6-amino-9-[2-(methoxycarbonyl)phenyl]-3H-xanthen-3-iminium chloride

• ChemBase ID: 177504
• Molecular Formular: C21H17ClN2O3
• Molecular Mass: 380.82428
• Monoisotopic Mass: 380.09277009
• SMILES: c1(=[NH2+])ccc2c(c1)oc1c(c2c2c(cccc2)C(=O)OC)ccc(c1)N.[Cl-]
• Canonical SMILES: COC(=O)c1ccccc1c1c2ccc(=[NH2+])cc2oc2c1ccc(c2)N.[Cl-]
• InChI: InChI=1S/C21H16N2O3.ClH/c1-25-21(24)15-5-3-2-4-14(15)20-16-8-6-12(22)10-18(16)26-19-11-13(23)7-9-17(19)20;/h2-11,22H,23H2,1H3;1H
• InChIKey: MYFATKRONKHHQL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-amino-9-[2-(methoxycarbonyl)phenyl]-3H-xanthen-3-iminium chloride
• IUPAC Traditional name: rhodamine 123(1+) chloride
• Synonyms: 3,6-Diamino-9-[2-(methoxycarbonyl)phenyl]xanthylium Chloride; 2-(6-Amino-3-imino-3H-xanthen-9-yl)benzoic Acid Methyl Ester Monohydrochloride; R 22420; R 302; RH 123; Rhodamine-123

Database IDs

• CAS Number: 62669-70-9
• PubChem SID: 164233414
• PubChem CID: 65217

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.67261815
• LogD (pH = 7.4): 2.3732333
• Log P: 2.8461912
• Molar Refractivity: 124.1732 cm^3
• Polarizability: 37.94292 Å^3
• Polar Surface Area: 87.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R318585

Rhodamine-123 is a fluorescent dye most commonly used in flow cytometry as functional reporter for Pgp. Rhodamine 123 (R123), as a typical of P-glycoprotein substrate, was widely used to quantify P-glycoprotein (P-gp) functional efflux activity in vivo. R

REFERENCES

• Romiti, N., et al.: Toxicol. Appl. Pharmacol., 183, 83 (1999)
• Mizuno, N., et al.: Pharmacol. Rev., 559, 425 (1999)
• del Amo, E., et al.: Eur. J. Pharm. Sci., 36, 200 (1999)
• Yumoto, R., et al.: J. Pharmacol. Exp. Ther., 289, 149 (1999)