Editing Adenosine monophosphate (section)

{{use dmy dates|date=April 2020}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477242440
| ImageFile = Adenosinmonophosphat protoniert.svg
| ImageSize = 200px
| ImageName = Skeletal formula of AMP
| ImageFile1 = Adenosine-monophosphate-anion-3D-balls.png
| ImageSize1 = 200px
| ImageName1 = Ball-and-stick model of AMP
| IUPACName = 5′-Adenylic acid
| SystematicName = [(2''R'',3''S'',4''R'',5''R'')-5-(6-Amino-9''H''-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
| OtherNames = Adenosine 5'-monophosphate<br/>Vitamin B8 <ref>{{cite web |title=Depositor-Supplied Synonyms |url=https://pubchem.ncbi.nlm.nih.gov/compound/6083#section=Depositor-Supplied-Synonyms |website=PubChem |publisher=NCBI}}</ref>
|Section1={{Chembox Identifiers
| PubChem = 6083
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5858
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 415SHH325A
| 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
| InChIKey = UDMBCSSLTHHNCD-KQYNXXCUBP
| SMILES1 = c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 752
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UDMBCSSLTHHNCD-KQYNXXCUSA-N
| CASNo = 61-19-8
| CASNo_Ref = {{cascite|correct|CAS}}
| IUPHAR_ligand = 2455
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00131
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16027
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00020
| SMILES = O=P(O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3O
| MeSHName = Adenosine+monophosphate
  }}
|Section2={{Chembox Properties
| C=10 | H=14 | N=5 | O=7 | P=1
| MolarMass = 347.22 g/mol
| Appearance = white crystalline powder
| pKa = 0.9{{citation needed|date=September 2016}}, 3.8, 6.1
| Density = 2.32 g/mL
| MeltingPtC = 178 to 185 
| BoilingPtC = 798.5
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
  }}
}}
'''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]].<ref>{{cite web |title=Adenosine monophosphate (Compound) |url=https://pubchem.ncbi.nlm.nih.gov/compound/Adenosine-monophosphate |website=PubChem |publisher=NCBI |access-date=30 April 2020}}</ref> As a [[substituent]] it takes the form of the prefix '''adenylyl-'''.<ref>{{cite journal |title=Nomenclature of Carbohydrates: (Recommendations 1996) |journal=Journal of Carbohydrate Chemistry |date=1997 |volume=16 |issue=8 |pages=1191–1280 |doi=10.1080/07328309708005748}}</ref>

AMP plays an important role in many cellular metabolic processes, being interconverted to [[adenosine triphosphate]] (ATP) and [[adenosine diphosphate]] (ADP), as well as [[Allosteric regulation|allosterically]] activating enzymes such as myophosphorylase-b. AMP is also a component in the synthesis of [[RNA]].<ref>{{cite journal | vauthors = Jauker M, Griesser H, Richert C | title = Spontaneous Formation of RNA Strands, Peptidyl RNA, and Cofactors | journal = Angewandte Chemie | volume = 54 | issue = 48 | pages = 14564–9 | date = November 2015 | pmid = 26435376 | pmc = 4678511 | doi = 10.1002/anie.201506593 }}</ref> AMP is present in all known forms of life.<ref>{{cite web |title=Adenosine monophosphate |url=https://hmdb.ca/metabolites/HMDB0000045 |website=The Human Metabolome Database |access-date=3 July 2020}}</ref>