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

• ChemBase ID: 176416
• Molecular Formular: C22H23ClO12
• Molecular Mass: 514.86382
• Monoisotopic Mass: 514.08780386
• SMILES: c1(cc(c2c(c1)[o+]c(c(c2)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)c1cc(c(c(c1)OC)O)O)O)O.[Cl-]
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2cc(O)c(c(c2)OC)O)O)[C@H]([C@H]([C@@H]1O)O)O.[Cl-]
• InChI: InChI=1S/C22H22O12.ClH/c1-31-14-3-8(2-12(26)17(14)27)21-15(6-10-11(25)4-9(24)5-13(10)32-21)33-22-20(30)19(29)18(28)16(7-23)34-22;/h2-6,16,18-20,22-23,28-30H,7H2,1H3,(H3-,24,25,26,27);1H/t16-,18-,19+,20-,22-;/m1./s1
• InChIKey: HBKZHMZCXXQMOX-YATQZQGFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: petunidin 3-glucoside chloride
• Synonyms: 2-(3,4-dihydroxy-5-methoxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyrylium Chloride; 3-(Glucosyloxy)-3',4',5,7-tetrahydroxy-5'-methoxyflavylium Chloride; 3-(β-D-Glucopyranosyloxy)-3',4',5,7-tetrahydroxy-5'-methoxyflavylium Chloride; Petunidin 3-O-β-D-Glucopyranoside; Petunidin 3-Monoglucoside; Petunidin 3-β-D-Monoglucoside; Petunidin 3-O-β-D-Glucoside

Database IDs

• CAS Number: 6988-81-4
• PubChem SID: 164232326
• PubChem CID: 176449

CALCULATED PROPERTIES

• Acid pKa: 6.3943586
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): 0.08186768
• LogD (pH = 7.4): -1.1331584
• Log P: 0.1343
• Molar Refractivity: 122.7207 cm^3
• Polarizability: 46.563988 Å^3
• Polar Surface Area: 202.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P293610

Petunidin 3-O-β-D-Glucoside is a glycoside form of the O-methylated anthocyanidin, Petundin, which is present in grape as well as other fruits. Petunidin 3-O-β-D-Glucoside shows anti-oxidant activities as well as having potential cytoprotective effects.

REFERENCES

• Philip, T.: J. Food Sci., 39, 325 (1974)
• Choi, E.H. et al.: Food Chem. Toxicol., 45, 1873 (1974)
• Mane, C. et al.: J. Agric. Food Chem., 59, 3330 (1974)