cyclic AMP   

GtoPdb Ligand ID: 2352

Abbreviated name: cAMP
Synonyms: 3' 5'-adenosine monophosphate | 3',5'-cyclic AMP | cyclic adenosine monophosphate
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 164.65
Molecular weight 329.05
XLogP -2.49
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC1C2OP(=O)(O)OCC2OC1n1cnc2c1ncnc2N
Isomeric SMILES O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1ncnc2N
InChI InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI Key IVOMOUWHDPKRLL-KQYNXXCUSA-N
Classification
Compound class Metabolite or derivative
IUPAC Name
(1S,6R,8R,9R)-8-(6-aminopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3$l^{5}-phosphabicyclo[4.3.0]nonan-9-ol
Synonyms
3' 5'-adenosine monophosphate | 3',5'-cyclic AMP | cyclic adenosine monophosphate
Database Links
CAS Registry No. 60-92-4
ChEBI CHEBI:17489
ChEMBL Ligand CHEMBL316966
DrugBank Ligand DB02527
GtoPdb PubChem SID 135651452
PubChem CID 6076
RCSB PDB Ligand CMP
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SynPHARM 5496 (in complex with HCN1)
5504 (in complex with HCN2)
Wikipedia Cyclic_adenosine_monophosphate