(5R,6S)-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,5H,6H-pyrano[3,4-c]pyran-1-one

• ChemBase ID: 305031
• Molecular Formular: C16H20O9
• Molecular Mass: 356.3246
• Monoisotopic Mass: 356.11073222
• SMILES: C12=CCOC(=O)C2=CO[C@H]([C@@H]1C=C)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO
• Canonical SMILES: C=C[C@H]1[C@@H](OC=C2C1=CCOC2=O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
• InChIKey: DUAGQYUORDTXOR-GPQRQXLASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6S)-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,5H,6H-pyrano[3,4-c]pyran-1-one
• IUPAC Traditional name: gentiopicroside
• Synonyms: Gentiopicrin; Gentiopicroside

Database IDs

• CAS Number: 20831-76-9

CALCULATED PROPERTIES

• Acid pKa: 5.297932
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.7878541
• LogD (pH = 7.4): -3.2126622
• Log P: -1.3788668
• Molar Refractivity: 82.144 cm^3
• Polarizability: 32.858147 Å^3
• Polar Surface Area: 134.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder