Adenosine monophosphate

Adenosine monophosphate
Skeletal formula of AMP
Ball-and-stick model of AMP
Names
IUPAC name
5′-Adenylic acid
Systematic IUPAC name
[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
Adenosine 5'-monophosphate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.455 Edit this at Wikidata
KEGG
MeSH Adenosine+monophosphate
UNII
  • InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1 checkY
    Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N checkY
  • InChI=1/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
    Key: UDMBCSSLTHHNCD-KQYNXXCUBP
  • O=P(O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O
  • c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
Properties
C10H14N5O7P
Molar mass 347.22 g/mol
Appearance white crystalline powder
Density 2.32 g/mL
Melting point 178 to 185 °C (352 to 365 °F; 451 to 458 K)
Boiling point 798.5 °C (1,469.3 °F; 1,071.7 K)
Acidity (pKa) 0.9[citation needed], 3.8, 6.1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide. AMP consists of a phosphate group, the sugar ribose, and the nucleobase adenine. It is an ester of phosphoric acid and the nucleoside adenosine.[1] As a substituent it takes the form of the prefix adenylyl-.[2]

AMP plays an important role in many cellular metabolic processes, being interconverted to adenosine triphosphate (ATP) and adenosine diphosphate (ADP), as well as allosterically activating enzymes such as myophosphorylase-b. AMP is also a component in the synthesis of RNA.[3] AMP is present in all known forms of life.[4]

  1. ^ "Adenosine monophosphate (Compound)". PubChem. NCBI. Retrieved 30 April 2020.
  2. ^ "Nomenclature of Carbohydrates: (Recommendations 1996)". Journal of Carbohydrate Chemistry. 16 (8): 1191–1280. 1997. doi:10.1080/07328309708005748.
  3. ^ Jauker M, Griesser H, Richert C (November 2015). "Spontaneous Formation of RNA Strands, Peptidyl RNA, and Cofactors". Angewandte Chemie. 54 (48): 14564–9. doi:10.1002/anie.201506593. PMC 4678511. PMID 26435376.
  4. ^ "Adenosine monophosphate". The Human Metabolome Database. Retrieved 3 July 2020.