<?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>ECMDB21243</accession>
  <m2m_id>M2MDB001651</m2m_id>
  <name>Maltohexaose</name>
  <description>Maltohexaose is hexasaccaride or more specifically a hexasaccharide comprised of six D-glucose residues connected by alpha(1-&gt;4) linkages.  It is a substrate for energy metabolism and carbon for E. coli.  Maltohexaose 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)-a-D-GLCP-(1Right4)-D-GLC</synonym>
    <synonym>a-D-Glucopyranosyl-(1Right4)-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)-alpha-D-Glcp-(1right4)-D-Glc</synonym>
    <synonym>Alpha-D-Glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-alpha-D-glucopyranosyl-(1right4)-D-glucose</synonym>
    <synonym>Maltohexanose DP6</synonym>
    <synonym>Maltohexaose</synonym>
    <synonym>α-D-GLCP-(1RIght4)-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)-α-D-glucopyranosyl-(1Right4)-D-glucose</synonym>
  </synonyms>
  <chemical_formula>C36H62O31</chemical_formula>
  <average_molecular_weight>990.8589</average_molecular_weight>
  <monisotopic_moleculate_weight>990.327505266</monisotopic_moleculate_weight>
  <iupac_name>(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</iupac_name>
  <traditional_iupac>maltohexaose</traditional_iupac>
  <cas_registry_number>34620-77-4</cas_registry_number>
  <smiles>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)C(O)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C36H62O31/c37-1-7-13(43)14(44)21(51)32(58-7)64-27-9(3-39)60-34(23(53)16(27)46)66-29-11(5-41)62-36(25(55)18(29)48)67-30-12(6-42)61-35(24(54)19(30)49)65-28-10(4-40)59-33(22(52)17(28)47)63-26-8(2-38)57-31(56)20(50)15(26)45/h7-56H,1-6H2/t7-,8-,9-,10-,11-,12-,13-,14+,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31?,32-,33-,34-,35-,36-/m1/s1</inchi>
  <inchikey>OCIBBXPLUVYKCH-LIGGPISVSA-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>-2.52</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.60</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.52e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>990.8589</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>990.327505266</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)C(O)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C36H62O31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C36H62O31/c37-1-7-13(43)14(44)21(51)32(58-7)64-27-9(3-39)60-34(23(53)16(27)46)66-29-11(5-41)62-36(25(55)18(29)48)67-30-12(6-42)61-35(24(54)19(30)49)65-28-10(4-40)59-33(22(52)17(28)47)63-26-8(2-38)57-31(56)20(50)15(26)45/h7-56H,1-6H2/t7-,8-,9-,10-,11-,12-,13-,14+,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31?,32-,33-,34-,35-,36-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>OCIBBXPLUVYKCH-LIGGPISVSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>506.13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>197.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>92.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>20</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::MsMs</type>
      <spectrum_id>38312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>38313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>38314</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>40760</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>40761</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>40762</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB12253</hmdb_id>
  <pubchem_compound_id>439606</pubchem_compound_id>
  <chemspider_id>388684</chemspider_id>
  <kegg_id>C01936</kegg_id>
  <chebi_id>27445</chebi_id>
  <biocyc_id>MALTOHEXAOSE</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>Alpha-amylase</name>
      <uniprot_id>P25718</uniprot_id>
      <uniprot_name>AMY1_ECOLI</uniprot_name>
      <gene_name>malS</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P25718.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 + Maltohexaose &gt; ADP + Hydrogen ion + Maltohexaose + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Adenosine triphosphate + Water + Maltohexaose &gt; ADP + Hydrogen ion + Maltohexaose + Phosphate</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Water + Maltoheptaose &gt; D-Glucose + Maltohexaose</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>1,4-alpha-D-glucan &gt; Maltohexaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>D-Maltose + Maltohexaose &gt; D-Glucose + Maltoheptaose</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>Maltoheptaose + Phosphate &lt;&gt; Glucose 1-phosphate + 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>a 1,4-&amp;alpha;-D-glucan + Water &gt; a 1,4-&amp;alpha;-D-glucan + Maltohexaose</reaction_text>
    <kegg_reaction_id/>
    <ecocyc_id>RXN0-5181</ecocyc_id>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
