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

• ChemBase ID: 179833
• Molecular Formular: C28H32O14
• Molecular Mass: 592.54528
• Monoisotopic Mass: 592.1792057
• SMILES: c12c(=O)cc(oc1cc(O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)O)O)O)cc2O)c1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H32O14/c1-11-21(31)23(33)25(35)27(39-11)38-10-19-22(32)24(34)26(36)28(42-19)40-14-7-15(29)20-16(30)9-17(41-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-9,11,19,21-29,31-36H,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
• InChIKey: YFVGIJBUXMQFOF-PJOVQGMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one; 5-hydroxy-2-(4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one
• Synonyms: Linarin; Acaciin; Buddleoflavonoloside; Linaric acid; Acacetin 7-rutinoside; Acaciin; Acacetin 7-O-rutinoside; Linarin

Database IDs

• CAS Number: 480-36-4
• PubChem SID: 164235743
• PubChem CID: 5317025

CALCULATED PROPERTIES

• Acid pKa: 7.3142147
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -0.14596741
• LogD (pH = 7.4): -0.48118073
• Log P: -0.13941059
• Molar Refractivity: 140.4102 cm^3
• Polarizability: 55.81208 Å^3
• Polar Surface Area: 214.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder

Pharmacology Properties

• Mechanism of Action: Aldose reductase inhibitor

Product Information

• Biological Source: Occurs in Linaria vulgaris, Robinia and Micromeria spp. and other plants
• Application(s): Antidiabetic

REFERENCES

• Robinson, R. et al., J.C.S., 1926, 128, 2344, (synth)
• Freudenberg, K. et al., Annalen, 1954, 587, 207, (Acacetin trioside)
• Shibata, S. et al., Yakugaku Zasshi, 1960, 80, 620; CA, 54, 21488, (pharmacol)
• Nakaoki, T. et al., CA, 1961, 55, 10803, (deriv)
• Massicot, J. et al., Bull. Soc. Chim. Fr., 1963, 2712, (pmr)
• Nogradi, M. et al., Chem. Ber., 1967, 100, 2783, (deriv)
• Wagner, H. et al., Chem. Ber., 1969, 102, 1445; 2083; 1970, 103, 851, (derivs)
• Khadzhai, Y. et al., Farmakol. Toksikol. (Moscow), 1969, 32, 451, (pharmacol)
• Bowie, J.H. et al., J.C.S.(B), 1969, 2, 89, (ms)
• Okigawa, M. et al., Tet. Lett., 1970, 2935, (deriv)
• Nevskaya, E.M. et al., Zh. Anal. Khim., 1972, 27, 1699, (use)
• Wagner, H. et al., Tet. Lett., 1976, 1799, (nmr)
• Gaydou, E.M. et al., Bull. Soc. Chim. Fr., 1978, 43, (synth, pmr, uv)