Classification Term: 2160

2-Aminoisobutyric acid, also known as alpha-methylalanine or a-aminoisobutanoate, 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-Aminoisobutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2-Aminoisobutyric acid has been detected, but not quantified in cow milk. Aminoisobutyric acid is a nonprotein amino acid (is an end product of pyrimidine metabolism) excreted in the urine of about 5\\\\\% of healthy individuals (PMID 14806475), and high excretion is an autosomal recessive phenotype (PMID 13058271). 2-aminoisobutyric acid is a rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays. It is functionally related to a propionic acid and an isobutyric acid. It is a tautomer of a 2-aminoisobutanoic acid zwitterion. 2-Aminoisobutyric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Aminoisobutyric acid is a nonprotein amino acid (is an end product of pyrimidine metabolism) excreted in the urine of about 5\\\\\% of healthy individuals (PMID 14806475), and high excretion is an autosomal recessive phenotype (PMID 13058271) [HMDB] A rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays. Aminoisobutyric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=765258-64-8 (retrieved 2024-07-01) (CAS RN: 62-57-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). NSC 16590 inhibits the production of endogenous ethylene in the cotyledonary segments of cocklebur. NSC 16590 inhibits the production of endogenous ethylene in the cotyledonary segments of cocklebur.

2-Phenylglycine

DL-alpha-Aminophenylacetic acid

C8H9NO2 (151.0633)

2-Phenylglycine, also known as a-amino-a-toluate or L-PHG amino acid, 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). Outside of the human body, 2-Phenylglycine has been detected, but not quantified in cow milk. This could make 2-phenylglycine a potential biomarker for the consumption of these foods. 2-Phenylglycine is a metabolite described in normal human urine (PMID 14473597) and plasma (PMID 5888801). 2-Phenylglycine is a metabolite described in normal human urine (PMID 14473597) and plasma (PMID 5888801) [HMDB]

DL-Homocystine

2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid

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.

Pipecolic acid

Pipecolic acid, 14C-labeled CPD, (+,-)-isomer

C6H11NO2 (129.079)

Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients (PMID 12705501). Pipecolic acid is found to be associated with adrenoleukodystrophy, infantile Refsum disease, and peroxisomal biogenesis defect, which are also inborn errors of metabolism. Pipecolic acid is a biomarker for the consumption of dried and cooked beans. Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients. (PMID 12705501) [HMDB]. Pipecolic acid is a biomarker for the consumption of dried and cooked beans. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID P048 L-Pipecolic acid (H-HoPro-OH) is a breakdown product of lysine, accumulates in body fluids of infants with generalized genetic peroxisomal disorders, such as Zellweger syndrome, neonatal adrenoleukodystrophy. L-Pipecolic acid (H-HoPro-OH) is a breakdown product of lysine, accumulates in body fluids of infants with generalized genetic peroxisomal disorders, such as Zellweger syndrome, neonatal adrenoleukodystrophy. Pipecolic acid, a metabolite of Lysine, is an important precursor of many useful microbial secondary metabolites. Pipecolic acid can be used as a diagnostic marker of Pyridoxine-dependent epilepsy[1][2]. Pipecolic acid, a metabolite of Lysine, is an important precursor of many useful microbial secondary metabolites. Pipecolic acid can be used as a diagnostic marker of Pyridoxine-dependent epilepsy[1][2].

N-Ethylglycine

2-(ethylamino)acetic acid

N-Ethylglycine, also known as EG, belongs to the family of 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). N-ethylglyicne is a known metabolite of the anesthesia drug lidocaine (PMID: 25932687). N-ethylglyicne is also an endogenously produced metabolite and appears in normal subjects’ urine in small amounts, but its presence is significantly higher in patients with metastatic bone disease (PMID: 16962088). Research has shown that it is lidocaine’s metabolites, n-ethylglycine and monoethylglycinexylidide inhibit GlyT1-mediated uptake of glycine. N-ethylglycine acts as a substrate for the glycine transporter GlyT1 (PMID: 22133759, 25932687).

L-Hypoglycin A

alpha-amino-beta-(2-Methylenecyclopropyl)propionic acid

C7H11NO2 (141.079)

Isolated from the unripe fruit of akee apple (Blighia sapida). L-Hypoglycin A is found in many foods, some of which are fox grape, biscuit, mamey sapote, and chinese chives. L-Hypoglycin A is found in fruits. L-Hypoglycin A is isolated from the unripe fruit of akee apple (Blighia sapida D009676 - Noxae > D011042 - Poisons > D007005 - Hypoglycins

Nitrilotriacetic acid

alpha,Alpha,alpha-trimethylaminetricarboxylic acid

C6H9NO6 (191.043)

D064449 - Sequestering Agents > D002614 - Chelating Agents

Glycine

2-aminoacetic acid

C2H5NO2 (75.032)

Glycine (Gly), 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. Glycine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Glycine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid and is the simplest of all amino acids. In humans, glycine is a nonessential amino acid, although experimental animals show reduced growth on low-glycine diets. The average adult human ingests 3 to 5 grams of glycine daily. Glycine is a colorless, sweet-tasting crystalline solid. It is the only achiral proteinogenic amino acid. Glycine was discovered in 1820 by the French chemist Henri Braconnot when he hydrolyzed gelatin by boiling it with sulfuric acid. The name comes from the Greek word glucus or "sweet tasting". Glycine is biosynthesized in the body from the amino acid serine, which is in turn derived from 3-phosphoglycerate. In the liver of vertebrates, glycine synthesis is catalyzed by glycine synthase (also called glycine cleavage enzyme). In addition to being synthesized from serine, glycine can also be derived from threonine, choline or hydroxyproline via inter-organ metabolism of the liver and kidneys. Glycine is degraded via three pathways. The predominant pathway in animals and plants is the reverse of the glycine synthase pathway. In this context, the enzyme system involved glycine metabolism is called the glycine cleavage system. The glycine cleavage system catalyzes the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism. Patients with a deficiency of this enzyme system have increased glycine in plasma, urine, and cerebrospinal fluid (CSF) with an increased CSF:plasma glycine ratio (PMID: 16151895). Glycine levels are effectively measured in plasma in both normal patients and those with inborn errors of glycine metabolism (http://www.dcnutrition.com/AminoAcids/). Nonketotic hyperglycinaemia (OMIM: 606899) is an autosomal recessive condition caused by deficient enzyme activity of the glycine cleavage enzyme system (EC 2.1.1.10). The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10, and EC 1.8.1.4 for P-, T-, and L-proteins). Mutations have been described in the GLDC (OMIM: 238300), AMT (OMIM: 238310), and GCSH (OMIM: 238330) genes encoding the P-, T-, and H-proteins respectively. Glycine is involved in the bodys production of DNA, hemoglobin, and collagen, and in the release of energy. The principal function of glycine is as a precursor to proteins. Most proteins incorporate only small quantities of glycine, a notable exception being collagen, which contains about 35\\\\\\% glycine. In higher eukaryotes, delta-aminolevulinic acid, the key precursor to porphyrins (needed for hemoglobin and cytochromes), is biosynthesized from glycine and succinyl-CoA by the enzyme ALA synthase. Glycine provides the central C2N subunit of all purines, which are key constituents of DNA and RNA. Glycine is an inhibitory neurotransmitter in the central nervous system, especially in the spinal cord, brainstem, and retina. When glycine receptors are activated, chloride enters the neuron via ionotropic receptors, causing an inhibitory postsynaptic potential (IPSP). Glycine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-40-6 (retrieved 2024-07-02) (CAS RN: 56-40-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Glycine is an inhibitory neurotransmitter in the CNS and also acts as a co-agonist along with glutamate, facilitating an excitatory potential at the glutaminergic N-methyl-D-aspartic acid (NMDA) receptors. Glycine is an inhibitory neurotransmitter in the CNS and also acts as a co-agonist along with glutamate, facilitating an excitatory potential at the glutaminergic N-methyl-D-aspartic acid (NMDA) receptors. Glycine is orally active. Glycine can be used to study cell protection, cancer, neurological diseases, and angiogenesis[1][2][3][4][5][6]. Glycine is an inhibitory neurotransmitter in the CNS and also acts as a co-agonist along with glutamate, facilitating an excitatory potential at the glutaminergic N-methyl-D-aspartic acid (NMDA) receptors.

Dimethylglycine

N-Methylsarcosine N,N-dimethyl-glycine

Dimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N,N-dimethylglycine by betaine-homocysteine methyltransferase. DMG in the urine is a biomarker for the consumption of legumes. It is also a microbial metabolite (PMID: 25901889). Dimethylglycine (DMG) is an amino acid derivative found in the cells of all plants and animals and can be obtained in the diet in small amounts from grains and meat. The human body produces DMG when metabolizing choline into Glycine. Dimethylglycine that is not metabolized in the liver is transported by the circulatory system to body tissue. Dimethylglycine was popular with Russian athletes and cosmonauts owing to its reputed ability to increase endurance and reduce fatigue. DMG is also a byproduct of homocysteine metabolism. Homocysteine and betaine are converted to methionine and N, N-dimethylglycine by betaine-homocysteine methyltransferase. [HMDB]. Dimethylglycine in the urine is a biomarker for the consumption of legumes. N,N-Dimethylglycine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1118-68-9 (retrieved 2024-07-16) (CAS RN: 1118-68-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). N-Methylsarcosine is an amino acid building block for protein, found in a small amount in the body.

Cysteic acid

2-Amino-3-sulfopropionic acid

C3H7NO5S (169.0045)

Cysteic acid is a crystalline amino acid formed in the oxidation of cysteine; it is a precursor of taurine. A crystalline amino acid formed in the oxidation of cysteine; it is a precursor of taurine. [HMDB]

Sarcosine

2-(methylamino)acetic acid

C3H7NO2 (89.0477)

Sarcosine is the N-methyl derivative of glycine. Sarcosine is metabolized to glycine by the enzyme sarcosine dehydrogenase, while glycine-N-methyl transferase generates sarcosine from glycine. Sarcosine is a natural amino acid found in muscles and other body tissues. In the laboratory it may be synthesized from chloroacetic acid and methylamine. Sarcosine is naturally found in the metabolism of choline to glycine. Sarcosine is sweet to the taste and dissolves in water. It is used in manufacturing biodegradable surfactants and toothpastes as well as in other applications. Sarcosine is ubiquitous in biological materials and is present in such foods as egg yolks, turkey, ham, vegetables, legumes, etc. Sarcosine is formed from dietary intake of choline and from the metabolism of methionine, and is rapidly degraded to glycine. Sarcosine has no known toxicity, as evidenced by the lack of phenotypic manifestations of sarcosinemia, an inborn error of sarcosine metabolism. Sarcosinemia can result from severe folate deficiency because of the folate requirement for the conversion of sarcosine to glycine (Wikipedia). Sarcosine has recently been identified as a biomarker for invasive prostate cancer. It was found to be greatly increased during prostate cancer progression to metastasis and could be detected in urine. Sarcosine levels were also increased in invasive prostate cancer cell lines relative to benign prostate epithelial cells (PMID: 19212411). Sarcosine, also known as N-methylglycine or (methylamino)acetic 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). Sarcosine is soluble (in water) and a moderately acidic compound (based on its pKa). Sarcosine can be found in peanut, which makes sarcosine a potential biomarker for the consumption of this food product. Sarcosine can be found primarily in most biofluids, including blood, saliva, cerebrospinal fluid (CSF), and feces, as well as in human muscle, prostate and skeletal muscle tissues. Sarcosine exists in all living organisms, ranging from bacteria to humans. In humans, sarcosine is involved in few metabolic pathways, which include glycine and serine metabolism, methionine metabolism, and sarcosine oncometabolite pathway. Sarcosine is also involved in several metabolic disorders, some of which include homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblg complementation type, hyperglycinemia, non-ketotic, hypermethioninemia, and dimethylglycine dehydrogenase deficiency. Moreover, sarcosine is found to be associated with sarcosinemia. Sarcosine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Sarcosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-97-1 (retrieved 2024-07-01) (CAS RN: 107-97-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Sarcosine (N-Methylglycine), an endogenous amino acid, is a competitive glycine transporter type I (GlyT1) inhibitor and N-methyl-D-aspartate (NMDA) receptor co-agonist. Sarcosine increases the glycine concentration, resulting in an indirect potentiation of the NMDA receptor. Sarcosine is commonly used for the research of schizophrenia[1][2]. Sarcosine (N-Methylglycine), an endogenous amino acid, is a competitive glycine transporter type I (GlyT1) inhibitor and N-methyl-D-aspartate (NMDA) receptor co-agonist. Sarcosine increases the glycine concentration, resulting in an indirect potentiation of the NMDA receptor. Sarcosine is commonly used for the research of schizophrenia[1][2].

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

alpha-amino-beta-(Pyrazolyl-N)propionic acid

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.

1-Aminocyclopropanecarboxylic acid

1-Aminocyclopropane-1-carboxylic acid hydrochloride

C4H7NO2 (101.0477)

1-aminocyclopropanecarboxylic acid, also known as acc or 1-amino-1-carboxycyclopropane, 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). 1-aminocyclopropanecarboxylic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 1-aminocyclopropanecarboxylic acid can be found in a number of food items such as american cranberry, chayote, sour cherry, and garden rhubarb, which makes 1-aminocyclopropanecarboxylic acid a potential biomarker for the consumption of these food products. ACC plays an important role in the biosynthesis of the plant hormone ethylene. It is synthesized by the enzyme ACC synthase ( EC 4.4.1.14) from methionine and converted to ethylene by ACC oxidase (EC 1.14.17.4) . 1-Aminocyclopropanecarboxylic acid is found in fruits. 1-Aminocyclopropanecarboxylic acid is isolated from apple and pear juice and cranberries. Acquisition and generation of the data is financially supported in part by CREST/JST. D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents D020011 - Protective Agents KEIO_ID A047 1-Aminocyclopropane-1-carboxylic acid is an endogenous metabolite.

2-Amino-3-phosphonopropionic acid

2-Amino-3-phosphonopropionic acid, sodium salt

C3H8NO5P (169.014)

2-Amino-3-phosphonopropionic acid (AP-3 or 2-AP3), also known as 3-phosphonoalanine, is a non-proteinogenc alpha-amino acid that is alanine in which one of the hydrogens of the terminal methyl group has been replaced by a dihydroxy(oxido)-lambda(5)-phosphanyl group. It is found in many organisms ranging from microbes to invertebrates to animals. In humans AP-3 is found in diverse tissues, such as liver, intestine and spleen. (PMID: 2627760). 2-Amino-3-phosphonopropionic acid is a ubiquitous naturally occurring phosphonate used as a source of phosphorus by many prokaryotic organisms (PMID: 30119975). The natural occurrence of 2-amino-3-phosphonopropionic acid. the phosphonate analogue of aspartic acid, was first reported by Kittredge & Hughes (PMID: 14214094) in the sea anemone Zoanthus sociatus and the protozoon Tetrahymena pyriformis. It has since been established to be one of the most widely distributed of the biogenic C‚ÄìP compounds, particularly among the lower marine invertebrates (PMID: 19191873). AP-3 has been determined to be a metabotropic glutamate receptor agonist (PMID: 8836635). It has been shown to block the amyloid precursor protein (APP) release evoked by glutamate receptor stimulation in neurons of the cortex and hippocampus. APP accumulation is believed to produce the damage in Alzheimer‚Äôs disease (PMID: 7644542). 2-Amino-3-phosphonopropionic acid (AP-3)is a normal human metabolite found in diverse tissues, such as liver, intestine and spleen. (PMID 2627760) AP-3 is a metabotropic glutamate receptor agonist (PMID 8836635) shown to block the amyloid precursor protein (APP) release evoked by glutamate receptor stimulation in neurons of the cortex and hippocampus; APP accumulation is believed to produce the damage in Alzheimer disease (PMID 7644542) [HMDB] D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists KEIO_ID A131 DL-AP3 is a competitive mGluR1 and mGluR5 antagonist. DL-AP3 is also an inhibitor of phosphoserine phosphatase. DL-AP3 has neuroprotective effect[1][2][3].

(S)-2-Azetidinecarboxylic acid

1-Azetidinecarboxylicacid, 2-(aminocarbonyl)-, 1,1-dimethylethyl ester, (2S)-

C4H7NO2 (101.0477)

Azetidine-2-carboxylic acid is an azetidinecarboxylic acid that is azetidine substituted by a carboxy group at position 2. It is a plant non-protein amino acid. It has a role as a plant metabolite and a teratogenic agent. It is an azetidinecarboxylic acid and an amino acid. A proline analog that acts as a stoichiometric replacement of proline. It causes the production of abnormal proteins with impaired biological activity. (S)-2-Azetidinecarboxylic acid is found in common beet. (S)-2-Azetidinecarboxylic acid is present in roots and leaves of Convallaria majalis (lily-of-the-valley). Convallaria majalis is banned by the FDA from food use in the US Present in roots and leaves of Convallaria majalis (lily-of-the-valley). Convallaria majalis is banned by the FDA from food use in the USA. (S)-2-Azetidinecarboxylic acid is found in red beetroot and common beet. An azetidinecarboxylic acid that is azetidine substituted by a carboxy group at position 2. It is a plant non-protein amino acid. KEIO_ID A219 Azetidine-2-carboxylic acid is a non proteinogenic amino acid homologue of proline. Found in common beets. Azetidine-2-carboxylic acid can be misincorporated into proteins in place of proline in many species, including humans. Toxic and teratogenic agent[1][2]. Azetidine-2-carboxylic acid is a non proteinogenic amino acid homologue of proline. Found in common beets. Azetidine-2-carboxylic acid can be misincorporated into proteins in place of proline in many species, including humans. Toxic and teratogenic agent[1][2]. L-Azetidine-2-carboxylic acid is an endogenous metabolite. L-Azetidine-2-carboxylic acid is an endogenous metabolite.

Methionine sulfoximine

Butanoic acid, 2-amino-4-(S-methylsulfonimidoyl)- (9ci)

C5H12N2O3S (180.0569)

Methionine sulfoximine is found in flours treated with NCl3 as a produced of NCl3 action on wheat protein

(-)-2-Difluoromethylornithine

Women first brand OF eflornithine hydrochloride

C6H12F2N2O2 (182.0867)

P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01C - Agents against leishmaniasis and trypanosomiasis C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D004791 - Enzyme Inhibitors > D065108 - Ornithine Decarboxylase Inhibitors C471 - Enzyme Inhibitor > C2088 - Ornithine Decarboxylase Inhibitor D000970 - Antineoplastic Agents D - Dermatologicals KEIO_ID H097

L-Phosphoarginine

2-amino-5-(1-phosphonocarbamimidamido)pentanoic acid

C6H15N4O5P (254.078)

L-Phosphoarginine is found in crustaceans. L-Phosphoarginine is a constituent of crayfish muscle KEIO_ID P105

O-acetylhomoserine

O-Acetyl-L-homoserine hydrochloride

C6H11NO4 (161.0688)

Acetylhomoserine is found in pulses. Acetylhomoserine is found in Pisum sativum (peas) Acquisition and generation of the data is financially supported in part by CREST/JST. Found in green tissues of pea (Pisum sativum)

Sennoside A

(9R)-9-[(9R)-2-carboxy-4-hydroxy-10-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracen-9-yl]-4-hydroxy-10-oxo-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-2-carboxylic acid

C42H38O20 (862.1956)

Senna (powdered) is a yellow-brown powder with a slight odor and taste. (NTP, 1992) Sennoside A is a member of the class of sennosides that is rel-(9R,9R)-9,9,10,10-tetrahydro-9,9-bianthracene-2,2-dicarboxylic acid which is substituted by hydroxy groups at positions 4 and 4, by beta-D-glucopyranosyloxy groups at positions 5 and 5, and by oxo groups at positions 10 and 10. The exact stereochemisty at positions 9 and 9 is not known - it may be R,R (as shown) or S,S. It is a member of sennosides and an oxo dicarboxylic acid. Senna (Cassia species) is a popular herbal laxative that is available without prescription. Senna is generally safe and well tolerated, but can cause adverse events including clinically apparent liver injury when used in high doses for longer than recommended periods. Sennoside A is a natural product found in Rheum officinale, Rheum palmatum, and other organisms with data available. Preparations of SENNA PLANT. They contain sennosides, which are anthraquinone type CATHARTICS and are used in many different preparations as laxatives. A member of the class of sennosides that is rel-(9R,9R)-9,9,10,10-tetrahydro-9,9-bianthracene-2,2-dicarboxylic acid which is substituted by hydroxy groups at positions 4 and 4, by beta-D-glucopyranosyloxy groups at positions 5 and 5, and by oxo groups at positions 10 and 10. The exact stereochemisty at positions 9 and 9 is not known - it may be R,R (as shown) or S,S. Cathartic principle from rhubarb. Sennoside A is found in green vegetables and garden rhubarb. Sennoside A is found in garden rhubarb. Cathartic principle from rhubar D005765 - Gastrointestinal Agents > D054368 - Laxatives Sennoside A is an anthraquinone glycoside, found in Senna (Cassia angustifolia)[1]. Sennoside A is a HIV-1 inhibitor effective on HIV-1 replication[2]. Sennoside A is an anthraquinone glycoside, found in Senna (Cassia angustifolia)[1]. Sennoside A is a HIV-1 inhibitor effective on HIV-1 replication[2].

Fructosyl-lysine

2-amino-6-[(3,4,5,6-tetrahydroxy-2-oxohexyl)amino]hexanoic acid

C12H24N2O7 (308.1583)

Aminomalonic acid

2-aminopropanedioic acid

C3H5NO4 (119.0219)

Aminomalonic acid (Ama) is an amino dicarboxylic acid that is an analog of malonic acid in which one of the methylene hydrogens has been replaced by an amino group. It is a strongly acidic compound that is very water soluble. Aminomalonic acid is a natural occurring, largely non-proteogenic amino acid that was first detected in alkaline hydrolysates of proteins in 1984. In particular, aminomalonic acid was isolated from proteins isolated from Escherichia coli cultures and from human atherosclerotic plaques (PMID: 6366787). Aminomalonic acid is a relatively unstable, minor amino acid in complex structures such as bacteria or tissues. The presence of aminomalonic acid has important biological implications because the malonic acid moiety potentially imparts calcium binding properties to proteins. Possible origins of aminomalonic acid in proteins include its introduction via errors in protein synthesis and oxidative damage to amino acid residues in proteins. (PMID: 1621954 , 6366787 ). Aminomalonic acid can be generated naturally via the activity of mammalian and bacterial enzymes on various precursors such as 2-aminomalonamide, diethylaminomalonate and ketomalonic acid (PMID: 35346). Free aminomalonic acid appears to be an oxidation product arising from perturbed serine or threonine metabolism. Aminomalonic acid is produced in animals that have been exposed to Cadmium (a strong pro-oxidant) for extended periods of time and it has been proposed to be a potential biomarker of Cadmium toxicity (PMID: 32193438). Aminomalonic acid has also been found to be elevated in the urine of individuals with anxiety and major depressive disorders (PMID: 30232320). Aminomalonic acid has been reported to be a potential biomarker for hepatocellular carcinoma (PMID: 18767022) and it exhibits strong inhibitory effects on L-asparagine synthase (PMID: 35346). Several metabolomics studies have also found that altered aminomalonic acid levels in serum are associated with neuropsychiatric disorders, melanoma, ketamine overdose and aortic aneurysm, indicating that aminomalonic acid is an important serum indicator for diseases and toxicities (PMID: 32193438). Aminomalonic acid (Ama) was first detected in alkaline hydrolysates of proteins in 1984. Ama has been isolated from proteins of Escherichia coli and human atherosclerotic plaque. The presence of Ama has important biological implications because the malonic acid moiety potentially imparts calcium binding properties to protein. Ama is not formed from any of the 20 major amino acids during the hydrolysis procedure. Furthermore, the amount of Ama found does not depend on the presence of small amounts of O2 during the hydrolysis. No artifactual formation of ama has been demonstrated and may indeed be a constituent of proteins before the hydrolysis procedure. Possible origins of Ama include errors in protein synthesis and oxidative damage to amino acid residues in proteins. (PMID: 1621954, 6366787) [HMDB] Aminomalonic acid is an amino endogenous metabolite, acts as a strong inhibitor of L-asparagine synthetase from Leukemia 5178Y/AR (Ki= 0.0023 M) and mouse pancreas (Ki= 0.0015 M) in vitro. Aminomalonic acid is a potential biomarker to discriminate between different stages of melanoma metastasis[1][2][3].

L-2-Amino-4-methylenepentanedioic acid

4-Methyleneglutamic acid, sodium salt, (L-glu)-isomer

C6H9NO4 (159.0532)

L-2-Amino-4-methylenepentanedioic acid is found in alcoholic beverages. L-2-Amino-4-methylenepentanedioic acid is a constituent of peanuts (Arachis hypogaea) and other plants, notably tulips and hops

2-Aminoacrylic acid

Anhydroserine2-aminopropenoic acid

C3H5NO2 (87.032)

Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid). [HMDB] Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid).

2-Aminomuconic acid

(2Z,4E)-5-aminohexa-2,4-dienedioic acid

C6H7NO4 (157.0375)

2-Aminomuconic acid is a product of the Tryptophan metabolism degradation pathway (kinurenine pathway), in a reaction catabolized by the enzyme aminocarboxymuconate semialdehyde decarboxylase [EC:4.1.1.45]. The kynurenine pathway is the major route of L-tryptophan degradation in mammals. (BioCyc) [HMDB] 2-Aminomuconic acid is a product of the Tryptophan metabolism degradation pathway (kinurenine pathway), in a reaction catabolized by the enzyme aminocarboxymuconate semialdehyde decarboxylase [EC:4.1.1.45]. The kynurenine pathway is the major route of L-tryptophan degradation in mammals. (BioCyc).

2-Aminomuconic acid semialdehyde

(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid

C6H7NO3 (141.0426)

2-aminomuconic semialdehyde is an intermediate in the oxidative metabolism of tryptophan in mammals, and takes place via the kynurenine pathway, which is also used for NAD biosynthesis in all eukaryotic organisms. 2-Aminomuconic semialdehyde is reported to be unstable and spontaneously converted to picolinic acid (regarded as metabolically inert and is excreted in the urine as a glycine conjugate), and enzymatically converted to 2-aminomuconic acid through the action of 2-aminomuconic semialdehyde dehydrogenase. (PMID: 10510494, 16267312, 14275129) [HMDB] 2-aminomuconic semialdehyde is an intermediate in the oxidative metabolism of tryptophan in mammals, and takes place via the kynurenine pathway, which is also used for NAD biosynthesis in all eukaryotic organisms. 2-Aminomuconic semialdehyde is reported to be unstable and spontaneously converted to picolinic acid (regarded as metabolically inert and is excreted in the urine as a glycine conjugate), and enzymatically converted to 2-aminomuconic acid through the action of 2-aminomuconic semialdehyde dehydrogenase. (PMID: 10510494, 16267312, 14275129).

L-2-Aminoethyl seryl phosphate

2-amino-3-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}propanoic acid

C5H13N2O6P (228.0511)

L-2-Aminoethyl seryl phosphate is found in animal foods. L-2-Aminoethyl seryl phosphate is isolated from numerous animals including chicken, fish and reptile Isolated from numerous animals including chicken, fish and reptiles. L-2-Aminoethyl seryl phosphate is found in fishes and animal foods.

Thiomorpholine 3-carboxylate

1,4-Thiomorpholine-3-carboxylic acid

C5H9NO2S (147.0354)

Thiomorpholine 3-carboxylate is a substrate for: Thiomorpholine-carboxylate dehydrogenase.

2-Amino-3-carboxymuconic acid semialdehyde

(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid

C7H7NO5 (185.0324)

2-Amino-3-carboxymuconic acid semialdehyde (CAS: 16597-58-3) is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic acid semialdehyde is enzymatically converted into 2-aminomuconate via 2-aminomuconic semialdehyde (PMID: 10510494, 16267312, 14275129). 2-amino-3-carboxymuconic acid semialdehyde is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic semialdehyde is enzymatically converted to 2-aminomuconate via 2-aminomuconic semialdehyde. (PMID: 10510494, 16267312, 14275129) [HMDB]

Buthionine sulfoximine

2-amino-4-[butyl(imino)oxo-lambda6-sulfanyl]butanoic acid

C8H18N2O3S (222.1038)

Buthionine Sulfoximine is a synthetic amino acid. Buthionine sulfoximine irreversibly inhibits gamma-glutamylcysteine synthase, thereby depleting cells of glutathione, a metabolite that plays a critical role in protecting cells against oxidative stress, and resulting in free radical-induced apoptosis. Elevated glutathione levels are associated with tumor cell resistance to alkylating agents and platinum compounds. By depleting cells of glutathione, this agent may enhance the in vitro and in vivo cytotoxicities of various chemotherapeutic agents in drug-resistant tumors. Buthionine sulfoximine may also exhibit antiangiogenesis activity. (NCI04) D020011 - Protective Agents > D011837 - Radiation-Protective Agents D009676 - Noxae > D000963 - Antimetabolites D011838 - Radiation-Sensitizing Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors Buthionine sulfoximine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=5072-26-4 (retrieved 2024-09-04) (CAS RN: 5072-26-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

2-Amino-3-oxoadipate

2-amino-3-oxo-hexanedioic acid

C6H9NO5 (175.0481)

This compound belongs to the family of 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).

Selenocystine

2-amino-3-[(2-amino-2-carboxyethyl)diselanyl]propanoic acid

C6H12N2O4Se2 (335.9127)

Selenocystine, also known as 3,3-diselenodialanine, belongs to the class of organic compounds known as alpha-amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxyl group (alpha carbon). More specifically, selenocystine is a diselenide consisting of two selenoamino acids that are attached together at their selenium atoms. This particular selenoamino acid is selenocysteine, the selenium analogue to cysteine (selenium being the element directly beneath sulphur in the periodic table); likewise, selenocystine is the selenium analogue to cystine. Since each constituent amino acid has a stereocentre, there are three different stereoisomers of selenocystine: D-selenocystine, L-selenocystine, and meso-selenocystine, the first two of which are optically active. Like other amino acids, L-selenocystine is the most common form within organisms; however, the D- and meso- forms have also been found (PMID: 30920149). Selenocystine is a solid that is moderately soluble in water. Due to the reactivity of selenocysteine, it is rarely encountered; rather, cells store selenium in the less reactive oxidized form of selenocystine or in a methylated form, such as selenomethionine (DOI: 10.1007/978-3-319-92405-2_3). When cells are grown in the absence of selenium, translation of selenoproteins terminates at the UGA codon, resulting in a truncated, non-functional enzyme. Unlike other amino acids present in biological proteins, selenocysteine is not coded for directly in the genetic code. Rather, the tRNA-bound seryl residue is converted to a selenocysteine residue by the pyridoxal phosphate-containing enzyme selenocysteine synthase (PMID: 17194211). Kurt Franke et al. indicated that there was evidence that selenium was in a form similar to that of cysteine, predating Thressa Stadtman’s discovery of the 21st amino acid by four decades (PMID: 26949981; J. Biol. Chem. 111:643). Selenocysteine may be denoted by the short forms Sec, U, or SeCys (Cys is used for cysteine), whereas selenocystine may be denoted by SeCys2. However, the literature sometimes uses SeCys for selenocystine and may cause confusion. Selenocystine has been found in animals, plants, and bacteria. It is being researched as treatment for cancer and for its antioxidant properties (PMID: 24763048, 24030774). Selenium, in its various forms such as selenocystine, is essential for many species, including humans, yet it is also toxic to all organisms; hence, it has come to be referred to as the “essential poison” (PMID: 26949981; 6679541). Selenocystine is a substrate for glutathione peroxidase 1. [HMDB] D000890 - Anti-Infective Agents > D000998 - Antiviral Agents L-Selenocystine is a diselenide-bridged amino acid. L-Selenocystine is a redox-active selenium compound that has both anti- and pro-oxidant actions. L-Selenocystine induces an unfolded protein response, ER stress, and large cytoplasmic vacuolization in HeLa cells and has cytostatic effects in a range of cancer cell types[1].

Selenomethionine se-oxide

Butanoic acid, 2-amino-4-(methylseleninyl)-

C5H11NO3Se (212.9904)

This compound belongs to the family of 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).

(+)-threo-2-Amino-3,4-dihydroxybutanoic acid

C4H9NO4 (135.0532)

(+)-threo-2-Amino-3,4-dihydroxybutanoic acid is found in mushrooms. (+)-threo-2-Amino-3,4-dihydroxybutanoic acid is isolated from the mushroom Lyophyllum ulmariu

L-erythro-4-Hydroxyarginine

2-Amino-5-{[amino(imino)methyl]amino}-4-hydroxypentanoic acid

C6H14N4O3 (190.1066)

L-erythro-4-Hydroxyarginine is found in pulses. L-erythro-4-Hydroxyarginine occurs in the sea-cucumber (Polycheira rufescens) and in lentil seeds (Lens culinaris Occurs in the sea-cucumber (Polycheira rufescens) and in lentil seeds (Lens culinaris). L-erythro-4-Hydroxyarginine is found in pulses.

(S)-Isowillardiine

2-amino-3-(2-hydroxy-6-oxo-1,6-dihydropyrimidin-1-yl)propanoic acid

C7H9N3O4 (199.0593)

(S)-Isowillardiine is found in common pea. (S)-Isowillardiine is from seeds of Pisum sativum (peas From seeds of Pisum sativum (peas). (S)-Isowillardiine is found in pulses and common pea.

Tricholomic acid

alpha-Amino-3-oxo-5-isoxazolidineacetic acid, (r*,s*)-isomer

C5H8N2O4 (160.0484)

Tricholomic acid is found in mushrooms. Tricholomic acid is a constituent of the mushroom Tricholoma muscarium. Said to be useful as a flavouring substance Constituent of the mushroom Tricholoma muscarium. Said to be useful as a flavouring substance. Tricholomic acid is found in mushrooms.

Betalamic acid

(4Z)-4-(2-oxoethylidene)-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic 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

Humilixanthin

(4Z)-4-[(2E)-2-[(1-carboxy-4-hydroxybutyl)imino]ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

C14H18N2O7 (326.1114)

Iso. from the yellow-coloured root of beetroot Beta vulgaris. Humilixanthin is found in common beet and root vegetables. Humilixanthin is found in common beet. Iso. from the yellow-coloured root of beetroot Beta vulgaris.

Ibotenic acid

2-amino-2-(3-hydroxy-1,2-oxazol-5-yl)acetic acid

C5H6N2O4 (158.0328)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins Ibotenic acid has agonist activity at both the N-methyl-D-aspartate (NMDA) and trans-ACPD or metabolotropic quisqualate (Qm) receptor sites. Ibotenic acid has agonist activity at both the N-methyl-D-aspartate (NMDA) and trans-ACPD or metabolotropic quisqualate (Qm) receptor sites.

3-Oxoalanine

amino-(8CI)malonaldehydic acid

C3H5NO3 (103.0269)

Human lysosomal arylsulfate A (ASA) is a member of the sulfatase family which requires the posttranslational oxidation of thiol group of a cysteine that is conserved among all eukaryotic sulfatases, yielding 2-formylglycine. (PMID: 9521684) [HMDB] Human lysosomal arylsulfate A (ASA) is a member of the sulfatase family which requires the posttranslational oxidation of thiol group of a cysteine that is conserved among all eukaryotic sulfatases, yielding 2-formylglycine. (PMID: 9521684).

alpha-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID

2-amino-3-(5-methyl-3-oxo-2,3-dihydro-1,2-oxazol-4-yl)propanoic acid

C7H10N2O4 (186.0641)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists (RS)-AMPA ((±)-AMPA) is a glutamate analogue and a potent and selective excitatory neurotransmitter L-glutamic acid agonist. (RS)-AMPA does not interfere with binding sites for kainic acid or NMDA receptors[1][2].

2-Amino-5-phosphonopentanoic acid

C5H12NO5P (197.0453)

DL-AP5 (2-APV) is a competitive NMDA (N-methyl-D-aspartate) receptor antagonist. DL-AP5 shows significantly antinociceptive activity. DL-AP5 specifically blocks on channels in the rabbit retina[1][2][3].

Dopaxanthin quinone

(4E)-4-[(2E)-2-{[1-carboxy-2-(3,4-dioxocyclohexa-1,5-dien-1-yl)ethyl]imino}ethylidene]-1,2,3,4-tetrahydropyridine-2,6-dicarboxylic acid

C18H16N2O8 (388.0907)

Dopaxanthin quinone is produced by the reaction between dopaxanthin and oxygen, with water as a byproduct. A tyrosinase precursor enzyme catalyzes the reaction. [HMDB] Dopaxanthin quinone is produced by the reaction between dopaxanthin and oxygen, with water as a byproduct. A tyrosinase precursor enzyme catalyzes the reaction.

Iminodiacetate (IDA)

Iminodiacetic acid, calcium salt (1:1)

C4H7NO4 (133.0375)

Iminodiacetic acid (IDA) is a dicarboxylic acid amine. It is a strongly acidic compound that is very water soluble. It naturally exists as a white powder. IDA is food by-product or intermediate produced via the reaction of glycine with acrylamide through the heating, baking or frying of carbohydrate-rich foods such as potatoes (PMID: 25212154). Acrylamide is typically produced through a Maillard reaction (a heating reaction) of asparagine and various reducing sugars in plant-derived foods (PMID: 12368844). Concentrations of IDA are reduced in the plasma of individuals with autism (PMID: 33087514) and elevated in individuals with acute respiratory distress syndrome (ARDS) (PMID: 30779905). In addition to its role in metabolism, IDA has many industrial applications or roles. For instance, it is an important intermediate in the manufacture the herbicide glyphosate. IDA is also used in capillary electrophoresis for modulating peptide mobility and can be used as a precursor for the manufacture of the indicator xylenol orange. The iminodiacetate anion can act as a tridentate ligand to form a metal complex with two, fused, five membered chelate rings. The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100. Iminodiacetic acid is used in HIDA (hepatobiliary iminodiacetic acid) scans or cholescintigraphy scans, that employ the radionuclide Technetium 99m, to diagnose several diseases in the liver, gallbladder and bile duct. Iminodiacetic acid (IDA) is an polyamino carboxylic acid. The iminodiacetate anion can act as a tridentate ligand to form a metal complex with two, fused, five membered chelate rings. The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100. D064449 - Sequestering Agents > D002614 - Chelating Agents Iminodiacetic acid (IDA) is a chelating agent that strongly binds transition metals[1]. Iminodiacetic acid can be used for removal of toxic metal ions from water[2]. Iminodiacetic acid can serve as a biomarker to potentially predict the severity of ARDS (acute respiratory distress syndrome)[3].

L-alpha-Amino-5-oxo-2(5H)-isoxazolepropanoic acid

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

C6H8N2O4 (172.0484)

L-alpha-Amino-5-oxo-2(5H)-isoxazolepropanoic acid is found in pulses. L-alpha-Amino-5-oxo-2(5H)-isoxazolepropanoic acid is a amino acid from the roots of pea seedlings (Pisum species Amino acid from the roots of pea seedlings (Pisum subspecies). L-alpha-Amino-5-oxo-2(5H)-isoxazolepropanoic acid is found in pulses.

Ne,Ne dimethyllysine

2-amino-6-(dimethylamino)hexanoic acid

C8H18N2O2 (174.1368)

Ne,Ne dimethyllysine is an intermediate in lysine degradation. Ne,Ne dimethyllysine a methylated form of lysine found in histones that contributes to gene regulation.

O-phosphonato-L-homoserine(2-)

2-amino-4-(phosphonooxy)butanoic acid

C4H10NO6P (199.0246)

O-phosphonato-L-homoserine(2-) is considered to be soluble (in water) and acidic

Glufosinate

2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid

C5H12NO4P (181.0504)

D010575 - Pesticides > D006540 - Herbicides D004791 - Enzyme Inhibitors D016573 - Agrochemicals

2,4-Diaminobutyric acid

2,4-Diaminobutyric acid monohydrochloride, (+-)-isomer

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.

Bicine

N,N-Bis(2-hydroxyethyl)glycine, monosodium salt

C6H13NO4 (163.0845)

Bicine is a general purpose buffer for biological research. Useful pH range is 7.6 - 9.0. Its applications include: tissue culture,phosphorylation and photophosphorylation, fixative transmission electron microscopy, protein synthesis and preventing binding to non-receptor materials. It is a degradation product of alkanolamine and alkylalkanolamine solutions. [HMDB] . Bicine is a general purpose buffer for biological research. Useful pH range is 7.6 - 9.0. Its applications include: tissue culture,phosphorylation and photophosphorylation, fixative transmission electron microscopy, protein synthesis and preventing binding to non-receptor materials. It is a degradation product of alkanolamine and alkylalkanolamine solutions.

N-Methyl-a-aminoisobutyric acid

2-Methyl-2-(methylazaniumyl)propanoate

C5H11NO2 (117.079)

N-Methyl-a-aminoisobutyric acid, also known as 2-(methylamino)isobutyrate or AMAIB, 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). N-Methyl-a-aminoisobutyric acid is a drug. N-Methyl-a-aminoisobutyric acid is a metabolite that is actively incorporated into the cell by the actions of Interleukin 1-beta and Interleukin 6 via sodium dependent transport systems (PMID 16202926). N-Methyl-a-aminoisobutyric acid is a metabolite that is actively incorporated into the cell by the actions of Interleukin 1-beta and Interleukin 6 via sodium dependent transport systems (PMID 16202926) [HMDB]

2-aminooctanoate

DL-alpha-Amino-N-caprylic acid

C8H17NO2 (159.1259)

DL-2-Aminooctanoic acid, also known as a-aminocaprylate or alpha-aminocaprylic acid, 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). DL-2-Aminooctanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Outside of the human body, DL-2-Aminooctanoic acid has been detected, but not quantified in cow milk. alpha-Aminooctanoic acid is an amino compound found occasionally in human urine. (PMID: 13447222)

S-methylcysteine sulfoxide

2-Amino-3-methanesulphinylpropanoic acid

C4H9NO3S (151.0303)

(s)c(s)s-s-methylcysteine sulfoxide, also known as methiin, (dl-ala)-isomer or kale anemia factor, 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) (s)c(s)s-s-methylcysteine sulfoxide is soluble (in water) and a moderately acidic compound (based on its pKa). (s)c(s)s-s-methylcysteine sulfoxide can be found in brassicas, garden onion, and onion-family vegetables, which makes (s)c(s)s-s-methylcysteine sulfoxide a potential biomarker for the consumption of these food products. (S)C(S)S-S-Methylcysteine sulfoxide is found in brassicas. (S)C(S)S-S-Methylcysteine sulfoxide is a constituent of onion (Allium cepa), other Allium species and Brassica species. Potential nutriceutical

4-Carboxyphenylglycine

(+-)- alpha-Amino-4-carboxy-benzeneacetic acid

C9H9NO4 (195.0532)

4-Carboxyphenylglycine is a group I metabotropic glutamate receptor (mGlu) antagaonist by blocking the cystine/glutamate exchanger. In addition, it has modulating effect on the central action of NMDA receptor antagonist. It plays a role in synaptic plasticity and excitability, long term potentiation and long term depression. D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists

Betaine

(carboxymethyl)trimethylazanium

C5H11NO2 (117.079)

Betaine (CAS: 107-43-7), also known as N,N,N-trimethylglycine, was named after its discovery in sugar beet (Beta vulgaris) in the 19th century. It is a small N-trimethylated amino acid, existing in zwitterionic form at neutral pH. It is now often called glycine betaine to distinguish it from other betaines that are widely distributed in microorganisms, plants, and animals. Many naturally occurring betaines serve as organic osmolytes, substances synthesized or taken up from the environment by cells for protection against osmotic stress, drought, high salinity, or high temperature. Intracellular accumulation of betaines permits water retention in cells, thus protecting from the effects of dehydration (Wikipedia). Betaine functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. In particular, it methylates homocysteine to methionine, also producing N,N-dimethylglycine. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine comes from either the diet or by the oxidation of choline. Betaine insufficiency is associated with metabolic syndrome, lipid disorders, and diabetes, and may have a role in vascular and other diseases (PMID: 20346934). Betaine is important in development, from the pre-implantation embryo to infancy. Betaine is also widely regarded as an anti-oxidant. Betaine has been shown to have an inhibitory effect on NO release in activated microglial cells and may be an effective therapeutic component to control neurological disorders (PMID: 22801281). As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances (Martindale, The Extra Pharmacopoeia, 30th Ed, p1341). Betaine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-43-7 (retrieved 2024-07-01) (CAS RN: 107-43-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

gamma-Carboxyglutamic acid

1-aminopropane-1,3,3-tricarboxylic acid

C6H9NO6 (191.043)

Carboxyglutamic acid (or the conjugate base, carboxyglutamate), is an uncommon amino acid introduced into proteins by a post-translational carboxylation of glutamic acid residues. This modification is found, for example, in clotting factors and other proteins of the coagulation cascade. This modification introduces an affinity for calcium ions. In the blood coagulation cascade, Vitamin K is required to introduce gamma-carboxylation of clotting factors II, VII, IX, X and protein Z.

N-(1-Deoxy-b-D-fructopyranosyl) (R)C(S)S-alliin

3-(Prop-2-ene-1-sulphinyl)-2-{[(2,3,4,5-tetrahydroxyoxan-2-yl)methyl]amino}propanoic acid

C12H21NO8S (339.0988)

N-(1-Deoxy-b-D-fructopyranosyl) (R)C(S)S-alliin is found in onion-family vegetables. N-(1-Deoxy-b-D-fructopyranosyl) (R)C(S)S-alliin is isolated from garlic (Allium sativum). Isolated from garlic (Allium sativum) [DFC]. N-(1-Deoxy-b-D-fructopyranosyl) (R)C(S)S-alliin is found in garlic and onion-family vegetables.

Isoalliin

2-Amino-3-[(1Z)-prop-1-ene-1-sulphinyl]propanoic acid

C6H11NO3S (177.046)

Present in onion (Allium cepa). Isoalliin is found in many foods, some of which are mamey sapote, eggplant, common cabbage, and abiyuch. Isoalliin is found in garden onion. Isoalliin is present in onion (Allium cepa D000970 - Antineoplastic Agents D007004 - Hypoglycemic Agents

Indicaxanthin

(1E)-1-{2-[(4E)-2,6-dicarboxy-1,2,3,4-tetrahydropyridin-4-ylidene]ethylidene}-1λ⁵-pyrrolidin-1-ylium-2-carboxylate

C14H16N2O6 (308.1008)

Indicaxanthin is found in fruits. Indicaxanthin is a constituent of the fruits of Opuntia ficus-indica (Indian fig) Indicaxanthin is a type of betaxanthin, a plant pigment present in beets, prickly pear cactus, and a powerful antioxidant. It is also found in red dragonfruit D004396 - Coloring Agents > D050858 - Betalains

(3beta,4beta,5alpha,24Z)-4-Methylstigmasta-7,24(28)-dien-3-ol

2,6,15-trimethyl-14-[(5E)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol

C30H50O (426.3861)

Epicitrostadienol is a constituent of marigold flowers.

L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid

(alpha-Carboxycyclopropyl)glycine, (1R-(1alpha(s*),2alpha))-isomer

C6H9NO4 (159.0532)

L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid is found in fruits. L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid is isolated from seeds of Blighia sapida (akee apple Isolated from seeds of Blighia sapida (akee apple). L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid is found in fruits. D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists

(S)-alpha-Amino-4-carboxy-3-furanpropanoic acid

4-(2-amino-2-carboxyethyl)furan-3-carboxylic acid

C8H9NO5 (199.0481)

(S)-alpha-Amino-4-carboxy-3-furanpropanoic acid is found in mushrooms. (S)-alpha-Amino-4-carboxy-3-furanpropanoic acid is isolated from the unpalatable mushrooms Phyllotopsis nidulans and Tricholomopsis rutilan

L-Gizzerosine

2-amino-6-{[2-(1H-imidazol-5-yl)ethyl]amino}hexanoic acid

C11H20N4O2 (240.1586)

L-Gizzerosine is isolated from mackerel meal. L-Gizzerosine is produced as a contaminant during fish meal manufacturing by reaction between histidine and protein in the fish meat. Causes gizzard erosion ("black vomit") in chicks. Isolated from mackerel meal. Production as a contaminant during fish meal manufacturing by reaction between histidine and protein in the fish meat. Causes gizzard erosion ("black vomit") in chicks

(2S,4S)-Monatin

(2S,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic acid

C14H16N2O5 (292.1059)

(2S,4S)-Monatin is a constituent of the roots of Schlerochiton ilicifolius. High intensity sweetener. Constituent of the roots of Schlerochiton ilicifolius. High intensity sweetener

Mytilin B

(2R,3S)-2-{[(1Z)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-hydroxybutanoic acid

C14H22N2O8 (346.1376)

Mytilin B is found in mollusks. Mytilin B is isolated from the edible mussel Mytilus galloprovincialis as a 1:3 inseparable mixture with Mytilin A LLF12-R. Isolated from the edible mussel Mytilus galloprovincialis as a 1:3 inseparable mixture with Mytilin A LLF12-R. Mytilin B is found in mollusks.

L-Acetopine

5-carbamimidamido-2-[(carboxymethyl)amino]pentanoic acid

C8H16N4O4 (232.1171)

L-Acetopine is found in fats and oils. L-Acetopine is isolated from calluses of soybean plant and coHon (Gossypium hirsutum). Isolated from calluses of soybean plant and coHon (Gossypium hirsutum). L-Acetopine is found in fats and oils and pulses.

3-(Carboxymethylamino)propanoic acid

3-[(carboxymethyl)amino]propanoic acid

C5H9NO4 (147.0532)

3-(Carboxymethylamino)propanoic acid is found in pulses. 3-(Carboxymethylamino)propanoic acid is isolated from Phaseolus radiatus var. typicus. Isolated from Phaseolus radiatus variety typicus. 3-(Carboxymethylamino)propanoic acid is found in pulses.

Lycoperdic acid

a-Amino-2-carboxytetrahydro-5-oxo-2-furanpropanoic acid, 9ci

C8H11NO6 (217.0586)

Lycoperdic acid is found in mushrooms. Lycoperdic acid is isolated from the mushroom Lycoperdon perlatum (common puffball

Merodesmosine

(5E)-2,10-diamino-5-{[(5-amino-5-carboxypentyl)amino]methyl}undec-5-enedioic acid

C18H34N4O6 (402.2478)

Aminoacid from reduced elastin. Merodesmosine is found in animal foods. Merodesmosine is found in animal foods. Aminoacid from reduced elasti

(S)-Spinacine

4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid

C7H9N3O2 (167.0695)

(S)-Spinacine is found in beverages. (S)-Spinacine is isolated from the crab (Crango vulgaris), from the liver of the shark (Acanthias vulgaris) and from spinach. Also isolated from the roots of Panax ginsen Spinacine is an endogenous metabolite.

N6-Acetyl-5S-hydroxy-L-lysine

2-Amino-5-hydroxy-6-[(1-hydroxyethylidene)amino]hexanoate

C8H16N2O4 (204.111)

N6-Acetyl-5S-hydroxy-L-lysine is found in root vegetables. N6-Acetyl-5S-hydroxy-L-lysine is produced by Beta vulgaris (sugar beet). Production by Beta vulgaris (sugar beet). N6-Acetyl-5S-hydroxy-L-lysine is found in root vegetables.

2-Amino-4-ethoxy-3-hydroxybutanoic acid

C6H13NO4 (163.0845)

2-Amino-4-ethoxy-3-hydroxybutanoic acid is found in mushrooms. 2-Amino-4-ethoxy-3-hydroxybutanoic acid is isolated from the mushroom Lyophyllum ulmarium. Isolated from the mushroom Lyophyllum ulmarium. 2-Amino-4-ethoxy-3-hydroxybutanoic acid is found in mushrooms.

3beta-Cycloartane-3,25-diol

15-(6-hydroxy-6-methylheptan-2-yl)-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C30H52O2 (444.3967)

3beta-Cycloartane-3,25-diol is found in cereals and cereal products. 3beta-Cycloartane-3,25-diol is a constituent of mature wheat straw (Triticum aestivum).

DL-Ornithino-L-alanine

2-amino-5-[(2-amino-2-carboxyethyl)amino]pentanoic acid

C8H17N3O4 (219.1219)

DL-Ornithino-L-alanine is found in milk and milk products. DL-Ornithino-L-alanine is a amino acid formed by alkaline hydrolysis of silk, wool and other proteins, especially lactalbumin and caseins. DL-Ornithino-L-alanine is present in Mozzarella chees

Lysinoalanine

2-amino-6-[(2-amino-2-carboxyethyl)amino]hexanoic acid

C9H19N3O4 (233.1375)

Nephrotoxic food contaminan

L-trans-5-Hydroxy-2-piperidinecarboxylic acid

(2S,5R)-trans-5-Hydroxypiperidine-2-carboxylic acid

C6H11NO3 (145.0739)

L-cis-5-Hydroxy-2-piperidinecarboxylic acid is found in fruits. L-cis-5-Hydroxy-2-piperidinecarboxylic acid is present in the leaves of Morus alba (white mulberry

L-Furosine

N-[[3-oxo-2-(2-Pentenyl)cyclopentyl]acetyl]isoleucine, 9ci

L-Furosine is an analytical indicator of heat treatment damage or storage deterioriation in milk, dried foods, pasta, tomato paste and eggs. Acid hydrolysis product of the Amadori compoun

Medicanine

1-(3-hydroxypropyl)azetidine-2-carboxylic acid

C7H13NO3 (159.0895)

Medicanine is found in pulses. Medicanine is a amino acid from seeds of Medicago sativa (alfalfa). Amino acid from seeds of Medicago sativa (alfalfa). Medicanine is found in pulses.

4-Hydroxycitrulline

2-amino-4-hydroxy-5-[(C-hydroxycarbonimidoyl)amino]pentanoic acid

C6H13N3O4 (191.0906)

4-Hydroxycitrulline is found in pulses. 4-Hydroxycitrulline is isolated from Vicia fab

L-Oxalylalbizziine

2-Amino-3-{n-[carboxy(hydroxy)methylidene]-(C-hydroxycarbonimidoyl)amino}propanoate

C6H9N3O6 (219.0491)

L-Oxalylalbizziine is isolated from seeds of Acacia catechu (black catechu). Isolated from seeds of Acacia catechu (black catechu)

L-Agaridoxin

2-Amino-4-[(3,4-dihydroxyphenyl)-C-hydroxycarbonimidoyl]butanoate

C11H14N2O5 (254.0903)

L-Agaridoxin is found in mushrooms. L-Agaridoxin is a constituent of Agaricus campestris (field mushroom)

L-2-Amino-3-methylenehexanoic acid

C7H13NO2 (143.0946)

L-2-Amino-3-methylenehexanoic acid is found in mushrooms. L-2-Amino-3-methylenehexanoic acid is found in carpophores of Amanita vaginata (grisette

2-Aminoheptanedioic acid

DL-2-Aminopimelic acid(alpha-)

C7H13NO4 (175.0845)

2-Aminoheptanedioic acid is found in beverages. 2-Aminoheptanedioic acid is isolated from Ceratonia siliqua (carob Isolated from Ceratonia siliqua (carob). 2-Aminoheptanedioic acid is found in beverages and fruits.

Ethiin

2-Amino-3-(ethanesulphinyl)propanoic acid

C5H11NO3S (165.046)

Constituent of numerous Allium subspecies Ethiin is found in many foods, some of which are sour cherry, wax gourd, arrowroot, and silver linden. Ethiin is found in onion-family vegetables. Ethiin is a constituent of numerous Allium species.

(R)C(R)S-S-Propylcysteine sulfoxide

2-Amino-3-(propane-1-sulphinyl)propanoic acid

C6H13NO3S (179.0616)

(R)C(S)S-S-Propylcysteine sulfoxide is found in onion-family vegetables. (R)C(S)S-S-Propylcysteine sulfoxide is a constituent of onions (Allium cepa) and other Allium species Occurs free in onion bulbs (Allium cepa). (R)C(R)S-S-Propylcysteine sulfoxide is found in garden onion and onion-family vegetables.

N5-(4-Methoxybenzyl)glutamine

2-Amino-4-{[(4-methoxyphenyl)methyl]-C-hydroxycarbonimidoyl}butanoate

C13H18N2O4 (266.1267)

N5-(4-Methoxybenzyl)glutamine is found in fruits. N5-(4-Methoxybenzyl)glutamine is a constituent of the xylem sap of the roots of Cucurbita maxima x Cucurbita moschata. Constituent of the xylem sap of the roots of Cucurbita maxima x Cucurbita moschata. N5-(4-Methoxybenzyl)glutamine is found in fruits and japanese pumpkin.

L-Pyridosine

2-amino-6-(5-hydroxy-2-methyl-4-oxo-1,4-dihydropyridin-1-yl)hexanoic acid

L-Pyridosine is found in milk and milk products. Acid hydrolysis product of heated milk. Marker for heat treatment of milk and other foodstuff

L-2-Amino-5-hydroxypentanoic acid

2-Amino-5-hydroxyvaleric acid, (DL)-isomer

C5H11NO3 (133.0739)

L-2-Amino-5-hydroxypentanoic acid is found in pulses. L-2-Amino-5-hydroxypentanoic acid is present in jack bean seeds (Canavalia ensiformis

Syndesine

2-amino-6-[(E)-(5-amino-5-carboxy-2-hydroxypentylidene)amino]-5-hydroxyhexanoic acid

C12H23N3O6 (305.1587)

Syndesine is found in animal foods. Syndesine is an intramolecular crosslink of collagen. An intramolecular crosslink of collagen. Syndesine is found in animal foods.

Majoroside F6

2-{[2-({5,16-dihydroxy-14-[(4E)-6-hydroxy-6-methyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hept-4-en-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-yl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

C48H82O19 (962.545)

Majoroside F6 is found in tea. Majoroside F6 is a constituent of Panax japonicus var. major Widely distributed in plants, e.g. beetroot. Flavouring ingredient. Dietary supplement

O-Ureidohomoserine

2-amino-4-{[(C-hydroxycarbonimidoyl)amino]oxy}butanoic acid

C5H11N3O4 (177.075)

O-Ureidohomoserine is involved in the canavanine biosynthesis pathway. It can be generated from the enzymatic reduction of canavaninosuccinate or enzymatic oxidation of L-canaline. The canavanine biosynthesis pathway is analogous to the animal Krebs-Henseleit ornithine-urea cycle. Feeding experiments demonstrated the existence of enzyme activities of canaline-dependent ornithine carbamyltransferase, ureidohomoserine-dependent argininosuccinate synthetase, and canavaninosuccinate-dependent argininosuccinate lyase in Canavalia lineate. The canaline-dependent ornithine carbamyltransferase has been purified subsequently. The synthesis of ureidohomoserine is probably the rate-limiting step. Ureidohomoserine interacted with canaline or canavanine to affect synergistically L. minor growth by enhancing individual canavanine or canaline toxicity and increasing the additive growth reduction caused by canavanine plus canaline. The ornithineurea cycle amino acids effectively counteracted both the additive and synergistic growth-inhibiting properties of the canaline-urea cycle compounds.(PMID: 16659513). O-Ureidohomoserine is involved in the canavanine biosynthesis pathway. It can be generated from the enzymatic reduction of canavaninosuccinate or enzymatic oxidation of L-canaline.

DL-O-Phosphoserine

DL-Serine, dihydrogen phosphoric acid (ester)

C3H8NO6P (185.0089)

DL-O-Phosphoserine, also known as DL-O-phosphorylserine or DL-O-serine phosphate, 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). Serine proteases are a common type of protease. DL-O-Phosphoserine exists in all living species, ranging from bacteria to humans. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. It is a normal metabolite found in human biofluids. (PMID 7693088, 7688003) DL-O-Phosphoserine, a normal metabolite in human biofluid, is an ester of serine and phosphoric acid.

Homolanthionine

2-Amino-4-(3-amino-3-carboxypropanesulphonyl)butanoic acid

C8H16N2O6S (268.0729)

Homolanthionine is formed from homocysteine and homoserine by a condensation analogous to that normally leading to cystathionine. The only other known occurrence of homolanthionine in nature is in a methionine-requiring mutant strain of Escherichia coli. Patients with homocystinuria excrete small amounts of L-homolanthionine in their urine. [HMDB] Homolanthionine is formed from homocysteine and homoserine by a condensation analogous to that normally leading to cystathionine. The only other known occurrence of homolanthionine in nature is in a methionine-requiring mutant strain of Escherichia coli. Patients with homocystinuria excrete small amounts of L-homolanthionine in their urine.

Homocysteinesulfinic acid

Homocysteinesulfinic acid, (D)-isomer

C4H9NO4S (167.0252)

Homocysteinesulfinic acid, is involved in many metabolic pathways including trans-sulfuration in cysteine synthesis, re-methylation in methionine synthesis,. trans-methylation of DNA, proteins, and lipids, and biosynthesis of small hormonal and neuronal signaling molecules. Homocysteinesulfinic acid, is involved in many metabolic pathways including trans-sulfuration in cysteine synthesis, re-methylation in methionine synthesis,

N(6)-(Octanoyl)lysine

2-Amino-6-[(1-hydroxyoctylidene)amino]hexanoate

C14H28N2O3 (272.21)

N(6)-(Octanoyl)lysine is a modified lysine amino acid that is normally found in acyl carrier protein. The enzyme lipoyl(octanoyl) transferase (EC 2.3.1.181) catalyzes this amino acid residue modification with the following reaction:. octanoyl-[acyl-carrier-protein] + protein <-> protein N6-(octanoyl)lysine + acyl carrier protein. In other words, it catalyzes the transfer of endogenously produced octanoic acid from octanoyl-acyl-carrier-protein onto the lipoyl domains of lipoate-dependent enzymes. Another enzyme called lipoyl synthase (EC 2.8.1.8) catalyzes the chemical reaction:. protein N6-(octanoyl)lysine + 2 sulfur + 2 S-adenosyl-L-methionine <-> protein N6-(lipoyl)lysine + 2 L-methionine + 2 5-deoxyadenosine. In other words, this enzyme catalyzes the radical-mediated insertion of two sulfur atoms into the C-6 and C-8 positions of the octanoyl moiety bound to the lipoyl domains of lipoate-dependent enzymes, thereby converting the octanoylated domains into lipoylated derivatives. Degradation of acyl carrier protein or of lipoate derivatized proteins will lead to free N(6)-(Octanoyl)lysine. N(6)-(Octanoyl)lysine is a modified lysine amino acid that is normally found in acyl carrier protein. The enzyme lipoyl(octanoyl) transferase (EC 2.3.1.181) catalyzes this amino acid residue modification with the following reaction:

Gadodiamide

3,13-bis(methylamino)-16,19,22-trioxo-2lambda4,14lambda4,15,20,23-pentaoxa-5lambda5,8lambda5,11lambda5-triaza-1-gadolinaheptacyclo[6.6.3.3^{1,5}.3^{1,11}.0^{1,5}.0^{1,8}.0^{1,11}]tricosa-2,13-diene-2,5,8,11,14-pentakis(ylium)-1-uide

C16H26GdN5O8 (574.1022)

Gadodiamide is only found in individuals that have used or taken this drug. It is a gadolinium based contrast agent used in MR imaging procedures to assist in the visualization of blood vessels. It is commonly marketed under the trade name Omniscan. [Wikipedia]Based on the behavior of protons when placed in a strong magnetic field, which is interpreted and transformed into images by magnetic resonance (MR) instruments. Paramagnetic agents have unpaired electrons that generate a magnetic field about 700 times larger than the protons field, thus disturbing the protons local magnetic field. When the local magnetic field around a proton is disturbed, its relaxation process is altered. MR images are based on proton density and proton relaxation dynamics. MR instruments can record 2 different relaxation processes, the T1 (spin-lattice or longitudinal relaxation time) and the T2 (spin-spin or transverse relaxation time). In magnetic resonance imaging (MRI), visualization of normal and pathological brain tissue depends in part on variations in the radiofrequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in the T2. When placed in a magnetic field, gadodiamide shortens both the T1 and the T2 relaxation times in tissues where it accumulates. At clinical doses, gadodiamide primarily affects the T1 relaxation time, thus producing an increase in signal intensity. Gadodiamide does not cross the intact blood-brain barrier; therefore, it does not accumulate in normal brain tissue or in central nervous system (CNS) lesions that have not caused an abnormal blood-brain barrier (e.g., cysts, mature post-operative scars). Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadodiamide in lesions such as neoplasms, abscesses, and subacute infarcts.

Gadoteridol

3-methyl-16,19,24-trioxo-2,17,18,25-tetraoxa-5lambda5,8lambda5,11lambda5,14lambda5-tetraaza-1-gadolinaoctacyclo[9.6.3.3^{1,8}.2^{5,14}.0^{1,5}.0^{1,8}.0^{1,11}.0^{1,14}]pentacosan-2-ium-5,8,11,14-tetrakis(ylium)-1,1-diuide

C17H29GdN4O7 (559.1277)

Gadoteridol provides contrast enhancement of the brain, spine and surrounding tissues resulting in improved visualization (compared with unenhanced MRI) of lesions with abnormal vascularity or those thought to cause a disruption of the normal blood brain barrier. Gadoteridol can also be used for whole body contrast enhanced MRI including the head, neck, liver, breast, musculoskeletal system and soft tissue pathologies. n MRI, visualization of normal and pathological brain tissue depends in part on variations in the radiofrequency signal intensity that occur with changes in proton density, alteration of the T1, and variation in T2. When placed in a magnetic field, gadoteridol shortens the T1 relaxation time in tissues where it accumulates. Abnormal vascularity or disruption of the blood-brain barrier allows accumulation of gadoteridol in lesions such as neoplasms, abscesses, and subacute infarcts. V - Various > V08 - Contrast media > V08C - Magnetic resonance imaging contrast media > V08CA - Paramagnetic contrast media

Gadobutrol

4,7,10-tris(carboxymethyl)-1-[(2S,3R)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetraaza-13-gadolinatetracyclo[5.5.1.0^{4,13}.0^{10,13}]tridecane-1,4,7,10-tetraium-13-uide

C18H31GdN4O9 (605.1332)

Gadobutrol is only found in individuals that have used or taken this drug.It is a contrast agent used in magnetic resonance imaging (MRI). V - Various > V08 - Contrast media > V08C - Magnetic resonance imaging contrast media > V08CA - Paramagnetic contrast media

L-Nicotianine

1-(3-amino-3-carboxypropyl)pyridin-1-ium-3-carboxylate

C10H12N2O4 (224.0797)

L-Nicotianine is found in mushrooms. L-Nicotianine is a constituent of Lentinus edodes (shiitake)

(3-Nitroamino)alanine

2-amino-3-(nitroamino)propanoic acid

C3H7N3O4 (149.0437)

(3-Nitroamino)alanine is found in mushrooms. (3-Nitroamino)alanine is isolated from Agaricus silvaticus (red staining mushroom

gamma-Glutaminyl-4-hydroxybenzene

4-(C-hydroxycarbonimidoyl)-2-[(4-hydroxyphenyl)amino]butanoic acid

C11H14N2O4 (238.0954)

gamma-Glutaminyl-4-hydroxybenzene is found in mushrooms. gamma-Glutaminyl-4-hydroxybenzene is isolated from the gill tissue of the edible mushrooms Agaricus bisporus (button mushroom) and Agaricus hortensi

Pyrraline

2-amino-6-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]hexanoic acid

Pyrraline is Maillard produced, obtained by reaction between BCS47-B and HHS42-T. Maillard production obtained by reacn. between BCS47-B and HHS42-T.

(S)-Argpyrimidine

2-Amino-5-[(5-hydroxy-4,6-dimethyl-1,2-dihydropyrimidin-2-ylidene)amino]pentanoate

C11H18N4O3 (254.1379)

(S)-Argpyrimidine is found in alcoholic beverages. (S)-Argpyrimidine is found in beer.

Aldosine

5-(6-Carboxy-2-piperidinyl)-1,2,3,4-tetrahydro-2-pyridinecarboxylic acid, 9ci

Aldosine is found in animal foods. Aldosine is a hydrolysis product from the aldol crosslinks of bovine elastin and collagen. Hydrolysis product from the aldol crosslinks of bovine elastin and collagen. Aldosine is found in animal foods.

L-Dopaquinone

2-amino-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

C9H9NO4 (195.0532)

Implicated in food discolouration (enzymatic browning). Implicated in food discolouration (enzymatic browning)

Neoliquiritin 2'-apioside

7-[(3-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

C26H30O13 (550.1686)

Neoliquiritin 2-apioside is found in herbs and spices. Neoliquiritin 2-apioside is a constituent of Glycyrrhiza glabra (licorice). Constituent of Glycyrrhiza glabra (licorice). Neoliquiritin 2-apioside is found in tea and herbs and spices. Liquiritigenin-7-O-β-D-glucopyranosyl-(1→2)-β-D-apiofuranoside (Liquiritigenin-7-apiosylglucoside) is a flavonoid isolated from the roots of Glycyrrhiza, has weaker cytotoxicity against several tumor cells and normal cells[1].

L-alpha-Amino-1H-pyrrole-1-hexanoic acid

C10H16N2O2 (196.1212)

L-alpha-Amino-1H-pyrrole-1-hexanoic acid is found in animal foods. L-alpha-Amino-1H-pyrrole-1-hexanoic acid is widely distributed in fresh foodstuffs, e.g. meats, fish, vegetables, nuts, and processed foods. L-alpha-Amino-1H-pyrrole-1-hexanoic acid is a component of nonenzymic browning reaction models. Widely distributed in fresh foodstuffs, e.g. meats, fish, vegetables, nuts, and processed foods. Component of nonenzymic browning reaction models. L-alpha-Amino-1H-pyrrole-1-hexanoic acid is found in many foods, some of which are green vegetables, animal foods, fishes, and nuts.

Fructoseglycine

2-{[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]amino}acetic acid

C8H15NO7 (237.0848)

Fructoseglycine, a fructose molecule containing a glycine group in place of a hydroxyl group.

N-(2-Carboxymethyl)-morpholine

C6H11NO3 (145.0739)

N-(2-Carboxymethyl)-morpholine is a metabolite of mycophenolate mofetil. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine. It is a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH) in purine biosynthesis which is necessary for the growth of T cells and B cells. Other cells are able to recover purines via a separate, scavenger, pathway and are, thus, able to escape the effect. MMF is a less toxic alternative to azathioprine. (Wikipedia)

Pyroglutamylglycine

2-amino-3-(5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl)-3-oxopropanoic acid

C7H10N2O4 (186.0641)

Pyroglutamylglycine 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).

N-phosphocreatinate(2-)

[amino(phosphonoamino)methylidene](carboxymethyl)methylazanium

C4H11N3O5P+ (212.0436)

N-phosphocreatinate(2-) is classified as a member of the 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). N-phosphocreatinate(2-) is considered to be soluble (in water) and acidic

6-(2-amino-2-carboxyethyl)-4-hydroxybenzothiazole

2-amino-3-(4-hydroxy-1,3-benzothiazol-6-yl)propanoic acid

C10H10N2O3S (238.0412)

6-(2-amino-2-carboxyethyl)-4-hydroxybenzothiazole is considered to be practically insoluble (in water) and acidic

1-hydroxyhexanoylglycine

2-[(carboxymethyl)amino]hexanoic acid

C8H15NO4 (189.1001)

1-Hydroxyhexanoylglycine is classified as a member of the 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). 1-Hydroxyhexanoylglycine is considered to be soluble (in water) and acidic.Ã‚Â

2-Hepteneoylglycine

2-amino-3-oxonon-4-enoic acid

C9H15NO3 (185.1052)

2-Hepteneoylglycine is classified as a member of the 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). 2-Hepteneoylglycine is considered to be slightly soluble (in water) and acidic.

1-hydroxyoct-2-enoylglycine

2-[(carboxymethyl)amino]oct-2-enoic acid

1-Hydroxyoct-2-enoylglycine is classified as a member of the 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). 1-Hydroxyoct-2-enoylglycine is considered to be practically insoluble (in water) and acidic.

1-hydroxyoct-3-enoylglycine

2-[(carboxymethyl)amino]oct-3-enoic acid

1-Hydroxyoct-3-enoylglycine is classified as a member of the 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). 1-Hydroxyoct-3-enoylglycine is considered to be slightly soluble (in water) and acidic.

1-hydroxyoct-4-enoylglycine

2-[(carboxymethyl)amino]oct-4-enoic acid

1-Hydroxyoct-4-enoylglycine is classified as a member of the 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). 1-Hydroxyoct-4-enoylglycine is considered to be slightly soluble (in water) and acidic.

1-hydroxyoct-5-enoylglycine

2-[(carboxymethyl)amino]oct-5-enoic acid

1-Hydroxyoct-5-enoylglycine is classified as a member of the 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). 1-Hydroxyoct-5-enoylglycine is considered to be slightly soluble (in water) and acidic.

1-hydroxyoct-6-enoylglycine

2-[(carboxymethyl)amino]oct-6-enoic acid

1-Hydroxyoct-6-enoylglycine is classified as a member of the 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). 1-Hydroxyoct-6-enoylglycine is considered to be slightly soluble (in water) and acidic.

1-hydroxyoct-7-enoylglycine

2-[(carboxymethyl)amino]oct-7-enoic acid

1-Hydroxyoct-7-enoylglycine is classified as a member of the 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). 1-Hydroxyoct-7-enoylglycine is considered to be slightly soluble (in water) and acidic.

2-hydroxyoct-1-enoylglycine

2-[(2-hydroxy-1-oxooct-1-en-3-yl)amino]acetic acid

2-Hydroxyoct-1-enoylglycine is classified as a member of the 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). 2-Hydroxyoct-1-enoylglycine is considered to be slightly soluble (in water) and acidic.

3-hydroxyoct-1-enoylglycine

2-[(3-hydroxy-1-oxooct-1-en-2-yl)amino]acetic acid

3-Hydroxyoct-1-enoylglycine is classified as a member of the 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). 3-Hydroxyoct-1-enoylglycine is considered to be slightly soluble (in water) and acidic.

4-hydroxyoct-1-enoylglycine

2-[(4-hydroxy-1-oxooct-1-en-2-yl)amino]acetic acid

4-Hydroxyoct-1-enoylglycine is classified as a member of the 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). 4-Hydroxyoct-1-enoylglycine is considered to be slightly soluble (in water) and acidic.

5-hydroxyoct-1-enoylglycine

2-[(5-hydroxy-1-oxooct-1-en-2-yl)amino]acetic acid

5-Hydroxyoct-1-enoylglycine is classified as a member of the 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). 5-Hydroxyoct-1-enoylglycine is considered to be slightly soluble (in water) and acidic.

6-hydroxyoct-1-enoylglycine

2-[(6-hydroxy-1-oxooct-1-en-2-yl)amino]acetic acid

6-Hydroxyoct-1-enoylglycine is classified as a member of the 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). 6-Hydroxyoct-1-enoylglycine is considered to be slightly soluble (in water) and acidic.

7-hydroxyoct-1-enoylglycine

2-[(7-hydroxy-1-oxooct-1-en-2-yl)amino]acetic acid

7-Hydroxyoct-1-enoylglycine is classified as a member of the 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). 7-Hydroxyoct-1-enoylglycine is considered to be slightly soluble (in water) and acidic.

1,2-octadienoylglycine

2-[(1-oxoocta-1,2-dien-3-yl)amino]acetic acid

1,2-Octadienoylglycine is classified as a member of the 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). 1,2-Octadienoylglycine is considered to be practically insoluble (in water) and acidic.

1,3-octadienoylglycine

2-[(1-oxoocta-1,3-dien-2-yl)amino]acetic acid

1,3-Octadienoylglycine is classified as a member of the 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). 1,3-Octadienoylglycine is considered to be practically insoluble (in water) and acidic.

1,4-octadienoylglycine

2-[(1-oxoocta-1,4-dien-2-yl)amino]acetic acid

1,4-Octadienoylglycine is classified as a member of the 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). 1,4-Octadienoylglycine is considered to be slightly soluble (in water) and acidic.

1,5-octadienoylglycine

2-[(1-oxoocta-1,5-dien-2-yl)amino]acetic acid

1,5-Octadienoylglycine is classified as a member of the 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). 1,5-Octadienoylglycine is considered to be slightly soluble (in water) and acidic.

1,6-octadienoylglycine

2-[(1-oxoocta-1,6-dien-2-yl)amino]acetic acid

1,6-Octadienoylglycine is classified as a member of the 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). 1,6-Octadienoylglycine is considered to be slightly soluble (in water) and acidic.

1,7-octadienoylglycine

2-[(1-oxoocta-1,7-dien-2-yl)amino]acetic acid

1,7-Octadienoylglycine is classified as a member of the 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). 1,7-Octadienoylglycine is considered to be slightly soluble (in water) and acidic.

2-octenoylglycine

2-amino-3-oxodec-4-enoic acid

C10H17NO3 (199.1208)

2-Octenoylglycine is classified as a member of the 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). 2-Octenoylglycine is considered to be slightly soluble (in water) and acidic.

2-nonenoylglycine

2-amino-3-oxoundec-4-enoic acid

C11H19NO3 (213.1365)

2-Nonenoylglycine is classified as a member of the 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). 2-Nonenoylglycine is considered to be practically insoluble (in water) and acidic.

N(5)-Acetylornithine

2-amino-5-acetamidopentanoic acid

C7H14N2O3 (174.1004)

2-Aminoheptanoic acid

alpha-Aminoenanthic acid

C7H15NO2 (145.1103)

DL-Methionine sulfone

Methionine sulfone, 35S-labeled, (+-)-isomer

C5H11NO4S (181.0409)

(+)-2-Amino-7-phosphonoheptanoic acid

2-Amino-7-phosphonoheptanoic acid, (+-)-isomer

C7H16NO5P (225.0766)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists D002491 - Central Nervous System Agents > D000927 - Anticonvulsants

(1r,3r)-1-Aminocyclopentane-1,3-dicarboxylic acid

1-Amino-1,3-dicarboxycyclopentane, trans-(1R,3S)-isomer

C7H11NO4 (173.0688)

D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents D020011 - Protective Agents trans-ACPD, a metabotropic receptor agonist, produces calcium mobilization and an inward current in cultured cerebellar Purkinje neurons.

(1R,4R,5S,6R)-4-Amino-2-oxabicyclo[3.1.0]hexane-4,6-dicarboxylic acid

C7H9NO5 (187.0481)

(2R,6S)-2,6-Diaminoheptanedioic acid

C7H14N2O4 (190.0954)

Meso-diaminopimelate, also known as diaminopimelic acid or dpm, 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). Meso-diaminopimelate is soluble (in water) and a moderately acidic compound (based on its pKa). Meso-diaminopimelate can be found in a number of food items such as italian sweet red pepper, sweet basil, horseradish, and hickory nut, which makes meso-diaminopimelate a potential biomarker for the consumption of these food products. Meso-diaminopimelate is a characteristic of certain cell walls of some bacteria. Meso-diaminopimelate is often found in the peptide linkages of NAM-NAG chains that make up the cell wall of gram-negative bacteria. When provided, they exhibit normal growth. When in deficiency, they still grow but with the inability to make new cell wall proteoglycan . 2,6-Diaminoheptanedioic acid is an endogenous metabolite.

(2R)-2-Amino-4-(amino-butyl-oxo-lambda6-sulfanylidene)butanoic acid

(2R)-2-Amino-4-(amino-butyl-oxo-lambda6-sulphanylidene)butanoic acid

C8H18N2O3S (222.1038)

(2S)-1,2-Dimethylpyrrolidine-2-carboxylic acid

C7H13NO2 (143.0946)

(2S)-2-Amino-3-[(2-chloroacetyl)amino]propanoic acid

C5H9ClN2O3 (180.0302)

2-Amino-4-(phosphonomethyl)hept-3-enoic acid

2-Amino-4-propyl-5-phosphono-3-pentenoic acid

C8H16NO5P (237.0766)

3,5-Dihydroxyphenylglycine

2-amino-2-(3,5-dihydroxyphenyl)acetic acid

C8H9NO4 (183.0532)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists DHPG ((RS)-3,5-DHPG) is an amino acid, which acts as a selective and potent agonist of group I mGluR (mGluR 1 and mGluR 5), shows no effect on Group II or Group III mGluRs[1]. DHPG ((RS)-3,5-DHPG) is also an effective antagonist of mGluRs linked to phospholipase D[2].

alpha-Methyl-4-carboxyphenylglycine

4-(1-amino-1-carboxyethyl)benzoic acid

C10H11NO4 (209.0688)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists (RS)-MCPG (alpha-MCPG) is a competitive and selective group I/group II metabotropic glutamate receptor (mGluR) antagonist. (RS)-MCPG blocks theta-burst stimulation (TBS)-induced shifts in both juvenile and neonatal rat hippocampal neurons[1][2].

3-Chloro-D-alanine

3-Chloroalanine hydrochloride, (DL-ala)-isomer

C3H6ClNO2 (123.0087)

4-(3-Phosphonopropyl)piperazine-2-carboxylic acid

3-(2-Carboxypiperazin-4-yl)propyl-1-phosphonic acid

C8H17N2O5P (252.0875)

N-(2-Hydroxyethyl)ethylenediaminetriacetic acid

2-({2-[bis(carboxymethyl)amino]ethyl}(2-hydroxyethyl)amino)acetic acid

C10H18N2O7 (278.1114)

D064449 - Sequestering Agents > D002614 - Chelating Agents

beta-N-Methylamino-L-alanine

alpha-amino-beta-Methylaminopropionate

C4H10N2O2 (118.0742)

2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

(+)-(1S,2S,5R,6S)-2-Aminobicyclo(3.1.0)hexane-2,6-dicarboxylic acid

C8H11NO4 (185.0688)

D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants (rel)-Eglumegad ((rel)-LY354740) is a relative configuration of Eglumegad (HY-18941). Eglumegad is a highly potent and selective group II (mGlu2/3) receptor agonist with EC50s of 5 and 24 nM for transfected human mGlu2 and mGlu3 receptors, respectively[1].

2,3-Dihydro-1H-pyrrole-2-carboxylic acid

2-((3,5-Dihydroxyphenyl)amino)acetic acid

2-[(3,5-dihydroxyphenyl)amino]acetic acid

C8H9NO4 (183.0532)

4-Hydroxyphenylglycine

4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (+-)-isomer

C8H9NO3 (167.0582)

D004791 - Enzyme Inhibitors

2-Amino-3-cyclohexylpropanoic acid

2-amino-3-cyclohexylpropanoic acid

C9H17NO2 (171.1259)

2-Amino-3-fluoropropanoic acid

3-Fluoroalanine, (DL-ala)-isomer

C3H6FNO2 (107.0383)

3-Hydroxynorvaline

3-Hydroxynorvaline, threo-(DL)-isomer

C5H11NO3 (133.0739)

2-Amino-4-oxopentanoic acid

C5H9NO3 (131.0582)

2-Amino-4-phosphonobutyric acid

L-2-Amino-4-phosphonobutanoic acid

C4H10NO5P (183.0297)

2-amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid

2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid

C8H18N4O2 (202.143)

(E)-2-Amino-5-phosphonopent-3-enoic acid

2-Amino-5-phosphono-3-pentenoic acid, e-(+-)-isomer

C5H10NO5P (195.0297)

alpha-Aminobutyric acid

alpha-Aminobutyric acid, (+-)-isomer

Dl-aminobutyric acid, also known as butyrine or homoalanine, 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). Dl-aminobutyric acid is soluble (in water) and a moderately acidic compound (based on its pKa). Dl-aminobutyric acid can be found in peanut, which makes dl-aminobutyric acid a potential biomarker for the consumption of this food product.

2-Chloro-L-alanine

2-amino-2-chloropropanoic acid

C3H6ClNO2 (123.0087)

5-Fluoromethylornithine

2,5-diamino-6-fluorohexanoic acid

C6H13FN2O2 (164.0961)

2,5-Dihydro-1H-pyrrole-2-carboxylic acid

3,4-Dehydroproline, L-(+) tartrate salt, (S)-isomer

5-hydroxylysine

(2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid

C6H14N2O3 (162.1004)

[(3-Methylbutyl)amino]acetic acid

2-[(3-methylbutyl)amino]acetic acid

C7H15NO2 (145.1103)

2,7-Diamino-7-iminoheptanoic acid

2-amino-6-carbamimidoylhexanoic acid

C7H15N3O2 (173.1164)

3-Anilinoalanine

2-amino-3-(phenylamino)propanoic acid

C9H12N2O2 (180.0899)

3-Cyanoalanine

2-Amino-3-cyanopropanoic acid

C4H6N2O2 (114.0429)

Beta-cyanoalanine, also known as propargylglycine, 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). Beta-cyanoalanine is soluble (in water) and an extremely strong acidic compound (based on its pKa). Beta-cyanoalanine can be found in broad bean, which makes beta-cyanoalanine a potential biomarker for the consumption of this food product.

3-Formyl Rifamycin

26-formyl-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate

C38H47NO13 (725.3047)

2-Amino-4-methyl-5-phosphonopent-3-enoic acid

2-Amino-4-methyl-5-phosphono-3-pentenoic acid, e(+-)-isomer

C6H12NO5P (209.0453)

3,3,5'-Triiodothyronine

2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-5,5-diiodocyclohexa-1,3-dien-1-yl]propanoic acid

C15H14I3NO4 (652.8057)

3,5,3-Triiodothyronine

2-amino-3-[4-(4-hydroxyphenoxy)-3,5,5-triiodocyclohexa-1,3-dien-1-yl]propanoic acid

C15H14I3NO4 (652.8057)

5-[(1-Iminoethyl)amino]-2-aminopentanoic acid

C7H15N3O2 (173.1164)

4-(Phosphonomethyl)piperidine-2-carboxylic acid

4-(Phosphonomethyl)-2-piperidinecarboxylic acid

C7H14NO5P (223.061)

5-Aminosalicyl-glycine

2-{[(5-amino-2-hydroxyphenyl)methyl]amino}acetic acid

C9H12N2O3 (196.0848)

D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates

5-(delta-Carboxybutyl)homocysteine

2-amino-4-[(3-carboxypropyl)sulfanyl]butanoic acid

C8H15NO4S (221.0722)

5-Diazo-4-oxo-L-norvaline

2-amino-5-diazo-4-oxopentanoic acid

C5H7N3O3 (157.0487)

5-Hydroxy-4-oxo-L-norvaline

2-Amino-5-hydroxy-4-oxopentanoic acid

C5H9NO4 (147.0532)

D000890 - Anti-Infective Agents > D000935 - Antifungal Agents

5-Hydroxylysinonorleucine

6-amino-2-[(5-amino-5-carboxypentan-2-yl)amino]-5-hydroxyhexanoic acid

C12H25N3O5 (291.1794)

Dhlnl

2-amino-6-[(5-amino-5-carboxy-2-hydroxypentyl)amino]-5-hydroxyhexanoic acid

C12H25N3O6 (307.1743)

Ethylenediamine-N,N'-diacetic acid

2-({2-[(carboxymethyl)amino]ethyl}amino)acetic acid

C6H12N2O4 (176.0797)

2-(Prop-2-ynylamino)acetic acid

2-[(prop-2-yn-1-yl)amino]acetic acid

6-Diazo-5-oxo-L-norleucine

2-amino-6-diazo-5-oxohexanoic acid

C6H9N3O3 (171.0644)

6-Diazo-5-oxo-L-nor-Leucine (L-6-Diazo-5-oxonorleucine; DON) is a glutamine antagonist that irreversibly inhibits the catabolic effect of glutamine. 6-Diazo-5-oxo-L-nor-Leucine shows good anticancer activity (especially in pancreatic cancer) and reduces the self-renewal potential and metastatic capacity of tumour cells. 6-Diazo-5-oxo-L-nor-Leucine also possesses antibacterial and antiviral activity[1][2][3].

H-D-Arg(NO2)-OH

2-amino-5-{[amino(nitroamino)methylidene]amino}pentanoic acid

C6H13N5O4 (219.0967)

N-(Carboxymethyl)-N-(2-((carboxymethyl)amino)ethyl)glycine

C8H14N2O6 (234.0852)

2-(Difluoromethyl)arginine

2-amino-5-[(diaminomethylidene)amino]-2-(difluoromethyl)pentanoic acid

C7H14F2N4O2 (224.1085)

2-[4-(Carboxymethyl)-1,4,8,11-tetrazabicyclo[6.6.2]hexadecan-11-yl]acetic acid

2-[11-(carboxymethyl)-1,4,8,11-tetraazabicyclo[6.6.2]hexadecan-4-yl]acetic acid

C16H30N4O4 (342.2267)

alpha-Acetyllysine

2-acetyl-2,6-diaminohexanoic acid

C8H16N2O3 (188.1161)

Acivicin

L-(AlphaS,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid

C5H7ClN2O3 (178.0145)

(S)-2-Amino-3-(hydroxy(nitroso)amino)propanoic acid

C3H7N3O4 (149.0437)

α-Methyltryptophan

2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid

C12H14N2O2 (218.1055)

2,5-Diamino-2-methylpentanoic acid

alpha-Methylornithine monohydrochloride, (DL)-isomer, (14)C-labeled

C6H14N2O2 (146.1055)

D000970 - Antineoplastic Agents

Phosphomethylphosphonic acid adenylate ester

({[({[5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}methyl)phosphonic acid

C11H18N5O12P3 (505.0165)

Azaserine

2-amino-3-[(2-diazoacetyl)oxy]propanoic acid

C5H7N3O4 (173.0437)

Carboxybetaine

2-carboxy-2-(trimethylazaniumyl)acetate

C6H11NO4 (161.0688)

Carboxyethyllysine

6-amino-2-[(2-carboxyethyl)amino]hexanoic acid

C9H18N2O4 (218.1267)

Cbhcy

(R,S)-5-(3-Amino-3-carboxy-propylsulfanyl)-pentanoic acid

C9H17NO4S (235.0878)

N6-Ethanimidoyl-D-lysine

2-amino-6-[(1-aminoethylidene)amino]hexanoic acid

C8H17N3O2 (187.1321)

2-Chloro-5-hydroxyphenylglycine

2-amino-2-(2-chloro-5-hydroxyphenyl)acetic acid

C8H8ClNO3 (201.0193)

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

Clopidogrel carboxylic acid

2-(2-Chlorophenyl)-2-(6,7-dihydro-4H-thieno(3,2-c)pyridin-5-yl)acetic acid

C15H14ClNO2S (307.0434)

D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058914 - Purinergic Antagonists D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors

N(epsilon)-(Carboxymethyl)hydroxylysine

2-amino-6-[(carboxymethyl)amino]-5-hydroxyhexanoic acid

C8H16N2O5 (220.1059)

Cppene

3-(2-Carboxypiperazine-4-yl)-1-propenyl-1-phosphonic acid

C8H15N2O5P (250.0719)

Cysteine sulfinic acid

2-Amino-3-sulphinopropanoic acid

C3H7NO4S (153.0096)

D-Citrulline

2-amino-5-[(C-hydroxycarbonimidoyl)amino]pentanoic acid

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.

2-Amino-2-deoxy-D-gluconic acid

2-amino-3,4,5,6-tetrahydroxyhexanoic acid

C6H13NO6 (195.0743)

D-Homophenylalanine

(S)-2-Amino-4-phenylbutanoic acid

C10H13NO2 (179.0946)

D-Methionine (S)-S-oxide

alpha-amino-gamma-(Methylsulfinyl)-butyric acid

C5H11NO3S (165.046)

4-Oxo-5-phosphononorvaline

2-amino-4-oxo-5-phosphonopentanoic acid

C5H10NO6P (211.0246)

D-Threonine

alpha-Amino-beta-hydroxybutyric acid

C4H9NO3 (119.0582)

Alpha-amino-beta-hydroxybutyric acid, also known as α-amino-β-hydroxybutyrate, 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). Alpha-amino-beta-hydroxybutyric acid is soluble (in water) and a moderately acidic compound (based on its pKa). Alpha-amino-beta-hydroxybutyric acid can be found in peanut, which makes alpha-amino-beta-hydroxybutyric acid a potential biomarker for the consumption of this food product.

D,L-Buthionine

2-amino-4-(butylsulfanyl)butanoic acid

C8H17NO2S (191.098)

Dimethylarginine

5-[(diaminomethylidene)amino]-2-(dimethylamino)pentanoic acid

C8H18N4O2 (202.143)

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.

DL-2,5-Dihydrophenylalanine

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

C9H13NO2 (167.0946)

DL-Allylglycine

2-aminopent-4-enoic acid

C5H9NO2 (115.0633)

DL-Buthionine sulfoximine

2-amino-4-[(butan-2-yl)(imino)oxo-λ⁶-sulfanyl]butanoic acid

C8H18N2O3S (222.1038)

DL-Difluoromethylornithine

5-amino-2-[(difluoromethyl)amino]pentanoic acid

C6H12F2N2O2 (182.0867)

DL-Ethionine

2-Amino-4-(ethylsulphanyl)butanoic acid

C6H13NO2S (163.0667)

DL-Homocysteic acid

Homocysteic acid, monosodium salt, (+-)-isomer

C4H9NO5S (183.0201)

DL-Norleucine

Norleucine, L-isomer

C6H13NO2 (131.0946)

DL-Norvaline

alpha-DL-Aminopentanoic acid

C5H11NO2 (117.079)

Norvaline, also known as alpha-aminovaleric acid or A-aminovalerate, 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). Norvaline is soluble (in water) and a moderately acidic compound (based on its pKa). Norvaline can be synthesized from valeric acid. Norvaline can also be synthesized into 3-hydroxynorvaline and 2-amino-5-phosphonopentanoic acid. Norvaline can be found in blackcurrant and common buckwheat, which makes norvaline a potential biomarker for the consumption of these food products. Norvaline (abbreviated as Nva) is an amino acid with the formula CH3(CH2)2CH(NH2)CO2H. The compound is an isomer of the more common amino acid valine. Like most other α-amino acids, norvaline is chiral. It is a white, water-soluble solid . DL-Norvaline, a derivative of L-norvaline, L-norvaline is a non-competitive inhibitor of arginase. DL-Norvaline, a derivative of L-norvaline, L-norvaline is a non-competitive inhibitor of arginase.

DL-Propargylglycine

Propargylglycine hydrochloride