8-{[2-(2-iodoacetamido)ethyl]amino}naphthalene-1-sulfonic acid

• ChemBase ID: 132164
• Molecular Formular: C14H15IN2O4S
• Molecular Mass: 434.24937
• Monoisotopic Mass: 433.97972597
• SMILES: c1cc2cccc(c2c(c1)NCCNC(=O)CI)S(=O)(=O)O
• Canonical SMILES: ICC(=O)NCCNc1cccc2c1c(ccc2)S(=O)(=O)O
• InChI: InChI=1S/C14H15IN2O4S/c15-9-13(18)17-8-7-16-11-5-1-3-10-4-2-6-12(14(10)11)22(19,20)21/h1-6,16H,7-9H2,(H,17,18)(H,19,20,21)
• InChIKey: ZDIHEEHLFMMPKM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-{[2-(2-iodoacetamido)ethyl]amino}naphthalene-1-sulfonic acid
• IUPAC Traditional name: 8-{[2-(2-iodoacetamido)ethyl]amino}naphthalene-1-sulfonic acid
• Synonyms: 1,8-I-AEDANS; N-Iodoacetyl-N′-(8-sulfo-1-naphthyl)ethylenediamine; N-(Iodoacetamidoethyl)-1-aminonaphthalene-8-sulfonic Acid; N-(Iodoacetylaminoethyl)-8-naphthylamine-1-sulfonic Acid; 8-[2-(2-碘乙酰氨基)乙氨基]-1-萘磺酸; N-碘乙酰基-N′-(8-磺基-1-萘基)乙二胺

Database IDs

• CAS Number: 36930-64-0
• EC Number: 253-278-2
• MDL Number: MFCD00003999
• PubChem SID: 24896147; 162226441
• PubChem CID: 93196

CALCULATED PROPERTIES

• Acid pKa: -2.1854463
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.60194427
• LogD (pH = 7.4): -0.7895423
• Log P: 1.0491902
• Molar Refractivity: 93.8019 cm^3
• Polarizability: 37.15526 Å^3
• Polar Surface Area: 95.5 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: At least 0.05M in phosphate buffer at pH 7 DMF; DMSO
• Apperance: Tan Solid; yellow crystalline
• Melting Point: 186-188°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Sensitive to Light
• German water hazard class: 3

DETAILS

Toronto Research Chemicals - I685605

A fluorescent sulfhydryl reagent which is sensitive to photo catalyzed degradation in both aqueous solution and organic solvents. It readily reacts with both thiol compounds and sulfhydryl groups to provide photo stable covalent derivatives.

REFERENCES

• Hudson, E.N. and Weber, G.: Biochem, 12(21)
• 4154-4161 (1973)