Acadesine - Moligand™, ≥98% , AMP-activated protein kinase, AMPK activator, CAS No.2627-69-2, AMP-activated protein kinase, AMPK activator

CAS: 2627-69-2 Cat. No.: A129749 Molecular Weight: 258.23 EC Number: 220-097-5

GRADE & PURITY Moligand™, ≥98%

Synonyms

MLS004774120 | 5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide | 1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- | 53IEF47846 | 5-Amino-4-imidazolecarboxamide Riboside | ACADESINE [MI] | GP-1-110 | SCHEMBL219336 | SRI-4077_04 | Acadesi

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Acadesine results in accumulation of ZMP, which mimics the stimulating effect of AMP on AMPK and AMPK kinase.
An inhibitor of the transcription of PPARα, the coactivation of PPARα.

Specifications

Synonyms

MLS004774120 | 5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide | 1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- | 53IEF47846 | 5-Amino-4-imidazolecarboxamide Riboside | ACADESINE [MI] | GP-1-110 | SCHEMBL219336 | SRI-4077_04 | Acadesi

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

AICAR (AICA-Riboside) strongly inhibits the transcription of PPAR&alpha and the coactivation of PPAR&alpha. In adipocyte studies it has been shown to antagonize lipolysis induced by isoprenaline and has been suggested for use in kinase cascade research. A

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

ACTIVATOR

Mechanism of action

AMP-activated protein kinase, AMPK activator

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Product Properties

• ALogP: -2.2

Names and Identifiers

• Pubchem Sid: 488182399
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488182399
• Canonical Smiles: C1=NC(=C(N1C2C(C(C(O2)CO)O)O)N)C(=O)N
• IUPAC Name: 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
• InChIKey: RTRQQBHATOEIAF-UUOKFMHZSA-N
• INCHI: 1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1
• Isomeric SMILES: C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)C(=O)N
• WGK Germany: 3
• Molecular Weight: 258.23
• Reaxy-Rn: 623893
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=623893&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Imidazole ribonucleosides and ribonucleotides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Imidazole ribonucleosides and ribonucleotides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Imidazole ribonucleosides and ribonucleotides
• Alternative Parents: Glycosylamines Pentoses N-substituted imidazoles Aminoimidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Carboximidic acids Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Imidazole ribonucleoside - Glycosyl compound - N-glycosyl compound - Pentose monosaccharide - Aminoimidazole - Monosaccharide - N-substituted imidazole - Azole - Heteroaromatic compound - Imidazole - Tetrahydrofuran - Secondary alcohol - Carboximidic acid - Carboximidic acid derivative - Oxacycle - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Amine - Alcohol - Organic oxygen compound - Primary amine - Organonitrogen compound - Organooxygen compound - Primary alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as imidazole ribonucleosides and ribonucleotides. These are organic compounds in which the C-1 of a ribosyl moiety is N-linked to an imidazole ring. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety. This class does not contain benzimidazole nucleosides and nucleotides.
• External Descriptors: nucleoside analogue - aminoimidazole - 1-ribosylimidazolecarboxamide

Data sources

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

Associated Targets(Human)

CCRF-CEM (65223 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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MDA-MB-453 (1139 Activities)

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SK-BR-3 (5175 Activities)

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HCT-116 (91556 Activities)

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HEK293 (82097 Activities)

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HEL (6614 Activities)

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HeLa (62764 Activities)

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MDA-MB-231 (73002 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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GSK3A Tclin Glycogen synthase kinase-3 (736 Activities)

Discover Target: GSK3A

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

PRKAA2 Tchem AMP-activated protein kinase, AMPK (12273 Activities)

Discover Target: PRKAA2

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K-562R (114 Activities)

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Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Human alphaherpesvirus 2 (4932 Activities)

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Mus musculus (284745 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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3T3-L1 (3664 Activities)

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L1210 (27553 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Felid alphaherpesvirus 1 (460 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (9 mg/ml), and DMSO (75 mM).
• Sensitivity: Moisture sensitive
• Molecular Weight: 258.230 g/mol
• XLogP3: -2.200
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 258.096 Da
• Monoisotopic Mass: 258.096 Da
• Topological Polar Surface Area: 157.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 330.000
• 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

References

1. Yisen Cheng, Gaojian Chen, Li Wang, Jiamin Kong, Ji Pan, Yue Xi, Feihai Shen, Zhiying Huang.  (2018)  Triptolide-induced mitochondrial damage dysregulates fatty acid metabolism in mouse sertoli cells.  TOXICOLOGY LETTERS,      [PMID:29723566] [10.1016/j.toxlet.2018.04.035]

2. Chao Pan, Fajuan Wang, Yanzi Chu, Yahui Xue, Yan Ye, Kunlong Yang, Jinfeng Hua, Ling Shen, Jun Tian.  (2025)  Targeting the Snf1 kinase by cinnamaldehyde induces glucose starvation and oxidative stress in Fusarium solani for the control of sweet potato postharvest decay.  POSTHARVEST BIOLOGY AND TECHNOLOGY,      [PMID:] [10.1016/j.postharvbio.2025.114116]