<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:06:40 UTC</creation_date>
  <update_date>2025-11-18 22:59:10 UTC</update_date>
  <accession>FDB005416</accession>
  <name>Guanidine</name>
  <description>Guanidine apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes.; Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. It is found in urine as a normal product of protein metabolism. The molecule was first synthesized in 1861 by the oxidative degradation of an aromatic natural product, guanine, isolated from Peruvian guano. Despite the provocative simplicity of the molecule, the crystal structure was first described 148 years later.; Guanidine is a polyamine that can function as a strong organic base existing primarily as guanidium ions at physiological pH.  With a pKa of 12.5, guanidine is protonated, with a charge of +1 in physiological conditions.  It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed).  Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives.   -- Wikipedia; Guanidines are a group of organic compounds sharing a common functional group with the general structure (R1R2N)(R3R4N)C=N-R5. The central bond within this group is that of an imine; the other recognizable motif within this group is an aminal. Examples of guanidines are arginine, triazabicyclodecene and saxitoxin. other derivatives could include guanidine hydroxide, the active ingredient in some non-lye relaxers. Guanidinium salts are well known for their denaturing action on proteins. Guanidinium chloride is one of the most effective denaturants. In 6 M GndHCl all proteins with an ordered structure lose their structure, and most of them become randomly coiled, that is, they do not contain any residual structure.</description>
  <synonyms>
    <synonym>(4-Aminobutyl) guanidine</synonym>
    <synonym>(NH2)2C=NH</synonym>
    <synonym>1184-68-5 (unspecified sulfate)</synonym>
    <synonym>1763-07-1 (unspecified phosphate)</synonym>
    <synonym>50-01-1 (mono-hydrochloride)</synonym>
    <synonym>Aminoformamidine</synonym>
    <synonym>Aminomethanamidine</synonym>
    <synonym>Bisguanidinium sulfate</synonym>
    <synonym>Carbamamidine</synonym>
    <synonym>Carbamidine</synonym>
    <synonym>GAI</synonym>
    <synonym>GU</synonym>
    <synonym>Guanidin</synonym>
    <synonym>Guanidine hydrochloride</synonym>
    <synonym>Guanidine, hydrochloride</synonym>
    <synonym>Guanidine, sulfate (2:1)</synonym>
    <synonym>Guanidinium sulfate</synonym>
    <synonym>H2N-C(=NH)-NH2</synonym>
    <synonym>Imidourea</synonym>
    <synonym>Iminourea</synonym>
    <synonym>NSC7296 (SULFATE, 2:1)</synonym>
  </synonyms>
  <chemical_formula>CH5N3</chemical_formula>
  <average_molecular_weight>59.0705</average_molecular_weight>
  <monisotopic_moleculate_weight>59.048347175</monisotopic_moleculate_weight>
  <iupac_name>guanidine</iupac_name>
  <traditional_iupac>guanidine</traditional_iupac>
  <cas_registry_number>50-01-1</cas_registry_number>
  <smiles>NC(N)=N</smiles>
  <inchi>InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)</inchi>
  <inchikey>ZRALSGWEFCBTJO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.</description>
    <direct_parent>Guanidines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic nitrogen compounds</super_class>
    <class>Organonitrogen compounds</class>
    <sub_class>Guanidines</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Guanidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imine</substituent>
      <substituent>Organopnictogen compound</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>carboxamidine</external_descriptor>
      <external_descriptor>guanidines</external_descriptor>
      <external_descriptor>one-carbon compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.92</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.15e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>182.3 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>12.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>guanidine</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>59.0705</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>59.048347175</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>NC(N)=N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>CH5N3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>ZRALSGWEFCBTJO-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>75.89</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>25.86</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>5.57</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>3</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1358</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1359</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>13460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>31353</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>170810</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16862</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16863</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>16864</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2298894</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2298895</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2298896</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2639512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2639513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2639514</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01842</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>24435</chebi_id>
  <biocyc_id/>
  <het_id>GAI</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
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    <reference>#&lt;Reference:0x000055ce32119670&gt;</reference>
    <reference>#&lt;Reference:0x000055ce321194b8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32119300&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32119148&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32118f90&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32118d60&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32118ae0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32118928&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32118770&gt;</reference>
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    <reference>#&lt;Reference:0x000055ce32118400&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32118248&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32117f50&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32117d98&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32117be0&gt;</reference>
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    <reference>#&lt;Reference:0x000055ce32117870&gt;</reference>
    <reference>#&lt;Reference:0x000055ce321176b8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32117500&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32117348&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Apple</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Malus pumila</name_scientific>
      <ncbi_taxonomy_id>283210</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Loquat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Eriobotrya japonica</name_scientific>
      <ncbi_taxonomy_id>32224</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza sativa</name_scientific>
      <ncbi_taxonomy_id>4530</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Arginine decarboxylase</name>
      <uniprot_id>Q96A70</uniprot_id>
      <uniprot_name/>
      <gene_name>ADC</gene_name>
    </enzyme>
    <enzyme>
      <name>Disks large homolog 4</name>
      <uniprot_id>P78352</uniprot_id>
      <uniprot_name/>
      <gene_name>DLG4</gene_name>
    </enzyme>
    <enzyme>
      <name>Ribonuclease pancreatic</name>
      <uniprot_id>P07998</uniprot_id>
      <uniprot_name/>
      <gene_name>RNASE1</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
    <health_effect>
      <name>Anti myasthenic</name>
      <id>454</id>
      <definition>Any substance introduced into a living organism with therapeutic or diagnostic purpose.</definition>
    </health_effect>
    <health_effect>
      <name>Convulsant</name>
      <id>832</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Hepatotoxic</name>
      <id>984</id>
      <definition>A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.</definition>
    </health_effect>
    <health_effect>
      <name>Hypertensive</name>
      <id>1007</id>
      <definition/>
    </health_effect>
    <health_effect>
      <name>Hypoglycemic</name>
      <id>1017</id>
      <definition>A drug which lowers the blood glucose level.</definition>
    </health_effect>
    <health_effect>
      <name>Myostimulant</name>
      <id>1135</id>
      <definition/>
    </health_effect>
  </health_effects>
</compound>
