cyclic AMP   Click here for help

GtoPdb Ligand ID: 2352

Abbreviated name: cAMP
Synonyms: 3' 5'-adenosine monophosphate | 3',5'-cyclic AMP | cyclic adenosine monophosphate
PDB Ligand
Compound class: Metabolite or derivative
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
OATP4C1
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
HCN1 Ligand is endogenous in the given species Mm Activator Agonist 7.2 pKd - 3,16
⤷ pKd 7.2 [3,16]
Voltage: -40.0 mV
CNGA3 Ligand is endogenous in the given species Rn Activator Agonist 3.6 pKd - 10
⤷ pKd 3.6 [10]
Voltage: -80.0 mV
CNGA3 Ligand is endogenous in the given species Hs Activator Agonist 2.9 pKd - 15,17
⤷ pKd 2.9 [15,17]
Voltage: -60.0 – 80.0 mV
HCN2 Ligand is endogenous in the given species Mm Activator Agonist 6.3 pKi - 12
⤷ pKi 6.3 [12]
Voltage: -40.0 mV
CNGA2 Ligand is endogenous in the given species Rn Activator Agonist 4.2 – 4.3 pEC50 - 1-2,11,14
⤷ pEC50 4.2 – 4.3 (EC50 6.16x10-5 – 4.57x10-5 M) [1-2,11,14]
Voltage: -80.0 – 100.0 mV
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Rank order of affinity at phosphodiesterase 8A cyclic AMP >> cyclic GMP 5
Activators at CNGA1 cyclic GMP (EC50 ~ 30 μM) >> cyclic AMP
Activators at CNGA3 cyclic GMP (EC50 ~ 30 μM) >> cyclic AMP
Activators at HCN1 cyclic AMP > cyclic GMP (both weak)
Activators at HCN2 cyclic AMP > cyclic GMP
Activators at HCN4 cyclic AMP > cyclic GMP
Activators at CNGA2 cyclic GMP > cyclic AMP (EC50 ~ 1 μM)
Rank order of affinity at phosphodiesterase 8B cyclic AMP >> cyclic GMP 9
Rank order of affinity at phosphodiesterase 1A cyclic GMP > cyclic AMP
Rank order of affinity at phosphodiesterase 1B cyclic GMP > cyclic AMP
Rank order of affinity at phosphodiesterase 1C cyclic GMP = cyclic AMP
Rank order of affinity at phosphodiesterase 2A cyclic AMP >> cyclic GMP
Rank order of affinity at phosphodiesterase 4A cyclic AMP >> cyclic GMP
Rank order of affinity at phosphodiesterase 4B cyclic AMP >> cyclic GMP
Rank order of affinity at phosphodiesterase 4C cyclic AMP >> cyclic GMP
Rank order of affinity at phosphodiesterase 4D cyclic AMP >> cyclic GMP
Rank order of affinity at phosphodiesterase 5A cyclic GMP > cyclic AMP
Rank order of affinity at phosphodiesterase 7A cyclic AMP >> cyclic GMP 13
Rank order of affinity at phosphodiesterase 7B cyclic AMP >> cyclic GMP 8
Rank order of affinity at phosphodiesterase 9A cyclic GMP >> cyclic AMP 6
Rank order of affinity at phosphodiesterase 10A cyclic AMP, cyclic GMP 7
Rank order of affinity at phosphodiesterase 11A cyclic AMP, cyclic GMP 4
Ligand mentioned in the following text fields
Adenylyl cyclases (ACs) overview
Cyclic nucleotide-regulated channels (CNG) overview
Exchange proteins activated by cyclic AMP (EPACs) overview
G protein-coupled estrogen receptor overview
Phosphodiesterases, 3',5'-cyclic nucleotide (PDEs) overview
Protein kinase A (PKA) family overview
Chloride channels comments
Phosphodiesterases, 3',5'-cyclic nucleotide (PDEs) comments