2-Hexenal
(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-Hexenal(F05273) |
| 2D Structure | |
| Description | 2-Hexenal 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 | F05273 |
| CAS Number | 505-57-7 |
| PubChem CID | 5281168 |
| Formula | C6H10O |
| IUPAC Name | (E)-hex-2-enal |
| InChI Key | MBDOYVRWFFCFHM-SNAWJCMRSA-N |
| InChI | InChI=1S/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+ |
| Canonical SMILES | CCCC=CC=O |
| Isomeric SMILES | CCC/C=C/C=O |
| Synonyms |
2-HEXENAL
2-trans-Hexenal
trans-2-Hexenal
6728-26-3
Leaf aldehyde
(E)-Hex-2-enal
(E)-2-HEXENAL
beta-Propyl acrolein
Hexylenic aldehyde
Hex-2-en-1-al
|
| 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 | 98.145 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 3 |
| Complexity | 64.6 |
| Monoisotopic Mass | 98.073 |
| Exact Mass | 98.073 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| 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+ | 0.9841 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8724 |
| P-glycoprotein Substrate | Non-substrate | 0.7359 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8924 |
| Non-inhibitor | 0.7919 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9161 |
| Distribution | ||
| Subcellular localization | Plasma membrane | 0.5310 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7750 |
| CYP450 2D6 Substrate | Non-substrate | 0.8938 |
| CYP450 3A4 Substrate | Non-substrate | 0.7550 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5082 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9367 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9683 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9323 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9866 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7803 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8519 |
| Non-inhibitor | 0.9681 | |
| AMES Toxicity | AMES toxic | 0.8776 |
| Carcinogens | Carcinogens | 0.6556 |
| Fish Toxicity | High FHMT | 0.8062 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9978 |
| Honey Bee Toxicity | High HBT | 0.7876 |
| Biodegradation | Ready biodegradable | 0.7241 |
| Acute Oral Toxicity | III | 0.8626 |
| Carcinogenicity (Three-class) | Non-required | 0.5505 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.8383 | LogS |
| Caco-2 Permeability | 1.7619 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0294 | LD50, mol/kg |
| Fish Toxicity | 0.3400 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.0169 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| 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 |
| Exploring a volatomic-based strategy for a fingerprinting approach of Vacciniumpadifolium L. berries at different ripening stages. | Food Chem | 2018 Apr 15 | 29287355 |
| 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 |
| Nematicidal Activity of trans-2-Hexenal against Southern Root-Knot Nematode(Meloidogyne incognita) on Tomato Plants. | J Agric Food Chem | 2017 Jan 25 | 28048941 |
| 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 |
| Evaluation of the synergism among volatile compounds in Oolong tea infusion byodour threshold with sensory analysis and E-nose. | Food Chem | 2017 Apr 15 | 27979119 |
| 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 |
| Characterization of the Key Aroma Volatile Compounds in Cranberry (Vacciniummacrocarpon Ait.) Using Gas Chromatography-Olfactometry (GC-O) and Odor Activity Value (OAV). | J Agric Food Chem | 2016 Jun 22 | 27265519 |
| The Changes in Color, Soluble Sugars, Organic Acids, Anthocyanins and AromaComponents in "Starkrimson" during the Ripening Period in China. | Molecules | 2016 Jun 22 | 27338331 |
| 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 |
| Nematicidal Activity of the Volatilome of Eruca sativa on Meloidogyne incognita. | J Agric Food Chem | 2015 Jul 15 | 26082278 |
| Chemical and sensory comparison of fresh and dried lulo (Solanum quitoense Lam.) fruit aroma. | Food Chem | 2015 Feb 15 | 25236202 |
| A physiologically based in silico model for trans-2-hexenal detoxification andDNA adduct formation in human including interindividual variation indicatesefficient detoxification and a negligible genotoxicity risk. | Arch Toxicol | 2013 Sep | 23864024 |
| Flavor of cold-hardy grapes: impact of berry maturity and environmentalconditions. | J Agric Food Chem | 2013 Nov 6 | 24151907 |
| The omega-3 fatty acid eicosapentaenoic acid accelerates disease progression in a model of amyotrophic lateral sclerosis. | PLoS One | 2013 | 23620776 |
| Effects of aliphatic aldehydes on the growth and patulin production of Penicillium expansum in apple juice. | Biosci Biotechnol Biochem | 2013 | 23291770 |
| Functional characterization of SlscADH1, a fruit-ripening-associated short-chain alcohol dehydrogenase of tomato. | J Plant Physiol | 2012 Oct 15 | 22818888 |
| Contribution of ALDH1A1 isozyme to detoxification of aldehydes present in food products. | Acta Pol Pharm | 2012 Nov-Dec | 23285706 |
| Electrophysiological and behavioral activity of (E)-2-hexenal in the granaryweevil and its application in food packaging. | J Food Prot | 2012 Feb | 22289599 |
Targets
- General Function:
- S-nitrosoglutathione binding
- Specific Function:
- Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.
- Gene Name:
- GSTP1
- Uniprot ID:
- P09211
- Molecular Weight:
- 23355.625 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:
- 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:
- 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 ]