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(R)-amygdalin

cyanogenic glycoside present in kernels of fruit
Class type of: (RS)-amygdalin Q410215

Facts

15 properties
Instance of
type of chemical entity
Subclass of
(RS)-amygdalin
Part of
amygdalin beta-glucosidase activity, apple seed, almond
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
Chemical formula
C₂₀H₂₇NO₁₁
Described by source
Encyclopedic Lexicon, Great Soviet Encyclopedia (1926–1947), Brockhaus and Efron Encyclopedic Dictionary, Small Brockhaus and Efron Encyclopedic Dictionary
Found in taxon
Gerbera jamesonii, Malus, Oxyanthus pyriformis, Passiflora edulis, Prunus armeniaca, Prunus cerasus, Prunus domestica, Prunus persica, Prunus salicina, Prunus serotina, Prunus spinosa, Prunus dulcis, Distimake tuberosus, Eucalyptus camphora, Eucalyptus
Has characteristic
bitterness, odor
Has part(s)
oxygen, carbon, nitrogen, hydrogen
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
Mass
+457.158411
NCI Thesaurus ID
C28801
Safety classification and labelling
NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response
Stereoisomer of
Neoamygdalin, (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
Subject has role
phytogenic antineoplastic agents
🏷️ Also known as
en (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 en (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 en (R)-amygdalin en D-mandelonitrile-beta-D-glucosido-6-beta-D-glucoside en D-(-)-mandelonitrile-beta-D-gentiobioside en D-amygdalin en (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 en (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 ar أميغدالين ar أميجدالين cs amygdalin cs Vitamín B17 cs Vitamin B17 de B17-Therapie de Vitamin B17 de Lätril de Laetrile el Βιταμίνη Β17 el Λεατρίλη el Νιτριλοσίδη
🔖 Identifiers · 50
Library of Congress Authorities ID
sh85073922
GND ID
7517769-9
OpenAlex ID
C2781274105
BabelNet ID
00003700n
CAS Registry Number
29883-15-6
ChEBI ID
17019
ChEMBL ID
CHEMBL461727
ChemSpider ID
570897
DSSTOX compound identifier
DTXCID701326581
DSSTox substance ID
DTXSID00897159
EC number
249-925-3
ECHA Substance Infocard ID
100.045.372
Show all 50 identifiers +38
EU Knowledge Graph item ID
Roble Shipping Inc.
FAST ID
990730
Freebase ID
/m/014s7
Golden ID (archived)
Amygdalin-R3VV
HSDB ID
3559
Human Metabolome Database ID
HMDB0035030
IdRef ID
04066113X
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
J9U entity ID
987007550882505171
KEGG ID
C08325
KNApSAcK ID
C00001437
MassBank accession ID
MSBNK-Univ_Toyama-TY000092
MeSH concept ID
M0001043
MeSH descriptor ID
D000678
MeSH term ID
T002060
MeSH tree code
D02.626.175, D09.408.348.050
Microsoft Academic ID (discontinued)
2781274105
NALT ID
8212
NL CR AUT ID
ph670379
NMRShiftDB structure ID
40265325
NSC number
15780
Probes And Drugs ID
PD021638
PubChem CID
656516
Reaxys registry number
66856
RxNorm CUI
1371051
Römpp online ID
RD-01-02266
SPLASH
splash10-004i-0000900000-83c663aef3308d0e8547
ScienceDirect topic ID
agricultural-and-biological-sciences/amygdalin, biochemistry-genetics-and-molecular-biology/amygdalin
SureChEMBL ID
131406
UMLS CUI
C0002707
UNII
214UUQ9N0H
UniChem compound ID
237271
Wellcome Collection concept ID
mtj5etep
WordNet 3.1 Synset ID
14911615-n
Yale LUX ID
concept/78ec735a-5927-49c5-8c73-055e6d9a9845
Yle topic ID
18-285645
ZVG number
137642

Report an error or request removal Lineage (PROV-JSON)

🔗 Connections
Found in taxon 13
Prunus persica, Prunus armeniaca, Eucalyptus, Malus, Prunus domestica, Prunus spinosa, Passiflora edulis, Prunus serotina +5 more
Belongs to 4
apple, plum, apricot, peach
Has part(s) 4
hydrogen, oxygen, carbon, nitrogen
Has characteristic 2
odor, bitterness
Described by source 1
Brockhaus and Efron Encyclopedic Dictionary
Part of 1
almond
Press Enter · cited answer in seconds

Summary

(R)-amygdalin is a type of chemical entity[1]. (R)-amygdalin is a type of (RS)-amygdalin[2].

Key Facts

  • 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[3]
  • Chemical formula: C₂₀H₂₇NO₁₁[4]
  • Part of: amygdalin beta-glucosidase activity[5], apple seed[6], almond[7]
  • Has part(s): oxygen[8], carbon[9], nitrogen[10], hydrogen[11]
  • Found in taxon: Gerbera jamesonii[12], Malus[13], Oxyanthus pyriformis[14], Passiflora edulis[15], Prunus armeniaca[16], Prunus cerasus[17], Prunus domestica[18], Prunus persica[19], Prunus salicina[20], Prunus serotina[21], Prunus spinosa[22], Prunus dulcis[23], Distimake tuberosus[24], Eucalyptus camphora[25]
  • Described by source: Encyclopedic Lexicon[26], Great Soviet Encyclopedia (1926–1947)[27], Brockhaus and Efron Encyclopedic Dictionary[28], Small Brockhaus and Efron Encyclopedic Dictionary[29]
  • Has characteristic: bitterness[30], odor[31]
  • NCI Thesaurus ID: C28801[32]
  • Isomeric SMILES: OC[C@H]1OC@@HC@HC@@H[C@@H]1OC@@HC@HC@@H[C@@H]1O">[33]
  • Mass: 457.158411 dalton[34]
  • Subject has role: phytogenic antineoplastic agents[35]
  • Stereoisomer of: Neoamygdalin[36], (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[37]
  • Safety classification and labelling: NFPA 704: Standard System for the Identification of the Hazards of Materials for Emergency Response[38]

References

Programmatic citations — every numbered marker resolves to a verifiable graph row below.

Direct Wikidata claims

  1. [3] ↑ . PubChem. Retrieved . wikidata.org.
  2. [4] ↑ . PubChem. Retrieved . wikidata.org.
  3. [2] ↑ . wikidata.org.
  4. [5] ↑ . Gene Ontology release 2020-05-02. wikidata.org.
  5. [6] ↑ . wikidata.org.
  6. [7] ↑ . wikidata.org.
  7. [8] ↑ . wikidata.org.
  8. [9] ↑ . wikidata.org.
  9. [10] ↑ . wikidata.org.
  10. [11] ↑ . wikidata.org.
  11. [12] ↑ . Cyanogenic glycosides and 4-hydroxycoumarin glycosides from Gerbera jamesonii hybrida.. wikidata.org.
  12. [13] ↑ . Cyclooxygenase inhibitory and antioxidant compounds from crabapple fruits. wikidata.org.
  13. [14] ↑ . Cyanogenic glycosides from PS Psydrax and Oxyanthus species[a/t]. wikidata.org.
  14. [15] ↑ . Identification and Quantification of Passion Fruit Cyanogenic Glycosides. wikidata.org.
  15. [16] ↑ . Micellar electrokinetic chromatography for the analysis of d-amygdalin and its epimer in apricot kernel. wikidata.org.
  16. [17] ↑ . Quantification of benzaldehyde and its precursors in montmorency cherry (Prunus cerasus L.) kernels. wikidata.org.
  17. [18] ↑ . Tissue Level Compartmentation of (R)-Amygdalin and Amygdalin Hydrolase Prevents Large-Scale Cyanogenesis in Undamaged Prunus Seeds. wikidata.org.
  18. [19] ↑ . Anti-tumor promoting effect of glycosides from Prunus persica seeds. wikidata.org.
  19. [20] ↑ . Changes in Cyanogenic Glycoside Content and ^|^beta;-Cyanoalanine Synthase Activity in Flesh and Seeds of Japanese Plum (Prunus salicina Lindl.) during Development. wikidata.org.
  20. [21] ↑ . Tissue and Subcellular Localization of Enzymes Catabolizing (R)-Amygdalin in Mature Prunus serotina Seeds. wikidata.org.
  21. [22] ↑ . Cyanogenic glycosids from Prunus spinosa (Rosaceae). wikidata.org.
  22. [23] ↑ . wikidata.org.
  23. [24] ↑ . Amygdalin acyl derivatives, cyanogenic glycosides from the seeds of Merremia dissecta. wikidata.org.
  24. [25] ↑ . Novel aspects of cyanogenesis in Eucalyptus camphora subsp. humeana. wikidata.org.
  25. [26] ↑ . wikidata.org.
  26. [27] ↑ . wikidata.org.
  27. [28] ↑ . wikidata.org.
  28. [29] ↑ . wikidata.org.
  29. [30] ↑ . wikidata.org.
  30. [31] ↑ . wikidata.org.
  31. [32] ↑ . Global Substance Registration System. Retrieved . wikidata.org.
  32. [33] ↑ . Global Substance Registration System. Retrieved . wikidata.org.
  33. [34] ↑ . PubChem. Retrieved . wikidata.org.
  34. [35] ↑ . Medical Subject Headings. Retrieved . wikidata.org.
  35. [36] ↑ . wikidata.org.
  36. [37] ↑ . wikidata.org.
  37. [38] ↑ . wikidata.org.

Class ancestry

  1. [1] ↑ . Wikidata. wikidata.org.

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Use these citations when quoting this entity in research, articles, AI prompts, or wherever provenance matters. We aggregate Wikidata + Wikipedia + authoritative open-data sources; the stitched, scored, cross-referenced view is what 4ort.xyz contributes.

APA 4ort.xyz Knowledge Graph. (2026). (R)-amygdalin. Retrieved November 11, 2026, from https://4ort.xyz/entity/r-amygdalin
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BibTeX @misc{4ortxyz_r-amygdalin_2026, author = {{4ort.xyz Knowledge Graph}}, title = {{(R)-amygdalin}}, year = {2026}, url = {https://4ort.xyz/entity/r-amygdalin}, note = {Accessed: 2026-11-11}}
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Edit History

Rolling log of changes to this entity's Wikidata record. Values shown reflect the current state of each edited property — follow the history link to see the precise diff for any edit.

  1. 24w ago · Twofivesixbot bot · 2026-05-25 view diff on Wikidata ↗
    Subclass of → (RS)-amygdalin
    Subject has role → phytogenic antineoplastic agents
    Safety classification and labelling → NFPA 704: Standard System for the Identification of the Haza
    Part of → amygdalin beta-glucosidase activity, apple seed, almond
    + 8 other properties edited (see Wikidata diff for full list)
    "Changed claim qualifiers: J9U entity ID: 987007550882505171, mv to monolingual text names on J9U statements"
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