Basic Info

Common Name2-Nonenal(F05271)
2D Structure
Description

2-Nonenal 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.
2-Nonenal is found in alcoholic beverages. 2-Nonenal is widespread in nature, in beer, coffee, watermelon, cucumbers, redcurrants, orris oil, palm oil, potatoes etc. 2-Nonenal is a flavouring ingredient. 2-Nonenal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms.

FRCD IDF05271
CAS Number2463-53-8
PubChem CID5354833
FormulaC9H16O
IUPAC Name

(Z)-non-2-enal

InChI Key

BSAIUMLZVGUGKX-FPLPWBNLSA-N

InChI

InChI=1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7-

Canonical SMILES

CCCCCCC=CC=O

Isomeric SMILES

CCCCCC/C=C\C=O

Wikipedia2-Nonenal
Synonyms
        
            cis-2-Nonenal
        
            3-Hexyl-2-propenal
        
            (Z)-Non-2-enal
        
            (Z)-2-nonenal
        
            2-Nonenal, (Z)-
        
            2-Nonenal, (2Z)-
        
            UNII-ARM1W3309Z
        
            Non-2-enal
        
            2-Nonen-1-al
        
            ARM1W3309Z
        
Classifies
                

                  
                    Predicted: Veterinary Drug
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree NodesAldehydes
Direct ParentMedium-chain aldehydes
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsMedium-chain aldehyde - Enal - Alpha,beta-unsaturated aldehyde - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight140.226
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count6
Complexity94.9
Monoisotopic Mass140.12
Exact Mass140.12
XLogP3.1
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9837
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.8589
P-glycoprotein SubstrateNon-substrate0.6362
P-glycoprotein InhibitorNon-inhibitor0.8612
Non-inhibitor0.6085
Renal Organic Cation TransporterNon-inhibitor0.8834
Distribution
Subcellular localizationPlasma membrane0.5260
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7894
CYP450 2D6 SubstrateNon-substrate0.8567
CYP450 3A4 SubstrateNon-substrate0.7325
CYP450 1A2 InhibitorInhibitor0.7244
CYP450 2C9 InhibitorNon-inhibitor0.9285
CYP450 2D6 InhibitorNon-inhibitor0.9653
CYP450 2C19 InhibitorNon-inhibitor0.9519
CYP450 3A4 InhibitorNon-inhibitor0.9911
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7617
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7909
Non-inhibitor0.8947
AMES ToxicityNon AMES toxic0.9446
CarcinogensCarcinogens 0.5691
Fish ToxicityHigh FHMT0.9797
Tetrahymena Pyriformis ToxicityHigh TPT0.9999
Honey Bee ToxicityHigh HBT0.7513
BiodegradationReady biodegradable0.6163
Acute Oral ToxicityIII0.8135
Carcinogenicity (Three-class)Non-required0.6467

Model Value Unit
Absorption
Aqueous solubility-3.1892LogS
Caco-2 Permeability1.4002LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5307LD50, mol/kg
Fish Toxicity-0.9070pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.7259pIGC50, ug/L

References

TitleJournalDatePubmed ID
S-metolachlor promotes oxidative stress in green microalga Parachlorella kessleri - A potential environmental and health risk for higher organisms.Sci Total Environ2018 Oct 129751315
Prooxidant effect of α-tocopherol on soybean oil. Global monitoring of its oxidation process under accelerated storage conditions by <sup>1</sup>H nuclear magnetic resonance.Food Chem2018 Apr 1529287377
Volatile molecular markers of VOO Thermo-oxidation: Effect of heating processes, macronutrients composition, and olive ripeness on the new emitted aldehydic compounds.Food Res Int2018 Apr29579972
Lipidomic analysis for carbonyl species derived from fish oil using liquid chromatography-tandem mass spectrometry.Talanta2017 Jun 128391860
Astaxanthin ameliorates ferric nitrilotriacetate-induced renal oxidative injury in rats.J Clin Biochem Nutr2017 Jul28751805
Simultaneous Analysis of Malondialdehyde, 4-Hydroxy-2-hexenal, and 4-Hydroxy-2-nonenal in Vegetable Oil by Reversed-Phase High-Performance Liquid Chromatography.J Agric Food Chem2017 Dec 2729179555
Aldehyde Oxidase 4 Plays a Critical Role in Delaying Silique Senescence by Catalyzing Aldehyde Detoxification.Plant Physiol2017 Apr28188272
Development of an LC-MS/MS analytical method for the simultaneous measurement of aldehydes from polyunsaturated fatty acids degradation in animal feed.Drug Test Anal2016 May27443200
Extrapancreatic effects of incretin hormones: evidence for weight-independent changes in morphological aspects and oxidative status in insulin-sensitive organs of the obese nondiabetic Zucker rat (ZFR).Physiol Rep2016 Aug27511983
Effect of Selected Volatiles on Two Stored Pests: The Fungus Fusarium verticillioides and the Maize Weevil Sithophilus zeamais.J Agric Food Chem2015 Sep 926257042
L-carnitine supplementation as a potential antioxidant therapy for inherited neurometabolic disorders.Gene2014 Jan 1024148561
Nitrite curing of chicken, pork, and beef inhibits oxidation but does not affect N-nitroso compound (NOC)-specific DNA adduct formation during in vitro digestion.J Agric Food Chem2014 Feb 2624499368
Novel molecular approaches for improving enzymatic and nonenzymatic detoxification of 4-hydroxynonenal: toward the discovery of a novel class of bioactive compounds.Free Radic Biol Med2014 Apr24456906
Fate in digestion in vitro of several food components, including some toxic compounds coming from omega-3 and omega-6 lipids.Food Chem Toxicol2011 Jan20937346
Aldose reductase protects against early atherosclerotic lesion formation in apolipoprotein E-null mice.Circ Res2009 Oct 919729598
Supplementary catechins attenuate cooking-oil-fumes-induced oxidative stress in rat lung.Chin J Physiol2009 Jun 3019777801
Use of an in vitro digestion model to study the bioaccessibility of 4-hydroxy-2-nonenal and related aldehydes present in oxidized oils rich in omega-6 acyl groups.J Agric Food Chem2008 Sep 2418729379
Toxic oxygenated alpha,beta-unsaturated aldehydes and their study in foods: a review.Crit Rev Food Sci Nutr2008 Feb18274968
The cytotoxic and genotoxic effects of conjugated trans-2-nonenal (T2N), an off-flavor compound in beer and heat processed food arising from lipid oxidation.Pol J Microbiol200516457380
CYP3A induction aggravates endotoxemic liver injury via reactive oxygen species in male rats.Free Radic Biol Med2004 Sep 115288127

Targets

General Function:
Vitamin d binding
Specific Function:
May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
Gene Name:
KL
Uniprot ID:
Q9UEF7
Molecular Weight:
116179.815 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Superoxide-generating nadph oxidase activity
Specific Function:
Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
Gene Name:
NOX4
Uniprot ID:
Q9NPH5
Molecular Weight:
66930.995 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]