1.0 2011-09-21 00:09:35 UTC 2015-10-09 22:30:37 UTC FDB022176 L-Homocystine 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] [S-(R*,R*)]-4,4'-dithiobis-2-amino-Butanoate [S-(R*,R*)]-4,4'-dithiobis-2-amino-Butanoic acid 4,4'-dithiobis-2-amino-L-Butyrate 4,4'-dithiobis-2-amino-L-Butyric acid 4,4'-Dithiobis(2-aminobutyric acid) L-Homocystine C8H16N2O4S2 268.354 268.05514839 2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid 2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid 626-72-2 NC(CCSSCC[C@H](N)C(O)=O)C(O)=O 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 ZTVZLYBCZNMWCF-ZBHICJROSA-N 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. L-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboxylic acids Dialkyldisulfides Dicarboxylic acids and derivatives Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Sulfenyl compounds Thia fatty acids Aliphatic acyclic compound Amine Amino acid Carbonyl group Carboxylic acid Dialkyldisulfide Dicarboxylic acid or derivatives Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Organic disulfide Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Sulfenyl compound Thia fatty acid Solid logp -4.15 ALOGPS logs -1.78 ALOGPS solubility 4.50e+00 g/l ALOGPS logp -5.3 ChemAxon pka_strongest_acidic 1.8 ChemAxon pka_strongest_basic 9.8 ChemAxon iupac 2-amino-4-{[(3S)-3-amino-3-carboxypropyl]disulfanyl}butanoic acid ChemAxon average_mass 268.354 ChemAxon mono_mass 268.05514839 ChemAxon smiles NC(CCSSCC[C@H](N)C(O)=O)C(O)=O ChemAxon formula C8H16N2O4S2 ChemAxon inchi 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 ChemAxon inchikey ZTVZLYBCZNMWCF-ZBHICJROSA-N ChemAxon polar_surface_area 126.64 ChemAxon refractivity 64.38 ChemAxon polarizability 26.92 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1418 Specdb::NmrOneD 1473 Specdb::NmrOneD 7342 Specdb::NmrOneD 7343 Specdb::NmrOneD 7344 Specdb::NmrOneD 7345 Specdb::NmrOneD 7346 Specdb::NmrOneD 7347 Specdb::NmrOneD 7348 Specdb::NmrOneD 7349 Specdb::NmrOneD 7350 Specdb::NmrOneD 7351 Specdb::NmrOneD 7352 Specdb::NmrOneD 7353 Specdb::NmrOneD 7354 Specdb::NmrOneD 7355 Specdb::NmrOneD 7356 Specdb::NmrOneD 7357 Specdb::NmrOneD 7358 Specdb::NmrOneD 7359 Specdb::NmrOneD 7360 Specdb::NmrOneD 7361 Specdb::NmrOneD 166619 Specdb::CMs 15651 Specdb::CMs 32144 Specdb::CMs 32145 Specdb::CMs 37691 Specdb::CMs 99590 Specdb::CMs 99591 Specdb::CMs 157558 Specdb::CMs 1072357 Specdb::CMs 1072359 Specdb::CMs 1072360 Specdb::CMs 1072362 Specdb::CMs 1072364 Specdb::CMs 1072366 Specdb::CMs 1072368 Specdb::CMs 1072370 Specdb::CMs 1072371 Specdb::CMs 1072373 Specdb::CMs 1072375 Specdb::CMs 1072377 Specdb::CMs 1072379 Specdb::CMs 1072380 Specdb::CMs 1072382 Specdb::CMs 1072384 Specdb::CMs 1072386 Specdb::CMs 1072387 Specdb::MsMs 936 Specdb::MsMs 937 Specdb::MsMs 938 Specdb::MsMs 300676 Specdb::MsMs 300677 Specdb::MsMs 300678 Specdb::MsMs 343000 Specdb::MsMs 343001 Specdb::MsMs 343002 Specdb::MsMs 2836749 Specdb::MsMs 2836750 Specdb::MsMs 2836751 Specdb::MsMs 2872817 Specdb::MsMs 2872818 Specdb::MsMs 2872819 HMDB00676 #<Reference:0x000055ac408bfeb0> #<Reference:0x000055ac408b7e18> #<Reference:0x000055ac408b7c60> #<Reference:0x000055ac408b7aa8> #<Reference:0x000055ac408b78a0> #<Reference:0x000055ac408b76e8> #<Reference:0x000055ac408b7508> #<Reference:0x000055ac408b7350> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823