2-[(1E,3E)-5-[(2Z)-5-[(2-iodoacetamido)methyl]-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]penta-1,3-dien-1-yl]-1,1-dimethyl-3-(4-sulfonatobutyl)-1H-benzo[e]indol-3-ium

• ChemBase ID: 175021
• Molecular Formular: C37H42IN3O4S
• Molecular Mass: 751.71655
• Monoisotopic Mass: 751.19407584
• SMILES: c1ccc2c(c1)c1c(cc2)[N+](=C(C1(C)C)/C=C/C=C/C=C\1/C(c2c(ccc(c2)CNC(=O)CI)N1C)(C)C)CCCCS(=O)(=O)[O-]
• Canonical SMILES: ICC(=O)NCc1ccc2c(c1)C(C)(C)/C(=C/C=C/C=C/C1=[N+](CCCCS(=O)(=O)[O-])c3c(C1(C)C)c1ccccc1cc3)/N2C
• InChI: InChI=1S/C37H42IN3O4S/c1-36(2)29-23-26(25-39-34(42)24-38)17-19-30(29)40(5)32(36)15-7-6-8-16-33-37(3,4)35-28-14-10-9-13-27(28)18-20-31(35)41(33)21-11-12-22-46(43,44)45/h6-10,13-20,23H,11-12,21-22,24-25H2,1-5H3,(H-,39,42,43,44,45)
• InChIKey: DSOHJESYBPIQMM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1E,3E)-5-[(2Z)-5-[(2-iodoacetamido)methyl]-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]penta-1,3-dien-1-yl]-1,1-dimethyl-3-(4-sulfonatobutyl)-1H-benzo[e]indol-3-ium
• IUPAC Traditional name: 2-[(1E,3E)-5-[(2Z)-5-[(2-iodoacetamido)methyl]-1,3,3-trimethylindol-2-ylidene]penta-1,3-dien-1-yl]-1,1-dimethyl-3-(4-sulfonatobutyl)benzo[e]indol-3-ium
• Synonyms: 2-[5-[1,3-Dihydro-5-[[(2-iodoacetyl)amino]methyl]-1,3,3-trimethyl-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1,1-dimethyl-3-(4-sulfobutyl)-1H-Benz[e]indolium Inner Salt; 4,5-Benzo-5′-(iodoacetaminomethyl)-1′,3,3,3′,3′-pentamethyl-1-(4-sulfobutyl)indodicarbocyanine; NIR-664-iodoacetamide

Database IDs

• CAS Number: 149021-66-9
• PubChem SID: 164230931
• PubChem CID: 6157999

CALCULATED PROPERTIES

• Acid pKa: -0.731327
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 6.057944
• LogD (pH = 7.4): 6.0580263
• Log P: 5.2013736
• Molar Refractivity: 210.0407 cm^3
• Polarizability: 76.492615 Å^3
• Polar Surface Area: 92.55 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N481500

A fluorescent dye used in the detection of thiols.

REFERENCES

• Le Guevel, X. et al.: J. Sol. State Chem., 184, 1545 (2011)
• Mank, A.J.G. et al.: Anal. Chem., 65, 2197 (2011)