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Merck

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

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About This Item

Empirical Formula (Hill Notation):
C9H15N4O8P
CAS Number:
3031-94-5
Molecular Weight:
338.21
NACRES:
NA.24
UNSPSC Code:
41116107
EC Number:
221-212-1

Product Name

5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate, analytical standard

InChI key

NOTGFIUVDGNKRI-UUOKFMHZSA-N

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

SMILES string

O[C@H]1[C@@H](O)[C@H](N2C=NC(C(N)=O)=C2N)O[C@@H]1COP(O)(O)=O

grade

analytical standard

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

Quality Level

100

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3111
BCCK9965
BCCH3904
BCCH1802
BCCD5724

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Hans P M M Lauritzen et al.
Diabetes, 62(9), 3081-3092 (2013-06-14)
Recent studies suggest that interleukin 6 (IL-6) is released from contracting skeletal muscles; however, the cellular origin, secretion kinetics, and signaling mechanisms regulating IL-6 secretion are unknown. To address these questions, we developed imaging methodology to study IL-6 in fixed
Hiroyasu Hatakeyama et al.
Molecular biology of the cell, 24(6), 809-817 (2013-01-18)
Tbc1d1 is key to skeletal muscle GLUT4 regulation. By using GLUT4 nanometry combined with a cell-based reconstitution model, we uncover a shift in the regulatory mode of Tbc1d1 by showing that Tbc1d1 temporally acquires insulin responsiveness, which triggers GLUT4 trafficking
Melissa M Thomas et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 28(5), 2098-2107 (2014-02-14)
AMP-activated protein kinase (AMPK) is a master regulator of metabolism. While muscle-specific AMPK β1β2 double-knockout (β1β2M-KO) mice display alterations in metabolic and mitochondrial capacity, their severe exercise intolerance suggested a secondary contributor to the observed phenotype. We find that tibialis
Janine Dokas et al.
Endocrinology, 154(10), 3502-3514 (2013-07-31)
In the obesity-resistant SJL mouse strain, we previously identified a naturally occurring loss-of-function mutation in the gene for Tbc1d1. Characterization of recombinant inbred mice that carried the Tbc1d1(SJL) allele on a C57BL/6J background indicated that loss of TBC1D1 protects from
5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate (AICAR), a highly conserved purine intermediate with multiple effects
Daignan-Fornier B and Pinson B
Metabolites, 2(2), 292-302 (2012)
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