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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:20:01 UTC
HMDB IDHMDB0000265
Secondary Accession Numbers
  • HMDB0006780
  • HMDB00265
  • HMDB06780
Metabolite Identification
Common NameLiothyronine
DescriptionLiothyronine is a T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone that is finally delivered and used by the tissues is mainly T3. Liothyronine is mildly toxic by ingestion and is an experimental teratogen. When heated to decomposition it emits toxic fumes of NOx, I(-), and Cl(-) (Sax's Dangerous Properties of Industrial Materials).
Structure
Data?1582752119
Synonyms
ValueSource
3,5,3'-Triiodo-L-thyronineChEBI
3,5,3'-TriiodothyronineChEBI
3,5,3'TRIIODOTHYRONINEChEBI
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanineChEBI
L-3,5,3'-TriiodothyronineChEBI
L-T3ChEBI
LiothyroninumChEBI
LiotironinaChEBI
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosineChEBI
T3ChEBI
TertroxinChEBI
TresitopeChEBI
TriiodothyronineChEBI
3,3',5-Triiodo-L-thyronineKegg
ThyrolarKegg
3,3',5-TriiodothyronineHMDB
CytomelHMDB
T3 Thyroid hormoneHMDB
Thyroid hormone, T3HMDB
Liothyronine sodiumHMDB
3,3',5'-Triiodo-L-thyronineHMDB
3,3',5'-TriiodothyronineHMDB
4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanineHMDB
CyronineHMDB
L-3,3',5-Triiodo-thyronineHMDB
L-3,3',5-TriiodothyronineHMDB
L-3-[4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-alanineHMDB
L-LiothyronineHMDB
L-TriiodothyronineHMDB
LiothyroninHMDB
Triiodo-L-thyronineHMDB
Chemical FormulaC15H12I3NO4
Average Molecular Weight650.9735
Monoisotopic Molecular Weight650.790038137
IUPAC Name(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
Traditional Nameliothyronine
CAS Registry Number6893-02-3
SMILES
N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O
InChI Identifier
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
InChI KeyAUYYCJSJGJYCDS-LBPRGKRZSA-N
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
  • 2-iodophenol
  • 2-halophenol
  • Phenol ether
  • Iodobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Halobenzene
  • Phenol
  • Aralkylamine
  • Aryl iodide
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Ether
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organohalogen compound
  • Organoiodide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+MetCCS_train_pos209.67730932474
[M+H]+Not Available209.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00000488
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP0.82ALOGPS
logP2.8ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)0.3ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.43 m³·mol⁻¹ChemAxon
Polarizability43.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+203.72332859911
AllCCS[M-H]-197.66532859911
DeepCCS[M+H]+207.03330932474
DeepCCS[M+H]+206.91330932474
DeepCCS[M-H]-204.48530932474
DeepCCS[M-H]-204.36330932474
DeepCCS[M-2H]-238.78230932474
DeepCCS[M+Na]+214.13530932474
DeepCCS[M-2H]-238.15230932474
DeepCCS[M+Na]+213.50530932474
AllCCS[M+H]+203.732859911
AllCCS[M+H-H2O]+202.332859911
AllCCS[M+NH4]+205.032859911
AllCCS[M+Na]+205.332859911
AllCCS[M-H]-197.732859911
AllCCS[M+Na-2H]-199.432859911
AllCCS[M+HCOO]-201.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LiothyronineN[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O4675.4Standard polar33892256
LiothyronineN[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O3583.5Standard non polar33892256
LiothyronineN[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C(I)=C1)C(O)=O3771.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Liothyronine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@H](N)C(=O)O)C=C2I)C=C1I3500.9Semi standard non polar33892256
Liothyronine,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C13505.5Semi standard non polar33892256
Liothyronine,1TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O3540.4Semi standard non polar33892256
Liothyronine,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C13520.6Semi standard non polar33892256
Liothyronine,2TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O3516.8Semi standard non polar33892256
Liothyronine,2TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C3485.2Semi standard non polar33892256
Liothyronine,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C3627.2Semi standard non polar33892256
Liothyronine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C3509.7Semi standard non polar33892256
Liothyronine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C3176.4Standard non polar33892256
Liothyronine,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C3131.5Standard polar33892256
Liothyronine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I3638.7Semi standard non polar33892256
Liothyronine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I3317.3Standard non polar33892256
Liothyronine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)C=C2I)C=C1I3305.8Standard polar33892256
Liothyronine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3610.9Semi standard non polar33892256
Liothyronine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3279.4Standard non polar33892256
Liothyronine,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)N([Si](C)(C)C)[Si](C)(C)C3301.0Standard polar33892256
Liothyronine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(OC2=C(I)C=C(C[C@H](N)C(=O)O)C=C2I)C=C1I3786.6Semi standard non polar33892256
Liothyronine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C13777.3Semi standard non polar33892256
Liothyronine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O3786.9Semi standard non polar33892256
Liothyronine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C14009.3Semi standard non polar33892256
Liothyronine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O[Si](C)(C)C(C)(C)C)C(I)=C2)C(I)=C1)C(=O)O4035.1Semi standard non polar33892256
Liothyronine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O[Si](C)(C)C(C)(C)C3997.9Semi standard non polar33892256
Liothyronine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(I)=C(OC2=CC=C(O)C(I)=C2)C(I)=C1)C(=O)O)[Si](C)(C)C(C)(C)C4071.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (Non-derivatized) - 70eV, Positivesplash10-05a9-5090378000-014ef55558b58a3d38f22017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Liothyronine GC-MS ("Liothyronine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-000i-0009001000-1d47041336da63b556e42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-000i-1009001000-15f70073b9018f013c9c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-000i-0009000000-71c231d7a3ab505815ff2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0udi-0000009000-f932659d1e6d8a6229852012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0udi-0000009000-6506a7a71dab928abfb02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0fc0-0700119000-1df6db0e3031eb2739fa2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-0900000000-973fc871534b19242cc82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-0900000000-ac3c4a198bb017dc7ccc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0udi-0000009000-2770ece749a9fa1042f42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0udi-0000009000-881174c66da97022d6452012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0a4i-0000019000-6f798ae76702a30533392012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0a4i-0000219000-d2ca9f0cc3c1b47176b52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-056r-0021915000-6f3810619f383bce651a2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOFsplash10-0udi-0000009000-f932659d1e6d8a6229852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOFsplash10-0udi-0000009000-6506a7a71dab928abfb02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOFsplash10-0fc0-0700119000-1df6db0e3031eb2739fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOFsplash10-004i-0900000000-973fc871534b19242cc82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , negative-QTOFsplash10-004i-0900000000-ac3c4a198bb017dc7ccc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Liothyronine LC-ESI-QQ , positive-QTOFsplash10-0udi-0000009000-2770ece749a9fa1042f42017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Liothyronine 10V, Positive-QTOFsplash10-0pb9-0000009000-4d60e1441642731114642017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Liothyronine 20V, Positive-QTOFsplash10-0a4i-0000149000-87babecf610c68223da52017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Liothyronine 40V, Positive-QTOFsplash10-016r-0039010000-b57f6dd23e6456cf7c1e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Liothyronine 10V, Negative-QTOFsplash10-0002-0010009000-50e441d89395debe176b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Liothyronine 20V, Negative-QTOFsplash10-001j-0050139000-a259e39ad1204b60b3732017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Liothyronine 40V, Negative-QTOFsplash10-00e9-9262431000-bcc1f7554c4e309cef172017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Intestine
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0029 +/- 0.00019 uMChildren (1-13 years old)BothNormal details
BloodDetected and Quantified0.002 +/- 0.0006 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.000013 - 0.000028 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0000038 - 0.0000060 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0000031-0.0000077 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified0.0 - 1.0 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0011 +/- 0.00024 uMChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus) details
BloodDetected and Quantified0.0014 +/- 0.0004 uMAdolescent (13-18 years old)FemaleAnorexia nervosa details
BloodDetected and Quantified0.00169 uMAdult (>18 years old)Female
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
details
BloodDetected and Quantified0.0000041 uMAdult (>18 years old)FemaleProprotein Convertase 1/3 Deficiency details
UrineDetected and Quantified0.00075 +/- 0.00033 umol/mmol creatinineAdult (>18 years old)BothHyperthyroidism details
UrineDetected and Quantified0.000014 +/- 0.000015 umol/mmol creatinineAdult (>18 years old)BothHypothyroidism details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  1. Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. [PubMed:10197568 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
  1. Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ]
Proprotein Convertase 1/3 Deficiency
  1. O'Rahilly S, Gray H, Humphreys PJ, Krook A, Polonsky KS, White A, Gibson S, Taylor K, Carr C: Brief report: impaired processing of prohormones associated with abnormalities of glucose homeostasis and adrenal function. N Engl J Med. 1995 Nov 23;333(21):1386-90. doi: 10.1056/NEJM199511233332104. [PubMed:7477119 ]
Hyperthyroidism
  1. Yoshida K, Sakurada T, Kaise N, Yamamoto M, Kaise K, Saito S, Yoshinaga K: Measurement of triiodothyronine in urine. Tohoku J Exp Med. 1980 Dec;132(4):389-95. [PubMed:7256725 ]
Hypothyroidism
  1. Yoshida K, Sakurada T, Kaise N, Yamamoto M, Kaise K, Saito S, Yoshinaga K: Measurement of triiodothyronine in urine. Tohoku J Exp Med. 1980 Dec;132(4):389-95. [PubMed:7256725 ]
Associated OMIM IDs
  • 606788 (Anorexia nervosa)
  • 201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
  • 600955 (Proprotein Convertase 1/3 Deficiency)
DrugBank IDDB00279
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC02465
BioCyc IDCPD-10813
BiGG IDNot Available
Wikipedia LinkTriiodothyronine
METLIN IDNot Available
PubChem Compound5920
PDB IDNot Available
ChEBI ID18258
Food Biomarker OntologyNot Available
VMH IDTRIODTHY
MarkerDB IDMDB00000128
Good Scents IDNot Available
References
Synthesis ReferenceSalamonczyk, 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
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schwartz CE, May MM, Carpenter NJ, Rogers RC, Martin J, Bialer MG, Ward J, Sanabria J, Marsa S, Lewis JA, Echeverri R, Lubs HA, Voeller K, Simensen RJ, Stevenson RE: Allan-Herndon-Dudley syndrome and the monocarboxylate transporter 8 (MCT8) gene. Am J Hum Genet. 2005 Jul;77(1):41-53. Epub 2005 May 11. [PubMed:15889350 ]
  2. Gil'miiarova FN, Pervova IuV, Radomskaia VM, Gergel' NI, Tarasova SV: [Levels of unified metabolites and thyroid hormones in blood and oral fluid of children with minimal brain dysfunction]. Biomed Khim. 2004 Mar-Apr;50(2):204-10. [PubMed:15179829 ]
  3. Escobar-Morreale HF, Botella-Carretero JI, Gomez-Bueno M, Galan JM, Barrios V, Sancho J: Thyroid hormone replacement therapy in primary hypothyroidism: a randomized trial comparing L-thyroxine plus liothyronine with L-thyroxine alone. Ann Intern Med. 2005 Mar 15;142(6):412-24. [PubMed:15767619 ]
  4. Stalenheim EG: Long-term validity of biological markers of psychopathy and criminal recidivism: follow-up 6-8 years after forensic psychiatric investigation. Psychiatry Res. 2004 Jan 1;121(3):281-91. [PubMed:14675747 ]
  5. Zimmermann-Belsing T, Dreyer M, Holst JJ, Feldt-Rasmussen U: The relationship between the serum leptin concentrations of thyrotoxic patients during treatment and their total fat mass is different from that of normal subjects. Clin Endocrinol (Oxf). 1998 Nov;49(5):589-95. [PubMed:10197073 ]
  6. Holt PJ: In vitro responses of the epidermis to triiodothyronine. J Invest Dermatol. 1978 Sep;71(3):202-4. [PubMed:690484 ]
  7. Mizuma H, Murakami M, Mori M: Thyroid hormone activation in human vascular smooth muscle cells: expression of type II iodothyronine deiodinase. Circ Res. 2001 Feb 16;88(3):313-8. [PubMed:11179199 ]
  8. Himms-Hagen J: Brown adipose tissue thermogenesis: interdisciplinary studies. FASEB J. 1990 Aug;4(11):2890-8. [PubMed:2199286 ]
  9. Gledhill RF, Dessein PH, Van der Merwe CA: Treatment of Raynaud's phenomenon with triiodothyronine corrects co-existent autonomic dysfunction: preliminary findings. Postgrad Med J. 1992 Apr;68(798):263-7. [PubMed:1409189 ]
  10. Kassem M, Brixen K, Mosekilde L, Blum WF, Flyvbjerg A: Effects of growth hormone treatment on serum levels of insulin-like growth factors (IGFs) and IGF binding proteins 1-4 in postmenopausal women. Clin Endocrinol (Oxf). 1998 Dec;49(6):747-56. [PubMed:10209562 ]
  11. Llewellyn L, Ramsurn VP, Wigham T, Sweeney GE, Power DM: Cloning, characterisation and expression of the apolipoprotein A-I gene in the sea bream (Sparus aurata). Biochim Biophys Acta. 1998 Nov 8;1442(2-3):399-404. [PubMed:9804999 ]
  12. Dutkiewicz S, Witeska A, Nauman A: The deiodination of thyroxine to triiodothyronine in the testes of patients with prostate cancer. Int Urol Nephrol. 1995;27(1):81-5. [PubMed:7615374 ]
  13. Rosenbaum M, Goldsmith R, Bloomfield D, Magnano A, Weimer L, Heymsfield S, Gallagher D, Mayer L, Murphy E, Leibel RL: Low-dose leptin reverses skeletal muscle, autonomic, and neuroendocrine adaptations to maintenance of reduced weight. J Clin Invest. 2005 Dec;115(12):3579-86. [PubMed:16322796 ]
  14. Urcelay E, Jareno MA, Menaya J, Parrilla R, Ayuso MS, Martin-Requero A: Cloning and functional characterization of the 5' regulatory region of the human mitochondrial glycerol-3-phosphate dehydrogenase gene. Lack of 3,5,3'-triiodothyronine responsiveness in adipose tissue. Eur J Biochem. 2000 Dec;267(24):7209-17. [PubMed:11106433 ]
  15. Lebon V, Dufour S, Petersen KF, Ren J, Jucker BM, Slezak LA, Cline GW, Rothman DL, Shulman GI: Effect of triiodothyronine on mitochondrial energy coupling in human skeletal muscle. J Clin Invest. 2001 Sep;108(5):733-7. [PubMed:11544279 ]
  16. Iwao H, Abe Y: [Expression of the renin and angiotensinogen genes]. Nihon Yakurigaku Zasshi. 1991 Jan;97(1):1-11. [PubMed:2045011 ]
  17. Calvo R, Obregon MJ, Ruiz de Ona C, Escobar del Rey F, Morreale de Escobar G: Congenital hypothyroidism, as studied in rats. Crucial role of maternal thyroxine but not of 3,5,3'-triiodothyronine in the protection of the fetal brain. J Clin Invest. 1990 Sep;86(3):889-99. [PubMed:2394838 ]
  18. Haas MJ, Fishman M, Mreyoud A, Mooradian AD: Thyroid hormone responsive protein (THRP) mediates thyroid hormone-induced cytotoxicity in primary neuronal cultures. Exp Brain Res. 2005 Jan;160(4):424-32. Epub 2004 Oct 15. [PubMed:15490139 ]

Enzymes

General function:
Involved in calcium ion binding
Specific function:
Iodination and coupling of the hormonogenic tyrosines in thyroglobulin to yield the thyroid hormones T(3) and T(4).
Gene Name:
TPO
Uniprot ID:
P07202
Molecular weight:
102961.63
Reactions
Iodotyrosine + 3,5-Diiodo-L-tyrosine + Hydrogen peroxide → Liothyronine + 2-Aminoacrylic acid + Waterdetails
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine) and of T3 into T2 (3,3'-diiodothyronine). Plays a role in providing a source of plasma T3 by deiodination of T4 in peripheral tissues such as liver and kidney.
Gene Name:
DIO1
Uniprot ID:
P49895
Molecular weight:
28924.21
Reactions
Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)details
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into T3 (3,5,3'-triiodothyronine). Essential for providing the brain with appropriate levels of T3 during the critical period of development.
Gene Name:
DIO2
Uniprot ID:
Q92813
Molecular weight:
30551.48
Reactions
Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)details
General function:
Involved in hormone activity
Specific function:
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain
Gene Name:
TTR
Uniprot ID:
P02766
Molecular weight:
15886.9
General function:
Involved in transport
Specific function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:
ALB
Uniprot ID:
P02768
Molecular weight:
69365.9
General function:
Involved in serine-type endopeptidase inhibitor activity
Specific function:
Major thyroid hormone transport protein in serum
Gene Name:
SERPINA7
Uniprot ID:
P05543
Molecular weight:
46324.1
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
High affinity receptor for triiodothyronine
Gene Name:
THRB
Uniprot ID:
P10828
Molecular weight:
52787.2
General function:
Involved in thyroxine 5'-deiodinase activity
Specific function:
Responsible for the deiodination of T4 (3,5,3',5'-tetraiodothyronine) into RT3 (3,3',5'-triiodothyronine) and of T3 (3,5,3'-triiodothyronine) into T2 (3,3'-diiodothyronine). RT3 and T2 are inactive metabolites. May play a role in preventing premature exposure of developing fetal tissues to adult levels of thyroid hormones. Can regulate circulating fetal thyroid hormone concentrations throughout gestation. Essential role for regulation of thyroid hormone inactivation during embryological development.
Gene Name:
DIO3
Uniprot ID:
P55073
Molecular weight:
33947.175
Reactions
Liothyronine + I(-) + A + Hydrogen Ion → Thyroxine + AH(2)details
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. High affinity receptor for triiodothyronine
Gene Name:
THRA
Uniprot ID:
P10827
Molecular weight:
54815.1