Compound: amygdalin
SMILES: O1[C@@H](O[C@@H](C#N)c2ccccc2)[C@H](O)[C@@H](O)[C@@H]([C@H]1CO[C@@H]3O[C@@H]([C@@H](O)[C@@H]([C@H]3O)O)CO)O
InChIKey: XUCIJNAGGSZNQT-JHSLDZJXSA-N
Synonyms: amygdalin, 29883-15-6, (R)-Amygdalin, D-Amygdalin, (R)-Laenitrile, (R)-Amygdaloside, R-Amygdalin, NSC-15780, D(-)-Mandelonitrile-beta-D-gentiobioside, D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside, 214UUQ9N0H, NSC 15780, Glucoprunasin, CHEBI:17019, DTXSID00897159, (-)-D-mandelonitrile beta-D-gentiobioside, (2R)-[(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy](phenyl)acetonitrile, (R)-alpha-((6-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy)benzeneacetonitrile, Benzeneacetonitrile, alpha-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-, (R)-, (2R)-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, CHEBI:27613, NSC251222, (2R)-((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile, (2R)-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, RefChem:5553, Mandelonitrile beta Gentiobioside, DTXCID701326581, 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)oxy)methyl)oxan-2-yl)oxy)acetonitrile, 249-925-3, ((6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)(phenyl)acetonitrile, NSC15780, Amygdaloside, (R)-2-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)acetonitrile, Benzeneacetonitrile,a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-, (aR)-, MFCD00006598, C20H27NO11, (2R)-2-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-acetonitrile, amygdaline, UNII-214UUQ9N0H, MFCD00866428, HSDB 3559, EINECS 249-925-3, BRN 0066856, Amygdalin/Vitamin B17, AMYGDALIN [MI], AMYGDALIN [HSDB], bmse000139, AMYGDALIN [WHO-DD], 5-17-08-00118 (Beilstein Handbook Reference), MLS002473175, SCHEMBL131406, CHEMBL461727, orb1305010, orb3140227, MSK1532, HMS2205O07, HY-N0190, s2260, AKOS016034288, CCG-269308, CS-6162, DS-7377, EBC-617148, SMP1_000103, (2R)-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]oxy}methyl)oxan-2-yl]oxy}acetonitrile, AC-27315, SMR001397267, SY067870, D-(-)-mandelonitrile-beta-D-gentiobioside, NS00015336, C08325, Q410215, BRD-K03504028-001-07-6, (2R)-((6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)(PHENYL)ACETONITRILE, (R)-alpha-((6-O-beta-D-glucopyranosyl-beta-D- glucopyranosyl)oxy)benzeneacetonitrile, (r)-alpha-((6-o-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy)benzeneaceto, Benzeneacetonitrile, alpha-[(6-O-.beta.-D-glucopyransoyl-.beta.-D-glucopyranosyl)oxy]-, (R)-
Theoretical properties:
molecular_formula: C20H27NO11
molecular_weight: 457.4 g/mol
exact_mass: 457.15841068 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 7
heavy_atom_count: 32
topological_polar_surface_area: 202 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 223-226 °C
solubility: VERY SOL IN HOT WATER; SLIGHTLY SOL IN ALCOHOL; INSOL IN ETHER, CHLOROFORM; SOL IN HOT ALCOHOL
Descriptions:
pubchem: (R)-amygdalin is an amygdalin in which the stereocentre on the cyanohydrin function has R-configuration. It has a role as an antineoplastic agent, an apoptosis inducer and a plant metabolite. It is functionally related to a (R)-mandelonitrile.
chebi: An amygdalin in which the stereocentre on the cyanohydrin function has <i>R</i>-configuration.
chembl: AMYGDALIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Amygdalin (from Ancient Greek: ἀμυγδαλή amygdalē 'almond') is a naturally occurring chemical compound found in many plants, most notably in the seeds (kernels, pips or stones) of apricots, bitter almonds, apples, peaches, cherries and plums, and in the roots of manioc.
Amygdalin is classified as a cyanogenic glycoside, because each amygdalin molecule includes a nitrile group, which can be released as the toxic cyanide anion by the action of a beta-glucosidase. Eating amygdalin will cause it to release cyanide in the human body, and may lead to cyanide poisoning.
Since the early 1950s, both amygdalin and a chemical derivative named laetrile have been promoted as alternative cancer treatments, often under the misnomer vitamin B17 (neither amygdalin nor laetrile is a vitamin). Scientific study has found them to not only be clinically ineffective in treating cancer but also dangerous due to the considerable poisoning risks. The promotion of laetrile to treat cancer has been described in the medical literature as a canonical example of quackery and as "the slickest, most sophisticated, and certainly the most remunerative cancer quack promotion in medical history". Amygdalin has also been examined in the context of traditional Chinese medicine.