1-(3-carboxypropyl)-11-ethyl-2,2-dimethyl-4-(sulfonatomethyl)-2,8,9,10-tetrahydro-1H-13-oxa-1,6,11-triazapentacen-11-ium

• ChemBase ID: 155878
• Molecular Formular: C27H31N3O6S
• Molecular Mass: 525.61654
• Monoisotopic Mass: 525.19335673
• SMILES: CC[N+]1=c2cc3c(=Nc4cc5c(cc4O3)N(C(C=C5CS(=O)(=O)[O-])(C)C)CCCC(=O)O)cc2CCC1
• Canonical SMILES: CC[N+]1=c2cc3Oc4cc5c(cc4N=c3cc2CCC1)C(=CC(N5CCCC(=O)O)(C)C)CS(=O)(=O)[O-]
• InChI: InChI=1S/C27H31N3O6S/c1-4-29-9-5-7-17-11-20-24(13-22(17)29)36-25-14-23-19(12-21(25)28-20)18(16-37(33,34)35)15-27(2,3)30(23)10-6-8-26(31)32/h11-15H,4-10,16H2,1-3H3,(H-,31,32,33,34,35)
• InChIKey: MHHMNDJIDRZZNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-carboxypropyl)-11-ethyl-2,2-dimethyl-4-(sulfonatomethyl)-2,8,9,10-tetrahydro-1H-13-oxa-1,6,11-triazapentacen-11-ium
• IUPAC Traditional name: 11-(3-carboxypropyl)-1-ethyl-10,10-dimethyl-8-(sulfonatomethyl)-3,4-dihydro-2H-13-oxa-1,6,11-triazapentacen-1-ium
• Synonyms: Atto 680

Database IDs

• MDL Number: MFCD03456138
• PubChem SID: 162250016
• PubChem CID: 16218800

CALCULATED PROPERTIES

• Acid pKa: -1.0046121
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 0.19374092
• LogD (pH = 7.4): -1.4314735
• Log P: -0.010415799
• Molar Refractivity: 156.211 cm^3
• Polarizability: 54.03002 Å^3
• Polar Surface Area: 122.34 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 680 nm; λem 695 nm in 0.1 M phosphate pH 7.0

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent

DETAILS

Sigma Aldrich - 94875

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 680 shows a molar extinction of 120,000 and QY of 30% in water (40% in ethanol). Decay time is 1.8 ns.
Other Notes
New red absorbing fluorescent dye as a biophysical probe for binding interactions;1,2 used as fluorescence tracer in spray diagnostics.3