Methionine

Methionine
	; Skeletal formula of the canonical form of methionine
Ball-and-stick model	Space-filling model
Names
	IUPAC name Methionine
	Other names 2-amino-4-(methylthio)butanoic acid
Identifiers
CAS Number	L: 63-68-3 ; D/L: 59-51-8 ; D: 348-67-4 ;
3D model (JSmol)	L: Interactive image; L Zwitterion: Interactive image;
Abbreviations	Met, M
ChEBI	L: CHEBI:16643 ; D/L: CHEBI:16811 ; D: CHEBI:16867 ;
ChEMBL	L: ChEMBL42336 ;
ChemSpider	L: 5907 ; D/L: 853 ; D: 76512 ;
DrugBank	L: DB00134 ;
ECHA InfoCard	100.000.393
EC Number	L: 200-432-1;
KEGG	L: C00073 ;
PubChem CID	L: 6137; D/L: 876; D: 84815;
UNII	L: AE28F7PNPL ; D/L: 73JWT2K6T3 ; D: 868496F25R ;
CompTox Dashboard (EPA)	L: DTXSID9020821 ;
	InChI InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1 Key: FFEARJCKVFRZRR-BYPYZUCNSA-N ; D/L: Key: FFEARJCKVFRZRR-UHFFFAOYSA-N; D: Key: FFEARJCKVFRZRR-SCSAIBSYSA-N;
	SMILES L: CSCC[C@H](N)C(=O)O; L Zwitterion: CSCC[C@H]([NH3+])C(=O)[O-];
Properties
Chemical formula	C5H11NO2S
Molar mass	149.21 g·mol−1
Appearance	White crystalline powder
Density	1.340 g/cm3
Melting point	281 °C (538 °F; 554 K) decomposes
Solubility in water	Soluble
Acidity (pKa)	2.28 (carboxyl), 9.21 (amino)
Pharmacology
ATC code	V03AB26 (WHO) QA05BA90 (WHO), QG04BA90 (WHO)
Supplementary data page
	Methionine (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Methionine (symbol Met or M) (/mɪˈθaɪəniːn/) is an essential amino acid in humans.

As the precursor of other non-essential amino acids such as cysteine and taurine, versatile compounds such as SAM-e, and the important antioxidant glutathione, methionine plays a critical role in the metabolism and health of many species, including humans. Methionine is also involved in angiogenesis and various processes related to DNA transcription, epigenetic expression, and gene regulation.

Methionine was first isolated in 1921 by John Howard Mueller. It is encoded by the codon AUG.

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