<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-06-03 10:24:24 UTC</creation_date>
  <update_date>2026-08-22 05:35:08 UTC</update_date>
  <accession/>
  <common_name>viomycin</common_name>
  <class>SmallMolecule</class>
  <description>Viomycin is an organic compound with the formula C25H43N13O10. Viomycin belongs to the hybrid peptides, a subclass of peptidomimetics within the organic compounds. With an average molecular weight of 685.69 g/mol, viomycin is a heavy molecule. It is found in healthcare, pharmaceuticals, and veterinary products as an antibiotic. Recorded exposure routes for this compound include oral and inhalation. In terms of biological activity, viomycin acts as an inhibitor of the 16S/23S rRNA (cytidine-2'-O)-methyltransferase TlyA (tlyA) protein target.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C25H43N13O10</chemical_formula>
  <average_molecular_weight>685.69</average_molecular_weight>
  <monisotopic_moleculate_weight>685.325584661</monisotopic_moleculate_weight>
  <iupac_name>(3S)-3,6-diamino-N-[(3S,6Z,9S,12S,15S)-6-[(carbamoylamino)methylidene]-3-[(4R,6S)-6-hydroxy-2-imino-1,3-diazinan-4-yl]-9,12-bis(hydroxymethyl)-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-15-yl]hexanamide</iupac_name>
  <traditional_iupac>viomycine</traditional_iupac>
  <cas_registry_number>32988-50-4</cas_registry_number>
  <smiles>[H][C@@]1(C[C@H](O)NC(=N)N1)[C@]1([H])NC(=O)\C(NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CNC1=O)NC(=O)C[C@@H](N)CCCN)=C\NC(N)=O</smiles>
  <inchi>InChI=1S/C25H43N13O10/c26-3-1-2-10(27)4-16(41)32-12-6-30-23(47)18(11-5-17(42)37-24(28)36-11)38-20(44)13(7-31-25(29)48)33-21(45)14(8-39)35-22(46)15(9-40)34-19(12)43/h7,10-12,14-15,17-18,39-40,42H,1-6,8-9,26-27H2,(H,30,47)(H,32,41)(H,33,45)(H,34,43)(H,35,46)(H,38,44)(H3,28,36,37)(H3,29,31,48)/b13-7-/t10-,11+,12-,14-,15-,17-,18-/m0/s1</inchi>
  <inchikey>GXFAIFRPOKBQRV-GHXCTMGLSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenoxyacetic acid derivatives</sub_class>
    <direct_parent>Phenoxyacetic acid derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Dicarboximides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Thiazolidinediones</alternative_parent>
      <alternative_parent>Thiocarbamic acid derivatives</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Dicarboximide</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenoxyacetate</substituent>
      <substituent>Thiazolidine</substituent>
      <substituent>Thiazolidinedione</substituent>
      <substituent>Thiocarbamic acid derivative</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Viomycin Action Pathway</name>
      <smpdb_id>SMP0126771</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Viomycin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144159</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-11</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-3.43</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.04e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(3S)-3,6-diamino-N-[(3S,6Z,9S,12S,15S)-6-[(carbamoylamino)methylidene]-3-[(4R,6S)-6-hydroxy-2-imino-1,3-diazinan-4-yl]-9,12-bis(hydroxymethyl)-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-15-yl]hexanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>685.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>685.325584661</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]1(C[C@H](O)NC(=N)N1)[C@]1([H])NC(=O)\C(NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CNC1=O)NC(=O)C[C@@H](N)CCCN)=C\NC(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C25H43N13O10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C25H43N13O10/c26-3-1-2-10(27)4-16(41)32-12-6-30-23(47)18(11-5-17(42)37-24(28)36-11)38-20(44)13(7-31-25(29)48)33-21(45)14(8-39)35-22(46)15(9-40)34-19(12)43/h7,10-12,14-15,17-18,39-40,42H,1-6,8-9,26-27H2,(H,30,47)(H,32,41)(H,33,45)(H,34,43)(H,35,46)(H,38,44)(H3,28,36,37)(H3,29,31,48)/b13-7-/t10-,11+,12-,14-,15-,17-,18-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GXFAIFRPOKBQRV-GHXCTMGLSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>390.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>171.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>66.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72676a74e0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB06827</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>3037981</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>2301596</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
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    <target>
      <target_id>BE0009727</target_id>
      <mechanism_of_action/>
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  </targets>
</compound>
