FComEx: L-Homocystine (PC000420)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:37 UTC

Update date

2017-01-19 02:36:22 UTC

FoodComEx ID

PC000420

FoodDB Record

FDB022176

Chemical Information

Name

L-Homocystine

Description

Homocystine is the double-bonded form of homocysteine, but it occurs only transiently before being converted to the harmless cystathionine via a vitamin B6-dependent enzyme. Homocystine and homocysteine-cysteine mixed disulfide account for >98% of total homocysteine in plasma from healthy individuals. (PMID 11592966) Oxidation of low-density lipoprotein (LDL) is thought to be a major factor in the pathophysiology of atherosclerosis. Elevated plasma homocysteine is an accepted risk factor for atherosclerosis, and may act through LDL oxidation, although this is controversial. However, the major thiol in plasma is cysteine, which is present at concentrations approximately 10 times greater than homocysteine; therefore homocystine in plasma is insignificant, and consequently homocystine is unlikely to influence LDL oxidation in vivo. (PMID 14732479) Increasing evidence supports a role for an elevation of homocysteine in schizophrenia. It has been demonstrated that neural tube defects are related to a genetic defect in homocysteine metabolism. Sufficient intake of folic acid is believed to reduce this risk by enhancing methylation of homocysteine and its conversion to methionine, thereby compensating for this genetic defect. Plasma homocysteine levels are elevated when folate levels are in the lower half of the normal range. (PMID 16143442 ) [HMDB]

CAS Number

626-72-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
[S-(R,R)]-4,4'-dithiobis-2-amino-Butanoate	hmdb
[S-(R,R)]-4,4'-dithiobis-2-amino-Butanoic acid	hmdb
4,4'-dithiobis-2-amino-L-Butyrate	hmdb
4,4'-dithiobis-2-amino-L-Butyric acid	hmdb
4,4'-Dithiobis(2-aminobutyric acid)	hmdb
L-Homocystine	hmdb

Chemical Formula

C8H16N2O4S2

IUPAC name

2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid

InChI Identifier

InChI=1S/C8H16N2O4S2/c9-5(7(11)12)1-3-15-16-4-2-6(10)8(13)14/h5-6H,1-4,9-10H2,(H,11,12)(H,13,14)/t5-,6?/m0/s1

InChI Key

ZTVZLYBCZNMWCF-ZBHICJROSA-N

Isomeric SMILES

NC(CCSSCC[C@H](N)C(O)=O)C(O)=O

Average Molecular Weight

268.354

Monoisotopic Molecular Weight

268.05514839

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents