06595

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

analytical standard

• Synonym(s): AICAR monophosphate, N¹-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide, NSC 283955, NSC 292227, ZMP
• Empirical Formula (Hill Notation): C₉H₁₅N₄O₈P
• CAS Number: 3031-94-5
• Molecular Weight: 338.21
• EC Number: 221-212-1
• UNSPSC Code: 41116107
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• assay: ≥98.0% (HPLC)
• optical activity: [α]/D -69.0±3.0°, c = 0.1 in sodium bicarbonate
• shelf life: limited shelf life, expiry date on the label
• application(s): forensics and toxicology; pharmaceutical (small molecule)
• format: neat
• 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
• InChI key: NOTGFIUVDGNKRI-UUOKFMHZSA-N

Description

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable