Ophthalmic acid

Ophthalmic acid^[1]
Names
	IUPAC name (N-(L-γ-Glutamyl)-(2S)-2-aminobutyryl)glycine
Identifiers
CAS Number	495-27-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:84058 ;
ChemSpider	5381695 ;
MeSH	ophthalmic+acid
PubChem CID	7018721;
UNII	3A60475Q1Q ;
CompTox Dashboard (EPA)	DTXSID40895053 ;
	InChI InChI=1S/C11H19N3O6/c1-2-7(10(18)13-5-9(16)17)14-8(15)4-3-6(12)11(19)20/h6-7H,2-5,12H2,1H3,(H,13,18)(H,14,15)(H,16,17)(H,19,20)/t6-,7-/m0/s1 Key: JCMUOFQHZLPHQP-BQBZGAKWSA-N ;
	SMILES CC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O;
Properties
Chemical formula	C11H19N3O6
Molar mass	289.288 g·mol−1
Appearance	White crystals
Related compounds
Related alkanoic acids	N-Acetylaspartylglutamic acid; Glycylglycine; α-Aminobutyric acid;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ophthalmic acid (OPH), also known as ophthalmate (chemically L-γ-glutamyl-L-α-aminobutyrylglycine), is a tripeptide analog of glutathione. However, instead of the cysteine essential for many of glutathione's diverse functions, it contains L-2-aminobutyrate, a non-proteinogenic amino acid lacking the nucleophilic thiol group. Because of this, it has been widely, and incorrectly, considered an accidental byproduct of glutathione synthesis.

In 2024, an article published by the federation of European biochemistry societies compiled evidence to put forward the major hypothesis that OPH serves as a glutathione regulating tripeptide, affecting both cellular and organelle influx and efflux of GSH, as well as modulating GSH-dependent reactions and signaling.^[2]

^ Ophthalmic acid
^ Schomakers, Bauke V.; Jillings, Sonia L.; van Weeghel, Michel; Vaz, Frédéric M.; Salomons, Gajja S.; Janssens, Georges E.; Houtkooper, Riekelt H. (2024-01-20). "Ophthalmic acid is a glutathione regulating tripeptide". The FEBS Journal. doi:10.1111/febs.17061. ISSN 1742-464X.

[1] Ophthalmic acid

[:14-2] Schomakers, Bauke V.; Jillings, Sonia L.; van Weeghel, Michel; Vaz, Frédéric M.; Salomons, Gajja S.; Janssens, Georges E.; Houtkooper, Riekelt H. (2024-01-20). "Ophthalmic acid is a glutathione regulating tripeptide". The FEBS Journal. doi:10.1111/febs.17061. ISSN 1742-464X.

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[2]