<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-10-10 12:23:13 -0600</creation_date>
  <update_date>2015-06-03 17:26:14 -0600</update_date>
  <accession>ECMDB23234</accession>
  <m2m_id>M2MDB003624</m2m_id>
  <name>8-oxo-dGMP</name>
  <description>8-Oxo-dGMP is a metabolite of 8-oxo-dGTP which is a potent mutagenic substrate for DNA synthesis. 8-Oxo-dGTP is rapidly degraded to 8-oxo-dGMP by cellular 8-oxo-dGTPase activity. </description>
  <synonyms>
    <synonym>(2R,3S,5R)-5-(2-amino-6,8-dioxo-3,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-ylmethyl dihydrogen phosphate</synonym>
    <synonym>(2R,3S,5R)-5-(2-amino-6,8-dioxo-3,7-Dihydropurin-9-yl)-3-hydroxyoxolan-2-ylmethyl dihydrogen phosphoric acid</synonym>
    <synonym>2'-Deoxy-7,8-dihydro-8-oxo-5'-guanylate</synonym>
    <synonym>2'-deoxy-7,8-dihydro-8-oxo-5'-guanylic acid</synonym>
    <synonym>2'-deoxy-7,8-dihydro-8-oxoguanosine 5'-monophosphate</synonym>
    <synonym>2'-Deoxy-7,8-dihydro-8-oxoguanosine 5'-monophosphoric acid</synonym>
    <synonym>2'-Deoxy-8-oxo-7,8-dihydroguanosine 5'-(dihydrogen phosphate)</synonym>
    <synonym>2'-Deoxy-8-oxo-7,8-dihydroguanosine 5'-(dihydrogen phosphoric acid)</synonym>
    <synonym>8-hydroxydeoxyguanosine 5'-monophosphate</synonym>
    <synonym>8-Hydroxydeoxyguanosine 5'-monophosphoric acid</synonym>
    <synonym>8-OH-Dgmp</synonym>
    <synonym>8-oxo-2'-deoxyguanosine-5'-monophosphate</synonym>
    <synonym>8-oxo-2'-Deoxyguanosine-5'-monophosphoric acid</synonym>
    <synonym>8-Oxo-7,8-dihydro-2'-deoxyguanosine 5'-triphosphate</synonym>
    <synonym>8-oxo-7,8-dihydro-2'-Deoxyguanosine 5'-triphosphoric acid</synonym>
    <synonym>8-Oxo-dGMP</synonym>
    <synonym>8OG</synonym>
  </synonyms>
  <chemical_formula>C10H14N5O8P</chemical_formula>
  <average_molecular_weight>363.2206</average_molecular_weight>
  <monisotopic_moleculate_weight>363.057998961</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,5R)-5-(6,8-dihydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,5R)-5-(6,8-dihydroxy-2-imino-3H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxyphosphonic acid</traditional_iupac>
  <cas_registry_number/>
  <smiles>[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(O)=O)N1C(O)=NC2=C1NC(=N)N=C2O</smiles>
  <inchi>InChI=1S/C10H14N5O8P/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(23-5)2-22-24(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H2,19,20,21)(H3,11,13,14,17)/t3-,4+,5+/m0/s1</inchi>
  <inchikey>AQIVLFLYHYFRKU-VPENINKCSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.74</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.61e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>1.29</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>0.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>{[(2R,3S,5R)-5-(6,8-dihydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>363.2206</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>363.057998961</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(O)=O)N1C(O)=NC2=C1NC(=N)N=C2O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C10H14N5O8P</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C10H14N5O8P/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(23-5)2-22-24(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H2,19,20,21)(H3,11,13,14,17)/t3-,4+,5+/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AQIVLFLYHYFRKU-VPENINKCSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>202.74</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>86.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>30.46</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>-2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1084495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>4395</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334820</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334821</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334822</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334823</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334824</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334825</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334827</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334828</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>334837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>25546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32102</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32103</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>32104</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB11670</hmdb_id>
  <pubchem_compound_id>447903</pubchem_compound_id>
  <chemspider_id/>
  <kegg_id>C19968</kegg_id>
  <chebi_id>63223</chebi_id>
  <biocyc_id/>
  <het_id>G42</het_id>
  <wikipidia/>
  <foodb_id>FDB028359</foodb_id>
  <general_references>
  </general_references>
  <synthesis_reference/>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Mutator mutT protein</name>
      <uniprot_id>P08337</uniprot_id>
      <uniprot_name>MUTT_ECOLI</uniprot_name>
      <gene_name>mutT</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P08337.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>8-oxo-dGTP + Water &gt; 8-oxo-dGMP + Pyrophosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>8-oxo-dGTP + Water &lt;&gt; 8-oxo-dGMP + Pyrophosphate</reaction_text>
    <kegg_reaction_id>R09832 </kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
