ChemFOnt: Showing chemical card for L-Methionine (CFc000000548)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:58 UTC

Chemfont ID

CFc000000548

Molecule Identification

Common Name

L-Methionine

Definition

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 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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	ChEBI
Bo-xan	ChEBI
e 161b	ChEBI
Xanthophyll	ChEBI
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diol	Generator
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diol	Generator

Chemical Formula

C₅H₁₁NO₂S

Average Molecular Weight

149.211

Monoisotopic Molecular Weight

149.051049291

IUPAC Name

(2S)-2-amino-4-(methylsulfanyl)butanoic acid

Traditional Name

L-methionine

CAS Registry Number

63-68-3

SMILES

CSCC[C@H](N)C(O)=O

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

InChI Key

FFEARJCKVFRZRR-BYPYZUCNSA-N

Chemical Taxonomy

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.

Showing chemical card for L-Methionine (CFc000000548)

MOL for CFc000000548 (L-Methionine)

3D MOL for CFc000000548 (L-Methionine)

3D SDF for CFc000000548 (L-Methionine)

3D-SDF for CFc000000548 (L-Methionine)

PDB for CFc000000548 (L-Methionine)

3D PDB for CFc000000548 (L-Methionine)

SMILES for CFc000000548 (L-Methionine)

INCHI for CFc000000548 (L-Methionine)

Structure for CFc000000548 (L-Methionine)

3D Structure for CFc000000548 (L-Methionine)