<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-07-30 14:55:05 -0600</creation_date>
  <update_date>2015-06-03 17:20:59 -0600</update_date>
  <accession>ECMDB21244</accession>
  <m2m_id>M2MDB001652</m2m_id>
  <name>Maltopentaose</name>
  <description>Maltopentaose is pentasaccaride or more specifically a pentasaccharide comprised of five D-glucose residues connected by alpha(1-&gt;4) linkages.  It is a substrate for energy metabolism and carbon for E. coli.  Maltopentaose is imported into the cell via the maltooligosaccharide-specific LamB-channel of Escherichia coli (also called maltoporin).  It is degraded by alpha amylase.</description>
  <synonyms>
    <synonym>a-D-GLCP-(1RIght4)-a-D-GLCP-(1Right4)-a-D-GLCP-(1Right4)-a-D-GLCP-(1Right4)-D-GLC</synonym>
    <synonym>a-D-Glucopyranosyl-(1Right4)-a-D-glucopyranosyl-(1Right4)-a-D-glucopyranosyl-(1Right4)-a-D-glucopyranosyl-(1Right4)-D-glucose</synonym>
    <synonym>Alpha-D-Glcp-(1right4)-alpha-D-Glcp-(1right4)-alpha-D-Glcp-(1right4)-alpha-D-Glcp-(1right4)-D-Glc</synonym>
    <synonym>Alpha-D-Glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-D-glucose</synonym>
    <synonym>α-D-GLCP-(1RIght4)-α-D-GLCP-(1Right4)-α-D-GLCP-(1Right4)-α-D-GLCP-(1Right4)-D-GLC</synonym>
    <synonym>α-D-Glucopyranosyl-(1Right4)-α-D-glucopyranosyl-(1Right4)-α-D-glucopyranosyl-(1Right4)-α-D-glucopyranosyl-(1Right4)-D-glucose</synonym>
  </synonyms>
  <chemical_formula>C27H48O26</chemical_formula>
  <average_molecular_weight>788.6544</average_molecular_weight>
  <monisotopic_moleculate_weight>788.243381708</monisotopic_moleculate_weight>
  <iupac_name>6-({6-[(6-{[4,5-dihydroxy-2-(hydroxymethyl)-6-[2,3,4-trihydroxy-1-(hydroxymethoxy)butoxy]oxan-3-yl]oxy}-2,4,5-trihydroxyoxan-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxy)oxane-2,3,4,5-tetrol</iupac_name>
  <traditional_iupac>6-({6-[(6-{[4,5-dihydroxy-2-(hydroxymethyl)-6-[2,3,4-trihydroxy-1-(hydroxymethoxy)butoxy]oxan-3-yl]oxy}-2,4,5-trihydroxyoxan-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxy)oxane-2,3,4,5-tetrol</traditional_iupac>
  <cas_registry_number>34620-76-3</cas_registry_number>
  <smiles>OCOC(OC1OC(CO)C(OC2OC(O)C(OC3OC(CO)C(OC4OC(O)C(O)C(O)C4O)C(O)C3O)C(O)C2O)C(O)C1O)C(O)C(O)CO</smiles>
  <inchi>InChI=1S/C27H48O26/c28-1-5(32)8(33)23(45-4-31)53-25-16(41)11(36)19(7(3-30)47-25)49-27-17(42)12(37)20(22(44)52-27)50-24-15(40)10(35)18(6(2-29)46-24)48-26-14(39)9(34)13(38)21(43)51-26/h5-44H,1-4H2</inchi>
  <inchikey>JAEVVUVBPPQABG-UHFFFAOYSA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
    <cellular_location>Cytosol</cellular_location>
    <cellular_location>Extra-organism</cellular_location>
    <cellular_location>Periplasm</cellular_location>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.55</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.22e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-9.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.89</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>6-({6-[(6-{[4,5-dihydroxy-2-(hydroxymethyl)-6-[2,3,4-trihydroxy-1-(hydroxymethoxy)butoxy]oxan-3-yl]oxy}-2,4,5-trihydroxyoxan-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxy)oxane-2,3,4,5-tetrol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>788.6544</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>788.243381708</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OCOC(OC1OC(CO)C(OC2OC(O)C(OC3OC(CO)C(OC4OC(O)C(O)C(O)C4O)C(O)C3O)C(O)C2O)C(O)C1O)C(O)C(O)CO</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C27H48O26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C27H48O26/c28-1-5(32)8(33)23(45-4-31)53-25-16(41)11(36)19(7(3-30)47-25)49-27-17(42)12(37)20(22(44)52-27)50-24-15(40)10(35)18(6(2-29)46-24)48-26-14(39)9(34)13(38)21(43)51-26/h5-44H,1-4H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>JAEVVUVBPPQABG-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>426.98</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>153.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>72.78</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>26</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>17</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1083891</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>3377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341669</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341670</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341678</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341679</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341680</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341681</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341682</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341683</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341684</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341685</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341686</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>341687</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>37493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>37494</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>37495</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>39941</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>39942</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>39943</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB12254</hmdb_id>
  <pubchem_compound_id>124005</pubchem_compound_id>
  <chemspider_id>21229918</chemspider_id>
  <kegg_id/>
  <chebi_id>62006</chebi_id>
  <biocyc_id>MALTOPENTAOSE</biocyc_id>
  <het_id/>
  <wikipidia/>
  <foodb_id/>
  <general_references>
  </general_references>
  <synthesis_reference/>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Maltodextrin phosphorylase</name>
      <uniprot_id>P00490</uniprot_id>
      <uniprot_name>PHSM_ECOLI</uniprot_name>
      <gene_name>malP</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P00490.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>4-alpha-glucanotransferase</name>
      <uniprot_id>P15977</uniprot_id>
      <uniprot_name>MALQ_ECOLI</uniprot_name>
      <gene_name>malQ</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P15977.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltodextrin glucosidase</name>
      <uniprot_id>P21517</uniprot_id>
      <uniprot_name>MALZ_ECOLI</uniprot_name>
      <gene_name>malZ</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P21517.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Cytoplasmic alpha-amylase</name>
      <uniprot_id>P26612</uniprot_id>
      <uniprot_name>AMY2_ECOLI</uniprot_name>
      <gene_name>amyA</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P26612.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose/maltodextrin import ATP-binding protein MalK</name>
      <uniprot_id>P68187</uniprot_id>
      <uniprot_name>MALK_ECOLI</uniprot_name>
      <gene_name>malK</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68187.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malF</name>
      <uniprot_id>P02916</uniprot_id>
      <uniprot_name>MALF_ECOLI</uniprot_name>
      <gene_name>malF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02916.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malG</name>
      <uniprot_id>P68183</uniprot_id>
      <uniprot_name>MALG_ECOLI</uniprot_name>
      <gene_name>malG</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68183.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose-binding periplasmic protein</name>
      <uniprot_id>P0AEX9</uniprot_id>
      <uniprot_name>MALE_ECOLI</uniprot_name>
      <gene_name>malE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AEX9.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
    <enzyme>
      <name>Maltose/maltodextrin import ATP-binding protein MalK</name>
      <uniprot_id>P68187</uniprot_id>
      <uniprot_name>MALK_ECOLI</uniprot_name>
      <gene_name>malK</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68187.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malF</name>
      <uniprot_id>P02916</uniprot_id>
      <uniprot_name>MALF_ECOLI</uniprot_name>
      <gene_name>malF</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02916.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose transport system permease protein malG</name>
      <uniprot_id>P68183</uniprot_id>
      <uniprot_name>MALG_ECOLI</uniprot_name>
      <gene_name>malG</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P68183.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltose-binding periplasmic protein</name>
      <uniprot_id>P0AEX9</uniprot_id>
      <uniprot_name>MALE_ECOLI</uniprot_name>
      <gene_name>malE</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P0AEX9.xml</protein_url>
    </enzyme>
    <enzyme>
      <name>Maltoporin</name>
      <uniprot_id>P02943</uniprot_id>
      <uniprot_name>LAMB_ECOLI</uniprot_name>
      <gene_name>lamB</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P02943.xml</protein_url>
    </enzyme>
  </transporters>
  <reactions>
    <reaction_text>Adenosine triphosphate + Water + Maltopentaose &gt; ADP + Hydrogen ion + Maltopentaose + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Water + Maltopentaose &gt; ADP + Hydrogen ion + Maltopentaose + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Water + Maltohexaose &gt; D-Glucose + Maltopentaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Water + Maltopentaose &gt; D-Glucose + Maltotetraose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>D-Maltose + Maltotetraose &gt; D-Glucose + Maltopentaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>D-Maltose + Maltopentaose &gt; D-Glucose + Maltohexaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Maltohexaose + Phosphate &lt;&gt; Glucose 1-phosphate + Maltopentaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Maltopentaose + Phosphate &lt;&gt; Glucose 1-phosphate + Maltotetraose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>a 1,4-&amp;alpha;-D-glucan + Water &gt; a 1,4-&amp;alpha;-D-glucan + Maltopentaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>ALPHA-AMYL-RXN</ecocyc_id>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
