1.0 2016-09-30 22:35:50 UTC 2020-05-21 16:28:33 UTC BMDB0000742 BMDB00742 Homocysteine Homocysteine, also known as Hcy or homo-cys, 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). Homocysteine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Homocysteine exists in all living species, ranging from bacteria to humans. Homocysteine is a potentially toxic compound. Hcy L-2-Amino-4-mercaptobutyric acid L-2-Amino-4-mercaptobutyrate 2-Amino-4-mercaptobutyric acid Homocysteine, L isomer L-Isomer homocysteine 2 Amino 4 mercaptobutyric acid Homocysteine, L-isomer (S)-2-Amino-4-mercapto-butanoate (S)-2-Amino-4-mercapto-butanoic acid (S)-2-Amino-4-mercaptobutanoic acid (S)-Homocysteine 2-Amino-4-mercapto-DL-butyrate 2-Amino-4-mercapto-DL-butyric acid 2-Amino-4-mercapto-L-butyric acid 2-Amino-4-mercapto-butanoate 2-Amino-4-mercapto-butanoic acid 2-Amino-4-mercapto-butyric acid 2-Amino-4-sulfanylbutanoate 2-Amino-4-sulfanylbutanoic acid D,L-Homocysteine DL-2-Amino-4-mercapto-butyric acid DL-2-Amino-4-mercaptobutyric acid DL-Homocysteine Homo-cys L-2-Amino-4-mercapto-butyric acid L-Homocysteine 2-Amino-4-mercapto-butyrate Homocysteine C4H9NO2S 135.185 135.035399227 (2S)-2-amino-4-sulfanylbutanoic acid L-homocysteine 6027-13-0 N[C@@H](CCS)C(O)=O InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1 FFFHZYDWPBMWHY-VKHMYHEASA-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. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues L-alpha-amino acids Alkylthiols Amino acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Thia fatty acids Aliphatic acyclic compound Alkylthiol Amine Amino acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Thia fatty acid Aliphatic acyclic compounds Other amino acids homocysteine serine family amino acid Solid melting_point 232 - 233 °C water_solubility 148 mg/mL logp -2.29 ALOGPS logs -0.96 ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 2.46 ChemAxon pka_strongest_basic 9.41 ChemAxon iupac (2S)-2-amino-4-sulfanylbutanoic acid ChemAxon average_mass 135.185 ChemAxon mono_mass 135.035399227 ChemAxon smiles N[C@@H](CCS)C(O)=O ChemAxon formula C4H9NO2S ChemAxon inchi InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1 ChemAxon inchikey FFFHZYDWPBMWHY-VKHMYHEASA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 32.94 ChemAxon polarizability 13.54 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Betaine Metabolism SMP0087182 Glycine and Serine Metabolism SMP0087245 Homocysteine Degradation SMP0087201 Methionine Metabolism SMP0087249 Specdb::MsIr 814 Specdb::MsIr 815 Specdb::MsIr 816 Specdb::NmrTwoD 2041 Specdb::CMs 3134 Specdb::CMs 30370 Specdb::CMs 147699 Specdb::CMs 1074587 Specdb::CMs 1074589 Specdb::CMs 1074590 Specdb::CMs 1074592 Specdb::CMs 1074594 Specdb::CMs 1074595 Specdb::NmrOneD 5208 Specdb::NmrOneD 5209 Specdb::NmrOneD 5210 Specdb::NmrOneD 5211 Specdb::NmrOneD 145170 Specdb::NmrOneD 145171 Specdb::NmrOneD 145172 Specdb::NmrOneD 145173 Specdb::NmrOneD 145174 Specdb::NmrOneD 145175 Specdb::NmrOneD 145176 Specdb::NmrOneD 145177 Specdb::NmrOneD 145178 Specdb::NmrOneD 145179 Specdb::NmrOneD 145180 Specdb::NmrOneD 145181 Specdb::NmrOneD 145182 Specdb::NmrOneD 145183 Specdb::NmrOneD 145184 Specdb::NmrOneD 145185 Specdb::NmrOneD 145186 Specdb::NmrOneD 145187 Specdb::NmrOneD 145188 Specdb::NmrOneD 145189 Specdb::MsMs 25745 Specdb::MsMs 25746 Specdb::MsMs 25747 Specdb::MsMs 32303 Specdb::MsMs 32304 Specdb::MsMs 32305 Specdb::MsMs 447603 Specdb::MsMs 447753 Specdb::MsMs 447754 Specdb::MsMs 2255806 Specdb::MsMs 2262739 Specdb::MsMs 2262740 Specdb::MsMs 2262741 Specdb::MsMs 3080268 Specdb::MsMs 3080269 Specdb::MsMs 3080270 Adipose Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk By UPLC-Q-TOF Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. 29565828 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Pancreas Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Skeletal Muscle Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00155 FDB001491 82666 DB04422 17588 91552 C00001365 HOMO-CYS Homocysteine 3256 Karrenbauer, Michael; Kleemann, Axel; Luessling, Theodor; Schaefer, Fritz. D,L-Homocysteine (I). Ger. (1984), 4 pp. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. 29565828 BMDBP00414 Methionine synthase Q4JIJ3 MTR Enzyme BMDBP00837 Adenosylhomocysteinase A5PKK6 AHCYL1 Enzyme BMDBP00838 Adenosylhomocysteinase 3 A6QLP2 AHCYL2 Enzyme BMDBP01057 Betaine--homocysteine S-methyltransferase 1 Q5I597 BHMT Enzyme BMDBP01293 Adenosylhomocysteinase Q3MHL4 AHCY Enzyme BMDBP03019 Cystathionine beta-synthase F1MEW4 CBS Enzyme