Classification Term: 2538
Organosulfonic acids (ontology term: CHEMONTID:0001179)
Compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom)." []
found 39 associated metabolites at category metabolite taxonomy ontology rank level.
Ancestor: Organosulfonic acids and derivatives
Child Taxonomies: There is no child term of current ontology term.
Taurine
Essential nutrient obtained from diet and by in vivo synthysis from methionine and cysteine. Present in meats, fish, legumes, human milk, molluscs and other foods. Dietary supplement, e.g. in Red Bull drink. Taurine is a sulfur amino acid like methionine, cystine, cysteine and homocysteine. It is a lesser-known amino acid because it is not incorporated into the structural building blocks of protein. Yet taurine is an essential amino acid in pre-term and newborn infants of humans and many other species. Adults can synthesize their own taurine, yet are probably dependent in part on dietary taurine. Taurine is abundant in the brain, heart, breast, gallbladder and kidney and has important roles in health and disease in these organs. Taurine has many diverse biological functions serving as a neurotransmitter in the brain, a stabilizer of cell membranes and a facilitator in the transport of ions such as sodium, potassium, calcium and magnesium. Taurine is highly concentrated in animal and fish protein, which are good sources of dietary taurine. It can be synthesized by the body from cysteine when vitamin B6 is present. Deficiency of taurine occurs in premature infants and neonates fed formula milk, and in various disease states. Inborn errors of taurine metabolism have been described. OMIM 168605, an unusual neuropsychiatric disorder inherited in an autosomal dominant fashion through 3 generations of a family. Symptoms began late in the fifth decade in 6 affected persons and death occurred after 4 to 6 years. The earliest and most prominent symptom was mental depression not responsive to antidepressant drugs or electroconvulsive therapy. Sleep disturbances, exhaustion and marked weight loss were features. Parkinsonism developed later, and respiratory failure occurred terminally. OMIM 145350 describes congestive cardiomyopathy and markedly elevated urinary taurine levels (about 5 times normal). Other family members had late or holosystolic mitral valve prolapse and elevated urinary taurine values (about 2.5 times normal). In 2 with mitral valve prolapse, congestive cardiomyopathy eventually developed while the amounts of urinary taurine doubled. Taurine, after GABA, is the second most important inhibitory neurotransmitter in the brain. Its inhibitory effect is one source of taurines anticonvulsant and antianxiety properties. It also lowers glutamic acid in the brain, and preliminary clinical trials suggest taurine may be useful in some forms of epilepsy. Taurine in the brain is usually associated with zinc or manganese. The amino acids alanine and glutamic acid, as well as pantothenic acid, inhibit taurine metabolism while vitamins A and B6, zinc and manganese help build taurine. Cysteine and B6 are the nutrients most directly involved in taurine synthesis. Taurine levels have been found to decrease significantly in many depressed patients. One reason that the findings are not entirely clear is because taurine is often elevated in the blood of epileptics who need it. It is often difficult to distinguish compensatory changes in human biochemistry from true metabolic or deficiency disease. Low levels of taurine are found in retinitis pigmentosa. Taurine deficiency in experimental animals produces degeneration of light-sensitive cells. Therapeutic applications of taurine to eye disease are likely to be forthcoming. Taurine has many important metabolic roles. Supplements can stimulate prolactin and insulin release. The parathyroid gland makes a peptide hormone called glutataurine (glutamic acid-taurine), which further demonstrates taurines role in endocrinology. Taurine increases bilirubin and cholesterol excretion in bile, critical to normal gallbladder function. It seems to inhibit the effect of morphine and potentiates the effects of opiate antagonists. Low plasma taurine levels have been found in a variety of conditions, i.e., depression, hypertension, hypothyroidism, gout, institutionalized patients, infertility, obesity, kidney fa... Taurine is a sulfur amino acid like methionine, cystine, cysteine, and homocysteine. It is a lesser-known amino acid because it is not incorporated into the structural building blocks of protein. Yet taurine is an essential amino acid in pre-term and newborn infants of humans and many other species. Adults can synthesize their own taurine, yet are probably dependent, in part, on dietary taurine. Taurine is abundant in the brain, heart, breast, gallbladder, and kidney and has important roles in health and disease in these organs. Taurine has many diverse biological functions including serving as a neurotransmitter in the brain, a stabilizer of cell membranes, and a facilitator in the transport of ions such as sodium, potassium, calcium, and magnesium. Taurine is highly concentrated in animal and fish protein, which are good sources of dietary taurine. It can be synthesized by the body from cysteine when vitamin B6 is present. Deficiency of taurine occurs in premature infants, neonates fed formula milk, and various disease states. Several inborn errors of taurine metabolism have been described. Perry syndrome is an unusual neuropsychiatric disorder inherited in an autosomal dominant fashion through three generations of a family. Symptoms began late in the fifth decade in 6 affected persons and death occurred after 4 to 6 years. The earliest and most prominent symptom was mental depression that was not responsive to antidepressant drugs or electroconvulsive therapy. Sleep disturbances, exhaustion, and marked weight loss were features. Parkinsonism developed later, and respiratory failure occurred terminally (OMIM: 168605). Hypertaurinuric cardiomyopathy describes congestive cardiomyopathy and markedly elevated urinary taurine levels (about 5 times normal). Other family members had late or holosystolic mitral valve prolapse and elevated urinary taurine values (about 2.5 times normal). In two with mitral valve prolapse, congestive cardiomyopathy eventually developed while the amounts of urinary taurine doubled (OMIM: 145350). Taurine, after GABA, is the second most important inhibitory neurotransmitter in the brain. Its inhibitory effect is one source of taurines anticonvulsant and antianxiety properties. It also lowers glutamic acid in the brain, and preliminary clinical trials suggest taurine may be useful in some forms of epilepsy. Taurine in the brain is usually associated with zinc or manganese. The amino acids alanine and glutamic acid, as well as pantothenic acid, inhibit taurine metabolism while vitamins A and B6, zinc, and manganese help build taurine. Cysteine and B6 are the nutrients most directly involved in taurine synthesis. Taurine levels have been found to decrease significantly in many depressed patients. One reason that the findings are not entirely clear is that taurine is often elevated in the blood of epileptics who need it. It is often difficult to distinguish compensatory changes in human biochemistry from true metabolic or deficiency disease. Low levels of taurine are found in retinitis pigmentosa. Taurine deficiency in experimental animals produces degeneration of light-sensitive cells. Therapeutic applications of taurine to eye disease are likely to be forthcoming. Taurine has many important metabolic roles. Supplements can stimulate prolactin and insulin release. The parathyroid gland makes a peptide hormone called glutataurine (glutamic acid-taurine), which further demonstrates taurines role in endocrinology. Taurine increases bilirubin and cholesterol excretion in bile, critical to normal gallbladder function. It seems to inhibit the effect of morphine and potentiates the effects of opiate antagonists. Low plasma taurine levels have been found in a variety of conditions, i.e. depression, hypertension, hypothyroidism, gout, institutionalized patients, infertility, obesity, kidney failure, and others (http://www.dcnutrition.com/AminoAcids/). Moreover, taurine is found to be associated with maple syrup uri... Large white crystals or white powder. Taurine is an amino sulfonic acid that is the 2-amino derivative of ethanesulfonic acid. It is a naturally occurring amino acid derived from methionine and cysteine metabolism. An abundant component of fish- and meat-based foods, it has been used as an oral supplement in the treatment of disorders such as cystic fibrosis and hypertension. It has a role as a human metabolite, an antioxidant, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a glycine receptor agonist, a nutrient and a radical scavenger. It is a conjugate acid of a 2-aminoethanesulfonate. It is a tautomer of a taurine zwitterion. Taurine, whose chemical name is 2-aminoethanesulfonic acid, is one of the most abundant amino acids in several organs. It plays important role in essential biological processes. This conditional amino acid can be either be manufactured by the body or obtained in the diet mainly by the consumption of fish and meat. The supplements containing taurine were FDA approved by 1984 and they are hypertonic injections composed by cristalline amino acids. Taurine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). A conditionally essential nutrient, important during mammalian development. It is present in milk but is isolated mostly from ox bile and strongly conjugates bile acids. See also: ... View More ... An amino sulfonic acid that is the 2-amino derivative of ethanesulfonic acid. It is a naturally occurring amino acid derived from methionine and cysteine metabolism. An abundant component of fish- and meat-based foods, it has been used as an oral supplement in the treatment of disorders such as cystic fibrosis and hypertension. [Spectral] Taurine (exact mass = 125.01466) and L-Threonine (exact mass = 119.05824) and 4-Hydroxy-L-proline (exact mass = 131.05824) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Taurine (exact mass = 125.01466) and L-Glutamate (exact mass = 147.05316) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Taurine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-35-7 (retrieved 2024-06-29) (CAS RN: 107-35-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Taurine, a sulphur-containing amino acid and an organic osmolyte involved in cell volume regulation, provides a substrate for the formation of bile salts, and plays a role in the modulation of intracellular free calcium concentration. Taurine has the ability to activate autophagy in adipocytes[1][2][3]. Taurine, a sulphur-containing amino acid and an organic osmolyte involved in cell volume regulation, provides a substrate for the formation of bile salts, and plays a role in the modulation of intracellular free calcium concentration. Taurine has the ability to activate autophagy in adipocytes[1][2][3].
Tramiprosate
3-aminopropanesulfonic acid is an amino sulfonic acid that is the 3-amino derivative of propanesulfonic acid. It has a role as an algal metabolite, a nootropic agent, an anticonvulsant, a GABA agonist and an anti-inflammatory agent. It is a tautomer of a 3-aminopropanesulfonic acid zwitterion. D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018755 - GABA Agonists D002491 - Central Nervous System Agents > D000927 - Anticonvulsants C26170 - Protective Agent > C1509 - Neuroprotective Agent Tramiprosate (Homotaurine), an orally active and brain-penetrant natural amino acid found in various species of red marine algae. Tramiprosate binds to soluble Aβ and maintains Aβ in a non-fibrillar form. Tramiprosate is also a GABA analog and possess neuroprotection, anticonvulsion and antihypertension effects[1][2][3].
2-Hydroxyethanesulfonate
2-Hydroxyethanesulfonate (also known as 2-Hydroxyethanesulfonic acid or isethionic acid) is an organosulfur compound containing a short chain alkane sulfonate linked to a hydroxyl group. It is a water-soluble liquid used in the manufacture of mild, biodegradable, and high-foaming anionic surfactants. These surfactants provide gentle cleansing and a soft skin feel. 2-Hydroxyethanesulfonate forms a colourless, syrupy, and strongly acidic liquid that can form detergents with oleic acid. 2-Hydroxyethanesulfonate is frequently used in the industrial production of taurine. Mammals are also able to endogenously synthesize 2-hydroxyethanesulfonate via taurine through a possible enzymatic deamination process (PMID: 14490797). 2-Hydroxyethanesulfonate can be found in both human plasma and urine (PMID: 1159536, PMID: 6066118). Higher plasma levels of 2-hydroxyethanesulfonate have been shown to be protective against type 2 diabetes. Isethionic acid is an alkanesulfonic acid in which the sulfo group is directly linked to a 2-hydroxyethyl group. It has a role as a human metabolite. It is a conjugate acid of an isethionate. Isethionic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 2-Hydroxyethanesulfonic acid is a natural product found in Gayliella flaccida, Tichocarpus crinitus, and Trypanosoma brucei with data available. A colorless, syrupy, strongly acidic liquid that can form detergents with oleic acid. Isethionic acid C2H6O4S is a short chain alkane sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel. An alkanesulfonic acid in which the sulfo group is directly linked to a 2-hydroxyethyl group. KEIO_ID I041
Taurocyamine
Taurocyamine is a guanidino-taurine analogue derived from taurine. It is an intermediate of taurine and hypotaurine metabolism. The concentration of taurocyamine present in the human urine and serum could be as low as 8-78 pmol/ml. (PMID: 6520173) Plasma levels of taurocyamine are significantly increased in patients with chronic renal failure with or without hemodialysis. (PMID: 10516995). Taurocyamine is an endogenous alkaline "shifter". It effectively reduces the extent of brain intracellular lactic acidosis brought about by anoxic insult. A pH alkaline shift may protect the brain against the deleterious effects of lactic acidosis. (PMID: 8241459). Taurocyamine is an inhibitor of taurine transport and a glycine receptor antagonist in the brain (PMID: 12411417). [HMDB] Taurocyamine is a guanidino-taurine analogue derived from taurine. It is an intermediate of taurine and hypotaurine metabolism. The concentration of taurocyamine present in the human urine and serum could be as low as 8-78 pmol/ml. (PMID: 6520173) Plasma levels of taurocyamine are significantly increased in patients with chronic renal failure with or without hemodialysis. (PMID: 10516995). Taurocyamine is an endogenous alkaline "shifter". It effectively reduces the extent of brain intracellular lactic acidosis brought about by anoxic insult. A pH alkaline shift may protect the brain against the deleterious effects of lactic acidosis. (PMID: 8241459). Taurocyamine is an inhibitor of taurine transport and a glycine receptor antagonist in the brain (PMID: 12411417).
Mesylate
Mesylate, also known as methanesulfonate or mesylic acid, belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom). Mesylate exists as a solid, soluble (in water), and an extremely strong acidic compound (based on its pKa). Mesylate is also a parent compound for other transformation products, including but not limited to, methanesulfonates, S-methyl methanethiosulfonate, and (Z)-11-methyl-N-(methylsulfonyl)dodec-2-enamide. KEIO_ID M135 KEIO_ID M021
Mesna
Mesna is a chemoprotectant. Chemoprotectants have been developed as a means of ameliorating the toxicity associated with cytotoxic agents by providing site-specific protection for normal tissues, without compromising antitumour efficacy. Mesna eliminates the risk of therapy-limiting urotoxic side effects of oxazaphosphorines. Mesna is widely used for the prevention of cyclophosphamide-related hemorrhagic cystitis. It has been associated with hypersensitivity-like cutaneous and systemic reactions in adult patients. Mesna offers significant uroprotection in patients receiving high dose cyclophosphamide, and is widely used in paediatric oncology practice It is, therefore, important to recognize that it may be associated with a rare but significant systemic adverse reaction. A hypersensitivity-like reaction to mesna was first reported in a young adult receiving treatment for Hodgkin disease over 20 years ago. Oral administration of mesna can facilitate outpatient ifosfamide therapy. Blood and urinary mesna concentrations are more steady and prolonged after oral delivery compared with after intravenous delivery. (PMID: 16333822, 10193684, 1485175) [HMDB] Mesna is a chemoprotectant. Chemoprotectants have been developed as a means of ameliorating the toxicity associated with cytotoxic agents by providing site-specific protection for normal tissues, without compromising antitumour efficacy. Mesna eliminates the risk of therapy-limiting urotoxic side effects of oxazaphosphorines. Mesna is widely used for the prevention of cyclophosphamide-related hemorrhagic cystitis. It has been associated with hypersensitivity-like cutaneous and systemic reactions in adult patients. Mesna offers significant uroprotection in patients receiving high dose cyclophosphamide, and is widely used in paediatric oncology practice It is, therefore, important to recognize that it may be associated with a rare but significant systemic adverse reaction. A hypersensitivity-like reaction to mesna was first reported in a young adult receiving treatment for Hodgkin disease over 20 years ago. Oral administration of mesna can facilitate outpatient ifosfamide therapy. Blood and urinary mesna concentrations are more steady and prolonged after oral delivery compared with after intravenous delivery. (PMID: 16333822, 10193684, 1485175). Acquisition and generation of the data is financially supported in part by CREST/JST. D020011 - Protective Agents
2,3-Dimercapto-1-propanesulfonic acid
D064449 - Sequestering Agents > D002614 - Chelating Agents D020011 - Protective Agents > D000931 - Antidotes
N-Tetradecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate
C19H41NO3S (363.28069960000005)
2,2'-Dithiodiethanesulfonic acid
C4H10O6S4 (281.93602400000003)
D020011 - Protective Agents
Acamprosate
Acamprosate, also known by the brand name Campral™, is a drug used for treating alcohol dependence. Acamprosate is thought to stabilize the chemical balance in the brain that would otherwise be disrupted by alcoholism, possibly by blocking glutaminergic N-methyl-D-aspartate receptors, while gamma-aminobutyric acid type A receptors are activated. Reports indicate that acamprosate only works with a combination of attending support groups and abstinence from alcohol. Certain serious side effects include allergic reactions, irregular heartbeats, and low or high blood pressure, while less serious side effects include headaches, insomnia, and impotence. Acamprosate should not be taken by people with kidney problems or allergies to the drug. N - Nervous system > N07 - Other nervous system drugs > N07B - Drugs used in addictive disorders > N07BB - Drugs used in alcohol dependence D002491 - Central Nervous System Agents > D000427 - Alcohol Deterrents C26170 - Protective Agent > C1509 - Neuroprotective Agent
L-Homocysteine sulfonic acid
L-Homocysteine sulfonic acid is an oxydative metabolite of the amino acid homocystine that was found in the urine and blood of 2 mentally retarded children. (PMID: 5119311) [HMDB] L-Homocysteine sulfonic acid is an oxydative metabolite of the amino acid homocystine that was found in the urine and blood of 2 mentally retarded children. (PMID: 5119311).
2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid
2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid is a fda approved for use in polymer components of food-contact paper and board adhesive
N-Ornithyl-L-taurine
Proposed salt substitute especially for soy sauce. The originally-claimed saltiness at this compound was disputed, but has subsequently been confirmed. Proposed salt substitute especies for soy sauce. The originally-claimed saltiness at this compound was disputed, but has subsequently been confirmed.
N-Acetyltaurine
N-Acetyltaurine (also known as NAT) is a highly water-soluble and hygroscopic compound formed by the acetylation of taurine. It is both an endogenous metabolite that is constitutively synthesized in the body and an exogenous metabolite formed by ethanol metabolism. NAT is formed by one or multiple N-acetylation reactions between taurine and ethanol metabolites (primarily acetate). The enzyme responsible for NAT synthesis is called NAT synthase, a cytosolic metalloenzyme located in the kidney and liver that can directly catalyze the esterification reaction between taurine and acetate, without the involvement of ATP and CoA. NAT is a potential biomarker of hyperacetatemia as well as ethanol consumption (PMID: 22228769). NAT is typically found in human urine with normal concentrations of 0.599-1.38 umol/mmol creatinine in alcohol-abstinent subjects. NAT can reach average levels of 8.38 umol/mmol creatinine (range 5.39-10.47 umol/mmol creatinine) in subjects consuming alcohol within 3 to 6 h after the start of drinking. Positive NAT results can be used as an indicator for recent alcohol consumption (PMID: 27520321). NAT is considered a direct alcohol biomarker that specifically represents the oxidative pathway of ethanol metabolism. Other direct alcohol biomarkers such as fatty acid ethyl esters (FAEE), ethyl glucuronide, ethyl sulfate, and phosphatidylethanol reflect the non-oxidative pathway of alcohol metabolism. NAT is also elevated in urine after periods of endurance exercise. NAT was previously found in nature as a major component in the sticky droplet of orb spider web. Due to its high hygroscopicity, N-acetyltaurine appears to ensure the orb spider’s web flexibility.
N-Hexadecyl-N,N-dimethyl-3-ammonio-1-propanesulfonate
N-Chlorotaurine
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D004791 - Enzyme Inhibitors