(5R,6S)-3-(beta-D-Glucopyranosyloxy)-1,2,3,6-tetrahydro-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-pyridinecarbonitrile
Basic information
- CAS
81861-72-5- Standard SMILES
COC1=CC(=O)N(C)[C@@H](O)[C@]1(C#N)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
QZRKNNXRNBTODR-JKTRLFLGSA-N- Molecular formula
- C14H20N2O9
- Average molar mass
- 360.32 g/mol
- Monoisotopic mass
- 360.11688022
Overview
Acalyphin is a member of the class of tetrahydropyridines that is 2,3-dihydroxy-4-methoxy-1-methyl-6-oxo-1,2,3,6-tetrahydropyridine-3-carbonitrile having a beta-D-glucosyl residue attached at position 3 via a glycosidic bond. It has a role as a plant metabolite. It is a beta-D-glucoside, a tetrahydropyridine, an enol ether, a delta-lactam and an aliphatic nitrile.
Names & identifiers
- Preferred name
- (5R,6S)-3-(beta-D-Glucopyranosyloxy)-1,2,3,6-tetrahydro-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-pyridinecarbonitrile
- IUPAC
- (2S,3R)-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-pyridine-3-carbonitrile
- English name
- 2-hydroxy-4-methoxy-1-methyl-6-oxo-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-pyridine-3-carbonitrile
- Molecular formula
- C14H20N2O9
- Molecular weight
- 360.32
Names & synonyms
ACALYPHIN81861-72-5CHEBI:2372(2S,3R)-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-2H-pyridine-3-carbonitrile(2S,3R)-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2H-pyridine-3-carbonitrileRefChem:934868(5R,6S)-3-(beta-D-Glucopyranosyloxy)-1,2,3,6-tetrahydro-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-pyridinecarbonitrileC08324orb1698783AKOS040750047HY-122764CS-0088858
Show more names
3-Pyridinecarbonitrile, 3-(β-D-glucopyranosyloxy)-1,2,3,6-tetrahydro-2-hydroxy-4-methoxy-1-methyl-6-oxo-, (5R,6S)-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-pyridine-3-carbonitrile
T29544Q27105645(2S,3R)-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-pyridine-3-carbonitrile3-(beta-D-glucopyranosyloxy)-1,2,3,6-tetrahydro-2-hydroxy-4-methoxy-1-methyl-6-oxo-3-pyridinecarbonitrile3-(beta-D-glucopyranosyloxy)-2-hydroxy-4-methoxy-1-methyl-6-oxo-1,2,3,6-tetrahydropyridine-3-carbonitrile
Properties
Computed structural properties
- XLogP
- -2.9
- Topological polar surface area
- 173 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 602
Physicochemical properties
- Boiling point
- 765 · 765.0±60.0 °C(Predicted)
- Density
- 1.62 · 1.62±0.1 g/cm3(Predicted)
- pka
- 10.5 · 10.50±0.60(Predicted)
Chemistry & industry
Applications
DescriptionAcalyphin is a cyanogenic pyridone glucosides from Acalypha indica (Euphorbiaceae).
UsesAcalyphin, a cyanogenic glucoside, is nature product that could be isolated from the aerial parts of Acalypha indica[1].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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