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
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2D Structure
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Physico-chemical Properties
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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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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
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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
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphodiesterase 2A Ligand is endogenous in the given species Hs Activator Activation - - -
phosphodiesterase 3A Ligand is endogenous in the given species Hs Inhibitor Inhibition - - -
phosphodiesterase 3B Ligand is endogenous in the given species Hs Inhibitor Inhibition - - -
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Other ligands which bind to or alter the activity of this ligand
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Ligand Sp. Type Action Value Parameter Concentration range (M) Reference
Rp-8-Br-cGMPS Small molecule or natural product N/A Inhibitor Inhibition - - -
Ligand mentioned in the following text fields