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

SIGMA/A1393 - ≥93%

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
MDL Number: MFCD23726600
Linear Formula: C9H15N4O8P
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-A1393-50MG 50 mg
 $769.00
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45-A1393-100MG 100 mg
 $1360.00
1/EA		 Add To Favorites
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A1393-100MG

 

assay ≥93%
form powder
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
mol wt 338.21  g/mol
Quality Level 200 
SMILES string O[C@H]1[C@@H](O)[C@H](N2C=NC(C(N)=O)=C2N)O[C@@H]1COP(O)(O)=O
storage temp. −20°C
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.
Application: 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.
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.
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.
Packaging: 50, 100 mg in poly bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥93%
Storage Temp. −20°C
UNSPSC 41106305

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