File:ATP_structure_revised.svg · Wikimedia Commons · See Wikimedia Commons
adenosine cyclic phosphate
Sign in to saveAlso known as 3' 5'-adenosine monophosphate, 3',5'-cyclic AMP, cAMP, cyclic adenosine monophosphate, adenosine 3',5'-cyclic monophosphate, Adenosine 3',5'-cyclic phosphate, (1R,6R,7R,8R)-8-(6-aminopurin-9-yl)-4-hydroxy-4-oxo-3,5,9-trioxa-4$l^{5}-phosphabicyclo[4.3.0]nonan-7-ol, Cyclic adenosine 3',5'-phosphate
chemical compound
OverviewAI-generated
Adenosine cyclic phosphate is a chemical compound with the formula C₁₀H₁₂N₅O₆P. Its IUPAC name is (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol. The substance has a mass of 329.053 and a weight of 329.21. It carries a charge of 0 and features an xlogp value of -2.6.
The molecule contains three hydrogen bond donors and ten hydrogen bond acceptors, with a topological polar surface area of 155. Its canonical SMILES notation is C1C2C(C(C(O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O. A related isomeric SMILES string is C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O. The compound is associated with the category "Cyclic adenosine monophosphate" and is referenced by 779 other encyclopedia articles.
Synthesized by Vinony from 18 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
- C10H12N5O6P
- Molecular weight
- 329.21 g/mol
- IUPAC name
- (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
- SMILES
- C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)O
- InChIKey
- IVOMOUWHDPKRLL-KQYNXXCUSA-N
- XLogP
- -2.6
- Polar surface area
- 155 Ų
- H-bond donors
- 3
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Research
121,829 papers- The mode of action of adenosine 3':5'-cyclic phosphate in the regulation of insulin secretion.Ciba Foundation symposium · 1976
- Cyclic GMP-AMP containing mixed phosphodiester linkages is an endogenous high-affinity ligand for STING.Molecular cell · 2013
- Mode of action of parathyroid hormone and cyclic adenosine 3',5'-monophosphate on renal tubular phosphate reabsorption in the dog.The Journal of clinical investigation · 1971
- Adenosine 3',5'-phosphate in fungi.Microbiological reviews · 1981
- Radioimmunoassay for the measurement of adenosine 3',5'-cyclic phosphate.Proceedings of the National Academy of Sciences of the United States of America · 1969
via PubMed
~9 min read
Encyclopedic overview
cAMP represented in three ways Adenosine triphosphate Cyclic adenosine monophosphate (cAMP, cyclic AMP, or 3',5'-cyclic adenosine monophosphate) is a second messenger, or cellular signal occurring within cells, that is important in many biological processes. cAMP is a derivative of adenosine triphosphate (ATP) and used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway.
History
Excerpted from Wikipedia’s “adenosine cyclic phosphate” article, available under the CC BY-SA 4.0 licence.