L-Methionine
Relevant Data
Food Additives Approved in the United States:
General Information
| Chemical name | L-Methionine |
| CAS number | 63-68-3 |
| Flavouring type | substances |
| FL No. | 17.027 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified | |
| Reference body | EFSA |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6137 |
| IUPAC Name | (2S)-2-amino-4-methylsulfanylbutanoic acid |
| InChI | InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 |
| InChI Key | FFEARJCKVFRZRR-BYPYZUCNSA-N |
| Canonical SMILES | CSCCC(C(=O)O)N |
| Molecular Formula | C5H11NO2S |
| Wikipedia | L-Methionine |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 149.208 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Complexity | 97.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B i M A B A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g Q Q C A A A C C j F w A S C C A B A A g g I A A C Q C A A A A A A A A B A A A I G A A A A C A B A g A A A A Q A A E E A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 88.6 |
| Monoisotopic Mass | 149.051 |
| Exact Mass | 149.051 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8447 |
| Human Intestinal Absorption | HIA+ | 0.9797 |
| Caco-2 Permeability | Caco2- | 0.6698 |
| P-glycoprotein Substrate | Non-substrate | 0.5351 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9802 |
| Non-inhibitor | 0.9919 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8913 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7116 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7875 |
| CYP450 2D6 Substrate | Non-substrate | 0.7323 |
| CYP450 3A4 Substrate | Non-substrate | 0.7008 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8295 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9489 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9567 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9510 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9758 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9938 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9725 |
| Non-inhibitor | 0.9655 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.9224 |
| Fish Toxicity | High FHMT | 0.5404 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9795 |
| Honey Bee Toxicity | Low HBT | 0.6249 |
| Biodegradation | Ready biodegradable | 0.5613 |
| Acute Oral Toxicity | IV | 0.6189 |
| Carcinogenicity (Three-class) | Non-required | 0.7474 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.3574 | LogS |
| Caco-2 Permeability | 0.6100 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 0.6483 | LD50, mol/kg |
| Fish Toxicity | 2.9492 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.8015 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Absorbed from the lumen of the small intestine into the enterocytes by an active transport process. |
|---|---|
| Mechanism of Toxicity | The mechanism of the possible anti-hepatotoxic activity of L-methionine is not entirely clear. It is thought that metabolism of high doses of acetaminophen in the liver lead to decreased levels of hepatic glutathione and increased oxidative stress. L-methionine is a precursor to L-cysteine. L-cysteine itself may have antioxidant activity. L-cysteine is also a precursor to the antioxidant glutathione. Antioxidant activity of L-methionine and metabolites of L-methionine appear to account for its possible anti-hepatotoxic activity. Recent research suggests that methionine itself has free-radical scavenging activity by virtue of its sulfur, as well as its chelating ability. |
| Metabolism | Hepatic |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | Chronically high levels of methionine are associated with at least 7 inborn errors of metabolism including: Cystathionine Beta-Synthase Deficiency, Glycine N-methyltransferase Deficiency, Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, Methionine Adenosyltransferase Deficiency, Methylenetetrahydrofolate reductase deficiency and S-Adenosylhomocysteine (SAH) Hydrolase Deficiency. |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives |
| Direct Parent | Methionine and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as methionine and derivatives. These 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. |
From ClassyFire
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline.
- Gene Name:
- BHMT
- Uniprot ID:
- Q93088
- Molecular Weight:
- 44998.205 Da
References
- Hazra A, Wu K, Kraft P, Fuchs CS, Giovannucci EL, Hunter DJ: Twenty-four non-synonymous polymorphisms in the one-carbon metabolic pathway and risk of colorectal adenoma in the Nurses' Health Study. Carcinogenesis. 2007 Jul;28(7):1510-9. Epub 2007 Mar 26. [17389618 ]
- General Function:
- Poly(a) rna binding
- Specific Function:
- Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala-, Cys, Gly, Pro, Ser, Thr, or Val). The catalytic activity of human METAP2 toward Met-Val peptides is consistently two orders of magnitude higher than that of METAP1, suggesting that it is responsible for processing proteins containing N-terminal Met-Val and Met-Thr sequences in vivo.Protects eukaryotic initiation factor EIF2S1 from translation-inhibiting phosphorylation by inhibitory kinases such as EIF2AK2/PKR and EIF2AK1/HCR. Plays a critical role in the regulation of protein synthesis.
- Gene Name:
- METAP2
- Uniprot ID:
- P50579
- Molecular Weight:
- 52891.145 Da
References
- Nonato MC, Widom J, Clardy J: Human methionine aminopeptidase type 2 in complex with L- and D-methionine. Bioorg Med Chem Lett. 2006 May 15;16(10):2580-3. Epub 2006 Mar 15. [16540317 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
- Gene Name:
- MTR
- Uniprot ID:
- Q99707
- Molecular Weight:
- 140525.91 Da
References
- Yamada K, Kawata T, Wada M, Mori K, Tamai H, Tanaka N, Tadokoro T, Tobimatsu T, Toraya T, Maekawa A: Testicular injury to rats fed on soybean protein-based vitamin B12-deficient diet can be reduced by methionine supplementation. J Nutr Sci Vitaminol (Tokyo). 2007 Apr;53(2):95-101. [17615995 ]
- General Function:
- Oxidoreductase activity, oxidizing metal ions, nad or nadp as acceptor
- Specific Function:
- Involved in the reductive regeneration of cob(I)alamin (vitamin B12) cofactor required for the maintenance of methionine synthase in a functional state. Necessary for utilization of methylgroups from the folate cycle, thereby affecting transgenerational epigenetic inheritance. Folate pathway donates methyl groups necessary for cellular methylation and affects different pathways such as DNA methylation, possibly explaining the transgenerational epigenetic inheritance effects.
- Gene Name:
- MTRR
- Uniprot ID:
- Q9UBK8
- Molecular Weight:
- 80409.22 Da
References
- Elmore CL, Wu X, Leclerc D, Watson ED, Bottiglieri T, Krupenko NI, Krupenko SA, Cross JC, Rozen R, Gravel RA, Matthews RG: Metabolic derangement of methionine and folate metabolism in mice deficient in methionine synthase reductase. Mol Genet Metab. 2007 May;91(1):85-97. Epub 2007 Mar 21. [17369066 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Involved in the regulation of homocysteine metabolism. Converts homocysteine to methionine using S-methylmethionine (SMM) as a methyl donor.
- Gene Name:
- BHMT2
- Uniprot ID:
- Q9H2M3
- Molecular Weight:
- 40353.84 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
From T3DB