 nm; λem 384 nm in 0.1 M phosphate pH 7.0

Safety Information

• Storage Warning: Moisture, Light Sensitive
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (TLC)
• Grade: for fluorescence
• Suitability: corresponds for coupling to thiols
• Empirical Formula (Hill Notation): C20H17NO3S2

DETAILS

Toronto Research Chemicals - P989750

A fluorescent compound used for the rapid and selective modification of sulfhydryl groups of enzymes.

REFERENCES

• Stauffer, D.A., and Karlin, A.: Biochemistry, 33, 6840 (1994)
• Yang, N. et al.: Neuron, 16, 113 (1994)
• Kuner, T. et al.: Neuron, 17, 343 (1996)