Amygdalin (T3D0813)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-06-05 21:22:26 UTC
Update Date2014-12-24 20:22:51 UTC
Accession NumberT3D0813
Identification
Common NameAmygdalin
ClassSmall Molecule
DescriptionAmygdalin is found in almond. Bitter glycoside of the Rosaceae, found especially in kernels of cherries, peaches and apricots. Amygdalin is present in cold pressed bitter almond oil from the above sources prior to enzymic hydolysis and steam distillation for food use Amygdalin , C20H27NO11, is a glycoside initially isolated from the seeds of the tree Prunus dulcis, also known as bitter almonds, by Pierre-Jean Robiquet and A. F. Boutron-Charlard in 1803, and subsequently investigated by Liebig and Wohler in 1830, and others. Several other related species in the genus of Prunus, including apricot (Prunus armeniaca) and black cherry (Prunus serotina), also contain amygdalin. It was promoted as a cancer cure by Ernst T. Krebs under the name Vitamin B17, but studies have found it to be ineffective. Amygdalin is sometimes confounded with laevomandelonitrile, also called laetrile for short; however, amygdalin and laetrile are different chemical compounds. Amygdalin has been shown to exhibit anti-nociceptive and apoptotic functions (1, 2). Amygdalin belongs to the family of Dihexoses. These are disaccharides containing two hexose carbohydrates.
Compound Type
  • Cyanide Compound
  • Cyanogenic Glycoside
  • Ether
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Nitrile
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(-)-D-mandelonitrile beta-D-gentiobioside
(R)-amygdalin
(R)-amygdaloside
(R)-laenitrile
Amygdaloside
D(-)-Mandelonitrile-beta-D-gentiobioside
D(-)-Mandelonitrile-β-D-gentiobioside
D-Amygdalin
D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside
Glucoprunasin
Mandelonitrile gentiobioside
Mandelonitrile-β-gentiobioside
NSC 15780
Chemical FormulaC20H27NO11
Average Molecular Mass457.429 g/mol
Monoisotopic Mass457.158 g/mol
CAS Registry Number29883-15-6
IUPAC Name2-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
Traditional Nameamygdalin
SMILES[H]C(O[C@]1([H])O[C@]([H])(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)(C#N)C1=CC=CC=C1
InChI IdentifierInChI=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/t10?,11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
InChI KeyInChIKey=XUCIJNAGGSZNQT-SWRVSKMJSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentCyanogenic glycosides
Alternative Parents
Substituents
  • Cyanogenic glycoside
  • Disaccharide
  • O-glycosyl compound
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Polyol
  • Nitrile
  • Carbonitrile
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point214°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility35.3 g/LALOGPS
logP-1.3ALOGPS
logP-2.6ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area202.32 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity102.51 m³·mol⁻¹ChemAxon
Polarizability43.19 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0910500000-6c1a1ef69fd6abcbb7a42017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-2cc0464d08db7cab19de2017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-2900000000-3ed6fced910b987910742017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-2920600000-01b14e785ae238b904a52017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900100000-03639fa8d97b0aa1e3b72017-06-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-6900000000-747d6394cb49483cdce02017-06-28View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityAmygdalin can be metabolized into hydrogen cyanide in the stomach causing discomfort or illness. (4) Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (7)
MetabolismBeta-glucosidase, one of the enzymes that catalyzes the release of the cyanide from amygdalin, is present in human small intestine and in a variety of common foods. This leads to an unpredictable and potentially lethal toxicity when amygdalin or Laetrile is taken orally. (4) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (6)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFruit seeds and pits. (4)
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB35030
PubChem Compound ID2180
ChEMBL IDNot Available
ChemSpider ID2095
KEGG IDC08325
UniProt IDNot Available
OMIM ID
ChEBI ID27613
BioCyc IDNot Available
CTD IDD000678
Stitch IDAmygdalin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkAmygdalin
References
Synthesis ReferenceNot Available
MSDST3D0813.pdf
General References
  1. Hwang HJ, Kim P, Kim CJ, Lee HJ, Shim I, Yin CS, Yang Y, Hahm DH: Antinociceptive effect of amygdalin isolated from Prunus armeniaca on formalin-induced pain in rats. Biol Pharm Bull. 2008 Aug;31(8):1559-64. [18670089 ]
  2. Chang HK, Shin MS, Yang HY, Lee JW, Kim YS, Lee MH, Kim J, Kim KH, Kim CJ: Amygdalin induces apoptosis through regulation of Bax and Bcl-2 expressions in human DU145 and LNCaP prostate cancer cells. Biol Pharm Bull. 2006 Aug;29(8):1597-602. [16880611 ]
  3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  4. Wikipedia. White lead. Last Updated 23 January 2009. [Link]
  5. Wikipedia. Amygdalin. Last Updated 4 June 2009. [Link]
  6. ATSDR - Agency for Toxic Substances and Disease Registry (2006). Toxicological profile for cyanide. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  7. Wikipedia. Cyanide poisoning. Last Updated 30 March 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available