Vicine

Vicine
IUPAC name 2,6-diamino-5-[(2S,3R,4S,5S,6R)- 3,4,5-trihydroxy-6-(hydroxymethyl)- 2-tetrahydropyranyl]oxy]-1H- pyrimidin-4-one
Identifiers
CAS number	152-93-2
PubChem	91446
ChemSpider	82575 Y
Jmol-3D images	Image 1
SMILES O=C2\N=C(\N)NC(=C2/O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)/N
InChI InChI=1S/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1 Y Key: KGNGTSCIQCLKEH-SYCVNHKBSA-N Y InChI=1/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1 Key: KGNGTSCIQCLKEH-SYCVNHKBBM
Properties
Molecular formula	C10H16N4O7
Molar mass	304.25 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Vicine is an alkaloid glycoside found in fava beans. Vicine is toxic, causing the disease favism, in individuals who have a hereditary loss of the enzyme glucose-6-phosphate dehydrogenase. Divicine is the name of the aglycone of vicine. Fava beans also contain the related 6-hydroxy- alkaloid glycoside covicine, whose aglycone is isouramil.

External links

• Cornell U. page on vicine