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Showing Compound Amygdalin (FDB013636)

Record Information
Version1.0
Creation date2010-04-08 22:10:49 UTC
Update date2019-11-26 03:08:45 UTC
Primary IDFDB013636
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAmygdalin
DescriptionAmygdalin belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Amygdalin is found, on average, in the highest concentration within a few different foods, such as apricots (Prunus armeniaca), peaches (Prunus persica), and european plums (Prunus domestica) and in a lower concentration in apples (Malus pumila) and quinces (Cydonia oblonga). Amygdalin has also been detected, but not quantified in, several different foods, such as lima beans (Phaseolus lunatus), passion fruits (Passiflora edulis), pears (Pyrus communis), sour cherries (Prunus cerasus), and fruits. This could make amygdalin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Amygdalin.
CAS Number29883-15-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-D-Mandelonitrile beta-D-gentiobiosideHMDB
(R)-AmygdalinHMDB
(R)-AmygdalosideHMDB
(R)-LaenitrileHMDB
AmygdalosideHMDB, MeSH
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, HMDB
NeoamygdalinMeSH, HMDB
LaetrileMeSH, HMDB
Mandelonitrile beta gentiobiosideMeSH, HMDB
AmygdalinMeSH
(-)-d-mandelonitrile beta-d-gentiobiosidebiospider
(r)-amygdalinbiospider
(r)-amygdalosidebiospider
(r)-laenitrilebiospider
D-amygdalinbiospider
D-mandelonitrile-beta-D-glucosido-6-beta-D-glucosidebiospider
D(-)-mandelonitrile-β-d-gentiobiosidebiospider
D(-)-mandelonitrile-beta-d-gentiobiosidebiospider
Mandelonitrile-β-gentiobiosidebiospider
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H27NO11
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
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
InChI KeyXUCIJNAGGSZNQT-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight457.4285
Monoisotopic Molecular Weight457.158410711
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 52.51%; H 5.95%; N 3.06%; O 38.47%DFC
Melting PointMp 214°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -40.6 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAmygdalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00mx-3964600000-28e032c9faa617e24d81Spectrum
Predicted GC-MSAmygdalin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aor-3851049000-e90b077fb54d8ae5064fSpectrum
Predicted GC-MSAmygdalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAmygdalin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0002-5891300000-fba689b4129df72c18f42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0319400000-3553b5187f5432e0f5092021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-0229-1915200000-42ea18ed3050f7c2d7102021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0w2i-4900000000-e61f4cfa248ba96097af2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0319300000-a439d0cade12166f63ca2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0319300000-dc62f92995638c4ac5c02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-9200000000-79e3e830d8a6a67a39612021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0aba-9200000000-b38e139fc6acee04b5662021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-2915100000-fb6531aeefe3f224edf42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-2925100000-8569fc4373d740c75ba32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-03dr-5900000000-4406d5189b9c0b24eddb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0w29-4900000000-72d862d413fd46f5fb942021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0759-9400000000-12c917decf8164b2b2502021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0229-1915200000-c364edb3e61b2dda82a72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0910500000-43b5416a1c65aade6dd72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-a7b743b4f6c48ceeeec32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2900000000-c994efea7d35cfc3bc8d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-1920600000-bca6d39107a0a3d2c07f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900100000-3b83f13850f0c4b209be2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-6900000000-d6216be611d875daf6952017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0709700000-92924002bf77a15529d92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1912100000-f3e6a125f73a7327f2712021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-5900000000-96e192d154a114a1c28d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900300000-26cd8e61ab293ad5ea6c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2911200000-36f5a258da8c009d4a582021-09-23View Spectrum
NMRNot Available
ChemSpider ID2095
ChEMBL IDNot Available
KEGG Compound IDC08325
Pubchem Compound ID2180
Pubchem Substance IDNot Available
ChEBI ID27613
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35030
CRC / DFC (Dictionary of Food Compounds) IDJDX91-A:JFR77-K
EAFUS IDNot Available
Dr. Duke IDAMYGDALIN
BIGG IDNot Available
KNApSAcK IDC00001437
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAmygdalin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-tussive52217 An agent that suppresses coughing, reducing the frequency and severity of coughs. It works by targeting the brain's cough center, providing therapeutic relief for dry, irritating coughs. Key medical uses include managing coughs associated with colds, flu, and other respiratory conditions.DUKE
BitterA taste receptor stimulant, bitter substances play a biological role in toxin detection and expulsion. Therapeutically, they stimulate digestion and appetite. Key medical uses includeDUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
CyanogenicAn agent that releases hydrogen cyanide, playing a biological role in plant defense. It has therapeutic applications in cancer treatment and key medical uses in chemotherapy, due to its ability to inhibit cell growth and induce apoptosis in cancer cells.DUKE
Expectorant52217 An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways.DUKE
Toxic52209 A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.