CHEBI:17019 - (R)-amygdalin

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ChEBI Name (R)-amygdalin
ChEBI ID CHEBI:17019
ChEBI ASCII Name (R)-amygdalin
Definition An amygdalin in which the stereocentre on the cyanohydrin function has R-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:18681, CHEBI:10997, CHEBI:336
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Formula C20H27NO11
Net Charge 0
Average Mass 457.42850
InChI 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
InChIKey XUCIJNAGGSZNQT-JHSLDZJXSA-N
SMILES OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)c3ccccc3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
Metabolite of Species Details
Prunus serotina (NCBI:23207) Found in kernel (BTO:0000668). See: PubMed
Prunus armeniaca (NCBI:36596) Found in kernel (BTO:0000668). See: PubMed
Prunus dulcis var. amara (NCBI:3756) Found in kernel (BTO:0000668). See: PubMed
Prunus domestica (NCBI:3758) Found in kernel (BTO:0000668). See: PubMed
Prunus persica (NCBI:3760) Found in kernel (BTO:0000668). See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via amygdalin )
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via cyanogenic glycoside )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (R)-amygdalin (CHEBI:17019) has functional parent (R)-mandelonitrile (CHEBI:18450)
(R)-amygdalin (CHEBI:17019) has role antineoplastic agent (CHEBI:35610)
(R)-amygdalin (CHEBI:17019) has role apoptosis inducer (CHEBI:68495)
(R)-amygdalin (CHEBI:17019) has role plant metabolite (CHEBI:76924)
(R)-amygdalin (CHEBI:17019) is a amygdalin (CHEBI:27613)
IUPAC Name
(2R)-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy](phenyl)acetonitrile
Synonyms Sources
(-)-D-mandelonitrile beta-D-gentiobioside ChEBI
(R)-Amygdalin KEGG COMPOUND
(R)-amygdalin UniProt
(R)-Amygdaloside KEGG COMPOUND
(R)-Laenitrile KEGG COMPOUND
D-(−)-mandelonitrile-β-D-gentiobioside ChemIDplus
D-amygdalin ChemIDplus
D-mandelonitrile-β-D-glucosido-6-β-D-glucoside ChemIDplus
Database Links Databases
Amygdalin Wikipedia
C00001437 KNApSAcK
C08325 KEGG COMPOUND
CPD-1125 MetaCyc
HMDB35030 HMDB
View more database links
Registry Numbers Types Sources
29883-15-6 CAS Registry Number ChemIDplus
66856 Beilstein Registry Number Beilstein
66856 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10670815 PubMed citation CiteXplore
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Last Modified
25 May 2016