(2S)-5,7-dihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase ID: 177709
• Molecular Formular: C25H22O9
• Molecular Mass: 466.43678
• Monoisotopic Mass: 466.12638228
• SMILES: [C@H]1([C@H](Oc2c(O1)ccc(c2)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)CO)c1cc(c(cc1)O)OC
• Canonical SMILES: OC[C@H]1Oc2cc(ccc2O[C@@H]1c1ccc(c(c1)OC)O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
• InChI: InChI=1S/C25H22O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-9,19,23,25-29H,10-11H2,1H3/t19-,23+,25+/m0/s1
• InChIKey: CRPGUMMYQABYES-DNVKUUNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5,7-dihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC Traditional name: silandrin
• Synonyms: trans-(2R)-rel-2-[(2S,3S)-2,3-Dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one; rel-trans-Silandrin(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164233619
• PubChem CID: 441663

CALCULATED PROPERTIES

• Acid pKa: 7.9173727
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 3.3428285
• LogD (pH = 7.4): 3.2298343
• Log P: 3.3444746
• Molar Refractivity: 118.9557 cm^3
• Polarizability: 46.221992 Å^3
• Polar Surface Area: 134.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S431000

An antihepatotoxic flavanolignan as medicinal agent. It is used for the treatment of hepatic and biliary diseases.

REFERENCES

• Wagner, H., et al.: Arzneim.-Forsch., 24, 466 (1974)
• Hikino, H., et al.: Planta Med., 50, 248 (1974)
• Carini, R., et al.: Biochem. Pharmacol., 43, 2111 (1974)
• Scambia, G., et al.: Eur. J. Cancer, 32A, 877 (1974)
• Saller, R., et al.: Drugs, 61, 2035 (20