(2R,3S,4R,5S)-2-[(E)-2-[2-(hydroxymethyl)-3-methoxyphenyl]ethenyl]-5-methyloxolane-3,4-diol

• ChemBase ID: 179471
• Molecular Formular: C15H20O5
• Molecular Mass: 280.3163
• Monoisotopic Mass: 280.13107374
• SMILES: c1(c(c(ccc1)OC)CO)/C=C/[C@@H]1[C@H]([C@H]([C@@H](O1)C)O)O
• Canonical SMILES: OCc1c(/C=C/[C@H]2O[C@H]([C@@H]([C@@H]2O)O)C)cccc1OC
• InChI: InChI=1S/C15H20O5/c1-9-14(17)15(18)13(20-9)7-6-10-4-3-5-12(19-2)11(10)8-16/h3-7,9,13-18H,8H2,1-2H3/b7-6+/t9-,13+,14-,15+/m0/s1
• InChIKey: JGUADRHIBCXAFH-XAUFSTHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5S)-2-[(E)-2-[2-(hydroxymethyl)-3-methoxyphenyl]ethenyl]-5-methyloxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,4R,5S)-2-[(E)-2-[2-(hydroxymethyl)-3-methoxyphenyl]ethenyl]-5-methyloxolane-3,4-diol
• Synonyms: (6E)-2,5-Anhydro-1,6,7-trideoxy-7-[2-(hydroxymethyl)-3-methoxyphenyl]-D-allo-Hept-6-enitol; Varitriol; (+)-Varitriol

Database IDs

• CAS Number: 419568-67-5
• PubChem SID: 164235381
• PubChem CID: 636888

CALCULATED PROPERTIES

• Acid pKa: 12.80449
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.57806444
• LogD (pH = 7.4): 0.5780628
• Log P: 0.57806444
• Molar Refractivity: 75.2678 cm^3
• Polarizability: 29.249023 Å^3
• Polar Surface Area: 79.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - V099010

An antitumor natural product.

REFERENCES

• Malmstrom, J., et al.: J. Nat. Prod., 65, 364 (2002)
• Nagarapu, L., et al.: Bioorg. Med. Chem. Lett., 18, 2351 (2002)