sodium 5-carboxy-2-[(1E,3E,5E)-7-[(2E)-5-carboxy-3,3-dimethyl-1-(4-sulfonatobutyl)-2,3-dihydro-1H-indol-2-ylidene]hepta-1,3,5-trien-1-yl]-3,3-dimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium

• ChemBase ID: 162412
• Molecular Formular: C37H43N2NaO10S2
• Molecular Mass: 762.86449
• Monoisotopic Mass: 762.22568187
• SMILES: c1cc(cc2c1[N+](=C(C2(C)C)/C=C/C=C/C=C/C=C/1\C(c2c(N1CCCCS(=O)(=O)[O-])ccc(c2)C(=O)O)(C)C)CCCCS(=O)(=O)[O-])C(=O)O.[Na+]
• Canonical SMILES: OC(=O)c1ccc2c(c1)C(C)(C)/C(=C\C=C\C=C\C=C\C1=[N+](CCCCS(=O)(=O)[O-])c3c(C1(C)C)cc(cc3)C(=O)O)/N2CCCCS(=O)(=O)[O-].[Na+]
• InChI: InChI=1S/C37H44N2O10S2.Na/c1-36(2)28-24-26(34(40)41)16-18-30(28)38(20-10-12-22-50(44,45)46)32(36)14-8-6-5-7-9-15-33-37(3,4)29-25-27(35(42)43)17-19-31(29)39(33)21-11-13-23-51(47,48)49;/h5-9,14-19,24-25H,10-13,20-23H2,1-4H3,(H3-,40,41,42,43,44,45,46,47,48,49);/q;+1/p-1
• InChIKey: RKUODBYIZYLIDP-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 5-carboxy-2-[(1E,3E,5E)-7-[(2E)-5-carboxy-3,3-dimethyl-1-(4-sulfonatobutyl)-2,3-dihydro-1H-indol-2-ylidene]hepta-1,3,5-trien-1-yl]-3,3-dimethyl-1-(4-sulfonatobutyl)-3H-indol-1-ium
• IUPAC Traditional name: sodium 5-carboxy-2-[(1E,3E,5E)-7-[(2E)-5-carboxy-3,3-dimethyl-1-(4-sulfonatobutyl)indol-2-ylidene]hepta-1,3,5-trien-1-yl]-3,3-dimethyl-1-(4-sulfonatobutyl)indol-1-ium
• Synonyms: 5-Carboxy-2-[7-[5-carboxy-1,3-dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-1,3,5-heptatrien-1-yl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium Monosodium Salt; NIR 96005; 1,1'-Bis-(4-sulfobutyl)-indotricarbocyanine-5,5'-dicarboxylic Acid Monosodium Salt;

Database IDs

• CAS Number: 308127-43-7
• PubChem SID: 162256547
• PubChem CID: 71314110

CALCULATED PROPERTIES

• Acid pKa: -1.2293676
• H Acceptors: 11
• H Donor: 2
• LogD (pH = 5.5): -0.65559655
• LogD (pH = 7.4): -3.9165168
• Log P: 3.6164486
• Molar Refractivity: 210.4951 cm^3
• Polarizability: 75.68873 Å^3
• Polar Surface Area: 195.25 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Dark Yellow Powder

DETAILS

Toronto Research Chemicals - B535140

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)