<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:47:25 UTC</creation_date>
  <update_date>2026-05-14 16:46:00 UTC</update_date>
  <accession/>
  <common_name>Tobramycin</common_name>
  <class>SmallMolecule</class>
  <description>Tobramycin is an organic compound with the formula C18H37N5O9 and an average molecular weight of 467.51 g/mol. Tobramycin belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds. It functions as a biological inhibitor (PMC10491871).

The compound is found in or released from 27 recorded sources. These include healthcare, pharmaceuticals and veterinary products, specifically antibiotics, antiinfectives, and aminoglycoside antibacterials. Other sources include food, food processing and cookware, such as processing meats; household items, including credit card holders; building and construction materials, such as roofs, fencing, tents or canopies, and ceilings; household cleaning and consumer products, including pipe accessories, ash trays, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and one more; and electrical and electronic equipment, including antennas, auxiliary devices, electric switches, electric hearing aids, electrically stimulated smoking devices, and seven more. Recorded exposure routes for the substance include oral, intravenous, intramuscular, respiratory, ophthalmic, and inhalation.

Regarding its health effects, tobramycin is used as a treatment for osteomyelitis (PMC9668588) and cystic fibrosis (PMC11773326). Additionally, it has a therapeutic effect on inflammation (PMC11664836).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C18H37N5O9</chemical_formula>
  <average_molecular_weight>467.5145</average_molecular_weight>
  <monisotopic_moleculate_weight>467.259127807</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol</iupac_name>
  <traditional_iupac>tobramycin</traditional_iupac>
  <cas_registry_number>32986-56-4</cas_registry_number>
  <smiles>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O</smiles>
  <inchi>InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1</inchi>
  <inchikey>NLVFBUXFDBBNBW-PBSUHMDJSA-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>4,6-disubstituted 2-deoxystreptamines</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>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>Primary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>4,6-disubstituted 2-deoxystreptamine</substituent>
      <substituent>Acetal</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic heteromonocyclic compound</substituent>
      <substituent>Amine</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 alcohol</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>amino cyclitol glycoside</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Tobramycin Action Pathway</name>
      <smpdb_id>SMP0000711</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tobramycin Action Pathway (new)</name>
      <smpdb_id>SMP0126743</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Netilmicin Action Pathway</name>
      <smpdb_id>SMP0126750</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Tobramycin Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143128</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-6.5</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.98</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.37e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-6.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>12.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2S,3R,4S,5S,6R)-4-amino-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,5S,6R)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>467.5145</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>467.259127807</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NC[C@H]1O[C@H](O[C@@H]2[C@@H](N)C[C@@H](N)[C@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O)[C@H](N)C[C@@H]1O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C18H37N5O9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C18H37N5O9/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18/h5-18,24-28H,1-4,19-23H2/t5-,6+,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>NLVFBUXFDBBNBW-PBSUHMDJSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>268.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>106.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>47.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>10</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>5</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:0x00007f7222002260&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00684</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>36294</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>33377</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>
      <target_id/>
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  </targets>
</compound>
