3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ4-chromen-1-ylium chloride

• ChemBase ID: 165058
• Molecular Formular: C21H19ClO12
• Molecular Mass: 498.82136
• Monoisotopic Mass: 498.05650373
• SMILES: c1(cc(c2c(c1)[o+]c(c(c2)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)c1ccc(c(c1)O)O)O)O.[Cl-]
• Canonical SMILES: Oc1cc(O)c2c(c1)[o+]c(c(c2)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O)c1ccc(c(c1)O)O.[Cl-]
• InChI: InChI=1S/C21H18O12.ClH/c22-8-4-11(24)9-6-14(32-21-17(28)15(26)16(27)19(33-21)20(29)30)18(31-13(9)5-8)7-1-2-10(23)12(25)3-7;/h1-6,15-17,19,21,26-28H,(H4-,22,23,24,25,29,30);1H/t15-,16-,17+,19-,21+;/m0./s1
• InChIKey: ZVTDPGYQESCLRY-ZKWAOETCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: 3-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ^4-chromen-1-ylium chloride
• Synonyms: 2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranuronosyloxy)-5,7-dihydroxy-1-benzopyrylium Chloride; Cyanidin 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 683208-13-1
• PubChem SID: 162259191
• PubChem CID: 71315020

CALCULATED PROPERTIES

• Acid pKa: 3.3500137
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -1.3969833
• LogD (pH = 7.4): -4.058915
• Log P: 0.7963
• Molar Refractivity: 116.1249 cm^3
• Polarizability: 43.972534 Å^3
• Polar Surface Area: 210.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C953670

Cyanidin 3-O-β-D-Glucuronide is an anthocyanin metabolite of Cyanidin.

REFERENCES

• Lietti, A., et al.: Arzneim.-Forsch., 26, 829 (1976)
• Kamei, H., et al.: Cancer Invest., 13, 590 (1976)
• Wang, H., et al.: J. Agric. Food Chem., 45, 304 (1976)
• O'Leary, K., et al.: Biochem. Pharmacol., 65, 479 (1976)