Chemical Formula: C6H11NO4
Chemical Formula C6H11NO4
Found 120 metabolite its formula value is C6H11NO4
Aminoadipic acid
Aminoadipic acid (CAS: 542-32-5), also known as 2-aminoadipate, is a metabolite in the principal biochemical pathway of lysine. It is an intermediate in the metabolism (i.e. breakdown or degradation) of lysine and saccharopine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor N-methyl-D-aspartate (NMDA). Aminoadipic acid has also been shown to inhibit the production of kynurenic acid, a broad spectrum excitatory amino acid receptor antagonist, in brain tissue slices (PMID: 8566117). Recent studies have shown that aminoadipic acid is elevated in prostate biopsy tissues from prostate cancer patients (PMID: 23737455). Mutations in DHTKD1 (dehydrogenase E1 and transketolase domain-containing protein 1) have been shown to cause human 2-aminoadipic aciduria and 2-oxoadipic aciduria via impaired decarboxylation of 2-oxoadipate to glutaryl-CoA, which is the last step in the lysine degradation pathway (PMID: 23141293). Aging, diabetes, sepsis, and renal failure are known to catalyze the oxidation of lysyl residues to form 2-aminoadipic acid in human skin collagen and potentially other tissues (PMID: 18448817). Proteolytic breakdown of these tissues can lead to the release of free 2-aminoadipic acid. Studies in rats indicate that aminoadipic acid (along with the three branched-chain amino acids: leucine, valine, and isoleucine) levels are elevated in the pre-diabetic phase and so aminoadipic acid may serve as a predictive biomarker for the development of diabetes (PMID: 15389298). Long-term hyperglycemia of endothelial cells can also lead to elevated levels of aminoadipate which is thought to be a sign of lysine breakdown through oxidative stress and reactive oxygen species (ROS) (PMID: 21961526). 2-Aminoadipate is a potential small-molecule marker of oxidative stress (PMID: 21647514). Therefore, depending on the circumstances aminoadipic acid can act as an acidogen, a diabetogen, an atherogen, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A diabetogen is a compound that can lead to type 2 diabetes. An atherogen is a compound that leads to atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of aminoadipic acid are associated with at least two inborn errors of metabolism including 2-aminoadipic aciduria and 2-oxoadipic aciduria. Aminoadipic acid is an organic acid and abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. As a diabetogen, serum aminoadipic levels appear to regulate glucose homeostasis and have been highly predictive of individuals who later develop diabetes (PMID: 24091325). In particular, aminoadipic acid lowers fasting plasma glucose levels and enhances insulin secretion from human islets. As an atherogen, aminoadipic acid has been found to be produced at high levels via protein lysine oxidation in atherosclerotic plaques (PMID: 28069522). A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-methyl-D-aspartate; (NMDA). L-α-Aminoadipic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1118-90-7 (retrieved 2024-07-01) (CAS RN: 1118-90-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine. Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.
N-methyl-L-glutamic Acid
N-methyl-L-glutamic Acid, also known as N-Methylglutamate or (2S)-2-(methylamino)Pentanedioic acid, is classified as a glutamic acid or a Glutamic acid derivative. Glutamic acids are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-methyl-L-glutamic Acid is considered to be soluble (in water) and acidic KEIO_ID M067
O-acetylhomoserine
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)
(±)-2,2'-Iminobispropanoic acid
meso-2,2-Iminobispropanoic acid is found in mollusks. meso-2,2-Iminobispropanoic acid is from scallops (Patinopecten yessoensis) and squids (possibly Todarodes pacificus). From scallops (Patinopecten yessoensis) and squids (possibly Todarodes pacificus). meso-2,2-Iminobispropanoic acid is found in mollusks.
Alanyllactate
N-Acetylthreonine
N-Acetyl-L-threonine (or N-Acetylthreonine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylthreonine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylthreonine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-threonine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618). About 85\\% of all human proteins and 68\\% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylthreonine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free threonine can also occur. Excessive amounts N-acetyl amino acids including N-acetylthreonine (as well as N-acetylglycine, N-acetylserine, N-acetylmethionine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylglutamine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylthreonine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986; PMID: 20613759). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557). N-Acetylthreonine has been identified in the human placenta (PMID: 32033212).
Glutamic acid gamma-methyl ester
Glutamate gamma-methyl ester, also known as L-Glutamic acid 5-methyl ester or g-methyl-L-glutamate (CAS# 1499-55-4) is a white amorphous powder and soluble in water. Its melting point is 182 degree Celsius and should be stored at 2-8 degree Celsius Glutamic acid gamma-methyl ester has been identified in the human placenta (PMID: 32033212).
hydroxybutyrylglycine
Hydroxybutyrylglycine is classified as a member of the N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Hydroxybutyrylglycine is considered to be slightly soluble (in water) and acidic.ÂÂ
2-Aminoadipic acid
Aminoadipic acid, also known as a-aminoadipate or Aad, 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). Aminoadipic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Aminoadipic acid exists in all eukaryotes, ranging from yeast to humans. Within humans, aminoadipic acid participates in a number of enzymatic reactions. In particular, aminoadipic acid can be biosynthesized from allysine; which is mediated by the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, aminoadipic acid and oxoglutaric acid can be converted into oxoadipic acid and L-glutamic acid; which is catalyzed by the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In humans, aminoadipic acid is involved in the metabolic disorder called 2-aminoadipic 2-oxoadipic aciduria. Outside of the human body, Aminoadipic acid is found, on average, in the highest concentration within a few different foods, such as wheats, milk (cow), and ryes and in a lower concentration in dills, garden onions, and white cabbages. Aminoadipic acid has also been detected, but not quantified in, several different foods, such as barley, cow milks, cow milks, cow milks, and cow milks. This could make aminoadipic acid a potential biomarker for the consumption of these foods. Aminoadipic acid is a potentially toxic compound. Aminoadipic acid, with regard to humans, has been found to be associated with several diseases such as alpha-aminoadipic and alpha-ketoadipic aciduria, colorectal cancer, metastatic melanoma, and eosinophilic esophagitis; aminoadipic acid has also been linked to the inborn metabolic disorder 2-ketoadipic acidemia. A metabolite in the principal biochemical pathway of lysine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor, N-methyl-D-aspartate; (NMDA). D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine. Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.
α-Aminoadipic acid
An optically active form of 2-aminoadipic acid having D-configuration. The L-enantiomer of 2-aminoadipic acid. D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018691 - Excitatory Amino Acid Antagonists Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; ML_ID 9 Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine. Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.
alpha-Aminoadipate
Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine. Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.
Aminoadipate
Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine. Aminoadipic acid is an intermediate in the metabolism of lysine and saccharopine.
SYM 2081
SYM 2081 is a high-affinity ligand and potent, selective agonist of kainate receptors, inhibits [3H]-kainate binding with an IC50 of 35 nM, almost 3000- and 200-fold selectivity for kainate receptors over AMPA and NMDA receptors respectively[1].
(3~{r})-3-(2-Hydroxy-2-Oxoethylamino)butanoic Acid
N-methyl-L-glutamic acid
A N-methyl-L-alpha-amino acid with L-glutamic acid as the amino acid component.
2-Aminoadipic acid
An alpha-amino acid that is adipic acid bearing a single amino substituent at position 2. An intermediate in the formation of lysine.
O-Acetylhomoserine
An alpha-amino acid that is homoserine in which the alcoholic hydroxy group has been converted to the corresponding acetate.
2,2-Iminodipropanoic acid
An amino dicarboxylic acid that is 2,2-iminodiacetic acid substituted by methyl groups at positions 2 and 2.
O-acetyl-L-homoserine zwitterion
Zwitterionic form of O-acetyl-L-homoserine having an anionic carboxy group and a protonated alpha-amino group; major species at pH 7.3.
4-methyl-L-glutamic acid
An amino dicarboxylic acid that is L-glutamic acid substituted by a methyl group at position 4.
N-Methyl-DL-glutamic acid
N-Methyl-DL-glutamic acid is a L-Glutamic acid (HY-14608) analog with cytotoxic effects[1][2].
3,4-dihydroxypipecolic acid
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