Amygdaloside

HCID 34751

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Basic information

CAS: 51371-34-7
Standard SMILES: N#CC(O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)c1ccccc1
InChIKey: XUCIJNAGGSZNQT-SWRVSKMJSA-N
Molecular formula: C20H27NO11
Average molar mass: 457.4 g/mol
Monoisotopic mass: 457.15841068

Overview

Amygdalin is a cyanogenic glycoside, a gentiobioside and a disaccharide derivative. It has a role as a plant metabolite. It is functionally related to a prunasin.

Names & identifiers

Preferred name: Amygdaloside
IUPAC: 2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile

Names & synonyms

Amygdaloside2-phenyl-2-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)acetonitrile96420-61-0C20H27NO112-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrileD-Amygdalin hydrateDL-Amygdalin2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrileD(-)-AmygdalinMFCD00866428Apricot Kernel PowderSpectrum_001192

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Spectrum2_000904Spectrum3_001534Spectrum4_001750Spectrum5_000580BSPBio_002948KBioGR_002200KBioSS_001672DivK1c_000106

Database identifiers

CAS

Properties

Computed structural properties

XLogP: -2.7
Topological polar surface area: 202 Å²
Hydrogen bond donors: 7
Hydrogen bond acceptors: 12
Rotatable bonds: 7
Heavy atoms: 32
Formal charge: 0
Complexity: 638

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Compound notes

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