2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-1λ4-chromen-1-ylium chloride

• ChemBase ID: 165060
• Molecular Formular: C20H19ClO10
• Molecular Mass: 454.81186
• Monoisotopic Mass: 454.06667449
• SMILES: c12c(cc(c([o+]1)c1ccc(c(c1)O)O)OC1C([C@H]([C@@H](CO1)O)O)O)c(cc(c2)O)O.[Cl-]
• Canonical SMILES: Oc1cc(O)c2c(c1)[o+]c(c(c2)OC1OC[C@H]([C@@H](C1O)O)O)c1ccc(c(c1)O)O.[Cl-]
• InChI: InChI=1S/C20H18O10.ClH/c21-9-4-12(23)10-6-16(30-20-18(27)17(26)14(25)7-28-20)19(29-15(10)5-9)8-1-2-11(22)13(24)3-8;/h1-6,14,17-18,20,25-27H,7H2,(H3-,21,22,23,24);1H/t14-,17+,18?,20?;/m1./s1
• InChIKey: ORTBMTXABUAMJS-CRTITRSXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• Synonyms: 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(D-xylopyranosyloxy)-1-benzopyrylium Chloride; Cyanidin 3-Xyloside

Database IDs

• CAS Number: 29761-24-8
• PubChem SID: 162259193
• PubChem CID: 71315022

CALCULATED PROPERTIES

• Acid pKa: 6.388333
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 1.0062807
• LogD (pH = 7.4): -0.2693963
• Log P: 1.0595
• Molar Refractivity: 110.295 cm^3
• Polarizability: 41.51912 Å^3
• Polar Surface Area: 173.21 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C953700

An anthocyanin found in plums and berries which may have an important role in cancer therapy.

REFERENCES

• Bakowska-Barczak, A., et al.: J. Agric. Food Chem., 56, 9933 (2008)
• Tarko, T., et al.: Food Technol. Biotechnol., 47, 456 (2008)
• Borowska, E., et al.: Itali. J. Food Sci., 21, 197 (2008)
• Usenik, V., et al.: Food Chem., 114, 529 (2008)