5-carboxy-2,3,3-trimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium

• ChemBase ID: 163793
• Molecular Formular: C16H21NO5S
• Molecular Mass: 339.40664
• Monoisotopic Mass: 339.11404378
• SMILES: c1(ccc2c(c1)C(C(=[N+]2CCCCS(=O)(=O)[O-])C)(C)C)C(=O)O
• Canonical SMILES: OC(=O)c1ccc2c(c1)C(C)(C)C(=[N+]2CCCCS(=O)(=O)[O-])C
• InChI: InChI=1S/C16H21NO5S/c1-11-16(2,3)13-10-12(15(18)19)6-7-14(13)17(11)8-4-5-9-23(20,21)22/h6-7,10H,4-5,8-9H2,1-3H3,(H-,18,19,20,21,22)
• InChIKey: TWFUKKLDNXMBDQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-carboxy-2,3,3-trimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium
• IUPAC Traditional name: 5-carboxy-2,3,3-trimethyl-1-(4-sulfonatobutyl)indol-1-ium
• Synonyms: 5-Carboxy-2,3,3-trimethyl-1-(4-sulfobutyl)-3H-indolium; 5-Carboxy-1-(4-sulfobutyl)-2,3,3-trimethyl-3H-indolium

Database IDs

• CAS Number: 852818-04-3
• PubChem SID: 162257928
• PubChem CID: 22717130

CALCULATED PROPERTIES

• Acid pKa: -1.0392509
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.88100696
• LogD (pH = 7.4): -2.37049
• Log P: -0.97591627
• Molar Refractivity: 97.108 cm^3
• Polarizability: 34.034676 Å^3
• Polar Surface Area: 97.51 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pink Powder

DETAILS

Toronto Research Chemicals - C182490

Intermediate in the synthesis of cyanine dyes for fluorescence imaging of tumor hypoxia and as contrast agents for near-IR tumor imaging.

REFERENCES

• Pavlik, C. et al.; Dyes Pigments 89, 9 (2010)
• Licha, K. et al.; Photochem. Photobiol. 72, 392 (2000)