Gene Association: SELENOP
UniProt Search:
SELENOP (PROTEIN_CODING)
Function Description: selenoprotein P
found 28 associated metabolites with current gene based on the text mining result from the pubmed database.
Se-Methylselenocysteine
Se-Methylselenocysteine (SeMSC) is a naturally occurring seleno-amino acid that is synthesized by plants such as garlic, astragalus, onions, and broccoli. It cannot be synthesized by higher animals. Unlike selenomethionine, which is incorporated into proteins in place of methionine, SeMSC is not incorporated into any proteins, thereby being fully available for the synthesis of selenium-containing enzymes such as glutathione peroxidase. Selenomethionine is the major seleno-compound in cereal grains (wheat grain, maize, and rice), soybeans, and enriched yeast. Seleno-compounds present in plants may have a profound effect upon the health of animals and human subjects. It is now known that the total Se content cannot be used as an indication of its efficacy, but knowledge of individual selenocompounds is necessary to fully assess the significance. Thus, speciation of the seleno-compounds has moved to the forefront. Since animals and man are dependent upon plants for their nutritional requirements, this makes the types of seleno-compounds in plants even more critical. Se enters the food chain through incorporation into plant proteins, mostly as selenocysteine and selenomethionine at normal Se levels. There are two possible pathways for the catabolism of selenomethionine: (1) a transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded to H2Se by the enzyme beta-lyase and (2) a transamination-decarboxylation pathway. It was estimated that 90\\\\% of methionine is metabolized through this pathway and thus could be also the major route for selenomethionine catabolism (PMID: 14748935 , Br J Nutr. 2004 Jan;91(1):11-28.). Selenomethionine is an amino acid containing selenium. The L-isomer of selenomethionine, known as Se-met and Sem, is a common natural food source of selenium. In vivo, selenomethionine is randomly incorporated instead of methionine and is readily oxidized. Its antioxidant activity arises from its ability to deplete reactive species. Selenium and sulfur are chalcogen elements that share many chemical properties and the substitution of methionine to selenomethionine may have no effect on protein structure and function. However, the incorporation of selenomethionine into tissue proteins and keratin in horses causes alkali disease. Alkali disease is characterized by emaciation, loss of hair, deformation and shedding of hooves, loss of vitality, and erosion of the joints of long bones. Se-methyl-L-selenocysteine is an L-alpha-amino acid compound having methylselanylmethyl as the side-chain. It has a role as an antineoplastic agent. It is a Se-methylselenocysteine, a non-proteinogenic L-alpha-amino acid and a L-selenocysteine derivative. It is a conjugate base of a Se-methyl-L-selenocysteinium. It is a conjugate acid of a Se-methyl-L-selenocysteinate. It is an enantiomer of a Se-methyl-D-selenocysteine. It is a tautomer of a Se-methyl-L-selenocysteine zwitterion. Methylselenocysteine has been used in trials studying the prevention of Prostate Carcinoma and No Evidence of Disease. Se-Methylselenocysteine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Methylselenocysteine is a naturally occurring organoselenium compound found in many plants, including garlic, onions, and broccoli, with potential antioxidant and chemopreventive activities. Se-Methyl-seleno-L-cysteine (MSC) is an amino acid analogue of cysteine in which a methylselenium moiety replaces the sulphur atom of cysteine. This agent acts as an antioxidant when incorporated into glutathione peroxidase and has been shown to exhibit potent chemopreventive activity in animal models. Se-Methylselenocysteine (SeMSC) is a naturally occurring seleno-amino acid that is synthesized by plants such as garlic, astragalus, onions and broccoli. Unlike selenomethionine, which is incorporated into proteins in place of methionine, SeMSC is not incorporated into any proteins, thereby being fully available for the synthesis of selenium-containing enzymes such as glutathione peroxidase. 3-(Methylseleno)alanine is found in many foods, some of which are common cabbage, white cabbage, lima bean, and cauliflower. D020011 - Protective Agents > D016588 - Anticarcinogenic Agents C26170 - Protective Agent > C275 - Antioxidant D000970 - Antineoplastic Agents Se-Methylselenocysteine, a precursor of Methylselenol, has potent cancer chemopreventive activity and anti-oxidant activity. Se-Methylselenocysteine is orally bioavailable, and induces apoptosis[1][2]. Se-Methylselenocysteine, a precursor of Methylselenol, has potent cancer chemopreventive activity and anti-oxidant activity. Se-Methylselenocysteine is orally bioavailable, and induces apoptosis[1][2].
Selenomethionine
L-selenomethionine is the L-enantiomer of selenomethionine. It is an enantiomer of a D-selenomethionine. It is a tautomer of a L-selenomethionine zwitterion. Selenomethionine is a naturally occuring amino acid in some plant materials such as cereal grains, soybeans and enriched yeast but it cannot be synthesized from animals or humans. It can be produced from post-structural modifications. *In vivo*, selenomethionine plays an essential role in acting as an antioxidant, where it depletes reactive oxygen species (ROS) and aids in the formation and recycling of glutathione, another important antioxidant. In comparison to selenite, which is the inorganic form of selenium, the organic form of selenomethionine is more readily absorbed in the human body. Selenomethionin is used in biochemical laboratories where its incorporation into proteins that need to be visualized enhances the performance of X-ray crystallography. L-Selenomethionine is the amino acid methionine with selenium substituting for the sulphur moiety. Methionine is an essential amino acid in humans, whereas selenium is a free-radical scavenging anti-oxidant, essential for the protection of various tissues from the damages of lipid peroxidation. As a trace mineral that is toxic in high doses, selenium is a cofactor for glutathione peroxidase, an anti-oxidant enzyme that neutralizes hydrogen peroxide. L-Selenomethionine is considered a safe, efficacious form of selenium and is readily bioavailable. Selenium may be chemoprotective for certain cancers, particularly prostate cancer. (NCI04) Diagnostic aid in pancreas function determination. Selenomethionine (CAS: 1464-42-2) is an amino acid containing selenium that cannot be synthesized by higher animals but can be obtained from plant material. Selenomethionine is the major seleno-compound in cereal grains (wheat grain, maize, and rice), soybeans, and enriched yeast. Seleno-compounds present in plants may have a profound effect on the health of animals and human subjects. It is now known that the total Se content cannot be used as an indication of its efficacy, but knowledge of individual selenocompounds is necessary to fully assess the significance. Thus, speciation of the seleno-compounds has moved to the forefront. Since animals and man are dependent upon plants for their nutritional requirements, this makes the types of seleno-compounds in plants even more critical. Se enters the food chain through incorporation into plant proteins, mostly as selenocysteine and selenomethionine at normal Se levels. There are two possible pathways for the catabolism of selenomethionine. One is the transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded into H2Se by the enzyme beta-lyase. The other pathway is the transamination-decarboxylation pathway. It was estimated that 90\\\\% of methionine is metabolized through this pathway and thus could be also the major route for selenomethionine catabolism (PMID:14748935). Found in onion, cabbage, coco de mono (Lecythis elliptica), Brazil nuts (Bertholletia excelsa), wheat grains and other plants. Dietary supplement for avoidance of Se deficiency in humans and ruminants C26170 - Protective Agent > C275 - Antioxidant The L-enantiomer of selenomethionine. L-SelenoMethionine, an L-isomer of Selenomethionine, is a major natural food-form of selenium. L-SelenoMethionin is a cancer chemopreventive agent that can reduce cancer incidence by dietary supplementation and induce apoptosis of cancer cells. L-SelenoMethionine also can increase expression of glutathione peroxidase[1][2][3]. Selenomethionine is a naturally occurring amino acid containing selenium and is a common natural food source.
Epoxiconazole
D016573 - Agrochemicals D010575 - Pesticides CONFIDENCE standard compound; INTERNAL_ID 238; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9422; ORIGINAL_PRECURSOR_SCAN_NO 9420 CONFIDENCE standard compound; INTERNAL_ID 238; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9436; ORIGINAL_PRECURSOR_SCAN_NO 9433 CONFIDENCE standard compound; INTERNAL_ID 238; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9461; ORIGINAL_PRECURSOR_SCAN_NO 9459 CONFIDENCE standard compound; INTERNAL_ID 238; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9474; ORIGINAL_PRECURSOR_SCAN_NO 9472 CONFIDENCE standard compound; INTERNAL_ID 238; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9445; ORIGINAL_PRECURSOR_SCAN_NO 9444 CONFIDENCE standard compound; INTERNAL_ID 238; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9488; ORIGINAL_PRECURSOR_SCAN_NO 9486 CONFIDENCE standard compound; INTERNAL_ID 2574 CONFIDENCE standard compound; INTERNAL_ID 8407 CONFIDENCE standard compound; EAWAG_UCHEM_ID 95
Methionine sulfoxide
Methionine sulfoxide belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Methionine sulfoxide exists in all living species, ranging from bacteria to humans. Within humans, methionine sulfoxide participates in a number of enzymatic reactions. In particular, methionine sulfoxide can be biosynthesized from L-methionine through its interaction with the enzyme methionine-R-sulfoxide reductase B3. In addition, methionine sulfoxide can be biosynthesized from L-methionine through the action of the enzyme methionine-R-sulfoxide reductase b2, mitochondrial. In humans, methionine sulfoxide is involved in the metabolic disorder called hypermethioninemia. Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species via 2-electron-dependent mechanism. Such oxidants can be generated from activated neutrophils; therefore, methionine sulfoxide can be regarded as a biomarker of oxidative stress in vivo. (PMID 12576054) [HMDB]. Methionine sulfoxide is found in many foods, some of which are romaine lettuce, white cabbage, dill, and yellow bell pepper. L-Methionine sulfoxide (H-Met(O)-OH), a metabolite of Methionine, induces M1/classical macrophage polarization, and modulates oxidative stress and purinergic signaling parameters[1]. Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo. Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo.
12(S)-HPETE
12-HPETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Leukotrienes). Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (+/-)12-HETE. A family of biologically active compounds derived from arachidonic acid by oxidative metabolism through the 5-lipoxygenase pathway. They participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. They have potent actions on many essential organs and systems, including the cardiovascular, pulmonary, and central nervous system as well as the gastrointestinal tract and the immune system. 12-HPETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Leukotrienes). Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (+/-)12-HETE. D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents
alpha-Tocopherol acetate
D020011 - Protective Agents > D000975 - Antioxidants > D024505 - Tocopherols Vitamin E supplement and antioxidant for foodstuffs Vitamin E supplement and antioxidant for foodstuff D018977 - Micronutrients > D014815 - Vitamins Same as: D01735 D-α-Tocopherol acetate (D-Vitamin E acetate) can be hydrolyzed to d-alpha-tocopherol (VE) and absorbed in the small intestine[1]. D-α-Tocopherol acetate (D-Vitamin E acetate) can be hydrolyzed to d-alpha-tocopherol (VE) and absorbed in the small intestine[1].
Mercury
D - Dermatologicals > D08 - Antiseptics and disinfectants > D08A - Antiseptics and disinfectants > D08AK - Mercurial products Mercury is a metal that is a liquid at room temperature. Mercury has a long and interesting history deriving from its use in medicine and industry, with the resultant toxicity produced. In high enough doses, all forms of mercury can produce toxicity. The most devastating tragedies related to mercury toxicity in recent history include Minamata Bay and Niagata, Japan in the 1950s, and Iraq in the 1970s. More recent mercury toxicity issues include the extreme toxicity of the dimethylmercury compound noted in 1998, the possible toxicity related to dental amalgams, and the disproved relationship between vaccines and autism related to the presence of the mercury-containing preservative, thimerosal.; Hair has been used in many studies as a bioindicator of mercury exposure for human populations. At the time of hair formation, mercury from the blood capillaries penetrates into the hair follicles. As hair grows approximately 1 cm each month, mercury exposure over time is recapitulated in hair strands. Mercury levels in hair closest to the scalp reflect the most recent exposure, while those farthest from the scalp are representative of previous blood concentrations. Sequential analyses of hair mercury have been useful for identifying seasonal variations over time in hair mercury content, which may be the result of seasonal differences in bioavailability of fish and differential consumption of piscivorous and herbivorous fish species. Knowledge of the relation between fish-eating practices and hair mercury levels is particularly important for adequate mitigation strategies. Physiologically, it exists as an ion in the body. Methyl mercury is well absorbed, and because the biological half-life is long, the body burden in humans may reach high levels. People who frequently eat contaminated seafood can acquire mercury concentrations that are potentially dangerous to the fetus in pregnant women. The dose-response relationships have been extensively studied, and the safe levels of exposure have tended to decline. Individual methyl mercury exposure is usually determined by analysis of mercury in blood and hair. ; Whilst the clinical features of acute mercury poisoning have been well described, chronic low dose exposure to mercury remains poorly characterised and its potential role in various chronic disease states remains controversial. Low molecular weight thiols, i.e. sulfhydryl containing molecules such as cysteine, are emerging as important factors in the transport and distribution of mercury throughout the body due to the phenomenon of "Molecular Mimicry" and its role in the molecular transport of mercury. Chelation agents such as the dithiols sodium 2,3-dimercaptopropanesulfate (DMPS) and meso-2,3-dimercaptosuccinic acid (DMSA) are the treatments of choice for mercury toxicity. Alpha-lipoic acid (ALA), a disulfide, and its metabolite dihydrolipoic acid (DHLA), a dithiol, have also been shown to have chelation properties when used in an appropriate manner. Whilst N-acetyl-cysteine (NAC) and glutathione (GSH) have been recommended in the treatment of mercury toxicity in the past, an examination of available evidence suggests these agents may in fact be counterproductive. Zinc and selenium have also been shown to exert protective effects against mercury toxicity, most likely mediated by induction of the metal binding proteins metallothionein and selenoprotein-P. Evidence suggests however that the co-administration of selenium and dithiol chelation agents during treatment may also be counter-productive. Finally, the issue of diagnostic testing for chronic, historical or low dose mercury poisoning is considered including an analysis of the influence of ligand interactions and nutritional factors upon the accuracy of "chelation challenge" tests. (PMID: 17448359, 17408840, 17193738). Mercury is found in many foods, some of which are rice, wild carrot, horseradish, and endive.
Iodine
Elemental iodine (I2) is poisonous if taken orally in larger amounts; 2?3 grams of it is a lethal dose for an adult human.; Elemental iodine is an oxidizing irritant and direct contact with skin can cause lesions, so iodine crystals should be handled with care. Solutions with high elemental iodine concentration such as tincture of iodine are capable of causing tissue damage if use for cleaning and antisepsis is prolonged.; In many ways, 129I is similar to 36Cl. It is a soluble halogen, fairly non-reactive, exists mainly as a non-sorbing anion, and is produced by cosmogenic, thermonuclear, and in-situ reactions. In hydrologic studies, 129I concentrations are usually reported as the ratio of 129I to total I (which is virtually all 127I). As is the case with 36Cl/Cl, 129I/I ratios in nature are quite small, 10?14 to 10?10 (peak thermonuclear 129I/I during the 1960s and 1970s reached about 10?7). 129I differs from 36Cl in that its halflife is longer (15.7 vs. 0.301 million years), it is highly biophilic, and occurs in multiple ionic forms (commonly, I? and IO3?) which have different chemical behaviors. This makes it fairly easy for 129I to enter the biosphere as it becomes incorporated into vegetation, soil, milk, animal tissue, etc.; Iodic acid (HIO3) and its salts are strong oxidizers. Periodic acid (HIO4) cleaves vicinal diols along the C-C bond to give aldehyde fragments. 2-Iodoxybenzoic acid and Dess-Martin periodinane are hypervalent iodine oxidants used to specifically oxidize alcohols to ketones or aldehydes. Iodine pentoxide is a strong oxidant as well.; Iodine (pronounced /?a?.?da?n/ EYE-o-dyne, /?a?.?d?n/ EYE-o-d?n, or in chemistry /?a?.?di?n/ EYE-o-deen; from Greek: ????? iodes "violet"), is a chemical element that has the symbol I and atomic number 53. Naturally-occurring iodine is a single isotope with 74 neutrons. Chemically, iodine is the second least reactive of the halogens, and the second most electropositive halogen, trailing behind astatine in both of these categories. However, the element does not occur in the free state in nature. As with all other halogens (members of Group 17 in the periodic table), when freed from its compounds iodine forms diatomic molecules (I2).; Iodine forms many compounds. Potassium iodide is the most commercially significant iodine compound. It is a convenient source of the iodide anion; it is easier to handle than sodium iodide because it is not hygroscopic. Sodium iodide is especially useful in the Finkelstein reaction, because it is soluble in acetone, while potassium iodide is poorly so. In this reaction, an alkyl chloride is converted to an alkyl iodide. This relies on the insolubility of sodium chloride in acetone to drive the reaction:; Iodine is a common general stain used in thin-layer chromatography. It is also used in the Gram stain as a mordant, after the sample is treated with crystal violet.; Iodine is an essential trace element for life, the heaviest element commonly needed by living organisms, and the second-heaviest known to be used by any form of life (only tungsten, a component of a few bacterial enzymes, has a higher atomic number and atomic weight). Iodines main role in animal biology is as constituents of the thyroid hormones, thyroxine (T4) and triiodothyronine (T3). These are made from addition condensation products of the amino acid tyrosine, and are stored prior to release in an iodine-containing protein called thyroglobulin. T4 and T3 contain four and three atoms of iodine per molecule, respectively. The thyroid gland actively absorbs iodide from the blood to make and release these hormones into the blood, actions which are regulated by a second hormone TSH from the pituitary. Thyroid hormones are phylogenetically very old molecules which are synthesized by most multicellular organisms, and which even have some effect on unicellular organisms.; Iodine is an essential trace element. Chemically, iodine is the least reactive of the halogens, and the most ele... Iodine is an essential trace element. Chemically, iodine is the least reactive of the halogens, and the most electropositive halogen after astatine. However, iodine does not occur in the free state in nature. As with all other halogens , when freed from its compounds iodine forms diatomic molecules (I2). Iodine and its compounds are primarily used in medicine, photography, and dyes. Iodine is required for the production of thyroid hormones, which are essential for normal brain development, and the fetus, newborn, and young child are particularly vulnerable to iodine deficiency. Physiologically, iodine exists as an ion in the body. The iodine requirement increases during pregnancy and recommended intakes are in the range of 220-250 microg/day. Monitoring iodine status during pregnancy is a challenge. New recommendations from World Health Organization suggest that a median urinary iodine concentration >250 microg/L and <500 microg/L indicates adequate iodine intake in pregnancy. Based on this range, it appears that many pregnant women in have inadequate intakes. Thyroid-stimulating hormone concentration in the newborn is a sensitive indicator of mild iodine deficiency in late pregnancy. The potential adverse effects of mild iodine deficiency during pregnancy are uncertain. Controlled trials of iodine supplementation in mildly iodine-deficient pregnant women suggest beneficial effects on maternal and newborn serum thyroglobulin and thyroid volume, but no effects on maternal and newborn total or free thyroid hormone concentrations. There are no long-term data on the effect of iodine supplementation on birth outcomes or infant development. New data from well-controlled studies indicate that iodine repletion in moderately iodine-deficient school-age children has clear benefits: it improves cognitive and motor function; it also increases concentrations of insulin-like growth factor 1 and insulin-like growth factor-binding protein 3, and improves somatic growth. (PMID: 17956157). D - Dermatologicals > D08 - Antiseptics and disinfectants > D08A - Antiseptics and disinfectants > D08AG - Iodine products D018977 - Micronutrients > D014131 - Trace Elements D000890 - Anti-Infective Agents
Hydrogen selenide
Hydrogen selenide is a metabolite of selenium which could have potential antiangiogenic effect in the chemoprevention of cancer. The hydrogen selenide is a key intermediate in the selenium methylation metabolism of inorganic and organic selenium compounds. Accumulation of the hydrogen selenide resulting from inhibition of the selenium methylation metabolism, detoxification metabolic pathway of selenium, is found in animals following repeated administration of a toxic dose of selenocystine. The excess of the hydrogen selenide produced by inhibition of the selenium methylation metabolism contributes to the hepatotoxicity caused by selenocystine. (PMID: 9414580, 11799926) [HMDB] Hydrogen selenide is a metabolite of selenium which could have potential antiangiogenic effect in the chemoprevention of cancer. The hydrogen selenide is a key intermediate in the selenium methylation metabolism of inorganic and organic selenium compounds. Accumulation of the hydrogen selenide resulting from inhibition of the selenium methylation metabolism, detoxification metabolic pathway of selenium, is found in animals following repeated administration of a toxic dose of selenocystine. The excess of the hydrogen selenide produced by inhibition of the selenium methylation metabolism contributes to the hepatotoxicity caused by selenocystine. (PMID: 9414580, 11799926).
Selenium
Selenium-dependent enzymes and selenoprotein P regulate immune and endothelial cell function. (PMID: 16607122). Thyroid hormone synthesis, metabolism and action require adequate availability of the essential trace elements iodine and selenium, which affect homeostasis of thyroid hormone-dependent metabolic pathways. The three selenocysteine-containing iodothyronine deiodinases constitute a novel gene family. Selenium is retained and deiodinase expression is maintained at almost normal levels in the thyroid gland, the brain and several other endocrine tissues during selenium deficiency, thus guaranteeing adequate local and systemic levels of the active thyroid hormone T(3). (PMID: 16131327). The trace element nutrient selenium (Se) discharges its well-known nutritional antioxidant activity through the Se-dependent glutathione peroxidases. It also regulates nuclear factor activities by redox mechanisms through the selenoprotein thioredoxin reductases. Converging data from epidemiological, ecological, and clinical studies have shown that Se can decrease the risk for some types of human cancers, especially those of the prostate, lung, and colon. Mechanistic studies have indicated that the methylselenol metabolite pool has many desirable attributes of chemoprevention, targeting both cancer cells and vascular endothelial cells, whereas the hydrogen selenide pool in excess of selenoprotein synthesis can lead to DNA single strand breaks, which may be mediated by some reactive oxygen species. (PMID: 16356132). SePP (selenoprotein P) is the major transporter of Se in the serum. Moreover, in the sanctuary area of the brain, SePP was shown to play a hitherto unexpected role as a local Se storage and recycling protein that directly maintains brain Se levels. Physiologically, it exists as an ion in the body. The function of Se is important in normal brain metabolism, redox regulation, antioxidant defenses, thyroid hormone metabolism and the development of neurodegenerative conditions. (PMID: 15720294). In areas where soils are low in bioavailable selenium (Se), potential Se deficiencies cause health risks for humans. (PMID: 16028492) Dietary selenium comes from cereals, meat, fish, and eggs. The recommended dietary allowance for adults is 55 micrograms per day. D020011 - Protective Agents > D000975 - Antioxidants D018977 - Micronutrients > D014131 - Trace Elements Essential dietary component
Gamma-Glutamyl-Se-methylselenocysteine
gamma-Glutamyl-Se-methylselenocysteine is an intermediate in selenoamino acid metabolism(KEGG ID C05695). It is generated from Se-methyl-selenocysteine via the enzyme gamma-glutamyltranspeptidase [EC:2.3.2.2]. [HMDB] gamma-Glutamyl-Se-methylselenocysteine is an intermediate in selenoamino acid metabolism(KEGG ID C05695). It is generated from Se-methyl-selenocysteine via the enzyme gamma-glutamyltranspeptidase [EC:2.3.2.2].
Selenocystine
Selenocystine, also known as 3,3-diselenodialanine, belongs to the class of organic compounds known as alpha-amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxyl group (alpha carbon). More specifically, selenocystine is a diselenide consisting of two selenoamino acids that are attached together at their selenium atoms. This particular selenoamino acid is selenocysteine, the selenium analogue to cysteine (selenium being the element directly beneath sulphur in the periodic table); likewise, selenocystine is the selenium analogue to cystine. Since each constituent amino acid has a stereocentre, there are three different stereoisomers of selenocystine: D-selenocystine, L-selenocystine, and meso-selenocystine, the first two of which are optically active. Like other amino acids, L-selenocystine is the most common form within organisms; however, the D- and meso- forms have also been found (PMID: 30920149). Selenocystine is a solid that is moderately soluble in water. Due to the reactivity of selenocysteine, it is rarely encountered; rather, cells store selenium in the less reactive oxidized form of selenocystine or in a methylated form, such as selenomethionine (DOI: 10.1007/978-3-319-92405-2_3). When cells are grown in the absence of selenium, translation of selenoproteins terminates at the UGA codon, resulting in a truncated, non-functional enzyme. Unlike other amino acids present in biological proteins, selenocysteine is not coded for directly in the genetic code. Rather, the tRNA-bound seryl residue is converted to a selenocysteine residue by the pyridoxal phosphate-containing enzyme selenocysteine synthase (PMID: 17194211). Kurt Franke et al. indicated that there was evidence that selenium was in a form similar to that of cysteine, predating Thressa Stadtman’s discovery of the 21st amino acid by four decades (PMID: 26949981; J. Biol. Chem. 111:643). Selenocysteine may be denoted by the short forms Sec, U, or SeCys (Cys is used for cysteine), whereas selenocystine may be denoted by SeCys2. However, the literature sometimes uses SeCys for selenocystine and may cause confusion. Selenocystine has been found in animals, plants, and bacteria. It is being researched as treatment for cancer and for its antioxidant properties (PMID: 24763048, 24030774). Selenium, in its various forms such as selenocystine, is essential for many species, including humans, yet it is also toxic to all organisms; hence, it has come to be referred to as the “essential poison” (PMID: 26949981; 6679541). Selenocystine is a substrate for glutathione peroxidase 1. [HMDB] D000890 - Anti-Infective Agents > D000998 - Antiviral Agents L-Selenocystine is a diselenide-bridged amino acid. L-Selenocystine is a redox-active selenium compound that has both anti- and pro-oxidant actions. L-Selenocystine induces an unfolded protein response, ER stress, and large cytoplasmic vacuolization in HeLa cells and has cytostatic effects in a range of cancer cell types[1].
15(S)-HPETE
15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983). D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
methylselenocysteine
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents Se-Methylselenocysteine, a precursor of Methylselenol, has potent cancer chemopreventive activity and anti-oxidant activity. Se-Methylselenocysteine is orally bioavailable, and induces apoptosis[1][2]. Se-Methylselenocysteine, a precursor of Methylselenol, has potent cancer chemopreventive activity and anti-oxidant activity. Se-Methylselenocysteine is orally bioavailable, and induces apoptosis[1][2].
Methionine sulfoxide
MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QEFRNWWLZKMPFJ-UHFFFAOYSA-N_STSL_0131_Methionine sulfoxide_2000fmol_180425_S2_LC02_MS02_81; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.050 L-Methionine sulfoxide (H-Met(O)-OH), a metabolite of Methionine, induces M1/classical macrophage polarization, and modulates oxidative stress and purinergic signaling parameters[1]. Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo. Methionine sulfoxide is an oxidation product of methionine with reactive oxygen species and can be regarded as a biomarker of oxidative stress in vivo.
Selenomethionine
A selenoamino acid that is the selenium analogue of methionine. C26170 - Protective Agent > C275 - Antioxidant Selenomethionine, also known as (2s)-2-amino-4-(methylseleno)butanoate or 2-amino-4-(methylselenyl)butyric acid, is a member of the class of compounds known as alpha amino acids. Alpha amino acids are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Selenomethionine is soluble (in water) and a moderately acidic compound (based on its pKa). Selenomethionine can be found in a number of food items such as shiitake, canada blueberry, sesbania flower, and spearmint, which makes selenomethionine a potential biomarker for the consumption of these food products. Selenomethionine can be found primarily in blood and urine, as well as throughout most human tissues. Selenomethionine exists in all eukaryotes, ranging from yeast to humans. In humans, selenomethionine is involved in the selenoamino acid metabolism. Moreover, selenomethionine is found to be associated with prostate cancer. Selenomethionine is a naturally occurring amino acid. The L-selenomethionine enantiomer is the main form of selenium found in Brazil nuts, cereal grains, soybeans, and grassland legumes, while Se-methylselenocysteine, or its γ-glutamyl derivative, is the major form of selenium found in Astragalus, Allium, and Brassica species. In vivo, selenomethionine is randomly incorporated instead of methionine. Selenomethionine is readily oxidized . L-SelenoMethionine, an L-isomer of Selenomethionine, is a major natural food-form of selenium. L-SelenoMethionin is a cancer chemopreventive agent that can reduce cancer incidence by dietary supplementation and induce apoptosis of cancer cells. L-SelenoMethionine also can increase expression of glutathione peroxidase[1][2][3]. Selenomethionine is a naturally occurring amino acid containing selenium and is a common natural food source.
H-Met(O)-OH
L-Methionine sulfoxide (H-Met(O)-OH), a metabolite of Methionine, induces M1/classical macrophage polarization, and modulates oxidative stress and purinergic signaling parameters[1].
Selenocystine
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
15(S)-HPETE
D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents D004791 - Enzyme Inhibitors > D016859 - Lipoxygenase Inhibitors D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides The (S)-enantiomer of 15-HPETE. 15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HPETE) is the corresponding hydroperoxide of 15(S)-HETE and undergoes homolytic decomposition to the DNA-reactive bifunctional electrophile 4-oxo-2(E)-nonenal, a precursor of heptanone-etheno-2-deoxyguanosine. Reactive oxygen species convert the omega-6 polyunsaturated fatty acid arachidonic acid into (15-HPETE); vitamin C mediates 15(S)-HPETE decomposition. 15(S)-HPETE initiates apoptosis in vascular smooth muscle cells. 15(S)-HPETE is a lipoxygenase metabolite that affects the expression of cell adhesion molecules (CAMs) involved in the adhesion of leukocytes and/or the accumulation of leukocytes in the vascular endothelium, these being the initial events in endothelial cell injury. 15(S)-HPETE induces a loss of cardiomyocytes membrane integrity. 15-(S)HPETE is a hydroperoxide that enhances the activity of the enzymes lipoxygenase [EC 1.13.11.12] and Na+, K+-ATPase [EC 3.6.3.9] of brain microvessels. Lipoxygenase(s) and Na+-K+-ATPase of brain microvessels may play a significant role in the occurrence of ischemic brain edema. (PMID: 15964853, 15723435, 8655602, 8595608, 2662983) [HMDB]
12(S)-HPETE
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents The (S)-enantiomer of 12-HPETE.
Tocopheryl acetate
D020011 - Protective Agents > D000975 - Antioxidants > D024505 - Tocopherols D018977 - Micronutrients > D014815 - Vitamins
gamma-Glutamyl-Se-methylselenocysteine
A dipeptide obtained by formal condensation of the gamma-carboxy group of glutamic acid with the amino group of Se-methylselenocysteine.
