<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:47:42 UTC</creation_date>
  <update_date>2020-04-22 15:08:43 UTC</update_date>
  <accession>BMDB0001563</accession>
  <secondary_accessions>
    <accession>BMDB01563</accession>
  </secondary_accessions>
  <name>1-Methylguanosine</name>
  <description>1-Methylguanosine, also known as M1G or TRMD protein, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. 1-Methylguanosine is possibly soluble (in water) and a moderately basic compound (based on its pKa).</description>
  <synonyms>
    <synonym>m1g</synonym>
    <synonym>N1-Methylguanosine</synonym>
    <synonym>N-Methylguanosine</synonym>
    <synonym>1-Methyl-guanosine</synonym>
    <synonym>Methylguanosine</synonym>
    <synonym>TRMD Protein</synonym>
  </synonyms>
  <chemical_formula>C11H15N5O5</chemical_formula>
  <average_molecular_weight>297.2673</average_molecular_weight>
  <monisotopic_moleculate_weight>297.107318615</monisotopic_moleculate_weight>
  <iupac_name>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one</iupac_name>
  <traditional_iupac>1-methylguanosine</traditional_iupac>
  <cas_registry_number>2140-65-0</cas_registry_number>
  <smiles>CN1C(N)=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O</smiles>
  <inchi>InChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1</inchi>
  <inchikey>UTAIYTHAJQNQDW-KQYNXXCUSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Nucleosides, nucleotides, and analogues</super_class>
    <class>Purine nucleosides</class>
    <sub_class/>
    <direct_parent>Purine nucleosides</direct_parent>
    <alternative_parents>
      <alternative_parent>6-oxopurines</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>Lactams</alternative_parent>
      <alternative_parent>N-substituted imidazoles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Pentoses</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Pyrimidones</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
      <alternative_parent>Vinylogous amides</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>6-oxopurine</substituent>
      <substituent>Alcohol</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>Imidazole</substituent>
      <substituent>Imidazopyrimidine</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monosaccharide</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>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Purine</substituent>
      <substituent>Purine nucleoside</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>
    <external_descriptors>
      <external_descriptor>methylguanosine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.27</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-2.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.45</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>1.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>297.2673</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>297.107318615</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN1C(N)=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H15N5O5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>UTAIYTHAJQNQDW-KQYNXXCUSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>146.43</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>69.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</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>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38128</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>147915</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96458</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96459</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96460</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96466</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96467</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96468</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96472</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96473</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>96477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>166631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47718</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>47720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>146669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2229440</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2230016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2235791</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2237562</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2240014</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2241675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242140</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243751</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2253064</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2253382</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2255418</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2257088</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2257488</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2259061</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2259527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2315015</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2315016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2315017</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <comment>Detected but not quantified in conventional whole milk</comment>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
    <concentration>
      <biospecimen>Milk</biospecimen>
      <concentration_value/>
      <concentration_units/>
      <references>
        <reference>
          <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
          <pubmed_id/>
        </reference>
      </references>
    </concentration>
  </normal_concentrations>
  <kegg_id>C04545</kegg_id>
  <drugbank_id/>
  <foodb_id>FDB022690</foodb_id>
  <chemspider_id>86996</chemspider_id>
  <pubchem_compound_id>96373</pubchem_compound_id>
  <knapsack_id/>
  <pdbe_id/>
  <chebi_id>19062</chebi_id>
  <meta_cyc_id>CPD0-1043</meta_cyc_id>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>7-Methylguanosine</wikipedia_id>
  <metlin_id>6324</metlin_id>
  <synthesis_reference>Ermolinsky Boris S; Efimtseva Ekaterina V; Alexeev Cyrill S; Mikhailov Sergey N; Balzarini Jan; De Clercq Erik  Dinucleoside monophosphates containing AZT and 1-methyladenosine or 7-methylguanosine.    Nucleosides, nucleotides &amp; nucleic acids  (2003),  22(5-8),  853-5.</synthesis_reference>
  <general_references>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386</reference_text>
    </reference>
    <reference>
      <reference_text>Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386   doi: 10.1007/s11306-009-0160-8</reference_text>
    </reference>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00942</protein_accession>
      <name>Protein argonaute-2</name>
      <uniprot_id>Q6QME8</uniprot_id>
      <gene_name>AGO2</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
