Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000175
Identification
Name: L-Methionine
Description:L-Methionine, in addition to being a substrate for protein synthesis, is an intermediate in transmethylation reactions, serving as the major methyl group donor, including the methyl groups for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyl transferase (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 also required for synthesis of cysteine. Methionine is accepted as 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)
Structure
Thumb
Synonyms:
  • (2S)-2-amino-4-(methylsulfanyl)butanoate
  • (2S)-2-amino-4-(methylsulfanyl)butanoic acid
  • (2S)-2-amino-4-(methylsulphanyl)butanoate
  • (2S)-2-amino-4-(methylsulphanyl)butanoic acid
  • (L)-methionine
  • (S)-(+)-methionine
  • (S)-2-amino-4-(methylthio)-Butanoate
  • (S)-2-amino-4-(methylthio)-Butanoic acid
  • (S)-2-Amino-4-(methylthio)butanoate
  • (S)-2-Amino-4-(methylthio)butanoic acid
  • (S)-2-amino-4-(methylthio)butyrate
  • (S)-2-amino-4-(methylthio)butyric acid
  • (S)-methionine
  • 2-Amino-4-(methylthio)butyrate
  • 2-Amino-4-(methylthio)butyric acid
  • 2-Amino-4-methylthiobutanoate
  • 2-Amino-4-methylthiobutanoic acid
  • a-amino-a-Aminobutyrate
  • a-amino-a-Aminobutyric acid
  • A-Amino-g-methylmercaptobutyrate
  • A-Amino-g-methylmercaptobutyric acid
  • Acimethin
  • Alpha-Amino-alpha-aminobutyrate
  • Alpha-Amino-alpha-aminobutyric acid
  • Alpha-Amino-gamma-methylmercaptobutyrate
  • Alpha-Amino-gamma-methylmercaptobutyric acid
  • Cymethion
  • G-Methylthio-a-aminobutyrate
  • G-Methylthio-a-aminobutyric acid
  • Gamma-Methylthio-alpha-aminobutyrate
  • Gamma-Methylthio-alpha-aminobutyric acid
  • H-Met-h
  • H-Met-oh
  • L(-)-amino-a-amino-a-Aminobutyrate
  • L(-)-amino-a-amino-a-Aminobutyric acid
  • L(-)-Amino-alpha-amino-alpha-aminobutyrate
  • L(-)-Amino-alpha-amino-alpha-aminobutyric acid
  • L(-)-amino-g-Methylthiobutyrate
  • L(-)-amino-g-Methylthiobutyric acid
  • L(-)-Amino-gamma-methylthiobutyrate
  • L(-)-Amino-gamma-methylthiobutyric acid
  • L(-)-amino-α-amino-α-Aminobutyrate
  • L(-)-amino-α-amino-α-Aminobutyric acid
  • L(-)-amino-γ-Methylthiobutyrate
  • L(-)-amino-γ-Methylthiobutyric acid
  • L-(-)-Methionine
  • L-2-Amino-4-(methylthio)butyrate
  • L-2-Amino-4-(methylthio)butyric acid
  • L-2-amino-4-Methylthiobutyrate
  • L-2-Amino-4-methylthiobutyric acid
  • L-2-Amino-4methylthiobutyrate
  • L-2-Amino-4methylthiobutyric acid
  • L-a-amino-g-Methylmercaptobutyrate
  • L-a-amino-g-Methylmercaptobutyric acid
  • L-a-Amino-g-methylthiobutyrate
  • L-a-Amino-g-methylthiobutyric acid
  • L-alpha-Amino-gamma-methylmercaptobutyrate
  • L-alpha-Amino-gamma-methylmercaptobutyric acid
  • L-alpha-Amino-gamma-methylthiobutyrate
  • L-alpha-Amino-gamma-methylthiobutyric acid
  • L-g-methylthio-a-Aminobutyrate
  • L-g-methylthio-a-Aminobutyric acid
  • L-gamma-Methylthio-alpha-aminobutyrate
  • L-gamma-Methylthio-alpha-aminobutyric acid
  • L-Methionin
  • L-Methionine
  • L-Methioninum
  • L-α-amino-γ-Methylmercaptobutyrate
  • L-α-amino-γ-Methylmercaptobutyric acid
  • L-α-amino-γ-Methylthiobutyrate
  • L-α-amino-γ-Methylthiobutyric acid
  • L-γ-methylthio-α-Aminobutyrate
  • L-γ-methylthio-α-Aminobutyric acid
  • Liquimeth
  • M
  • Mepron
  • MET
  • Methilanin
  • Methionine
  • Methioninum
  • Metionina
  • Neo-methidin
  • Poly-L-methionine
  • Polymethionine
  • S-Methionine
  • S-Methyl-L-homocysteine
  • Toxin WAR
  • α-amino-α-Aminobutyrate
  • α-amino-α-Aminobutyric acid
  • α-amino-γ-Methylmercaptobutyrate
  • α-amino-γ-Methylmercaptobutyric acid
  • γ-methylthio-α-Aminobutyrate
  • γ-methylthio-α-Aminobutyric acid
Chemical Formula: C5H11NO2S
Average Molecular Weight: 149.211
Monoisotopic Molecular Weight: 149.051049291
InChI Key: FFEARJCKVFRZRR-BYPYZUCNSA-N
InChI:InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
CAS number: 63-68-3
IUPAC Name:(2S)-2-amino-4-(methylsulfanyl)butanoic acid
Traditional IUPAC Name: L-methionine
SMILES:CSCC[C@H](N)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent D-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Methionine or derivatives
  • Thia fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 284 °C
Experimental Properties:
PropertyValueSource
Water Solubility:56.6 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 56.6 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-1.87 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility23.9 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.2ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.59 m3·mol-1ChemAxon
Polarizability15.5 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Methionine sulfoxide + Reduced Thioredoxin > Water + L-Methionine + Oxidized Thioredoxin
Adenosine triphosphate + Water + L-Methionine > ADP + Hydrogen ion + L-Methionine + Phosphate
Adenosine triphosphate + Water + L-Methionine > ADP + Hydrogen ion + L-Methionine + Phosphate
5-Methyltetrahydrofolic acid + L-Homocysteine <> Hydrogen ion + L-Methionine + Tetrahydrofolic acid
L-Homocysteine + S-Methylmethionine > Hydrogen ion +2 L-Methionine
S-Adenosylmethionine + L-Homocysteine + S-Methylmethionine <> S-Adenosylhomocysteine + Hydrogen ion + L-Methionine
[4Fe-4S] iron-sulfur cluster + 2 S-Adenosylmethionine + Hydrogen ion + NAD + octanoate (protein bound) > [2Fe-2S] iron-sulfur cluster +2 5'-Deoxyadenosine +2 Iron + lipoate (protein bound) +2 L-Methionine + NADH
[2Fe-2S] iron-sulfur cluster + S-Adenosylmethionine + Dethiobiotin > [2Fe-1S] desulfurated iron-sulfur cluster + Biotin + 5'-Deoxyadenosine + Hydrogen ion + L-Methionine
Adenosine triphosphate + L-Methionine + tRNA(Met) > Adenosine monophosphate + L-Methionyl-tRNA (Met) + Pyrophosphate
Adenosine triphosphate + Water + L-Methionine <> S-Adenosylmethionine + Phosphate + Pyrophosphate
2 S-Adenosylmethionine + Coproporphyrin III <>2 Carbon dioxide +2 5'-Deoxyadenosine +2 L-Methionine + Protoporphyrinogen IX
S-Adenosylmethionine + NADPH + L-Tyrosine > p-Cresol + 5'-Deoxyadenosine + Dehydroglycine + Hydrogen ion + L-Methionine + NADP
Hydrogen peroxide + L-Methionine > Water + Methionine sulfoxide
S-Adenosylmethionine + L-Homocysteine <> S-Adenosylhomocysteine + L-Methionine
5-Methyltetrahydrofolic acid + L-Homocysteine <> Tetrahydrofolic acid + L-Methionine
Dethiobiotin + Sulfur donor + 2 S-Adenosylmethionine + 2 e- + 2 Hydrogen ion <> Biotin +2 L-Methionine +2 5'-Deoxyadenosine
4-Amino-5-hydroxymethyl-2-methylpyrimidine + S-Adenosylmethionine <> 5-Aminoimidazole ribonucleotide + 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + CO
Adenosine triphosphate + L-Methionine + tRNA(Met) + tRNA(Met) <> Adenosine monophosphate + Pyrophosphate + L-Methionyl-tRNA + L-Methionyl-tRNA
5-Methyltetrahydropteroyltri-L-glutamic acid + L-Homocysteine <> Tetrahydropteroyltri-L-glutamic acid + L-Methionine
2-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-Ketoglutarate
Protein N6-(octanoyl)lysine + 2 Sulfur donor + 2 S-Adenosylmethionine + Protein N6-(octanoyl)lysine <> Protein N6-(lipoyl)lysine +2 L-Methionine +2 5'-Deoxyadenosine + Protein N6-(lipoyl)lysine
Octanoyl-[acp] + 2 Sulfur donor + 2 S-Adenosylmethionine <> Lipoyl-[acp] +2 L-Methionine +2 5'-Deoxyadenosine
L-Methionine + Hydrogen peroxide > L-methionine <i>S</i>-oxide + Water
Hydrogen ion + &alpha;-D-ribose-1-methylphosphonate-5-phosphate + S-Adenosylmethionine > &alpha;-D-ribose-1,2-cyclic-phosphate-5-phosphate + methane + 5'-Deoxyadenosine + L-Methionine
L-Methionine + Acetyl-CoA N-&alpha;-acetyl-L-methionine + Coenzyme A
<i>S</i>-sulfanyl-[acceptor] + Dethiobiotin + S-Adenosylmethionine > an unsulfurated sulfur acceptor + Biotin + 5'-Deoxyadenosine + L-Methionine + Hydrogen ion
a protein with N-terminal methionine + Water > L-Methionine + Peptides
Coproporphyrinogen III + S-Adenosylmethionine > Protoporphyrinogen IX + Carbon dioxide + L-Methionine + 5'-Deoxyadenosine
L-Homocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid > L-Methionine + tetrahydropteroyl tri-L-glutamate
L-Homocysteine + S-Adenosylmethionine Hydrogen ion + L-Methionine + S-Adenosylhomocysteine
S-methyl-L-methionine + L-Homocysteine Hydrogen ion + L-Methionine
5-Aminoimidazole ribonucleotide + S-Adenosylmethionine 4-Amino-2-methyl-5-phosphomethylpyrimidine + 5'-Deoxyadenosine + L-Methionine + Formic acid + carbon monoxide + Hydrogen ion
L-Methionine + a 2-oxo carboxylate 2-Oxo-4-methylthiobutanoic acid + a standard &alpha; amino acid
S-Adenosylmethionine + Ribonuc-tri-P-reductases-inactive <> 5'-Deoxyadenosine + L-Methionine + Ribonuc-tri-P-reductases-active
L-Tyrosine + S-Adenosylmethionine + a reduced electron acceptor > Dehydroglycine + p-Cresol + 5'-Deoxyadenosine + L-Methionine + an oxidized electron acceptor + Hydrogen ion
-->-->N-6-isopentyl adenosine-37 tRNA + S-Adenosylmethionine + <i>S</i>-sulfanyl-[acceptor] 2-methylthio-N-6-isopentyl adenosine-37 tRNA + S-Adenosylhomocysteine + L-Methionine + 5'-Deoxyadenosine + an unsulfurated sulfur acceptor + Hydrogen ion
6-Carboxy-5,6,7,8-tetrahydropterin + S-Adenosylmethionine + Hydrogen ion > 7-carboxy-7-deazaguanine + 5'-Deoxyadenosine + L-Methionine + Ammonia
gly-met + Water > Glycine + L-Methionine
methionine-alanine dipeptide + Water > L-Methionine + L-Alanine
5-methyltetrahydropteroyltri-L-glutamate + L-Homocysteine > tetrahydropteroyltri-L-glutamate + L-Methionine
L-Methionine + thioredoxin disulfide + Water > L-methionine (S)-S-oxide + thioredoxin
L-Methionine + thioredoxin disulfide + Water > L-Methionine (R)-S-oxide + thioredoxin
Adenosine triphosphate + L-Methionine + tRNA(Met) > Adenosine monophosphate + Pyrophosphate + L-methionyl-tRNA(Met)
L-Methionine + a 2-oxo acid > 2-Oxo-4-methylthiobutanoic acid + an L-amino acid
2 S-Adenosylmethionine <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine
2 S-Adenosylmethionine + Reduced acceptor <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine
L-Tyrosine + S-Adenosylmethionine + NADPH <> 2-iminoacetate + p-Cresol + 5'-Deoxyadenosine + L-Methionine + NADP + Hydrogen ion
Peptide-L-methionine + Thioredoxin disulfide + Water + L-Methionine <> Peptide-L-methionine (S)-S-oxide + Thioredoxin + L-methionine (S)-S-oxide
Dethiobiotin + 2 S-adenosyl-L-methionine + 2 Hydrogen ion + a sulfurated [sulfur carrier] > Biotin +2 L-Methionine +2 5'-Deoxyadenosine
Octanoyl-[acyl-carrier protein] + 2 a sulfur donor + 2 S-adenosyl-L-methionine > Lipoyl-ACP +2 L-Methionine + 5'-Deoxyadenosine
Protein N6-(octanoyl)lysine + 2 a sulfur donor + 2 S-adenosyl-L-methionine > Protein N6-(lipoyl)lysine +2 L-Methionine +2 5'-Deoxyadenosine
Protein N6-(octanoyl)lysine + 2 Reduced ferredoxin + 2 a sulfurated [sulfur carrier]? + 2 S-adenosyl-L-methionine >2 L-Methionine +2 5'-Deoxyadenosine + Oxidized ferredoxin + Protein N6-(lipoyl)lysine + an unsulfurated [sulfur carrier]
5-Methyltetrahydrofolic acid + Homocysteine + 5-Methyltetrahydrofolic acid + Homocysteine > Tetrahydrofolic acid + L-Methionine + Tetrahydrofolic acid
Homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate + Homocysteine > L-Methionine + tetrahydropteroyltri-L-glutamate
L-Methionine + Adenosine triphosphate + Hydrogen ion + tRNA(Met) > Adenosine monophosphate + Pyrophosphate + L-methionyl-tRNA(Met)
Homocysteine + N5-methyl--tetrahydropteroyl tri-L-glutamate + Homocysteine > tetrahydropteroyltri-L-glutamate + L-Methionine
L-Methionine + Water + Adenosine triphosphate > Phosphate + Pyrophosphate
L-Methionine + Water + Adenosine triphosphate > Phosphate + Pyrophosphate + S-adenosyl-L-methionine
S-adenosyl-L-methionine + Coproporphyrinogen III > 5'-Deoxyadenosine + L-Methionine + Carbon dioxide + Protoporphyrinogen IX
L-Tyrosine + NADPH + S-adenosyl-L-methionine + L-Tyrosine + NADPH > Hydrogen ion + NADP + L-Methionine + 5'-Deoxyadenosine + p-Cresol + 2-iminoacetate
7-aminomethyl-7-deazaguanosine34 in tRNA + S-adenosyl-L-methionine > Hydrogen ion + L-Methionine + Adenine + epoxyqueuosine
L-Methionine + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Methionine + ADP
L-Methionine + Adenosine triphosphate + Water > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Methionine + ADP
L-Methionine + Adenosine triphosphate + Water > Adenosine diphosphate + Pyrophosphate + Hydrogen ion + L-Methionine + ADP
L-Methionine + Adenosine triphosphate + Water > Adenosine diphosphate + Pyrophosphate + Hydrogen ion + L-Methionine + ADP
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-004i-0920000000-945c85aa7c9f5eb2dfbbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0910000000-b837ee0f4413856560f1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00b9-7910000000-5a1558fbb2f5e86edc9bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-1900000000-1a97567ce4f25c4e8263View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-0910000000-1b0477118cb20549bf4dView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-1900000000-b991859b2c5bed6592a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-08fr-9000000000-66855ace60e59837f131View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-08fr-9000000000-56a567791c824c6a9da6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0fe0-0900000000-d680295f21b2e2b40366View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-062d3540db4db22da836View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-84467513e2c9ec1a6851View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-88dc2bebb198eea550efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0920000000-b444ad79abeb16acde43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6e24a8df417e5f3db58cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-c60ef880eb9a816a274bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a7b7d1a3481c0c691a5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-9156f088f4cc9eafa892View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9200000000-f78ba2aab8d5a0e0b135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9000000000-e7b819fd2d0ac3862860View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-c3557cb41fd6fe268819View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-6900000000-6bf5af2d1c561013948aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-08fr-9000000000-63c9b1c138f9a27490e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-9000000000-e133c47b0efe4992589fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-dee78b4f34f8732fedb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0udi-0900000000-d3f03ff5e8eacc8b6c8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-e0dd5ff44b7962f6a2d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
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  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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. Pubmed: 19212411
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  • 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
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Synthesis Reference: Boy, Matthias; Klein, Daniela; Schroeder, Hartwig. Method for the production and recovery of methionine. PCT Int. Appl. (2005), 34 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID16811
HMDB IDHMDB00696
Pubchem Compound ID6137
Kegg IDC00073
ChemSpider ID5907
WikipediaMET
BioCyc IDMET
EcoCyc IDMET
Ligand ExpoMET_LFZW

Enzymes

General function:
Involved in nucleotide binding
Specific function:
Is required not only for elongation of protein synthesis but also for the initiation of all mRNA translation through initiator tRNA(fMet) aminoacylation
Gene Name:
metG
Locus Tag:
PA3482
Molecular weight:
74.9 kDa
Reactions
ATP + L-methionine + tRNA(Met) = AMP + diphosphate + L-methionyl-tRNA(Met).
General function:
Involved in transferase activity
Specific function:
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate
Gene Name:
tyrB
Locus Tag:
PA3139
Molecular weight:
43.3 kDa
Reactions
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate.
General function:
Involved in oxidoreductase activity, acting on a sulfur group of donors, disulfide as acceptor
Specific function:
Could have an important function as a repair enzyme for proteins that have been inactivated by oxidation. Catalyzes the reversible oxidation-reduction of methionine sulfoxide in proteins to methionine
Gene Name:
msrA
Locus Tag:
PA5018
Molecular weight:
23.5 kDa
Reactions
Peptide-L-methionine + thioredoxin disulfide + H(2)O = peptide-L-methionine (S)-S-oxide + thioredoxin.
L-methionine + thioredoxin disulfide + H(2)O = L-methionine (S)-S-oxide + thioredoxin.
General function:
Involved in peptide-methionine-(S)-S-oxide reductase activity
Specific function:
Peptide-L-methionine + thioredoxin disulfide + H(2)O = peptide-L-methionine (R)-S-oxide + thioredoxin
Gene Name:
msrB
Locus Tag:
PA2827
Molecular weight:
14.8 kDa
Reactions
Peptide-L-methionine + thioredoxin disulfide + H(2)O = peptide-L-methionine (R)-S-oxide + thioredoxin.
General function:
Involved in methionine adenosyltransferase activity
Specific function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP. The overall synthetic reaction is composed of two sequential steps, AdoMet formation and the subsequent tripolyphosphate hydrolysis which occurs prior to release of AdoMet from the enzyme. Is essential for growth
Gene Name:
metK
Locus Tag:
PA0546
Molecular weight:
42.7 kDa
Reactions
ATP + L-methionine + H(2)O = phosphate + diphosphate + S-adenosyl-L-methionine.
General function:
Involved in [formate-C-acetyltransferase]-activating enzyme activity
Specific function:
Activation of anaerobic ribonucleoside-triphosphate reductase under anaerobic conditions by generation of an organic free radical, using S-adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
Gene Name:
nrdG
Locus Tag:
PA1919
Molecular weight:
25.7 kDa
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of dethiobiotin (DTB) to biotin by the insertion of a sulfur atom into dethiobiotin via a radical- based mechanism
Gene Name:
bioB
Locus Tag:
PA0500
Molecular weight:
39.1 kDa
Reactions
Dethiobiotin + sulfur + 2 S-adenosyl-L-methionine = biotin + 2 L-methionine + 2 5'-deoxyadenosine.
General function:
Involved in methionine synthase activity
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
Gene Name:
metH
Locus Tag:
PA1843
Molecular weight:
135.1 kDa
Reactions
5-methyltetrahydrofolate + L-homocysteine = tetrahydrofolate + L-methionine.
General function:
Involved in 5-methyltetrahydropteroyltriglutamate-homocysteine S-methyltransferase activity
Specific function:
Catalyzes the transfer of a methyl group from 5- methyltetrahydrofolate to homocysteine resulting in methionine formation
Gene Name:
metE
Locus Tag:
PA1927
Molecular weight:
86.2 kDa
Reactions
5-methyltetrahydropteroyltri-L-glutamate + L-homocysteine = tetrahydropteroyltri-L-glutamate + L-methionine.
General function:
Involved in coproporphyrinogen oxidase activity
Specific function:
Anaerobic transformation of coproporphyrinogen-III into protoporphyrinogen-IX
Gene Name:
hemN
Locus Tag:
PA1546
Molecular weight:
52.5 kDa
Reactions
Coproporphyrinogen-III + 2 S-adenosyl-L-methionine = protoporphyrinogen-IX + 2 CO(2) + 2 L-methionine + 2 5'-deoxyadenosine.
General function:
Involved in coproporphyrinogen oxidase activity
Specific function:
Not Available
Gene Name:
yggW
Locus Tag:
PA0386
Molecular weight:
42.5 kDa
General function:
Involved in catalytic activity
Specific function:
Catalyzes the radical-mediated insertion of two sulfur atoms into the C-6 and C-8 positions of the octanoyl moiety bound to the lipoyl domains of lipoate-dependent enzymes, thereby converting the octanoylated domains into lipoylated derivatives. Free octanoate is not a substrate for lipA
Gene Name:
lipA
Locus Tag:
PA2862
Molecular weight:
32.7 kDa
Reactions
Protein N(6)-(octanoyl)lysine + 2 sulfur + 2 S-adenosyl-L-methionine = protein N(6)-(lipoyl)lysine + 2 L-methionine + 2 5'-deoxyadenosine.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the rearrangement of 1-deoxy-D-xylulose 5- phosphate (DXP) to produce the thiazole phosphate moiety of thiamine. Sulfur is provided by the thiocarboxylate moiety of the carrier protein ThiS. In vitro, sulfur can be provided by H(2)S
Gene Name:
thiG
Locus Tag:
PA0381
Molecular weight:
28.2 kDa
Reactions
1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS] = 2-((2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + [sulfur-carrier protein ThiS] + 2 H(2)O.
General function:
Involved in thiamine biosynthetic process
Specific function:
Catalyzes the synthesis of the hydroxymethylpyrimidine phosphate (HMP-P) moiety of thiamine from aminoimidazole ribotide (AIR) in a radical S-adenosyl-L-methionine (SAM)-dependent reaction
Gene Name:
thiC
Locus Tag:
PA4973
Molecular weight:
69.8 kDa
Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole + S-adenosyl-L-methionine = 4-amino-2-methyl-5-phosphomethylpyrimidine + 5'-deoxyadenosine + L-methionine + formate + CO.
General function:
Involved in electron carrier activity
Specific function:
Participates in various redox reactions through the reversible oxidation of its active center dithiol to a disulfide and catalyzes dithiol-disulfide exchange reactions
Gene Name:
trxA
Locus Tag:
PA5240
Molecular weight:
11.9 kDa
General function:
Not Available
Specific function:
Not Available
Gene Name:
yncA
Locus Tag:
PA4866
Molecular weight:
18.7 kDa
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Transfers and isomerizes the ribose moiety from AdoMet to the 7-aminomethyl group of 7-deazaguanine (preQ1-tRNA) to give epoxyqueuosine (oQ-tRNA)
Gene Name:
queA
Locus Tag:
PA3824
Molecular weight:
38.2 kDa
Reactions
S-adenosylmethionine + 7-aminomethyl-7-deazaguanosine = methionine + adenine + epoxyqueuosine.
General function:
Involved in 4 iron, 4 sulfur cluster binding
Specific function:
Specifically methylates position 2 of adenine 2503 in 23S rRNA
Gene Name:
rlmN
Locus Tag:
PA3806
Molecular weight:
41.7 kDa
Reactions
2 S-adenosyl-L-methionine + adenine(2503) in 23S rRNA = S-adenosyl-L-homocysteine + L-methionine + 5'-deoxyadenosine + 2-methyladenine(2503) in 23S rRNA.
General function:
tRNA methylthiolation
Specific function:
Catalyzes the methylthiolation of N6-(dimethylallyl)adenosine (i(6)A), leading to the formation of 2-methylthio-N6-(dimethylallyl)adenosine (ms(2)i(6)A) at position 37 in tRNAs that read codons beginning with uridine.
Gene Name:
miaB
Locus Tag:
PA3980
Molecular weight:
50 kDa
Reactions
N(6)-dimethylallyladenine(37) in tRNA + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 2-methylthio-N(6)-dimethylallyladenine(37) in tRNA + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine
General function:
RNA modification
Specific function:
Catalyzes the methylthiolation of the residue Asp-89 of ribosomal protein S12.
Gene Name:
rimO
Locus Tag:
PA0916
Molecular weight:
49 kDa
Reactions
L-aspartate-[ribosomal protein S12] + sulfur-(sulfur carrier) + 2 S-adenosyl-L-methionine = 3-methylthio-L-aspartate-[ribosomal protein S12] + S-adenosyl-L-homocysteine + (sulfur carrier) + L-methionine + 5'-deoxyadenosine

Transporters

General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Locus Tag:
PA5152
Molecular weight:
28.4 kDa