1.0 2011-09-21 00:08:49 UTC 2018-05-28 18:31:24 UTC FDB022123 DL-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] 4,4'-Dithiobis 4,4'-Dithiobis(2-aminobutyrate) DL-Homocystine Homocystine C8H16N2O4S2 268.354 268.05514839 2-amino-4-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid homocystine 870-93-9 NC(CCSSCCC(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) ZTVZLYBCZNMWCF-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 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 Alpha-amino acid Amine Amino acid Carbonyl group Carboxylic acid Dialkyldisulfide Dicarboxylic acid or derivatives Fatty acid Fatty acyl Hydrocarbon derivative 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 homocystines 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-[(3-amino-3-carboxypropyl)disulfanyl]butanoic acid ChemAxon average_mass 268.354 ChemAxon mono_mass 268.05514839 ChemAxon smiles NC(CCSSCCC(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) ChemAxon inchikey ZTVZLYBCZNMWCF-UHFFFAOYSA-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 1372 Specdb::NmrOneD 1427 Specdb::NmrOneD 144470 Specdb::NmrOneD 144471 Specdb::NmrOneD 144472 Specdb::NmrOneD 144473 Specdb::NmrOneD 144474 Specdb::NmrOneD 144475 Specdb::NmrOneD 144476 Specdb::NmrOneD 144477 Specdb::NmrOneD 144478 Specdb::NmrOneD 144479 Specdb::NmrOneD 144480 Specdb::NmrOneD 144481 Specdb::NmrOneD 144482 Specdb::NmrOneD 144483 Specdb::NmrOneD 144484 Specdb::NmrOneD 144485 Specdb::NmrOneD 144486 Specdb::NmrOneD 144487 Specdb::NmrOneD 144488 Specdb::NmrOneD 144489 Specdb::MsMs 803 Specdb::MsMs 804 Specdb::MsMs 805 Specdb::MsMs 4218 Specdb::MsMs 4219 Specdb::MsMs 4220 Specdb::MsMs 4221 Specdb::MsMs 4222 Specdb::MsMs 312844 Specdb::MsMs 312845 Specdb::MsMs 312846 Specdb::MsMs 358195 Specdb::MsMs 358196 Specdb::MsMs 358197 Specdb::MsMs 437850 Specdb::MsMs 437851 Specdb::MsMs 437852 Specdb::MsMs 437853 Specdb::MsMs 437854 Specdb::MsMs 440078 Specdb::MsMs 2236222 Specdb::MsMs 2237175 Specdb::MsMs 2238287 Specdb::MsMs 2239275 Specdb::MsMs 2240436 Specdb::CMs 577 Specdb::CMs 21048 Specdb::CMs 30523 Specdb::CMs 37633 Specdb::CMs 163068 Specdb::CMs 1066894 Specdb::CMs 1066896 Specdb::CMs 1066897 Specdb::CMs 1066899 Specdb::CMs 1066901 Specdb::CMs 1066903 Specdb::CMs 1066905 Specdb::CMs 1066907 Specdb::CMs 1066908 Specdb::CMs 1066910 Specdb::CMs 1066912 Specdb::CMs 1066914 Specdb::CMs 1066916 HMDB00575 #<Reference:0x00007f08cc775c50> #<Reference:0x00007f08cc775a48> #<Reference:0x00007f08cc775890> #<Reference:0x00007f08cc775688> #<Reference:0x00007f08cc775430> 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