<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:13:43 UTC</creation_date>
  <update_date>2019-11-26 03:16:10 UTC</update_date>
  <accession>FDB018445</accession>
  <name>Zeanoside A</name>
  <description>Isolated from sweet corn kernels Zea mays (Gramineae). Zeanoside A is found in cereals and cereal products, fats and oils, and corn.</description>
  <synonyms>
    <synonym>Zeanoside A</synonym>
  </synonyms>
  <chemical_formula>C16H19NO10</chemical_formula>
  <average_molecular_weight>385.3228</average_molecular_weight>
  <monisotopic_moleculate_weight>385.100895833</monisotopic_moleculate_weight>
  <iupac_name>2-[(3S)-2,3-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-indol-3-yl]acetic acid</iupac_name>
  <traditional_iupac>[(3S)-2,3-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}indol-3-yl]acetic acid</traditional_iupac>
  <cas_registry_number>120293-55-2</cas_registry_number>
  <smiles>OC[C@H]1O[C@@H](OC2=CC=CC3=C2NC(=O)[C@]3(O)CC(O)=O)[C@H](O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C16H19NO10/c18-5-8-11(21)12(22)13(23)14(27-8)26-7-3-1-2-6-10(7)17-15(24)16(6,25)4-9(19)20/h1-3,8,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)/t8-,11-,12+,13-,14-,16+/m1/s1</inchi>
  <inchikey>VNIXZLMYLWKZLU-LGKWPGNQSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.</description>
    <direct_parent>Phenolic glycosides</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>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Indoles</alternative_parent>
      <alternative_parent>Indolines</alternative_parent>
      <alternative_parent>Indolyl carboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Lactams</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dihydroindole</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Indole or derivatives</substituent>
      <substituent>Indolyl carboxylic acid derivative</substituent>
      <substituent>Lactam</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Phenolic glycoside</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.65e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 197-198°</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-1.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>2.15</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-[(3S)-2,3-dihydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-indol-3-yl]acetic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>385.3228</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>385.100895833</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H]1O[C@@H](OC2=CC=CC3=C2NC(=O)[C@]3(O)CC(O)=O)[C@H](O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C16H19NO10</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C16H19NO10/c18-5-8-11(21)12(22)13(23)14(27-8)26-7-3-1-2-6-10(7)17-15(24)16(6,25)4-9(19)20/h1-3,8,11-14,18,21-23,25H,4-5H2,(H,17,24)(H,19,20)/t8-,11-,12+,13-,14-,16+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>VNIXZLMYLWKZLU-LGKWPGNQSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>189.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>86.55</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>35.87</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</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>-1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
  </spectra>
  <hmdb_id>HMDB38960</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32f987f0&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Breakfast cereal</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Cereals and cereal products</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fats and oils</name>
      <food_type>Unknown</food_type>
      <category>generic</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
