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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:42:01 UTC
Update Date2019-07-23 21:42:05 UTC
HMDB IDHMDB0031269
Secondary Accession Numbers
  • HMDB31269
Metabolite Identification
Common Name2-Nonenal
Description2-Nonenal, also known as 3-hexyl-acrolein or non-2-enal, 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. Uremic toxins such as 2-Nonenall are actively transported into the kidneys via organic ion transporters (especially OAT3). 2-Nonenal is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Nonenal is a cucumber, fatty, and green tasting compound. Outside of the human body, 2-Nonenal has been detected, but not quantified in, several different foods, such as asparagus, carrots, corns, and lemons. This could make 2-nonenal a potential biomarker for the consumption of these foods. 2-Nonenal is a potentially toxic compound. 2-Nonenal, with regard to humans, has been found to be associated with the diseases such as uremia; 2-nonenal has also been linked to the inborn metabolic disorder celiac disease. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. 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). Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. As a uremic toxin, this compound can cause uremic syndrome. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma.
Structure
Data?1563862103
Synonyms
ValueSource
2-Nonen-1-alHMDB
2-Nonenal (acd/name 4.0)HMDB
3-Hexyl-2-propenalHMDB
3-Hexyl-acroleinHMDB
3-HexylacroleinHMDB
alpha-Nonenyl aldehydeHMDB
beta-HexylacroleinHMDB
HeptylideneacetaldehydeHMDB
Non-2-enalHMDB
2(e)-NonenalHMDB
2-Nonenal, (trans)-isomerHMDB
2-Nonenal, (cis)-isomerHMDB
cis-2-NonenalHMDB
trans-2-NonenalHMDB
2-NonenalMeSH
Chemical FormulaC9H16O
Average Molecular Weight140.2227
Monoisotopic Molecular Weight140.120115134
IUPAC Name(2Z)-non-2-enal
Traditional Name(2Z)-non-2-enal
CAS Registry Number2463-53-8
SMILES
CCCCCC\C=C/C=O
InChI Identifier
InChI=1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7-
InChI KeyBSAIUMLZVGUGKX-FPLPWBNLSA-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
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.093 g/LALOGPS
logP3.56ALOGPS
logP2.98ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability17.47 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0693-9100000000-fe986a33ebee50d94c74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-d743ce7dbe98059caa97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9600000000-fac276d62d90751c0504Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-74804619dd37ef95e2dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-bac8cbc4ed9a3b5f5c63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-31e9e8394ef8b17eeb1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-b2d9978875d508fa9f65Spectrum
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-2d339566c8edf566c309Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.13 +/- 0.04 uMAdult (>18 years old)BothNormal details
FecesDetected and Quantified0-26481.685 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)BothNormal
    • Zhang, S., Liu, L...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.73 +/- 0.42 uMAdult (>18 years old)Bothuremia details
FecesDetected and Quantified0-121616.0674 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Uremia
  1. 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. [PubMed:22626821 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003311
KNApSAcK IDC00029331
Chemspider ID4510945
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Nonenal
METLIN IDNot Available
PubChem Compound5354833
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:22626821 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .