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

• ChemBase ID: 165727
• Molecular Formular: C21H21ClO12
• Molecular Mass: 500.83724
• Monoisotopic Mass: 500.07215379
• SMILES: c1(cc(c2c(c1)[o+]c(c(c2)O[C@@H]1OC([C@H](C([C@H]1O)O)O)CO)c1cc(c(c(c1)O)O)O)O)O.[Cl-]
• Canonical SMILES: OCC1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2cc(O)c(c(c2)O)O)O)[C@@H](C([C@@H]1O)O)O.[Cl-]
• InChI: InChI=1S/C21H20O12.ClH/c22-6-15-17(28)18(29)19(30)21(33-15)32-14-5-9-10(24)3-8(23)4-13(9)31-20(14)7-1-11(25)16(27)12(26)2-7;/h1-5,15,17-19,21-22,28-30H,6H2,(H4-,23,24,25,26,27);1H/t15?,17-,18?,19+,21-;/m1./s1
• InChIKey: ZJWIIMLSNZOCBP-TUHOWTMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-3-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: 5,7-dihydroxy-3-{[(2S,3S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ^4-chromen-1-ylium chloride
• Synonyms: 3-(β-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1-benzopyrylium Chloride; Delphinidin 3-O-Glucoside; Delphinidol 3-Glucoside; Delphinin; Mirtillin; Delphinidin 3-β-D-Glucoside

Database IDs

• CAS Number: 6906-38-3
• PubChem SID: 162259860
• PubChem CID: 71315363

CALCULATED PROPERTIES

• Acid pKa: 6.3666096
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): 0.046554822
• LogD (pH = 7.4): -1.3650914
• Log P: 0.1026
• Molar Refractivity: 118.2384 cm^3
• Polarizability: 44.66953 Å^3
• Polar Surface Area: 213.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D230690

A metabolite of Delphinidin. A constituent of blue honeysuckle as to novel source for phenolic antioxidants. Antimicrobial.

REFERENCES

• Christensen, G., et al.: J. Clin. Microbiol., 22, 996 (1985)
• Middleton, E., et al.: Biochem. Pharmacol., 43, 1167 (1985)
• Fukumoto, L., et al.: J. Agric. Food Chem., 48, 3597 (1985)
• Lu, Y., et al.: Food Chem., 75, 197 (1985)