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

• ChemBase ID: 176252
• Molecular Formular: C21H21ClO10
• Molecular Mass: 468.83844
• Monoisotopic Mass: 468.08232455
• SMILES: c1(cc(c2c(c1)[o+]c(c(c2)O[C@H]1OC([C@H](C([C@@H]1O)O)O)CO)c1ccc(cc1)O)O)O.[Cl-]
• Canonical SMILES: OCC1O[C@H](Oc2cc3c(O)cc(cc3[o+]c2c2ccc(cc2)O)O)[C@H](C([C@@H]1O)O)O.[Cl-]
• InChI: InChI=1S/C21H20O10.ClH/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9;/h1-7,16-19,21-22,26-28H,8H2,(H2-,23,24,25);1H/t16?,17-,18?,19-,21+;/m1./s1
• InChIKey: CAHGSEFWVUVGGL-XWJIBMMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2R,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2R,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• Synonyms: 3-(β-D-Galactopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyryliumChloride; 3-(Galactosyloxy)-4',5,7-trihydroxyflavylium Chloride; Pelargonidin 3-Galactoside; Pelargonidin 3-β-D-Galactoside

Database IDs

• CAS Number: 34425-22-4
• PubChem SID: 164232162
• PubChem CID: 46782687

CALCULATED PROPERTIES

• Acid pKa: 6.396818
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 0.6192396
• LogD (pH = 7.4): -0.59826374
• Log P: 0.6714
• Molar Refractivity: 114.2766 cm^3
• Polarizability: 43.362774 Å^3
• Polar Surface Area: 173.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P218510

A galactoside of Pelargonidin. A naturally occurring anthocyanin which was tested for cell proliferation inhibitory activity against human cancer cell lines.

REFERENCES

• Hertog, M., et al.: Lancet, 342, 1007 (1993)
• Frankel, E., et al.: J. Agric. Food Chem., 43, 890 (1993)
• Rackova, L., et al.: Bioorg. Med. Chem., 13, 6477 (1993)
• Amic, D., et al.: Curr. Med. Chem., 14, 827 (1993)
• Ray, S., et al.: Cent. Eur. J. Chem., 6,