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Record Information
Version3.6
Creation Date2006-05-22 15:12:06 UTC
Update Date2016-02-11 01:05:46 UTC
HMDB IDHMDB02728
Secondary Accession NumbersNone
Metabolite Identification
Common NameThyroxine sulfate
DescriptionThyroxine Sulfate (abbreviated T4) is a major Thyroid hormone metabolite secreted by follicular cells of the Thyroid gland. T4 is transported in blood, with 99.95% of the secreted T4 being protein bound, principally to thyroxine binding globulin (TBG) and to a lesser extent to thyroxine binding pre-albumin (TBPA) and serum albumin. T4 is involved in controlling the rate of metabolic processes in the body and influencing physical development. T4 is considered a prohormone and a reservoir for the active thyroid hormone triiodothyronine (T3), T4 being converted as required in the tissues by deiodinases.
Structure
Thumb
Synonyms
ValueSource
3,5,3',5'-tetraiodo-L-Thyronine 4'-O-sulfateHMDB
3,5,3',5'-tetraiodo-L-Thyronine 4'-O-sulphateHMDB
3,5,3',5'-tetraiodo-L-Thyronine 4-O-sulfateHMDB
3,5,3',5'-tetraiodo-L-Thyronine 4-O-sulphateHMDB
3-[4-(4-Hydroxy-3,5-diiodophenoxy-4-O-sulfate)-3,5-diiodophenyl]-L-alanineHMDB
3-[4-(4-Hydroxy-3,5-diiodophenoxy-4-O-sulphate)-3,5-diiodophenyl]-L-alanineHMDB
L-Thyroxine 4'-O-sulfateHMDB
L-Thyroxine 4'-O-sulphateHMDB
O-(4-Hydroxy-3,5-diiodophenyl-4-O-sulfate)-3,5-diiodo-L-tyrosineHMDB
O-(4-Hydroxy-3,5-diiodophenyl-4-O-sulphate)-3,5-diiodo-L-tyrosineHMDB
T4SHMDB
Thyroxine sulphateHMDB
Chemical FormulaC15H11I4NO7S
Average Molecular Weight856.933
Monoisotopic Molecular Weight856.643496081
IUPAC Name(2S)-2-amino-3-{4-[3,5-diiodo-4-(sulfooxy)phenoxy]-3,5-diiodophenyl}propanoic acid
Traditional Namethyroxine sulfic acid
CAS Registry Number77074-49-8
SMILES
N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(OS(O)(=O)=O)C(I)=C2)C(I)=C1)C(O)=O
InChI Identifier
InChI=1S/C15H11I4NO7S/c16-8-1-6(3-12(20)15(21)22)2-9(17)13(8)26-7-4-10(18)14(11(19)5-7)27-28(23,24)25/h1-2,4-5,12H,3,20H2,(H,21,22)(H,23,24,25)/t12-/m0/s1
InChI KeyInChIKey=QYXIJUZWSSQICT-LBPRGKRZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Phenylsulfate
  • 3-phenylpropanoic-acid
  • Diaryl ether
  • L-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Aralkylamine
  • Sulfuric acid monoester
  • Iodobenzene
  • Halobenzene
  • Amino fatty acid
  • Fatty acyl
  • Sulfuric acid ester
  • Sulfate-ester
  • Aryl iodide
  • Aryl halide
  • Organic sulfuric acid or derivatives
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organoiodide
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Hormone
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0047 mg/mLALOGPS
logP0.81ALOGPS
logP4.31ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)-3ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.15 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity136.78 m3·mol-1ChemAxon
Polarizability54.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000019 +/- 0.0000012 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000021 +/- 0.0000043 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000245 +/- 0.000026 uMNewborn (0-30 days old)Both
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000033 +/- 0.000010 uMAdult (>18 years old)Both
Hyperthyroidism
details
BloodDetected and Quantified0.000042 +/- 0.000015 uMAdult (>18 years old)BothHypothyroidism details
BloodDetected and Quantified0.000034 +/- 0.0000069 uMAdult (>18 years old)Both
Euthyroidism
details
Associated Disorders and Diseases
Disease References
Hyperthyroidism
  1. Chopra IJ, Santini F, Hurd RE, Chua Teco GN: A radioimmunoassay for measurement of thyroxine sulfate. J Clin Endocrinol Metab. 1993 Jan;76(1):145-50. [8421080 ]
Hypothyroidism
  1. Chopra IJ, Santini F, Hurd RE, Chua Teco GN: A radioimmunoassay for measurement of thyroxine sulfate. J Clin Endocrinol Metab. 1993 Jan;76(1):145-50. [8421080 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00555
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023056
KNApSAcK IDNot Available
Chemspider ID116397
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02728
Metagene LinkHMDB02728
METLIN ID988
PubChem Compound131742
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chopra IJ, Santini F, Hurd RE, Chua Teco GN: A radioimmunoassay for measurement of thyroxine sulfate. J Clin Endocrinol Metab. 1993 Jan;76(1):145-50. [8421080 ]
  2. Wu SY, Huang WS, Polk D, Florsheim WH, Green WL, Fisher DA: Identification of thyroxine-sulfate (T4S) in human serum and amniotic fluid by a novel T4S radioimmunoassay. Thyroid. 1992 Summer;2(2):101-5. [1525576 ]
  3. Peeters RP, Kester MH, Wouters PJ, Kaptein E, van Toor H, Visser TJ, Van den Berghe G: Increased thyroxine sulfate levels in critically ill patients as a result of a decreased hepatic type I deiodinase activity. J Clin Endocrinol Metab. 2005 Dec;90(12):6460-5. Epub 2005 Sep 27. [16189257 ]
  4. Wu S, Polk D, Wong S, Reviczky A, Vu R, Fisher DA: Thyroxine sulfate is a major thyroid hormone metabolite and a potential intermediate in the monodeiodination pathways in fetal sheep. Endocrinology. 1992 Oct;131(4):1751-6. [1396320 ]
  5. Huang WS, Cherng SC, Wang CH, Shih BF, Kuo SW, Wu SY: Increased urinary thyroxine sulfate excretion in thyroxine therapy. Endocr J. 1997 Aug;44(4):467-72. [9447277 ]

Enzymes

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
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
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