Adenosine monophosphate

Adenosine monophosphate
Adenosine monophosphate
CAS number 61-19-8 YesY
ChemSpider 5858 YesY
UNII 415SHH325A YesY
DrugBank DB00131
KEGG C00020 YesY
MeSH Adenosine+monophosphate
ChEBI CHEBI:16027 YesY
IUPHAR ligand 2455
Jmol-3D images Image 1
Image 2
Molecular formula C10H14N5O7P
Molar mass 347.22 g/mol
Acidity (pKa) 0.9, 3.8, 6.1
 YesY monophosphate (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid and the nucleoside adenosine. AMP consists of a phosphate group, the sugar ribose, and the nucleobase adenine. As a substituent it takes the form of the prefix adenylyl-.


Production and degradation

AMP can be produced during ATP synthesis by the enzyme adenylate kinase by combining two ADP molecules:


Or AMP may be produced by the hydrolysis of one high energy phosphate bond of ADP:

ADP → AMP + Pi

AMP can also be formed by hydrolysis of ATP into AMP and pyrophosphate:


When RNA is broken down by living systems, nucleoside monophosphates, including adenosine monophosphate, are formed.

AMP can be regenerated to ATP as follows:

AMP + ATP → 2 ADP (adenylate kinase in the opposite direction)
ADP + Pi → ATP (this step is most often performed in aerobes by the ATP synthase during oxidative phosphorylation)

AMP can be converted into IMP by the enzyme myoadenylate deaminase, freeing an ammonia group.

In a catabolic pathway, adenosine monophosphate can be converted to uric acid, which is excreted from the body.


AMP can also exist as a cyclic structure known as cyclic AMP (or cAMP). Within certain cells the enzyme adenylate cyclase makes cAMP from ATP, and typically this reaction is regulated by hormones such as adrenaline or glucagon. cAMP plays an important role in intracellular signaling.

See also


External links

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