2-[(1E)-3-[(2E)-3,3-dimethyl-1-[4-({1-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,7,10-trioxa-4-azadodecan-12-yl}carbamoyl)butyl]-2,3-dihydro-1H-indol-2-ylidene]prop-1-en-1-yl]-1,3,3-trimethyl-3H-indol-1-ium

• ChemBase ID: 169583
• Molecular Formular: C43H63N4O9+
• Molecular Mass: 779.98172
• Monoisotopic Mass: 779.45950462
• SMILES: c1cccc2c1C(/C(=C\C=C\C1=[N+](c3c(cccc3)C1(C)C)C)/N2CCCCC(=O)NCCOCCOCCNCCO[C@@H]1C([C@H]([C@@H](C(O1)CO)O)O)O)(C)C
• Canonical SMILES: OCC1O[C@H](OCCNCCOCCOCCNC(=O)CCCCN2c3ccccc3C(/C/2=C\C=C\C2=[N+](C)c3c(C2(C)C)cccc3)(C)C)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C43H62N4O9/c1-42(2)30-13-6-8-15-32(30)46(5)35(42)17-12-18-36-43(3,4)31-14-7-9-16-33(31)47(36)23-11-10-19-37(49)45-22-25-54-28-27-53-24-20-44-21-26-55-41-40(52)39(51)38(50)34(29-48)56-41/h6-9,12-18,34,38-41,44,48,50-52H,10-11,19-29H2,1-5H3/p+1/t34?,38-,39+,40?,41+/m1/s1
• InChIKey: SSFADTFCQMBTSO-IHRPVSEJSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1E)-3-[(2E)-3,3-dimethyl-1-[4-({1-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,7,10-trioxa-4-azadodecan-12-yl}carbamoyl)butyl]-2,3-dihydro-1H-indol-2-ylidene]prop-1-en-1-yl]-1,3,3-trimethyl-3H-indol-1-ium
• IUPAC Traditional name: 2-[(1E)-3-[(2E)-3,3-dimethyl-1-[4-({1-[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1,7,10-trioxa-4-azadodecan-12-yl}carbamoyl)butyl]indol-2-ylidene]prop-1-en-1-yl]-1,3,3-trimethylindol-1-ium
• Synonyms: 2-[3-[1-[17-(α-D-Glucopyranosyloxy)-5-oxo-9,12-dioxa-6,15-diazaheptadec-1-yl]-1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene]-1-propen-1-yl]-1,3,3-trimethyl-3H-indolium; GB1-Cy3; GB1-Cyanine 3

Database IDs

• CAS Number: 1065004-53-6
• PubChem SID: 162263715
• PubChem CID: 71317042

CALCULATED PROPERTIES

• Acid pKa: 12.211102
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.1008856
• LogD (pH = 7.4): -1.6954386
• Log P: -0.024387592
• Molar Refractivity: 229.5722 cm^3
• Polarizability: 84.4479 Å^3
• Polar Surface Area: 165.22 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G265000

A novel fluorescent dye-labeled glucose bio-probe use in bio-imaging and drug screening.

REFERENCES

• Alberti, K., et al.: Diabetic Med., 15, 539 (1998)
• Cho, H., et al.: Science, 292, 1728 (1998)
• Minokoshi, Y., et al.: J. Biol. Chem., 278, 33609 (1998)