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2-Phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile

PubChem CID: 2180

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Compound Synonyms amygdalin, D-Amygdalin, Isoamygdalin, Amygdaloside, Glucoprunasin, 29883-15-6, 51371-34-7, 2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile, DL-Amygdalin, Mandelonitrile-beta-gentiobioside, NSC251222, Mandelonitrile-.beta.-gentiobioside, D(-)-Mandelonitrile-.beta.-D-gentiobioside, D-(-)-Amygdalin, Benzeneacetonitrile, ., AMYGDALIN(D), AMYGDALIN,(DL), Mandelonitrile gentiobioside, CHEMBL1967951, SCHEMBL13387202, GTPL12451, DTXSID20872004, XUCIJNAGGSZNQT-UHFFFAOYSA-N, HMS3341N01, HMS3655P16, AKOS024282419, NSC-251222, OM05087, Benzeneacetonitrile, .alpha.-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-, NCGC00380662-01, 2-phenyl-2-(3,4,5-trihydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6 -tetrahydropyran-2-yloxy)]methyl}(2H-3,4,5,6-tetrahydropyran-2-yloxy))ethaneni trile, Benzeneacetonitrile, .alpha.-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-, (R)-, LS-14805, NCI60_002005, NS00097233, [(6-O-Hexopyranosylhexopyranosyl)oxy](phenyl)acetonitrile #, alpha-[(6-O-Hexopyranosylhexopyranosyl)oxy]benzeneacetonitrile, Benzeneacetonitrile,a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-, Benzeneacetonitrile, .alpha.-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-gluco-pyranosyl)oxy]-, D-Mandelonitrile-b-D-glucoside-6-O-b-D-glucoside, D-Mandelonitrile-b-gentiobioside, 1173199-73-9, 2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
Topological Polar Surface Area 202.0
Hydrogen Bond Donor Count 7.0
Heavy Atom Count 32.0
Description Amygdalin is a bitter glycoside of the Rosaceae, found in sources such as kernels of cherries, peaches and apricots. Present in cold pressed bitter almond oil from the these sources prior to enzymic hydolysis and steam distillation for food use. Amygdalin can also be found in passion fruit.
Isotope Atom Count 0.0
Molecular Complexity 638.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id Q9H227, n.a.
Iupac Name 2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
Prediction Hob 0.0
Class Organooxygen compounds
Xlogp -2.7
Superclass Organic oxygen compounds
Subclass Carbohydrates and carbohydrate conjugates
Molecular Formula C20H27NO11
Prediction Swissadme 0.0
Inchi Key XUCIJNAGGSZNQT-UHFFFAOYSA-N
Fcsp3 0.65
Logs -0.663
Rotatable Bond Count 7.0
State Solid
Logd -0.216
Synonyms (-)-d-mandelonitrile beta-d-gentiobioside, (r)-amygdalin, (r)-amygdaloside, (r)-laenitrile, Amygdalin, Amygdaloside, D-amygdalin, D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside, D(-)-mandelonitrile-&beta, -d-gentiobioside, D(-)-mandelonitrile-beta-d-gentiobioside, D(-)-Mandelonitrile-β-D-gentiobioside, Glucoprunasin, Mandelonitrile gentiobioside, Mandelonitrile-&beta, -gentiobioside, Mandelonitrile-β-gentiobioside, NSC 15780, (-)-D-Mandelonitrile beta-D-gentiobioside, (R)-Amygdalin, (R)-Amygdaloside, (R)-Laenitrile, D(-)-Mandelonitrile-beta-D-gentiobioside, D-Amygdalin, D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside, Mandelonitrile-beta-gentiobioside, Neoamygdalin, Laetrile, Mandelonitrile beta gentiobioside
Compound Name 2-Phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 457.158
Formal Charge 0.0
Monoisotopic Mass 457.158
Hydrogen Bond Acceptor Count 12.0
Molecular Weight 457.4
Covalent Unit Count 1.0
Total Atom Stereocenter Count 11.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteromonocyclic compounds
Esol -0.6455284000000003
Inchi InChI=1S/C20H27NO11/c21-6-10(9-4-2-1-3-5-9)30-20-18(28)16(26)14(24)12(32-20)8-29-19-17(27)15(25)13(23)11(7-22)31-19/h1-5,10-20,22-28H,7-8H2
Smiles C1=CC=C(C=C1)C(C#N)OC2C(C(C(C(O2)COC3C(C(C(C(O3)CO)O)O)O)O)O)O
Nring 3.0
Defined Bond Stereocenter Count 0.0
Taxonomy Direct Parent Cyanogenic glycosides

  • 1. Outgoing r'ship FOUND_IN to/from Cydonia Oblonga (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 2. Outgoing r'ship FOUND_IN to/from Eriobotrya Japonica (Plant) Rel Props:Source_db:fooddb_chem_all
  • 3. Outgoing r'ship FOUND_IN to/from Malus Domestica (Plant) Rel Props:Source_db:fooddb_chem_all
  • 4. Outgoing r'ship FOUND_IN to/from Malus Pumila (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 5. Outgoing r'ship FOUND_IN to/from Passiflora Edulis (Plant) Rel Props:Source_db:fooddb_chem_all
  • 6. Outgoing r'ship FOUND_IN to/from Phaseolus Lunatus (Plant) Rel Props:Source_db:fooddb_chem_all
  • 7. Outgoing r'ship FOUND_IN to/from Prunus Armeniaca (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 8. Outgoing r'ship FOUND_IN to/from Prunus Cerasus (Plant) Rel Props:Source_db:fooddb_chem_all
  • 9. Outgoing r'ship FOUND_IN to/from Prunus Davidiana (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 10. Outgoing r'ship FOUND_IN to/from Prunus Domestica (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 11. Outgoing r'ship FOUND_IN to/from Prunus Humilis (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 12. Outgoing r'ship FOUND_IN to/from Prunus Japonica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 13. Outgoing r'ship FOUND_IN to/from Prunus Mandshurica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 14. Outgoing r'ship FOUND_IN to/from Prunus Persica (Plant) Rel Props:Source_db:cmaup_ingredients;fooddb_chem_all;npass_chem_all
  • 15. Outgoing r'ship FOUND_IN to/from Prunus Sibirica (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all
  • 16. Outgoing r'ship FOUND_IN to/from Prunus Virginiana (Plant) Rel Props:Source_db:fooddb_chem_all
  • 17. Outgoing r'ship FOUND_IN to/from Pyrus Communis (Plant) Rel Props:Source_db:fooddb_chem_all
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