<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2014-08-29 05:51:36 UTC</creation_date>
  <update_date>2026-04-16 22:35:40 UTC</update_date>
  <accession>T3D4192</accession>
  <common_name>Nonanal</common_name>
  <class>SmallMolecule</class>
  <description>Nonanal is an endogenous compound with the formula C9H18O and an average molecular weight of 142.24 g/mol. It exists as a solid at room temperature. Nonanal belongs to the carbonyl compounds, a subclass of organooxygen compounds within the organic compounds. Industrially, the compound is used as a fragrance, as well as a flavouring and nutrient.

Nonanal is associated with 35 recorded sources, including drinking water, indoor air, and tents or canopies. It is found in household cleaning and consumer products such as bleaching agents, cigar cigarettes, pipe accessories, tobacco pipes, and other smoking requisites. It is also present in food, food processing and cookware, specifically in food contact materials and the preparation of vinegar, wine or sparkling wine, wort, and fermentation processes for beer. Additionally, it is found in electrical and electronic equipment, including amplifiers, antennas, auxiliary devices, coils, and discharge lamps. Recorded exposure routes include oral, inhalation, and touch.

In the context of plastics, nonanal is used in high-density polyethylene and is present in polystyrene. It is released in polypropylene, polyvinyl chloride, polyethylene terephthalate, ethylene-vinyl acetate, and low-density polyethylene, while its presence in ethylene vinyl alcohol, poly(methyl methacrylate), and polyurethane remains inconclusive. Regarding biological activity, nonanal targets the organic anion transporter 3 (SLC22A8) and is a biomarker of cancer (PMC13407726).</description>
  <categories>
    <category>Uremic Toxin</category>
    <category>Food Toxin</category>
    <category>Natural Toxin</category>
  </categories>
  <types>
    <type>Organic Compound</type>
    <type>Aldehyde</type>
    <type>Food Toxin</type>
    <type>Metabolite</type>
    <type>Uremic Toxin</type>
    <type>Natural Compound</type>
  </types>
  <synonyms>
    <synonym>1-Nonaldehyde</synonym>
    <synonym>1-Nonanal</synonym>
    <synonym>1-Nonyl aldehyde</synonym>
    <synonym>C-9 aldehyde</synonym>
    <synonym>n-Nonaldehyde</synonym>
    <synonym>n-Nonan-1-al</synonym>
    <synonym>n-Nonanal</synonym>
    <synonym>Nonaldehyde</synonym>
    <synonym>Nonanaldehyde</synonym>
    <synonym>Nonanoic aldehyde</synonym>
    <synonym>Nonoic aldehyde</synonym>
    <synonym>Nonyl aldehyde</synonym>
    <synonym>Nonylaldehyde</synonym>
    <synonym>Nonylic aldehyde</synonym>
    <synonym>Pelargonaldehyde</synonym>
    <synonym>Pelargonic aldehyde</synonym>
    <synonym>Pergonal</synonym>
  </synonyms>
  <chemical_formula>C9H18O</chemical_formula>
  <average_molecular_weight>142.2386</average_molecular_weight>
  <monisotopic_moleculate_weight>142.135765198</monisotopic_moleculate_weight>
  <iupac_name>nonanal</iupac_name>
  <traditional_iupac>nonanal</traditional_iupac>
  <cas_registry_number>124-19-6</cas_registry_number>
  <smiles>CCCCCCCCC=O</smiles>
  <inchi>InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3</inchi>
  <inchikey>GYHFUZHODSMOHU-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbonyl compounds</sub_class>
    <direct_parent>Medium-chain aldehydes</direct_parent>
    <alternate_parents>
      <alternative_parent>Alpha-hydrogen aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydrogen aldehyde</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Medium-chain aldehyde</substituent>
      <substituent>Organic oxide</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Fatty aldehydes</descriptor>
      <descriptor>an &lt;i&gt;n&lt;/i&gt;-alkanal</descriptor>
      <descriptor>fatty aldehyde</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin>Endogenous</origin>
  <cellular_locations>
    <cellular_location>Membrane</cellular_location>
  </cellular_locations>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state>Solid</state>
  <appearance>White powder.</appearance>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.81</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.05e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.99</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-6.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>nonanal</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>142.2386</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>142.135765198</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCCCCCCC=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H18O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GYHFUZHODSMOHU-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>17.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>0</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>
  </predicted_properties>
  <route_of_exposure>Endogenous, Ingestion, Dermal (contact)</route_of_exposure>
  <mechanism_of_toxicity>Uremic toxins such as nonanal are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO.  KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). </mechanism_of_toxicity>
  <metabolism>Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.</metabolism>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use_source>Naturally produced by the body (endogenous).</use_source>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72248f42e0&gt;</health_effects>
  <symptoms>As a uremic toxin, this compound can cause uremic syndrome.  Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.</symptoms>
  <treatment>Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.</treatment>
  <drugbank_id/>
  <hmdb_id>HMDB59835</hmdb_id>
  <pubchem_compound_id>31289</pubchem_compound_id>
  <chembl_id>CHEMBL2228376</chembl_id>
  <chemspider_id>29029</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references>
    <reference>
      <pubmed_id>22626821</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>25041433</pubmed_id>
    </reference>
    <reference>
      <pubmed_id>22419041</pubmed_id>
    </reference>
  </general_references>
  <targets>
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      <target_id>BE0005578</target_id>
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  </targets>
</compound>
