9-cyano-3-(diethylamino)-6-({6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}(ethyl)amino)-10λ4-xanthen-10-ylium chloride

• ChemBase ID: 133522
• Molecular Formular: C30H35ClN4O5
• Molecular Mass: 567.0757
• Monoisotopic Mass: 566.22959792
• SMILES: CCN(CC)c1ccc2c(c1)[o+]c1cc(ccc1c2C#N)N(CC)CCCCCC(=O)ON1C(=O)CCC1=O.[Cl-]
• Canonical SMILES: CCN(c1ccc2c(c1)[o+]c1c(c2C#N)ccc(c1)N(CC)CC)CCCCCC(=O)ON1C(=O)CCC1=O.[Cl-]
• InChI: InChI=1S/C30H35N4O5.ClH/c1-4-32(5-2)21-11-13-23-25(20-31)24-14-12-22(19-27(24)38-26(23)18-21)33(6-3)17-9-7-8-10-30(37)39-34-28(35)15-16-29(34)36;/h11-14,18-19H,4-10,15-17H2,1-3H3;1H/q+1;/p-1
• InChIKey: FSUOQVGBXADQGH-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-cyano-3-(diethylamino)-6-({6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}(ethyl)amino)-10λ^4-xanthen-10-ylium chloride
• IUPAC Traditional name: 9-cyano-3-(diethylamino)-6-({6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}(ethyl)amino)-10λ^4-xanthen-10-ylium chloride
• Synonyms: NIR-1; 9-Cyano-N,N,N′-triethylpyronine-N′-caproic acid N-hydroxysuccinimide ester chloride; N,N,N-Triethyl-N-[5-(N-succinimidyloxycarbonyl)pentyl]-9-cyanopyronine chloride; NIR-667 NHS ester; NIR-667 N-succinimidyl ester

Database IDs

• CAS Number: 151134-79-1; 158358-57-7
• MDL Number: MFCD01310495
• PubChem SID: 162227799; 24889563
• PubChem CID: 2763061

CALCULATED PROPERTIES

• Acid pKa: 17.709124
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 5.4201784
• LogD (pH = 7.4): 5.420279
• Log P: 5.4202805
• Molar Refractivity: 150.7334 cm^3
• Polarizability: 58.75793 Å^3
• Polar Surface Area: 107.09 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 667 nm; λem 685 nm in acetonitrile

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C30H35ClN4O5

DETAILS

Sigma Aldrich - 91815

Other Notes
Near IR fluorescent probe used for amino acid detection (λex: 667 nm, λem 690 nm) by capillary in atto-mol level by electrophoresis. Amino and sulfhydryl reactive water-soluble label1

Sigma Aldrich - C6331

Application
Fluorescent label for amino acids allows for detection of alanine, arginine, glycine, glutamic and aspartic acid in the 0.8-4.5 × 10-18 M range.