Structure via PubChem · Public domain (PubChem)
Vicianin
Sign in to saveVicianin is a cyanogenic disaccharide.
Chemical data
- Formula
- C19H25NO10
- Molecular weight
- 427.4 g/mol
- IUPAC name
- (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
- SMILES
- C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H](C#N)C3=CC=CC=C3)O)O)O)O)O)O
- InChIKey
- YYYCJNDALLBNEG-GNRUMFBNSA-N
- XLogP
- -2.6
- Polar surface area
- 182 Ų
- H-bond donors
- 6
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 427.147846
Show 4 more facts
- canonical SMILES
- C1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(C#N)C3=CC=CC=C3)O)O)O)O)O)O
- chemical formula
- C₁₉H₂₅NO₁₀
- isomeric SMILES
- C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H](C#N)C3=CC=CC=C3)O)O)O)O)O)O
- found in taxon
- Vicia sativa
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
{{chembox | Watchedfields = changed | verifiedrevid = 441557672 | Name = Vicianin | ImageFile = Vicianin.svg | ImageName = Chemical structure of vicianin | ImageAlt = Chemical structure of vicianin | IUPACName = (R)-[α--Arabinopyranosyl-(1→6)-β--glucopyranosyloxy](phenyl)acetonitrile | SystematicName = (R)-Phenyl{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile | OtherNames = (R)-Vicianin6-O-Arabinopyranosylglucopyranosideβ-Vicianoside |Section1= |Section2= |Section8= }} Vicianin is a cyanogenic disaccharide.
The enzyme vicianin beta-glucosidase uses (R)-vicianin and H2O to produce mandelonitrile and vicianose. It is found in seeds of Vicia angustifolia.
Excerpted from Wikipedia’s “Vicianin” article, available under the CC BY-SA 4.0 licence.