(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-[4-hydroxy-3-methoxy(2H3)phenyl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro(6,8-2H2)-2H-1-benzopyran-4-one

• ChemBase ID: 177767
• Molecular Formular: C25H22O10
• Molecular Mass: 482.43618
• Monoisotopic Mass: 482.1212969
• SMILES: c1c(c(cc(c1)[C@H]1Oc2c(O[C@@H]1CO)ccc(c2)[C@H]1Oc2c(C(=O)[C@@H]1O)c(cc(c2)O)O)OC)O
• Canonical SMILES: OC[C@H]1Oc2ccc(cc2O[C@@H]1c1ccc(c(c1)OC)O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
• InChI: InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
• InChIKey: SEBFKMXJBCUCAI-HKTJVKLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-[4-hydroxy-3-methoxy(^2H₃)phenyl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro(6,8-^2H₂)-2H-1-benzopyran-4-one
• IUPAC Traditional name: (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-[4-hydroxy-3-methoxy(^2H₃)phenyl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro(6,8-^2H₂)-1-benzopyran-4-one
• Synonyms: (2R,3R)-2-[(2R,3R)-2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-1-benzopyran-4-one-d5; Silibinin-d5; Silliver-d5; Silybin A-d5; Silybin b1-d5; Silybine-d5; Silymarin I-d5; Silymarin MZ 80-d5; Silymarine I-d5; Silybin-d5

Database IDs

• PubChem SID: 164233677
• PubChem CID: 71752198

CALCULATED PROPERTIES

• Acid pKa: 7.811773
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): 2.6272182
• LogD (pH = 7.4): 2.4878588
• Log P: 2.629316
• Molar Refractivity: 120.2939 cm^3
• Polarizability: 46.91771 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S465852

Labelled Silybin (S465850). Hepatoprotectant.

REFERENCES

• Xu, P., et al.: Int. J. Biol. Macromol., 47, 654 (2010)
• Ravichandran, K., et al.: Clin. Canc. Res., 16, 4595 (2010)
• Derbre, S., et al.: Anal. Bioanal. Chem., 398, 1747 (2010)