L-Homocystine (Lhcystin)

Human Metabolome Database (HMDB): Homocystine is the oxidized form of homocysteine. Homocystine is a dipeptide consisting of two homocysteine molecules joined by a disulfide bond. Homocysteine is a sulfur-containing amino acid that arises during methionine metabolism. Homocystine occurs only transiently before being reduced to homocysteine and converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfides account for >98% of total homocysteine in plasma from healthy individuals (PMID 11592966). Homocystine has been shown to stereospecifically induce endothelial nitric oxide synthase-dependent lipid peroxidation in endothelial cells, thereby inducing a vascular cell type-specific oxidative stress. This vascular stress is associated with atherothrombotic cardiovascular disease (PMID: 14980706). High levels of homocysteine (and homocysteine) can be found in individuals suffering from homocystinura due to cystathionine synthase deficiency (PMID: 4685596)

Charged formula:

C8H16N2O4S2

Charge:

0

InChIKey:

ZTVZLYBCZNMWCF-ZBHICJROSA-N

SMILES:

[H]OC(=O)C([H])(N([H])[H])C([H])([H])C([H])([H])SSC([H])([H])C([H])([H])[C@@]([H])(C(=O)O[H])N([H])[H]

External links: hmdb.cakegg.jpebi.ac.uk

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