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Record Information
Version	2.0
Creation Date	2015-09-08 17:48:32 -0600
Update Date	2015-09-08 17:48:32 -0600
Secondary Accession Numbers	ECMDB24025
Identification
Name:	Thyroxine
Description
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9d3ea254> Close
Synonyms:	Value Source 3,3',5,5'-Tetraiodo-L-thyronine ChEBI 3,5,3',5'-TETRAIODO-L-thyronine ChEBI 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine ChEBI L-T4 ChEBI Levothyroxin ChEBI Levothyroxine ChEBI LT4 ChEBI O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine ChEBI T4 ChEBI L-Thyroxine Kegg O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine Kegg 3,5,3'5'-Tetraiodo-L-thyronine Kegg Forthyron Kegg (-)-Thyroxine HMDB 3,3',5,5''-tetraiodo-L-Thyronine HMDB 3,5,3',5'-Tetraiodothyronine HMDB, MeSH D-Thyroxine HMDB DL-Thyroxin HMDB Henning HMDB L-3,5,3',5'-Tetraiodothyronine HMDB, MeSH L-Thyroxin HMDB Laevothyroxinum HMDB Levothroid HMDB, MeSH Levothyroxine sodium HMDB, MeSH Levothyroxinum HMDB Levoxyl HMDB, MeSH Prestwick_548 HMDB Synthroid HMDB, MeSH Tetraiodothyronine HMDB Tetramet HMDB THX HMDB Thyratabs HMDB Thyrax HMDB, MeSH Thyreoideum HMDB Thyroxin HMDB, MeSH Thyroxinal HMDB Thyroxine I 125 HMDB Thyroxine iodine HMDB Allphar brand OF levothyroxine sodium MeSH, HMDB Berlthyrox MeSH, HMDB Delalande, levothyroxin MeSH, HMDB Dexnon MeSH, HMDB Eferox MeSH, HMDB Eltroxin MeSH, HMDB Kern brand OF levothyroxine sodium MeSH, HMDB L-Thyrox MeSH, HMDB L-Thyroxin henning MeSH, HMDB L-Thyroxin beta MeSH, HMDB L-Thyroxine roche MeSH, HMDB Levothyroxin deladande MeSH, HMDB Lévothyrox MeSH, HMDB Merck lipha santé brand OF levothyroxine sodium MeSH, HMDB Nourypharma brand OF levothyroxine sodium MeSH, HMDB Oroxine MeSH, HMDB Aventis brand OF levothyroxine sodium MeSH, HMDB Euthyrox MeSH, HMDB Eutirox MeSH, HMDB Forest brand OF levothyroxine sodium MeSH, HMDB Genpharm brand OF levothyroxine sodium MeSH, HMDB GlaxoSmithKline brand OF levothyroxine sodium MeSH, HMDB Goldshield brand OF levothyroxine sodium MeSH, HMDB LThyroxin henning MeSH, HMDB levo-T MeSH, HMDB Sanofi synthelabo brand OF levothyroxine sodium MeSH, HMDB Sigma brand OF levothyroxine sodium MeSH, HMDB Synthrox MeSH, HMDB Thevier MeSH, HMDB Watson brand OF levothyroxine sodium MeSH, HMDB Berlin chemie brand OF levothyroxine sodium MeSH, HMDB Delalande brand OF levothyroxine sodium MeSH, HMDB Eltroxine MeSH, HMDB Hexal brand 2 OF levothyroxine sodium MeSH, HMDB L Thyroxine roche MeSH, HMDB Novothyral MeSH, HMDB Tiroidine MeSH, HMDB Vortex brand OF levothyroxine sodium MeSH, HMDB Abbot brand OF levothyroxine sodium MeSH, HMDB Berlin-chemie brand OF levothyroxine sodium MeSH, HMDB Byk brand OF levothyroxine sodium MeSH, HMDB Deladande, levothyroxin MeSH, HMDB GlaxoWellcome brand OF levothyroxine sodium MeSH, HMDB Henning berlin brand OF levothyroxine sodium MeSH, HMDB Hexal brand 1 OF levothyroxine sodium MeSH, HMDB L Thyrox MeSH, HMDB L Thyroxin henning MeSH, HMDB L Thyroxin beta MeSH, HMDB L Thyroxine MeSH, HMDB LThyroxin beta MeSH, HMDB leo, Tiroxina MeSH, HMDB levo T MeSH, HMDB LevoT MeSH, HMDB Levothyroid MeSH, HMDB Levothyroxin delalande MeSH, HMDB Levoxine MeSH, HMDB Merck brand OF levothyroxine sodium MeSH, HMDB Monarch brand OF levothyroxine sodium MeSH, HMDB Mova brand OF levothyroxine sodium MeSH, HMDB Novothyrox MeSH, HMDB O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosine MeSH, HMDB O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine MeSH, HMDB Roche brand OF levothyroxine sodium MeSH, HMDB Rudefsa brand OF levothyroxine sodium MeSH, HMDB Sodium levothyroxine MeSH, HMDB T4 Thyroid hormone MeSH, HMDB Thyroid hormone, T4 MeSH, HMDB Tiroxina leo MeSH, HMDB Unithroid MeSH, HMDB Betapharm brand OF levothyroxine sodium MeSH, HMDB
Chemical Formula:	C15H11I4NO4
Weight:	Average: 776.87 Monoisotopic: 776.686681525
InChI Key:	XUIIKFGFIJCVMT-LBPRGKRZSA-N
InChI:	InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1
CAS number:	Not Available
IUPAC Name:	(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
Traditional IUPAC Name:	levothyroxine
SMILES:	N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O
Chemical Taxonomy
Description	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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Phenylalanine and derivatives
Alternative Parents	Diphenylethers Phenylpropanoic acids Diarylethers Amphetamines and derivatives L-alpha-amino acids Phenoxy compounds Phenol ethers O-iodophenols Aralkylamines Iodobenzenes Aryl iodides Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organoiodides Carbonyl compounds Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
Substituents	Phenylalanine or derivatives Diphenylether Diaryl ether 3-phenylpropanoic-acid Alpha-amino acid Amphetamine or derivatives L-alpha-amino acid Phenoxy compound Phenol ether 2-halophenol 2-iodophenol Aralkylamine Phenol Halobenzene Iodobenzene Aryl halide Aryl iodide Benzenoid Monocyclic benzene moiety Amino acid Carboxylic acid Ether Monocarboxylic acid or derivatives Organoiodide Organonitrogen compound Organooxygen compound Organopnictogen compound Organic nitrogen compound Organic oxide Carbonyl group Primary amine Amine Hydrocarbon derivative Primary aliphatic amine Organic oxygen compound Organohalogen compound Aromatic homomonocyclic compound
Molecular Framework	Aromatic homomonocyclic compounds
External Descriptors	non-proteinogenic L-alpha-amino acid (CHEBI:18332 ) L-phenylalanine derivative (CHEBI:18332 ) iodophenol (CHEBI:18332 ) 2-halophenol (CHEBI:18332 ) thyroxine (CHEBI:18332 ) thyroxine (C01829 ) Other amino acids (C01829 ) Biogenic amines (C01829 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.009 g/L ALOGPS logP 1.15 ALOGPS logP 3.73 ChemAxon logS -4.9 ALOGPS pKa (Strongest Acidic) 0.27 ChemAxon pKa (Strongest Basic) 9.43 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 92.78 Ų ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 126.79 m³·mol⁻¹ ChemAxon Polarizability 49.4 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0f89-4002002900-0d489fed1cb888a2d9d0 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0ac9-0591664310-c9b7aec3184ebb20a2da View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-014i-2566449540-35bb942c7bcbcfe41af7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-00xr-3375497520-9dee3cb0c153e6c6df9e View in MoNA LC-MS/MS LC-MS/MS Spectrum - , positive splash10-0059-0001001900-83ff4aafed0b73c6c7b7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 35V, Negative splash10-004i-0900000000-6e0a640216afcce0837e View in MoNA LC-MS/MS LC-MS/MS Spectrum - 45V, Negative splash10-004i-0900000000-9223d3d63e3db43052a7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 60V, Negative splash10-004i-0900000000-1e8e674422aa4d820da7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-001i-0132219000-42259b5a596f74aec76f View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0udi-0019217000-baafc92556cb18d71b3a View in MoNA LC-MS/MS LC-MS/MS Spectrum - 30V, Negative splash10-004i-0900000000-bb154453510a75ca822c View in MoNA LC-MS/MS LC-MS/MS Spectrum - 15V, Negative splash10-004i-0900000000-f785346765de92765afd View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Positive splash10-001i-0000119000-af7b1e923ec5750514af View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-0f8j-1248309000-68eea5695ceb400ea5b0 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Positive splash10-0udi-0029337000-a85b59c3575dc95d36fd View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Positive splash10-001i-0003109000-480d647f8d49feeec28c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-01si-0000000900-524d052a32c1fe4b904d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-0000001900-553f6a4045ef2241fd85 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-014i-0009000000-d2431d885a79bb80b7a5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-0000000900-137b5f8f48031bc9aa4f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03fr-0004001900-db1d8cdb93785d786382 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0h9u-7029014300-3bd9620b0c6a8dd20c93 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-0000000900-95266ab7e52b7d3cb322 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-1700000900-195c16ab7434b857e712 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-0900000000-0dba40d354fa6a5575e0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0000000900-d76aec17d3d890cb64c1 View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 18332 HMDB ID HMDB0000248 Pubchem Compound ID Not Available Kegg ID C01829 ChemSpider ID 5614 Wikipedia ID Levothyroxine BioCyc ID Not Available