File:Adenosinmonophosphat_protoniert.svg · Wikimedia Commons · See Wikimedia Commons
adenosine monophosphate
Sign in to saveAlso known as 5'-AMP, AMP, 5'-O-phosphonoadenosine, adenosine 5'-(dihydrogen phosphate), adenosine-5'P, Ado5'P, PAdo, Adenosine-5'-monophosphoric acid
chemical compound
OverviewAI-generated
Adenosine monophosphate is a chemical compound with the formula C₁₀H₁₄N₅O₇P. It has a mass of 347.063 and a weight of 347.22. The substance decomposes at 195 and has a pKa of 6.2. Its canonical SMILES notation is C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)COP(=O)(O)O)O)O, while its isomeric SMILES is C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O.
Chemical properties include an xlogp of -3.5, a tpsa of 186, and a charge of 0. The molecule contains 5 hydrogen bond donors and 11 hydrogen bond acceptors. Adenosine monophosphate is associated with 46846 PubMed entries and is referenced by 672 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C10H14N5O7P
- Molecular weight
- 347.22 g/mol
- IUPAC name
- [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- SMILES
- C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
- InChIKey
- UDMBCSSLTHHNCD-KQYNXXCUSA-N
- XLogP
- -3.5
- Polar surface area
- 186 Ų
- H-bond donors
- 5
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- ischemia
via ChEMBL · EBI
Research
46,846 papers- Role of adenosine monophosphate-activated protein kinase in the control of energy homeostasis.Current opinion in clinical nutrition and metabolic care · 2005
- Roles of adenosine monophosphate-activated protein kinase (AMPK) in the kidney.Chinese medical journal · 2022
- Effect of tyramine on the production of interstitial adenosine during perfusion with adenosine 5'-monophosphate in rat hearts in vivo.European journal of pharmacology · 2013
- Adenosine monophosphate for the treatment of varicella zoster infections: a large dose of caution.JAMA · 1985
- Cyclic Adenosine Monophosphate: A Central Player in Gamete Development and Fertilization, and Possible Target for Infertility Therapies.International journal of molecular sciences · 2022
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 347.063
- Has use
- medication
Show 9 more facts
- chemical formula
- C₁₀H₁₄N₅O₇P
- canonical SMILES
- C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)COP(=O)(O)O)O)O
- isomeric SMILES
- C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O
- World Health Organisation international non-proprietary name
- adenosine phosphate
- Commons category
- Adenosine monophosphate
- decomposition point
- 195
- pKa
- 6.2
- found in taxon
- Escherichia coli
- subject has role
- primary metabolite
Sources (6)
via Wikidata · CC0
~5 min read
Encyclopedic overview
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. As a substituent it takes the form of the prefix adenylyl-.
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. AMP is present in all known forms of life.
Excerpted from Wikipedia’s “adenosine monophosphate” article, available under the CC BY-SA 4.0 licence.