Classification Term: 2263
Carboxylic acids (ontology term: CHEMONTID:0001205)
Compounds containing a carboxylic acid group with the formula -C(=O)OH." []
found 38 associated metabolites at sub_class metabolite taxonomy ontology rank level.
Ancestor: Carboxylic acids and derivatives
Child Taxonomies: 1-carboxy-2-haloaromatic compounds, alpha-Mercaptocarboxylic acids
Cyclohexanecarboxylic acid
Cyclohexanecarboxylic acid is a flavouring ingredien Flavouring ingredient KEIO_ID C180 Cyclohexanecarboxylic acid is a Valproate structural analogue with anticonvulsant action[1].
Glyoxylic acid
Glyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. Glyoxylic acid is a liquid with a melting point of -93°C and a boiling point of 111°C. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates. The conjugate base of glyoxylic acid is known as glyoxylate (PMID: 16396466). In humans, glyoxylate is produced via two pathways: (1) through the oxidation of glycolate in peroxisomes and (2) through the catabolism of hydroxyproline in mitochondria. In the peroxisomes, glyoxylate is converted into glycine by glyoxylate aminotransferase (AGT1) or into oxalate by glycolate oxidase. In the mitochondria, glyoxylate is converted into glycine by mitochondrial glyoxylate aminotransferase AGT2 or into glycolate by glycolate reductase. A small amount of glyoxylate is converted into oxalate by cytoplasmic lactate dehydrogenase. Glyoxylic acid is found to be associated with primary hyperoxaluria I, which is an inborn error of metabolism. Under certain circumstances, glyoxylate can be a nephrotoxin and a metabotoxin. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. High levels of glyoxylate are involved in the development of hyperoxaluria, a key cause of nephrolithiasis (commonly known as kidney stones). Glyoxylate is both a substrate and inductor of sulfate anion transporter-1 (SAT-1), a gene responsible for oxalate transportation, allowing it to increase SAT-1 mRNA expression, and as a result oxalate efflux from the cell. The increased oxalate release allows the buildup of calcium oxalate in the urine, and thus the eventual formation of kidney stones. As an aldehyde, glyoxylate is also highly reactive and will modify proteins to form advanced glycation products (AGEs). Glyoxylic acid, also known as alpha-ketoacetic acid or glyoxylate, is a member of the class of compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Glyoxylic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Glyoxylic acid can be found in a number of food items such as european chestnut, cowpea, wheat, and common thyme, which makes glyoxylic acid a potential biomarker for the consumption of these food products. Glyoxylic acid can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout all human tissues. Glyoxylic acid exists in all living species, ranging from bacteria to humans. In humans, glyoxylic acid is involved in a couple of metabolic pathways, which include alanine metabolism and glycine and serine metabolism. Glyoxylic acid is also involved in several metabolic disorders, some of which include lactic acidemia, pyruvate carboxylase deficiency, 3-phosphoglycerate dehydrogenase deficiency, and hyperglycinemia, non-ketotic. Moreover, glyoxylic acid is found to be associated with transurethral resection of the prostate and primary hyperoxaluria I. Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially . KEIO_ID G013
Isobutyric acid
Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5\\%. (OMIM 207000). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath. Present in apple, morello cherry, guava fruit, wine grapes, pineapple, crispbread, other breads, cheeses, wines, scallop and several essential oils, e.g. Roman chamomile. Acid and simple esters used as flavouring agents KEIO_ID I012
Propionic acid
Propionic acid (PA) is an organic acid. It exists a clear liquid with a pungent and unpleasant smell somewhat resembling body odor. Propionic acid (PA) is widely used as an antifungal agent in food. It is present naturally at low levels in dairy products and occurs ubiquitously, together with other short-chain fatty acids (SCFA), in the gastro-intestinal tract of humans and other mammals as an end-product of the microbial digestion of carbohydrates. The metabolism of propionic acid begins with its conversion to propionyl coenzyme A, the usual first step in the metabolism of carboxylic acids. Since propionic acid has three carbons, propionyl-CoA cannot directly enter either beta oxidation or the citric acid cycles. In most vertebrates, propionyl-CoA is carboxylated to D-methylmalonyl-CoA, which is isomerised to L-methylmalonyl-CoA. Propionic acid has significant physiological activity in animals. Propionic acid is irritant but produces no acute systemic effects and has no demonstrable genotoxic potential (PMID 1628870). The human skin is host of several species of bacteria known as Propionibacteria, which are named after their ability to produce propionic acid. The most notable one is the Cutibacterium acnes (formerly known as Propionibacterium acnes), which lives mainly in the sebaceous glands of the skin and is one of the principal causes of acne. Propionic aciduria is one of the most frequent organic acidurias, a disease that comprise many various disorders. The outcome of patients born with Propionic aciduria is poor intellectual development patterns, with 60\\\% having an IQ less than 75 and requiring special education. Successful liver and/or renal transplantations, in a few patients, have resulted in better quality of life but have not necessarily prevented neurological and various visceral complications. These results emphasize the need for permanent metabolic follow-up whatever the therapeutic strategy (PMID 15868474). Decreased early mortality, less severe symptoms at diagnosis, and more favorable short-term neurodevelopmental outcome were recorded in patients identified through expanded newborn screening. (PMID 16763906)↵ When propionic acid is infused directly into rodents brains, it produces hyperactivity, dystonia, social impairment, perseveration and brain changes (e.g., innate neuroinflammation, glutathione depletion) that may be used as a means to model autism in rats. Propionic acid is a metabolite of Bacteroides, Clostridium, Dialister, Megasphaera, Phascolarctobacterium, Propionibacterium, Propionigenum, Salmonella, Selenomonas and Veillonella (https://www.mdpi.com/2311-5637/3/2/21). Propionic acid, also known as propionate or ethanecarboxylic acid, is a member of the class of compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Thus, propionic acid is considered to be a fatty acid lipid molecule. Propionic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Propionic acid can be found in a number of food items such as celery stalks, burbot, sapodilla, and dock, which makes propionic acid a potential biomarker for the consumption of these food products. Propionic acid can be found primarily in most biofluids, including feces, saliva, blood, and urine, as well as throughout most human tissues. Propionic acid exists in all living species, ranging from bacteria to humans. In humans, propionic acid is involved in a couple of metabolic pathways, which include propanoate metabolism and vitamin K metabolism. Propionic acid is also involved in few metabolic disorders, which include malonic aciduria, malonyl-coa decarboxylase deficiency, and methylmalonic aciduria due to cobalamin-related disorders. Moreover, propionic acid is found to be associated with propionic acidemia. Propionic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound.
Acetic acid
Acetic acid is a two-carbon, straight-chain fatty acid. It is the smallest short-chain fatty acid (SCFA) and one of the simplest carboxylic acids. is an acidic, colourless liquid and is the main component in vinegar. Acetic acid has a sour taste and pungent smell. It is an important chemical reagent and industrial chemical that is used in the production of plastic soft drink bottles, photographic film; and polyvinyl acetate for wood glue, as well as many synthetic fibres and fabrics. In households diluted acetic acid is often used as a cleaning agent. In the food industry acetic acid is used as an acidity regulator. Acetic acid is found in all organisms, from bacteria to plants to humans. The acetyl group, derived from acetic acid, is fundamental to the biochemistry of virtually all forms of life. When bound to coenzyme A (to form acetylCoA) it is central to the metabolism of carbohydrates and fats. However, the concentration of free acetic acid in cells is kept at a low level to avoid disrupting the control of the pH of the cell contents. Acetic acid is produced and excreted in large amounts by certain acetic acid bacteria, notably the Acetobacter genus and Clostridium acetobutylicum. These bacteria are found universally in foodstuffs, water, and soil. Due to their widespread presence on fruit, acetic acid is produced naturally as fruits and many other sugar-rich foods spoil. Several species of anaerobic bacteria, including members of the genus Clostridium and Acetobacterium can convert sugars to acetic acid directly. However, Clostridium bacteria are less acid-tolerant than Acetobacter. Even the most acid-tolerant Clostridium strains can produce acetic acid in concentrations of only a few per cent, compared to Acetobacter strains that can produce acetic acid in concentrations up to 20\\%. Acetic acid is also a component of the vaginal lubrication of humans and other primates, where it appears to serve as a mild antibacterial agent. Acetic acid can be found in other biofluids such as urine at low concentrations. Urinary acetic acid is produced by bacteria such as Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465). Acetic acid concentrations greater than 30 uM/mM creatinine in the urine can indicate a urinary tract infection, which typically suggests the presence of E. coli or Klebshiella pneumonia in the urinary tract. (PMID: 24909875) Acetic acid is also produced by other bacteria such as Akkermansia, Bacteroidetes, Bifidobacterium, Prevotella and Ruminococcus (PMID: 20444704; PMID: 22292465). G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids > G01AD - Organic acids S - Sensory organs > S02 - Otologicals > S02A - Antiinfectives > S02AA - Antiinfectives D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents It is used for smoking meats and fish C254 - Anti-Infective Agent KEIO_ID A029
N-Acetyl-beta-alanine
N-Acetyl-beta-alanine belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. N-Acetyl-beta-alanine has been identified in the human placenta (PMID: 32033212). KEIO_ID A138 Ac-β-Ala-OH (N-Acetyl-β-alanine), an abnormal amino acid metabolite, is a mono-N-protected amino acid (MPAA) ligand[1].
Propynoic acid
Propynoic acid, also known as propiolic acid, is involved in propanoate metabolism and is interconverted into 2-propyn-1-al by mitochondrial aldehyde dehydrogenase. Propynoic acid is an unsaturated organic acid and it can be prepared by boiling acetylene dicarboxylic acid. It is chemically obtained by the action of alcoholic potash on dibromosuccinic acid, or its acid potassium salt with water. It forms silky crystals which melt at 6°C and boil at about 144°C with decomposition. It is soluble in water and possesses an odour resembling that of acetic acid. Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid). It undergoes bromination to give dibromoacrylic acid. With hydrogen chloride it forms chloroacrylic acid. Its ethyl ester condenses with hydrazine to form pyrazolone. Propynoic acid forms a characteristic explosive silver salt upon the addition of ammoniacal silver nitrate to its aqueous solution, and an amorphous precipitate which explodes upon warming with ammoniacal cuprous chloride. Its ethyl ester condenses with hydrazine to form pyrazolone (Wikipedia). Propynoic acid is involved in propanoate metabolism and is interconverted between 2-propyn1-al and propynoic acid by mitochondrial aldehyde dehydrogenase. Propiolic acid is an unsaturated organic acid and it can be prepared by boiling acetylene dicarboxylic acid. It is chemically obtained by the action of alcoholic potash on dibromosuccinic acid, or its acid potassium salt with water. It forms silky crystals which melt at 6 degree centigrade, and boil at about 144 degree centigrade with decomposition. It is soluble in water and possesses an odor resembling that of acetic acid. Exposure to sunlight converts it into trimesic acid (benzene-1,3,5-tricarboxylic acid). Bromine converts it into dibromoacrylic acid, and it gives with hydrochloric acid O-chloracrylic acid. It forms a characteristic explosive silver salt on the addition of ammoniacal silver nitrate to its aqueous solution, and an amorphous precipitate which explodes on warming with ammoniacal cuprous chloride. Its ethyl ester condenses with hydrazine to form pyrazolone. [HMDB] KEIO_ID P040
Formic acid
Formic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer. Urinary formate is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465). It is used as a flavouring adjunct, an animal feed additive, a brewing antiseptic and as a food preservative
Dihydroasparagusic acid
Dihydroasparagusic acid is found in asparagus. Dihydroasparagusic acid is isolated from asparagus Asparagus officinali Isolated from asparagus Asparagus officinalis. Dihydroasparagusic acid is found in asparagus and green vegetables.
Butoxyacetic acid
Butoxyacetic acid belongs to the family of Carboxylic Acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
N-Acetylanonaine
N-Acetylanonaine is found in fruits. N-Acetylanonaine is an alkaloid from the root bark of Zanthoxylum simulans (Szechuan pepper
Ethoxyacetic acid
Ethoxyacetic acid is found in herbs and spices. Ethoxyacetic acid is a component of perilla leaf extract (Perilla frutescens Component of perilla leaf extract (Perilla frutescens). Ethoxyacetic acid is found in herbs and spices. Ethoxyacetic acid is an endogenous metabolite.
Cyclohexaneacetic acid
Cyclohexaneacetic acid is a flavouring ingredien Flavouring ingredient Cyclohexaneacetic acid is an endogenous metabolite.
trans-2-Hexyl-1-cyclopropaneacetic acid
trans-2-Hexyl-1-cyclopropaneacetic acid is a component of cascarilla essential oi
3-Iodopropanoic acid
3-Iodopropanoic acid is used as a feed additive for ruminant
3-Mercaptopropanoic acid
D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants > D003292 - Convulsants D018377 - Neurotransmitter Agents > D018682 - GABA Agents 3-Mercaptopropanoic acid is a flavouring agent [CCD]. D004791 - Enzyme Inhibitors Flavouring agent [CCD]
Methoxyacetic acid
Methoxyacetic acid belongs to the family of Carboxylic Acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH. D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents Methoxyacetic acid is an endogenous metabolite.
Pivalic acid
Pivalic acid is a carboxylic acid with a molecular formula of (CH3)3CCO2H. This colourless, odiferous organic compound is solid at room temperature. Relative to esters of most carboxylic acids, esters of pivalic acid are unusually resistant to hydrolysis. Some applications result from this thermal stability. Polymers derived from pivalate esters of vinyl alcohol are highly reflective lacquers. The pivaloyl (abbreviated piv or pv) group is a protective group for alcohols in organic synthesis.
(2-Methoxyethoxy)propanoic acid
(2-Methoxyethoxy)propanoic acid is a monocarboxylic acid that is propanoic acid substituted at C-2 by a 2-methoxyethoxy group.
2-(1-Ethoxyethoxy)propanoic acid
2-(1-Ethoxyethoxy)propanoic acid belongs to the family of Carboxylic Acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
2-hydroxyacrylic Acid
2-hydroxyacrylic Acid, also known as 2-Hydroxyacrylate, is classified as a member of the Carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. 2-hydroxyacrylic Acid is considered to be soluble (in water) and acidic
Aminooxyacetic acid
D018377 - Neurotransmitter Agents > D018682 - GABA Agents D004791 - Enzyme Inhibitors
Loxanast
C308 - Immunotherapeutic Agent > C574 - Immunosuppressant
METHACRYLIC ACID
Methacrylic acid, also known as A-methacrylate or 2-methyl-2-propenoic acid, is a member of the class of compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Methacrylic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Methacrylic acid can be synthesized from acrylic acid. Methacrylic acid is also a parent compound for other transformation products, including but not limited to, bisphenol A dimethacrylate, trichagmalin B, and methyl methacrylate. Methacrylic acid can be found in roman camomile, which makes methacrylic acid a potential biomarker for the consumption of this food product. Methacrylic acid, abbreviated MAA, is an organic compound. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA) and poly(methyl methacrylate) (PMMA). The methacrylates have numerous uses, most notably in the manufacture of polymers with trade names such as Lucite and Plexiglas. MAA occurs naturally in small amounts in the oil of Roman chamomile .
Calcium acetate
It is used in foods as a firming agent, acidity regulator, sequestrant, stabiliser and thickener, and nutrient supplement (Ca source). It is used as an acidifier/preservative in bread, and in some gelling mixtures. Calcium acetate is a food additive, mainly in candy products.; Calclacite is a name for calcium acetate chloride pentahydrate, which is treated as mineral species but possess anthropogenic origin.; Patients with advanced renal insufficiency (creatinine clearance less than 30 ml/min) exhibit phosphate retention and some degree of hyperphosphatemia. The retention of phosphate plays a pivotal role in causing secondary hyperparathyroidism associated with osteodystrophy, and soft-tissue calcification. The mechanism by which phosphate retention leads to hyperparathyroidism is not clearly delineated. Therapeutic efforts directed toward the control of hyperphosphatemia include reduction in the dietary intake of phosphate, inhibition of absorption of phosphate in the intestine with phosphate binders, and removal of phosphate from the body by more efficient methods of dialysis. The rate of removal of phosphate by dietary manipulation or by dialysis is insufficient. Dialysis patients absorb 40\\% to 80\\% of dietary phosphorus. Therefore, the fraction of dietary phosphate absorbed from the diet needs to be reduced by using phosphate binders in most renal failure patients on maintenance dialysis. Calcium acetate when taken with meals combines with dietary phosphate to form insoluble calcium phosphate which is excreted in the feces. Maintenance of serum phosphorus below 6.0 mg/dl is generally considered as a clinically acceptable outcome of treatment with phosphate binders. Calcium acetate is highly soluble at neutral pH, making the calcium readily available for binding to phosphate in the proximal small intestine. It is used in foods as a firming agent, acidity regulator, sequestrant, stabiliser and thickener, and nutrient supplement (Ca source). It is used as an acidifier/preservative in bread, and in some gelling mixtures V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AE - Drugs for treatment of hyperkalemia and hyperphosphatemia D064449 - Sequestering Agents > D002614 - Chelating Agents
formate
Formate, also known as formic acid or methanoic acid, is a member of the class of compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Formate is soluble (in water) and a weakly acidic compound (based on its pKa). Formate can be found in a number of food items such as mammee apple, chicory roots, malabar spinach, and grapefruit, which makes formate a potential biomarker for the consumption of these food products. Formate (IUPAC name: methanoate) is the anion derived from formic acid. Its formula is represented in various equivalent ways: CHOO‚àí or HCOO‚àí or HCO2‚àí. It is the product of deprotonation of formic acid. It is the simplest carboxylate anion. A formate (compound) is a salt or ester of formic acid . Formate, also known as formic acid or methanoic acid, is a member of the class of compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Formate is soluble (in water) and a weakly acidic compound (based on its pKa). Formate can be found in a number of food items such as mammee apple, chicory roots, malabar spinach, and grapefruit, which makes formate a potential biomarker for the consumption of these food products. Formate (IUPAC name: methanoate) is the anion derived from formic acid. Its formula is represented in various equivalent ways: CHOO− or HCOO− or HCO2−. It is the product of deprotonation of formic acid. It is the simplest carboxylate anion. A formate (compound) is a salt or ester of formic acid .