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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
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grade

analytical standard

Quality Segment

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

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.

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Storage Class

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

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