<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-26 05:32:33 UTC</creation_date>
  <update_date>2026-08-17 23:40:51 UTC</update_date>
  <accession/>
  <common_name>Cyclic GMP</common_name>
  <class>SmallMolecule</class>
  <description>Cyclic GMP is an organic compound with the formula C10H12N5O7P and an average molecular weight of 345.21 g/mol. Cyclic GMP belongs to the cyclic purine nucleotides, a subclass of purine nucleotides within the organic compounds. It is classified under the superclass of nucleosides, nucleotides, and analogues.

This compound has been recorded as being found in or released from electrical and electronic equipment antennas. In biological systems, it interacts with three recorded protein targets: the cAMP-dependent protein kinase type I-alpha regulatory subunit (PRKAR1A), the potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 (HCN2), and it acts as an inhibitor of cGMP-dependent 3',5'-cyclic phosphodiesterase (PDE2A).</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>cyclic-GMP</synonym>
  </synonyms>
  <chemical_formula>C10H12N5O7P</chemical_formula>
  <average_molecular_weight>345.2053</average_molecular_weight>
  <monisotopic_moleculate_weight>345.047434275</monisotopic_moleculate_weight>
  <iupac_name>9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one</iupac_name>
  <traditional_iupac>cyclic-GMP</traditional_iupac>
  <cas_registry_number>7665-99-8</cas_registry_number>
  <smiles>NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1</smiles>
  <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>
  <inchikey>ZOOGRGPOEVQQDX-UUOKFMHZSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleotides</class>
    <sub_class>Cyclic purine nucleotides</sub_class>
    <direct_parent>3',5'-cyclic purine nucleotides</direct_parent>
    <alternate_parents>
      <alternative_parent>6-oxopurines</alternative_parent>
      <alternative_parent>Aminopyrimidines and derivatives</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Glycosylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hypoxanthines</alternative_parent>
      <alternative_parent>Monosaccharide phosphates</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic phosphoric acids and derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentose phosphates</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>3',5'-cyclic purine ribonucleotide</substituent>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminopyrimidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azole</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hypoxanthine</substituent>
      <substituent>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide phosphate</substituent>
      <substituent>N-glycosyl compound</substituent>
      <substituent>N-substituted imidazole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic phosphoric acid derivative</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose phosphate</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Purine</substituent>
      <substituent>Purinone</substituent>
      <substituent>Pyrimidine</substituent>
      <substituent>Pyrimidone</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
      <substituent>Vinylogous amide</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>3',5'-Cyclic nuclcleotides</descriptor>
      <descriptor>3',5'-cyclic purine nucleotide</descriptor>
      <descriptor>guanyl ribonucleotide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.96</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.79e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>2.05</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>345.2053</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>345.047434275</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H12N5O7P</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>ZOOGRGPOEVQQDX-UUOKFMHZSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>170.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>71.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
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  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7227e48900&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB02315</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>135398570</pubchem_compound_id>
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