Hexanal
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Basic Info
| Common Name | Hexanal(F05265) |
| 2D Structure | |
| Description | Hexanal 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 | F05265 |
| CAS Number | 66-25-1 |
| PubChem CID | 6184 |
| Formula | C6H12O |
| IUPAC Name | hexanal |
| InChI Key | JARKCYVAAOWBJS-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3 |
| Canonical SMILES | CCCCCC=O |
| Isomeric SMILES | CCCCCC=O |
| Synonyms |
Hexaldehyde
Capronaldehyde
n-Hexanal
Caproic aldehyde
HEXANAL
Caproaldehyde
66-25-1
1-Hexanal
Hexanaldehyde
n-Caproaldehyde
|
| Classifies |
Predicted: Pesticide
|
| 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 - Alpha-hydrogen 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 | 100.161 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 4 |
| Complexity | 41.4 |
| Monoisotopic Mass | 100.089 |
| Exact Mass | 100.089 |
| XLogP | 1.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9886 |
| Human Intestinal Absorption | HIA+ | 0.9945 |
| Caco-2 Permeability | Caco2+ | 0.8535 |
| P-glycoprotein Substrate | Non-substrate | 0.6530 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8996 |
| Non-inhibitor | 0.9489 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8984 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.3488 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8068 |
| CYP450 2D6 Substrate | Non-substrate | 0.8607 |
| CYP450 3A4 Substrate | Non-substrate | 0.7224 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7073 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9407 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9600 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9544 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9882 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8874 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8603 |
| Non-inhibitor | 0.8629 | |
| AMES Toxicity | Non AMES toxic | 0.9807 |
| Carcinogens | Carcinogens | 0.5980 |
| Fish Toxicity | High FHMT | 0.7424 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9404 |
| Honey Bee Toxicity | High HBT | 0.6951 |
| Biodegradation | Ready biodegradable | 0.7723 |
| Acute Oral Toxicity | III | 0.8676 |
| Carcinogenicity (Three-class) | Non-required | 0.7099 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.3628 | LogS |
| Caco-2 Permeability | 1.5061 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.4364 | LD50, mol/kg |
| Fish Toxicity | 1.0542 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.0449 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Relationship between the Physiochemical Properties of Cocoa Procyanidins andTheir Ability to Inhibit Lipid Oxidation in Liposomes. | J Agric Food Chem | 2018 May 2 | 29649362 |
| Gas Chromatography-Mass Spectrometry-Olfactometry To Control the AromaFingerprint of Extra Virgin Olive Oil from Three Tunisian Cultivars at ThreeHarvest Times. | J Agric Food Chem | 2018 Mar 21 | 29485281 |
| Extra virgin olive oil aroma release after interaction with human saliva fromindividuals with different body mass index. | J Sci Food Agric | 2018 Jul | 29277918 |
| Stability and Antioxidant Activity of Annatto (Bixa orellana L.) TocotrienolsDuring Frying and in Fried Tortilla Chips. | J Food Sci | 2018 Feb | 29337368 |
| 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 |
| Volatile and key odourant compounds of Turkish Berberis crataegina fruit usingGC-MS-Olfactometry. | Nat Prod Res | 2018 Apr | 28764557 |
| Characterization of the Key Aroma Compounds in Five Varieties of Mandarins by GasChromatography-Olfactometry, Odor Activity Values, Aroma Recombination, andOmission Analysis. | J Agric Food Chem | 2017 Sep 27 | 28885016 |
| Prenatal and Early Postnatal Odorant Exposure Heightens Odor-Evoked Mitral CellResponses in the Mouse Olfactory Bulb. | eNeuro | 2017 Sep 26 | 28955723 |
| Triticale crisp bread enriched with selected bioactive additives: volatileprofile, physical characteristics, sensory and nutritional properties. | J Food Sci Technol | 2017 Sep | 28974794 |
| Characteristic Flavor of Traditional Soup Made by Stewing Chinese Yellow-Feather Chickens. | J Food Sci | 2017 Sep | 28732107 |
| Consumer acceptance and aroma characterization of navy bean (Phaseolus vulgaris) powders prepared by extrusion and conventional processing methods. | J Sci Food Agric | 2017 Sep | 28230271 |
| Effects of Different Lipophilized Ferulate Esters in Fish Oil-Enriched Milk:Partitioning, Interaction, Protein, and Lipid Oxidation. | J Agric Food Chem | 2017 Nov 1 | 29048172 |
| Hexanal as biomarker for milk oxidative stress induced by copper ions. | J Dairy Sci | 2017 Mar | 28088419 |
| Acceptability and Preference Drivers of Freshly Roasted Peanuts. | J Food Sci | 2017 Jan | 27886380 |
| Changes in volatile profile of soybean residue (okara) upon solid-statefermentation by yeasts. | J Sci Food Agric | 2017 Jan | 26940283 |
| Metabolome based volatiles profiling in 13 date palm fruit varieties from Egyptvia SPME GC-MS and chemometrics. | Food Chem | 2017 Feb 15 | 27664623 |
| Effect of natural antioxidants in Spanish salchichón elaborated with encapsulatedn-3 long chain fatty acids in konjac glucomannan matrix. | Meat Sci | 2017 Feb | 27835835 |
| Natural Occurrence of Aldol Condensation Products in Valencia Orange Oil. | J Food Sci | 2017 Dec | 29095499 |
| Static headspace analysis of odorants in commercial rice proteins. | Food Chem | 2017 Apr 15 | 27979212 |
| Peach skin powder inhibits oxidation in cooked turkey meat. | Poult Sci | 2016 Oct 1 | 27252372 |
Targets
- General Function:
- Aldehyde dehydrogenase [nad(p)+] activity
- Specific Function:
- Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
- Gene Name:
- ALDH3B1
- Uniprot ID:
- P43353
- Molecular Weight:
- 51839.245 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:
- 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 ]