<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2026-03-31 20:20:29 UTC</creation_date>
  <update_date>2026-05-14 19:23:35 UTC</update_date>
  <accession/>
  <common_name>Sisomicin</common_name>
  <class>SmallMolecule</class>
  <description>Sisomicin is an organic compound with the chemical formula C19H37N5O7 and an average molecular weight of 447.53 g/mol. Sisomicin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds.

This substance is recorded as being found in or released from 16 different sources. Within the healthcare, pharmaceuticals, and veterinary products category, it is used as an antibiotic. Other recorded sources include building and construction materials, specifically roofs, tents, or canopies. Additionally, it is associated with electrical and electronic equipment, including amplifiers, antennas, auxiliary devices, colour television systems, and communication cables or conductors, among eight other devices. Recorded routes of exposure for this compound include oral and inhalation.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yloxy]-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside</synonym>
    <synonym>(1S,2S,3R,4S,6R)-4,6-Diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranoside</synonym>
    <synonym>(1S,2S,3R,4S,6R)-4,6-Diamino-3-{[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosido</synonym>
    <synonym>(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxy-cyclohexoxy]-5-methyl-4-methylamino-tetrahydropyran-3,5-diol</synonym>
    <synonym>(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxy-cyclohexyl]oxy-5-methyl-4-methylamino-oxane-3,5-diol</synonym>
    <synonym>(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexoxy]-5-methyl-4-methylaminotetrahydropyran-3,5-diol</synonym>
    <synonym>(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol</synonym>
    <synonym>(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol</synonym>
    <synonym>(2R,3R,4R,5R)-2-{3-[(2S,3R)-3-amino-6-(aminomethyl)(2H-3,4-dihydropyran-2-yloxy)](1S,4S,2R,3R,6R)-4,6-diamino-2-hydroxycyclohexyloxy}-5-methyl-4-(methylamino)-2H-3,4,5,6-tetrahydropyran-3,5-diol</synonym>
    <synonym>(2S-cis)-4-O-(3-Amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl)-2-deoxy-6-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl)-D-streptamine</synonym>
    <synonym>251-018-2</synonym>
    <synonym>32385-11-8 (FREE BASE)</synonym>
    <synonym>4,5-Dehydrogentamicin</synonym>
    <synonym>53179-09-2 (2:5 PENTASULFATE SALT)</synonym>
    <synonym>Antibiotic 66-40</synonym>
    <synonym>Antibiotic 6640</synonym>
    <synonym>bactoCeaze</synonym>
    <synonym>beta-L-Arabinopyranoside, (1S,2S,3R,4S,6R)-4,6-diamino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-2-hydroxycyclohexyl 3-deoxy-4-C-methyl-3-(methylamino)-</synonym>
    <synonym>C19H37N5O7</synonym>
    <synonym>CHEBI:9169</synonym>
    <synonym>D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-</synonym>
    <synonym>Dehydrogentamicin Cla</synonym>
    <synonym>E'sisomicin'</synonym>
    <synonym>EINECS 251-018-2</synonym>
    <synonym>Ensamycin</synonym>
    <synonym>Extramycin</synonym>
    <synonym>MFCD00865123</synonym>
    <synonym>O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6))-2-deoxy-D-streptamine</synonym>
    <synonym>O-2,6-Diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-2-deoxy-D-streptamine</synonym>
    <synonym>O-3-Deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-4)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-6))-2-deoxy-L-streptamine</synonym>
    <synonym>Pathomycin</synonym>
    <synonym>Rickamicin</synonym>
    <synonym>Salvamina</synonym>
    <synonym>SIS</synonym>
    <synonym>Siseptin</synonym>
    <synonym>Siseptin sulfate</synonym>
    <synonym>SISO</synonym>
    <synonym>Sisomicin</synonym>
    <synonym>Sisomicin (USAN)</synonym>
    <synonym>SISOMICIN SULFATE</synonym>
    <synonym>Sisomicin [USAN:INN]</synonym>
    <synonym>Sisomicina [INN-Spanish]</synonym>
    <synonym>Sisomicine [INN-French]</synonym>
    <synonym>Sisomicinum [INN-Latin]</synonym>
    <synonym>sisomycin</synonym>
    <synonym>Sissomicin</synonym>
    <synonym>Sissomicin [BAN]</synonym>
    <synonym>Sizomycin</synonym>
    <synonym>UNII-X55XSL74YQ</synonym>
    <synonym>UNII:X55XSL74YQ</synonym>
    <synonym>[32385-11-8]</synonym>
  </synonyms>
  <chemical_formula>C19H37N5O7</chemical_formula>
  <average_molecular_weight>447.533</average_molecular_weight>
  <monisotopic_moleculate_weight>447.269299</monisotopic_moleculate_weight>
  <iupac_name/>
  <traditional_iupac/>
  <cas_registry_number>32385-11-8</cas_registry_number>
  <smiles>CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](OC3OC(CN)=CCC3N)[C@@H]2O)OC[C@]1(C)O</smiles>
  <inchi>InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1</inchi>
  <inchikey>URWAJWIAIPFPJE-YFMIWBNJSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <direct_parent>Aminocyclitol glycosides</direct_parent>
    <alternate_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Aminocyclitols and derivatives</alternative_parent>
      <alternative_parent>Cyclohexanols</alternative_parent>
      <alternative_parent>Cyclohexylamines</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Monosaccharides</alternative_parent>
      <alternative_parent>O-glycosyl compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
      <alternative_parent>Oxanes</alternative_parent>
      <alternative_parent>Tertiary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Amino cyclitol glycoside</substituent>
      <substituent>Aminocyclitol or derivatives</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Cyclitol or derivatives</substituent>
      <substituent>Cyclohexanol</substituent>
      <substituent>Cyclohexylamine</substituent>
      <substituent>Glycosyl compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monosaccharide</substituent>
      <substituent>O-glycosyl compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Oxane</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Tertiary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-4.3</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>average_mass</kind>
      <value>447.533</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>447.269299</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN[C@@H]1[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](OC3OC(CN)=CCC3N)[C@@H]2O)OC[C@]1(C)O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H37N5O7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12+,13-,14-,15+,16-,17-,18-,19+/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>URWAJWIAIPFPJE-YFMIWBNJSA-N</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:0x00007f3bf3920820&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB12604</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>36119</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>33222</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
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  </targets>
</compound>
