Homocysteine

Homocysteine
Names
	IUPAC name 2-Amino-4-sulfanylbutanoic acid
Identifiers
CAS Number	454-29-5 (racemate) ; 6027-13-0 (L-isomer) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17230 ;
ChEMBL	ChEMBL310604 ;
ChemSpider	757 ;
ECHA InfoCard	100.006.567
EC Number	207-222-9;
KEGG	C05330 ;
PubChem CID	778;
UNII	S7IJP4A89K (racemate) ; 0LVT1QZ0BA (L-isomer) ;
	InChI InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7) Key: FFFHZYDWPBMWHY-UHFFFAOYSA-N ; InChI=1/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7) Key: FFFHZYDWPBMWHY-UHFFFAOYAS;
	SMILES C(CS)C(C(=O)O)N;
Properties
Chemical formula	C4H9NO2S
Molar mass	135.18 g/mol
Appearance	White crystalline powder
Melting point	234–235 °C (453–455 °F; 507–508 K) (decomposes)
Solubility in water	soluble
log P	-2.56
Acidity (pKa)	2.25
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
	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

Homocysteine (/ˌhoʊmoʊˈsɪstiːn/) or Hcy: is a non-proteinogenic α-amino acid. It is a homologue of the amino acid cysteine, differing by an additional methylene bridge (-CH₂-). It is biosynthesized from methionine by the removal of its terminal C^ε methyl group. In the body, homocysteine can be recycled into methionine or converted into cysteine with the aid of vitamin B6, B9, and B12.

High levels of homocysteine in the blood (hyperhomocysteinemia) is regarded as a marker of cardiovascular disease, likely working through atherogenesis, which can result in ischemic injury. Therefore, hyperhomocysteinemia is a possible risk factor for coronary artery disease. Coronary artery disease occurs when an atherosclerotic plaque blocks blood flow to the coronary arteries, which supply the heart with oxygenated blood.

Hyperhomocysteinemia has been correlated with the occurrence of blood clots, heart attacks, and strokes, although it is unclear whether hyperhomocysteinemia is an independent risk factor for these conditions. Hyperhomocysteinemia also has been associated with early-term spontaneous abortions and with neural tube defects.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.