AICA-Riboside, 5′-Phosphate is a monophosphorylated analog of the membrane permeable AICA-Riboside that mimics AMP and behaves as an AMPK (AMP-activated protein kinase) activator. AICA-Riboside, 5′-Phosphate displays similar effects of its parent derivative including stimulating glucose transport in certain skeletal-muscle cell lines.

5-aminoimidazole-4-formamide-1-β-d-ribofuran 5 '-monophosphate (AICAR) is a natural metabolic intermediate in purine biosynthesis, commonly found in all organisms. It is produced by succinyl-Aicar (SAICAR) with the help of adenylate succinase (ASL).

Application：

5-aminoimidazole-4-formamide-1-β-D-ribofuranyl 5 '-monophosphate was used in the study to explore the anticancer effects of nine statins in breast cancer and glioblastoma; AICAR monophosphate is a 5 "-phosphorylated analog of cellular permeable AICAR that mimics AMP. AICAR is an adenosine monophosphate (AMP) activated protein kinase (AMPK) activator/agonist.

Specifications

Synonyms

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

A 5'- phosphorylated analog of cell permeable AICAR that mimics adenosine monophosphate (AMP). It is an adenylate activated protein kinase (AMPK) activator. In humans, 5-aminoimidazole-4-formamide-1- β—— D-furosyl 5 '- monophosphate (AICAR) has been foun

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

Canonical Smiles	C1=NC(=C(N1C2C(C(C(O2)COP(=O)(O)O)O)O)N)C(=O)N
IUPAC Name	[(2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
InChIKey	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
Isomeric SMILES	C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N
WGK Germany	3
Molecular Weight	338.21
Reaxy-Rn	629374
Reaxys-RN_link_address	https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=629374&ln=

Documentation

📋 Safety Data Sheet (SDS)

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✅ Certificate of Analysis (COA)

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📊 Datasheet

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🔬 Specification Sheet

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Advanced Data

Taxonomic Classification

Taxonomy Tree

Kingdom Organic compounds
- Superclass Nucleosides, nucleotides, and analogues
  - Class Imidazole ribonucleosides and ribonucleotides
    - Subclass 1-ribosyl-imidazolecarboxamides

Kingdom	Organic compounds
Superclass	Nucleosides, nucleotides, and analogues
Class	Imidazole ribonucleosides and ribonucleotides
Subclass	1-ribosyl-imidazolecarboxamides
Intermediate Tree Nodes	Not available
Direct Parent	1-ribosyl-imidazolecarboxamides
Alternative Parents	Pentose phosphates Glycosylamines Monosaccharide phosphates 2-heteroaryl carboxamides Monoalkyl phosphates Carbonylimidazoles Aminoimidazoles N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Vinylogous amides Primary carboxylic acid amides Secondary alcohols Amino acids and derivatives 1,2-diols Oxacyclic compounds Azacyclic compounds Organic oxides Organopnictogen compounds Primary amines Hydrocarbon derivatives
Molecular Framework	Aromatic heteromonocyclic compounds
Substituents	1-ribosyl-imidazolecarboxamide - Pentose phosphate - Pentose-5-phosphate - Glycosyl compound - N-glycosyl compound - Monosaccharide phosphate - Pentose monosaccharide - 2-heteroaryl carboxamide - Imidazole-4-carbonyl group - Monoalkyl phosphate - Aminoimidazole - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Alkyl phosphate - Phosphoric acid ester - Azole - Imidazole - Heteroaromatic compound - Vinylogous amide - Tetrahydrofuran - Primary carboxylic acid amide - Secondary alcohol - Amino acid or derivatives - 1,2-diol - Carboxamide group - Organoheterocyclic compound - Azacycle - Oxacycle - Carboxylic acid derivative - Primary amine - Organonitrogen compound - Organopnictogen compound - Organooxygen compound - Organic oxygen compound - Amine - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Alcohol - Aromatic heteromonocyclic compound
Description	This compound belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
External Descriptors	1-(phosphoribosyl)imidazolecarboxamide - aminoimidazole
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61. DOI: 10.1186/s13321-016-0174-y

3D Structure

Associated Targets(Human)

CASP3 Tchem Caspase-3 (3632 Activities)

Discover Target: CASP3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ATIC Tchem AICAR transformylase (241 Activities)

Discover Target: ATIC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

FBP1 Tchem Fructose-1,6-bisphosphatase (1199 Activities)

Discover Target: FBP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CASP9 Tchem Caspase-9 (154 Activities)

Discover Target: CASP9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

5637 (630 Activities)

Lot Number	Certificate Type	Date	Item
B2423657	Certificate of Analysis	Jan 16, 2024	A346730
B2423659	Certificate of Analysis	Jan 16, 2024	A346730
B2423666	Certificate of Analysis	Jan 16, 2024	A346730
B2423668	Certificate of Analysis	Jan 16, 2024	A346730
B2423671	Certificate of Analysis	Jan 16, 2024	A346730
J2523230	Certificate of Analysis	Jan 16, 2024	A346730

Solubility	Soluble in water (partly miscible), DMSO, and methanol.
Sensitivity	Moisture sensitive
Refractive Index	n20D1.83 (Predicted)
Boil Point(°C)	~845.3° C at 760 mmHg (Predicted)
Melt Point(°C)	>160° C (dec.)
Molecular Weight	338.210 g/mol
XLogP3	-3.800
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Exact Mass	338.063 Da
Monoisotopic Mass	338.063 Da
Topological Polar Surface Area	203.000 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	475.000
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
The total count of all stereochemical bonds	0
Covalently-Bonded Unit Count	1

AICA-Riboside, 5′-Phosphate - ≥95% , CAS No.3031-94-5

Why this grade

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Literature proof

Overview

Specifications

Documentation

📋 Safety Data Sheet (SDS)

✅ Certificate of Analysis (COA)

📊 Datasheet

🔬 Specification Sheet

Advanced Data

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