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Record Information
Version2.0
Creation Date2015-09-08 17:48:32 -0600
Update Date2015-09-08 17:48:32 -0600
Secondary Accession Numbers
  • ECMDB24025
Identification
Name:Thyroxine
Description
Structure
Thumb
Synonyms:
ValueSource
3,3',5,5'-Tetraiodo-L-thyronineChEBI
3,5,3',5'-TETRAIODO-L-thyronineChEBI
4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanineChEBI
L-T4ChEBI
LevothyroxinChEBI
LevothyroxineChEBI
LT4ChEBI
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosineChEBI
T4ChEBI
L-ThyroxineKegg
O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosineKegg
3,5,3'5'-Tetraiodo-L-thyronineKegg
ForthyronKegg
(-)-ThyroxineHMDB
3,3',5,5''-tetraiodo-L-ThyronineHMDB
3,5,3',5'-TetraiodothyronineHMDB, MeSH
D-ThyroxineHMDB
DL-ThyroxinHMDB
HenningHMDB
L-3,5,3',5'-TetraiodothyronineHMDB, MeSH
L-ThyroxinHMDB
LaevothyroxinumHMDB
LevothroidHMDB, MeSH
Levothyroxine sodiumHMDB, MeSH
LevothyroxinumHMDB
LevoxylHMDB, MeSH
Prestwick_548HMDB
SynthroidHMDB, MeSH
TetraiodothyronineHMDB
TetrametHMDB
THXHMDB
ThyratabsHMDB
ThyraxHMDB, MeSH
ThyreoideumHMDB
ThyroxinHMDB, MeSH
ThyroxinalHMDB
Thyroxine I 125HMDB
Thyroxine iodineHMDB
Allphar brand OF levothyroxine sodiumMeSH, HMDB
BerlthyroxMeSH, HMDB
Delalande, levothyroxinMeSH, HMDB
DexnonMeSH, HMDB
EferoxMeSH, HMDB
EltroxinMeSH, HMDB
Kern brand OF levothyroxine sodiumMeSH, HMDB
L-ThyroxMeSH, HMDB
L-Thyroxin henningMeSH, HMDB
L-Thyroxin betaMeSH, HMDB
L-Thyroxine rocheMeSH, HMDB
Levothyroxin deladandeMeSH, HMDB
LévothyroxMeSH, HMDB
Merck lipha santé brand OF levothyroxine sodiumMeSH, HMDB
Nourypharma brand OF levothyroxine sodiumMeSH, HMDB
OroxineMeSH, HMDB
Aventis brand OF levothyroxine sodiumMeSH, HMDB
EuthyroxMeSH, HMDB
EutiroxMeSH, HMDB
Forest brand OF levothyroxine sodiumMeSH, HMDB
Genpharm brand OF levothyroxine sodiumMeSH, HMDB
GlaxoSmithKline brand OF levothyroxine sodiumMeSH, HMDB
Goldshield brand OF levothyroxine sodiumMeSH, HMDB
LThyroxin henningMeSH, HMDB
levo-TMeSH, HMDB
Sanofi synthelabo brand OF levothyroxine sodiumMeSH, HMDB
Sigma brand OF levothyroxine sodiumMeSH, HMDB
SynthroxMeSH, HMDB
ThevierMeSH, HMDB
Watson brand OF levothyroxine sodiumMeSH, HMDB
Berlin chemie brand OF levothyroxine sodiumMeSH, HMDB
Delalande brand OF levothyroxine sodiumMeSH, HMDB
EltroxineMeSH, HMDB
Hexal brand 2 OF levothyroxine sodiumMeSH, HMDB
L Thyroxine rocheMeSH, HMDB
NovothyralMeSH, HMDB
TiroidineMeSH, HMDB
Vortex brand OF levothyroxine sodiumMeSH, HMDB
Abbot brand OF levothyroxine sodiumMeSH, HMDB
Berlin-chemie brand OF levothyroxine sodiumMeSH, HMDB
Byk brand OF levothyroxine sodiumMeSH, HMDB
Deladande, levothyroxinMeSH, HMDB
GlaxoWellcome brand OF levothyroxine sodiumMeSH, HMDB
Henning berlin brand OF levothyroxine sodiumMeSH, HMDB
Hexal brand 1 OF levothyroxine sodiumMeSH, HMDB
L ThyroxMeSH, HMDB
L Thyroxin henningMeSH, HMDB
L Thyroxin betaMeSH, HMDB
L ThyroxineMeSH, HMDB
LThyroxin betaMeSH, HMDB
leo, TiroxinaMeSH, HMDB
levo TMeSH, HMDB
LevoTMeSH, HMDB
LevothyroidMeSH, HMDB
Levothyroxin delalandeMeSH, HMDB
LevoxineMeSH, HMDB
Merck brand OF levothyroxine sodiumMeSH, HMDB
Monarch brand OF levothyroxine sodiumMeSH, HMDB
Mova brand OF levothyroxine sodiumMeSH, HMDB
NovothyroxMeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl) 3,5-diiodo-L-tyrosineMeSH, HMDB
O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosineMeSH, HMDB
Roche brand OF levothyroxine sodiumMeSH, HMDB
Rudefsa brand OF levothyroxine sodiumMeSH, HMDB
Sodium levothyroxineMeSH, HMDB
T4 Thyroid hormoneMeSH, HMDB
Thyroid hormone, T4MeSH, HMDB
Tiroxina leoMeSH, HMDB
UnithroidMeSH, HMDB
Betapharm brand OF levothyroxine sodiumMeSH, 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP1.15ALOGPS
logP3.73ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.27ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.79 m³·mol⁻¹ChemAxon
Polarizability49.4 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-4002002900-0d489fed1cb888a2d9d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ac9-0591664310-c9b7aec3184ebb20a2daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-2566449540-35bb942c7bcbcfe41af7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00xr-3375497520-9dee3cb0c153e6c6df9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0059-0001001900-83ff4aafed0b73c6c7b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0900000000-6e0a640216afcce0837eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-004i-0900000000-9223d3d63e3db43052a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-004i-0900000000-1e8e674422aa4d820da7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0132219000-42259b5a596f74aec76fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0019217000-baafc92556cb18d71b3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-0900000000-bb154453510a75ca822cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-004i-0900000000-f785346765de92765afdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000119000-af7b1e923ec5750514afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0f8j-1248309000-68eea5695ceb400ea5b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0029337000-a85b59c3575dc95d36fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0003109000-480d647f8d49feeec28cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-0000000900-524d052a32c1fe4b904dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000001900-553f6a4045ef2241fd85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0009000000-d2431d885a79bb80b7a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-137b5f8f48031bc9aa4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-0004001900-db1d8cdb93785d786382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h9u-7029014300-3bd9620b0c6a8dd20c93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000900-95266ab7e52b7d3cb322View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1700000900-195c16ab7434b857e712View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-0dba40d354fa6a5575e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000000900-d76aec17d3d890cb64c1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18332
HMDB IDHMDB0000248
Pubchem Compound IDNot Available
Kegg IDC01829
ChemSpider ID5614
Wikipedia IDLevothyroxine
BioCyc IDNot Available