9-(4-carboxy-2-carboxylatophenyl)-3,6-bis(dimethylamino)-10λ4-xanthen-10-ylium

• ChemBase ID: 163798
• Molecular Formular: C25H22N2O5
• Molecular Mass: 430.45258
• Monoisotopic Mass: 430.15287181
• SMILES: c1(ccc2c(c1)[o+]c1c(c2c2ccc(cc2C(=O)[O-])C(=O)O)ccc(c1)N(C)C)N(C)C
• Canonical SMILES: CN(c1ccc2c(c1)[o+]c1c(c2c2ccc(cc2C(=O)[O-])C(=O)O)ccc(c1)N(C)C)C
• InChI: InChI=1S/C25H22N2O5/c1-26(2)15-6-9-18-21(12-15)32-22-13-16(27(3)4)7-10-19(22)23(18)17-8-5-14(24(28)29)11-20(17)25(30)31/h5-13H,1-4H3,(H-,28,29,30,31)
• InChIKey: YMZMTOFQCVHHFB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-(4-carboxy-2-carboxylatophenyl)-3,6-bis(dimethylamino)-10λ^4-xanthen-10-ylium
• IUPAC Traditional name: 5-carboxytetramethylrhodamine
• Synonyms: 9-(2,4-Dicarboxyphenyl)-3,6-bis(dimethylamino)xanthylium; 5-TAMRA; 5-Carboxytetramethyl Rhodamine

Database IDs

• CAS Number: 91809-66-4
• PubChem SID: 162257933
• PubChem CID: 2762602

CALCULATED PROPERTIES

• Acid pKa: 3.2451289
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.5742774
• LogD (pH = 7.4): -1.3511802
• Log P: 5.193772
• Molar Refractivity: 135.9569 cm^3
• Polarizability: 49.045753 Å^3
• Polar Surface Area: 97.05 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C183150

A long-wavelength dye.

REFERENCES

• Singleton, D., et al.: J. Med. Chem., 50, 2931 (2007)
• Dose, C., et al.: Bioorg. Med. Chem., 16, 65 (2007)