Details of Metabolite

General Information of MET (ID: META00142)
Name Cyclic AMP
Synonyms   Click to Show/Hide Synonyms of This Metabolite
AMP, Cyclic', Adenosine cyclic 3',5' monophosphate, Adenosine cyclic-3',5'-monophosphate, 'Cyclic AMP, (R)-isomer; Acrasin', Adenosine 3',5'-cyclophosphate, Adenosine 3',5'-monophosphate, Adenosine 3,5'-cyclic monophosphorate, Adenosine 3,5'-cyclic monophosphoric acid, 'Adenosine cyclic monophosphate; Adenosine 3',5'-cyclic monophosphate, Adenosine 3',5'-cyclic phosphate, Adenosine 3',5'-phosphate, ADENOSINE-3',5'-cyclic-monophosphATE, 'CAMP; Adenosine cyclic 3,5 monophosphate', Cyclic 3',5'-monophosphate, adenosine, 'Cyclic AMP, monoammonium salt; Adenosine cyclic-monophosphate; Adenosine-cyclic-phosphate; Adenosine-cyclic-phosphoric-acid', Cyclic 3',5'-adenylate, Cyclic 3',5'-adenylic acid, Cyclic 3',5'-AMP, Cyclic adenosine 3',5'-phosphate, 3',5'-monoPhosphate, adenosine cyclic, 'Cyclic AMP, disodium salt; Cyclic AMP, monopotassium salt; Cyclic AMP, monosodium salt', Adenosine cyclic 3',5'-monophosphate, 'monoPhosphate, adenosine cyclic; Cyclic AMP, sodium salt; Cyclic adenylic acid', Adenosine 3',5'-cyclic monophosphoric acid, Adenosine 3',5'-cyclic phosphoric acid, Adenosine 3',5'-phosphoric acid, ADENOSINE-3',5'-cyclic-monophosphoric acid, 'Cyclic adenylate', 3'5'-Cyclic AMP, '6-(6-Amino-9H-purin-9-yl)tetrahydro-4H-furo[3,2-D][1,3,2]dioxaphosphinine-2,7-diol 2-oxide; Cyclic monophosphate, adenosine', Cyclic-3',5'-monophosphate, adenosine, 'Cyclic AMP
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Microbial
Structure Type   Cyclic purine nucleotides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Purine nucleotides
Cyclic purine nucleotides
PubChem CID
6076
HMDB ID
HMDB0000058
Formula
C10H12N5O6P
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
C00575
DrugBank ID
DB02527
ChEBI ID
17489
FooDB ID
FDB001497
ChemSpider ID
5851
METLIN ID
5120
Physicochemical Properties Molecular Weight 329.21 Topological Polar Surface Area 155
XlogP -2.6 Complexity 498
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 10
Function
Cyclic AMP is an adenine nucleotide containing one phosphate group which is esterified to both the 3'- and 5'-positions of the sugar moiety. It is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon, and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR secretin (GPCR-2)
            Glucagon receptor (GCGR) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Antagonist (GRA1) of GCGR
                      Induced Change Cyclic AMP concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Hyperglycemic hyperosmolar syndrome [ICD-11: 5A20]
                      Details It is reported that antagonist of GCGR leads to the decrease of cyclic AMP levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Antagonist (GRA1) of Gcgr
                      Induced Change Cyclic AMP concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Hyperglycemic hyperosmolar syndrome [ICD-11: 5A20]
                      Details It is reported that antagonist of GCGR leads to the decrease of cyclic AMP 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 [2]
                      Introduced Variation Knockout of TP53
                      Induced Change Cyclic AMP concentration: increase (Log2 FC=2.45)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of cyclic AMP levels compared with control group.
      Transferases (EC 2)
            Transaldolase (TALDO1) 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 Taldo1
                      Induced Change Cyclic AMP concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Taldo1 leads to the decrease of cyclic AMP levels compared with control group.
References
1 Anti-diabetic efficacy and impact on amino acid metabolism of GRA1, a novel small-molecule glucagon receptor antagonist. PLoS One. 2012;7(11):e49572.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
3 Two isoforms of TALDO1 generated by alternative translational initiation show differential nucleocytoplasmic distribution to regulate the global metabolic network. Sci Rep. 2016 Oct 5;6:34648.

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