Details of Metabolite

General Information of MET (ID: META00938)
Name AICA-riboside
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-Ribosyl-4-carboxamido-5-aminoimidazole; 1-beta-D-Ribofuranosyl-5-amino-4-imidazolecarboxamide; 5-Amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide; 5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide; 5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamide; 5-Amino-1-ribofuranosylimidazole-4-carboxamide; 5-Amino-1-ribosyl-4-imidazolecarboxamide; 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxyamide; 5-Amino-4-imidazolecarboxamide ribofuranoside; 5-Aminoimidazole-4-carboxamide 1-(beta-D-ribofuranoside); 5-Aminoimidazole-4-carboxamide 1-ribofuranoside; 5-Aminoimidazole-4-carboxamide ribonucleoside; 5-Aminoimidazole-4-carboxamide riboside; 5-Aminoimidazole-4-carboxamide-N-ribofuranoside; AIC-riboside; AICA Ribofuranoside; AICA Ribonucleoside; AICA Riboside; AICA-riboside; AICAr; ARA-100; Acadesina; Acadesine; Acadesinum; Acadra; Aminoimidazole carboxamide ribonucleoside; Arasine; EC number 220-097-5; GP 1-110; GP-1-110; N(1)-(beta-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide; NSC 105823; Z-Riboside
Source Drug
Structure Type   Imidazole ribonucleosides and ribonucleotides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Imidazole ribonucleosides and ribonucleotides
PubChem CID
17513
HMDB ID
HMDB0062179
Formula
C9H14N4O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
DrugBank ID
DB04944
ChEBI ID
28498
Physicochemical Properties Molecular Weight 258.23 Topological Polar Surface Area 157
XlogP -2.2 Complexity 330
Heavy Atom Count 18 Rotatable Bond Count 3
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 7
Function
AICA-riboside, also known as acadesine or AICAR, is an AMP-activated protein kinase activator which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes. AICA-riboside is an adenosine regulating agent developed by PeriCor Therapeutics and licensed to Schering-Plough in 2007 for phase III studies. The drug is a potential first-in-class agent for prevention of reperfusion injury in CABG surgery. Schering began patient enrollment in phase III studies in May, 2009. The trial was terminated in late 2010 based on an interim futility analysis. AICA-riboside is a minor constituent found in human milk.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of TP53
                      Induced Change AICA-riboside concentration: decrease (Log2 FC=0.19)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of AICA-riboside levels compared with control group.
References
1 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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