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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:58:09 UTC
Update Date2017-12-07 03:36:10 UTC
HMDB IDHMDB0035030
Secondary Accession Numbers
  • HMDB35030
Metabolite Identification
Common NameAmygdalin
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
Structure
Thumb
Synonyms
ValueSource
(-)-D-Mandelonitrile beta-D-gentiobiosideHMDB
(R)-AmygdalinHMDB
(R)-AmygdalosideHMDB
(R)-LaenitrileHMDB
AmygdalosideHMDB
D(-)-Mandelonitrile-beta-D-gentiobiosideHMDB
D(-)-Mandelonitrile-β-D-gentiobiosideHMDB
D-AmygdalinHMDB
D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucosideHMDB
GlucoprunasinHMDB
Mandelonitrile gentiobiosideHMDB
Mandelonitrile-β-gentiobiosideHMDB
NSC 15780HMDB
Mandelonitrile-beta-gentiobiosideMeSH
NeoamygdalinMeSH
LaetrileMeSH
Mandelonitrile beta gentiobiosideMeSH
Chemical FormulaC20H27NO11
Average Molecular Weight457.4285
Monoisotopic Molecular Weight457.158410711
IUPAC Name2-phenyl-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile
Traditional Nameamygdalin
CAS Registry Number29883-15-6
SMILES
OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier
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
InChI KeyXUCIJNAGGSZNQT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point214 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
Polarizability44.61 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mx-3964600000-28e032c9faa617e24d81View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0aor-3851049000-e90b077fb54d8ae5064fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0910500000-43b5416a1c65aade6dd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-a7b743b4f6c48ceeeec3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-c994efea7d35cfc3bc8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-1920600000-bca6d39107a0a3d2c07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900100000-3b83f13850f0c4b209beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-6900000000-d6216be611d875daf695View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013636
KNApSAcK IDC00001437
Chemspider ID2095
KEGG Compound IDC08325
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAmygdalin
METLIN IDNot Available
PubChem Compound2180
PDB IDNot Available
ChEBI ID27613
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. [PubMed: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. [PubMed:16880611 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Prunasin + D-Glucose → Amygdalin + Waterdetails