(2Z)-3-({3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-yl}carbamoyl)prop-2-enoic acid

• ChemBase ID: 169047
• Molecular Formular: C24H15NO8
• Molecular Mass: 445.3778
• Monoisotopic Mass: 445.07976645
• SMILES: c1(cc2c(cc1)C1(c3c(O2)cc(cc3)O)c2c(cc(cc2)NC(=O)/C=C\C(=O)O)C(=O)O1)O
• Canonical SMILES: OC(=O)/C=C\C(=O)Nc1ccc2c(c1)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)O)O
• InChI: InChI=1S/C24H15NO8/c26-13-2-5-17-19(10-13)32-20-11-14(27)3-6-18(20)24(17)16-4-1-12(9-15(16)23(31)33-24)25-21(28)7-8-22(29)30/h1-11,26-27H,(H,25,28)(H,29,30)/b8-7-
• InChIKey: QNSPCTIVGNRMCN-FPLPWBNLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-3-({3',6'-dihydroxy-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-yl}carbamoyl)prop-2-enoic acid
• IUPAC Traditional name: (2Z)-3-({3',6'-dihydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-yl}carbamoyl)prop-2-enoic acid
• Synonyms: (2Z)-4-[(3',6'-Dihydroxy-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-5-yl)amino]-4-oxo-2-butenoic Acid; Fluoresceinamine Maleic Acid Monoamide

Database IDs

• CAS Number: 75900-74-2
• PubChem SID: 162263179
• PubChem CID: 10863193

CALCULATED PROPERTIES

• Acid pKa: 2.5245662
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.43125725
• LogD (pH = 7.4): -0.23029561
• Log P: 3.3004847
• Molar Refractivity: 118.0464 cm^3
• Polarizability: 43.32246 Å^3
• Polar Surface Area: 142.39 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - F485335

Intermediate in the production of fluorescent labeling reagents

REFERENCES

• Li, J., et al.: Bioorg. Med. Chem. Lett., 15, 5558 (2005)