2-Nonenal
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
Common Name | 2-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. |
FRCD ID | F05271 |
CAS Number | 2463-53-8 |
PubChem CID | 5354833 |
Formula | C9H16O |
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 |
Wikipedia | 2-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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic oxygen compounds |
Class | Organooxygen compounds |
Subclass | Carbonyl compounds |
Intermediate Tree Nodes | Aldehydes |
Direct Parent | Medium-chain aldehydes |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Medium-chain aldehyde - Enal - Alpha,beta-unsaturated aldehyde - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 140.226 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 1 |
Rotatable Bond Count | 6 |
Complexity | 94.9 |
Monoisotopic Mass | 140.12 |
Exact Mass | 140.12 |
XLogP | 3.1 |
Formal Charge | 0 |
Heavy Atom Count | 10 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 1 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9837 |
Human Intestinal Absorption | HIA+ | 1.0000 |
Caco-2 Permeability | Caco2+ | 0.8589 |
P-glycoprotein Substrate | Non-substrate | 0.6362 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.8612 |
Non-inhibitor | 0.6085 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8834 |
Distribution | ||
Subcellular localization | Plasma membrane | 0.5260 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7894 |
CYP450 2D6 Substrate | Non-substrate | 0.8567 |
CYP450 3A4 Substrate | Non-substrate | 0.7325 |
CYP450 1A2 Inhibitor | Inhibitor | 0.7244 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9285 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9653 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9519 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9911 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7617 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7909 |
Non-inhibitor | 0.8947 | |
AMES Toxicity | Non AMES toxic | 0.9446 |
Carcinogens | Carcinogens | 0.5691 |
Fish Toxicity | High FHMT | 0.9797 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9999 |
Honey Bee Toxicity | High HBT | 0.7513 |
Biodegradation | Ready biodegradable | 0.6163 |
Acute Oral Toxicity | III | 0.8135 |
Carcinogenicity (Three-class) | Non-required | 0.6467 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.1892 | LogS |
Caco-2 Permeability | 1.4002 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.5307 | LD50, mol/kg |
Fish Toxicity | -0.9070 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 1.7259 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
S-metolachlor promotes oxidative stress in green microalga Parachlorella kessleri - A potential environmental and health risk for higher organisms. | Sci Total Environ | 2018 Oct 1 | 29751315 |
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 Chem | 2018 Apr 15 | 29287377 |
Volatile molecular markers of VOO Thermo-oxidation: Effect of heating processes, macronutrients composition, and olive ripeness on the new emitted aldehydic compounds. | Food Res Int | 2018 Apr | 29579972 |
Lipidomic analysis for carbonyl species derived from fish oil using liquid chromatography-tandem mass spectrometry. | Talanta | 2017 Jun 1 | 28391860 |
Astaxanthin ameliorates ferric nitrilotriacetate-induced renal oxidative injury in rats. | J Clin Biochem Nutr | 2017 Jul | 28751805 |
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 Chem | 2017 Dec 27 | 29179555 |
Aldehyde Oxidase 4 Plays a Critical Role in Delaying Silique Senescence by Catalyzing Aldehyde Detoxification. | Plant Physiol | 2017 Apr | 28188272 |
Development of an LC-MS/MS analytical method for the simultaneous measurement of aldehydes from polyunsaturated fatty acids degradation in animal feed. | Drug Test Anal | 2016 May | 27443200 |
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 Rep | 2016 Aug | 27511983 |
Effect of Selected Volatiles on Two Stored Pests: The Fungus Fusarium verticillioides and the Maize Weevil Sithophilus zeamais. | J Agric Food Chem | 2015 Sep 9 | 26257042 |
L-carnitine supplementation as a potential antioxidant therapy for inherited neurometabolic disorders. | Gene | 2014 Jan 10 | 24148561 |
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 Chem | 2014 Feb 26 | 24499368 |
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 Med | 2014 Apr | 24456906 |
Fate in digestion in vitro of several food components, including some toxic compounds coming from omega-3 and omega-6 lipids. | Food Chem Toxicol | 2011 Jan | 20937346 |
Aldose reductase protects against early atherosclerotic lesion formation in apolipoprotein E-null mice. | Circ Res | 2009 Oct 9 | 19729598 |
Supplementary catechins attenuate cooking-oil-fumes-induced oxidative stress in rat lung. | Chin J Physiol | 2009 Jun 30 | 19777801 |
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 Chem | 2008 Sep 24 | 18729379 |
Toxic oxygenated alpha,beta-unsaturated aldehydes and their study in foods: a review. | Crit Rev Food Sci Nutr | 2008 Feb | 18274968 |
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 Microbiol | 2005 | 16457380 |
CYP3A induction aggravates endotoxemic liver injury via reactive oxygen species in male rats. | Free Radic Biol Med | 2004 Sep 1 | 15288127 |
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
- 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
- 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
- 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 ]