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

• ChemBase ID: 304390
• Molecular Formular: C16H22O10
• Molecular Mass: 374.33988
• Monoisotopic Mass: 374.1212969
• SMILES: [C@@]12([C@H]([C@@H](OC=C1C(=O)OCC2)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO)C=C)O
• Canonical SMILES: C=C[C@H]1[C@@H](OC=C2[C@@]1(O)CCOC2=O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H22O10/c1-2-7-14(24-6-8-13(21)23-4-3-16(7,8)22)26-15-12(20)11(19)10(18)9(5-17)25-15/h2,6-7,9-12,14-15,17-20,22H,1,3-5H2/t7-,9+,10+,11-,12+,14-,15-,16+/m0/s1
• InChIKey: HEYZWPRKKUGDCR-QBXMEVCASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,5R,6S)-5-ethenyl-4a-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-1-one
• IUPAC Traditional name: swertiamarin
• Synonyms: Swertiamaroside; Swertiamarin

Database IDs

• CAS Number: 17388-39-5

CALCULATED PROPERTIES

• Acid pKa: 12.174738
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.1002095
• LogD (pH = 7.4): -2.1002166
• Log P: -2.1002092
• Molar Refractivity: 82.5717 cm^3
• Polarizability: 33.80736 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder