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

5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE Basic information
Product Name:5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
Synonyms:AICAR monophosphate, ZMP, N1-(β-D-5μ-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide;1-(5-O-Phosphono-β-D-ribofuranosyl)-5-amino-1H-imidazole-4-carboxamide;5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide;5-Amino-4-imidazolecarboxamide ribonucleotide;5'-Phosphoribosyl-4-carboxamide-5-aminoimidazole;ZMP;5-Aino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide;5-Aminomidazole-4-carboxamide-1-β-D-ribofuranosyl 5-Monophosphate
CAS:3031-94-5
MF:C9H15N4O8P
MW:338.21
EINECS:221-212-1
Product Categories:Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides
Mol File:3031-94-5.mol
5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE Structure
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)
form White to light pink solid
pka1.86±0.10(Predicted)
color White to Pink
optical activity[α]/D -69.0±3.0°, c = 0.1 in sodium bicarbonate
Stability:Hygroscopic
InChIKeyUDYDDOATBNVEES-UUOKFMHZSA-N
Safety Information
Safety Statements 24/25
WGK Germany 3
HS Code 29349990
MSDS Information
ProviderLanguage
SigmaAldrich English
5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE Usage And Synthesis
Chemical PropertiesWhite Powder With Pink Tinge.
UsesAICAR 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.
DefinitionChEBI: 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 Description5-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 ActionsA 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 Preparation Products And Raw materials
AICAR 3-ETHYL-3H-IMIDAZOLE-4-CARBALDEHYDE 5-Amino-4-imidazolecarboxamide 5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE

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