A1393

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

≥93%

• Synonyme(s) : AICAR monophosphate, N¹-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide, NSC 283955, NSC 292227, ZMP
• Formule empirique (notation de Hill) : C₉H₁₅N₄O₈P
• CAS Number: 3031-94-5
• Poids moléculaire : 338.21
• Numéro CE : 221-212-1
• Numéro MDL: MFCD23726600
• Code UNSPSC : 41106305
• ID de substance PubChem : 24890538
• Nomenclature NACRES : NA.51

Propriétés

• Niveau de qualité: 200
• Essai: ≥93%
• Forme: powder
• Poids mol.: 338.21 g/mol
• Température de stockage: −20°C
• Chaîne 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
• Clé InChI: NOTGFIUVDGNKRI-UUOKFMHZSA-N

Description

Description générale

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.

Application

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.

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)