<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:11:06 UTC</creation_date>
  <update_date>2025-11-19 02:41:16 UTC</update_date>
  <accession>FDB022261</accession>
  <name>N-Acetylglucosamine 6-sulfate</name>
  <description>N-acetylglucosamine 6-sulfate is a physiological intermediate during the degradation of keratan sulfate and it is usually hydrolyzed intralysosomally by N-acetylglucosamine-6-sulfate sulfatase. (PMID 3161730) [HMDB]</description>
  <synonyms>
    <synonym>4[6OSO3]glcnacbeta</synonym>
    <synonym>6-O-SulfO-N-acetyl-b-D-glucosamine</synonym>
    <synonym>6-O-SulfO-N-acetyl-beta-D-glucosamine</synonym>
    <synonym>6-O-SulfO-N-acetyl-β-D-glucosamine</synonym>
    <synonym>6-O-SulphO-N-acetyl-b-D-glucosamine</synonym>
    <synonym>6-O-SulphO-N-acetyl-beta-D-glucosamine</synonym>
    <synonym>6-O-SulphO-N-acetyl-β-D-glucosamine</synonym>
    <synonym>Aga-6-S</synonym>
    <synonym>b-D-GlcNAc6S</synonym>
    <synonym>b-D-GlcpNAc6S</synonym>
    <synonym>beta-D-GlcNAc6S</synonym>
    <synonym>beta-D-GlcpNAc6S</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulfate</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulphate</synonym>
    <synonym>N-Acetyl-D-glucosamine 6-sulphuric acid</synonym>
    <synonym>N-acetyl-Glucosamine 6-(hydrogen sulfate)</synonym>
    <synonym>N-Acetyl-glucosamine 6-(hydrogen sulphate)</synonym>
    <synonym>N-Acetylglucosamine 6-sulfate</synonym>
    <synonym>N-Acetylglucosamine 6-sulfic acid</synonym>
    <synonym>N-Acetylglucosamine 6-sulfuric acid</synonym>
    <synonym>N-Acetylglucosamine 6-sulphate</synonym>
    <synonym>N-Acetylglucosamine 6-sulphuric acid</synonym>
    <synonym>N-Acetylglucosamine-6-Sulfate</synonym>
    <synonym>β-D-glcnac6S</synonym>
    <synonym>β-D-glcpnac6S</synonym>
  </synonyms>
  <chemical_formula>C8H15NO9S</chemical_formula>
  <average_molecular_weight>301.271</average_molecular_weight>
  <monisotopic_moleculate_weight>301.046751773</monisotopic_moleculate_weight>
  <iupac_name>{[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid</iupac_name>
  <traditional_iupac>[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxysulfonic acid</traditional_iupac>
  <cas_registry_number>10356-99-7</cas_registry_number>
  <smiles>CC(=O)N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C8H15NO9S/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H,14,15,16)/t4-,5-,6-,7-,8-/m1/s1</inchi>
  <inchikey>WJFVEEAIYIOATH-FMDGEEDCSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.</description>
    <direct_parent>Acylaminosugars</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>Aliphatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>1,2-diols</alternative_parent>
      <alternative_parent>Acetamides</alternative_parent>
      <alternative_parent>Alkyl sulfates</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hexoses</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monosaccharide sulfates</alternative_parent>
      <alternative_parent>N-acyl-alpha-hexosamines</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>Secondary alcohols</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Sulfuric acid monoesters</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>1,2-diol</substituent>
      <substituent>Acetamide</substituent>
      <substituent>Acylaminosugar</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Alkyl sulfate</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hexose monosaccharide</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>Monosaccharide sulfate</substituent>
      <substituent>N-acyl-alpha-hexosamine</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic sulfuric acid or derivatives</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Polyol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Sulfate-ester</substituent>
      <substituent>Sulfuric acid ester</substituent>
      <substituent>Sulfuric acid monoester</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>amino monosaccharide</external_descriptor>
      <external_descriptor>glucosamine sulfate</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.02</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.45e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>-2.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-1.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>{[(2R,3S,4R,5R,6R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}sulfonic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>301.271</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>301.046751773</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(=O)N[C@H]1[C@H](O)O[C@H](COS(O)(=O)=O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C8H15NO9S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C8H15NO9S/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H,14,15,16)/t4-,5-,6-,7-,8-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>WJFVEEAIYIOATH-FMDGEEDCSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>162.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>57.02</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>26.71</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>8</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::CMs</type>
      <spectrum_id>13803</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37781</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>133287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>141021</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077479</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077483</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077487</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077489</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077491</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077493</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077495</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>1077497</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077499</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077501</spectrum_id>
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      <spectrum_id>1077503</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>1077505</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077507</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077509</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>1077511</spectrum_id>
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      <spectrum_id>1077513</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>1077515</spectrum_id>
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      <type>Specdb::CMs</type>
      <spectrum_id>1077516</spectrum_id>
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    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1077518</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>145450</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>145451</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>145452</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <type>Specdb::NmrOneD</type>
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      <spectrum_id>145459</spectrum_id>
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      <type>Specdb::NmrOneD</type>
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      <spectrum_id>145464</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>145465</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>145466</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>145467</spectrum_id>
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      <type>Specdb::NmrOneD</type>
      <spectrum_id>145468</spectrum_id>
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    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>145469</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50340</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50341</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>50342</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175122</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175123</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>175124</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2249365</spectrum_id>
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      <spectrum_id>2251080</spectrum_id>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2251347</spectrum_id>
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      <spectrum_id>2297467</spectrum_id>
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      <type>Specdb::MsMs</type>
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      <type>Specdb::MsMs</type>
      <spectrum_id>2638004</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2638005</spectrum_id>
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  </spectra>
  <hmdb_id>HMDB00814</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id>NGS</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x00007f093c0337d8&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c0335a8&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c0333a0&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c033148&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c032ec8&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c032ce8&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c032ab8&gt;</reference>
    <reference>#&lt;Reference:0x00007f093c032860&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
