1.0 2011-09-21 00:22:14 UTC 2019-11-26 03:21:06 UTC FDB022949 Homocysteine thiolactone Elevated level of the nonprotein amino acid homocysteine (Hcy) is a risk factor for cardiovascular diseases, neurodegenerative diseases, and neural tube defects. Metabolic conversion of Hcy to a chemically reactive metabolite, Hcy-thiolactone, catalyzed by methionyl-tRNA synthetase is the first step in a pathway that contributes to Hcy toxicity in humans. (PMID 16702349) The only known source of Hcy in the human body is dietary protein methionine; subsequent examinations of individual dietary amino acids have led to the conclusion that methionine, ingested in excess, is the most toxic amino acid. (Harper AE, Benevenga NJ, Wohlheuter RM. Effects of ingestion of disproportionate amounts of amino acids. Physiol Rev. 1970;50: 428 - 58; Benevenga NJ, Steele RD. Adverse effects of excessive consumption of amino acids. Annu Rev Nutr. 1984; 4:157-81) Animals fed high-protein or high-methionine diets for 2 years developed hyperhomocysteinemia and evidence of vascular disease (Fau D, Preret J, Hadjiisky P. Effects of ingestion of high protein or excess methionine diets by rats for two years. J Nutr. 1988; 118:128-33) [HMDB] ( -)-3-Amino-2-thiolanon ( -)-3-Aminotetrahydro-2-thiophenon (+-)-3-Aminodihydro-2(3H)-thiophenone 3-Aminodihydro-2(3H)-thiophenone DL-3-Aminotetrahydro-2-thiophenone DL-Homocysteine thiolactone L-Homocysteine thiolactone C4H7NOS 117.169 117.024834541 3-aminothiolan-2-one DL-homocysteine thiolactone 3622-59-1 NC1CCSC1=O InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2 KIWQWJKWBHZMDT-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Alpha amino acids and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic heteromonocyclic compounds Carbonyl compounds Carbothioic S-lactones Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds Thioesters Thiolactones Thiolanes Aliphatic heteromonocyclic compound Alpha-amino acid or derivatives Amine Carbonyl group Carbothioic s-lactone Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Thiocarboxylic acid ester Thiocarboxylic acid or derivatives Thiolactone Thiolane Solid logp -0.51 ALOGPS logs -0.30 ALOGPS solubility 5.93e+01 g/l ALOGPS logp -0.25 ChemAxon pka_strongest_basic 7.83 ChemAxon iupac 3-aminothiolan-2-one ChemAxon average_mass 117.169 ChemAxon mono_mass 117.024834541 ChemAxon smiles NC1CCSC1=O ChemAxon formula C4H7NOS ChemAxon inchi InChI=1S/C4H7NOS/c5-3-1-2-7-4(3)6/h3H,1-2,5H2 ChemAxon inchikey KIWQWJKWBHZMDT-UHFFFAOYSA-N ChemAxon polar_surface_area 43.09 ChemAxon refractivity 29.76 ChemAxon polarizability 11.43 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 21547 Specdb::CMs 130956 Specdb::CMs 138690 Specdb::MsIr 1725 Specdb::MsIr 1726 Specdb::MsIr 1727 Specdb::MsMs 313888 Specdb::MsMs 313889 Specdb::MsMs 313890 Specdb::MsMs 359479 Specdb::MsMs 359480 Specdb::MsMs 359481 Specdb::MsMs 2401226 Specdb::MsMs 2401227 Specdb::MsMs 2401228 Specdb::MsMs 2538365 Specdb::MsMs 2538366 Specdb::MsMs 2538367 Specdb::NmrOneD 116018 Specdb::NmrOneD 116019 Specdb::NmrOneD 116020 Specdb::NmrOneD 116021 Specdb::NmrOneD 116022 Specdb::NmrOneD 116023 Specdb::NmrOneD 116024 Specdb::NmrOneD 116025 Specdb::NmrOneD 116026 Specdb::NmrOneD 116027 Specdb::NmrOneD 116028 Specdb::NmrOneD 116029 Specdb::NmrOneD 116030 Specdb::NmrOneD 116031 Specdb::NmrOneD 116032 Specdb::NmrOneD 116033 Specdb::NmrOneD 116034 Specdb::NmrOneD 116035 Specdb::NmrOneD 116036 Specdb::NmrOneD 116037 HMDB02287 #<Reference:0x000055ce30740f28> #<Reference:0x000055ce30740d70> #<Reference:0x000055ce30740bb8> #<Reference:0x000055ce30740a00> #<Reference:0x000055ce30740820> #<Reference:0x000055ce30740640> 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 Milk (Cow) Type 2 specific 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