9-(2-{[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamoyl}ethyl)-N-ethyl-6-(ethylamino)-2,7-dimethyl-3H-xanthen-3-iminium perchlorate

• ChemBase ID: 153725
• Molecular Formular: C28H33ClN4O8
• Molecular Mass: 589.03662
• Monoisotopic Mass: 588.19869172
• SMILES: CCNc1cc2c(cc1C)c(c1cc(/c(=[NH+]/CC)/cc1o2)C)CCC(=O)NCCN1C(=O)C=CC1=O.[O-][Cl](=O)(=O)=O
• Canonical SMILES: [O-][Cl](=O)(=O)=O.CCNc1cc2oc3c/c(=[NH+]\CC)/c(cc3c(c2cc1C)CCC(=O)NCCN1C(=O)C=CC1=O)C
• InChI: InChI=1S/C28H32N4O4.ClHO4/c1-5-29-22-15-24-20(13-17(22)3)19(21-14-18(4)23(30-6-2)16-25(21)36-24)7-8-26(33)31-11-12-32-27(34)9-10-28(32)35;2-1(3,4)5/h9-10,13-16,29H,5-8,11-12H2,1-4H3,(H,31,33);(H,2,3,4,5)
• InChIKey: DGEQWOHLXNEPEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-(2-{[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl]carbamoyl}ethyl)-N-ethyl-6-(ethylamino)-2,7-dimethyl-3H-xanthen-3-iminium perchlorate
• IUPAC Traditional name: 9-(2-{[2-(2,5-dioxopyrrol-1-yl)ethyl]carbamoyl}ethyl)-N-ethyl-6-(ethylamino)-2,7-dimethylxanthen-3-iminium perchlorate
• Synonyms: Atto 520 maleimide

Database IDs

• PubChem SID: 162247864; 24850149
• PubChem CID: 25164073

CALCULATED PROPERTIES

• Acid pKa: 15.3465185
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2717911
• LogD (pH = 7.4): 2.2142866
• Log P: 2.2587552
• Molar Refractivity: 156.0282 cm^3
• Polarizability: 53.006382 Å^3
• Polar Surface Area: 101.71 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble; DMF: soluble; DMSO: soluble

Safety Information

• 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% (coupling rate)
• Grade: for fluorescence
• Suitability: passes test for fluorescence
• Empirical Formula (Hill Notation): C28H33ClN4O8

DETAILS

Sigma Aldrich - 16590

Application
Atto fluorescent labels are designed for high sensitivity applications, including single molecule detection. Atto labels have rigid structures that do not show any cis-trans-isomerization. Thus these labels display exceptional intensity with minimal spectral shift on conjugation.
Atto 520 maleimide utilized for labeling sulfhydryl (thiol) groups of proteins, especially cysteine residues, to fluorescently study changes in conformation, binding, and kinetics 1,2.