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A1393 Sigma-Aldrich

5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate


Synonym: AICAR monophosphate, N1-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide, NSC 283955, NSC 292227, ZMP

  • CAS Number 3031-94-5

  • Empirical Formula (Hill Notation) C9H15N4O8P

  • Molecular Weight 338.21

  •  EC Number 221-212-1

  •  PubChem Substance ID 24890538



Related Categories Cell Biology, Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Metabolomics, Nucleotide More...
Quality Level   200
assay   ≥93%
storage temp.   −20°C
SMILES string   O[C@H]1[C@@H](O)[C@H](N2C=NC(C(N)=O)=C2N)O[C@@H]1COP(O)(O)=O
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


General description

5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5′-monophosphate (AICAR), a natural metabolic intermediate of purine biosynthesis, is usually found in all organisms. It is produced from succinyl-AICAR (SAICAR) with the help of adenylosuccinate lyase (ASL) enzyme.


5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate has been used in the study to explore the anticancer effect of nine statins in breast cancer and glioblastoma.

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.


50, 100 mg in poly bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A1393.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles


MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Mitochondrial Dysfunction and Metabolic Defects

Defects in mitochondrial function are associated with insulin resistance in both human and animal studies. Insulin resistance is associated with a decrease in the number, oxidative capacity, size, an...
Keywords: Acetylations, Apoptosis, Biofiles, Cancer, Carboxylations, Catalog, Catalysis, Citric Acid Cycle, Decarboxylations, Degradations, Diabetes, Enzyme-linked immunosorbent assay, Glycolysis, Immunofluorescence, Immunohistochemistry, Lipid Metabolism, Metabolism, Metabolites, Neurotransmitters, Obesity, Oxidations, Phosphorylations, Physiological Processes, Protocols, Transcription, Transduction, Transfection, Western blot

Peer-Reviewed Papers


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