6'-hydroxy-5-nitro-3',9'a-dihydro-3H-spiro[2-benzofuran-1,9'-xanthene]-3,3'-dione

• ChemBase ID: 175157
• Molecular Formular: C20H11NO7
• Molecular Mass: 377.30384
• Monoisotopic Mass: 377.0535517
• SMILES: c1cc(cc2c1C1(C3C(=CC(=O)C=C3)O2)OC(=O)c2c1ccc(c2)[N+](=O)[O-])O
• Canonical SMILES: O=C1C=CC2C(=C1)Oc1c(C32OC(=O)c2c3ccc(c2)[N+](=O)[O-])ccc(c1)O
• InChI: InChI=1S/C20H11NO7/c22-11-2-5-15-17(8-11)27-18-9-12(23)3-6-16(18)20(15)14-4-1-10(21(25)26)7-13(14)19(24)28-20/h1-9,15,23H
• InChIKey: CVEKAMUQOOINBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6'-hydroxy-5-nitro-3',9'a-dihydro-3H-spiro[2-benzofuran-1,9'-xanthene]-3,3'-dione
• IUPAC Traditional name: 3'-hydroxy-5-nitro-8'aH-spiro[2-benzofuran-1,9'-xanthene]-3,6'-dione
• Synonyms: 3',6'-Dihydroxy-5-nitro-spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one; 5-Nitrofluorescein; Nitrofluorescein, Isomer 1

Database IDs

• CAS Number: 3326-35-0
• PubChem SID: 164231067
• PubChem CID: 4116632

CALCULATED PROPERTIES

• Acid pKa: 5.6820984
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.4922247
• LogD (pH = 7.4): 1.1059265
• Log P: 2.7097797
• Molar Refractivity: 99.0393 cm^3
• Polarizability: 36.02023 Å^3
• Polar Surface Area: 118.65 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Orange Cyrstalline Solid
• Melting Point: >300°C

Safety Information

• Storage Warning: Light and Moisture Sensitive

DETAILS

Toronto Research Chemicals - N495860

Fluorescent labeling reagent for proteins. Used in the fluorescent antibody technique for rapid identification of pathogens.

REFERENCES

• Riggs, H.J.L., et al.: Amer. J. Pathol., 34, 1081 (1958)
• Mann, K.G. and Fish, W.W., Methods in Enz., 26, 28 (1958)