(R)-amygdalin (Q410215)

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cyanogenic glycoside present in kernels of fruit

D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside
D-(-)-mandelonitrile-beta-D-gentiobioside
D-amygdalin
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-acetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-ethanenitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile

Language	Label	Description	Also known as
English	(R)-amygdalin	cyanogenic glycoside present in kernels of fruit	D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside D-(-)-mandelonitrile-beta-D-gentiobioside D-amygdalin (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-acetonitrile (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-ethanenitrile (2R)-2-phenyl-2-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile

Statements

type of chemical entity

0 references

0 references

amygdalin beta-glucosidase activity

1 reference

Gene Ontology release 2020-05-02

Rhea release 113

1 reference

Wikimedia import URL

https://en.wikipedia.org/wiki/Amygdalin

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chemical structure

Amygdalin structure.svg
512 × 278; 26 KB

1 reference

imported from Wikimedia project

German Wikipedia

457.158411 dalton

1 reference

language of work or name

amygdalin (English)

5 October 2016

stereoisomer of

2 references

based on heuristic

inferred from InChIKey

based on heuristic

inferred from InChI

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

1 reference

based on heuristic

inferred from InChI

chemical formula

C₂₀H₂₇NO₁₁

1 reference

language of work or name

amygdalin (English)

5 October 2016

canonical 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

1 reference

language of work or name

amygdalin (English)

5 October 2016

isomeric SMILES

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)C3=CC=CC=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

1 reference

Global Substance Registration System

14 February 2018

safety classification and labelling

NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response

1

0

NFPA Instability

0

no value

1 reference

imported from Wikimedia project

English Wikipedia

Gerbera jamesonii

2 references

Cyanogenic glycosides and 4-hydroxycoumarin glycosides from Gerbera jamesonii hybrida.

New glucosides of a 4-hydroxy-5-methylcoumarin and a dihydro-.ALPHA.-pyrone from Gerbera jamesonii hybrida.

1 reference

Cyclooxygenase inhibitory and antioxidant compounds from crabapple fruits

Oxyanthus pyriformis

1 reference

Cyanogenic glycosides from PS Psydrax and Oxyanthus species[a/t]

Vergonis planta

1 reference

Identification and Quantification of Passion Fruit Cyanogenic Glycosides

Prunus armeniaca

4 references

Micellar electrokinetic chromatography for the analysis of d-amygdalin and its epimer in apricot kernel

Bitterness in Aqueous Extracts of Apricot Kernels.

Quality control of traditional chinese drugs by high performance liquid chromatography.

Quick screening of major constituents in plant tissue by temperature programmed fractionation mass spectrometry

1 reference

Quantification of benzaldehyde and its precursors in montmorency cherry (Prunus cerasus L.) kernels

Prunus domestica

1 reference

Tissue Level Compartmentation of (R)-Amygdalin and Amygdalin Hydrolase Prevents Large-Scale Cyanogenesis in Undamaged Prunus Seeds.

5 references

Anti-tumor promoting effect of glycosides from Prunus persica seeds

Apoptosis induction of Persicae Semen extract in human promyelocytic leukemia (HL-60) cells

Development of quantitative extraction method of amygdalin without enzymatic hydrolysis from tonin(Persicae Semen) by high performance liquid chromatography

FLAVONOIDS AND CYANOGENIC GLYCOSIDES FROM THE LEAVES AND STEM BARK OF PRUNUS PERSICA (L.) BATSCH (MEET GHAMR) PEACH LOCAL CULTIVAR IN ASSIUT REGION

The pharmacokinetics of amygdalin

Prunus salicina

1 reference

Changes in Cyanogenic Glycoside Content and ^|^beta;-Cyanoalanine Synthase Activity in Flesh and Seeds of Japanese Plum (Prunus salicina Lindl.) during Development

Prunus serotina

2 references

Tissue and Subcellular Localization of Enzymes Catabolizing (R)-Amygdalin in Mature Prunus serotina Seeds.

Tissue Level Compartmentation of (R)-Amygdalin and Amygdalin Hydrolase Prevents Large-Scale Cyanogenesis in Undamaged Prunus Seeds.

1 reference

Cyanogenic glycosids from Prunus spinosa (Rosaceae)

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Distimake tuberosus

1 reference

Amygdalin acyl derivatives, cyanogenic glycosides from the seeds of Merremia dissecta

Eucalyptus camphora

1 reference

Novel aspects of cyanogenesis in Eucalyptus camphora subsp. humeana

1 reference

Novel aspects of cyanogenesis in Eucalyptus camphora subsp. humeana

described by source

Encyclopedic Lexicon

statement is subject of

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Great Soviet Encyclopedia (1926–1947)

statement is subject of

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Brockhaus and Efron Encyclopedic Dictionary

statement is subject of

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Small Brockhaus and Efron Encyclopedic Dictionary

statement is subject of

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has characteristic

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hydrogen cyanide

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subject has role

phytogenic antineoplastic agents

1 reference

Medical Subject Headings

MeSH descriptor ID

15 March 2018

NCI Thesaurus ID

C28801

1 reference

Global Substance Registration System

14 February 2018

0 references

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Identifiers

National Library of Israel J9U ID

987007550882505171

1 reference

National Library of Israel Names and Subjects Authority File

Library of Congress authority ID

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subject named as

vitamin B17

0 references

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/t10-,11+,12+,13+,14+,15-,16-,17+,18+,19+,20+/m0/s1

1 reference

language of work or name

amygdalin (English)

5 October 2016

XUCIJNAGGSZNQT-JHSLDZJXSA-N

2 references

language of work or name

amygdalin (English)

5 October 2016

Global Substance Registration System

14 February 2018

CAS Registry Number

3 references

language of work or name

(R)-amygdalin (English)

5 October 2016

Global Substance Registration System

14 February 2018

XUCIJNAGGSZNQT-JHSLDZJXSA-N

CAS Common Chemistry

9 April 2021

https://commonchemistry.cas.org/detail?cas_rn=29883-15-6

1 reference

language of work or name

Amygdalin (English)

5 October 2016

1 reference

language of work or name

amygdalin (English)

5 October 2016

Reaxys registry number

66856

1 reference

language of work or name

(R)-amygdalin (English)

5 October 2016

mapping relation type

3 references

language of work or name

(R)-amygdalin (English)

5 October 2016

ChEBI release 2019-10-02

ChEBI release 2021-03-01

1 reference

language of work or name

AMYGDALIN (English)

5 October 2016

UniChem compound ID

1 reference

MassBank accession ID

MSBNK-Univ_Toyama-TY000092

0 references

splash10-004i-0000900000-83c663aef3308d0e8547

0 references

0 references

1 reference

Hazardous Substances Data Bank

publication date

28 October 2019

AMYGDALIN (English)

10 May 2021

DSSTox substance ID

0 references

DSSTOX compound identifier

DTXCID701326581

0 references

0 references

249-925-3

2 references

Global Substance Registration System

14 February 2018

ECHA Substance Infocard database

ECHA Substance Infocard ID

27 December 2018

Amygdalin (English)

CAS no.: 29883-15-6 (English)

ECHA Substance Infocard ID

2 references

http://echa.europa.eu/de/information-on-chemicals/registered-substances

ECHA Substance Infocard database

ECHA Substance Infocard ID

27 December 2018

Amygdalin (English)

CAS no.: 29883-15-6 (English)

AICS Chemical ID (BEING DELETED)

0 references

MeSH descriptor ID

subject named as

Amygdalin

1 reference

Medical Subject Headings

MeSH descriptor ID

14 March 2018

0 references

D09.408.348.050

0 references

1 reference

Global Substance Registration System

14 February 2018

Human Metabolome Database ID

0 references

1 reference

language of work or name

(R)-amygdalin (English)

5 October 2016

1 reference

Global Substance Registration System

14 February 2018

Probes And Drugs ID

0 references

0 references

1 reference

Freebase Data Dumps

publication date

28 October 2013

Microsoft Academic ID

0 references

0 references

1 reference

26 January 2022

https://docs.openalex.org/download-snapshot/snapshot-data-format

Römpp online ID

1 reference

imported from Wikimedia project

German Wikipedia

ScienceDirect topic ID

agricultural-and-biological-sciences/amygdalin

0 references

1 reference

based on heuristic

inferred by common MeSH mappings on source and on Wikidata

24 May 2023

WordNet 3.1 Synset ID

14911615-n

1 reference

Sitelinks

Wikipedia(37 entries)

Wikibooks(0 entries)

Wikinews(0 entries)

Wikiquote(0 entries)

Wikisource(0 entries)

Wikiversity(0 entries)

Wikivoyage(0 entries)

Wiktionary(0 entries)

Multilingual sites(0 entries)

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