A1393

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

≥93%

• Sinónimos: AICAR monophosphate, N¹-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide, NSC 283955, NSC 292227, ZMP
• Fórmula empírica (notación de Hill): C₉H₁₅N₄O₈P
• Número de CAS: 3031-94-5
• Peso molecular: 338.21
• Número CE: 221-212-1
• Número MDL: MFCD23726600
• Código UNSPSC: 41106305
• ID de la sustancia en PubChem: 24890538
• NACRES: NA.51

Propiedades

• Nivel de calidad: 200
• Ensayo: ≥93%
• Formulario: powder
• mol peso: 338.21 g/mol
• temp. de almacenamiento: −20°C
• cadena SMILES: 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
• Clave InChI: NOTGFIUVDGNKRI-UUOKFMHZSA-N

Descripción

Descripción general

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.

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: Eyeshields, Gloves, type N95 (US)