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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

Key Documents

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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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Show Differences

1 of 4

This Item
A1393A9501U6375
5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate analytical standard

Supelco

06595

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

5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate ≥93%

Sigma-Aldrich

A1393

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

Adenosine 3′,5′-cyclic monophosphate ≥98.5% (HPLC), powder

Sigma-Aldrich

A9501

Adenosine 3′,5′-cyclic monophosphate

Uridine 5′-monophosphate disodium salt ≥99%

Sigma-Aldrich

U6375

Uridine 5′-monophosphate disodium salt

application(s)

forensics and toxicology
pharmaceutical (small molecule)

application(s)

-

application(s)

-

application(s)

-

grade

analytical standard

grade

-

grade

-

grade

-

format

neat

format

-

format

-

format

-

assay

≥98.0% (HPLC)

assay

≥93%

assay

≥98.5% (HPLC)

assay

≥99%

optical activity

[α]/D -69.0±3.0°, c = 0.1 in sodium bicarbonate

optical activity

-

optical activity

-

optical activity

-

shelf life

limited shelf life, expiry date on the label

shelf life

-

shelf life

-

shelf life

-

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.[1]

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
Takashi Sasaki et al.
American journal of physiology. Endocrinology and metabolism, 306(9), E1085-E1092 (2014-03-20)
Exercise can effectively ameliorate type 2 diabetes and insulin resistance. Here we show that the mRNA levels of one of peroxisome proliferator-activated receptor (PPAR) family members, PPARγ1, and genes related to energy metabolism, including PPARγ coactivator-1 protein-1α (PGC-1α) and lipoprotein
Lykke Sylow et al.
Diabetes, 62(4), 1139-1151 (2013-01-01)
In skeletal muscle, the actin cytoskeleton-regulating GTPase, Rac1, is necessary for insulin-dependent GLUT4 translocation. Muscle contraction increases glucose transport and represents an alternative signaling pathway to insulin. Whether Rac1 is activated by muscle contraction and regulates contraction-induced glucose uptake is
Joshua D Stone et al.
American journal of physiology. Heart and circulatory physiology, 304(3), H369-H381 (2012-12-04)
Vascular smooth muscle cell (VSMC) activation promotes a synthetic phenotype that underlies many vessel growth disorders. In this regard it has been suggested that the metabolic sensor adenosine 5'-monophosphate-activated protein kinase (AMPK) has significant antigrowth and antimetastatic properties and may
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