1.0 2016-09-30 22:27:36 UTC 2020-06-04 20:57:12 UTC BMDB0000265 BMDB00265 Liothyronine Liothyronine, also known as T3 or liotironina, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Liothyronine is a drug which is used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis. Liothyronine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Liothyronine exists in all living organisms, ranging from bacteria to humans. In cattle, liothyronine is involved in the metabolic pathway called thyroid hormone synthesis pathway. Liothyronine is a potentially toxic compound. 3,5,3'-Triiodo-L-thyronine 3,5,3'-Triiodothyronine 3,5,3'TRIIODOTHYRONINE 4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine L-3,5,3'-Triiodothyronine L-T3 Liothyroninum Liotironina O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine T3 Tertroxin Tresitope Triiodothyronine 3,3',5-Triiodo-L-thyronine Thyrolar 3,3',5-Triiodothyronine Cytomel T3 Thyroid hormone Thyroid hormone, T3 Liothyronine sodium 3,3',5'-Triiodo-L-thyronine 3,3',5'-Triiodothyronine 4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine Cyronine L-3,3',5-Triiodo-thyronine L-3,3',5-Triiodothyronine L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-alanine L-Liothyronine L-Triiodothyronine Liothyronin Triiodo-L-thyronine C15H12I3NO4 650.9735 650.790038137 (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid liothyronine 6893-02-3 N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1 AUYYCJSJGJYCDS-LBPRGKRZSA-N belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Phenylalanine and derivatives 1-hydroxy-2-unsubstituted benzenoids Amino acids Amphetamines and derivatives Aralkylamines Aryl iodides Carbonyl compounds Carboxylic acids Diarylethers Diphenylethers Hydrocarbon derivatives Iodobenzenes L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives O-iodophenols Organic oxides Organoiodides Organopnictogen compounds Phenol ethers Phenoxy compounds Phenylpropanoic acids 1-hydroxy-2-unsubstituted benzenoid 2-halophenol 2-iodophenol 3-phenylpropanoic-acid Alpha-amino acid Amine Amino acid Amphetamine or derivatives Aralkylamine Aromatic homomonocyclic compound Aryl halide Aryl iodide Benzenoid Carbonyl group Carboxylic acid Diaryl ether Diphenylether Ether Halobenzene Hydrocarbon derivative Iodobenzene L-alpha-amino acid Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic nitrogen compound Organic oxide Organic oxygen compound Organohalogen compound Organoiodide Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Phenol ether Phenoxy compound Phenylalanine or derivatives Primary aliphatic amine Primary amine Aromatic homomonocyclic compounds 2-halophenol Other amino acids iodophenol iodothyronine thyroxine Solid logp 0.82 ALOGPS logs -4.52 ALOGPS logp 2.8 ChemAxon pka_strongest_acidic 0.3 ChemAxon pka_strongest_basic 9.48 ChemAxon iupac (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid ChemAxon average_mass 650.9735 ChemAxon mono_mass 650.790038137 ChemAxon smiles N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O ChemAxon formula C15H12I3NO4 ChemAxon inchi InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1 ChemAxon inchikey AUYYCJSJGJYCDS-LBPRGKRZSA-N ChemAxon polar_surface_area 92.78 ChemAxon refractivity 113.43 ChemAxon polarizability 43.92 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Thyroid Hormone Synthesis SMP0087269 Specdb::NmrOneD 1301 Specdb::NmrTwoD 1247 Specdb::CMs 7084 Specdb::CMs 644585 Specdb::CMs 644586 Specdb::CMs 644587 Specdb::CMs 644588 Specdb::CMs 644589 Specdb::CMs 644590 Specdb::CMs 644591 Specdb::CMs 644592 Specdb::CMs 644593 Specdb::CMs 644594 Specdb::CMs 644595 Specdb::CMs 644596 Specdb::CMs 644597 Specdb::CMs 644598 Specdb::CMs 793811 Specdb::MsMs 460 Specdb::MsMs 461 Specdb::MsMs 462 Specdb::MsMs 3846 Specdb::MsMs 3847 Specdb::MsMs 3848 Specdb::MsMs 3849 Specdb::MsMs 3850 Specdb::MsMs 3851 Specdb::MsMs 3852 Specdb::MsMs 3853 Specdb::MsMs 3854 Specdb::MsMs 3855 Specdb::MsMs 251622 Specdb::MsMs 251623 Specdb::MsMs 251624 Specdb::MsMs 271563 Specdb::MsMs 271564 Specdb::MsMs 271565 Specdb::MsMs 438527 Specdb::MsMs 438528 Specdb::MsMs 438529 Specdb::MsMs 438530 Specdb::MsMs 438531 Specdb::MsMs 447095 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 Adrenal Gland 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 Epidermis 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 Milk 500 uM Slebodzinski AB, Nowak J, Gawecka H, Sechman A: Thyroid hormones and insulin in milk; a comparative study. Endocrinol Exp. 1986 Aug;20(2-3):247-55. 3530717 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 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 Testis 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 Thyroid Gland 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 C02465 DB00279 18258 5920 CPD-10813 Triiodothyronine Salamonczyk, Grzegorz M.; Oza, Vibha B.; Sih, Charles J. A concise synthesis of thyroxine (T4) and 3,5,3'-triiodo-L-thyronine (T3). Tetrahedron Letters (1997), 38(40), 6965-69 Slebodzinski AB, Nowak J, Gawecka H, Sechman A: Thyroid hormones and insulin in milk; a comparative study. Endocrinol Exp. 1986 Aug;20(2-3):247-55. 3530717 BMDBP00548 Thyroxine 5-deiodinase Q5I3B1 DIO3 Enzyme