7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-[3-hydroxy-4-(2H3)methoxyphenyl]-4H-chromen-4-one

• ChemBase ID: 175070
• Molecular Formular: C28H32O15
• Molecular Mass: 608.54468
• Monoisotopic Mass: 608.17412032
• SMILES: c1(cc(c2c(c1)oc(cc2=O)c1ccc(c(c1)O)OC)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)C)O)O)O)O)O)CO
• Canonical SMILES: OC[C@@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)OC)[C@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H32O15/c1-10-21(33)23(35)25(37)27(39-10)43-26-24(36)22(34)19(9-29)42-28(26)40-12-6-14(31)20-15(32)8-17(41-18(20)7-12)11-3-4-16(38-2)13(30)5-11/h3-8,10,19,21-31,33-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
• InChIKey: VCCNKWWXYVWTLT-CYZBKYQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-[3-hydroxy-4-(^2H₃)methoxyphenyl]-4H-chromen-4-one
• IUPAC Traditional name: 7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-[3-hydroxy-4-(^2H₃)methoxyphenyl]chromen-4-one
• Synonyms: 7-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one-d3; 4',5-Dihydroxylflavanone-7-O-α-L-rhamnosyl (1→2)-β-D-glucopyranoside-d3; Diosmetin-7-neohesperidoside-d3; Neodiosmin-d3

Database IDs

• PubChem SID: 164230980
• PubChem CID: 71750988

CALCULATED PROPERTIES

• Acid pKa: 8.475637
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -0.44343138
• LogD (pH = 7.4): -0.4779387
• Log P: -0.4429759
• Molar Refractivity: 142.3911 cm^3
• Polarizability: 56.486294 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N389942

Labelled analogue of Neodiosmin, a flavone glycoside isolated from C. aurantium. Neodiosmin along with other citrus flavonoids showed antiproliferative activities against several tumor and normal human cell lines.

REFERENCES

• Del Rio, J.A. et al.: Phytochemistry, 31, 723 (1992)
• Kawaii, S. et al.: Biosci. Biotechnol. Biochem., 63, 896 (1992)
• Manthey, J.A. et al.: J. Agric. Food Chem., 50, 5837 (1992)