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152-93-2

152-93-2 Structure

152-93-2 Structure
IdentificationBack Directory
[Name]

2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one
[CAS]

152-93-2
[Synonyms]

Vicioside
NSC 95092
VICINE(SH)
Vicine【phytotoxin】
Divicine β-D-glucopyranoside
Divicine beta-D-glucopyranoside
Divicine 5-(β-D-glucopyranoside
Glucopyranoside,divicine-5,.β.-D-
2,6-Diamino-5-(β-D-glucopyranosyloxy)pyrimidin-4-ol
2,6-Diamino-5-(β-D-glucopyranosyloxy)-4(1H)-pyrimidinone
4(1H)-Pyrimidinone, 2,6-diamino-5-(β-D-glucopyranosyloxy)-
2,6-Diamino-5-(beta-D-glucopyranosyloxy)-4(1H)-pyrimidinone
2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one
2,4-Diamino-6-oxo-1,6-dihydro-5-pyrimidinyl β-D-glucopyranoside
2,6-diamino-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1H-pyrimidin-4-one
[EINECS(EC#)]

205-809-4
[Molecular Formula]

C10H16N4O7
[MDL Number]

MFCD00270447
[MOL File]

152-93-2.mol
[Molecular Weight]

304.257
Chemical PropertiesBack Directory
[Melting point ]

242-244℃
[alpha ]

D26 -11.7° (c = 3.9 in 0.2N NaOH)
[Boiling point ]

445.09°C (rough estimate)
[density ]

2.18
[refractive index ]

1.6200 (estimate)
[solubility ]

Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
[form ]

neat
[pka]

9.56±0.50(Predicted)
[color ]

White to off-white
[BRN ]

44407
[Stability:]

Hygroscopic
[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
[InChIKey]

KGNGTSCIQCLKEH-SYCVNHKBSA-N
[SMILES]

O[C@@H]1[C@@H](O)[C@H](OC2=C(N)NC(N)=NC2=O)O[C@H](CO)[C@H]1O
Safety DataBack Directory
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Hazard InformationBack Directory
[Uses]

Vicine is a pyrimidine glycosides, a precursor of the aglycons divicine and isouramil which is main factors of favism. It is found in faba/fava bean. Also, it is derived from Ethyl Glyoxylate (E918550), which is used as a reagent in the synthesis of a new class of cinnamyl-triazole compounds which can be used as selective inhibitors of human aromatase (cytochrome P 450 19A1)
[Definition]

ChEBI: Vicine is a glycoside.
[in vivo]

"High levels" of Vicine might have shortened the birds' survival time by enhancing the neurotoxicity induced by "lower levels" of BCA[1].

[Purification Methods]

Crystallise Vicine from water (1%) or aqueous 85% EtOH, and dry it at 135o. [Bendich & Clements Biochim Biophys Acta 12 462 1953, Beilstein 31 H 163, 2 5 III/IV 4285.]
Spectrum DetailBack Directory
[Spectrum Detail]

2,6-diamino-5-(beta-D-glucopyranosyloxy)-(1H)-pyrimidin-4-one(152-93-2)1HNMR
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