Showing metabocard for Liothyronine (BMDB0000265)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:36 UTC
Update Date2020-06-04 20:57:12 UTC
MCDB ID BMDB0000265
Secondary Accession Numbers
  • BMDB00265
Metabolite Identification
Common NameLiothyronine
DescriptionLiothyronine, 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.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05a9-5090378000-014ef55558b58a3d38f22017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-10-17View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Liothyronine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-0009001000-1d47041336da63b556e42012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-000i-1009001000-15f70073b9018f013c9c2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-000i-0009000000-71c231d7a3ab505815ff2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0000009000-f932659d1e6d8a6229852012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0000009000-6506a7a71dab928abfb02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fc0-0700119000-1df6db0e3031eb2739fa2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0900000000-973fc871534b19242cc82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-ac3c4a198bb017dc7ccc2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0000009000-2770ece749a9fa1042f42012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0000009000-881174c66da97022d6452012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-0000019000-6f798ae76702a30533392012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-0000219000-d2ca9f0cc3c1b47176b52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-056r-0021915000-6f3810619f383bce651a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0000009000-f932659d1e6d8a6229852017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0000009000-6506a7a71dab928abfb02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fc0-0700119000-1df6db0e3031eb2739fa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-973fc871534b19242cc82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-ac3c4a198bb017dc7ccc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0000009000-2770ece749a9fa1042f42017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0000009000-4d60e1441642731114642017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000149000-87babecf610c68223da52017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016r-0039010000-b57f6dd23e6456cf7c1e2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0010009000-50e441d89395debe176b2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0050139000-a259e39ad1204b60b3732017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9262431000-bcc1f7554c4e309cef172017-07-26View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified500 uM details
HMDB IDHMDB0000265
DrugBank IDDB00279
Phenol Explorer Compound IDNot Available
FoodDB 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
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. 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. [PubMed:3530717 ]