Nonanal (CHEM003152)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-08-29 05:51:36 UTC
Update Date2026-04-16 22:35:40 UTC
Accession NumberCHEM003152
Identification
Common NameNonanal
ClassSmall Molecule
DescriptionNonanal 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. Nonanal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aldehyde
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Uremic Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-NonaldehydeChEBI
Nonanoic aldehydeChEBI
Nonyl aldehydeChEBI
NonylaldehydeChEBI
Nonylic aldehydeChEBI
PelargonaldehydeChEBI
Pelargonic aldehydeChEBI
N-NonylaldehydeHMDB
NonanalMeSH
Chemical FormulaC9H18O
Average Molecular Mass142.239 g/mol
Monoisotopic Mass142.136 g/mol
CAS Registry Number124-19-6
IUPAC Namenonanal
Traditional Namenonanal
SMILESCCCCCCCCC=O
InChI IdentifierInChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h9H,2-8H2,1H3
InChI KeyGYHFUZHODSMOHU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentMedium-chain aldehydes
Alternative Parents
Substituents
  • Medium-chain aldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP3.81ALOGPS
logP2.99ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)17.79ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.95 m³·mol⁻¹ChemAxon
Polarizability18.54 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-7bfee629e196af9e810aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-7a91b8574f3d51d4856aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-373d544eb5629e680bc4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-858f5f7c138a343dc472Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-6653261e95803e235236Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-7bfee629e196af9e810aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-7a91b8574f3d51d4856aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-373d544eb5629e680bc4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-858f5f7c138a343dc472Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-6653261e95803e235236Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-062l-9000000000-b8472e31e5bcec84f30cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-f0ef344b71801c87bae2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9700000000-6646461d0ed7f00c9732Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-e9cf39f812a5e37b3253Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-f0a7779f3ceded55079fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-8a94df0d859760c12b51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-c476311d08e1bd1d53dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-31a4c0b614cfbc7c3156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-fc1333865a778fe31452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3e15d73ab7b0a83b0b4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-9000000000-15622cc20ddbb14ed88cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-bacbd1e7d4f6be160b21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-796b68d98dc297622b77Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-945f6bb4a733637d5cf8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureEndogenous, Ingestion, Dermal (contact)
Mechanism of ToxicityUremic 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) (2). 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 (3).
MetabolismUremic 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.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNaturally produced by the body (endogenous).
Minimum Risk LevelNot Available
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
SymptomsAs 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.
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0059835
FooDB IDFDB003303
Phenol Explorer IDNot Available
KNApSAcK IDC00030828
BiGG IDNot Available
BioCyc IDCPD-8491
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNonanal
Chemspider ID29029
ChEBI ID84268
PubChem Compound ID31289
Kegg Compound IDNot Available
YMDB IDYMDB16054
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=25172748
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25466114
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25518943
4. Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77.
5. Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009
6. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24.