Classification Term: 170407

Abrine

C12H14N2O2 (218.1055)

N(alpha)-methyl-L-tryptophan is a N-methyl-L-alpha-amino acid that is the N(alpha)-methyl derivative of L-tryptophan. It has a role as an Escherichia coli metabolite. It is a L-tryptophan derivative and a N-methyl-L-alpha-amino acid. It is a tautomer of a N(alpha)-methyl-L-tryptophan zwitterion. N-Methyltryptophan is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). A N-methyl-L-alpha-amino acid that is the N(alpha)-methyl derivative of L-tryptophan. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.216 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.210 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.211 L-(+)-Abrine, a lethal albumin found in Abrus precatorius seeds, is an acute toxic alkaloid and chemical marker for abrin. L-(+)-Abrine, a lethal albumin found in Abrus precatorius seeds, is an acute toxic alkaloid and chemical marker for abrin.

L-Tyrosine

C9H11NO3 (181.0739)

Tyrosine (Tyr) or L-tyrosine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-tyrosine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tyrosine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tyrosine is a non-essential amino acid, meaning the body can synthesize it – usually from phenylalanine. The conversion of phenylalanine to tyrosine is catalyzed by the enzyme phenylalanine hydroxylase, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of phenylalanine, such that it becomes tyrosine. Tyrosine is found in many high-protein food products such as chicken, turkey, fish, milk, yogurt, cottage cheese, cheese, peanuts, almonds, pumpkin seeds, sesame seeds, soy products, lima beans, avocados and bananas. Tyrosine is one of the few amino acids that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, including thyroid hormones (diiodotyrosine), catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism have been identified, such as hawkinsinuria and tyrosinemia I. The most common feature of these diseases is the increased amount of tyrosine in the blood, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements can help reverse these disease symptoms. Some adults also develop elevated tyrosine in their blood. This typically indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can help aleviate biochemical depression. However, tyrosine may not be good for treating psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-Dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-Dopa (http://www.dcnutrition.com). In addition to its role as a precursor for neurotransmitters, tyrosine plays an important role for the function of many proteins. Within many proteins or enzymes, certain tyrosine residues can be tagged (at the hydroxyl group) with a phosphate group (phosphorylated) by specialized protein kinases. In its phosphorylated form, tyrosine is called phosphotyrosine. Tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzymatic activity. Tyrosine (or its precursor phenylalanine) is also needed to synthesize the benzoquinone structure which forms part of coenzyme Q10. L-tyrosine is an optically active form of tyrosine having L-configuration. It has a role as an EC 1.3.1.43 (arogenate dehydrogenase) inhibitor, a nutraceutical, a micronutrient and a fundamental metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tyrosine and a L-alpha-amino acid. It is functionally related to a L-tyrosinal. It is a conjugate base of a L-tyrosinium. It is a conjugate acid of a L-tyrosinate(1-). It is an enantiomer of a D-tyrosine. It is a tautomer of a L-tyrosine zwitterion. Tyrosine is a non-essential amino acid. In animals it is synthesized from [phenylalanine]. It is also the precursor of [epinephrine], thyroid hormones, and melanin. L-Tyrosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). L-Tyrosine is the levorotatory isomer of the aromatic amino acid tyrosine. L-tyrosine is a naturally occurring tyrosine and is synthesized in vivo from L-phenylalanine. It is considered a non-essential amino acid; however, in patients with phenylketonuria who lack phenylalanine hydroxylase and cannot convert phenylalanine into tyrosine, it is considered an essential nutrient. In vivo, tyrosine plays a role in protein synthesis and serves as a precursor for the synthesis of catecholamines, thyroxine, and melanin. Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin. Dietary supplement, nutrient. Flavouring ingredient. L-Tyrosine is found in many foods, some of which are blue crab, sweet rowanberry, lemon sole, and alpine sweetvetch. An optically active form of tyrosine having L-configuration. L-Tyrosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=60-18-4 (retrieved 2024-07-01) (CAS RN: 60-18-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

L-Phenylalanine

C9H11NO2 (165.079)

Phenylalanine (Phe), also known as L-phenylalanine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (‚ÄìNH2) and carboxyl (‚ÄìCOOH) functional groups, along with a side chain (R group) specific to each amino acid. L-phenylalanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Phenylalanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aromatic, non-polar amino acid. In humans, phenylalanine is an essential amino acid and the precursor of the amino acid tyrosine. Like tyrosine, phenylalanine is also a precursor for catecholamines including tyramine, dopamine, epinephrine, and norepinephrine. Catecholamines are neurotransmitters that act as adrenalin-like substances. Interestingly, several psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper, and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in a number of high protein foods, such as meat, cottage cheese, and wheat germ. An additional dietary source of phenylalanine is artificial sweeteners containing aspartame (a methyl ester of the aspartic acid/phenylalanine dipeptide). As a general rule, aspartame should be avoided by phenylketonurics and pregnant women. When present in sufficiently high levels, phenylalanine can act as a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of phenylalanine are associated with at least five inborn errors of metabolism, including Hartnup disorder, hyperphenylalaninemia due to guanosine triphosphate cyclohydrolase deficiency, phenylketonuria (PKU), tyrosinemia type 2 (or Richner-Hanhart syndrome), and tyrosinemia type III (TYRO3). Phenylketonurics have elevated serum plasma levels of phenylalanine up to 400 times normal. High plasma concentrations of phenylalanine influence the blood-brain barrier transport of large neutral amino acids. The high plasma phenylalanine concentrations increase phenylalanine entry into the brain and restrict the entry of other large neutral amino acids (PMID: 19191004). Phenylalanine has been found to interfere with different cerebral enzyme systems. Untreated phenylketonuria (PKU) can lead to intellectual disability, seizures, behavioural problems, and mental disorders. It may also result in a musty smell and lighter skin. Classic PKU dramatically affects myelination and white matter tracts in untreated infants; this may be one major cause of neurological disorders associated with phenylketonuria. Mild phenylketonuria can act as an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. It has been recently suggested that PKU may resemble amyloid diseases, such as Alzheimers disease and Parkinsons disease, due to the formation of toxic amyloid-like assemblies of phenylalanine (PMID: 22706200). Phenylalanine also has some potential benefits. Phenylalanine can act as an effective pain reliever. Its use in premenstrual syndrome and Parkinsons may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-DOPA, produce a catecholamine-like effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. For instance, some tumours use more phen... L-phenylalanine is an odorless white crystalline powder. Slightly bitter taste. pH (1\\\\\\% aqueous solution) 5.4 to 6. (NTP, 1992) L-phenylalanine is the L-enantiomer of phenylalanine. It has a role as a nutraceutical, a micronutrient, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an algal metabolite, a mouse metabolite, a human xenobiotic metabolite and an EC 3.1.3.1 (alkaline phosphatase) inhibitor. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a phenylalanine and a L-alpha-amino acid. It is a conjugate base of a L-phenylalaninium. It is a conjugate acid of a L-phenylalaninate. It is an enantiomer of a D-phenylalanine. It is a tautomer of a L-phenylalanine zwitterion. Phenylalanine is an essential aromatic amino acid that is a precursor of melanin, [dopamine], [noradrenalin] (norepinephrine), and [thyroxine]. L-Phenylalanine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Phenylalanine is an essential aromatic amino acid in humans (provided by food), Phenylalanine plays a key role in the biosynthesis of other amino acids and is important in the structure and function of many proteins and enzymes. Phenylalanine is converted to tyrosine, used in the biosynthesis of dopamine and norepinephrine neurotransmitters. The L-form of Phenylalanine is incorporated into proteins, while the D-form acts as a painkiller. Absorption of ultraviolet radiation by Phenylalanine is used to quantify protein amounts. (NCI04) Phenylalanine is an essential amino acid and the precursor for the amino acid tyrosine. Like tyrosine, it is the precursor of catecholamines in the body (tyramine, dopamine, epinephrine and norepinephrine). The psychotropic drugs (mescaline, morphine, codeine, and papaverine) also have phenylalanine as a constituent. Phenylalanine is a precursor of the neurotransmitters called catecholamines, which are adrenalin-like substances. Phenylalanine is highly concentrated in the human brain and plasma. Normal metabolism of phenylalanine requires biopterin, iron, niacin, vitamin B6, copper and vitamin C. An average adult ingests 5 g of phenylalanine per day and may optimally need up to 8 g daily. Phenylalanine is highly concentrated in high protein foods, such as meat, cottage cheese and wheat germ. A new dietary source of phenylalanine is artificial sweeteners containing aspartame. Aspartame appears to be nutritious except in hot beverages; however, it should be avoided by phenylketonurics and pregnant women. Phenylketonurics, who have a genetic error of phenylalanine metabolism, have elevated serum plasma levels of phenylalanine up to 400 times normal. Mild phenylketonuria can be an unsuspected cause of hyperactivity, learning problems, and other developmental problems in children. Phenylalanine can be an effective pain reliever. Its use in premenstrual syndrome and Parkinsons may enhance the effects of acupuncture and electric transcutaneous nerve stimulation (TENS). Phenylalanine and tyrosine, like L-dopa, produce a catecholamine effect. Phenylalanine is better absorbed than tyrosine and may cause fewer headaches. Low phenylalanine diets have been prescribed for certain cancers with mixed results. Some tumors use more phenylalanine (particularly melatonin-producing tumors called melanoma). One strategy is to exclude this amino acid from the diet, i.e., a Phenylketonuria (PKU) diet (compliance is a difficult issue; it is hard to quantify and is under-researched). The other strategy is just to increase phenylalanines competing amino acids, i.e., tryptophan, valine, isoleucine and leucine, but not tyrosine. An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE. See also: Plovamer (monomer of); Plovamer Acetate (monomer of) ... View More ... L-phenylalanine, also known as phe or f, belongs to phenylalanine and derivatives class of compounds. Those are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-phenylalanine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). L-phenylalanine can be found in watermelon, which makes L-phenylalanine a potential biomarker for the consumption of this food product. L-phenylalanine can be found primarily in most biofluids, including sweat, blood, urine, and cerebrospinal fluid (CSF), as well as throughout all human tissues. L-phenylalanine exists in all living species, ranging from bacteria to humans. In humans, L-phenylalanine is involved in a couple of metabolic pathways, which include phenylalanine and tyrosine metabolism and transcription/Translation. L-phenylalanine is also involved in few metabolic disorders, which include phenylketonuria, tyrosinemia type 2 (or richner-hanhart syndrome), and tyrosinemia type 3 (TYRO3). Moreover, L-phenylalanine is found to be associated with viral infection, dengue fever, hypothyroidism, and myocardial infarction. L-phenylalanine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Phenylalanine (Phe or F) is an α-amino acid with the formula C 9H 11NO 2. It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino acid is classified as neutral, and nonpolar because of the inert and hydrophobic nature of the benzyl side chain. The L-isomer is used to biochemically form proteins, coded for by DNA. The codons for L-phenylalanine are UUU and UUC. Phenylalanine is a precursor for tyrosine; the monoamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline); and the skin pigment melanin . Hepatic. L-phenylalanine that is not metabolized in the liver is distributed via the systemic circulation to the various tissues of the body, where it undergoes metabolic reactions similar to those that take place in the liver (DrugBank). If PKU is diagnosed early, an affected newborn can grow up with normal brain development, but only by managing and controlling phenylalanine levels through diet, or a combination of diet and medication. The diet requires severely restricting or eliminating foods high in phenylalanine, such as meat, chicken, fish, eggs, nuts, cheese, legumes, milk and other dairy products. Starchy foods, such as potatoes, bread, pasta, and corn, must be monitored. Optimal health ranges (or "target ranges") of serum phenylalanine are between 120 and 360 µmol/L, and aimed to be achieved during at least the first 10 years of life. Recently it has been found that a chiral isomer of L-phenylalanine (called D-phenylalanine) actually arrests the fibril formation by L-phenylalanine and gives rise to flakes. These flakes do not propagate further and prevent amyloid formation by L-phenylalanine. D-phenylalanine may qualify as a therapeutic molecule in phenylketonuria (A8161) (T3DB). L-Phenylalanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=63-91-2 (retrieved 2024-07-01) (CAS RN: 63-91-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

Se-Methylselenocysteine

C4H9NO2Se (182.9798)

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].

Asparagusic acid

C4H6O2S2 (149.9809)

Asparagusic acid is a sulfur-containing carboxylic acid, a dithiolanecarboxylic acid and a member of dithiolanes. It is a conjugate acid of an asparagusate. It derives from a hydride of a 1,2-dithiolane. Asparagusic acid is a natural product found in Asparagus officinalis with data available. Asparagusic acid is found in asparagus. Asparagusic acid is isolated from asparagus (Asparagus officinalis Isolated from asparagus (Asparagus officinalis) [DFC] Asparagusic acid is a sulfur-containing flavor component produced by Asparagus officinalis Linn., with anti-parasitic effect. Asparagusic acid is a plant growth inhibitor[1][2][3].

Mimosine

C8H10N2O4 (198.0641)

Mimosine is only found in individuals that have used or taken this drug. It is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. [PubChem]Mimosine causes inhibition of DNA replication, changes in the progression of the cells in the cell cycle, and apoptosis. Mimosine appears to introduce breaks into DNA. Mimosine is an iron/zinc chelator. Iron depletion induces DNA double-strand breaks in treated cells, and activates a DNA damage response that results in focal phosphorylation of histones. This leads to inhibition of DNA replication and/or DNA elongation. Some studies indicate that mimosine prevents the initiation of DNA replication, whereas other studies indicate that mimosine disrupts elongation of the replication fork by impairing deoxyribonucleotide synthesis by inhibiting the activity of the iron-dependent enzyme ribonucleotide reductase and the transcription of the cytoplasmic serine hydroxymethyltransferase gene (SHMT). Inhibition of serine hydroxymethyltransferase is moderated by a zinc responsive unit located in front of the SHMT gene. L-mimosine is an L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a non-proteinogenic L-alpha-amino acid and a member of 4-pyridones. It is functionally related to a propionic acid. It is a conjugate acid of a L-mimosine(1-). It is a tautomer of a L-mimosine zwitterion. Mimosine is an antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. 3-Hydroxy-4-oxo-1(4H)-pyridinealanine. An antineoplastic alanine-substituted pyridine derivative isolated from Leucena glauca. An L-alpha-amino acid that is propionic acid substituted by an amino group at position 2 and a 3-hydroxy-4-oxopyridin-1(4H)-yl group at position 3 (the 2S-stereoisomer). It a non-protein plant amino acid isolated from Mimosa pudica. Mimosine, a tyrosine analog , can act as an antioxidant by its potent iron-binding activity[1]. Mimosine is a known chelator of Fe(III)[2]. Mimosine induces apoptosis through metal ion chelation, mitochondrial activation and ROS production in human leukemic cells[3]. Anti-cancer, antiinflammation. Mimosine, a tyrosine analog , can act as an antioxidant by its potent iron-binding activity[1]. Mimosine is a known chelator of Fe(III)[2]. Mimosine induces apoptosis through metal ion chelation, mitochondrial activation and ROS production in human leukemic cells[3]. Anti-cancer, antiinflammation.

Taxiphyllin

C14H17NO7 (311.1005)

(R)-4-hydroxymandelonitrile beta-D-glucoside is a beta-D-glucoside consisting of (R)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring. It is a beta-D-glucoside and a nitrile. It is functionally related to a (R)-prunasin. Taxiphyllin is a natural product found in Girgensohnia oppositiflora, Caroxylon tetrandrum, and other organisms with data available. Dhurrin is found in borage. Cyanogenic glucoside isolated from Sorghum vulgare (sorghum) Dhurrin is a cyanogenic glycoside occurring in plants. Its biosynthesis has been elucidated. Dhurrin is hydrolyzed in the stomach of an insect into a carbohydrate and aglycone. The aglycone is unstable and releases hydrogen cyanide Cyanogenic glucoside of Macadamia ternifolia. Taxiphyllin is found in many foods, some of which are naranjilla, bayberry, celeriac, and red beetroot.

3-Hydroxyanthranilic acid

C7H7NO3 (153.0426)

3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid is a drug. 3-Hydroxyanthranilic acid exists in all living species, ranging from bacteria to humans. Within humans, 3-hydroxyanthranilic acid participates in a number of enzymatic reactions. In particular, 3-hydroxyanthranilic acid and L-alanine can be biosynthesized from L-3-hydroxykynurenine through the action of the enzyme kynureninase. In addition, 3-hydroxyanthranilic acid can be converted into cinnavalininate through the action of the enzyme catalase. 3-Hydroxyanthranilic acid is an intermediate in the metabolism of tryptophan. In humans, 3-hydroxyanthranilic acid is involved in tryptophan metabolism. Outside of the human body, 3-hydroxyanthranilic acid has been detected, but not quantified in brassicas. This could make 3-hydroxyanthranilic acid a potential biomarker for the consumption of these foods. It is new antioxidant isolated from methanol extract of tempeh. It is effective in preventing autoxidation of soybean oil and powder, while antioxidant 6,7,4-trihydroxyisoflavone is not. D000975 - Antioxidants > D016166 - Free Radical Scavengers [Raw Data] CBA14_3-OH-anthranili_pos_30eV_1-6_01_808.txt [Raw Data] CBA14_3-OH-anthranili_neg_40eV_1-6_01_832.txt [Raw Data] CBA14_3-OH-anthranili_pos_40eV_1-6_01_809.txt [Raw Data] CBA14_3-OH-anthranili_neg_20eV_1-6_01_830.txt [Raw Data] CBA14_3-OH-anthranili_neg_10eV_1-6_01_829.txt [Raw Data] CBA14_3-OH-anthranili_pos_10eV_1-6_01_806.txt [Raw Data] CBA14_3-OH-anthranili_pos_20eV_1-6_01_807.txt [Raw Data] CBA14_3-OH-anthranili_neg_30eV_1-6_01_831.txt D020011 - Protective Agents > D000975 - Antioxidants Isolated from Brassica oleracea (cauliflower) 3-Hydroxyanthranilic acid is a tryptophan metabolite in the kynurenine pathway.

1-Methylhistidine

C7H11N3O2 (169.0851)

1-Methylhistidine, also known as 1-MHis or 1MH, belongs to the class of organic compounds known as histidine and derivatives. 1MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as pi-methylhistidine) or 3-methylhistidine (3MH; tau-methylhistidine), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine and other histidine-containing peptides such as anserine. In particular, older literature (mostly prior to the year 2000) designated anserine (Npi methylated) as beta-alanyl-N1-methyl-histidine, whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methyl-histidine. As a result, many papers published prior to the year 2000 incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really were referring to 3MH (PMID: 24137022). Recent discoveries have shown that 1MH is produced in essentially all mammals (and other vertebrates) via the enzyme known as METTL9 (PMID: 33563959). METTL9 is a broad-specificity methyltransferase that mediates the formation of the majority of 1MH present in mammalian proteomes. METTL9-catalyzed methylation requires a His-x-His (HxH) motif, where "x" is a small amino acid. This HxH motif is found in a number of abundant mammalian proteins such as ARMC6, S100A9, and NDUFB3 (PMID: 33563959). Because of its abundance in many muscle-related proteins, 1MH has been found to be a good biomarker for the consumption of meat (PMID: 21527577). Dietary studies have shown that poultry consumption (p-trend = 0.0006) and chicken consumption (p-trend = 0.0003) are associated with increased levels of 1MH in human plasma (PMID: 30018457). The consumption of fish, especially salmon and cod, has also been shown to increase the levels of 1MH in serum and urine (PMID: 31401679). As a general rule, urinary 1MH is associated with white meat intake (p< 0.001), whereas urinary 3MH is associated with red meat intake (p< 0.001) (PMID: 34091671). 1-Methyl-L-histidine is an objective indicator of meat ingestion and exogenous 3-methylhistidine (3MH) intake. 1-Methyl-L-histidine is an objective indicator of meat ingestion and exogenous 3-methylhistidine (3MH) intake. 3-Methyl-L-histidine is a biomarker for meat consumption, especially chicken. It is also a biomarker for the consumption of soy products.

4-Aminobenzoic acid

C7H7NO2 (137.0477)

p-Aminobenzoic acid, also known as 4-aminobenzoic acid or PABA, is an organic compound with molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid. PABA is an essential nutrient for some bacteria and is sometimes called vitamin Bx. However, PABA is not essential for humans and it varies in its activity from other B vitamins. PABA is sometimes marketed as an essential nutrient under the premise that it can stimulate intestinal bacteria. Certain bacteria in the human intestinal tract such as E. coli generate PABA from chorismate. Humans lack the enzymes to convert PABA into folate, and therefore require folate from dietary sources such as green leafy vegetables. Although some intestinal bacteria can synthesize folate from PABA and some E. coli can synthesize folate this requires six enzymatic activities in folate synthesis which are not all done in the same bacteria. PABA used to be a common sunscreen agent until it was found to also be a sensitizer. The potassium salt of PABA is used therapeutically in fibrotic skin disorders. PABA can also be found in Acetobacter (DOI: 10.3181/00379727-52-14147). CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2913; ORIGINAL_PRECURSOR_SCAN_NO 2910 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2878; ORIGINAL_PRECURSOR_SCAN_NO 2876 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3022; ORIGINAL_PRECURSOR_SCAN_NO 3020 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX499; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 2902; ORIGINAL_PRECURSOR_SCAN_NO 2899 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3034; ORIGINAL_PRECURSOR_SCAN_NO 3032 CONFIDENCE standard compound; INTERNAL_ID 1139; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3039; ORIGINAL_PRECURSOR_SCAN_NO 3037 D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BA - Protectives against uv-radiation for topical use Acquisition and generation of the data is financially supported in part by CREST/JST. Listed in the EAFUS Food Additive Database (Jan. 2001) but with no reported use KEIO_ID A043 4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi. 4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi.

5-Hydroxylysine

C6H14N2O3 (162.1004)

5-Hydroxylysine (Hyl), also known as hydroxylysine or 5-Hydroxy-L-lysine, 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. Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. 5-Hydroxylysine is a hydroxylated derivative of the amino acid lysine that is present in certain collagens, the chief structural protein of mammalian skin and connective tissue. 5-Hydroxylysine arises from a post-translational hydroxy modification of lysine and is biosynthesized from lysine via oxidation by lysyl hydroxylase enzymes. 5-Hydroxylysine can then undergo further modification by glycosylation, giving rise to galactosyl hydroxylysine (GH) and glucosylgalactosyl hydroxylysine (GGH). These glycosylated forms of hydroxylysine contribute to collagen’s unusual toughness and resiliency. The monoglycosylated, galactosyl-hydroxylysine is enriched in bone compared with the disaccharide form, glucosyl-galactosyl-hydroxylysine, which is the major form in skin. 5-Hydroxylysine exists in all eukaryotes, ranging from yeast to humans. It was first discovered in 1921 by Donald Van Slyke. Free forms of hydroxylysine arise through proteolytic degradation of collagen. Urinary excretion of 5-Hydroxylysine and its glycosides can be used as an index of collagen degradation, with high levels being indicative of more rapid or extensive collagen degradation (often seen in patients with thermal burns, Pagets disease of bone or hyperphosphatasia) (PMID: 404321). One of the natural protein-bound amino acids. Occurs free in plant tissues, e.g. Medicago sativa (alfalfa)

Creatine

C4H9N3O2 (131.0695)

Creatine, is a naturally occurring non-protein compound. It belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Creatine is found in all vertebrates where it facilitates recycling of adenosine triphosphate (ATP). Its primary metabolic role is to combine with a phosphoryl group, via the enzyme creatine kinase, to generate phosphocreatine, which is used to regenerate ATP. Most of the human bodys total creatine and phosphocreatine stores are found in skeletal muscle (95\\\\\%), while the remainder is distributed in the blood, brain, testes, and other tissues. Creatine is not an essential nutrient as it is naturally produced in the human body from the amino acids glycine and arginine, with an additional requirement for methionine to catalyze the transformation of guanidinoacetate to creatine. In the first step of its biosynthesis glycine and arginine are combined by the enzyme arginine:glycine amidinotransferase (AGAT) to form guanidinoacetate, which is then methylated by guanidinoacetate N-methyltransferase (GAMT), using S-adenosyl methionine as the methyl donor. Creatine can also be obtained through the diet at a rate of about 1 gram per day from an omnivorous diet. A cyclic form of creatine, called creatinine, exists in equilibrium with its tautomer and with creatine. Clinically, there are three distinct disorders of creatine metabolism. Deficiencies in the two synthesis enzymes (AGAT and GAMT) can cause L-arginine:glycine amidinotransferase deficiency (caused by variants in AGAT) and guanidinoacetate methyltransferase deficiency (caused by variants in GAMT). Both disorders are inherited in an autosomal recessive manner. A third defect, creatine transporter defect, is caused by mutations in SLC6A8 and inherited in a X-linked manner. Creatine is widely used as a supplement by athletes. Its use can increase maximum power and performance in high-intensity anaerobic repetitive work (periods of work and rest) by 5 to 15\\\\\% (PMID: 24688272). Creatine has no significant effect on aerobic endurance, although it will increase power during short sessions of high-intensity aerobic exercise (PMID: 9662683). [Spectral] Creatine (exact mass = 131.06948) and L-Aspartate (exact mass = 133.03751) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Creatine (exact mass = 131.06948) and L-Cysteine (exact mass = 121.01975) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Creatine is a essential, non-proteinaceous amino acid found in all animals and in some plants. Creatine is synthesized in the kidney, liver and pancreas from L-arginine, glycine and L-methionine. Creatine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-00-1 (retrieved 2024-06-29) (CAS RN: 57-00-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

L-Cystathionine

C7H14N2O4S (222.0674)

Cystathionine is a dipeptide formed by serine and homocysteine. Cystathioninuria is a prominent manifestation of vitamin-B6 deficiency. The transsulfuration of methionine yields homocysteine, which combines with serine to form cystathionine, the proximate precursor of cysteine through the enzymatic activity of cystathionase. In conditions in which cystathionine gamma-synthase or cystathionase is deficient, for example, there is cystathioninuria. Although cystathionine has not been detected in normal human serum or plasma by most conventional methods, gas chromatographic/mass spectrometric methodology detected a mean concentration of cystathionine in normal human serum of 140 nM, with a range of 65 to 301 nM. Cystathionine concentrations in CSF have been 10, 1, and 0.5 uM, and "not detected". Only traces (i.e., <1 uM) of cystathionine are present in normal CSF.587. Gamma-cystathionase deficiency (also known as Cystathioninuria), which is an autosomal recessive disorder (NIH: 2428), provided the first instance in which, in a human, the major biochemical abnormality due to a defined enzyme defect was clearly shown to be alleviated by administration of large doses of pyridoxine. The response in gamma-cystathionase-deficient patients is not attributable to correction of a preexisting deficiency of this vitamin (OMMBID, Chap. 88). Isolated from Phallus impudicus (common stinkhorn) CONFIDENCE standard compound; INTERNAL_ID 146 KEIO_ID C019; [MS2] KO008910 KEIO_ID C047 KEIO_ID C019 Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; ML_ID 30 L-Cystathionine is a nonprotein thioether and is a key amino acid associated with the metabolic state of sulfur-containing amino acids. L-Cystathionine protects against Homocysteine-induced mitochondria-dependent apoptosis of vascular endothelial cells (HUVECs). L-Cystathionine plays an important role in cardiovascular protection[1][2]. L-Cystathionine is a nonprotein thioether and is a key amino acid associated with the metabolic state of sulfur-containing amino acids. L-Cystathionine protects against Homocysteine-induced mitochondria-dependent apoptosis of vascular endothelial cells (HUVECs). L-Cystathionine plays an important role in cardiovascular protection[1][2].

Homocysteine

C4H9NO2S (135.0354)

A high level of blood serum homocysteine is a powerful risk factor for cardiovascular disease. Unfortunately, one study which attempted to decrease the risk by lowering homocysteine was not fruitful. This study was conducted on nearly 5000 Norwegian heart attack survivors who already had severe, late-stage heart disease. No study has yet been conducted in a preventive capacity on subjects who are in a relatively good state of health.; Elevated levels of homocysteine have been linked to increased fractures in elderly persons. The high level of homocysteine will auto-oxidize and react with reactive oxygen intermediates and damage endothelial cells and has a higher risk to form a thrombus. Homocysteine does not affect bone density. Instead, it appears that homocysteine affects collagen by interfering with the cross-linking between the collagen fibers and the tissues they reinforce. Whereas the HOPE-2 trial showed a reduction in stroke incidence, in those with stroke there is a high rate of hip fractures in the affected side. A trial with 2 homocysteine-lowering vitamins (folate and B12) in people with prior stroke, there was an 80\\\\\\% reduction in fractures, mainly hip, after 2 years. Interestingly, also here, bone density (and the number of falls) were identical in the vitamin and the placebo groups.; Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Although its concentration in plasma is only about 10 micromolar (uM), even moderate hyperhomocysteinemia is associated with increased incidence of cardiovascular disease and Alzheimers disease. Elevations in plasma homocysteine are commonly found as a result of vitamin deficiencies, polymorphisms of enzymes of methionine metabolism, and renal disease. Pyridoxal, folic acid, riboflavin, and Vitamin B(12) are all required for methionine metabolism, and deficiency of each of these vitamins result in elevated plasma homocysteine. A polymorphism of methylenetetrahydrofolate reductase (C677T), which is quite common in most populations with a homozygosity rate of 10-15 \\\\\\%, is associated with moderate hyperhomocysteinemia, especially in the context of marginal folate intake. Plasma homocysteine is inversely related to plasma creatinine in patients with renal disease. This is due to an impairment in homocysteine removal in renal disease. The role of these factors, and of modifiable lifestyle factors, in affecting methionine metabolism and in determining plasma homocysteine levels is discussed. Homocysteine is an independent cardiovascular disease (CVD) risk factor modifiable by nutrition and possibly exercise. Homocysteine was first identified as an important biological compound in 1932 and linked with human disease in 1962 when elevated urinary homocysteine levels were found in children with mental retardation. This condition, called homocysteinuria, was later associated with premature occlusive CVD, even in children. These observations led to research investigating the relationship of elevated homocysteine levels and CVD in a wide variety of populations including middle age and elderly men and women with and without traditional risk factors for CVD. (PMID 17136938, 15630149); Homocysteine is an amino acid with the formula HSCH2CH2CH(NH2)CO2H. It is a homologue of the amino acid cysteine, differing by an additional methylene (-CH2-) group. It is biosynthesized from methionine by the removal of its terminal C? methyl group. Homocysteine can be recycled into methionine or converted into cysteine with the aid of B-vitamins.; Studies reported in 2006 have shown that giving vitamins [folic acid, B6 and B12] to reduce homocysteine levels may not quickly offer benefit, however a significant 25\\\\\\% reduction in stroke was found in the HOPE-2 study even in patients mostly with existing serious arterial decline although the overall death rate was not significantly changed by the intervention in the trial. Clearly, reducing homocysteine does not quickly repair existing... Homocysteine (CAS: 454-29-5) is a sulfur-containing amino acid that arises during methionine metabolism. Although its concentration in plasma is only about 10 micromolar (uM), even moderate hyperhomocysteinemia is associated with an increased incidence of cardiovascular disease and Alzheimers disease. Elevations in plasma homocysteine are commonly found as a result of vitamin deficiencies, polymorphisms of enzymes of methionine metabolism, and renal disease. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Pyridoxal, folic acid, riboflavin, and vitamin B(12) are all required for methionine metabolism, and deficiency of each of these vitamins result in elevated plasma homocysteine. A polymorphism of methylenetetrahydrofolate reductase (C677T), which is quite common in most populations with a homozygosity rate of 10-15 \\\\\\%, is associated with moderate hyperhomocysteinemia, especially in the context of marginal folate intake. Plasma homocysteine is inversely related to plasma creatinine in patients with renal disease. This is due to an impairment in homocysteine removal in renal disease. The role of these factors, and of modifiable lifestyle factors, in affecting methionine metabolism and in determining plasma homocysteine levels is discussed. Homocysteine is an independent cardiovascular disease (CVD) risk factor modifiable by nutrition and possibly exercise. Homocysteine was first identified as an important biological compound in 1932 and linked with human disease in 1962 when elevated urinary homocysteine levels were found in children with mental retardation. This condition, called homocystinuria, was later associated with premature occlusive CVD, even in children. These observations led to research investigating the relationship of elevated homocysteine levels and CVD in a wide variety of populations including middle age and elderly men and women with and without traditional risk factors for CVD (PMID: 17136938 , 15630149). Moreover, homocysteine is found to be associated with cystathionine beta-synthase deficiency, cystathioninuria, methylenetetrahydrofolate reductase deficiency, and sulfite oxidase deficiency, which are inborn errors of metabolism. [Spectral] L-Homocysteine (exact mass = 135.0354) and L-Valine (exact mass = 117.07898) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Homocysteine is biosynthesized naturally via a multi-step process.[9] First, methionine receives an adenosine group from ATP, a reaction catalyzed by S-adenosyl-methionine synthetase, to give S-adenosyl methionine (SAM-e). SAM-e then transfers the methyl group to an acceptor molecule, (e.g., norepinephrine as an acceptor during epinephrine synthesis, DNA methyltransferase as an intermediate acceptor in the process of DNA methylation). The adenosine is then hydrolyzed to yield L-homocysteine. L-Homocysteine has two primary fates: conversion via tetrahydrofolate (THF) back into L-methionine or conversion to L-cysteine.[10] Biosynthesis of cysteine Mammals biosynthesize the amino acid cysteine via homocysteine. Cystathionine β-synthase catalyses the condensation of homocysteine and serine to give cystathionine. This reaction uses pyridoxine (vitamin B6) as a cofactor. Cystathionine γ-lyase then converts this double amino acid to cysteine, ammonia, and α-ketobutyrate. Bacteria and plants rely on a different pathway to produce cysteine, relying on O-acetylserine.[11] Methionine salvage Homocysteine can be recycled into methionine. This process uses N5-methyl tetrahydrofolate as the methyl donor and cobalamin (vitamin B12)-related enzymes. More detail on these enzymes can be found in the article for methionine synthase. Other reactions of biochemical significance Homocysteine can cyclize to give homocysteine thiolactone, a five-membered heterocycle. Because of this "self-looping" reaction, homocysteine-containing peptides tend to cleave themselves by reactions generating oxidative stress.[12] Homocysteine also acts as an allosteric antagonist at Dopamine D2 receptors.[13] It has been proposed that both homocysteine and its thiolactone may have played a significant role in the appearance of life on the early Earth.[14] L-Homocysteine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=454-28-4 (retrieved 2024-06-29) (CAS RN: 6027-13-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Homocysteine is a weak neurotoxin, and can affect the production of kynurenic acid in the brain. DL-Homocysteine is a weak neurotoxin, and can affect the production of kynurenic acid in the brain. L-Homocysteine, a homocysteine metabolite, is a homocysteine that has L configuration. L-Homocysteine induces upregulation of cathepsin V that mediates vascular endothelial inflammation in hyperhomocysteinaemia[1][2].

Guanidinosuccinic acid

C5H9N3O4 (175.0593)

Guanidinosuccinic acid (GSA) has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). It is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806). Guanidinosuccinic acid (GSA) is one of the earliest uremic toxins isolated and its toxicity identified. Its metabolic origins show that it arose from the oxidation of argininosuccinic acid (ASA) by free radicals. The stimulus for this oxidation, occurring optimally in the presence of the failed kidney, is the rising level of urea which, through enzyme inhibition, results in a decline in hepatic levels of the semi-essential amino acid, arginine. It is further noted that concentrations of GSA in both serum and urine decline sharply in animals and humans exposed to the essential amino acid, methionine. Uremic patients suffer from a defective ability to generate methyl groups due to anorexia, dietary restrictions and renal protein leakage. This leads to the accumulation of homocysteine, a substance known to produce vascular damage. Even in healthy subjects intake of choline together with methionine is insufficient to satisfy total metabolic requirements for methyl groups. In end-stage renal disease, therefore, protein restriction contributes to the build-up of toxins in uremia. Replacement using specific amino acid mixtures should be directed toward identified deficiencies and adequacy monitored by following serum levels of the related toxins, in this case GSA and homocysteine. (PMID 12701806) [HMDB] Guanidinosuccinic acid is a nitrogenous metabolite.

Cysteine S-sulfate

C3H7NO5S2 (200.9766)

Cysteine-S-sulfate (SSC) is produced by reaction of inorganic sulfite and cystine by a yet unknown pathway and is a very potent NMDA-receptor agonist. Electrophysiological studies have shown that SSC displays depolarizing properties similar to glutamate. Patients affected with either Molybdenum cofactor deficiency (MOCOD, an autosomal recessive disease that leads to a combined deficiency of the enzymes sulphite oxidase, an enzyme that catalyzes the conversion of sulfite to inorganic sulfate, xanthine dehydrogenase and aldehyde oxidase) or isolated sulphite oxidase deficiency (ISOD, an extremely rare autosomal recessive disorder with identical clinical manifestations to MOCOD) excrete elevated levels of SSC. This rare disorder is associated with brain damage (seizures, spastic quadriplegia, and cerebral atrophy), mental retardation, dislocated ocular lenses, blindness, and excretion in the urine of abnormally large amounts of SSC, sulfite, and thiosulfate but no inorganic sulfate (PMID: 17764028, 15558695). Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID C127; [MS2] KO008902 KEIO_ID C127

L-Histidine

C6H9N3O2 (155.0695)

Histidine (His), also known as L-histidine, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Histidine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Histidine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. Histidine is a unique amino acid with an imidazole functional group. The acid-base properties of the imidazole side chain are relevant to the catalytic mechanism of many enzymes such as proteases. In catalytic triads, the basic nitrogen of histidine abstracts a proton from serine, threonine, or cysteine to activate it as a nucleophile. In a histidine proton shuttle, histidine is used to quickly shuttle protons. It can do this by abstracting a proton with its basic nitrogen to make a positively charged intermediate and then use another molecule to extract the proton from its acidic nitrogen. Histidine forms complexes with many metal ions. The imidazole sidechain of the histidine residue commonly serves as a ligand in metalloproteins. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. It was initially thought that it was only essential for infants, but longer-term studies established that it is also essential for adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Histidine is a precursor for histamine and carnosine biosynthesis. Inborn errors of histidine metabolism, including histidinemia, maple syrup urine disease, propionic acidemia, and tyrosinemia I, exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine and other imidazole compounds have anti-oxidant, anti-inflammatory and anti-secretory properties (PMID: 9605177 ). The efficacy of L-histidine in protecting inflamed tissue is attributed to the capacity of the imidazole ring to scavenge reactive oxygen species (ROS) generated by cells during acute inflammatory response (PMID: 9605177 ). Histidine, when administered in therapeutic quantities is able to inhibit cytokines and growth factors involved in cell and tissue damage (US patent 6150392). Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of very rapid removal of histidine from their blood (PMID: 1079527 ). Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Urinary levels of histidine are reduced in pediatric patients with pneumonia (PMID: 2084459 ). Asthma patients exhibit increased serum levels of histidine over normal controls (PMID: 23517038 ). Serum histidine levels are lower and are negatively associated with inflammation and oxidative stress in obese women (PMID: 23361591 ). Histidine supplementation has been shown to reduce insulin resistance, reduce BMI and fat mass and suppress inflammation and oxidative stress in obese women with metabolic syndrome. Histidine appears to suppress pro-inflammatory cytokine expression, possibly via the NF-κB pathway, in adipocytes (PMID: 23361591 ). Low plasma concentrations of histidine are associated with protein-energy... [Spectral] L-Histidine (exact mass = 155.06948) and L-Lysine (exact mass = 146.10553) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] L-Histidine (exact mass = 155.06948) and L-Arginine (exact mass = 174.11168) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. Flavouring ingredient; dietary supplement, nutrient L-Histidine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=71-00-1 (retrieved 2024-07-01) (CAS RN: 71-00-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

DL-Homocystine

C8H16N2O4S2 (268.0551)

Homocystine is the oxidized form of homocysteine. Homocystine is a dipeptide consisting of two homocysteine molecules joined by a disulfide bond. Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Homocystine occurs only transiently before being reduced to homocysteine and converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfides account for >98\\\\\% of total homocysteine in plasma from healthy individuals (PMID 11592966). Homocystine has been shown to stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells, thereby inducing a vascular cell type-specific oxidative stress. This vascular stress is associated with atherothrombotic cardiovascular disease (PMID: 14980706). High levels of homocysteine (and homocysteine) can be found in individuals suffering from homocystinura due to cystathionine synthase deficiency (PMID: 4685596) Homocystine is the double-bonded form of homocysteine, but it occurs only transiently before being converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H041 4,4'-Disulfanediylbis(2-aminobutanoic acid) is an endogenous metabolite. DL-Homocystine is the double-bonded form of homocysteine and homocysteine is recognized as an important substance in the pathogenesis and pathophysiology of schizophrenia. L-Homocystine is the oxidized member of the L-homocysteine. Homocysteine is a pro-thrombotic factor, vasodilation impairing agent, pro-inflammatory factor and endoplasmatic reticulum-stress inducer used to study cardiovascular disease mechanisms.

Saccharopine

C11H20N2O6 (276.1321)

Saccharopine is an intermediate in the degradation of lysine, formed by the condensation of lysine and alpha-ketoglutarate. The saccharopine pathway is the main route for lysine degradation in mammals, and its first two reactions are catalyzed by enzymatic activities known as lysine-oxoglutarate reductase (LOR) and saccharopine dehydrogenase (SDH), which reside on a single bifunctional polypeptide (LOR/SDH) (EC 1.5.1.8). The reactions involved with saccharopine dehydrogenases have very strict substrate specificity for L-lysine, 2-oxoglutarate, and NADPH. LOR/SDH has been detected in a number of mammalian tissues, mainly in the liver and kidney, contributing not only to the general nitrogen balance in the organism but also to the controlled conversion of lysine into ketone bodies. A tetrameric form has also been observed in human liver and placenta. LOR activity has also been detected in brain mitochondria during embryonic development, and this opens up the question of whether or not lysine degradation has any functional significance during brain development. As a result, there is now a new focus on the nutritional requirements for lysine in gestation and infancy. Finally, LOR and/or SDH deficiencies seem to be involved in a human autosomal genetic disorder known as familial hyperlysinemia, which is characterized by serious defects in the functioning of the nervous system and characterized by a deficiency in lysine-ketoglutarate reductase, saccharopine dehydrogenase, and saccharopine oxidoreductase activities. Saccharopinuria (high amounts of saccharopine in the urine) and saccharopinemia (an excess of saccharopine in the blood) are conditions present in some inherited disorders of lysine degradation (PMID: 463877, 10567240, 10772957, 4809305). If present in sufficiently high levels, saccharopine can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Saccharopine is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). Many affected children with organic acidemias experience intellectual disability or delayed development. Amino acid from Saccharomyces cerevisiae and Neurospora crassaand is also found in mushrooms and seeds

O-Acetylserine

C5H9NO4 (147.0532)

O-Acetylserine is an α-amino acid with the chemical formula HO2CCH(NH2)CH2OC(O)CH3. It is an intermediate in the biosynthesis of the common amino acid cysteine in bacteria and plants. O-Acetylserine is biosynthesized by acetylation of the serine by the enzyme serine transacetylase. The enzyme O-acetylserine (thiol)-lyase, using sulfide sources, converts this ester into cysteine, releasing acetate. O-Acetylserine 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. O-Acetylserine (OASS) is an acylated amino acid derivative. O-Acetylserine exists in all living species, ranging from bacteria to humans. Outside of the human body, O-Acetylserine has been detected, but not quantified in several different foods, such as okra, vaccinium (blueberry, cranberry, huckleberry), rapes, sparkleberries, and lingonberries. This could make O-acetylserine a potential biomarker for the consumption of these foods. O-acetyl-l-serine, also known as L-serine, acetate (ester) or (2s)-3-acetyloxy-2-aminopropanoate, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. O-acetyl-l-serine is soluble (in water) and a moderately acidic compound (based on its pKa). O-acetyl-l-serine can be found in a number of food items such as sorrel, summer savory, purslane, and cherimoya, which makes O-acetyl-l-serine a potential biomarker for the consumption of these food products. O-acetyl-l-serine can be found primarily in blood and urine, as well as in human prostate tissue. O-acetyl-l-serine exists in all living species, ranging from bacteria to humans. Acquisition and generation of the data is financially supported in part by CREST/JST. O-Acetylserine (O-Acetyl-L-serine) is an intermediate in the biosynthesis of the amino acid cysteine in bacteria and plants.

3,5-Diiodo-L-tyrosine

C9H9I2NO3 (432.8672)

3,5-Diiodo-L-tyrosine, also known as diiy or DIT, belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 3,5-Diiodo-L-tyrosine exists in all living organisms, ranging from bacteria to humans. In humans, 3,5-diiodo-L-tyrosine is involved in thyroid hormone synthesis. 3,5-Diiodo-L-tyrosine is a product from the iodination of monoiodotyrosine. A product from the iodination of monoiodotyrosine. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (thyroxine and triiodothyronine). [HMDB] H - Systemic hormonal preparations, excl. sex hormones and insulins > H03 - Thyroid therapy > H03B - Antithyroid preparations D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones KEIO_ID D056

Cyclohexanecarboxylic acid

C7H12O2 (128.0837)

Cyclohexanecarboxylic acid is a flavouring ingredien Flavouring ingredient KEIO_ID C180 Cyclohexanecarboxylic acid is a Valproate structural analogue with anticonvulsant action[1].

Phosphocreatine

C4H10N3O5P (211.0358)

Phosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylated creatine molecule that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle, myocardium and the brain to recycle adenosine triphosphate, the energy currency of the cell. Phosphocreatine undergoes irreversible cyclization and dehydration to form creatinine at a fractional rate of 0.026 per day, thus forming approximately 2 g creatinine/day in an adult male. This is the amount of creatine that must be provided either from dietary sources or by endogenous synthesis to maintain the body pool of (creatine and) phosphocreatine. Creatine is an amino acid that plays a vital role as phosphocreatine in regenerating adenosine triphosphate in skeletal muscle to energize muscle contraction. Creatine is phosphorylated to phosphocreatine in muscle in a reaction that is catalyzed by the enzyme creatine kinase. This enzyme is in highest concentration in muscle and nerve. Oral administration increases muscle stores. During the past decade, creatine has assumed prominence as an ergogenic (and legal) aid for professional and elite athletes. Most (~ 95\\%) of the total body creatine-phosphocreatine pool is in muscle (more in skeletal muscle than in smooth muscle) and amounts to 120 g (or 925 mmol) in a 70 kg adult male. Approximately 60-67\\% of the content in resting muscle is in the phosphorylated form. This generates enough ATP at the myofibrillar apparatus to power about 4 seconds of muscle contraction in exercise. Phosphocreatine reacts with ADP to yield ATP and creatine; the reversible reaction is catalyzed by creatine kinase. phosphocreatine is the chief store of high-energy phosphates in muscle. Thus, this reaction, which permits the rephosphorylation of ADP to ATP, is the immediate source of energy in muscle contraction. During rest, metabolic processes regenerate phosphocreatine stores. In normal muscle, ATP that is broken down to ADP is immediately rephosphorylated to ATP. Thus, phosphocreatine serves as a reservoir of ATP-synthesizing potential. phosphocreatine is the only fuel available to precipitously regenerate ATP during episodes of rapid fluctuations in demand. The availability of phosphocreatine likely limits muscle performance during brief, high-power exercise, i.e., maximal exercise of short duration. With near maximal isometric contraction, the rate of utilization of phosphocreatine declines after 1-2 seconds of contraction, prior to the glycolysis peak at approximately 3 seconds (PMID:10079702). Phosphocreatine undergoes irreversible cyclization and dehydration to form creatinine at a fractional rate of 0.026 per day, thus forming approximately 2 g creatinine/day in an adult male. This is the amount of creatine that must be provided either from dietary sources or by endogenous synthesis to maintain the body pool of (creatine and) phosphocreatine. Creatine is an amino acid that plays a vital role as phosphocreatine in regenerating adenosine triphosphate in skeletal muscle to energize muscle contraction. Creatine is phosphorylated to phosphocreatine in muscle in a reaction that is catalyzed by the enzyme creatine kinase. This enzyme is in highest concentration in muscle and nerve. Oral administration increases muscle stores. During the past decade, creatine has assumed prominence as an ergogenic (and legal) aid for professional and elite athletes. Most (~ 95\\%) of the total body creatine-phosphocreatine pool is in muscle (more in skeletal muscle than in smooth muscle) and amounts to 120 g (or 925 mmol) in a 70 kg adult male. Approximately 60-67\\% of the content in resting muscle is in the phosphorylated form. This generates enough ATP at the myofibrillar apparatus to power about 4 seconds of muscle contraction in exercise. Phosphocreatine reacts with ADP to yield ATP and creatine; the reversible reaction is catalyzed by creatine kinase. phosphocreatine is the chief store of high-energy phosphates in muscle. Thus, this reaction, which permits the rephosphorylation of ADP to ATP, is the immediate source of energy in muscle contraction. During rest, metabolic processes regenerate phosphocreatine stores. In normal muscle, ATP that is broken down to ADP is immediately rephosphorylated to ATP. Thus, phosphocreatine serves as a reservoir of ATP-synthesizing potential. phosphocreatine is the only fuel available to precipitously regenerate ATP during episodes of rapid fluctuations in demand. The availability of phosphocreatine likely limits muscle performance during brief, high-power exercise, i.e., maximal exercise of short duration. With near maximal isometric contraction, the rate of utilization of phosphocreatine declines after 1-2 seconds of contraction, prior to the glycolysis peak at approximately 3 seconds. (PMID: 10079702, Nutr Rev. 1999 Feb;57(2):45-50.) [HMDB] D020011 - Protective Agents > D002316 - Cardiotonic Agents C - Cardiovascular system > C01 - Cardiac therapy D002317 - Cardiovascular Agents KEIO_ID P084; [MS2] KO009218 KEIO_ID P084

Ciliatine

C2H8NO3P (125.0242)

Ciliatine is an organophosphorus compound isolated from human and animal tissues. [HMDB] Acquisition and generation of the data is financially supported in part by CREST/JST. Ciliatine is an organophosphorus compound isolated from human and animal tissues. KEIO_ID A056 (2-Aminoethyl)phosphonic acid is an endogenous metabolite.

Aniline

C6H7N (93.0578)

Aniline is a weak base. Aromatic amines such as aniline are, in general, much weaker bases than aliphatic amines. Aniline reacts with strong acids to form anilinium (or phenylammonium) ion (C6H5-NH3+). The sulfate forms beautiful white plates. Although aniline is weakly basic, it precipitates zinc, aluminium, and ferric salts, and, on warming, expels ammonia from its salts. The weak basicity is due to a negative inductive effect as the lone pair on the nitrogen is partially delocalised into the pi system of the benzene ring.; Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben , who named it crystalline. In 1834, Friedrich Runge (Pogg. Ann., 1834, 31, p. 65; 32, p. 331) isolated from coal tar a substance that produced a beautiful blue colour on treatment with chloride of lime, which he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that, by treating indigo with caustic potash, it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit n?la, dark-blue, and n?l?, the indigo plant. About the same time N. N. Zinin found that, on reducing nitrobenzene, a base was formed, which he named benzidam. August Wilhelm von Hofmann investigated these variously-prepared substances, and proved them to be identical (1855), and thenceforth they took their place as one body, under the name aniline or phenylamine.; Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals. Its main application is in the manufacture of polyurethane. Like most volatile amines, it possesses the somewhat unpleasant odour of rotten fish and also has a burning aromatic taste; it is a highly-acrid poison. It ignites readily, burning with a smoky flame.; Like phenols, aniline derivatives are highly susceptible to electrophilic substitution reactions. For example, reaction of aniline with sulfuric acid at 180 °C produces sulfanilic acid, NH2C6H4SO3H, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs that were widely used as antibacterials in the early 20th century.; The great commercial value of aniline was due to the readiness with which it yields, directly or indirectly, dyestuffs. The discovery of mauve in 1856 by William Henry Perkin was the first of a series of an enormous range of dyestuffs, such as fuchsine, safranine and induline. In addition to its use as a precursor to dyestuffs, it is a starting-product for the manufacture of many drugs, such as paracetamol (acetaminophen, Tylenol).; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th cent... Aniline is an organic chemical compound, specifically a primary aromatic amine. It consists of a benzene ring attached to an amino group. Aniline is oily and, although colorless, it can be slowly oxidized and resinified in air to form impurities which can give it a red-brown tint. Its boiling point is 184 degree centigrade and its melting point is -6 degree centegrade. It is a liquid at room temperature. Like most volatile amines, it possesses a somewhat unpleasant odour of rotten fish, and also has a burning aromatic taste; it is a highly acrid poison. It ignites readily, burning with a large smoky flame. Aniline reacts with strong acids to form salts containing the anilinium (or phenylammonium) ion (C6H5-NH3+), and reacts with acyl halides (such as acetyl chloride (ethanoyl chloride), CH3COCl) to form amides. The amides formed from aniline are sometimes called anilides, for example CH3-CO-NH-C6H5 is acetanilide, for which the modern name is N-phenyl ethanamide. Like phenols, aniline derivatives are highly reactive in electrophilic substitution reactions. For example, sulfonation of aniline produces sulfanilic acid, which can be converted to sulfanilamide. Sulfanilamide is one of the sulfa drugs which were widely used as antibacterial in the early 20th century. Aniline was first isolated from the destructive distillation of indigo in 1826 by Otto Unverdorben. In 1834, Friedrich Runge isolated from coal tar a substance which produced a beautiful blue color on treatment with chloride of lime; this he named kyanol or cyanol. In 1841, C. J. Fritzsche showed that by treating indigo with caustic potash it yielded an oil, which he named aniline, from the specific name of one of the indigo-yielding plants, Indigofera anil, anil being derived from the Sanskrit, dark-blue. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 8060 D009676 - Noxae > D002273 - Carcinogens KEIO_ID A054 KEIO_ID A162

Citrulline

C6H13N3O3 (175.0957)

Citrulline, also known as Cit or δ-ureidonorvaline, 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. Citrulline has the formula H2NC(O)NH(CH2)3CH(NH2)CO2H. Citrulline exists in all living species, ranging from bacteria to humans. Within humans, citrulline participates in a number of enzymatic reactions. In particular, citrulline can be biosynthesized from carbamoyl phosphate and ornithine which is catalyzed by the enzyme ornithine carbamoyltransferase. In addition, citrulline and L-aspartic acid can be converted into argininosuccinic acid through the action of the enzyme argininosuccinate synthase. In humans, citrulline is involved in the metabolic disorder called argininemia. Citrulline has also been found to be associated with several diseases such as ulcerative colitis, rheumatoid arthritis, and citrullinemia type II. Citrulline has also been linked to several inborn metabolic disorders including argininosuccinic aciduria and fumarase deficiency. Outside of the human body, citrulline is found, on average, in the highest concentration in a few different foods such as wheats, oats, and cucumbers and in a lower concentration in swiss chards, yellow wax beans, and potato. Citrulline has also been detected, but not quantified in several different foods, such as epazotes, lotus, common buckwheats, strawberry guava, and italian sweet red peppers. Citrulline is a potentially toxic compound. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation. Citrulline is also produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. It is also produced from arginine as a byproduct of the reaction catalyzed by NOS family (NOS; EC1.14.13.39). [Spectral] L-Citrulline (exact mass = 175.09569) and L-Glutamate (exact mass = 147.05316) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Occurs in the juice of watermelon (Citrullus vulgaris) IPB_RECORD: 257; CONFIDENCE confident structure KEIO_ID C013 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

Asymmetric dimethylarginine

C8H18N4O2 (202.143)

Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. It is a metabolic by-product of continual protein modification processes in the cytoplasm of all human cells. It is closely related to L-arginine, a conditionally-essential amino acid. ADMA interferes with L-arginine in the production of nitric oxide, a key chemical to endothelial and hence cardiovascular health. Asymmetric dimethylarginine is created in protein methylation, a common mechanism of post-translational protein modification. This reaction is catalyzed by an enzyme set called S-adenosylmethionine protein N-methyltransferases (protein methylases I and II). The methyl groups transferred to create ADMA are derived from the methyl group donor S-adenosylmethionine, an intermediate in the metabolism of homocysteine. (Homocysteine is an important blood chemical, because it is also a marker of cardiovascular disease). After synthesis, ADMA migrates into the extracellular space and thence into blood plasma. Asymmetric dimethylarginine is measured using high performance liquid chromatography. ADMA has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Isolated from broad bean seeds (Vicia faba). NG,NG-Dimethyl-L-arginine is found in many foods, some of which are yellow wax bean, spinach, green zucchini, and white cabbage. D004791 - Enzyme Inhibitors Asymmetric dimethylarginine is an endogenous inhibitor of nitric oxide synthase (NOS), and functions as a marker of endothelial dysfunction in a number of pathological states.

3-(Pyrazol-1-yl)-L-alanine

C6H9N3O2 (155.0695)

L-2-Amino-3-(1-pyrazolyl)propanoic acid is found in fruits. L-2-Amino-3-(1-pyrazolyl)propanoic acid is a amino acid present in seeds of Citrullus vulgaris (watermelon Amino acid present in seeds of Citrullus vulgaris (watermelon). L-2-Amino-3-(1-pyrazolyl)propanoic acid is found in fruits.

O-Phosphotyrosine

C9H12NO6P (261.0402)

O-Phosphotyrosine is a phosphorylated amino acid that occurs in a number of proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis. Small amounts of free phosphotyrosine can be found in urine (PMID: 7693088). Levels of this amino acid appear to be elevated in mammalian urine during liver regeneration (PMID: 7516161). Phosphotyrosine is also able to induce platelet aggregation in vitro and it has been suggested that free phosphotyrosine in blood could be meaningful for in vivo platelet activation (PMID: 1282059). [HMDB] O-Phosphotyrosine is a phosphorylated amino acid that occurs in a number of proteins. Tyrosine phosphorylation and dephosphorylation plays a role in cellular signal transduction and possibly in cell growth control and carcinogenesis. Small amounts of free phosphotyrosine can be found in urine (PMID: 7693088). Levels of this amino acid appear to be elevated in mammalian urine during liver regeneration (PMID: 7516161). Phosphotyrosine is also able to induce platelet aggregation in vitro and it has been suggested that free phosphotyrosine in blood could be meaningful for in vivo platelet activation (PMID: 1282059).

Nicotianamine

C12H21N3O6 (303.143)

The (S,S,S)-stereoisomer of nicotianamine. IPB_RECORD: 2921; CONFIDENCE confident structure

Pretyrosine

C10H13NO5 (227.0794)

O-Phosphohomoserine

C4H10NO6P (199.0246)

O-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. O-phosphohomoserine has been found in trace amounts in shotgun-metabolomics analysis in mouse tissue extracts, and is the substrate of a threonine analog enzyme in murine species. O-phosphohomoserine, an analogue of the excitatory amino acid antagonist 2-amino-phosphonovalerate is an N-methyl-D-aspartate (NMDA) antagonist. (PMID: 3528930, 17034760, 17665876) [HMDB] O-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. O-phosphohomoserine has been found in trace amounts in shotgun-metabolomics analysis in mouse tissue extracts, and is the substrate of a threonine analog enzyme in murine species. O-phosphohomoserine, an analogue of the excitatory amino acid antagonist 2-amino-phosphonovalerate is an N-methyl-D-aspartate (NMDA) antagonist. (PMID: 3528930, 17034760, 17665876).

4-Methylene-L-glutamine

C6H10N2O3 (158.0691)

Benzyl thiocyanate

C8H7NS (149.0299)

Benzyl thiocyanate is found in brassicas. Benzyl thiocyanate is isolated from Lepidium sativum (garden cress) as a benzyl glucosinolate (see Benzyl glucosinolate LBB34-N) degradation produce Isolated from Lepidium sativum (garden cress) as a benzyl glucosinolate (see Benzyl glucosinolate LBB34-N) degradation production Benzyl thiocyanate is found in garden cress and brassicas.

L-Aspartyl-4-phosphate

C4H8NO7P (213.0038)

L-Aspartyl-4-phosphate belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from a reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Aspartyl-4-phosphate is a very strong basic compound (based on its pKa). L-Aspartyl-4-phosphate is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. L-Aspartyl-4-phosphate is produced from a reaction between L-aspartate and ATP, with ADP as a byproduct. The reaction is catalyzed by aspartate kinase. L-Aspartyl-4-phosphate reacts with NADPH to produce phosphate, L-aspartate-semialdehyde, and NADP+. Aspartate-semialdehyde dehydrogenase catalyzes this reaction. L-Aspartyl-4-phosphate is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids

S-Ribosylhomocysteine

C9H17NO6S (267.0777)

S-(5-deoxy-beta-D-ribos-5-yl)-L-homocysteine is an S-(5-deoxy-D-ribos-5-yl)-L-homocysteine in which the anomeric centre has beta-configuration. It has a role as an Escherichia coli metabolite. It is functionally related to a L-homocysteine.

1-Pyrroline-2-carboxylic acid

C5H7NO2 (113.0477)

1-Pyrroline-2-carboxylic acid is a terminal product of D-proline metabolism. Specifically D-proline is converted to 1-Pyrroline-2-carboxylic acid via D-amino acid oxidase. This spontaneously breaks down to 2-oxo-5-amino-valerate. [HMDB] 1-Pyrroline-2-carboxylic acid is a terminal product of D-proline metabolism. Specifically D-proline is converted to 1-Pyrroline-2-carboxylic acid via D-amino acid oxidase. This spontaneously breaks down to 2-oxo-5-amino-valerate.

Glutamate-1-semialdehyde

C5H9NO3 (131.0582)

2-Amino-5-oxohexanoate

C6H11NO3 (145.0739)

4-hydroxy-4-methylglutamate

C6H11NO5 (177.0637)

A glutamic acid derivative that is L-glutamic acid with a methyl and a hydroxy group replacing the two hydrogens at position 4.

Deidaclin

C12H17NO6 (271.1056)

Sarmentosin

C11H17NO7 (275.1005)

Sarmentosin is found in fruits. Sarmentosin is isolated from Ribes nigrum (blackcurrant

Triglochinin

C14H17NO10 (359.0852)

Isotriglochinin is found in green vegetables. Isotriglochinin is a constituent of the famine food Alocasia macrorrhiza (wild taro). Constituent of the famine food Alocasia macrorrhiza (wild taro). Triglochinin is found in green vegetables.

Betalamic acid

C9H9NO5 (211.0481)

Betalamic acid is found in common beet. Betalamic acid is a precursor of betalains pigments in plants of the Centrospermae. Betalamic acid is detected in Beta vulgaris (beetroot Precursor of betalains pigments in plants of the Centrospermae. Detected in Beta vulgaris (beetroot). Betalamic acid is found in red beetroot, common beet, and root vegetables. D004396 - Coloring Agents > D050858 - Betalains

Chlorothalonil

C8Cl4N2 (263.8816)

D010575 - Pesticides > D008975 - Molluscacides D016573 - Agrochemicals

AminoDHS

C7H9NO4 (171.0532)

N,N-dihydroxy-L-tyrosine

C9H11NO5 (213.0637)

Homomethionine

C6H13NO2S (163.0667)

Homomethionine (CAS: 6094-76-4) 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 carboxylate group (alpha carbon). Homomethionine is possibly neutral. Homomethionine has been detected, but not quantified in, several different foods, such as lima beans, red huckleberries, catjang pea, Chinese chestnuts, and pepper (C. annuum). This could make homomethionine a potential biomarker for the consumption of these foods. Homomethionine is found in brassicas and is isolated from cabbage and horseradish. Isolated from cabbage and horseradish. L-2-Amino-5-(methylthio)pentanoic acid is found in many foods, some of which are pepper (c. frutescens), vanilla, cauliflower, and pineappple sage.

trihomomethionine

C8H17NO2S (191.098)

A sulfur-containing amino acid consisting of 2-aminoheptanoic acid having a methylthio substituent at the 7-position.

pentahomomethionine

C10H21NO2S (219.1293)

A sulfur-containing amino acid consisting of 2-aminononanoic acid having a methylthio substituent at the 9-position.

N,N-dihydroxy-L-isoleucine

C6H13NO4 (163.0845)

4-Aminohippuric acid

C9H10N2O3 (194.0691)

4-Aminohippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Renal proximal tubules secrete various organic anions, including drugs and p-aminohippurate (PAH). Uptake of PAH from blood into tubule cells occurs by exchange with intracellular alpha-ketoglutarate and is mediated by the organic anion transporter 1. PAH exit into tubule lumen is species specific and may involve ATP-independent and -dependent transporters. (PMID 11443229). Enhanced secretion of p-aminohippuric acid occurs in Fanconis syndrome (FS). FS is associated with numerous varieties of inherited and acquired conditions; FS is characterized by a generalized transport defect in the proximal tubules, leading to renal losses of glucose, phosphate, calcium, uric acid, amino acids, bicarbonates, and other organic compounds. (PMID 12552490). 4-Aminohippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CH - Tests for renal function and ureteral injuries D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents 4-Aminohippuric acid is a diagnostic agent used in renal testing and is used in the determination of renal plasma flow.

4-hydroxyglutamate

C5H9NO5 (163.0481)

4-Hydroxy-L-glutamic acid is an intermediate in the metabolism of gamma-hydroxyglutamic acid. Specifically 4-Hydroxy-L-glutamic acid combines with 2-oxoglutarate to produce 4-hydroxy-2-oxoglutarate and glutamate. The reaction can be described as: 4-Hydroxy-L-glutamate + 2-Oxoglutarate <=> 4-Hydroxy-2-oxoglutarate + L-Glutamate. This reaction is catalyzed by 4-hydroxyglutamate aminotransferase (PMID 13948827). [HMDB] 4-Hydroxy-L-glutamic acid is an intermediate in the metabolism of gamma-hydroxyglutamic acid. Specifically, 4-hydroxy-L-glutamic acid combines with 2-oxoglutarate to produce 4-hydroxy-2-oxoglutarate and glutamate. The reaction can be described as: 4-hydroxy-L-glutamate + 2-oxoglutarate <=> 4-hydroxy-2-oxoglutarate + L-glutamate. This reaction is catalyzed by 4-hydroxyglutamate aminotransferase (PMID: 13948827).

D-Glutamic acid

C5H9NO4 (147.0532)

There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9\\% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. D-Glutamic acid has been found to be a metabolite of Lactobacillus (PMID: 22754309). There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9\\% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. [HMDB] D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids KEIO_ID G005

D-Proline

C5H9NO2 (115.0633)

D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva (PMID: 16480744). These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity. (PMID: 1426150) [HMDB] D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva (PMID: 16480744). These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity (PMID: 1426150). (R)-pyrrolidine-2-carboxylic acid is an endogenous metabolite. (R)-pyrrolidine-2-carboxylic acid is an endogenous metabolite.

L-Allothreonine

C4H9NO3 (119.0582)

L-allothreonine is the L-enantiomer of allothreonine. It has a role as an Escherichia coli metabolite and a Saccharomyces cerevisiae metabolite. It is an enantiomer of a D-allothreonine. It is a tautomer of a L-allothreonine zwitterion. Allothreonine is the substrate of the enzyme Serine hydroxymethyltransferase1 (SHMT, EC 2.1.2.1), a human cytoplasmic mRNA binding protein. SHMT uses pyridoxal 5-phosphate (PLP) and tetrahydropteroylglutamate (H4PteGlu) as coenzymes and catalyzes the reversible interconversion of serine and glycine. In addition to these physiological reactions, SHMT also catalyzes, in the absence of H4PteGlu, the retroaldol cleavage of several 3-hydroxyamino acids, such as allothreonine. Allothreonine is a plant metabolite that appears in the human diet in variable concentrations depending on: plant species, physiological changes during plant growth, senescence, and reactions to environmental stress or to changes due to plant transformation (PMID:10858298, 10952545). Allothreonine is the substrate of the enzyme Serine hydroxymethyltransferase1 (SHMT, EC 2.1.2.1), a human cytoplasmic mRNA binding protein. SHMT uses pyridoxal 5-phosphate (PLP) and tetrahydropteroylglutamate (H4PteGlu) as coenzymes and catalyzes the reversible interconversion of serine and glycine. In addition to these physiological reactions, SHMT also catalyzes, in the absence of H4PteGlu, the retroaldol cleavage of several 3-hydroxyamino acids, such as allothreonine. Allothreonine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=144-98-9 (retrieved 2024-07-15) (CAS RN: 144-98-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). D-Allothreonine is the D type stereoisomer of Allothreonine. D-Allothreonine is a peptido-lipid derived from bacteria. D-Allothreonine, amide-linked to the D-galacturonic acid, is also a constituent in the polysaccharide[1][2]. L-Allothreonine (H-allo-Thr-OH) is an endogenous metabolite.

Sambunigrin

C14H17NO6 (295.1056)

Isolated from leaves of elderberry (Sambucus nigra) and from other plants. Sambunigrin is found in passion fruit, fruits, and black elderberry. Sambunigrin is found in black elderberry. Sambunigrin is isolated from leaves of elderberry (Sambucus nigra) and from other plant

(S)-4-Hydroxymandelonitrile

C8H7NO2 (149.0477)

(s)-4-hydroxymandelonitrile, also known as (2s)-hydroxy(4-hydroxyphenyl)acetonitrile, is a member of the class of compounds known as 1-hydroxy-2-unsubstituted benzenoids. 1-hydroxy-2-unsubstituted benzenoids are phenols that a unsubstituted at the 2-position (s)-4-hydroxymandelonitrile is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (s)-4-hydroxymandelonitrile can be found in a number of food items such as persian lime, common salsify, climbing bean, and vaccinium (blueberry, cranberry, huckleberry), which makes (s)-4-hydroxymandelonitrile a potential biomarker for the consumption of these food products. This compound belongs to the family of Benzyl Cyanides. These are organic compounds containing an acetonitrile with one hydrogen replaced by a phenyl group

cis-4-Hydroxy-D-proline

C5H9NO3 (131.0582)

cis-4-Hydroxy-D-proline belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from a reaction of proline at the amino group or the carboxyl group, or from the replacement of any hydrogen of glycine by a heteroatom. KEIO_ID H048 cis-4-Hydroxy-D-proline is a precursor of conformationally restricted PNA adenine monomer. cis-4-Hydroxy-D-proline can be used to study the specificity and kinetics of D-alanine dehydrogenase[1][2].

DL-2-Aminopropionic acid

C3H7NO2 (89.0477)

(alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein), also known as ALA or 2-Aminopropanoic acid, is classified as an alanine or an Alanine derivative. Alanines are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) is considered to be soluble (in water) and acidic. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) can be synthesized from propionic acid. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) can be synthesized into alanine derivative. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) is an odorless tasting compound found in Green bell peppers, Green zucchinis, Italian sweet red peppers, and Red bell peppers Dietary supplement, nutrient, sweetening flavour enhancer in pickling spice mixts. DL-alanine, an amino acid, is the racemic compound of L- and D-alanine. DL-alanine is employed both as a reducing and a capping agent, used with silver nitrate aqueous solutions for the production of nanoparticles. DL-alanine can be used for the research of transition metals chelation, such as Cu(II), Zn(II), Cd(11). DL-alanine, a sweetener, is classed together with glycine, and sodium saccharin. DL-alanine plays a key role in the glucose-alanine cycle between tissues and liver[1][2][3][4][5][6].

3-phospho-L-serine

C3H8NO6P (185.0089)

O-phospho-d-serine, also known as (2r)-2-amino-3-(phosphonooxy)propanoic acid, is a member of the class of compounds known as D-alpha-amino acids. D-alpha-amino acids are alpha amino acids which have the D-configuration of the alpha-carbon atom. O-phospho-d-serine is soluble (in water) and a moderately acidic compound (based on its pKa). O-phospho-d-serine can be found in a number of food items such as mugwort, rambutan, common persimmon, and ostrich fern, which makes O-phospho-d-serine a potential biomarker for the consumption of these food products. O-phospho-d-serine may be a unique E.coli metabolite.

oxfenicine

C8H9NO3 (167.0582)

C26170 - Protective Agent > C2079 - Cardioprotective Agent The L-enantiomer of 4-hydroxyphenylglycine. D004791 - Enzyme Inhibitors Same as: D05292 Oxfenicine (L-p-Hydroxyphenylglycine) is an orally active carnitine palmitoyltransferase-1 inhibitor. Oxfenicine inhibits the oxidation of fatty acid in heart. Oxfenicine protects heart from necrotic tissue damage during ischaemia[1][2].

3-Methylhistidine

C7H11N3O2 (169.0851)

3-Methylhistidine, also known as 3-MHis or 3MH, belongs to the class of organic compounds known as histidine and derivatives. 3MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. 3-Methylhistidine is also classified as a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. 3-Methylhistidine is generated from histidine residues found in proteins. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as pi-methylhistidine) or 3-methylhistidine (3MH; tau-methylhistidine), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine and other histidine-containing peptides such as anserine. In particular, older literature (mostly prior to the year 2000) designated anserine (Npi methylated) as beta-alanyl-N1-methyl-histidine, whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methyl-histidine. As a result, many papers published prior to the year 2000 incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really were referring to 3MH (PMID: 24137022). Histidine methylation on the 3- or tau site is mediated by the enzyme known as METTL18. METTL18 is a nuclear methyltransferase protein that contains a functional nuclear localization signal and accumulates in nucleoli. Urinary concentrations of 3-methylhistidine can be used as a biomarker for skeletal muscle protein breakdown in humans who have been subject to muscle injury (PMID: 16079625). 3-methylhistidine is formed by the posttranslational methylation of histidine residues of the main myofibrillar proteins actin and myosin. During protein catabolism, 3-methylhistidine is released but cannot be reutilized. Therefore, the plasma concentration and urine excretion of 3-methylhistidine are sensitive markers of myofibrillar protein degradation (PMID: 32235743). Approximately 75\\\% of 3-methylhistidine is estimated to originate from skeletal muscle (PMID: 32235743). In addition to the degradation of muscle proteins, the 3-methylhistidine level is affected by the degradation of intestinal proteins and meat intake. 3-Methylhistidine exists in all eukaryotes, ranging from yeast to humans. In humans, 3-methylhistidine is involved in methylhistidine metabolism. 3-Methylhistidine has been found to be associated with several diseases such as diabetes mellitus type 2, eosinophilic esophagitis, and kidney disease. The normal concentration of 3-methylhistidine in the urine of healthy adult humans has been detected and quantified in a range of 3.63–69.27 micromoles per millimole (umol/mmol) of creatinine, with most studies reporting the average urinary concentration between 15–20 umol/mmol of creatinine. The average concentration of 3-methylhistidine in human blood plasma has been detected and quantified at 2.85 micromolar (uM) with a range of 0.0–5.9 uM. As a general rule, urinary 1MH is associated with white meat intake (p< 0.001), whereas urinary 3MH is associated with red meat intake (p< 0.001) (PMID: 34091671). 3-Methyl-L-histidine is a biomarker for meat consumption, especially chicken. It is also a biomarker for the consumption of soy products.

2,4-Diaminobutyric acid

C4H10N2O2 (118.0742)

2,4-Diaminobutyric acid, also known as 2,4-diaminobutanoate or Dbu, 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 carboxylate group (alpha carbon). 2,4-Diaminobutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2,4-Diaminobutyric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2,4-Diaminobutyric acid has been detected, but not quantified in cow milk. This could make 2,4-diaminobutyric acid a potential biomarker for the consumption of these foods. 2,4-Diaminobutyric acid is a non-physiological, cationic amino acid analogue that is transported into cells by System A with potent antitumoral activity in vitro against human glioma cells, the result of the pronounced concentrated uptake of DAB in glioma cells to the extent that a cellular lysis could occur due to osmotic reasons. 2,4-Diaminobutyric acid is a non-physiological, cationic amino acid analogue that is transported into cells by System A with potent antitumoral activity in vitro against human glioma cells, the result of the pronounced concentrated uptake of DAB in glioma cells to the extent that a cellular lysis could occur due to osmotic reasons. (PMID: 1561943) [HMDB] L-DABA (L-2,4-Diaminobutyric acid) is a week GABA transaminase inhibitor with an IC50 of larger than 500 μM; exhibits antitumor activity in vivo and in vitro. L-DABA (L-2,4-Diaminobutyric acid) is a week GABA transaminase inhibitor with an IC50 of larger than 500 μM; exhibits antitumor activity in vivo and in vitro.

Thiiranebutanenitrile

C6H9NS (127.0456)

Thiiranebutanenitrile is found in brassicas. Thiiranebutanenitrile is a hydrolysis produced from seeds of Brassica campestri

Cappariloside A

C16H18N2O6 (334.1165)

Constituent of the fruit of Capparis spinosa (caper). Cappariloside A is found in capers and herbs and spices. Cappariloside A is found in capers. Cappariloside A is a constituent of the fruit of Capparis spinosa (caper)

(2S,3'S)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid

C9H14N2O5 (230.0903)

(2S,3S)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid is found in mushrooms. (2S,3S)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid is a amino acid from the basidiomycete Lactarius piperatus. Amino acid from the basidiomycete Lactarius piperatus. (2S,3S)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid is found in mushrooms.

Cappariloside B

C22H28N2O11 (496.1693)

Constituent of the fruit of Capparis spinosa (caper). Cappariloside B is found in capers and herbs and spices. Cappariloside B is found in capers. Cappariloside B is a constituent of the fruit of Capparis spinosa (caper)

(3R)-3,4-Dihydroxy-3-(hydroxymethyl)butanenitrile 4-glucoside

C11H19NO8 (293.1111)

(3R)-3,4-Dihydroxy-3-(hydroxymethyl)butanenitrile 4-glucoside is found in cereals and cereal products. (3R)-3,4-Dihydroxy-3-(hydroxymethyl)butanenitrile 4-glucoside is a constituent of barley (Hordeum vulgare). Constituent of barley (Hordeum vulgare). (3R)-3,4-Dihydroxy-3-(hydroxymethyl)butanenitrile 4-glucoside is found in barley and cereals and cereal products.

L-4-Chlorotryptophan

C11H11ClN2O2 (238.0509)

L-4-Chlorotryptophan is found in common pea. L-4-Chlorotryptophan is isolated from the seed protein of Pisum sativum (pea). Also obtained from the seeds of Vicia fab Isolated from the seed protein of Pisum sativum (pea)and is also obtained from the seeds of Vicia faba. 4-Chloro-L-tryptophan is found in pulses and common pea.

(2S,2'S)-Pyrosaccharopine

C11H18N2O5 (258.1216)

(2S,2S)-Pyrosaccharopine is found in cereals and cereal products. (2S,2S)-Pyrosaccharopine is isolated from edible dried shiitake mushroom (Lentinus edodes) and buckwheat seeds (Fagopyrum esculentum). Isolated from edible dried shiitake mushroom (Lentinus edodes) and buckwheat seeds (Fagopyrum esculentum). (2S,2S)-Pyrosaccharopine is found in mushrooms and cereals and cereal products.

Mandelonitrile sophoroside

C20H27NO11 (457.1584)

Mandelonitrile sophoroside is isolated from leaves of perilla (Perilla frutescens var. acuta). Isolated from leaves of perilla (Perilla frutescens variety acuta)

2-Amino-4-oxopentanoic acid

C5H9NO3 (131.0582)

5-hydroxylysine

C6H14N2O3 (162.1004)

3,3'-Diiodo-L-thyronine

C15H13I2NO4 (524.8934)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

3-Azetidinecarboxylic acid

C4H7NO2 (101.0477)

Cysteine sulfinic acid

C3H7NO4S (153.0096)

D-Citrulline

C6H13N3O3 (175.0957)

Citrullin, also known as cit or 2-amino-5-uredovaleric 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). Citrullin is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Citrullin can be found in a number of food items such as cow milk, sesame, orange bell pepper, and pepper (c. frutescens), which makes citrullin a potential biomarker for the consumption of these food products. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite. 2-Amino-5-ureidopentanoic acid is an endogenous metabolite.

Fipronil sulfone

C12H4Cl2F6N4O2S (451.9336)

D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018756 - GABA Antagonists D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals Fipronil sulfone is the major metabolite of Fipronil.Fipronil sulfone selectively inhibits GABA receptor with IC50 of 175 nM (assayed by displacement of 4′-ethynyl-4-n-[2,3-3H2]- propylbicycloorthobenzoate ([3H]EBOB) from the noncompetitive blocker site).

O-Succinyl-L-homoserine

C8H13NO6 (219.0743)

D-Alanyl glycine

C5H10N2O3 (146.0691)

D-alanyl glycine, also known as ag, is a member of the class of compounds known as dipeptides. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. D-alanyl glycine is slightly soluble (in water) and a weakly acidic compound (based on its pKa). D-alanyl glycine can be found in rice, which makes D-alanyl glycine a potential biomarker for the consumption of this food product.

Baikiain

C6H9NO2 (127.0633)

Baikiain, also known as 4,5-dehydropipecolic acid, (+-)-isomer, 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). Baikiain is soluble (in water) and a moderately acidic compound (based on its pKa). Baikiain can be found in date, which makes baikiain a potential biomarker for the consumption of this food product.

N,N-dihydroxy-L-tyrosine

C9H10NO5 (212.0559)

N,n-dihydroxy-l-tyrosine is slightly soluble (in water) and a weakly acidic compound (based on its pKa). N,n-dihydroxy-l-tyrosine can be found in a number of food items such as mentha (mint), bilberry, red raspberry, and oxheart cabbage, which makes n,n-dihydroxy-l-tyrosine a potential biomarker for the consumption of these food products.

creatine

C4H9N3O2 (131.0695)

Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

Arginine

C6H14N4O2 (174.1117)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

Citrulline

C6H13N3O3 (175.0957)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

Phenylalanine

C9H11NO2 (165.079)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

Dysiherbaine

C12H20N2O7 (304.127)

A furopyran that is (3aR,7aR)-hexahydro-2H-furo[3,2-b]pyran substituted by carboxy, (2S)-2-amino-2-carboxyethyl, hydroxy and methylamino groups at positions 2, 2, 6, and 7, respectively (the 2R,3aR,6S,7R,7aR-stereoisomer). A convulsant isolated from the marine sponge Dysidea herbacea that has high affinity for kainate ionotropic glutamate receptors.

4-Aminopyrrolidine-2-carboxylic acid

C5H10N2O2 (130.0742)

4-Aminoanthranilic acid

C7H8N2O2 (152.0586)

OXAMIC ACID

C2H3NO3 (89.0113)

A dicarboxylic acid monoamide resulting from the formal condensation of one of the carboxy groups of oxalic acid with ammonia.

2-amino-3-ethoxy-3-methylbutanoic acid

C7H15NO3 (161.1052)

3-Methylhistidine

C7H11N3O2 (169.0851)

A methylhistidine in which the methyl group is located at N-3. 3-Methyl-L-histidine is a biomarker for meat consumption, especially chicken. It is also a biomarker for the consumption of soy products.

Fipronil sulfone

C12H4Cl2F6N4O2S (451.9336)

D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018756 - GABA Antagonists D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals CONFIDENCE standard compound; INTERNAL_ID 2421 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 8846 CONFIDENCE standard compound; EAWAG_UCHEM_ID 2667 Fipronil sulfone is the major metabolite of Fipronil.Fipronil sulfone selectively inhibits GABA receptor with IC50 of 175 nM (assayed by displacement of 4′-ethynyl-4-n-[2,3-3H2]- propylbicycloorthobenzoate ([3H]EBOB) from the noncompetitive blocker site).

N-Methylisoleucine

C7H15NO2 (145.1103)

4-Hydroxy-L-glutamic acid

C5H9NO5 (163.0481)

An amino dicarboxylic acid that is L-glutamic acid substituted by a hydroxy group at position 4.

2-amino-4-hydroxypentanoic acid

C5H11NO3 (133.0739)

N-methyltaurine

C3H9NO3S (139.0303)

Formylaniline

C7H7NO (121.0528)

2-amino-3-hydroxy-3-methylbutanoic acid

C5H11NO3 (133.0739)

3-(methylamino)pentanedioic acid

C6H11NO4 (161.0688)

2-Amino-4,5-hexadienoic acid

C6H9NO2 (127.0633)

2,3-diaminobutanoic acid

C4H10N2O2 (118.0742)

tumonoic acid C

C27H45NO8 (511.3145)

A natural product found particularly in Oscillatoria margaritifera and Oscillatoria margaritifera.

methyl tumonoate B

C29H49NO8 (539.3458)

A natural product found particularly in Oscillatoria margaritifera and Oscillatoria margaritifera.

methyl tumonoate A

C20H35NO4 (353.2566)

A natural product found particularly in Oscillatoria margaritifera and Oscillatoria margaritifera.

2-amino-3-(hydroxymethyl)pent-3-enoic acid

C6H11NO3 (145.0739)

ethyl tumonoate A

C21H37NO4 (367.2722)

A natural product found particularly in Oscillatoria margaritifera and Oscillatoria margaritifera.

Triglochinin

C14H17NO10 (359.0852)

2-amino-3-cyclopropylpropanoic acid

C6H11NO2 (129.079)

mycalenitrile-4

C29H46N2O (438.361)

Phenylalanine

C9H11NO2 (165.079)

An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group. Annotation level-2 Acquisition and generation of the data is financially supported by the Max-Planck-Society COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS IPB_RECORD: 2701; CONFIDENCE confident structure L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

5-hydroxylysine

C6H14N2O3 (162.1004)

The lysine derivative that is 2,6-diamino-5-hydroxyhexanoic acid, a chiral alpha-amino acid. KEIO_ID H064

Citrulline

C6H13N3O3 (175.0957)

The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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 CONFIDENCE standard compound; ML_ID 29 L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway. L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

Arginine

C6H14N4O2 (174.1117)

An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.047 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.045 Acquisition and generation of the data is financially supported by the Max-Planck-Society L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

Mimosine

C8H10N2O4 (198.0641)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.056 Mimosine, a tyrosine analog , can act as an antioxidant by its potent iron-binding activity[1]. Mimosine is a known chelator of Fe(III)[2]. Mimosine induces apoptosis through metal ion chelation, mitochondrial activation and ROS production in human leukemic cells[3]. Anti-cancer, antiinflammation. Mimosine, a tyrosine analog , can act as an antioxidant by its potent iron-binding activity[1]. Mimosine is a known chelator of Fe(III)[2]. Mimosine induces apoptosis through metal ion chelation, mitochondrial activation and ROS production in human leukemic cells[3]. Anti-cancer, antiinflammation.

creatine

C4H9N3O2 (131.0695)

A glycine derivative having methyl and amidino groups attached to the nitrogen. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; CVSVTCORWBXHQV-UHFFFAOYSA-N_STSL_0071_Creatine_8000fmol_180416_S2_LC02_MS02_77; 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. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain. Creatine, an endogenous amino acid derivative, plays an important role in cellular energy, especially in muscle and brain.

O-Succinyl-L-homoserine

C8H13NO6 (219.0743)

The O-succinyl derivative of L-homoserine.

(2-Aminoethyl)phosphonate

C2H8NO3P (125.0242)

(2-Aminoethyl)phosphonic acid is an endogenous metabolite.

1-Aminocyclopropane-1-carboxylate

C4H7NO2 (101.0477)

1-Aminocyclopropane-1-carboxylic acid is an endogenous metabolite.

L-Cystathionine

C7H14N2O4S (222.0674)

A modified amino acid generated by enzymic means from L-homocysteine and L-serine. L-Cystathionine is a nonprotein thioether and is a key amino acid associated with the metabolic state of sulfur-containing amino acids. L-Cystathionine protects against Homocysteine-induced mitochondria-dependent apoptosis of vascular endothelial cells (HUVECs). L-Cystathionine plays an important role in cardiovascular protection[1][2]. L-Cystathionine is a nonprotein thioether and is a key amino acid associated with the metabolic state of sulfur-containing amino acids. L-Cystathionine protects against Homocysteine-induced mitochondria-dependent apoptosis of vascular endothelial cells (HUVECs). L-Cystathionine plays an important role in cardiovascular protection[1][2].

L-Histidine

C6H9N3O2 (155.0695)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; HNDVDQJCIGZPNO_STSL_0107_Histidine_8000fmol_180430_S2_LC02_MS02_142; 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. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport. L-Histidine is an essential amino acid for infants. L-Histidine is an inhibitor of mitochondrial glutamine transport.

Phosphocreatine

C4H10N3O5P (211.0358)

D020011 - Protective Agents > D002316 - Cardiotonic Agents C - Cardiovascular system > C01 - Cardiac therapy D002317 - Cardiovascular Agents

Guanidinosuccinic acid

C5H9N3O4 (175.0593)

Guanidinosuccinic acid is a nitrogenous metabolite.

L-Allothreonine

C4H9NO3 (119.0582)

The L-enantiomer of allothreonine. L-Allothreonine (H-allo-Thr-OH) is an endogenous metabolite.

Homocystine

C8H16N2O4S2 (268.0551)

An organic disulfide obtained by oxidative dimerisation of homocysteine. 4,4'-Disulfanediylbis(2-aminobutanoic acid) is an endogenous metabolite.

4-Aminobenzoate

C7H7NO2 (137.0477)

4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi. 4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi.

1-Aminocyclopropane-1-carboxylic acid

C4H7NO2 (101.0477)

1-Aminocyclopropane-1-carboxylic acid is an endogenous metabolite.

L-Phenylalanine

C9H11NO2 (165.079)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; COLNVLDHVKWLRT_STSL_0103_Phenylalanine_2000fmol_180506_S2_LC02_MS02_290; 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. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4]. L-Phenylalanine ((S)-2-Amino-3-phenylpropionic acid) is an essential amino acid isolated from Escherichia coli. L-Phenylalanine is a α2δ subunit of voltage-dependent Ca+ channels antagonist with a Ki of 980 nM. L-phenylalanine is a competitive antagonist for the glycine- and glutamate-binding sites of N-methyl-D-aspartate receptors (NMDARs) (KB of 573 μM ) and non-NMDARs, respectively. L-Phenylalanine is widely used in the production of food flavors and pharmaceuticals[1][2][3][4].

L-Tyrosine

C9H11NO3 (181.0739)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OUYCCCASQSFEME-QMMMGPOBSA-N_STSL_0110_L-Tyrosine_0500fmol_180506_S2_LC02_MS02_57; 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. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

4-Aminobenzoic acid

C7H7NO2 (137.0477)

D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BA - Protectives against uv-radiation for topical use An aminobenzoic acid in which the amino group is para to the carboxy group. 4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi. 4-Aminobenzoic acid is an intermediate in the synthesis of folic acid by bacteria, plants and fungi.

2-Aminoethylphosphonic acid

C2H8NO3P (125.0242)

(2-Aminoethyl)phosphonic acid is an endogenous metabolite.

ANILINE

C6H7N (93.0578)

D009676 - Noxae > D002273 - Carcinogens

O-Acetyl-L-serine

C5H9NO4 (147.0532)

An acetyl-L-serine where the acetyl group is attached to the side-chain oxygen. It is an intermediate in the biosynthesis of the amino acid cysteine in bacteria. O-Acetylserine (O-Acetyl-L-serine) is an intermediate in the biosynthesis of the amino acid cysteine in bacteria and plants. O-Acetyl-L-serine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=5147-00-2 (retrieved 2024-09-27) (CAS RN: 5147-00-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

L-Homocysteine

C4H9NO2S (135.0354)

A homocysteine that has L configuration. L-Homocysteine, a homocysteine metabolite, is a homocysteine that has L configuration. L-Homocysteine induces upregulation of cathepsin V that mediates vascular endothelial inflammation in hyperhomocysteinaemia[1][2].

Alanine

C3H7NO2 (89.0477)

An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2. Alanine (symbol Ala or A),[4] or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a nonpolar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as −NH + 3 ) and its carboxyl group deprotonated (as −CO − 2 ). It is non-essential to humans as it can be synthesized metabolically and does not need to be present in the diet. It is encoded by all codons starting with GC (GCU, GCC, GCA, and GCG). The L-isomer of alanine (left-handed) is the one that is incorporated into proteins. L-alanine is second only to L-leucine in rate of occurrence, accounting for 7.8\\\\\% of the primary structure in a sample of 1,150 proteins.[5] The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls[6]: 131  (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

3-Hydroxyanthranilic acid

C7H7NO3 (153.0426)

An aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan. D000975 - Antioxidants > D016166 - Free Radical Scavengers D020011 - Protective Agents > D000975 - Antioxidants MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; WJXSWCUQABXPFS-UHFFFAOYSA-N_STSL_0003_3-hydroxyanthranillic acid_8000fmol_180416_S2_LC02_MS02_37; 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. 3-Hydroxyanthranilic acid is a tryptophan metabolite in the kynurenine pathway.

2,4-Diaminobutyric acid

C4H10N2O2 (118.0742)

A diamino acid that is butyric acid in which a hydrogen at position 2 and a hydrogen at position 4 are replaced by amino groups.

2,6-Diaminopimelic acid

C7H14N2O4 (190.0954)

The amino dicarboxylic acid that is heptanedioic acid with amino substituents at C-2 and C-6. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; GMKMEZVLHJARHF-UHFFFAOYSA-N_STSL_0247_26-diaminopimelic_acid_4000fmol_190413_S2_LC02MS02_053; 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. 2,6-Diaminoheptanedioic acid is an endogenous metabolite.

4-Aminobenzoic acid

C7H6NO2 (136.0399)

O-Acetylserine

C5H9NO4 (147.0532)

O-succinylhomoserine

C8H13NO6 (219.0743)

(2-Aminoethyl)phosphonic acid

C2H8NO3P (125.0242)

A phosphonic acid in which the hydrogen attached to the phosphorus of phosphonic acid is substituted by a 2-aminoethyl group. (2-Aminoethyl)phosphonic acid is an endogenous metabolite.

4-Hydroxy-L-proline

C5H9NO3 (131.0582)

The L-stereoisomer of 4-hydroxyproline.

cis-4-Hydroxy-D-proline

C5H9NO3 (131.0582)

Asymmetric dimethylarginine

C8H18N4O2 (202.143)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; YDGMGEXADBMOMJ_STSL_0134_Asymmetric dimethylarginine_0500fmol_180430_S2_LC02_MS02_41; 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.

Ciliatine

C2H8NO3P (125.0242)

2,6-Diaminoheptanedioic acid

C7H14N2O4 (190.0954)

4-Fluorothreonine

C4H8FNO3 (137.0488)

Toyocamycin

C12H13N5O4 (291.0967)

An N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents Toyocamycin (Vengicide) is an adenosine analog produced by Streptomyces diastatochromogenes, acts as an XBP1 inhibitor. Toyocamycin blocks RNA synthesis and ribosome function, and induces apoptosis. Toyocamycin affects IRE1α-XBP1 pathway, and inhibits XBP1 mRNA cleavage with an IC50 value of 80 nM with affecting IRE1α auto-phosphorylation. Toyocamycin specifically inhibits CDK9 with an IC50 value of 79 nM[1][2][3].

L-4-Chlorotryptophan

C11H11ClN2O2 (238.0509)

Thiiranebutanenitrile

C6H9NS (127.0456)

Selenomethyl selenocysteine

C4H9NO2Se (182.9798)

Selenomethionine 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 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. One is the transsulfuration pathway via selenocystathionine to produce selenocysteine, which in turn is degraded to H2Se by the enzyme b-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, 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. Selenomethyl selenocysteine is found in garden onion.

(3R)-3,4-Dihydroxy-3-(hydroxymethyl)butanenitrile 4-glucoside

C11H19NO8 (293.1111)

L-CCG-I

C6H9NO4 (159.0532)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists

Cappariloside A

C16H18N2O6 (334.1165)

Cappariloside B

C22H28N2O11 (496.1693)

Thiiranepropanenitrile

C5H7NS (113.0299)

Mandelonitrile sophoroside

C20H27NO11 (457.1584)

oxalyldiaminopropionic acid

C5H8N2O5 (176.0433)

(2S,2'S)-Pyrosaccharopine

C11H18N2O5 (258.1216)

1-(3-amino-3-carboxypropyl)-5-oxopyrrolidine-2-carboxylic acid

C9H14N2O5 (230.0903)

2-amino-3,4-dihydroxybutanoic acid

C4H9NO4 (135.0532)

2-Amino-4-oxopentanoic acid

C5H9NO3 (131.0582)

A derivative of valeric acid having amino and oxo substituents at the 2- and 4-positions respectively.

3-Hydroxy-L-valine

C5H11NO3 (133.0739)

A hydroxy-L-valine which carries a hydroxy group at position 3.

4-Amino-L-phenylalanine

C9H12N2O2 (180.0899)

4-Hydrazinylbenzoic acid

C7H8N2O2 (152.0586)

Hydroxyethylcysteine

C5H11NO3S (165.046)

(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid

C15H13I2NO4 (524.8934)

3-Cyanoindole

C9H6N2 (142.0531)

2-aminopentanedioic acid

C5H9NO4 (147.0532)

(2S)-2-Aminoheptanedioic acid

C7H13NO4 (175.0845)

Aviglycine

C6H12N2O3 (160.0848)

4-Hydroxybutanenitrile

C4H7NO (85.0528)

3-(1H-indol-3-yl)-2-(methylamino)propanoic acid

C12H14N2O2 (218.1055)

2-Amino-5-(methylsulfanyl)pentanoic acid

C6H13NO2S (163.0667)

2-amino-3-(1-methyl-1H-imidazol-4-yl)propanoic acid

C7H11N3O2 (169.0851)

2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid

C7H11N3O2 (169.0851)

Ovothiol B

C8H13N3O2S (215.0728)

A L-histidine derivative that is N-methyl-L-histidine substituted at positions N3 and C5 on the imidazole ring by methyl and mercapto groups respectively.

p-Aminophenylalanine

C9H12N2O2 (180.0899)

N,N-dihydroxy-L-tyrosine

C9H11NO5 (213.0637)

(5R,6R)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid

C7H9NO3 (155.0582)

cis-3-Hydroxy-D-proline

C5H9NO3 (131.0582)

A D-proline derivative that is D-proline monohydroxylated at position 3 (the cis-3-hydroxy-diastereomer).

N(5)-Hydroxy-L-arginine

C6H14N4O3 (190.1066)

Taxiphyllin

C14H17NO7 (311.1005)

(R)-4-hydroxymandelonitrile beta-D-glucoside is a beta-D-glucoside consisting of (R)-prunasin carrying a hydroxy substituent at position 4 on the phenyl ring. It is a beta-D-glucoside and a nitrile. It is functionally related to a (R)-prunasin. Taxiphyllin is a natural product found in Girgensohnia oppositiflora, Caroxylon tetrandrum, and other organisms with data available.

CYCLOHEXANECARBOXYLIC ACID

C7H12O2 (128.0837)

Cyclohexanecarboxylic acid is a Valproate structural analogue with anticonvulsant action[1].

D-Glutamic acid

C5H9NO4 (147.0532)

D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids An optically active form of glutamic acid having D-configuration.

D-Proline

C5H9NO2 (115.0633)

The D-enantiomer of proline. (R)-pyrrolidine-2-carboxylic acid is an endogenous metabolite. (R)-pyrrolidine-2-carboxylic acid is an endogenous metabolite.

Benzyl thiocyanate

C8H7NS (149.0299)

1-Aminocyclopropanecarboxylic acid

C4H7NO2 (101.0477)

A non-proteinogenic alpha-amino acid consisting of cyclopropane having amino and carboxy substituents both at the 1-position. D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents D020011 - Protective Agents 1-Aminocyclopropane-1-carboxylic acid is an endogenous metabolite.

Hypoglycin a

C7H11NO2 (141.079)

A diastereoisomeric mixture of (2S,4R)- and (2S,4S)- hypoglycin A, found in the edible part of the fruit of the Ackee, Blighia sapida (where the 2S,4R diastereoisomer is more dominant (17\\% d.e.) than its 2S,4S counterpart) as well as in the sycamore maple tree (Acer pseudoplatanus). D009676 - Noxae > D011042 - Poisons > D007005 - Hypoglycins

1-Pyrroline-2-carboxylic acid

C5H7NO2 (113.0477)

The product resulting from formal oxidation of DL-proline by loss of hydrogen from the nitrogen and from the carbon alpha to the carboxylic acid, with the formation of a C=N bond.

(2S,4R)-2-Amino-4-hydroxypentanedioic acid

C5H9NO5 (163.0481)

O-Phosphohomoserine

C4H10NO6P (199.0246)

Aspartyl phosphate

C4H8NO7P (213.0038)

D018377 - Neurotransmitter Agents > D018846 - Excitatory Amino Acids

(S)-4-Hydroxymandelonitrile

C8H7NO2 (149.0477)

4-Methylene-L-glutamic acid

C6H9NO4 (159.0532)

The L-enantiomer of 4-methyleneglutamic acid.

(2S,4S)-4-amino-2-hydroxy-2-methylpentanedioic acid

C6H11NO5 (177.0637)

O-Phospho-D-Serine

C3H8NO6P (185.0089)

The D-enantiomer of O-phosphoserine.

Betalamic acid

C9H9NO5 (211.0481)

D004396 - Coloring Agents > D050858 - Betalains

Sarmentosin

C11H17NO7 (275.1005)

N,N-dihydroxy-L-isoleucine

C6H13NO4 (163.0845)

An N,N-dihydroxy amino acid that is derived from L-isoleucine.

4-Methylene-L-glutamine

C6H10N2O3 (158.0691)

A non-proteinogenic L-alpha-amino acid that is L-glutamine in which the hydrogens attached to the carbon gamma to the carboxy group are replaced by a methylene group.

2-amino-5-oxohexanoic acid

C6H11NO3 (145.0739)

L-Thioproline

C4H7NO2S (133.0197)

An optically active version of thioproline having L-configuration.

2-amino-3-(4-chloro-1H-indol-3-yl)propanoic acid

C11H11ClN2O2 (238.0509)

4-(hydroxymethyl)benzenediazonium

C7H7N2O+ (135.0558)

2-amino-4-hydroxypentanedioic acid

C5H9NO5 (163.0481)

homomethionine

C6H13NO2S (163.0667)

N-Amidino-L-aspartic acid

C5H9N3O4 (175.0593)

An aspartic acid derivative comprising L-aspartic acid carrying an N-amidino substituent.

(S)-Prunasin

C14H17NO6 (295.1056)

Se-Methylselenocysteine

C4H9NO2Se (182.9798)

An alpha-amino acid compound having methylselanylmethyl as the side-chain.

2-Aminopimelic acid

C7H13NO4 (175.0845)

An amino dicarboxylic acid that is heptanedioic acid in which a hydrogen at position 2 is replaced by an amino group. It is a component of the cell wall peptidoglycan of bacteria.

β-methylamino L-alanine

C4H10N2O2 (118.0742)

beta-Methylamino-L-alanine 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 carboxylate group (alpha carbon). Based on a literature review very few articles have been published on beta-Methylamino-L-alanine.

(2s)-2-({[(2s)-1-[(2r)-3-(dihydroxycarbonimidoyl)-2-propylpropanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-methylbutanoic acid

C17H29N3O6 (371.2056)

(2r,4s)-4-hydroxypiperidine-2-carboxylic acid

C6H11NO3 (145.0739)

2-phenyl-2-{[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}acetonitrile

C14H17NO6 (295.1056)

4-amino-2-hydroxybutane-1,2,4-tricarboxylic acid

C7H11NO7 (221.0535)

(1s,2z,3r,5s,6s)-2-(cyanomethylidene)-5,6-dihydroxy-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl benzoate

C21H25NO10 (451.1478)

2-amino-4-{[(hydroxymethylidene)amino]oxy}but-3-enoic acid

C5H8N2O4 (160.0484)

n-(3-formyl-4-hydroxyphenyl)ethanehydrazonic acid

C9H10N2O3 (194.0691)

(2s)-2-amino-5-{[hydroxy(phenyl)methylidene]amino}pentanoic acid

C12H16N2O3 (236.1161)

(2s)-1-[(2r)-2-methyldecanoyl]pyrrolidine-2-carboxylic acid

C16H29NO3 (283.2147)

(2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid

C8H14N2O4 (202.0954)

(2s)-2-{[(3r)-3-amino-6-{[(1s)-1-carboxy-2-phenylethyl]-c-hydroxycarbonimidoyl}-1-hydroxyhexylidene]amino}-3-phenylpropanoic acid

C25H31N3O6 (469.2213)

2-amino-4-{[2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C13H18N2O4 (266.1267)

2-[(2s)-thiiran-2-yl]acetonitrile

C4H5NS (99.0143)

(1r,4s)-4-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

C12H17NO7 (287.1005)

4-(4-bromo-1h-pyrrole-2-carbonyloxy)piperidine-2-carboxylic acid

C11H13BrN2O4 (316.0059)

4-(c-hydroxycarbonimidoylamino)butanoic acid

C5H10N2O3 (146.0691)

(2s,4s)-2-amino-4-hydroxy-5-(c-hydroxycarbonimidoylamino)pentanoic acid

C6H13N3O4 (191.0906)

(6z,9z)-20-(5-formyl-1h-pyrrol-2-yl)icosa-6,9-dienenitrile

C25H38N2O (382.2984)

(2s,4r)-2-amino-4-hydroxyheptanedioic acid

C7H13NO5 (191.0794)

(2z)-2-(3-carbamimidamidopropylidene)butanedioic acid

C8H13N3O4 (215.0906)

methyl 2-[n-hydroxy-2-(n-hydroxyimino)propanamido]-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}propanoate

C18H24N2O6 (364.1634)

(2s)-2-amino-4-{[(1s)-1-carboxy-2-phenylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C14H18N2O5 (294.1216)

(2r,3ar,6r,7r,7ar)-2-[(2s)-2-amino-2-carboxyethyl]-6,7-dihydroxy-hexahydrofuro[3,2-b]pyran-2-carboxylic acid

C11H17NO8 (291.0954)

(2s)-2-amino-3-(cyclohexa-2,4-dien-1-yl)propanoic acid

C9H13NO2 (167.0946)

2-(n-hydroxyimino)-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}propanamide

C14H18N2O3 (262.1317)

4-[cyano({[(1s,2r,3r,4r,5s,6s)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})methylidene]hex-2-enedioic acid

C14H17NO10 (359.0852)

(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid

C8H15N3O4 (217.1063)

4-amino-2-(carboxyformamido)butanoic acid

C6H10N2O5 (190.059)

(2s)-1-methoxy-1-oxopropan-2-yl (2r,3s)-2-[(2s)-1-[(2r,4e)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylpentanoate

C29H49NO8 (539.3458)

(2s)-2-amino-3-methylidenepentanoic acid

C6H11NO2 (129.079)

(2r)-2-amino-3-(carboxymethyl-c-hydroxycarbonimidoyl)propanoic acid

C6H10N2O5 (190.059)

(2s)-2-amino-3-[7-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]propanoic acid

C16H20N2O2 (272.1525)

2-[(1z)-4-hydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-ylidene]acetonitrile

C14H19NO7 (313.1161)

3-cyano-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)prop-2-en-1-yl 3-(4-hydroxyphenyl)prop-2-enoate

C20H23NO9 (421.1373)

(3s)-2-acetyl-3-aminobutanedioic acid; oxindole

C14H16N2O6 (308.1008)

(2r)-2-amino-4-{[(1s)-2-carboxy-1-phenylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C14H18N2O5 (294.1216)

(2s)-2-amino-n-[hydroxy(methoxy)phosphoryl]-n,4-dimethylpentanehydrazonic acid

C8H20N3O4P (253.1191)

2-amino-3-[n-hydroxy-(c-hydroxycarbonimidoyl)amino]propanoic acid

C4H9N3O4 (163.0593)

(2s)-4-[(1e)-2-[(2s)-2-carboxypyrrolidin-1-yl]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid

C14H16N2O6 (308.1008)

(2s)-2-{[(2s,3r)-2-amino-1,3-dihydroxybutylidene]amino}-3-hydroxypropanoic acid

C7H14N2O5 (206.0903)

4-(sulfooxy)piperidine-2-carboxylic acid

C6H11NO6S (225.0307)

2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h-indol-3-yl)acetonitrile

C16H18N2O6 (334.1165)

1-{3-[(3-amino-3-carboxy-2-hydroxypropyl)amino]-3-carboxypropyl}azetidine-2-carboxylic acid

C12H21N3O7 (319.1379)

1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid

C6H12N4O2 (172.096)

(2s)-2-amino-3-(5-oxo-1,2-oxazolidin-2-yl)propanoic acid

C6H10N2O4 (174.0641)

(2s)-2-amino-4-{[(1s)-1-carboxyethyl]-c-hydroxycarbonimidoyl}butanoic acid

C8H14N2O5 (218.0903)

1-[3-(acetyloxy)-2,4-dimethyldodecanoyl]pyrrolidine-2-carboxylic acid

C21H37NO5 (383.2672)

(2s)-2-amino-4-{[(1s)-1-carboxy-2-[(1s)-2-methylidenecyclopropyl]ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C12H18N2O5 (270.1216)

2-[2,4-dihydroxy-3,6-bis({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})cyclohexylidene]acetonitrile

C20H31NO14 (509.1744)

(2s)-2-amino-4-{[2-(5-oxo-1,2-oxazol-2-yl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C10H15N3O5 (257.1012)

(2s)-2-amino-3-(1h-indol-2-yl)propanoic acid

C11H12N2O2 (204.0899)

2-amino-4-({2-disulfanyl-1-[(c-hydroxycarbonimidoylmethyl)-c-hydroxycarbonimidoyl]ethyl}-c-hydroxycarbonimidoyl)butanoic acid

C10H18N4O5S2 (338.0719)

(2s)-6-amino-2-[(1-hydroxyethylidene)amino]hexanoic acid

C8H16N2O3 (188.1161)

(2r)-2-({[(2s)-2-amino-1-hydroxy-3-methylbutylidene]amino}oxy)butanedioic acid

C9H16N2O6 (248.1008)

(2s,3r,4s)-2-amino-3-hydroxy-4-methylpentanedioic acid

C6H11NO5 (177.0637)

(2s)-2-amino-3-(4-chloro-1h-indol-3-yl)propanoic acid

C11H11ClN2O2 (238.0509)

2-cyanothiophene

C5H3NS (108.9986)

(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid

C7H13N3O4 (203.0906)

(1s,4s,5s)-4,5-dihydroxy-2-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

C12H17NO8 (303.0954)

(1s,2s,4r,5s)-4-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.1.0]hexane-2-carbonitrile

C12H17NO8 (303.0954)

(2s)-2-{[(2s)-2-amino-1-hydroxy-3-methylbutylidene]amino}-3-hydroxypropanoic acid

C8H16N2O4 (204.111)

(2s)-2-amino-3-(5-oxo-1,2-oxazol-2-yl)propanoic acid

C6H8N2O4 (172.0484)

3-methyl-2-({3-methyl-2-[1-(2-methyldecanoyl)pyrrolidine-2-carbonyloxy]butanoyl}oxy)butanoic acid

C26H45NO7 (483.3196)

(2s)-2-{[(2r)-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-3-{[cyano(1h-indol-3-yl)methyl]sulfanyl}-1-hydroxypropylidene]amino}pentanedioic acid

C23H27N5O8S (533.158)

n-[(1z,3z)-3-cyano-1-(3,4-dihydroxyphenyl)-3-[(3,4-dihydroxyphenyl)methylidene]prop-1-en-2-yl]carboximidic acid

C18H14N2O5 (338.0903)

(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}-3-(c-hydroxycarbonimidoyl)propanoic acid

C13H17N3O4 (279.1219)

(2r,4r)-4-(4-bromo-1h-pyrrole-2-carbonyloxy)piperidine-2-carboxylic acid

C11H13BrN2O4 (316.0059)

o-[4-(2-amino-1-hydroxyethyl)-2,6-dibromophenyl]carbamoyl cyanide

C13H15Br2N3O3 (418.948)

(2e)-2-cyano-2-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)ethyl 4-hydroxybenzoate

C18H21NO9 (395.1216)

2-amino-4-methylpentanedioic acid

C6H11NO4 (161.0688)

(2s,5s)-2-amino-5-hydroxyhexanoic acid

C6H13NO3 (147.0895)

(2s)-2-amino-4-[(3,4-dihydroxyphenyl)-c-hydroxycarbonimidoyl]butanoic acid

C11H14N2O5 (254.0903)

(2e)-3-cyano-2-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)prop-2-en-1-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C20H23NO9 (421.1373)

2-cyano-2-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)ethyl 4-hydroxybenzoate

C18H21NO9 (395.1216)

(2s,5s)-2-amino-5-hydroxyheptanedioic acid

C7H13NO5 (191.0794)

{6-[cyano(phenyl)methoxy]-4,5-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

C28H25NO14 (599.1275)

(2r,3s)-1-amino-3-hydroxy-2-methylcyclobutane-1-carboxylic acid

C6H11NO3 (145.0739)

2-{[2-({2-amino-1-hydroxy-4-[methyl(oxo)(phosphonoimino)-λ⁶-sulfanyl]butylidene}amino)-1-hydroxypropylidene]amino}propanoic acid

C11H23N4O8PS (402.0974)

(.+-.)-tyrosine

C9H11NO3 (181.0739)

2-amino-4-{5-hydroxy-2-[(hydroxymethylidene)amino]phenyl}-4-oxobutanoic acid

C11H12N2O5 (252.0746)

[(2r,3s,4s,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C23H23NO10 (473.1322)

2-amino-3-(1h-indol-2-yl)propanoic acid

C11H12N2O2 (204.0899)

(2s)-4-{2-[(2s)-2-carboxypyrrolidin-1-yl]ethenyl}-2,3-dihydropyridine-2,6-dicarboxylic acid

C14H16N2O6 (308.1008)

(2e)-2-(hydroxymethyl)-4-{[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-enenitrile

C11H17NO7 (275.1005)

(2z,3z)-bis[(4-hydroxyphenyl)methylidene]butanedinitrile

C18H12N2O2 (288.0899)

(2s)-2-amino-3-(1h-imidazol-2-yl)propanoic acid

C6H9N3O2 (155.0695)

(2s)-2-amino-4-{[(1r)-1-carboxy-2-(prop-2-en-1-yldisulfanyl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C11H18N2O5S2 (322.0657)

2-amino-3-(4-chloro-3h-indol-3-yl)propanoic acid

C11H11ClN2O2 (238.0509)

(2r)-2-phenyl-2-{[(2r,3s,4r,5r,6r)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}acetonitrile

C14H17NO6 (295.1056)

3-[({5,10-dihydroxy-4,9-dimethoxy-6-oxo-7h,8h,9h,11h-cyclohexa[b]fluoren-2-yl}methyl)sulfanyl]-2-[(1-hydroxyethylidene)amino]propanoic acid

C25H27NO8S (501.1457)

(2s)-2-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanedioic acid

C7H11NO6S (237.0307)

(2s)-2-(carboxyformamido)-3-(c-hydroxycarbonimidoylamino)propanoic acid

C6H9N3O6 (219.0491)

4-(2-aminophenyl)-2,3-dihydro-1h-pyrrole-2-carboxylic acid

C11H12N2O2 (204.0899)

2-amino-6-{[1-hydroxy-3-(3h-imidazol-4-yl)prop-2-en-1-ylidene]amino}hexanoic acid

C12H18N4O3 (266.1379)

2-amino-4-[(2-hydroxyethyl)-c-hydroxycarbonimidoyl]butanoic acid

C7H14N2O4 (190.0954)

2-({3-amino-6-[(1-carboxy-2-phenylethyl)-c-hydroxycarbonimidoyl]-1-hydroxyhexylidene}amino)-3-phenylpropanoic acid

C25H31N3O6 (469.2213)

5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pent-2-enenitrile

C11H17NO6 (259.1056)

4-(2-amino-2-carboxyethyl)-6-hydroxypyridine-2-carboxylic acid

C9H10N2O5 (226.059)

dl-aviglycine

C6H12N2O3 (160.0848)

(2s)-2-amino-4-{[(1s)-1-carboxy-2-(ethenylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C10H16N2O5S (276.078)

mycalenitrile-24

C26H44N2O (400.3453)

(2s)-2-amino-5-{[hydroxy(c-hydroxycarbonimidoylamino)methylidene]amino}pentanoic acid

C7H14N4O4 (218.1015)

4-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-oxabicyclo[3.1.0]hexane-2-carbonitrile

C12H17NO8 (303.0954)

(2s)-2-amino-4-[(4-oxobutyl)-c-hydroxycarbonimidoyl]butanoic acid

C9H16N2O4 (216.111)

1-hydroxy-4-(c-hydroxycarbonimidoyl)-2,3-dihydropyrrole-2-carboxylic acid

C6H8N2O4 (172.0484)

4,5-dibromo-1h-pyrrole-2-carbonitrile

C5H2Br2N2 (247.8585)

(2r,3s)-2-amino-4-ethoxy-3-hydroxybutanoic acid

C6H13NO4 (163.0845)

2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-1h-indol-3-yl)acetonitrile

C22H28N2O11 (496.1693)

2-[(1e,4s,6s)-4-hydroxy-6-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-ylidene]acetonitrile

C14H19NO7 (313.1161)

5-[(2s)-2-amino-2-carboxyethyl]-6-hydroxypyridine-2-carboxylic acid

C9H10N2O5 (226.059)

5-[(s)-amino(carboxy)methyl]-2-hydroxybenzoic acid

C9H9NO5 (211.0481)

(2r,5s)-5-hydroxypiperidine-2-carboxylic acid

C6H11NO3 (145.0739)

(4z)-4-{2-[(1-carboxy-4-hydroxybutyl)imino]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C14H18N2O7 (326.1114)

(2s)-2-amino-4-{[(1r)-1-carboxy-2-(prop-2-en-1-ylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C11H18N2O5S (290.0936)

2-amino-4-[(4-carbamimidamido-1-carboxybutyl)-c-hydroxycarbonimidoyl]butanoic acid

C11H21N5O5 (303.1543)

7-cyanohept-2-en-4,6-diynoic acid

C8H3NO2 (145.0164)

ethyl (2s)-1-[(2r,3s)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carboxylate

C21H37NO4 (367.2722)

methyl 2-[(2e)-n-hydroxy-2-(n-hydroxyimino)propanamido]-3-{4-[(3-methylbut-2-en-1-yl)oxy]phenyl}propanoate

C18H24N2O6 (364.1634)

(2s)-2-amino-5-[(4-hydroxy-5-methyl-1,5-dihydroimidazol-2-ylidene)amino]pentanoic acid

C9H16N4O3 (228.1222)

2-({2-carboxy-2-[(c-hydroxycarbonimidoylmethyl)amino]ethyl}amino)butanedioic acid

C9H15N3O7 (277.091)

(2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid

C6H12N2O3 (160.0848)

1-(2-methyldecanoyl)pyrrolidine-2-carboxylic acid

C16H29NO3 (283.2147)

4,5-dihydroxy-1-(2,3,4,5-tetrahydroxyphenoxy)cyclopent-2-ene-1-carbonitrile

C12H11NO7 (281.0535)

n-(6-amino-1-oxohex-4-en-2-yl)-3-[(4-{4-[(2-carbamimidamido-1-hydroxyethylidene)amino]-1h-pyrrole-2-amido}-1h-pyrrol-2-yl)formamido]-3-cyanopropanimidic acid

C23H29N11O5 (539.2353)

(2s)-2-amino-3-cyclopropylpropanoic acid

C6H11NO2 (129.079)

(18z)-24-(5-formyl-1h-pyrrol-2-yl)tetracos-18-enenitrile

C29H48N2O (440.3766)

(2s)-2-{[(2s)-3-amino-1-hydroxy-2-({hydroxy[3-(c-hydroxycarbonimidoyl)oxiran-2-yl]methylidene}amino)propylidene]amino}-3-methylbutanoic acid

C12H20N4O6 (316.1383)

4-(3-aminophenyl)-2-methyl-4-oxobutanoic acid

C11H13NO3 (207.0895)

(2s)-6-amino-2-{[(4s)-4-amino-4-carboxy-1-hydroxybutylidene]amino}hexanoic acid

C11H21N3O5 (275.1481)

4-(6-carboxy-6-methylhexa-2,5-dien-2-yl)-3-(carboxymethyl)pyrrolidine-2-carboxylic acid

C15H21NO6 (311.1369)

(2s)-2-amino-4-(carboxymethyl-c-hydroxycarbonimidoyl)butanoic acid

C7H12N2O5 (204.0746)

4-(2-oxoethylidene)-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C9H9NO5 (211.0481)

6-amino-3,5,7-trihydroxyheptanoic acid

C7H15NO5 (193.095)

6-amino-2-[(4-amino-4-carboxy-1-hydroxybutylidene)amino]hexanoic acid

C11H21N3O5 (275.1481)

(2r)-2-amino-3-sulfopropanimidic acid

C3H8N2O4S (168.0205)

2-amino-4-methylidenehexanoic acid

C7H13NO2 (143.0946)

(2r)-2-phenyl-2-{[(2r,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

C14H17NO6 (295.1056)

(2s,3s)-2-({[(2s)-1-[(2s,3s)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-3-methylpentanoic acid

C17H31N3O4 (341.2314)

(2s)-2-amino-3-(1-amino-3h-inden-2-yl)propanoic acid

C12H14N2O2 (218.1055)

2-amino-4-[(3-methyl-2,5-dihydrofuran-2-yl)-c-hydroxycarbonimidoyl]butanoic acid

C10H16N2O4 (228.111)

(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-4-methylpentanoic acid

C9H18N2O3 (202.1317)

4-amino-2-hydroxy-2-methylpentanedioic acid

C6H11NO5 (177.0637)

2-{[(2r,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-2-phenylacetonitrile

C19H25NO10 (427.1478)

(2s)-2-amino-5-(c-hydroxycarbonimidoylamino)pentanimidic acid

C6H14N4O2 (174.1117)

(2s)-2-amino-4-{[(4-hydroxyphenyl)methyl]-c-hydroxycarbonimidoyl}butanoic acid

C12H16N2O4 (252.111)

(2e)-2-cyano-2-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethylidene)ethyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C20H23NO9 (421.1373)

2-amino-5-chlorohex-4-enoic acid

C6H10ClNO2 (163.04)

(+)-(1s,2s)-coronamic acid

C6H11NO2 (129.079)

2-(3,4-dihydroxy-6-oxocyclohex-1-en-1-yl)acetonitrile

C8H9NO3 (167.0582)

(2s,3r)-3-aminopyrrolidine-2-carboxylic acid

C5H10N2O2 (130.0742)

(2s,4e)-4-{2-[(2s)-2-carboxypyrrolidin-1-yl]ethylidene}-2,3-dihydro-1h-pyridine-2,6-dicarboxylic acid

C14H18N2O6 (310.1165)

(1r,2s,3e,4s,6r)-6-(benzoyloxy)-3-(cyanomethylidene)-2-hydroxy-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl 1h-pyrrole-2-carboxylate

C26H28N2O11 (544.1693)

(2s)-2-{[(2s)-2-amino-1-hydroxy-3-phenylpropylidene]amino}butanedioic acid

C13H16N2O5 (280.1059)

1-amino-2-ethylcyclopropane-1-carboxylic acid

C6H11NO2 (129.079)

2-amino-3-cyanopentanedioic acid

C6H8N2O4 (172.0484)

(2s,4e)-2-amino-6-hydroxy-4-methylhex-4-enoic acid

C7H13NO3 (159.0895)

(2s,5s)-5-(aminomethyl)-5,6-dihydroxy-3,4-dihydro-2h-pyridine-2-carboxylic acid

C7H12N2O4 (188.0797)

2-amino-5-(c-hydroxycarbonimidoylamino)pentanimidic acid

C6H14N4O2 (174.1117)

(5-{[6-({6-[cyano(3-hydroxyphenyl)methoxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-4,5-dihydroxyoxan-3-yl]oxy}-3,4-dihydroxyoxolan-3-yl)methyl 3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoate

C39H49NO23 (899.2695)

(1r,2s,3r)-2,3-dihydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopentane-1-carbonitrile

C12H19NO8 (305.1111)

2-amino-4-{[(4-hydroxyphenyl)methyl]-c-hydroxycarbonimidoyl}butanoic acid

C12H16N2O4 (252.111)

3-{4-[(2r,3r,6s)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile

C22H21N3O4 (391.1532)

(4s)-4-amino-4-{[(1s)-1-carboxyethyl]-c-hydroxycarbonimidoyl}butanoic acid

C8H14N2O5 (218.0903)

(2s)-2-[(4-aminophenyl)formamido]-3-(1h-indol-3-yl)propanoic acid

C18H17N3O3 (323.127)

(2r,4r)-4-methoxypiperidine-2-carboxylic acid

C7H13NO3 (159.0895)

3-[amino(carboxy)methyl]benzoic acid

C9H9NO4 (195.0532)

2-[(4s,7r)-10-chloro-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraen-4-yl]acetonitrile

C16H16ClN3 (285.1033)

(3r)-n-[(2s,4e)-6-amino-1-oxohex-4-en-2-yl]-3-cyano-3-{[4-(4-{[1-hydroxy-2-(n'-hydroxycarbamimidamido)ethylidene]amino}-1h-pyrrole-2-amido)-1h-pyrrol-2-yl]formamido}propanimidic acid

C23H29N11O6 (555.2302)

(s)-cyano(hydroxy)methylphosphonic acid

C2H4NO4P (136.9878)

{6-[cyano(phenyl)methoxy]-3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

C28H25NO14 (599.1275)

(2s,5r)-5-hydroxypiperidine-2-carboxylic acid

C6H11NO3 (145.0739)

2-[(1z,4s,6s)-4-hydroxy-6-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-ylidene]acetonitrile

C14H19NO7 (313.1161)

(2r)-2-{[(1r)-1-carboxy-2-phenylethyl]amino}pentanedioic acid

C14H17NO6 (295.1056)

2-({2-[(4-carbamimidamido-1-carboxy-3-hydroxybutyl)amino]ethyl}amino)butanedioic acid

C12H23N5O7 (349.1597)

(2r)-2-phenyl-2-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile

C20H27NO11 (457.1584)

(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-3-phenylpropanoic acid

C11H14N2O3 (222.1004)

(2s,4s)-2-amino-4-{[(1z)-2-ethenyl-3-hydroxyprop-1-en-1-yl]-c-hydroxycarbonimidoyl}-4-hydroxybutanoic acid

C10H16N2O5 (244.1059)

2-amino-6-[(2,6-diamino-1-hydroxyhexylidene)amino]hexanoic acid

C12H26N4O3 (274.2005)

(2s)-2-amino-4-[(2-hydroxyethyl)-c-hydroxycarbonimidoyl]butanoic acid

C7H14N2O4 (190.0954)

methyl 1-(2-methyl-3-oxodec-8-enoyl)pyrrolidine-2-carboxylate

C17H27NO4 (309.194)

2-[(2-amino-1-hydroxypropylidene)amino]-3-({hydroxy[3-(c-hydroxycarbonimidoyl)oxiran-2-yl]methylidene}amino)propanoic acid

C10H16N4O6 (288.107)

2-amino-4-[(1-carboxy-2-methylpropyl)-c-hydroxycarbonimidoyl]butanoic acid

C10H18N2O5 (246.1216)

2-amino-3-(cyclohexa-2,5-dien-1-yl)propanoic acid

C9H13NO2 (167.0946)

(2r)-2-amino-8-(methylsulfanyl)octanoic acid

C9H19NO2S (205.1136)

2-amino-4-{[(3,4,5-trihydroxyoxolan-2-yl)methyl]sulfanyl}butanoic acid

C9H17NO6S (267.0777)

(2z)-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}but-2-enenitrile

C10H15NO6 (245.0899)

methyl (2s)-1-[(2s,8e)-2-methyl-3-oxodec-8-enoyl]pyrrolidine-2-carboxylate

C17H27NO4 (309.194)

2-[(1z,2r,3r,4r,6s)-2,4-dihydroxy-3,6-bis({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})cyclohexylidene]acetonitrile

C20H31NO14 (509.1744)

(2r)-5-hydroxy-3,4-dihydro-2h-pyrrole-2-carboxylic acid

C5H7NO3 (129.0426)

2-[(1-carboxy-2-methylbutyl)amino]pentanedioic acid

C11H19NO6 (261.1212)

(2r,3s,4r,5r,6s)-6-{4-[(s)-cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C23H23NO10 (473.1322)

(2e,4e)-4-[cyano({[(1s,2r,3r,4r,5s,6s)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})methylidene]hex-2-enedioic acid

C14H17NO10 (359.0852)

(3s)-3-{[(2r)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid

C7H13NO4S (207.0565)

(1r,4s)-4-hydroxy-1-{[(2s,3r,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-ene-1-carbonitrile

C12H17NO7 (287.1005)

(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}butanedioic acid

C7H12N2O5 (204.0746)

(2s)-2-amino-6-[(1-hydroxyethylidene)amino]hexanoic acid

C8H16N2O3 (188.1161)

2-[(3-amino-1,2-dihydroxy-4-methylpentylidene)amino]-3-methylbutanoic acid

C11H22N2O4 (246.1579)

2-amino-4-[(4-amino-1-carboxybutyl)-c-hydroxycarbonimidoyl]butanoic acid

C10H19N3O5 (261.1325)

β-2-amino-4-methylvaleric acid

C6H13NO2 (131.0946)

(1r,4r)-1-[(2s)-2-amino-2-carboxyethyl]-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid

C10H13NO5 (227.0794)

3-[(2-amino-2-carboxyethyl)sulfanyl]butanoic acid

C7H13NO4S (207.0565)

(2s)-2-amino-4-[(3-carboxypropyl)-c-hydroxycarbonimidoyl]butanoic acid

C9H16N2O5 (232.1059)

[(9e)-16-(cyanosulfanyl)hexadec-9-en-1-yl]sulfanylcarbonitrile

C18H30N2S2 (338.185)

(2s)-2-amino-3-(5-oxo-2h-1,2-oxazol-4-yl)propanoic acid

C6H8N2O4 (172.0484)

(2s,3r)-2-amino-3-[(1s)-2-methylidenecyclopropyl]butanoic acid

C8H13NO2 (155.0946)

(2r,3s,4r,5r,6s)-6-{4-[cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C23H23NO10 (473.1322)

2-amino-3-(5-oxooxolan-2-yl)propanoic acid

C7H11NO4 (173.0688)

(+/-)-mimosine

C8H10N2O4 (198.0641)

(2s)-2-amino-3-cyclopropylbutanoic acid

C7H13NO2 (143.0946)

(2s)-2-amino-4-[(4-hydroxyphenyl)carbamoyl]butanoic acid

C11H14N2O4 (238.0954)

(2s,4r,5s)-4,5-dihydroxypiperidine-2-carboxylic acid

C6H11NO4 (161.0688)

2-amino-6-carbamimidamido-4-hydroxyhexanoic acid

C7H16N4O3 (204.1222)

2-{[(2r,3s)-3-methyl-2-[(2s)-1-[(2s)-2-methyldecanoyl]pyrrolidine-2-carbonyloxy]pentanoyl]oxy}propanoic acid

C25H43NO7 (469.3039)

2,5-diamino-2-hydroxyhexanoic acid

C6H14N2O3 (162.1004)

(2r)-2-[(4s)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

C14H19NO7 (313.1161)

(2r,4s)-2-amino-6-carbamimidamido-4-hydroxyhexanoic acid

C7H16N4O3 (204.1222)

2-[(1z,4r,5r,6s)-4,5-dihydroxy-6-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-ylidene]acetonitrile

C14H19NO8 (329.1111)

(2s)-3-({[(9r)-5,10-dihydroxy-4,9-dimethoxy-6-oxo-7h,8h,9h,11h-cyclohexa[b]fluoren-2-yl]methyl}sulfanyl)-2-[(1-hydroxyethylidene)amino]propanoic acid

C25H27NO8S (501.1457)

6-{4-[cyano(hydroxy)methyl]phenoxy}-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C23H23NO10 (473.1322)

2-(4-hydroxy-2-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)acetonitrile

C14H17NO7 (311.1005)

2-amino-5-methylhex-5-enoic acid

C7H13NO2 (143.0946)

(2s)-2-amino-4-{[(1s)-1-carboxy-2-(4-hydroxyphenyl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C14H18N2O6 (310.1165)

(2s)-2-amino-4,4-dichlorobutanoic acid

C4H7Cl2NO2 (170.9854)

(s)-amino(1-methylcyclopropyl)acetic acid

C6H11NO2 (129.079)

(2s)-2-[(2-{[(2s)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxyethylidene)amino]butanedioic acid

C12H22N6O6 (346.1601)

(2s)-2-amino-5-methylhex-5-enoic acid

C7H13NO2 (143.0946)

(2s,4s)-4-hydroxypiperidine-2-carboxylic acid

C6H11NO3 (145.0739)

2-[(4-aminophenyl)formamido]-3-(1h-indol-3-yl)propanoic acid

C18H17N3O3 (323.127)

2-amino-4-{[1-carboxy-2-(prop-1-en-1-ylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C11H18N2O5S (290.0936)

amino(2-hydroxycyclopent-3-en-1-yl)acetic acid

C7H11NO3 (157.0739)

2-amino-4-{[carboxy(2-methylidenecyclopropyl)methyl]-c-hydroxycarbonimidoyl}butanoic acid

C11H16N2O5 (256.1059)

(2r)-2-[(carboxymethyl)amino]-3-(1h-indol-3-yl)propanoic acid

C13H14N2O4 (262.0954)

(2s,3r)-3-hydroxy-2-(hydroxyamino)butanoic acid

C4H9NO4 (135.0532)

3-(5-oxo-4h-1,2-oxazol-3-yl)propanenitrile

C6H6N2O2 (138.0429)

(1s,2r)-1-amino-2-(carbamimidamidomethyl)cyclopropane-1-carboxylic acid

C6H12N4O2 (172.096)

{[(2s,3s)-2-amino-1-hydroxy-3-methylpentylidene]amino}acetic acid

C8H16N2O3 (188.1161)

thiophene-2,5-dicarbonitrile

C6H2N2S (133.9939)

(2s,4s)-2-amino-4,5-dihydroxypentanoic acid

C5H11NO4 (149.0688)

2-amino-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propanoic acid

C14H19NO3 (249.1365)

2-amino-4-[(4-hydroxyphenyl)carbamoyl]butanoic acid

C11H14N2O4 (238.0954)

2-[(2-amino-1-hydroxypropylidene)amino]-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

C12H18N2O5 (270.1216)

2-aminoethoxyphosphonous acid

C2H8NO3P (125.0242)

2,6-diamino-7-hydroxynonanedioic acid

C9H18N2O5 (234.1216)

2-[(1z,4r,6s)-4-hydroxy-6-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-ylidene]acetonitrile

C14H19NO7 (313.1161)

(2s)-2-amino-4-{[(1r)-1-carboxy-2-methanesulfonylethyl]-c-hydroxycarbonimidoyl}butanoic acid

C9H16N2O7S (296.0678)

3-({[(2-amino-1-hydroxypropylidene)amino]methyl}-c-hydroxycarbonimidoyl)-2-methanesulfonylpropanoic acid

C9H17N3O6S (295.0838)

(2s)-2-amino-3-(3-formyl-4-hydroxyphenyl)propanoic acid

C10H11NO4 (209.0688)

2-amino-3-[3-(hydroxymethyl)phenyl]propanoic acid

C10H13NO3 (195.0895)

4-(methylamino)benzamide

C8H10N2O (150.0793)

(2s,3s,4s)-4-[(2e,5e)-6-carboxy-6-methylhexa-2,5-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid

C15H21NO6 (311.1369)

2-[(2-amino-1-hydroxypropylidene)amino]-3-{5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl}propanoic acid

C12H18N2O5 (270.1216)

2-hydrazinylpyridine-3-carboxylic acid

C6H7N3O2 (153.0538)

(2s,3z)-3-(2-aminoethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

C8H10N2O4 (198.0641)

4,5-dihydroxypiperidine-2-carboxylic acid

C6H11NO4 (161.0688)

(2s)-5-carbamimidamido-2-[(3-carboxy-1-hydroxypropylidene)amino]pentanoic acid

C10H18N4O5 (274.1277)

(2s)-1-[(5s)-5-amino-5-carboxypentyl]-5-oxopyrrolidine-2-carboxylic acid

C11H18N2O5 (258.1216)

[(8r)-16-(cyanosulfanyl)-8-hydroxyhexadecyl]sulfanylcarbonitrile

C18H32N2OS2 (356.1956)

(2s)-2-{[(2s)-2-amino-1-hydroxy-3-methylbutylidene]amino}-4-methylpentanoic acid

C11H22N2O3 (230.163)

(1s,10s,11r,12s,22r)-20,23-dioxo-9-oxa-4,13-diazahexacyclo[9.8.3.2¹⁰,¹³.0¹,¹².0⁶,²².0¹⁴,¹⁹]tetracosa-6,14,16,18-tetraene-4-carbonitrile

C22H21N3O3 (375.1583)

d-2-aminopimelic acid

C7H13NO4 (175.0845)

(2s)-2-amino-5-chloro-4-hydroxyhex-5-enoic acid

C6H10ClNO3 (179.0349)

3-[(2s)-2-amino-2-carboxyethyl]benzoic acid

C10H11NO4 (209.0688)

(2s)-2-amino-5-chlorohex-5-enoic acid

C6H10ClNO2 (163.04)

(2s)-2-{[(2s)-2-amino-1-hydroxypropylidene]amino}-3-hydroxypropanoic acid

C6H12N2O4 (176.0797)

(2s,4z)-2-amino-5-chloro-6-hydroxyhex-4-enoic acid

C6H10ClNO3 (179.0349)

(2s,4s)-2-amino-4-hydroxypentanoic acid

C5H11NO3 (133.0739)

4-(2-amino-2-carboxyethyl)-1h-pyrrole-2-carboxylic acid

C8H10N2O4 (198.0641)

(2s)-2-{[(1s)-3-{[(2r)-2-amino-2-carboxyethyl]selanyl}-1-carboxypropyl]amino}-4-(c-hydroxycarbonimidoyl)butanoic acid

C12H21N3O7Se (399.0545)

3-amino-6-[(1-hydroxyethylidene)amino]hexanoic acid

C8H16N2O3 (188.1161)

(5s,6s)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carbaldehyde

C7H9NO2 (139.0633)

(2s)-2-amino-4-(isopropyl-c-hydroxycarbonimidoyl)butanoic acid

C8H16N2O3 (188.1161)

methyl (2s)-2-amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoate

C9H12N2O4 (212.0797)

(2s)-2-(cyclopropylamino)propanoic acid

C6H11NO2 (129.079)

2-amino-4-{[1-carboxy-2-(prop-2-en-1-yldisulfanyl)ethyl]-c-hydroxycarbonimidoyl}butanoic acid

C11H18N2O5S2 (322.0657)

(2s)-2-amino-4-[(1-hydroxyethylidene)amino]butanoic acid

C6H12N2O3 (160.0848)

(2s,3r)-3-(hydroxymethyl)-3-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxirane-2-carbonitrile

C11H17NO8 (291.0954)

2-[(1z,4s,5r,6r)-4,5-dihydroxy-6-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohex-2-en-1-ylidene]acetonitrile

C14H19NO8 (329.1111)

1-[(4-hydroxyphenyl)methyl]hydrazinecarboxylic acid

C8H10N2O3 (182.0691)

{6-[cyano(phenyl)methoxy]-5-hydroxy-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

C35H29NO18 (751.1385)

(2s)-2-amino(²h₄)propanoic acid

C3H7NO2 (89.0477)

(2s,4s)-2-amino-4-chloropentanoic acid

C5H10ClNO2 (151.04)

d(-)-asparagine monohydrate

C4H8N2O3 (132.0535)

dihydrophenylalanine

C9H13NO2 (167.0946)

(2s)-2-amino-3-[(1r,2r,6r)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid

C9H13NO4 (199.0845)

[(3s,4r,5r)-5-{[(2r,3s,4s,5r,6r)-6-[(r)-cyano(phenyl)methoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl benzoate

C26H29NO11 (531.1741)