CAS 93839-87-3

Uridine, adenylyl-(3′→5′)-, ammonium salt (1:1)

Description:

Uridine, adenylyl-(3′→5′)-, ammonium salt (1:1), commonly referred to as cyclic AMP (cAMP) when in its active form, is a nucleotide derivative that plays a crucial role in cellular signaling. This compound is characterized by its cyclic structure, which consists of a ribose sugar, a phosphate group, and the nitrogenous base adenine. The ammonium salt form indicates that it is paired with an ammonium ion, which can enhance its solubility in aqueous solutions. cAMP is a secondary messenger involved in various biological processes, including the regulation of glycogen, sugar, and lipid metabolism. It is synthesized from ATP by the enzyme adenylate cyclase and is degraded by phosphodiesterases. The compound is typically stable under physiological conditions but can be sensitive to hydrolysis, particularly in the presence of certain enzymes. Its role in signal transduction pathways makes it a vital component in the functioning of hormones and neurotransmitters, influencing processes such as cell growth, differentiation, and apoptosis.

Formula: C₁₉H₂₄N₇O₁₂P·H₃N

InChI: InChI=1S/C19H24N7O12P.H3N/c20-15-10-16(22-5-21-15)26(6-23-10)18-13(31)14(7(3-27)36-18)38-39(33,34)35-4-8-11(29)12(30)17(37-8)25-2-1-9(28)24-19(25)32;/h1-2,5-8,11-14,17-18,27,29-31H,3-4H2,(H,33,34)(H2,20,21,22)(H,24,28,32);1H3/t7-,8-,11-,12-,13-,14-,17-,18-;/m1./s1

InChI key: InChIKey=PRPZHNJNQXWARV-ANTYETTRSA-N

SMILES: O[C@H]1[C@H](N2C=3C(N=C2)=C(N)N=CN3)O[C@H](CO)[C@H]1OP(OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N5C(=O)NC(=O)C=C5)(=O)O.N

Synonyms:

• Adenosine, uridylyl-(5′→3′)-, monoammonium salt
• Uridine, adenylyl-(3′→5′)-, monoammonium salt
• Uridine, adenylyl-(3′→5′)-, ammonium salt (1:1)

Adenylyl-3'-5'-uridine ammonium salt

CAS: 93839-87-3

Adenylyl-3'-5'-uridine ammonium salt is a novel antiviral agent that has been shown to inhibit the activity of viral DNA polymerase, RNA polymerase and reverse transcriptase. It is also an anticancer agent that can be used as a cytotoxic agent against leukemia and lymphoma cells. Adenylyl-3'-5'-uridine ammonium salt is synthesized by the reaction of adenosine monophosphate with uracil in the presence of phosphate and ammonia. This compound can then be converted to ribonucleosides or deoxyribonucleosides by phosphorylation.
SYNONYMS: AMP-uridine; AMP-U; UMP

Formula: C₁₉H₂₄N₇O₁₂P

Purity: Min. 95%

Molecular weight: 573.41 g/mol

Ref: 3D-NA46045