Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2022-02-14 18:27:56 UTC |
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NP-MRD ID | NP0000409 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | L-Methionine |
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Description | Methionine (Met), also known as L-methionine, 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 (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. Methionine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Methionine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. Methionine is an essential amino acid (there are 9 essential amino acids), meaning the body cannot synthesize it, and it must be obtained from the diet. It is required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, methionine is an intermediate in transmethylation reactions, serving as the major methyl group donor in vivo, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate, and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine (PMID: 16702340 ). There is a general consensus concerning normal sulfur amino acid (SAA) requirements. WHO recommendations amount to 13 mg/kg per 24 h in healthy adults. This amount is roughly doubled in artificial nutrition regimens. In disease or after trauma, requirements may be altered for methionine, cysteine, and taurine. Although in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function, hypermethioninemia or hyperhomocysteinemia may occur, SAA supplementation can be considered safe in amounts exceeding 2-3 times the minimum recommended daily intake. Apart from some very specific indications (e.G. Acetaminophen poisoning) the usefulness of SAA supplementation is not yet established (PMID: 16702341 ). Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, but there is no evidence of similar effects in healthy subjects. The role of methionine as a precursor of homocysteine is the most notable cause for concern. Acute doses of methionine can lead to acute increases in plasma homocysteine, which can be used as an index of the susceptibility to cardiovascular disease. Sufficiently high doses of methionine can actually result in death. Longer-term studies in adults have indicated no adverse consequences of moderate fluctuations in dietary methionine intake, but intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346 ). When present in sufficiently high levels, methionine can act as an atherogen and a metabotoxin. An atherogen is a compound that when present at chronically high levels causes atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency. Chronically elevated levels of methionine in infants can lead to intellectual disability and other neurological problems, delays in motor skills, sluggishness, muscle weakness, and liver problems. Many individuals with these metabolic disorders tend to develop cardiovascular disease later in life. Studies on feeding rodents high levels of methionine have shown that methionine promotes atherosclerotic plaques independently of homocysteine levels (PMID: 26647293 ). A similar study in Finnish men showed the same effect (PMID: 16487911 ). |
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Structure | InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 |
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Synonyms | Value | Source |
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(2S)-2-Amino-4-(methylsulfanyl)butanoic acid | ChEBI | (S)-2-Amino-4-(methylthio)butanoic acid | ChEBI | (S)-2-Amino-4-(methylthio)butyric acid | ChEBI | (S)-Methionine | ChEBI | L-(-)-Methionine | ChEBI | L-alpha-Amino-gamma-methylmercaptobutyric acid | ChEBI | L-Methionin | ChEBI | M | ChEBI | Met | ChEBI | METHIONINE | ChEBI | L-2-Amino-4methylthiobutyric acid | Kegg | L-Methionine Z | Kegg | (2S)-2-Amino-4-(methylsulfanyl)butanoate | Generator | (2S)-2-Amino-4-(methylsulphanyl)butanoate | Generator | (2S)-2-Amino-4-(methylsulphanyl)butanoic acid | Generator | (S)-2-Amino-4-(methylthio)butanoate | Generator | (S)-2-Amino-4-(methylthio)butyrate | Generator | L-a-Amino-g-methylmercaptobutyrate | Generator | L-a-Amino-g-methylmercaptobutyric acid | Generator | L-alpha-Amino-gamma-methylmercaptobutyrate | Generator | L-Α-amino-γ-methylmercaptobutyrate | Generator | L-Α-amino-γ-methylmercaptobutyric acid | Generator | L-2-Amino-4methylthiobutyrate | Generator | (L)-Methionine | HMDB | (S)-(+)-Methionine | HMDB | (S)-2-Amino-4-(methylthio)-butanoate | HMDB | (S)-2-Amino-4-(methylthio)-butanoic acid | HMDB | 2-Amino-4-(methylthio)butyrate | HMDB | 2-Amino-4-(methylthio)butyric acid | HMDB | 2-Amino-4-methylthiobutanoate | HMDB | 2-Amino-4-methylthiobutanoic acid | HMDB | a-Amino-g-methylmercaptobutyrate | HMDB | a-Amino-g-methylmercaptobutyric acid | HMDB | Acimethin | HMDB | alpha-Amino-alpha-aminobutyric acid | HMDB | alpha-Amino-gamma-methylmercaptobutyrate | HMDB | alpha-Amino-gamma-methylmercaptobutyric acid | HMDB | Cymethion | HMDB | g-Methylthio-a-aminobutyrate | HMDB | g-Methylthio-a-aminobutyric acid | HMDB | gamma-Methylthio-alpha-aminobutyrate | HMDB | gamma-Methylthio-alpha-aminobutyric acid | HMDB | H-Met-H | HMDB | H-Met-OH | HMDB | L(-)-Amino-alpha-amino-alpha-aminobutyric acid | HMDB | L(-)-Amino-gamma-methylthiobutyric acid | HMDB | L-2-Amino-4-(methylthio)butyric acid | HMDB | L-2-Amino-4-methylthiobutyric acid | HMDB | L-a-Amino-g-methylthiobutyrate | HMDB | L-a-Amino-g-methylthiobutyric acid | HMDB | L-alpha-Amino-gamma-methylthiobutyrate | HMDB | L-alpha-Amino-gamma-methylthiobutyric acid | HMDB | L-gamma-Methylthio-alpha-aminobutyric acid | HMDB | L-Methioninum | HMDB | Liquimeth | HMDB | Mepron | HMDB | Methilanin | HMDB | Methioninum | HMDB | Metionina | HMDB | Neo-methidin | HMDB | Poly-L-methionine | HMDB | Polymethionine | HMDB | S-Methionine | HMDB | S-Methyl-L-homocysteine | HMDB | Toxin war | HMDB | L-Isomer methionine | HMDB | Methionine, L-isomer | HMDB | Pedameth | HMDB | Methionine, L isomer | HMDB | (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diol | HMDB | Bo-xan | HMDB | e 161b | HMDB | Xanthophyll | HMDB | (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol | HMDB | (3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol | HMDB |
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Chemical Formula | C5H11NO2S |
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Average Mass | 149.2110 Da |
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Monoisotopic Mass | 149.05105 Da |
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IUPAC Name | (2S)-2-amino-4-(methylsulfanyl)butanoic acid |
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Traditional Name | L-methionine |
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CAS Registry Number | 63-68-3 |
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SMILES | CSCC[C@H](N)C(O)=O |
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InChI Identifier | InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 |
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InChI Key | FFEARJCKVFRZRR-BYPYZUCNSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-02-14 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-07-29 | View Spectrum |
| Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Methionine and derivatives |
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Alternative Parents | |
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Substituents | - Methionine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Thia fatty acid
- Fatty acid
- Fatty acyl
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Thioether
- Sulfenyl compound
- Dialkylthioether
- Amine
- Organic oxygen compound
- Primary amine
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 284 °C | Not Available | Boiling Point | 306.00 to 308.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 56.6 mg/mL | Yalkowsky, S. H., & Dannenfelser, R. M. (1992). Aquasol database of aqueous solubility. College of Pharmacy, University of Arizona, Tucson, AZ, 189. | LogP | -1.87 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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Predicted Properties | |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
- Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
- Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
- Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
- Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
- Kersemans V, Cornelissen B, Kersemans K, Bauwens M, Achten E, Dierckx RA, Mertens J, Slegers G: In vivo characterization of 123/125I-2-iodo-L-phenylalanine in an R1M rhabdomyosarcoma athymic mouse model as a potential tumor tracer for SPECT. J Nucl Med. 2005 Mar;46(3):532-9. [PubMed:15750170 ]
- Alme B, Bremmelgaard A, Sjovall J, Thomassen P: Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry. J Lipid Res. 1977 May;18(3):339-62. [PubMed:864325 ]
- Sardharwalla IB, Fowler B, Robins AJ, Komrower GM: Detection of heterozygotes for homocystinuria. Study of sulphur-containing amino acids in plasma and urine after L-methionine loading. Arch Dis Child. 1974 Jul;49(7):553-9. [PubMed:4851308 ]
- Alton KB, Hernandez A, Alvarez N, Patrick JE: High-performance liquid chromatographic determination of N-[2(S)-(mercaptomethyl)-3-(2-methylphenyl)-1-oxopropyl]-L-methionine, the active plasma metabolite of a prodrug atriopeptidase inhibitor (SCH 42495), using a thiol selective (Au/Hg) amperometric detector. J Chromatogr. 1992 Sep 2;579(2):307-17. [PubMed:1429978 ]
- Fischer JL, Lancia JK, Mathur A, Smith ML: Selenium protection from DNA damage involves a Ref1/p53/Brca1 protein complex. Anticancer Res. 2006 Mar-Apr;26(2A):899-904. [PubMed:16619485 ]
- Ditscheid B, Funfstuck R, Busch M, Schubert R, Gerth J, Jahreis G: Effect of L-methionine supplementation on plasma homocysteine and other free amino acids: a placebo-controlled double-blind cross-over study. Eur J Clin Nutr. 2005 Jun;59(6):768-75. [PubMed:15870821 ]
- Hesse A, Heimbach D: Causes of phosphate stone formation and the importance of metaphylaxis by urinary acidification: a review. World J Urol. 1999 Oct;17(5):308-15. [PubMed:10552150 ]
- Harth G, Horwitz MA: Inhibition of Mycobacterium tuberculosis glutamine synthetase as a novel antibiotic strategy against tuberculosis: demonstration of efficacy in vivo. Infect Immun. 2003 Jan;71(1):456-64. [PubMed:12496196 ]
- Takasu A, Shimosegawa T, Shimosegawa E, Hatazawa J, Kimura K, Fujita M, Koizumi M, Kanno I, Toyota T: 11C-methionine uptake to the pancreas and its secretion: a positron emission tomography study in humans. Pancreas. 1999 May;18(4):392-8. [PubMed:10231845 ]
- Ball RO, Courtney-Martin G, Pencharz PB: The in vivo sparing of methionine by cysteine in sulfur amino acid requirements in animal models and adult humans. J Nutr. 2006 Jun;136(6 Suppl):1682S-1693S. [PubMed:16702340 ]
- van de Poll MC, Dejong CH, Soeters PB: Adequate range for sulfur-containing amino acids and biomarkers for their excess: lessons from enteral and parenteral nutrition. J Nutr. 2006 Jun;136(6 Suppl):1694S-1700S. [PubMed:16702341 ]
- Garlick PJ: Toxicity of methionine in humans. J Nutr. 2006 Jun;136(6 Suppl):1722S-1725S. [PubMed:16702346 ]
- Selhub J, Troen AM: Sulfur amino acids and atherosclerosis: a role for excess dietary methionine. Ann N Y Acad Sci. 2016 Jan;1363:18-25. doi: 10.1111/nyas.12962. Epub 2015 Dec 8. [PubMed:26647293 ]
- Virtanen JK, Voutilainen S, Rissanen TH, Happonen P, Mursu J, Laukkanen JA, Poulsen H, Lakka TA, Salonen JT: High dietary methionine intake increases the risk of acute coronary events in middle-aged men. Nutr Metab Cardiovasc Dis. 2006 Mar;16(2):113-20. doi: 10.1016/j.numecd.2005.05.005. Epub 2005 Nov 2. [PubMed:16487911 ]
- Li Y, Jin Y, Kuang L, Luo Z, Li F, Sun J, Zhu A, Zhuang Z, Wang Y, Wen L, Liu D, Chen C, Gan M, Zhao J, Zhao J: The N-Terminal Region of Middle East Respiratory Syndrome Coronavirus Accessory Protein 8b Is Essential for Enhanced Virulence of an Attenuated Murine Coronavirus. J Virol. 2022 Feb 9;96(3):e0184221. doi: 10.1128/JVI.01842-21. Epub 2021 Nov 24. [PubMed:34817197 ]
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