<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:05:19 UTC</creation_date>
  <update_date>2025-11-18 22:36:34 UTC</update_date>
  <accession>FDB002313</accession>
  <name>Narasin</name>
  <description>Ionophore effective against viruses and particularly against coccidial infections in chickens</description>
  <synonyms>
    <synonym>4-Methylsalinomycin</synonym>
    <synonym>4-Methylsalinomycin, 9CI</synonym>
    <synonym>A 28086A</synonym>
    <synonym>Antibiotic A 28086A</synonym>
    <synonym>Antibiotic C 7819B</synonym>
    <synonym>C 18-205</synonym>
    <synonym>C 7819B</synonym>
    <synonym>Lilly 79891</synonym>
    <synonym>Monteban</synonym>
    <synonym>Monteban (TN)</synonym>
    <synonym>Narasin</synonym>
    <synonym>Narasin (usp/inn)</synonym>
    <synonym>Narasin [usan:ban:inn]</synonym>
    <synonym>Narasin, BAN, INN, USAN</synonym>
    <synonym>Narasine</synonym>
    <synonym>Narasino</synonym>
    <synonym>Narasinum</synonym>
    <synonym>Narasul</synonym>
    <synonym>Salinomycin, 4-methyl-, (4S)</synonym>
  </synonyms>
  <chemical_formula>C43H72O11</chemical_formula>
  <average_molecular_weight>765.0252</average_molecular_weight>
  <monisotopic_moleculate_weight>764.507463146</monisotopic_moleculate_weight>
  <iupac_name>2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5⁷.3⁵]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid</iupac_name>
  <traditional_iupac>2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5⁷.3⁵]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid</traditional_iupac>
  <cas_registry_number>55134-13-9</cas_registry_number>
  <smiles>CCC(C1OC(C(C)C(O)C(C)C(=O)C(CC)C2OC3(OC4(CCC(C)(O4)C4CCC(O)(CC)C(C)O4)C(O)C=C3)C(C)CC2C)C(C)CC1C)C(O)=O</smiles>
  <inchi>InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)</inchi>
  <inchikey>VHKXXVVRRDYCIK-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.</description>
    <direct_parent>Diterpene glycosides</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Prenol lipids</class>
    <sub_class>Terpene glycosides</sub_class>
    <molecular_framework>Aliphatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Beta-hydroxy ketones</alternative_parent>
      <alternative_parent>Branched fatty acids</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Diterpenoids</alternative_parent>
      <alternative_parent>Fatty alcohols</alternative_parent>
      <alternative_parent>Heterocyclic fatty acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Hydroxy fatty acids</alternative_parent>
      <alternative_parent>Ketals</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Pyrans</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
      <alternative_parent>Tetrahydrofurans</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteropolycyclic compound</substituent>
      <substituent>Beta-hydroxy ketone</substituent>
      <substituent>Branched fatty acid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Diterpene glycoside</substituent>
      <substituent>Diterpenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Fatty acyl</substituent>
      <substituent>Fatty alcohol</substituent>
      <substituent>Heterocyclic fatty acid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxy fatty acid</substituent>
      <substituent>Ketal</substituent>
      <substituent>Ketone</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Pyran</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Tertiary alcohol</substituent>
      <substituent>Tetrahydrofuran</substituent>
    </substituents>
    <external_descriptors>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.50</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.41e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>Mp 198-200° (double Mp)</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>7.88</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>4.5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5⁷.3⁵]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>765.0252</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>764.507463146</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CCC(C1OC(C(C)C(O)C(C)C(=O)C(CC)C2OC3(OC4(CCC(C)(O4)C4CCC(O)(CC)C(C)O4)C(O)C=C3)C(C)CC2C)C(C)CC1C)C(O)=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C43H72O11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>VHKXXVVRRDYCIK-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>161.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>204.54</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>85.61</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>11</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</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>317350</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317351</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>317352</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363805</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363806</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>363807</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2686452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2686453</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2686454</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2992865</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2992866</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2992867</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>69638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782092</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782093</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782094</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782095</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782097</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782098</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782099</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782100</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782101</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>782102</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB30448</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:0x000055ce31a8fc28&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
