| Identification | Back Directory | [Name]
5-AMINOURIDINE, HYDROCHLORIDE SALT | [CAS]
2149-76-0 | [Synonyms]
5-aminouridine
Uridine, 5-amino-
5-Aminouridine Hcl
5-AminouridineHClsalt
Uridine, 5-amino-(6CI,7CI,8CI,9CI)
5-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
5-azanyl-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
5-amino-1-(3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl)pyrimidine-2,4-quinone
5-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione | [Molecular Formula]
C9H13N3O6 | [MDL Number]
MFCD00058224 | [MOL File]
2149-76-0.mol | [Molecular Weight]
259.22 |
| Chemical Properties | Back Directory | [Melting point ]
214-216 °C | [density ]
1.712±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [pka]
9.31±0.10(Predicted) | [InChI]
InChI=1S/C9H13N3O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2,10H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1 | [InChIKey]
YBTWWWIJBCCYNR-UAKXSSHOSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C=C(N)C(=O)NC2=O)[C@H](O)[C@@H]1O |
| Hazard Information | Back Directory | [Description]
5-Aminouridine can modify nucleobases and can be incorporated into the target DNA. 5-Aminouridine exhibits a wide range of biological activity and it inhibits the growth of tumors, fungi and viruses.
| [in vitro]
This modified nucleobase, 5-Aminouridine, must exhibit a low enough potential to be oxidized by Os(bpy)33+. These modified nucleobases can be inserted into the target DNA by direct synthesis using modified phosphoramidites
| [in vivo]
5-Aminouridine inhibits the incorporation of carbamyl aspartate into pyrimidines of both RNA and DNA in rat lived and [32P]phosphate into phospholipids and RNA nucleotides of rat liver slices and hepatoma. 5-Aminouridine was found to be incorporated into the RNA of Ehrlich ascites cells, and 5-aminouridine monophosphate was shown to be a strong inhibitor of orotidine 5'-phosphate decarboxylase[1].
| [References]
[1] David A. Smith, Donald W. Visser, P. Roy-Burman. “Studies on 5-aminouridine.” Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis 119 2 (1966): Pages 221-228. |
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