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Merck
모든 사진(2)

주요 문서

A1393

Sigma-Aldrich

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

≥93%

동의어(들):

AICAR monophosphate, N1-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide, NSC 283955, NSC 292227, ZMP

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About This Item

실험식(Hill 표기법):
C9H15N4O8P
CAS Number:
Molecular Weight:
338.21
EC Number:
MDL number:
UNSPSC 코드:
41106305
PubChem Substance ID:
NACRES:
NA.51

Quality Level

분석

≥93%

양식

powder

분자량

338.21  g/mol

저장 온도

−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

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일반 설명

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.

애플리케이션

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.

생화학적/생리학적 작용

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


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문서 라이브러리 방문

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
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
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
Licht Miyamoto et al.
American journal of physiology. Cell physiology, 305(12), C1214-C1222 (2013-10-04)
Physical exercise has potent therapeutic and preventive effects against metabolic disorders. A number of studies have suggested that 5'-AMP-activated protein kinase (AMPK) plays a pivotal role in regulating carbohydrate and lipid metabolism in contracting skeletal muscles, while several genetically manipulated
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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