Description

AICAR (5-Aminoimidazole-4-carboxamide ribonucleotide) is a pivotal intermediate in the de novo purine biosynthesis pathway, serving as a precursor to inosine monophosphate (IMP). This biologically active ribonucleotide, with the molecular formula C₉H₁₅N₄O₈P (CAS: 3031-94-5), is widely utilized in biochemical research for its role as an AMP-activated protein kinase (AMPK) activator, mimicking the effects of cellular energy depletion. Its high purity (≥93%) ensures reliability for studies in metabolic regulation, ischemia-reperfusion injury, and muscle physiology. Available as a lyophilized powder or in solution, AICAR is rigorously tested via HPLC and NMR to meet stringent quality standards for reproducibility in in vitro and in vivo applications. Store at -20°C to maintain stability.

Properties

• CAS Number: 3031-94-5
• Complexity: 475
• IUPAC Name: [(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-imidazol-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
• InChI: InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
• InChI Key: NOTGFIUVDGNKRI-UUOKFMHZSA-N
• Exact Mass: 338.06275045
• Molecular Formula: C9H15N4O8P
• Molecular Weight: 338.21
• SMILES: C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N
• Topological: 203
• Monoisotopic Mass: 338.06275045
• Physical Description: Solid
• Synonyms: AICA ribonucleotide, 3031-94-5, Z-nucleotide, aminoimidazole carboxamide ribonucleotide, 5′-Phosphoribosyl-5-amino-4-imidazolecarboxamide, 5-amino-4-imidazolecarboxamide ribotide, Acadesine 5′-monophosphate, AICA-ribonucleotide, EINECS 221-212-1, 1-(5′-Phosphoribosyl)-5-amino-4-imidazolecarboxamide, F0X88YW0YK, 5-Amino-4-imidazole carboxamide ribonucleotide, NSC 283955, NSC 292227, 5-Aminoimidazole-4-carboxamide ribotide, CHEBI:18406, 5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole, 5-Amino-4-imidazolecarboxamide ribonucleoside 5′-monophosphate, AICAR [MART.], 5′-Phospho-ribosyl-5-amino-4-imidazole carboxamide, 5′-P-ribosyl-5-amino-4-imidazole carboxamide, 5′-phosphoribosyl-5-amino-4-imidazole carboxamide, 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide, NSC-283955, NSC-292227, {[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid, AICAR (MART.), Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, 5′-(dihydrogen phosphate), [(2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate, AICA-Ribotide, (((2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)phosphonic acid, ((2R,3S,4R,5R)-5-(4-Carbamoyl-5-Aminoimidazol-1-yl)-3,4-Dihydroxyoxolan-2-yl)Methyl Dihydrogen Phosphate, ((2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl dihydrogen phosphate, [(2R,3S,4R,5R)-5-(4-Carbamoyl-5-Aminoimidazol-1-yl)-3,4-Dihydroxyoxolan-2-yl]Methyl Dihydrogen Phosphate, 5-aminoimidazole-4-carboxamide ribonucleotide, Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, 5′-(dihydrogen phosphate) (8CI), 4-carboxy-5-aminoimidazole ribotide, 5-amino-1-beta-d-ribofuranosylimidazole-4-carboxamide monophosphate, 5-amino-4-imidazolecarboxamide ribofuranoside 5′-monophosphate, aicariboside 5′-monophosphate, AICAR monophosphate, 5′-Aminoimidazole-4-carboxamide-1-beta-d-ribofuranosyl 5′-monophosphate, 5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide, AICA-Riboside, 5′-Phosphate, CHEMBL483849, AMINOIMIDAZOLE 4-CARBOXAMIDE RIBONUCLEOTIDE, AMZ, UNII-F0X88YW0YK, AICA Ribotide, 1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-.beta.-D-ribofuranosyl)-, 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide, AICAR monophosphate;ZMP, SCHEMBL1230585, BDBM22579, DTXSID10904363, MSK15375, AKOS027326505, DB01700, NA07204, Aminoimidazole-4-carboxamide ribonucleotide, 5-Amino-4-imidazolecarboxamide ribonucleotide, NS00015007, C04677, G77032, Q2817102, 5′-Phospho-b-D-ribosyl-5-amino-4-imidazolecarboxamide, 5-Amino-1-(5′-phosphofuranoribosyl)-4-imidazolecarboxamide, 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide 5′-phosphate, 5-Aminoimidazole-4-carboxamide-1-?-D-Ribofuranosyl 5′-Monophosphate, 5-Amino-1-(5-O-phosphono-b-D-ribofuranosyl)-1H-imidazole-4-carboxamide, 5-Aminoimidazole-4-carboxamide-1-.beta.D-ribofuranosyl 5′-monophosphate, 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5”-monophosphate, 1H-Imidazole-4-carboxamide, 5-amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-(9Cl), 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5′-monophosphate, >=93%, Imidazole-4-carboxamide, 5-amino-1-b-D-ribofuranosyl-, 5′-phosphate (6CI,7CI), Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, 5′-(dihydrogen phosphate) (8Cl), 5-Aminoimidazole-4-carboxamide-1-|A-D-ribofuranosyl 5 inverted exclamation marka-monophosphate

AICAR is extensively used in metabolic research to study AMPK signaling pathways due to its ability to induce AMPK activation without altering cellular ATP levels. It has applications in investigating glucose uptake, lipid metabolism, and mitochondrial biogenesis in skeletal muscle and adipose tissue. Researchers also employ AICAR to explore its cardioprotective effects in ischemia-reperfusion models and its potential in cancer metabolism studies.

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