Showing metabocard for Thyroxine (BMDB0000248)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
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Record Information
Version1.0
Creation Date2016-09-30 22:27:22 UTC
Update Date2020-05-11 20:56:54 UTC
BMDB IDBMDB0000248
Secondary Accession Numbers
  • BMDB00248
Metabolite Identification
Common NameThyroxine
DescriptionThyroxinee, also known as thyroxineee or Thyroxinee, 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. Thyroxinee is a drug which is used for use alone or in combination with antithyroid agents to treat hypothyroidism, goiter, chronic lymphocytic thyroiditis, myxedema coma, and stupor. Thyroxinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Thyroxinee exists in all living organisms, ranging from bacteria to humans. In cattle, thyroxinee is involved in the metabolic pathway called thyroid hormone synthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC15H11I4NO4
Average Molecular Weight776.87
Monoisotopic Molecular Weight776.686681525
IUPAC Name(2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
Traditional Namelevothyroxine
CAS Registry Number51-48-9
SMILES
N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O
InChI Identifier
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
InChI KeyXUIIKFGFIJCVMT-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
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point235.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Fibroblasts
  • Intestine
  • Neuron
  • Ovary
  • Placenta
  • Platelet
  • Prostate Tissue
  • Skeletal Muscle
  • Spleen
  • Testis
  • Thyroid Gland
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0000248
DrugBank IDDB00451
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5614
KEGG Compound IDC01829
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevothyroxine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18332
References
Synthesis ReferenceMartinovich, V. P.; Katok, Ya. M.; Fil'chenkov, N. A.; Sviridov, O. V. Conjugated synthesis of L-thyroxine and L-triiodothyronine. Vestsi Natsyyanal'nai Akademii Navuk Belarusi, Seryya Khimichnykh Navuk (2004), (1), 85-92.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Type II iodothyronine deiodinase
General function:
Involved in selenium binding
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:
Q5I3B2
Molecular weight:
30303.0
Enzyme Details
2. Thyroxine 5-deiodinase
General function:
Involved in selenium binding
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:
Q5I3B1
Molecular weight:
33888.0
Enzyme Details
3. Solute carrier organic anion transporter family member 3A1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions. Mediates transport of prostaglandins (PG) E1 and E2, thyroxine (T4), deltorphin II, BQ-123 and vasopressin.
Gene Name:
SLCO3A1
Uniprot ID:
Q8HYW2
Molecular weight:
76555.0