(2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl](1,2,4-13C3)butane-1,4-diol

• ChemBase ID: 177727
• Molecular Formular: C20H26O6
• Molecular Mass: 365.39480451
• Monoisotopic Mass: 365.18300307
• SMILES: c1c(C[13C@H]([C@H](Cc2ccc(c(c2)OC)O)[13CH2]O)[13CH2]O)cc(c(c1)O)OC
• Canonical SMILES: O[13CH2][13C@@H]([C@H](Cc1ccc(c(c1)OC)O)[13CH2]O)Cc1ccc(c(c1)OC)O
• InChI: InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16+/i11+1,12+1,15+1/m0/s1
• InChIKey: PUETUDUXMCLALY-JQGCDJRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl](1,2,4-^1^3C₃)butane-1,4-diol
• IUPAC Traditional name: (2R,3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl](1,2,4-^1^3C₃)butane-1,4-diol
• Synonyms: (2R,3R)-rel-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol-13C3; (R*,R*)-(±)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol-13C3; (R*,R*)-2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol-13C3; rac Secoisolariciresinol-13C3

Database IDs

• PubChem SID: 164233637
• PubChem CID: 71752174

CALCULATED PROPERTIES

• Acid pKa: 9.963199
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 2.3328462
• LogD (pH = 7.4): 2.331682
• Log P: 2.3328612
• Molar Refractivity: 99.287 cm^3
• Polarizability: 38.320282 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S239502

A labelled lignan (phenylpropanoid) with significant estrogenic activity.

REFERENCES

• Fokialakis, N. et al.: Planta Medica, 69, 566 (2003)
• Lei, B. et al.: Mol. Cell. Endocrinol., 193, 81 (2003)