6'-(acetyloxy)-4-amino-2',7'-difluoro-5-(methylamino)-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3'-yl acetate

• ChemBase ID: 154566
• Molecular Formular: C25H18F2N2O7
• Molecular Mass: 496.4164264
• Monoisotopic Mass: 496.10820737
• SMILES: CC(=O)Oc1cc2c(cc1F)C1(c3ccc(c(c3C(=O)O1)N)NC)c1cc(c(cc1O2)OC(=O)C)F
• Canonical SMILES: CNc1ccc2c(c1N)C(=O)OC12c2cc(F)c(cc2Oc2c1cc(F)c(c2)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C25H18F2N2O7/c1-10(30)33-20-8-18-13(6-15(20)26)25(12-4-5-17(29-3)23(28)22(12)24(32)36-25)14-7-16(27)21(34-11(2)31)9-19(14)35-18/h4-9,29H,28H2,1-3H3
• InChIKey: BEVHTVRRVVEMEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6'-(acetyloxy)-4-amino-2',7'-difluoro-5-(methylamino)-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-3'-yl acetate
• IUPAC Traditional name: 6'-(acetyloxy)-4-amino-2',7'-difluoro-5-(methylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl acetate
• Synonyms: 4-Amino-5-(N-methylamin)-3′,6′-bis(acetyloxy); 4-Amino-5-(N-methylamino)-3′,6′-bis(acetyloxy)-2′,7′-difluoro-spiro[isobenzofuran-1(3H),9′-[9H]xanthen]-3-one; DAF-FM DA; Diaminofluorescein-FM diacetate; DAF-FM DA

Database IDs

• CAS Number: 254109-22-3
• MDL Number: MFCD16872050
• PubChem SID: 162248704
• PubChem CID: 2762646

CALCULATED PROPERTIES

• Acid pKa: 18.457483
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.2718992
• LogD (pH = 7.4): 3.2811325
• Log P: 3.2812514
• Molar Refractivity: 124.8501 cm^3
• Polarizability: 45.72217 Å^3
• Polar Surface Area: 126.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white to off-white powder
• Fluorescence: λex 500 nm; λem 515 nm in DMSO

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C25H18F2N2O7

DETAILS

Sigma Aldrich - D1946

Caution
Hygroscopic
Biochem/physiol Actions
DAF-FM DA is a cell-permeable fluorescent probe for the detection of nitric oxide (NO). DAF-2 is the original compound and is widely used, but DAF-FM and DAF-FM DA are more sensitive to nitric oxide (NO) compared with DAF-2 and more photo-stable and less pH sensitive. DAF-FM DA permeates well into living cells and is rapidly transformed into water-soluble DAF-FM by cytosolic esterases.