Malondialdehyde
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Basic Info
Common Name | Malondialdehyde(F05266) |
2D Structure | |
Description | Malondialdehyde 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 | F05266 |
CAS Number | 542-78-9 |
PubChem CID | 10964 |
Formula | C3H4O2 |
IUPAC Name | propanedial |
InChI Key | WSMYVTOQOOLQHP-UHFFFAOYSA-N |
InChI | InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2 |
Canonical SMILES | C(C=O)C=O |
Isomeric SMILES | C(C=O)C=O |
Wikipedia | Malondialdehyde |
Synonyms | MALONALDEHYDE Malondialdehyde Propanedial Malonyldialdehyde Malonodialdehyde Malonic aldehyde Malonic dialdehyde 1,3-Propanedial 1,3-Propanedione 1,3-Propanedialdehyde |
Classifies | Pollutant |
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 | Not available |
Direct Parent | 1,3-dicarbonyl compounds |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | 1,3-dicarbonyl compound - Alpha-hydrogen aldehyde - Organic oxide - Hydrocarbon derivative - Short-chain aldehyde - Aldehyde - Aliphatic acyclic compound |
Description | This compound belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 72.063 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 2 |
Rotatable Bond Count | 2 |
Complexity | 34.2 |
Monoisotopic Mass | 72.021 |
Exact Mass | 72.021 |
XLogP | -0.6 |
Formal Charge | 0 |
Heavy Atom Count | 5 |
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+ | 0.9901 |
Human Intestinal Absorption | HIA+ | 0.9782 |
Caco-2 Permeability | Caco2+ | 0.6417 |
P-glycoprotein Substrate | Non-substrate | 0.8763 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9257 |
Non-inhibitor | 0.9667 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9194 |
Distribution | ||
Subcellular localization | Mitochondria | 0.7033 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8634 |
CYP450 2D6 Substrate | Non-substrate | 0.9106 |
CYP450 3A4 Substrate | Non-substrate | 0.8195 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8284 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9214 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9408 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9036 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9459 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9419 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9095 |
Non-inhibitor | 0.9859 | |
AMES Toxicity | AMES toxic | 0.8718 |
Carcinogens | Carcinogens | 0.6596 |
Fish Toxicity | Low FHMT | 0.6921 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9172 |
Honey Bee Toxicity | High HBT | 0.7399 |
Biodegradation | Ready biodegradable | 0.8375 |
Acute Oral Toxicity | III | 0.8280 |
Carcinogenicity (Three-class) | Non-required | 0.6912 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | 0.5002 | LogS |
Caco-2 Permeability | 1.1959 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.2325 | LD50, mol/kg |
Fish Toxicity | 0.3121 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.1500 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Effects of aged ZnO NPs and soil type on Zn availability, accumulation and toxicity to pea and beet in a greenhouse experiment. | Ecotoxicol Environ Saf | 2018 Sep 30 | 29807295 |
The protective effects of DL-Selenomethionine against T-2/HT-2 toxins-induced cytotoxicity and oxidative stress in broiler hepatocytes. | Toxicol In Vitro | 2018 Sep 25 | 30261313 |
Adducts formed during protein digestion decreased the toxicity of five carbonyl compounds against Caco-2 cells. | J Hazard Mater | 2018 Sep 24 | 30300775 |
Dietary supplementation of Yucca schidigera extract enhances productive and reproductive performances, blood profile, immune function, and antioxidant status in laying Japanese quails exposed to lead in the diet. | Poult Sci | 2018 Sep 1 | 29846703 |
Kolaviron attenuates diclofenac-induced nephrotoxicity in male Wistar rats. | Appl Physiol Nutr Metab | 2018 Sep | 29847737 |
Protective effects of compound ammonium glycyrrhizin, L‑arginine, silymarin and glucurolactone against liver damage induced by ochratoxin A in primary chicken hepatocytes. | Mol Med Rep | 2018 Sep | 30015927 |
Fumonisin B<sub>1</sub> exposure increases Hsp70 expression in the lung and kidney of rats without inducing significant oxidative stress. | Acta Vet Hung | 2018 Sep | 30264617 |
Protective Effect of N-Acetylcysteine against Oxidative Stress Induced by Zearalenone via Mitochondrial Apoptosis Pathway in SIEC02 Cells. | Toxins (Basel) | 2018 Oct 9 | 30304829 |
Dose-related impacts of imidacloprid oral intoxication on brain and liver of rock pigeon (Columba livia domestica), residues analysis in different organs. | Ecotoxicol Environ Saf | 2018 Oct 5 | 30296697 |
l-arginine protects against oxidative damage induced by T-2 toxin in mouse Leydig cells. | J Biochem Mol Toxicol | 2018 Oct | 30091165 |
Biochemical and histological alterations in adult zebrafish(Danio rerio)ovary following exposure to the tetronic acid insecticide spirotetramat. | Ecotoxicol Environ Saf | 2018 Nov 30 | 30107324 |
Influence of sex on biomarkers of oxidative stress in the kidney, lungs, and liver of rabbits after exposure to diazinon. | Environ Sci Pollut Res Int | 2018 Nov | 30232776 |
Selective effects of fenitrothion on murine splenic T-lymphocyte populations and cytokine/granzyme production. | J Environ Sci Health B | 2018 May 4 | 29431569 |
Effect of CuSO4 and nano copper on serum antioxidant capacity in Weaned piglets. | J Biol Regul Homeost Agents | 2018 Mar-Apr | 29684999 |
SlMYC2 Involved in Methyl Jasmonate-Induced Tomato Fruit Chilling Tolerance. | J Agric Food Chem | 2018 Mar 28 | 29528226 |
Chronic exposure to high fat diet exacerbates arsenic-induced lung damages inmale mice: Possible role for oxidative stress. | Monaldi Arch Chest Dis | 2018 Mar 23 | 29741077 |
d-Fagomine Attenuates High Glucose-Induced Endothelial Cell Oxidative Damage byUpregulating the Expression of PGC-1α. | J Agric Food Chem | 2018 Mar 21 | 29489344 |
Long-Term Excessive Selenium Supplementation Induces Hypertension in Rats. | Biol Trace Elem Res | 2018 Mar | 28634813 |
Hepatoprotective and free radical scavenging actions of quercetin nanoparticles on aflatoxin B1-induced liver damage: in vitro/in vivo studies. | Artif Cells Nanomed Biotechnol | 2018 Mar | 28423950 |
Methionine hydroxy analogue supplementation modulates gill immunological andbarrier health status of grass carp (Ctenopharyngodon idella). | Fish Shellfish Immunol | 2018 Mar | 29360541 |
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 ]