<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4235</id>
  <title>T3D4181</title>
  <common-name>Hexanal</common-name>
  <description>Hexanal is a uremic toxin.  Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Hexanal is an alkyl aldehyde found in human biofluids. Human milk samples collected from women contains hexanal. Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal are associated with poorer patient prognosis. Hexanal is a volatile compound that has been associated with the development of undesirable flavours. The content of hexanal, which is a major breakdown product of linoleic acid (LA, n - 6 PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods, and have been proposed as one potential marker of milk quality. A cardboard-like off-flavour is frequently associated with dehydrated milk products. This effect is highly correlated with the headspace concentration of hexanal. (A7871, A7872).</description>
  <cas>66-25-1</cas>
  <pubchem-id>6184</pubchem-id>
  <chemical-formula>C6H12O</chemical-formula>
  <weight>100.16</weight>
  <appearance nil="true"/>
  <melting-point>-56°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>5.64 mg/mL at 30°C</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Endogenous, Ingestion, Dermal (contact)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Uremic toxins such as hexanal 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 nil="true"/>
  <lethaldose nil="true"/>
  <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 nil="true"/>
  <health-effects>Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.</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>
  <created-at type="dateTime">2014-08-29T05:50:30Z</created-at>
  <updated-at type="dateTime">2026-04-17T18:17:30Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C02373</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>121338</chebi-id>
  <biocyc-id>4-METHYLPENTANAL</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCCCCC=O</moldb-smiles>
  <moldb-formula>C6H12O</moldb-formula>
  <moldb-inchi>InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3</moldb-inchi>
  <moldb-inchikey>JARKCYVAAOWBJS-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">100.1589</moldb-average-mass>
  <moldb-mono-mass type="decimal">100.088815006</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Liquid</state>
  <logp>1.78</logp>
  <hmdb-id>HMDB05994</hmdb-id>
  <chembl-id>CHEMBL280331</chembl-id>
  <chemspider-id>5949</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>Hershberg, E. B.  Aldehyde synthesis.    Helvetica Chimica Acta  (1934),  17  351-8.  CODEN: HCACAV  ISSN:0018-019X.  CAN 28:28437  AN 1934:28437  </synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003141</chemdb-id>
  <dsstox-id>DTXSID2021604</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00009211</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>17.07</moldb-polar-surface-area>
  <moldb-refractivity>30.148199999999996</moldb-refractivity>
  <moldb-polarizability>12.32467328566576</moldb-polarizability>
  <moldb-rotatable-bond-count>4</moldb-rotatable-bond-count>
  <moldb-acceptor-count>1</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic>17.788839028560098</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-6.944305972130752</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>2.37</moldb-alogps-logp>
  <moldb-alogps-logs>-1.35</moldb-alogps-logs>
  <moldb-alogps-solubility>4.49e+00 g/l</moldb-alogps-solubility>
</compound>
