4-Hydroxynonenal
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Basic Info
Common Name | 4-Hydroxynonenal(F05264) |
2D Structure | |
Description | 4-Hydroxynonenal 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 | F05264 |
CAS Number | 75899-68-2 |
PubChem CID | 5283344 |
Formula | C9H16O2 |
IUPAC Name | (E)-4-hydroxynon-2-enal |
InChI Key | JVJFIQYAHPMBBX-FNORWQNLSA-N |
InChI | InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+ |
Canonical SMILES | CCCCCC(C=CC=O)O |
Isomeric SMILES | CCCCCC(/C=C/C=O)O |
Wikipedia | 4-Hydroxynonenal |
Synonyms | 4-Hydroxynonenal 4-Hydroxy-2-nonenal 4-hydroxynon-2-enal trans-4-Hydroxy-2-nonenal 4-Hydroxy-2,3-nonenal 4-HNE 75899-68-2 4-hydroxy-2E-nonenal CCRIS 1781 CCRIS 9028 |
Classifies | Predicted: Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Lipids and lipid-like molecules |
Class | Fatty Acyls |
Subclass | Fatty alcohols |
Intermediate Tree Nodes | Not available |
Direct Parent | Fatty alcohols |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Fatty alcohol - Medium-chain aldehyde - Enal - Alpha,beta-unsaturated aldehyde - Secondary alcohol - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aldehyde - Alcohol - Aliphatic acyclic compound |
Description | This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 156.225 |
Hydrogen Bond Donor Count | 1 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 6 |
Complexity | 119 |
Monoisotopic Mass | 156.115 |
Exact Mass | 156.115 |
XLogP | 1.7 |
Formal Charge | 0 |
Heavy Atom Count | 11 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 1 |
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+ | 0.9645 |
Human Intestinal Absorption | HIA+ | 1.0000 |
Caco-2 Permeability | Caco2+ | 0.8443 |
P-glycoprotein Substrate | Non-substrate | 0.5346 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.8646 |
Non-inhibitor | 0.7963 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9160 |
Distribution | ||
Subcellular localization | Mitochondria | 0.4963 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7618 |
CYP450 2D6 Substrate | Non-substrate | 0.8791 |
CYP450 3A4 Substrate | Non-substrate | 0.6148 |
CYP450 1A2 Inhibitor | Inhibitor | 0.8630 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9157 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9243 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8966 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9176 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8044 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8903 |
Non-inhibitor | 0.8474 | |
AMES Toxicity | Non AMES toxic | 0.9132 |
Carcinogens | Non-carcinogens | 0.5856 |
Fish Toxicity | High FHMT | 0.7889 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9936 |
Honey Bee Toxicity | High HBT | 0.7273 |
Biodegradation | Ready biodegradable | 0.8948 |
Acute Oral Toxicity | III | 0.5880 |
Carcinogenicity (Three-class) | Non-required | 0.6755 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -1.7576 | LogS |
Caco-2 Permeability | 1.5953 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.9009 | LD50, mol/kg |
Fish Toxicity | 1.6408 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.3124 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Alleviation of Cardiac Damage by Dietary Fenugreek (Trigonella foenum-graecum)Seeds is Potentiated by Onion (Allium cepa) in Experimental Diabetic Rats viaBlocking Renin-Angiotensin System. | Cardiovasc Toxicol | 2018 Jun | 29094243 |
Hemistepsin A ameliorates acute inflammation in macrophages via inhibition of nuclear factor-κB and activation of nuclear factor erythroid 2-related factor 2. | Food Chem Toxicol | 2018 Jan | 29129664 |
Morphological alterations induced by the exposure to TiO<sub>2</sub> nanoparticles in primary cortical neuron cultures and in the brain of rats. | Toxicol Rep | 2018 | 30175048 |
Stevia and stevioside protect against cisplatin nephrotoxicity through inhibitionof ERK1/2, STAT3, and NF-κB activation. | Food Chem Toxicol | 2017 Sep | 28666887 |
Immunofluorescence evaluation of 4-hydroxynonenal and 8-hydroxy-2-deoxyguanosine activation in zebrafish (Daino rerio) larvae brain exposed (microinjected) topropyl gallate. | Chemosphere | 2017 Sep | 28550782 |
Differential Effects of Low- and High-dose Zinc Supplementation on SynapticPlasticity and Neurogenesis in the Hippocampus of Control and High-fat Diet-fedMice. | Neurochem Res | 2017 Nov | 28770438 |
Zinc Prevents the Development of Diabetic Cardiomyopathy in db/db Mice. | Int J Mol Sci | 2017 Mar 7 | 28272348 |
Attenuation of oxidative stress and cardioprotective effects of zincsupplementation in experimental diabetic rats. | Br J Nutr | 2017 Feb | 28245884 |
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 |
The Role of Mitochondrial Aldehyde Dehydrogenase 2 (ALDH2) in Neuropathology and Neurodegeneration. | Acta Neurol Taiwan | 2016 Dec 15 | 28382610 |
Solanum torvum Swartz. fruit attenuates cadmium-induced liver and kidney damagethrough modulation of oxidative stress and glycosylation. | Environ Sci Pollut Res Int | 2016 Apr | 26762936 |
A central role for heme iron in colon carcinogenesis associated with red meat intake. | Cancer Res | 2015 Mar 1 | 25592152 |
Dietary polyunsaturated fatty acids and heme iron induce oxidative stress biomarkers and a cancer promoting environment in the colon of rats. | Free Radic Biol Med | 2015 Jun | 25744414 |
Deterioration of plasticity and metabolic homeostasis in the brain of theUCD-T2DM rat model of naturally occurring type-2 diabetes. | Biochim Biophys Acta | 2014 Sep | 24840661 |
Neuroprotective effects of Z-ajoene, an organosulfur compound derived fromoil-macerated garlic, in the gerbil hippocampal CA1 region after transientforebrain ischemia. | Food Chem Toxicol | 2014 Oct | 24997311 |
Lipid peroxidation end product 4-hydroxy-trans-2-nonenal triggers unfoldedprotein response and heme oxygenase-1 expression in PC12 cells: Roles of ROS and MAPK pathways. | Toxicology | 2014 Jan 6 | 24291486 |
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 |
Diet high in fructose leads to an overexpression of lipocalin-2 in rat fattyliver. | World J Gastroenterol | 2014 Feb 21 | 24587658 |
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 |
Resveratrol protects SR-B1 levels in keratinocytes exposed to cigarette smoke. | Free Radic Biol Med | 2014 Apr | 24423486 |
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:
- Electron carrier activity
- Gene Name:
- ALDH2
- Uniprot ID:
- P05091
- Molecular Weight:
- 56380.93 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:
- Transcription factor activity, sequence-specific dna binding
- Specific Function:
- Multifunctional enzyme that, as well as its role in glycolysis, plays a part in various processes such as growth control, hypoxia tolerance and allergic responses. May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons. Stimulates immunoglobulin production.MBP1 binds to the myc promoter and acts as a transcriptional repressor. May be a tumor suppressor.
- Gene Name:
- ENO1
- Uniprot ID:
- P06733
- Molecular Weight:
- 47168.555 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:
- Phospholipid transporter activity
- Specific Function:
- Participates in the reverse transport of cholesterol from tissues to the liver for excretion by promoting cholesterol efflux from tissues and by acting as a cofactor for the lecithin cholesterol acyltransferase (LCAT). As part of the SPAP complex, activates spermatozoa motility.
- Gene Name:
- APOA1
- Uniprot ID:
- P02647
- Molecular Weight:
- 30777.58 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:
- 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:
- Zinc ion binding
- Specific Function:
- NAD-dependent protein deacetylase. Activates or deactivates mitochondrial target proteins by deacetylating key lysine residues. Known targets include ACSS1, IDH, GDH, SOD2, PDHA1, LCAD, SDHA and the ATP synthase subunit ATP5O. Contributes to the regulation of the cellular energy metabolism. Important for regulating tissue-specific ATP levels.
- Gene Name:
- SIRT3
- Uniprot ID:
- Q9NTG7
- Molecular Weight:
- 43572.71 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:
- Virus receptor activity
- Specific Function:
- Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma membrane, called caveolae. Facilitates the flux of free and esterified cholesterol between the cell surface and extracellular donors and acceptors, such as HDL and to a lesser extent, apoB-containing lipoproteins and modified lipoproteins. Probably involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity. Receptor for hepatitis C virus glycoprotein E2. Binding between SCARB1 and E2 was found to be independent of the genotype of the viral isolate. Plays an important role in the uptake of HDL cholesteryl ester (By similarity).(Microbial infection) Acts as a receptor for hepatitis C virus in hepatocytes.
- Gene Name:
- SCARB1
- Uniprot ID:
- Q8WTV0
- Molecular Weight:
- 60877.385 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 dismutase activity
- Specific Function:
- Destroys superoxide anion radicals which are normally produced within the cells and which are toxic to biological systems.
- Gene Name:
- SOD2
- Uniprot ID:
- P04179
- Molecular Weight:
- 24721.955 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:
- Ubiquitin protein ligase binding
- Gene Name:
- TPI1
- Uniprot ID:
- P60174
- Molecular Weight:
- 30790.785 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:
- Transmembrane transporter activity
- Specific Function:
- Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Subunits alpha and beta form the catalytic core in F(1). Rotation of the central stalk against the surrounding alpha(3)beta(3) subunits leads to hydrolysis of ATP in three separate catalytic sites on the beta subunits. Subunit alpha does not bear the catalytic high-affinity ATP-binding sites (By similarity).
- Gene Name:
- ATP5A1
- Uniprot ID:
- P25705
- Molecular Weight:
- 59750.06 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:
- Dihydropyrimidinase activity
- Specific Function:
- Plays a role in neuronal development and polarity, as well as in axon growth and guidance, neuronal growth cone collapse and cell migration. Necessary for signaling by class 3 semaphorins and subsequent remodeling of the cytoskeleton. May play a role in endocytosis.
- Gene Name:
- DPYSL2
- Uniprot ID:
- Q16555
- Molecular Weight:
- 62293.135 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:
- Transporter activity
- Specific Function:
- Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
- Gene Name:
- ABCC1
- Uniprot ID:
- P33527
- Molecular Weight:
- 171589.5 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:
- Phosphothreonine binding
- Specific Function:
- Peptidyl-prolyl cis/trans isomerase (PPIase) that binds to and isomerizes specific phosphorylated Ser/Thr-Pro (pSer/Thr-Pro) motifs in a subset of proteins, resulting in conformational changes in the proteins (PubMed:21497122, PubMed:22033920). Displays a preference for an acidic residue N-terminal to the isomerized proline bond. Regulates mitosis presumably by interacting with NIMA and attenuating its mitosis-promoting activity. Down-regulates kinase activity of BTK (PubMed:16644721). Can transactivate multiple oncogenes and induce centrosome amplification, chromosome instability and cell transformation. Required for the efficient dephosphorylation and recycling of RAF1 after mitogen activation (PubMed:15664191). Binds and targets PML and BCL6 for degradation in a phosphorylation-dependent manner (PubMed:17828269). Acts as a regulator of JNK cascade by binding to phosphorylated FBXW7, disrupting FBXW7 dimerization and promoting FBXW7 autoubiquitination and degradation: degradation of FBXW7 leads to subsequent stabilization of JUN (PubMed:22608923).
- Gene Name:
- PIN1
- Uniprot ID:
- Q13526
- Molecular Weight:
- 18243.13 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 ]