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ChEBI
> Main
CHEBI:17019 - (
R
)-amygdalin
Main
ChEBI Ontology
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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
Supplier Information
Download
Molfile
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Find compounds which resemble this structure
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Molfile
Wikipedia
License
Read full article at Wikipedia
Formulae
C20H27NO11
C20H27NO11
Net Charge
0
Average Mass
457.429
Monoisotopic Mass
457.15841
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
C(#N)
[C@H]
(O[C@H]
1[C@H]
(O)
[C@@H]
(O)
[C@H]
(O)
[C@H]
(O1)
CO[C@]
2([C@H]
(O)
[C@@H]
(O)
[C@H]
(O)
[C@H]
(O2)
CO)
[H]
)
C3=CC=CC=C3
Metabolite of Species
Details
Prunus serotina
(NCBI:txid23207)
Found in kernel
(BTO:0000668)
. See:
PubMed
Prunus armeniaca
(NCBI:txid36596)
Found in kernel
(BTO:0000668)
. See:
PubMed
Prunus dulcis
var.
amara
(NCBI:txid3756)
Found in kernel
(BTO:0000668)
. See:
PubMed
Prunus domestica
(NCBI:txid3758)
Found in kernel
(BTO:0000668)
. See:
PubMed
Prunus persica
(NCBI:txid3760)
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
(2
R
)-
[(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
Manual Xrefs
Databases
Amygdalin
Wikipedia
C00001437
KNApSAcK
C08325
KEGG COMPOUND
CPD-1125
MetaCyc
HMDB0035030
HMDB
View more database links
Registry Numbers
Types
Sources
29883-15-6
CAS Registry Number
ChemIDplus
66856
Reaxys Registry Number
Reaxys
Citations
Types
Sources
10670815
PubMed citation
Europe PMC
12232058
PubMed citation
Europe PMC
12372866
PubMed citation
Europe PMC
12428943
PubMed citation
Europe PMC
12975776
PubMed citation
Europe PMC
16652960
PubMed citation
Europe PMC
16880611
PubMed citation
Europe PMC
17359643
PubMed citation
Europe PMC
20191348
PubMed citation
Europe PMC
25050339
PubMed citation
Europe PMC
25237385
PubMed citation
Europe PMC
26431391
PubMed citation
Europe PMC
26719286
PubMed citation
Europe PMC
27119432
PubMed citation
Europe PMC
7092570
PubMed citation
Europe PMC
Last Modified
01 junio 2016