General Information of Drug (ID: DR1043)
Drug Name
Methionine
Synonyms
Acimethin; Cymethion; L-(-)-Methionine; L-Homocysteine, S-methyl-; L-Methionin; L-Methioninum; L-methionine; Liquimeth; METHIONINE, L-; Methilanin; Methionine (VAN); Methioninum; Methioninum [INN-Latin]; Metionina [DCIT]; Neo-methidin; Poly-L-methionine; Polymethionine; S-Methionine; methionine; metionina; (2S)-2-amino-4-(methylsulfanyl)butanoic acid; (L)-Methionine; (S)-2-Amino-4-(methylthio)butanoic acid; (S)-methionine; 63-68-3; L-alpha-Amino-gamma-methylmercaptobutyric acid; h-Met-h; h-Met-oh
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 149.21 Topological Polar Surface Area 88.6
Heavy Atom Count 9 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
6137
PubChem SID
3373 ; 584216 ; 584218 ; 584908 ; 820501 ; 822833 ; 829149 ; 829365 ; 829494 ; 830509 ; 831183 ; 831935 ; 836933 ; 838795 ; 840774 ; 841586 ; 6436231 ; 7847087 ; 7888883 ; 8144963 ; 8153848 ; 10317509 ; 10531327 ; 11528400 ; 11538848 ; 14710667 ; 14772273 ; 24424513 ; 24883259 ; 24896818 ; 24897258 ; 24897343 ; 26746545 ; 26750484 ; 29216310 ; 29225140 ; 46392872 ; 46393022 ; 46393499 ; 46505750 ; 49747977 ; 53790591 ; 56269966 ; 56311398 ; 57244615 ; 57323215 ; 57580977 ; 57651979 ; 57654418 ; 74993309
ChEBI ID
CHEBI:16643
CAS Number
63-68-3
TTD Drug ID
D0PO8E
Formula
C5H11NO2S
Canonical SMILES
CSCCC(C(=O)O)N
InChI
1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
InChIKey
FFEARJCKVFRZRR-BYPYZUCNSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Methionine sulfoxide DM005471
158980
Oxidation - S-oxidation 1 [2]
N-Acetyl-methionine DM005473
6180
Conjugation - N-acetylation 1 [2]
N-Acetyl-methionine sulfoxide DM005472
193368
Oxidation - S-oxidation 2 [2]
N-Acetyl-methionine sulfoxide DM005472
193368
Conjugation - N-acetylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005824 Methionine Methionine sulfoxide Oxidation - S-oxidation FMO3 [2]
MR005826 Methionine N-Acetyl-methionine Conjugation - N-acetylation Unclear [2]
MR005825 Methionine sulfoxide N-Acetyl-methionine sulfoxide Conjugation - N-acetylation Unclear [2]
MR005827 N-Acetyl-methionine N-Acetyl-methionine sulfoxide Oxidation - S-oxidation FMO3 [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[2]
Homoserine-O-transsuccinylase (metAA) DME1461 Salmonella enterica
METAA_THEMA
2.3.1.46
[3]
Methionine adenosyltransferase II beta (MAT2B) DME0183 Homo sapiens
MAT2B_HUMAN
2.5.1.6
[4]
Methionine-R-sulfoxide reductase B1 (MSRB1) DME0184 Homo sapiens
MSRB1_HUMAN
1.8.4.12
[5]
Methionine-R-sulfoxide reductase B2 (MSRB2) DME0185 Homo sapiens
MSRB2_HUMAN
1.8.4.12
[6]
Methionine-tRNA ligase cytoplasmic (MARS) DME0186 Homo sapiens
SYMC_HUMAN
6.1.1.10
[7]
Methionine-tRNA ligase mitochondrial (MARS2) DME0187 Homo sapiens
SYMM_HUMAN
6.1.1.10
[4]
Peptide methionine sulfoxide reductase (MSRA) DME0188 Homo sapiens
MSRA_HUMAN
1.8.4.11
[8]
S-adenosylmethionine synthase 1 (MAT1A) DME0189 Homo sapiens
METK1_HUMAN
2.5.1.6
[9]
S-adenosylmethionine synthase 2 (MAT2A) DME0190 Homo sapiens
METK2_HUMAN
2.5.1.6
[9]
⏷ Show the Full List of 10  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Methionine-tRNA ligase cytoplasmic (MARS) DME0186 Km = 0.018 microM
SYMC_HUMAN
[10]
Methionine adenosyltransferase II beta (MAT2B) DME0183 Km = 0.022 microM
MAT2B_HUMAN
[11]
References
1 The IUPHAR/BPS Guide to PHARMACOLOGY in 2020: extending immunopharmacology content and introducing the IUPHAR/MMV Guide to MALARIA PHARMACOLOGY. Nucleic Acids Res. 2020 Jan 8;48(D1):D1006-D1021. (Ligand id: 4814).
2 In vivo metabolism of L-methionine in mice: evidence for stereoselective formation of methionine-d-sulfoxide and quantitation of other major metabolites
3 Regulation of the methionine feedback-sensitive enzyme in mutants of Salmonella typhimurium. J Bacteriol. 1972 Jan;109(1):8-11.
4 How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
5 Catalytic advantages provided by selenocysteine in methionine-S-sulfoxide reductases. Biochemistry. 2006 Nov 21;45(46):13697-704.
6 The X-ray structure of the N-terminal domain of PILB from Neisseria meningitidis reveals a thioredoxin-fold. J Mol Biol. 2006 Apr 28;358(2):443-54.
7 Mutations in methylenetetrahydrofolate reductase or cystathionine beta-synthase gene, or a high-methionine diet, increase homocysteine thiolactone levels in humans and mice. FASEB J. 2007 Jun;21(8):1707-13.
8 Characterization of the amino acids involved in substrate specificity of methionine sulfoxide reductase A. J Biol Chem. 2007 Jul 13;282(28):20484-91.
9 Role of methionine adenosyltransferase 2A and S-adenosylmethionine in mitogen-induced growth of human colon cancer cells. Gastroenterology. 2007 Jul;133(1):207-18.
10 Characterization of the human mitochondrial methionyl-tRNA synthetase. Biochemistry. 2004 Aug 3;43(30):9743-54.
11 Cloning, expression, and functional characterization of the beta regulatory subunit of human methionine adenosyltransferase (MAT II). J Biol Chem. 2000 Jan 28;275(4):2359-66.

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