adenosine cyclic phosphate

Also 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.

In the Vinony graph

Vinony's link graph records 779 inbound references to adenosine cyclic phosphate, and connects out to protein kinase A, enzyme and adenylate cyclase.

Vinony files it under Cyclic nucleotides, ECHA InfoCard ID from Wikidata and Nucleotides.

Vinony links it to 42 Wikipedia language editions.

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 Å²
H-bond donors: 3
H-bond acceptors: 10
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

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

Wikidata facts

Has part: carbon
Mass: 329.053

Show 5 more facts

found in taxon: Caenorhabditis elegans
chemical formula: C₁₀H₁₂N₅O₆P
canonical SMILES: C1C2C(C(C(O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O
isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CN=C4N)O)OP(=O)(O1)O
Commons category: Cyclic adenosine monophosphate

Sources (4)

via Wikidata · CC0

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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.