| Identification | Back Directory | [Name]
5'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE | [CAS]
3031-94-5 | [Synonyms]
ZMP
NSC 283955
NSC 292227
Acaribonucleotide
aicaribonucleotide
AICAR MONOPHOSPHATE
AICA-Riboside, 5′-Phosphate
5-Amino-4-imidazolecarboxamide ribonucleotide
5'-Phosphoribosyl-4-carboxamide-5-aminoimidazole
N1-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide
5-Aminoimidazole-4-Carboxamide-1-b-D-Ribofuranosyl 5Monophosphate
5-Aminomidazole-4-carboxamide-1-β-D-ribofuranosyl 5-Monophosphate
5-Aminoimidazole-4-carboxamide-1-b-D-ribofuranose 5'-monophosphate
5-aminoimidazole-4-carboxamide-1-β-d-ribofuranosyl 5'-monophosphate
5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
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'-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATE
5-Aino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide
5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5'-monophosphate ,98%
5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide
AICAR MONOPHOSPHATE, N1-[BETA-D-5'-PHOSPHORIBOFURANOSYL]-5-AMINOIMIDAZOLE-4-CARBOXAMIDE
AICAR monophosphate, ZMP, N1-(β-D-5μ-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide
[(2R,3R,4R,5R)-5-(5-amino-4-carbamoyl-imidazol-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxyphosphonic acid
((2R,3S,4R,5R)-5-(5-aMino-4-carbaMoyl-1H-iMidazol-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)Methyl dihydrogen phosphate | [EINECS(EC#)]
221-212-1 | [Molecular Formula]
C9H15N4O8P | [MDL Number]
MFCD00057264 | [MOL File]
3031-94-5.mol | [Molecular Weight]
338.21 |
| Chemical Properties | Back Directory | [Appearance]
White Powder With Pink Tinge. | [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 | [Water Solubility ]
water: 1mg/mL
DMSO: 30mg/mL | [Stability:]
Hygroscopic | [InChIKey]
UDYDDOATBNVEES-UUOKFMHZSA-N |
| Hazard Information | Back Directory | [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. | [storage]
-20°C |
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