pentapotassium 2-{6-[bis(carboxylatomethyl)amino]-5-(2-{2-[bis(carboxylatomethyl)amino]-5-methylphenoxy}ethoxy)-1-benzofuran-2-yl}-1,3-oxazole-5-carboxylate

• ChemBase ID: 130877
• Molecular Formular: C29H22K5N3O14
• Molecular Mass: 831.98818
• Monoisotopic Mass: 830.9287108
• SMILES: Cc1ccc(c(c1)OCCOc1cc2cc(oc2cc1N(CC(=O)[O-])CC(=O)[O-])c1ncc(o1)C(=O)[O-])N(CC(=O)[O-])CC(=O)[O-].[K+].[K+].[K+].[K+].[K+]
• Canonical SMILES: [O-]C(=O)CN(c1cc2oc(cc2cc1OCCOc1cc(C)ccc1N(CC(=O)[O-])CC(=O)[O-])c1ncc(o1)C(=O)[O-])CC(=O)[O-].[K+].[K+].[K+].[K+].[K+]
• InChI: InChI=1S/C29H27N3O14.5K/c1-15-2-3-17(31(11-24(33)34)12-25(35)36)20(6-15)43-4-5-44-21-7-16-8-22(28-30-10-23(46-28)29(41)42)45-19(16)9-18(21)32(13-26(37)38)14-27(39)40;;;;;/h2-3,6-10H,4-5,11-14H2,1H3,(H,33,34)(H,35,36)(H,37,38)(H,39,40)(H,41,42);;;;;/q;5*+1/p-5
• InChIKey: HQKWBBCTCLUGSX-UHFFFAOYSA-I

NAMES AND DATABASE IDS

Names

• IUPAC name: pentapotassium 2-{6-[bis(carboxylatomethyl)amino]-5-(2-{2-[bis(carboxylatomethyl)amino]-5-methylphenoxy}ethoxy)-1-benzofuran-2-yl}-1,3-oxazole-5-carboxylate
• IUPAC Traditional name: pentapotassium 2-{6-[bis(carboxylatomethyl)amino]-5-(2-{2-[bis(carboxylatomethyl)amino]-5-methylphenoxy}ethoxy)-1-benzofuran-2-yl}-1,3-oxazole-5-carboxylate
• Synonyms: 2-[6-[Bis(carboxymethyl)amino]-5-[2-[2-[bis(carboxymethyl)amino]-5-methylphenoxy]ethoxy]-2-benzofuranyl]-5-oxazolecarboxylic Acid Pentapotassium Salt; FURA-2 Pentapotassium Salt; Fura 2 pentapotassium salt

Database IDs

• CAS Number: 113694-64-7
• MDL Number: MFCD00083328
• PubChem SID: 24894731; 24850391; 162225155
• PubChem CID: 6098363

CALCULATED PROPERTIES

• Acid pKa: 2.813001
• H Acceptors: 15
• H Donor: 0
• LogD (pH = 5.5): -6.8654613
• LogD (pH = 7.4): -14.359749
• Log P: 1.7244366
• Molar Refractivity: 217.159 cm^3
• Polarizability: 58.575737 Å^3
• Polar Surface Area: 264.76 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Fluorescence: λex 355 nm; λem 495 nm in 0.1 M Tris pH 8.0, Ca2+

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: ≥80%; ≥95% (TLC)
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C29H22K5N3O14

DETAILS

Sigma Aldrich - 17195

Other Notes
A very sensitive fluorescent calcium chelator that exhibits a spectral shift in excitation maxima on binding calcium1,2

Sigma Aldrich - F0763

Application
Cell impermeable fluorescent probe for Ca2+.

Toronto Research Chemicals - F822500

A cell impermeable fluorescent probe for magnesium.

REFERENCES

• Grynkiewicz, G., et al.: J. Biol. Chem., 260, 3440 (1985)