2-[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid

• ChemBase ID: 304941
• Molecular Formular: C17H24O11
• Molecular Mass: 404.36586
• Monoisotopic Mass: 404.13186159
• SMILES: [C@@H]1([C@H]([C@@H](OC=C1C(=O)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C=C)CC(=O)O
• Canonical SMILES: C=C[C@H]1[C@@H](OC=C([C@H]1CC(=O)O)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1
• InChIKey: MQLSOVRLZHTATK-PEYNGXJCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid
• IUPAC Traditional name: [(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid
• Synonyms: Secoxyloganin

Database IDs

• CAS Number: 58822-47-2

CALCULATED PROPERTIES

• Acid pKa: 3.869727
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.166222
• LogD (pH = 7.4): -4.76031
• Log P: -1.531335
• Molar Refractivity: 89.446 cm^3
• Polarizability: 36.318623 Å^3
• Polar Surface Area: 172.21 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder