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24/9/2020 Methionine | C5H11NO2S - PubChem COMPOUND SUMMARY Methionine PubChem CID: 6137 Structure: 2D 3D Crystal Find Similar Structures Chemical Safety: Laboratory Chemical Safety Summary (LCSS) Datasheet Molecular Formula: C5H11NO2S L-methionine 63-68-3 methionine Synonyms: h-Met-oh (S)-2-Amino-4-(methylthio)butanoic acid More... Molecular Weight: 149.21 g/mol Modify: Create: Dates: 2020-09-19 2004-09-16 Methionine is one of nine essential amino acids in humans (provided by food), Methionine is required for growth and tissue repair. A sulphur-containing amino acid, methionine improves the tone and pliability of skin, hair, and strengthens nails. Involved in many detoxifying processes, sulphur provided by methionine protects cells from pollutants, slows cell aging, and is essential for absorption and bio-availability of selenium and zinc. Methionine chelates heavy metals, such as lead and mercury, aiding their excretion. It also acts as a lipotropic agent and prevents excess fat buildup in the liver. (NCI04) NCI Thesaurus (NCIt) L-Methionine, also known as liquimeth or pedameth, belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Methionine is a drug which is used for protein synthesis including the formation of same, l-homocysteine, l-cysteine, taurine, and sulfate. L-Methionine exists as a solid, soluble (in water), and a moderately acidic compound (based on its pKa). L-Methionine has been found throughout most human tissues, and has also been detected in most biofluids, including feces, cerebrospinal fluid, saliva, and blood. Within the cell, L-methionine is primarily located in the mitochondria and cytoplasm. L-Methionine exists in all eukaryotes, ranging from yeast to humans. Dimethylglycine and L-methionine can be biosynthesized from betaine and homocysteine; which is mediated by the enzyme betaine--homocysteine S- methyltransferase 1. In humans, L-methionine is involved in spermidine and spermine biosynthesis pathway, the arbekacin action pathway, the lincomycin action pathway, and the tobramycin action pathway. L-Methionine is also involved in several metabolic disorders, some of which include S-adenosylhomocysteine (sah) hydrolase deficiency, cystathionine Beta- synthase deficiency, the hypermethioninemia pathway, and the homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, CBLG complementation type pathway. L- Methionine is a potentially toxic compound. Human Metabolome Database (HMDB) L-methionine is the L-enantiomer of methionine. It has a role as a nutraceutical, a micronutrient, an antidote to paracetamol poisoning, a human metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, a methionine and a L-alpha-amino acid. It is a conjugate base of a L-methioninium. It is a conjugate acid of a L-methioninate. It is an enantiomer of a D-methionine. It is a tautomer of a L-methionine zwitterion. ChEBI https://pubchem.ncbi.nlm.nih.gov/compound/6137 1/57 24/9/2020 Methionine | C5H11NO2S - PubChem 1 Structures 1.1 2D Structure Chemical Structure Depiction PubChem 1.2 3D Conformer PubChem 1.3 Crystal Structures Showing 1 of 2 View More CCDC Number 276855 Crystal Structure Data DOI:10.5517/cc992tg Crystal Structure Depiction The Cambridge Structural Database https://pubchem.ncbi.nlm.nih.gov/compound/6137 2/57 24/9/2020 Methionine | C5H11NO2S - PubChem 2 Biologic Description SVG Image IUPAC Condensed H-Met-OH Sequence M PLN H-M-OH HELM PEPTIDE1{M}$$$$ IUPAC L-methionine PubChem https://pubchem.ncbi.nlm.nih.gov/compound/6137 3/57 24/9/2020 Methionine | C5H11NO2S - PubChem 3 Names and Identifiers 3.1 Computed Descriptors 3.1.1 IUPAC Name (2S)-2-amino-4-methylsulfanylbutanoic acid Computed by LexiChem 2.6.6 (PubChem release 2019.06.18) PubChem 3.1.2 InChI InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 Computed by InChI 1.0.5 (PubChem release 2019.06.18) PubChem 3.1.3 InChI Key FFEARJCKVFRZRR-BYPYZUCNSA-N Computed by InChI 1.0.5 (PubChem release 2019.06.18) PubChem 3.1.4 Canonical SMILES CSCCC(C(=O)O)N Computed by OEChem 2.1.5 (PubChem release 2019.06.18) PubChem 3.1.5 Isomeric SMILES CSCC[C@@H](C(=O)O)N Computed by OEChem 2.1.5 (PubChem release 2019.06.18) PubChem 3.2 Molecular Formula C5H11NO2S Wikipedia; PubChem 3.3 Other Identifiers 3.3.1 CAS 63-68-3 CAMEO Chemicals; ChemIDplus; DrugBank; DTP/NCI; EPA Chemicals under the TSCA; EPA DSSTox; European Chemicals Agency (ECHA); Hazardous Substances Data Bank (HSDB); Human Metabolome Database (HMD 3654-96-4 ChemIDplus 58576-49-1 ChemIDplus 3.3.2 Deprecated CAS 24425-78-3, 7005-18-7, 1437749-32-0, 1437749-60-4, 1437749-65-9, 1437749-75-1, 1437749-80-8, 1437769-00-0, 1437870-94-4, 1437870-95-5, 1437870-97-7, 1437870-98-8, 1437871-20-9, 1463481-01-7, 1463481-06-2, 1463481-15-3, 1463481-19-7, 1463481-23-3, 1463481-27-7, 1463481-31-3, 1463481-37-9, 1463481-41-5, 1463481-46-0, 1463481-51-7, 1463481-58-4, 1463481- 73-3, 1463481-80-2, 1463481-89-1, 1463610-75-4, 1463610-76-5, 1466415-57-5 ChemIDplus 3.3.3 European Community (EC) Number 200-562-9 European Chemicals Agency (ECHA) 3.3.4 NSC Number 760117 DTP/NCI https://pubchem.ncbi.nlm.nih.gov/compound/6137 4/57 24/9/2020 Methionine | C5H11NO2S - PubChem 3.3.5 UNII AE28F7PNPL FDA/SPL Indexing Data 3.3.6 DSSTox Substance ID DTXSID5040548 EPA DSSTox 3.3.7 Wikipedia Methionine Wikipedia L-methionine Wikipedia 3.4 Synonyms 3.4.1 MeSH Entry Terms L-Isomer Methionine L-Methionine Liquimeth Methionine Methionine, L Isomer Methionine, L-Isomer Pedameth MeSH 3.4.2 Depositor-Supplied Synonyms L-methionine Methionine (VAN) Poly-L-methionine 2-Amino-4-(methylthio)butyric acid, (S)- NSC 2294 63-68-3 Acimethin L(-)-Amino-gamma-methylthiobutyric acid (2S)-2-amino-4-methylsulfanyl-butanoic acid AE28F7PN methionine Metionina [DCIT] L-alpha-Amino-gamma-methylthiobutyric acid L-Met gamma-M h-Met-oh (S)-methionine L-gamma-Methylthio-alpha-aminobutyric acid Butanoic acid, 2-amino-4-(methylthio)-, (S)- L-2-Amino (S)-2-Amino-4-(methylthio)butanoic acid L-alpha-Amino-gamma-methylmercaptobutyric acid met Methionine C 11 CHEMBL4 L-(-)-Methionine h-Met-h CCRIS 5528 Toxin WAR (Bacillus thuringiensis strain PS205C) CHEBI:166 Cymethion Methioninum [INN-Latin] CCRIS 5536 (2S)-2-Amino-4-methylsulfanylbutanoic acid L-2-Amino Liquimeth (2S)-2-amino-4-(methylsulfanyl)butanoic acid METHIONINE, L- L-a-Amino-g-methylthiobutyric acid L-Methion S-Methionine metionina HSDB 4317 carbon-11 methionine (S)-2-Ami L-Methioninum Methioninum 2-Amino-4-methylthiobutanoic acid (S)- S-Methyl-L-homocysteine C-11 Meth Methilanin Polymethionine Methionine [USAN:INN] (S)-(+)-Methionine 58576-49- Neo-methidin L-Homocysteine, S-methyl- UNII-AE28F7PNPL EINECS 200-562-9 l-2-Amino (L)-Methionine L-Methionin (S)-2-amino-4-(methylthio)butyric acid MFCD00063097 L-Methion PubChem https://pubchem.ncbi.nlm.nih.gov/compound/6137 5/57 24/9/2020 Methionine | C5H11NO2S - PubChem 4 Chemical and Physical Properties 4.1 Computed Properties Property Name Property Value Reference Molecular Weight 149.21 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) XLogP3 -1.9 Computed by XLogP3 3.0 (PubChem release 2019.06.18) Hydrogen Bond Donor Count 2 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Hydrogen Bond Acceptor Count 4 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Rotatable Bond Count 4 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Exact Mass 149.05105 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Monoisotopic Mass 149.05105 g/mol Computed by PubChem 2.1 (PubChem release 2019.06.18) Topological Polar Surface Area 88.6 Ų Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Heavy Atom Count 9 Computed by PubChem Formal Charge 0 Computed by PubChem Complexity 97 Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18) Isotope Atom Count 0 Computed by PubChem Defined Atom Stereocenter Count 1 Computed by PubChem Undefined Atom Stereocenter Count 0 Computed by PubChem Defined Bond Stereocenter Count 0 Computed by PubChem Undefined Bond Stereocenter Count 0 Computed by PubChem Covalently-Bonded Unit Count 1 Computed by PubChem Compound Is Canonicalized Yes Computed by PubChem (release 2019.01.04) PubChem 4.2 Experimental Properties 4.2.1 Physical Description Minute hexagonal plates from dilute alcohol. (NTP, 1992) National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. CAMEO Chemicals Solid Human Metabolome Database (HMDB) 4.2.2 Color/Form Minute hexagonal plates from dilute alcohol O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1032 Hazardous Substances Data Bank (HSDB) Colorless or white, lustrous plates or as white, crystalline powder FCC; Food Chemicals Codex. Committee on Food Chemicals Codex, Food and Nutrition Board, Institute of Medicine. 5th. Washington, DC: National Academy Press p. 286 (2003) Hazardous Substances Data Bank (HSDB) 4.2.3 Odor Faint Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 752 Hazardous Substances Data Bank (HSDB) 4.2.4 Taste Sulfurous Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry.
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    Our Dermatology Online Original Article SSodiumodium mmetabisulfietabisulfi ttee hhypersensitivityypersensitivity iinn uurticariarticaria Beata Sadowska, Marlena Sztormowska, Marika Gawinowska, Marta Chelminska Department of Allergology, Allergology and Pneumonology Clinic, Medical University of Gdansk, Smoluchowskiego 17, 80- 214 Gdansk, Poland Corresponding author: Beata Sadowska, MD, E-mail: [email protected] ABSTRACT Background: Sodium metabisulfite is a recognized, but rare, trigger of urticaria, wherein the IgE mechanism has been sporadically proven. The aim of this study was to identify the potential reaction to sodium metabisulfite (MBS) based on a placebo-controlled oral challenge in patients with urticaria and suspected hypersensitivity to food additives. Materials and Methods: A total of 110 adult patients (76 females and 34 males with a mean age of 46 years) were included in the study between 2017 and 2019. All subjects underwent MBS skin prick tests (SPT) and patch tests (PT). Patients with a positive skin test or suspected MBS hypersensitivity were qualified for a placebo-controlled oral challenge (OC). Results: Skin testing was positive in 24 patients: SPT in 20% (n = 22), PT in 5% (n = 6). Out of 64 oral challenges, 13 positive results were obtained. Patients with a positive challenge typed sulfite foods twice as often as a culprit compared to those with a negative OC. Conclusions: In patients with urticaria, both the IgE and non-IgE mechanism of MBS hypersensitivity has been demonstrated. Skin tests with a detailed medical history of potentially guilty foods may be helpful in determining sulfite hypersensitivity. Key words: Sulfites; Sodium metabisulfite; Urticaria; Food additive hypersensitivity INTRODUCTION they are not obliged to disclose the total amount of the substance [5].
  • Methylmalonyl-Coa Mutase Induction by Cerebral Ischemia and Neurotoxicity of the Mitochondrial Toxin Methylmalonic Acid

    Methylmalonyl-Coa Mutase Induction by Cerebral Ischemia and Neurotoxicity of the Mitochondrial Toxin Methylmalonic Acid

    The Journal of Neuroscience, November 15, 1996, 16(22):7336–7346 Methylmalonyl-CoA Mutase Induction by Cerebral Ischemia and Neurotoxicity of the Mitochondrial Toxin Methylmalonic Acid Purnima Narasimhan, Robert Sklar, Matthew Murrell, Raymond A. Swanson, and Frank R. Sharp Department of Neurology, University of California, San Francisco, San Francisco, California 94143, and Department of Veterans Affairs Medical Center, San Francisco, California 94121 Differential screening of gerbil brain hippocampal cDNA librar- (SDH), produced dose-related cell death when injected into the ies was used to search for genes expressed in ischemic, but basal ganglia of adult rat brain. This neurotoxicity is similar to that not normal, brain. The methylmalonyl-CoA mutase (MCM) of structurally related mitochondrial SDH inhibitors, malonate and cDNA was highly expressed after ischemia and showed a 95% 3-nitropropionic acid. Methylmalonic acid may contribute to neu- similarity to mouse and 91% similarity to the human MCM ronal injury in human conditions in which it accumulates, including cDNAs. Transient global ischemia induced a fourfold increase MCM mutations and B12 deficiency. This study shows that in MCM mRNA on Northern blots from both hippocampus and methylmalonyl-CoA mutase is induced by several stresses, in- whole forebrain. MCM protein exhibited a similar induction on cluding ischemia, and would serve to decrease the accumulation Western blots of gerbil cerebral cortex 8 and 24 hr after isch- of an endogenous cellular mitochondrial inhibitor and neurotoxin, emia. Treatment of primary brain astrocytes with either the methylmalonic acid. branched-chain amino acid (BCAA) isoleucine or the BCAA metabolite, propionate, induced MCM mRNA fourfold. In- creased concentrations of BCAAs and odd-chain fatty acids, Key words: methylmalonic acid; methylmalonyl-CoA mutase; both of which are metabolized to propionate, may contribute to branched-chain amino acids; odd-chain fatty acids; propionate; inducing the MCM gene during ischemia.