Structure via PubChem · Public domain (PubChem)
vicine
Sign in to saveVicine is an alkaloid glycoside found mainly in fava beans, which are also called broad beans (Vicia faba). Vicine is toxic in individuals who have a hereditary loss of the enzyme glucose-6-phosphate dehydrogenase. It causes haemolytic anaemia, called favism. The formation of vicine in Vicia faba has been studied, but this natural formation has not yet been found.
Chemical data
- Formula
- C10H16N4O7
- Molecular weight
- 304.26 g/mol
- IUPAC name
- 2,6-diamino-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyrimidin-4-one
- SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(NC(=NC2=O)N)N)O)O)O)O
- InChIKey
- KGNGTSCIQCLKEH-SYCVNHKBSA-N
- XLogP
- -3.7
- Polar surface area
- 193 Ų
- H-bond donors
- 7
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- alkaloid
- Mass
- 304.101899
Show 5 more facts
- chemical formula
- C₁₀H₁₆N₄O₇
- isomeric SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(NC(=NC2=O)N)N)O)O)O)O
- canonical SMILES
- C(C1C(C(C(C(O1)OC2=C(NC(=NC2=O)N)N)O)O)O)O
- found in taxon
- Vicia narbonensis
- Commons category
- Vicine
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
8 sectionsContents
- History
- Metabolism
- Adverse effects
- Indications
- Toxicity
- Effects on animals
- References
- External links
{{chembox | Verifiedfields = changed | verifiedrevid = 470630004 | ImageFile=vicin.svg | ImageSize=200px | IUPACName = 2,6-Diamino-5-(β--glucopyranosyloxy)pyrimidin-4(1H)-one | SystematicName = 2,6-Diamino-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pyrimidin-4(1H)-one | OtherNames= |Section1= |Section2= |Section3= }}
Vicine is an alkaloid glycoside found mainly in fava beans, which are also called broad beans (Vicia faba). Vicine is toxic in individuals who have a hereditary loss of the enzyme glucose-6-phosphate dehydrogenase. It causes haemolytic anaemia, called favism. The formation of vicine in Vicia faba has been studied, but this natural formation has not yet been found.
Excerpted from Wikipedia’s “vicine” article, available under the CC BY-SA 4.0 licence.