5-Aminouridine

Category	Influenza Virus
CAS	2149-76-0
Description	5-Aminouridine can modify nucleobases and can be incorporated into the target DNA. It therefore exhibits a wide range of biological activity and it inhibits the growth of tumors, fungi and viruses.

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Synonyms	5-Amino Uridine; 5-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione; 5-Amino-1-β-D-ribofuranosyl-2,4(1H,3H)-pyrimidinedione; NSC 72560
IUPAC Name	5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Molecular Weight	259.22
Molecular Formula	C9H13N3O6
Canonical SMILES	C1=C(C(=O)NC(=O)N1C2C(C(C(O2)CO)O)O)N
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
Melting Point	214-216°C
Purity	≥95%
Density	1.712±0.06 g/cm3 (Predicted)
Solubility	Soluble in Methanol (Slightly, Heated), Water (Slightly, Sonicated)
Appearance	Off-white to Yellow Powder
Storage	Store at -20°C
Complexity	411
Exact Mass	259.08000
Index Of Refraction	1.666
In Vitro	This modified nucleobase, 5-Aminouridine, can 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 incorporation of carbamylaspartate into pyrimidines of both RNA and DNA in rat lived and [32P]phosphate into phospholipids and RNA nucleotides of rat liver slices and hepatoma.
PSA	150.80000
Target	Fungal; Influenza Virus
XLogP3-AA	-2.5