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)^[3] (/mɪˈθaɪəniːn/)^[4] 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.^[5] It is encoded by the codon AUG. It was named by Satoru Odake in 1925, as an abbreviation of its structural description 2-amino-4-(methylthio)butanoic acid.^[6]

^ Dawson RM, Elliott DC, Elliott WH, Jones KM (1959). Data for Biochemical Research. Oxford: Clarendon Press.
^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-374. ISBN 0-8493-0462-8..
^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
^ "Methionine". Oxford University Press. Archived from the original on January 27, 2018.
^ Pappenheimer AM (1987). "A Biographical Memoir of John Howard Mueller" (PDF). Washington D.C.: National Academy of Sciences.
^ Odake, Satoru (1925). "On the Occurrence of a Sulphur-containing Amino acid in Yeast". Bulletin of the Agricultural Chemical Society of Japan. 1 (8): 87–89. doi:10.1271/bbb1924.1.87. ISSN 1881-1272.

[1] Dawson RM, Elliott DC, Elliott WH, Jones KM (1959). Data for Biochemical Research. Oxford: Clarendon Press.

[2] Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-374. ISBN 0-8493-0462-8..

[3] "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.

[4] "Methionine". Oxford University Press. Archived from the original on January 27, 2018.

[5] Pappenheimer AM (1987). "A Biographical Memoir of John Howard Mueller" (PDF). Washington D.C.: National Academy of Sciences.

[6] Odake, Satoru (1925). "On the Occurrence of a Sulphur-containing Amino acid in Yeast". Bulletin of the Agricultural Chemical Society of Japan. 1 (8): 87–89. doi:10.1271/bbb1924.1.87. ISSN 1881-1272.

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