Details of Metabolite

General Information of MET (ID: META00014)
Name AICAR
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide, 5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide, 5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide, '5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide; 4-Carboxy-5-aminoimidazole ribotide; 5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphate', 5-Amino-4-imidazolecarboxamide ribofuranoside 5'-monophosphate, 'AICA Ribonucleotide, (D-ribofuranosyl)-isomer', AICAriboside 5'-monophosphate, 'CAIR; 5-Aminoimidazole-4-carboxamide ribotide; 5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole', Acadesine 5'-monophosphate, 'AICA-Ribonucleotide; AICA Ribonucleotide; Aminoimidazole carboxamide ribonucleotide; Z-Nucleotide; ZMP
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Microbial
Structure Type   1-ribosyl-imidazolecarboxamides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Imidazole ribonucleosides and ribonucleotides
1-ribosyl-imidazolecarboxamides
PubChem CID
65110
HMDB ID
HMDB0001517
Formula
C9H15N4O8P
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C04677
DrugBank ID
DB01700
ChEBI ID
18406
FooDB ID
FDB001213
ChemSpider ID
58620
METLIN ID
6294
Physicochemical Properties Molecular Weight 338.21 Topological Polar Surface Area 203
XlogP -3.8 Complexity 475
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 10
Function
AICAR also known as ZMP is an analog of AMP that is capable of stimulating AMP-dependent protein kinase activity(AMPK). AICAR is an intermediate in the generation of inosine monophosphate. AICAR is being clinically used to treat and protect against cardiac ischemic injury. AICAR can enter cardiac cells to inhibit adenosine kinase and adenosine deaminase. It enhances the rate of nucleotide re-synthesis increasing adenosine generation from adenosine monophosphate only during conditions of myocardial ischemia. AICAR increases glucose uptake by inducing translocation of GLUT4 and/or by activating the p38 MAPK pathway.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      Cytokine receptor (CytR)
            Apoptosis mediating surface antigen FAS (CD95) 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 AICAR addition (24 hours)
                      Induced Change FAS mRNA levels: increase (FC = 0.62)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that AICAR addition causes the increase of FAS mRNA levels compared with control group.
      Hydrolases (EC 3)
            Glucose-6-phosphatase catalytic 1 (G6PC1) 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 AICAR addition (24 hours)
                      Induced Change G6PC1 mRNA levels: increase (FC = 4.35)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that AICAR addition causes the increase of G6PC1 mRNA levels compared with control group.
      Ligases (EC 6)
            Acetyl-CoA carboxylase 1 (ACACA) 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 AICAR addition (1 hours)
                      Induced Change ACACA protein phosphorylation levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Insulin-resistance syndromes [ICD-11: 5A44]
                      Details It is reported that AICAR addition causes the increase of ACACA protein phosphorylation compared with control group.
      Lyases (EC 4)
            Phosphoenolpyruvate carboxykinase 1 (PCK1) 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 AICAR addition (24 hours)
                      Induced Change PCK1 mRNA levels: decrease (FC = 0.19)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that AICAR addition causes the decrease of PCK1 mRNA levels compared with control group.
            Phosphoenolpyruvate carboxykinase 2 (PCK2) 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 AICAR addition (24 hours)
                      Induced Change PCK2 mRNA levels: decrease (FC = 0.19)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that AICAR addition causes the decrease of PCK2 mRNA levels compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) 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 [2]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change AICAR concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of AICAR levels compared with control group.
      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 [3]
                      Introduced Variation Knockout of TP53
                      Induced Change AICAR concentration: decrease (Log2 FC=0.27)
                      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 AICAR levels compared with control group.
References
1 Identification and characterization of a small molecule AMPK activator that treats key components of type 2 diabetes and the metabolic syndrome. Cell Metab. 2006 Jun;3(6):403-16.
2 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
3 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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