5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
Synonym(s):AICAR monophosphate;AICA-Ribotide, AICAr Monophosphate, ZMP, AMPK Signaling Activator IV;N1-(β-D -5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide;ZMP
- CAS NO.:3031-94-5
- Empirical Formula: C9H15N4O8P
- Molecular Weight: 338.21
- MDL number: MFCD00057264
- EINECS: 221-212-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 08:26:49
What is 5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE?
Chemical properties
White Powder With Pink Tinge.
The Uses of 5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
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.
What are the applications of Application
AICA-Riboside, 5′-Phosphate is an AMP-activated protein kinase (AMPK) activator mimic
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.
Properties of 5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
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 |
pka | 1.86±0.10(Predicted) |
color | White to Pink |
optical activity | [α]/D -69.0±3.0°, c = 0.1 in sodium bicarbonate |
Stability: | Hygroscopic |
Safety information for 5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
Computed Descriptors for 5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
InChIKey | UDYDDOATBNVEES-UUOKFMHZSA-N |
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