5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE Chemical Properties

Melting point:

198-202°C dec.

Boiling point:

845.3±75.0 °C(Predicted)

Density 

2.30±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO (Slightly, Heated, Sonicated), Methanol (Slightly), Water (Slightly)

pka

1.86±0.10(Predicted)

form 

White to light pink solid

color 

White to Pink

optical activity

[α]/D -69.0±3.0°, c = 0.1 in sodium bicarbonate

Stability:

Hygroscopic

InChIKey

UDYDDOATBNVEES-UUOKFMHZSA-N

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich

5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE Usage And Synthesis

Chemical Properties

White Powder With Pink Tinge.

Uses

AICAR monophosphate is a 5′′-phosphorylated analog of cell permeable AICAR that mimics AMP. AICAR is an adenosine monophophate (AMP)-activated protein kinase (AMPK) activator/agonist.

Definition

ChEBI: AICA ribonucleotide is a 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative. It has a role as a cardiovascular drug, a plant metabolite, a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is a 1-(phosphoribosyl)imidazolecarboxamide and an aminoimidazole. It is functionally related to an acadesine. It is a conjugate acid of a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide(2-).

General Description

5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate (AICAR monophosphate) is an intermediate metabolite in the purine de novo synthesis pathway and a potent activator of the human AMP-activated protein kinase (AMPK) activity in vitro. It can play an important regulatory role.

Biochem/physiol Actions

A 5′-phosphorylated analog of cell permeable AICAR that mimics adenosine monophosphate (AMP). It is an AMP-activated protein kinase (AMPK) activator.In humans, 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate (AICAR) is found to be accumulated in numerous metabolic diseases. It can increase the endurance of sedentary mice. AICAR exhibits antiproliferative effects. It can induce apoptosis of aneuploid cells.

5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE(3031-94-5)Related Product Information

• AICAR
• 5-Amino-4-imidazolecarboxamide
• 5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
• 3-ETHYL-3H-IMIDAZOLE-4-CARBALDEHYDE