<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:26:03 UTC</creation_date>
  <update_date>2015-07-21 06:57:35 UTC</update_date>
  <accession>FDB023192</accession>
  <name>Levan</name>
  <description>Levan is a substantial component of bacterial plaque produced by certain streptococci and actinomyces, and lipopolysaccharides from Gram-negative bacteria. These bacterial products are B cell mitogens which may have an adjuvant or tolerizing effect on immune responses. (PubMed ID 346320 ) [HMDB]</description>
  <synonyms>
    <synonym>(2,6-beta-D-Fructosyl)n</synonym>
    <synonym>(2,6-beta-D-Fructosyl)n+1</synonym>
    <synonym>(2,6-beta-delta-Fructosyl)n</synonym>
    <synonym>(2,6-beta-delta-Fructosyl)n+1</synonym>
    <synonym>2,6-beta-D-Fructan</synonym>
    <synonym>2,6-beta-delta-Fructan</synonym>
    <synonym>Fructan</synonym>
    <synonym>Levan n</synonym>
  </synonyms>
  <chemical_formula>C18H32O16</chemical_formula>
  <average_molecular_weight>504.4371</average_molecular_weight>
  <monisotopic_moleculate_weight>504.169034976</monisotopic_moleculate_weight>
  <iupac_name>(2R,3S,4S,5S)-5-{[(2S,3S,4S,5R)-5-({[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]methoxy}-2-(hydroxymethyl)oxolane-2,3,4-triol</iupac_name>
  <traditional_iupac>fructans</traditional_iupac>
  <cas_registry_number>9013-95-0</cas_registry_number>
  <smiles>OC[C@H]1O[C@@](CO)(OC[C@H]2O[C@@](CO)(CO[C@H]3O[C@](O)(CO)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O</smiles>
  <inchi>InChI=1S/C18H32O16/c19-1-7-9(23)14(28)18(5-22,33-7)31-2-8-10(24)12(26)16(3-20,32-8)6-30-15-11(25)13(27)17(29,4-21)34-15/h7-15,19-29H,1-6H2/t7-,8-,9-,10-,11+,12+,13+,14+,15+,16+,17-,18-/m1/s1</inchi>
  <inchikey>AIHDCSAXVMAMJH-GFBKWZILSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.</description>
    <direct_parent>O-glycosyl compounds</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>C-glycosyl compounds</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Disaccharides</alternative_parent>
      <alternative_parent>Hemiacetals</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketals</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>C-glycosyl compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Disaccharide</substituent>
      <substituent>Ether</substituent>
      <substituent>Hemiacetal</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Ketal</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.21</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.11e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-6.3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.23</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2R,3S,4S,5S)-5-{[(2S,3S,4S,5R)-5-({[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]methoxy}-2-(hydroxymethyl)oxolane-2,3,4-triol</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>504.4371</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>504.169034976</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@H]1O[C@@](CO)(OC[C@H]2O[C@@](CO)(CO[C@H]3O[C@](O)(CO)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C18H32O16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C18H32O16/c19-1-7-9(23)14(28)18(5-22,33-7)31-2-8-10(24)12(26)16(3-20,32-8)6-30-15-11(25)13(27)17(29,4-21)34-15/h7-15,19-29H,1-6H2/t7-,8-,9-,10-,11+,12+,13+,14+,15+,16+,17-,18-/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>AIHDCSAXVMAMJH-GFBKWZILSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>268.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>101.84</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>47.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>10</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>16</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>11</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::CMs</type>
      <spectrum_id>23574</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38624</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>28201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>318258</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364975</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364976</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>364977</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2689535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2689536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2689537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2989076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2989077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2989078</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB03539</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:0x000055ce33624998&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>
