<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>2.0</version>
  <creation_date>2012-08-09 09:16:16 -0600</creation_date>
  <update_date>2015-06-03 17:21:31 -0600</update_date>
  <accession>ECMDB21445</accession>
  <m2m_id>M2MDB001840</m2m_id>
  <name>Pectic acid</name>
  <description>Pectic acid is also known as polygalacturonic acid. (Wikipedia)  In E. coli, pectic acid can be produced from pectin in a reaction catalyzed by pectinesterase (EC 3.1.1.11). (KEGG)</description>
  <synonyms>
    <synonym>(1,4-&amp;alpha;-D-Galacturonosyl)n</synonym>
    <synonym>1,4-&amp;alpha;-D-galacturonide</synonym>
    <synonym>a Pectate</synonym>
    <synonym>A pectic acid</synonym>
    <synonym>A poly(1,4-&amp;alpha;-D-galacturonate)</synonym>
    <synonym>a Poly(1,4-&amp;alpha;-D-galacturonic acid)</synonym>
    <synonym>a-delta-Galactopyranuronate</synonym>
    <synonym>a-delta-Galactopyranuronic acid</synonym>
    <synonym>a-delta-Galacturonate</synonym>
    <synonym>a-delta-Galacturonic acid</synonym>
    <synonym>a-delta-Polygalacturonate</synonym>
    <synonym>a-delta-Polygalacturonic acid</synonym>
    <synonym>a-δ-Galactopyranuronate</synonym>
    <synonym>a-δ-Galactopyranuronic acid</synonym>
    <synonym>a-δ-Galacturonate</synonym>
    <synonym>a-δ-Galacturonic acid</synonym>
    <synonym>a-δ-Polygalacturonate</synonym>
    <synonym>a-δ-Polygalacturonic acid</synonym>
    <synonym>alpha-delta-Galactopyranuronate</synonym>
    <synonym>Alpha-delta-galactopyranuronic acid</synonym>
    <synonym>alpha-delta-Galacturonate</synonym>
    <synonym>Alpha-delta-galacturonic acid</synonym>
    <synonym>alpha-delta-Polygalacturonate</synonym>
    <synonym>Alpha-delta-polygalacturonic acid</synonym>
    <synonym>An &amp;alpha;-D-polygalacturonate</synonym>
    <synonym>An &amp;alpha;-D-polygalacturonic acid</synonym>
    <synonym>Calcium pectate</synonym>
    <synonym>Calcium pectic acid</synonym>
    <synonym>Calcium polygalacturonate</synonym>
    <synonym>Calcium polygalacturonic acid</synonym>
    <synonym>D-galacturonan</synonym>
    <synonym>D-galacturonate</synonym>
    <synonym>D-Galacturonic acid</synonym>
    <synonym>Delta-galacturonan</synonym>
    <synonym>Delta-galacturonate</synonym>
    <synonym>Delta-Galacturonic acid</synonym>
    <synonym>Galacturonan</synonym>
    <synonym>Galacturonate</synonym>
    <synonym>Galacturonic acid</synonym>
    <synonym>Pectate</synonym>
    <synonym>Poly(1,4-&amp;alpha;-D-galacturonate)(n)</synonym>
    <synonym>Poly(1,4-&amp;alpha;-D-galacturonic acid)(N)</synonym>
    <synonym>Poly(1,4-a-D-galacturonate)</synonym>
    <synonym>Poly(1,4-a-D-galacturonic acid)</synonym>
    <synonym>Poly(1,4-a-delta-galacturonate)</synonym>
    <synonym>Poly(1,4-a-delta-galacturonic acid)</synonym>
    <synonym>Poly(1,4-a-δ-galacturonate)</synonym>
    <synonym>Poly(1,4-a-δ-galacturonic acid)</synonym>
    <synonym>Poly(1,4-alpha-D-galacturonate)</synonym>
    <synonym>Poly(1,4-alpha-D-galacturonic acid)</synonym>
    <synonym>Poly(1,4-alpha-delta-galacturonate)</synonym>
    <synonym>Poly(1,4-alpha-delta-galacturonic acid)</synonym>
    <synonym>Poly(1,4-α-D-galacturonate)</synonym>
    <synonym>Poly(1,4-α-D-galacturonic acid)</synonym>
    <synonym>Poly(1,4-α-δ-galacturonate)</synonym>
    <synonym>Poly(1,4-α-δ-galacturonic acid)</synonym>
    <synonym>Polygalacturonate</synonym>
    <synonym>Polygalacturonic acid</synonym>
    <synonym>Sodium pectate</synonym>
    <synonym>Sodium pectic acid</synonym>
    <synonym>Sulfated polygalacturonate</synonym>
    <synonym>Sulfated polygalacturonic acid</synonym>
    <synonym>Sulphated polygalacturonate</synonym>
    <synonym>Sulphated polygalacturonic acid</synonym>
    <synonym>α-δ-Galactopyranuronate</synonym>
    <synonym>α-δ-Galactopyranuronic acid</synonym>
    <synonym>α-δ-Galacturonate</synonym>
    <synonym>α-δ-Galacturonic acid</synonym>
    <synonym>α-δ-Polygalacturonate</synonym>
    <synonym>α-δ-Polygalacturonic acid</synonym>
    <synonym>δ-Galacturonan</synonym>
    <synonym>δ-Galacturonate</synonym>
    <synonym>δ-Galacturonic acid</synonym>
  </synonyms>
  <chemical_formula>C6H10O7</chemical_formula>
  <average_molecular_weight>194.1394</average_molecular_weight>
  <monisotopic_moleculate_weight>194.042652674</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>α-D-galacturonic acid</traditional_iupac>
  <cas_registry_number></cas_registry_number>
  <smiles>O[C@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C(O)=O</smiles>
  <inchi>InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6-/m0/s1</inchi>
  <inchikey>AEMOLEFTQBMNLQ-BKBMJHBISA-N</inchikey>
  <state>Solid</state>
  <cellular_locations>
  </cellular_locations>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.95e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.6</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>3.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S,3R,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>194.1394</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>194.042652674</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>O[C@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C6H10O7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2+,3+,4-,6-/m0/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AEMOLEFTQBMNLQ-BKBMJHBISA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>127.45</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>35.79</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>16.27</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>5</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>
    <pathway>
      <name>Starch and sucrose metabolism</name>
      <description>The metabolism of starch and sucrose begins with D-fructose interacting with a D-glucose in a reversible reaction through a maltodextrin glucosidase resulting in a water molecule and a sucrose. D-fructose is phosphorylated through an ATP driven fructokinase resulting in the release of an ADP, a hydrogen ion and a Beta-D-fructofuranose 6-phosphate. This compound can also be introduced into the cytoplasm through either a mannose PTS permease or a hexose-6-phosphate:phosphate antiporter. 
The Beta-D-fructofuranose 6-phosphate is isomerized through a phosphoglucose isomerase resulting in a Beta-D-glucose 6-phosphate. This compound can also be incorporated by glucose PTS permease or a hexose-6-phosphate:phosphate antiporter. 
The beta-D-glucose 6 phosphate can also be produced by a D-glucose being phosphorylated by an ATP-driven glucokinase resulting in a ADP, a hydrogen ion and a Beta-D-glucose 6 phosphate. 

The beta-D-glucose can produce alpha-D-glucose-1-phosphate  by two methods:
1.-Beta-D-glucose is isomerized into an alpha-D-Glucose 6-phosphate and then interacts in a reversible reaction through a phosphoglucomutase-1 resulting in a alpha-D-glucose-1-phosphate.
2.-Beta-D-glucose interacts with a putative beta-phosphoglucomutase resulting in a Beta-D-glucose 1-phosphate.  Beta-D-glucose 1-phosphate can be incorporated into the cytoplasm through a 
glucose PTS permease. This compound is then isomerized into a Alpha-D-glucose-1-phosphate
The beta-D-glucose can cycle back into a D-fructose by first interacting with D-fructose in a reversible reaction through a Polypeptide: predicted glucosyltransferase resulting in the release of a phosphate and a sucrose. The sucrose then interacts in a reversible reaction with a water molecule through a maltodextrin glucosidase resulting in a D-glucose and a D-fructose. 

Alpha-D-glucose-1-phosphate can produce glycogen in by two different sets of reactions:
1.-Alpha-D-glucose-1-phosphate interacts with a hydrogen ion and an ATP through a glucose-1-phosphate adenylyltransferase resulting in a pyrophosphate and an ADP-glucose. The ADP-glucose then interacts with an amylose through a glycogen synthase resulting in the release of an ADP and an Amylose. The amylose then interacts with 1,4-α-glucan branching enzyme resulting in glycogen
2.- Alpha-D-glucose-1-phosphate interacts with amylose through a maltodextrin phosphorylase resulting in a phosphate and a glycogen.

Alpha-D-glucose-1-phosphate can also interacts with UDP-galactose through a galactose-1-phosphate uridylyltransferase resulting in a galactose 1-phosphate and a Uridine diphosphate glucose. The UDP-glucose then interacts with an alpha-D-glucose 6-phosphate through a trehalose-6-phosphate synthase resulting in a uridine 5'-diphosphate, a hydrogen ion and a Trehalose 6- phosphate. The latter compound can also be incorporated into the cytoplasm through a trehalose PTS permease. Trehalose interacts with a water molecule through a trehalose-6-phosphate phosphatase resulting in the release of a phosphate and an alpha,alpha-trehalose.The alpha,alpha-trehalose can also be obtained from glycogen being metabolized through a glycogen debranching enzyme resulting in a the alpha, alpha-trehalose. This compound ca then be hydrated through a cytoplasmic trehalase resulting in the release of an alpha-D-glucose and a beta-d-glucose.

Glycogen is then metabolized by reacting with a phosphate through a glycogen phosphorylase resulting in a alpha-D-glucose-1-phosphate and a dextrin. The dextrin is then hydrated through a glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase resulting in the release of a debranched limit dextrin and a maltotetraose. This compound can also be incorporated into the cytoplasm through a 
maltose ABC transporter. The maltotetraose interacts with a phosphate through a maltodextrin phosphorylase releasing a alpha-D-glucose-1-phosphate and a maltotriose. The maltotriose can also be incorporated through a maltose ABC transporter. The maltotriose can then interact with water through a maltodextrin glucosidase resulting in a D-glucose and a D-maltose. D-maltose can also be incorporated through a 
maltose ABC transporter 

The D-maltose can then interact with a maltotriose through a amylomaltase resulting in a maltotetraose and a D-glucose. The D-glucose is then phosphorylated through an ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate</description>
      <pathwhiz_id>PW000941</pathwhiz_id>
      <kegg_map_id>ec00500</kegg_map_id>
      <subject>Metabolic</subject>
    </pathway>
    <pathway>
      <name>Pentose and glucuronate interconversions</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>ec00040</kegg_map_id>
      <subject/>
    </pathway>
    <pathway>
      <name>Metabolic pathways</name>
      <description/>
      <pathwhiz_id/>
      <kegg_map_id>eco01100</kegg_map_id>
      <subject/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9952</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>160219</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135835</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135836</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135837</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135838</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135839</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135843</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135844</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135845</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135846</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135847</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135848</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>135849</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27911</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>27913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34469</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34470</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>34471</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2737369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2737370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2737371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2968404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2968405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2968406</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB03363</hmdb_id>
  <pubchem_compound_id>445929</pubchem_compound_id>
  <chemspider_id>393411</chemspider_id>
  <kegg_id>C00470</kegg_id>
  <chebi_id>62969</chebi_id>
  <biocyc_id>PECTATE</biocyc_id>
  <het_id>ADA</het_id>
  <wikipidia>Pectate</wikipidia>
  <foodb_id></foodb_id>
  <general_references>
    <reference>
      <reference_text>van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.</reference_text>
      <pubmed_id>17765195</pubmed_id>
    </reference>
    <reference>
      <reference_text>Serban D, Rordorf-Adam C: Binding characteristics of human serum amyloid P component.  Scand J Immunol. 1987 Mar;25(3):275-81.</reference_text>
      <pubmed_id>3105045</pubmed_id>
    </reference>
    <reference>
      <reference_text>Nakajima N, Ishihara K, Matsuura Y: Dietary-fiber-degrading enzymes from a human intestinal Clostridium and their application to oligosaccharide production from nonstarchy polysaccharides using immobilized cells. Appl Microbiol Biotechnol. 2002 Jul;59(2-3):182-9. Epub 2002 May 3.</reference_text>
      <pubmed_id>12111144</pubmed_id>
    </reference>
  </general_references>
  <synthesis_reference></synthesis_reference>
  <msds_url/>
  <enzymes>
    <enzyme>
      <name>Putative acyl-CoA thioester hydrolase ybhC</name>
      <uniprot_id>P46130</uniprot_id>
      <uniprot_name>YBHC_ECOLI</uniprot_name>
      <gene_name>ybhC</gene_name>
      <protein_url>http://ecmdb.ca/proteins/P46130.xml</protein_url>
    </enzyme>
  </enzymes>
  <transporters>
  </transporters>
  <reactions>
    <reaction_text>L-Lyxose + Water &lt;&gt; Methanol + Pectic acid</reaction_text>
    <kegg_reaction_id>R02362</kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
    <reaction_text>Pectin + Water &lt;&gt; Methanol + Pectic acid</reaction_text>
    <kegg_reaction_id>R02362 R06250 </kegg_reaction_id>
    <ecocyc_id/>
    <pw_reaction_id/>
  </reactions>
  <concentrations>
  </concentrations>
</compound>
