2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-1λ4-chromen-1-ylium chloride

• ChemBase ID: 165059
• Molecular Formular: C27H31ClO15
• Molecular Mass: 630.97904
• Monoisotopic Mass: 630.13514797
• SMILES: c1(cc(c2c(c1)[o+]c(c(c2)OC1C(C(C(C(O1)COC1C(C(C(C(O1)C)O)O)O)O)O)O)c1ccc(c(c1)O)O)O)O.[Cl-]
• Canonical SMILES: Oc1cc(O)c2c(c1)[o+]c(c(c2)OC1OC(COC2OC(C)C(C(C2O)O)O)C(C(C1O)O)O)c1ccc(c(c1)O)O.[Cl-]
• InChI: InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H
• InChIKey: ADZHXBNWNZIHIX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-1λ^4-chromen-1-ylium chloride
• Synonyms: Prunicyanin; Sambucin; Cyanidin 3-O-Rutinoside; 3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyrylium Chloride; Keracyanin; 3-O-Rutinosylcyanidin; 7,4'-Dihydroxyflavilium Chloride; Antirrhinin; Cyanidin 3-Rutinoside; Cyanidin 3-Rhamnoglucoside; Cyanidin 3-Rhamnosylglucoside; Cyanidol 3-Rhamnoglucoside; Cyaninoside; Meralop

Database IDs

• CAS Number: 18719-76-1
• PubChem SID: 162259192
• PubChem CID: 14034150

CALCULATED PROPERTIES

• Acid pKa: 6.388329
• H Acceptors: 15
• H Donor: 10
• LogD (pH = 5.5): -0.69731975
• LogD (pH = 7.4): -1.9730065
• Log P: -0.6441
• Molar Refractivity: 147.1271 cm^3
• Polarizability: 57.083138 Å^3
• Polar Surface Area: 252.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C953680

Cyanidin 3-O-Rutinoside retards absorption of carbohydrates by inhibition of α-glucosidase which may be useful as a potential inhibitor for prevention and treatment of diabetes mellitus.

REFERENCES

• Raptis, S., et al.: Exp Clin Endocrinol Diabetes 2001, 109, S265,,Ceriello, A; Diabetes 2005, 54, 1,,Chiasson, J; Endocr Pract 2006, 12, 25,,,Misra, A; J Clin Endocrinol Metab 2008, 93, S9