Showing Compound Amygdalin (FDB013636)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:49 UTC

Update date

2019-11-26 03:08:45 UTC

Primary ID

FDB013636

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Amygdalin

Description

Amygdalin 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 Number

29883-15-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-D-Mandelonitrile beta-D-gentiobioside	HMDB
(R)-Amygdalin	HMDB
(R)-Amygdaloside	HMDB
(R)-Laenitrile	HMDB
Amygdaloside	HMDB, MeSH
D(-)-Mandelonitrile-beta-D-gentiobioside	HMDB
D(-)-Mandelonitrile-β-D-gentiobioside	HMDB
D-Amygdalin	HMDB
D-Mandelonitrile-beta-D-glucosido-6-beta-D-glucoside	HMDB
Glucoprunasin	HMDB
Mandelonitrile gentiobioside	HMDB
Mandelonitrile-β-gentiobioside	HMDB
NSC 15780	HMDB
Mandelonitrile-beta-gentiobioside	MeSH, HMDB
Neoamygdalin	MeSH, HMDB
Laetrile	MeSH, HMDB
Mandelonitrile beta gentiobioside	MeSH, HMDB
Amygdalin	MeSH
(-)-d-mandelonitrile beta-d-gentiobioside	biospider
(r)-amygdalin	biospider
(r)-amygdaloside	biospider
(r)-laenitrile	biospider
D-amygdalin	biospider
D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside	biospider
D(-)-mandelonitrile-β-d-gentiobioside	biospider
D(-)-mandelonitrile-beta-d-gentiobioside	biospider
Mandelonitrile-β-gentiobioside	biospider

Predicted Properties

Property	Value	Source
Water Solubility	35.3 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.6	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	202.32 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.51 m³·mol⁻¹	ChemAxon
Polarizability	44.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C20H27NO11

IUPAC name

2-phenyl-2-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

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 Key

XUCIJNAGGSZNQT-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(O)C(O)C2O)C(O)C(O)C1O

Average Molecular Weight

457.4285

Monoisotopic Molecular Weight

457.158410711

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-1125 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Laboratory chemical

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 52.51%; H 5.95%; N 3.06%; O 38.47%	DFC
Melting Point	Mp 214°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]25D -40.6 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Amygdalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00mx-3964600000-28e032c9faa617e24d81	Spectrum
Predicted GC-MS	Amygdalin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0aor-3851049000-e90b077fb54d8ae5064f	Spectrum
Predicted GC-MS	Amygdalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Amygdalin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0002-5891300000-fba689b4129df72c18f4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0319400000-3553b5187f5432e0f509	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-0229-1915200000-42ea18ed3050f7c2d710	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0w2i-4900000000-e61f4cfa248ba96097af	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0319300000-a439d0cade12166f63ca	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-0319300000-dc62f92995638c4ac5c0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-9200000000-79e3e830d8a6a67a3961	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0aba-9200000000-b38e139fc6acee04b566	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-2915100000-fb6531aeefe3f224edf4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-2925100000-8569fc4373d740c75ba3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-03dr-5900000000-4406d5189b9c0b24eddb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0w29-4900000000-72d862d413fd46f5fb94	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0759-9400000000-12c917decf8164b2b250	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0229-1915200000-c364edb3e61b2dda82a7	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0910500000-43b5416a1c65aade6dd7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0900000000-a7b743b4f6c48ceeeec3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-2900000000-c994efea7d35cfc3bc8d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a59-1920600000-bca6d39107a0a3d2c07f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900100000-3b83f13850f0c4b209be	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-6900000000-d6216be611d875daf695	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0709700000-92924002bf77a15529d9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1912100000-f3e6a125f73a7327f271	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-5900000000-96e192d154a114a1c28d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900300000-26cd8e61ab293ad5ea6c	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2911200000-36f5a258da8c009d4a58	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

2095

ChEMBL ID

Not Available

KEGG Compound ID

C08325

Pubchem Compound ID

2180

Pubchem Substance ID

Not Available

ChEBI ID

27613

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35030

CRC / DFC (Dictionary of Food Compounds) ID

JDX91-A:JFR77-K

EAFUS ID

Not Available

Dr. Duke ID

AMYGDALIN

BIGG ID

Not Available

KNApSAcK ID

C00001437

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Amygdalin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti tussive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
bitter			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cyanogenic			DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
toxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE