(3S,4S,6S)-2-({[(2R,3S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[4-(prop-2-en-1-yl)phenoxy]oxane-3,4,5-triol

• ChemBase ID: 169510
• Molecular Formular: C20H28O10
• Molecular Mass: 428.43032
• Monoisotopic Mass: 428.1682471
• SMILES: [C@@H]1(C(CO[C@H]1OCC1[C@H]([C@@H](C([C@@H](O1)Oc1ccc(cc1)CC=C)O)O)O)(O)CO)O
• Canonical SMILES: C=CCc1ccc(cc1)O[C@@H]1OC(CO[C@@H]2OCC([C@@H]2O)(O)CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C20H28O10/c1-2-3-11-4-6-12(7-5-11)29-18-16(24)15(23)14(22)13(30-18)8-27-19-17(25)20(26,9-21)10-28-19/h2,4-7,13-19,21-26H,1,3,8-10H2/t13?,14-,15+,16?,17-,18-,19-,20?/m1/s1
• InChIKey: HLTAEJNADMCLOV-UBQOPHAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6S)-2-({[(2R,3S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[4-(prop-2-en-1-yl)phenoxy]oxane-3,4,5-triol
• IUPAC Traditional name: (3S,4S,6S)-2-({[(2R,3S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[4-(prop-2-en-1-yl)phenoxy]oxane-3,4,5-triol
• Synonyms: 4-(2-Propen-1-yl)phenyl 6-O-D-Apio-β-D-furanosyl-β-D-glucopyranoside; p-Allylphenyl 6-O-β-D-apiofuranosyl-β-D-glucopyranoside; Furcatin

Database IDs

• CAS Number: 499-33-2
• PubChem SID: 162263642
• PubChem CID: 71317011

CALCULATED PROPERTIES

• Acid pKa: 11.701741
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -0.7763162
• LogD (pH = 7.4): -0.77633756
• Log P: -0.7763159
• Molar Refractivity: 101.1408 cm^3
• Polarizability: 41.083538 Å^3
• Polar Surface Area: 158.3 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F864060

Substrate of Furcatin Hydrolase (FH). This enzyme catalyzes the hydrolysis of Furcatin producing p-Allylphenol and the disaccharide Acuminose.

REFERENCES

• Ahn, Y., et al.: J. Biol., Chem., 279, 23405 (2004)
• Ahn, Y., et al.: Plant & Cell Physiol., 48, 938 (2004)
• Daiyasu, H., et al.: J. Biochem., 144, 467 (2004)