cyclic GMP   Click here for help

GtoPdb Ligand ID: 2347

Abbreviated name: cGMP
Synonyms: 3',5'-cyclic GMP | 3',5'-guanosine monophosphate | cyclic guanosine 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 4
Rotatable bonds 1
Topological polar surface area 184.62
Molecular weight 345.05
XLogP -2.44
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)OCC2OC1n1cnc2c1nc(N)[nH]c2=O
Isomeric SMILES O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O
InChI InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
InChI Key ZOOGRGPOEVQQDX-UUOKFMHZSA-N
Natural/Endogenous Targets
Target
phosphodiesterase 2A
phosphodiesterase 3A
phosphodiesterase 3B
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CNGA3 Ligand is endogenous in the given species Rn Activator Agonist 5.5 pKd - 13
⤷ pKd 5.5 [13]
Voltage: -80.0 – 80.0 mV
CNGA3 Ligand is endogenous in the given species Hs Activator Agonist 4.7 – 5.6 pKd - 19-21
⤷ pKd 4.7 – 5.6 [19-21]
Voltage: -60.0 – 80.0 mV
HCN2 Ligand is endogenous in the given species Mm Activator Agonist 5.2 pKi - 15
⤷ pKi 5.2 [15]
Voltage: -40.0 mV
CNGA1 Ligand is endogenous in the given species Hs Activator Agonist 4.1 – 4.2 pKi - 2-4,6,11,18,22
⤷ pKi 4.1 – 4.2 (Ki 8.5x10-5 – 6x10-5 M) [2-4,6,11,18,22]
Voltage: -60.0 – 60.0 mV
CNGA2 Ligand is endogenous in the given species Rn Activator Agonist 5.6 – 5.8 pEC50 - 1,14,17
⤷ pEC50 5.6 – 5.8 (EC50 2.5x10-6 – 1.74x10-6 M) [1,14,17]
Voltage: -80.0 – 100.0 mV
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphodiesterase 2A Ligand is endogenous in the given species Hs Activator Activation - - -
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phosphodiesterase 3A Ligand is endogenous in the given species Hs Inhibitor Inhibition - - -
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phosphodiesterase 3B Ligand is endogenous in the given species Hs Inhibitor Inhibition - - -
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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 7
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 12
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 16
Rank order of affinity at phosphodiesterase 7B cyclic AMP >> cyclic GMP 10
Rank order of affinity at phosphodiesterase 9A cyclic GMP >> cyclic AMP 8
Rank order of affinity at phosphodiesterase 10A cyclic AMP, cyclic GMP 9
Rank order of affinity at phosphodiesterase 11A cyclic AMP, cyclic GMP 5
Other ligands which bind to or alter the activity of this ligand
Key to terms and symbols Click column headers to sort
Ligand Sp. Type Action Value Parameter Concentration range (M) Reference
Rp-8-Br-cGMPS Small molecule or natural product N/A Inhibitor Inhibition - - -
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Ligand mentioned in the following text fields
Cyclic nucleotide-regulated channels (CNG) overview
Phosphodiesterases, 3',5'-cyclic nucleotide (PDEs) overview
Protein kinase G (PKG) family overview
Receptor guanylyl cyclase (RGC) family overview
CFTR comments
Chloride channels comments
Phosphodiesterases, 3',5'-cyclic nucleotide (PDEs) comments