[(2S,3R,4S,5S,6R)-2-[[(4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
Basic information
- CAS
21233-18-1- Standard SMILES
C=C[C@H]1C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2OC(=O)c2c(O)cc(O)cc2-c2cccc(O)c2)OC=C2C(=O)OCC[C@]21O- InChIKey
UZYZCCWBBBCDAD-YRLKQETISA-N- Molecular formula
- C29H30O14
- Average molar mass
- 602.5 g/mol
- Monoisotopic mass
- 602.16355563
Names & identifiers
- Preferred name
- [(2S,3R,4S,5S,6R)-2-[[(4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
- IUPAC
- [(2S,3R,4S,5S,6R)-2-[[(4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
- English name
- [(2S,3R,4S,5R,6R)-2-[[(1R,10R)-10-ethenyl-1-hydroxy-5-oxo-4,8-dioxabicyclo[4.4.0]dec-6-en-9-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
- Molecular formula
- C29H30O14
- Molecular weight
- 602.54
Names & synonyms
(1,1'-Biphenyl)-2-carboxylic acid, 3,3',5-trihydroxy-, 2-ester with 5-ethenyl-6-(beta-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-1H,3H-pyrano(3,4-c)pyran-1-one, (4aR-(4aalpha,5beta,6alpha))-[(2S,3R,4S,5S,6R)-2-[[(4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3,4,5,6-tetrahydropyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoateDTXSID70943652E89048(4aR,5R)-5-Ethenyl-4a-hydroxy-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl 2-O-(3,3',5-trihydroxy[1,1'-biphenyl]-2-carbonyl)-beta-D-glucopyranoside5-Ethenyl-4a-hydroxy-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl 2-O-(3,3',5-trihydroxy[1,1'-biphenyl]-2-carbonyl)hexopyranoside1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-4,4a,5,6-tetrahydro-4a-hydroxy-6-[[2-O-[(3,3',5-trihydroxy[1,1'-biphenyl]-2-yl)carbonyl]-β-D-glucopyranosyl]oxy]-, (4aR,5R,6S)-[(2S,3R,4S,5R,6R)-2-[[(1R,10R)-10-ethenyl-1-hydroxy-5-oxo-4,8-dioxabicyclo[4.4.0]dec-6-en-9-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 222 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 8
- Heavy atoms
- 43
- Formal charge
- 0
- Complexity
- 1,070
Physicochemical properties
- Boiling point
- 943.211 · 943.211±65.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.647 · 1.647±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 7.416 · 7.416±0.40(predicted)
- form
- Solid
- color
- Off-white to light yellow
Chemistry & industry
Applications
UsesAmaroswerin is a bioactive secoiridoid glucoside from Swertia mussotii. Amaroswerin has anti-inflammatory, antidiabetic, antiviral, anticholinergic and immunomodulatory activities. Amaroswerin inhibits NO release with an IC50value of 5.42 μg/mL inRAW264.7 cells[1].
Additional notes
DefinitionChEBI: Amaroswerin is a member of biphenyls.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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