<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:51 UTC</creation_date>
  <update_date>2019-11-26 02:56:02 UTC</update_date>
  <accession>FDB001161</accession>
  <name>D-Galacturonic acid</name>
  <description>obtained from the hydrolysis prods. of polymers of pectic substances

D-Galacturonic acid is a sugar acid, an oxidized form of D-galactose. It is the main component of pectin, in which it exists as the polymer polygalacturonic acid. It has an aldehyde group at C1 and a carboxylic acid group at C6. Other oxidized forms of D-galactose are D-galactonic acid (carboxylic group at C1) and meso-galactaric acid (mucic acid) (carboxylic groups at C1 and C6). It is also a uronic acid or hexuronic acid. Naturally occurring uronic acids are D-glucuronic acid, D-galacturonic acid, L-iduronic acid and D-mannuronic acid.; D-Galacturonic acid is a sugar acid, the oxidized form of D-galactose. It is the main component of pectin, in which it exists as the polymer polygalacturonic acid. -- Wikipedia. D-Galacturonic acid is found in many foods, some of which are guava, yellow wax bean, common pea, and green bean.</description>
  <synonyms>
    <synonym>(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoate</synonym>
    <synonym>(2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid</synonym>
    <synonym>3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonate</synonym>
    <synonym>3,5-Dideoxy-5-((hydroxyacetyl)amino)-D-glycero-D-galacto-2-nonulosonic acid</synonym>
    <synonym>Aldehydo-D-galacturonate</synonym>
    <synonym>Aldehydo-d-galacturonic acid</synonym>
    <synonym>D-galactopyranuronic acid</synonym>
    <synonym>D-Galacturonate</synonym>
    <synonym>D-Galacturonic acid</synonym>
    <synonym>D-galacturonic acid, homopolymer</synonym>
    <synonym>DL-galacturonic acid</synonym>
    <synonym>Galactopyranuronic acid, d-</synonym>
    <synonym>Galacturonic acid</synonym>
    <synonym>Galacturonic acid, d-</synonym>
    <synonym>N-Glycolyl-5-neuraminate</synonym>
    <synonym>N-Glycolyl-5-neuraminic acid</synonym>
    <synonym>N-Glycolyl-b-neuraminate</synonym>
    <synonym>N-Glycolyl-b-neuraminic acid</synonym>
    <synonym>N-Glycolyl-beta-neuraminate</synonym>
    <synonym>N-Glycolyl-beta-neuraminic acid</synonym>
    <synonym>N-Glycolyl-β-neuraminate</synonym>
    <synonym>N-Glycolyl-β-neuraminic acid</synonym>
    <synonym>N-Glycolylneuraminic acid</synonym>
    <synonym>Neu5gc</synonym>
  </synonyms>
  <chemical_formula>C18H30O21</chemical_formula>
  <average_molecular_weight>582.4182</average_molecular_weight>
  <monisotopic_moleculate_weight>582.127958022</monisotopic_moleculate_weight>
  <iupac_name>2,3,4,5-tetrahydroxy-6-oxohexanoic acid; 2-hydroxy-2-(3,4,5-trihydroxyoxolan-2-yl)acetic acid; 3,4,5,6-tetrahydroxyoxane-2-carboxylic acid</iupac_name>
  <traditional_iupac>D-galacturonic acid; glucuronic acid; hydroxy(3,4,5-trihydroxyoxolan-2-yl)acetic acid</traditional_iupac>
  <cas_registry_number>14982-50-4</cas_registry_number>
  <smiles>OC(C=O)C(O)C(O)C(O)C(O)=O.OC(C1OC(O)C(O)C1O)C(O)=O.OC1OC(C(O)C(O)C1O)C(O)=O</smiles>
  <inchi>InChI=1S/3C6H10O7/c7-1-2(8)6(12)13-4(1)3(9)5(10)11;7-1-2(8)4(5(10)11)13-6(12)3(1)9;7-1-2(8)3(9)4(10)5(11)6(12)13/h2*1-4,6-9,12H,(H,10,11);1-5,8-11H,(H,12,13)</inchi>
  <inchikey>TYNHVGLYUDYTJD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.</description>
    <direct_parent>Glucuronic acid derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <molecular_framework/>
    <alternative_parents>
      <alternative_parent>Alpha hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Beta hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Medium-chain fatty acids</alternative_parent>
      <alternative_parent>Medium-chain hydroxy acids and derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alpha-hydroxy acid</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Beta-hydroxy acid</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Fatty acid</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Glucuronic acid or derivatives</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy acid</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Medium-chain fatty acid</substituent>
      <substituent>Medium-chain hydroxy acid</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <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>
    <property>
      <kind>melting_point</kind>
      <value>Mp 156-159 dec. (sinters at 110°)</value>
    </property>
  </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>2,3,4,5-tetrahydroxy-6-oxohexanoic acid; 2-hydroxy-2-(3,4,5-trihydroxyoxolan-2-yl)acetic acid; 3,4,5,6-tetrahydroxyoxane-2-carboxylic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>582.4182</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>582.127958022</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC(C=O)C(O)C(O)C(O)C(O)=O.OC(C1OC(O)C(O)C1O)C(O)=O.OC1OC(C(O)C(O)C1O)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H30O21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/3C6H10O7/c7-1-2(8)6(12)13-4(1)3(9)5(10)11;7-1-2(8)4(5(10)11)13-6(12)3(1)9;7-1-2(8)3(9)4(10)5(11)6(12)13/h2*1-4,6-9,12H,(H,10,11);1-5,8-11H,(H,12,13)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>TYNHVGLYUDYTJD-UHFFFAOYSA-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>16.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>8</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>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>66528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>66529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>66530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>124122</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>124123</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>124124</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB02545</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>33830</chebi_id>
  <biocyc_id/>
  <het_id>DGU</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31d334e8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d33330&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d33178&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d32fc0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d32e08&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d32c50&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d32a98&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d328e0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d32728&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31d32570&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Apple</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Malus pumila</name_scientific>
      <ncbi_taxonomy_id>283210</ncbi_taxonomy_id>
      <average_value>3.35</average_value>
      <max_value>3.35</max_value>
      <min_value>3.35</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Bitter gourd</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Momordica charantia</name_scientific>
      <ncbi_taxonomy_id>3673</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Coconut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cocos nucifera</name_scientific>
      <ncbi_taxonomy_id>13894</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common pea</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Pisum sativum</name_scientific>
      <ncbi_taxonomy_id>3888</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden cress</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepidium sativum</name_scientific>
      <ncbi_taxonomy_id>33125</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Green bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guava</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Psidium guajava</name_scientific>
      <ncbi_taxonomy_id>120290</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Lemon</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Citrus limon</name_scientific>
      <ncbi_taxonomy_id>2708</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Papaya</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carica papaya</name_scientific>
      <ncbi_taxonomy_id>3649</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sweet basil</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ocimum basilicum</name_scientific>
      <ncbi_taxonomy_id>39350</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Yellow wax bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phaseolus vulgaris</name_scientific>
      <ncbi_taxonomy_id>3885</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>N-acylneuraminate cytidylyltransferase</name>
      <uniprot_id>Q8NFW8</uniprot_id>
      <uniprot_name/>
      <gene_name>CMAS</gene_name>
    </enzyme>
    <enzyme>
      <name>UDP-glucuronosyltransferase 1-1</name>
      <uniprot_id>P22309</uniprot_id>
      <uniprot_name/>
      <gene_name>UGT1A1</gene_name>
    </enzyme>
    <enzyme>
      <name>UDP-glucuronosyltransferase 1-4</name>
      <uniprot_id>P22310</uniprot_id>
      <uniprot_name/>
      <gene_name>UGT1A4</gene_name>
    </enzyme>
    <enzyme>
      <name>UDP-glucuronosyltransferase 1-6</name>
      <uniprot_id>P19224</uniprot_id>
      <uniprot_name/>
      <gene_name>UGT1A6</gene_name>
    </enzyme>
    <enzyme>
      <name>UDP-glucuronosyltransferase 1-9</name>
      <uniprot_id>O60656</uniprot_id>
      <uniprot_name/>
      <gene_name>UGT1A9</gene_name>
    </enzyme>
    <enzyme>
      <name>UDP-glucuronosyltransferase 2B4</name>
      <uniprot_id>P06133</uniprot_id>
      <uniprot_name/>
      <gene_name>UGT2B4</gene_name>
    </enzyme>
    <enzyme>
      <name>UDP-glucuronosyltransferase 2B7</name>
      <uniprot_id>P16662</uniprot_id>
      <uniprot_name/>
      <gene_name>UGT2B7</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
